JPH03174412A - Production of poly-alpha-olefin - Google Patents
Production of poly-alpha-olefinInfo
- Publication number
- JPH03174412A JPH03174412A JP7182990A JP7182990A JPH03174412A JP H03174412 A JPH03174412 A JP H03174412A JP 7182990 A JP7182990 A JP 7182990A JP 7182990 A JP7182990 A JP 7182990A JP H03174412 A JPH03174412 A JP H03174412A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- acid
- component
- olefin
- compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920013639 polyalphaolefin Polymers 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- -1 SiO2) Chemical class 0.000 claims abstract description 35
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 18
- 150000002367 halogens Chemical class 0.000 claims abstract description 18
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 16
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 16
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 13
- 239000004711 α-olefin Substances 0.000 claims abstract description 13
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 11
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims abstract description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 9
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 6
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 6
- 239000011949 solid catalyst Substances 0.000 claims abstract description 5
- 150000002902 organometallic compounds Chemical class 0.000 claims abstract description 4
- 239000011777 magnesium Substances 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 11
- 239000010936 titanium Substances 0.000 claims description 10
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 8
- 229910000077 silane Inorganic materials 0.000 claims description 8
- 238000003077 quantum chemistry computational method Methods 0.000 claims description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract description 12
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract description 12
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 abstract description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 5
- XGZGKDQVCBHSGI-UHFFFAOYSA-N butyl(triethoxy)silane Chemical compound CCCC[Si](OCC)(OCC)OCC XGZGKDQVCBHSGI-UHFFFAOYSA-N 0.000 abstract description 4
- 238000004364 calculation method Methods 0.000 abstract description 4
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000377 silicon dioxide Substances 0.000 abstract description 2
- 229910052681 coesite Inorganic materials 0.000 abstract 1
- 229910052906 cristobalite Inorganic materials 0.000 abstract 1
- 235000012239 silicon dioxide Nutrition 0.000 abstract 1
- 229910052682 stishovite Inorganic materials 0.000 abstract 1
- 229910052905 tridymite Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 description 27
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 19
- 229910052739 hydrogen Inorganic materials 0.000 description 14
- 229910052782 aluminium Inorganic materials 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 11
- 150000002681 magnesium compounds Chemical class 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 10
- 150000003609 titanium compounds Chemical class 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000001336 alkenes Chemical class 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 150000003377 silicon compounds Chemical class 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 150000001733 carboxylic acid esters Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 150000003961 organosilicon compounds Chemical class 0.000 description 5
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 230000000737 periodic effect Effects 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 125000005234 alkyl aluminium group Chemical group 0.000 description 3
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000037048 polymerization activity Effects 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- ZLYYJUJDFKGVKB-UPHRSURJSA-N (z)-but-2-enedioyl dichloride Chemical compound ClC(=O)\C=C/C(Cl)=O ZLYYJUJDFKGVKB-UPHRSURJSA-N 0.000 description 2
- FAXWFCTVSHEODL-UHFFFAOYSA-N 2,4-dibromophenol Chemical compound OC1=CC=C(Br)C=C1Br FAXWFCTVSHEODL-UHFFFAOYSA-N 0.000 description 2
- RXGUIWHIADMCFC-UHFFFAOYSA-N 2-Methylpropyl 2-methylpropionate Chemical compound CC(C)COC(=O)C(C)C RXGUIWHIADMCFC-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 description 2
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
- RWUMREWUNMCLCM-UHFFFAOYSA-N 2-methylprop-2-enoyl iodide Chemical compound CC(=C)C(I)=O RWUMREWUNMCLCM-UHFFFAOYSA-N 0.000 description 2
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- 101100111947 Arabidopsis thaliana CYP72C1 gene Proteins 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- NMEZJSDUZQOPFE-UHFFFAOYSA-N Cyclohex-1-enecarboxylic acid Chemical compound OC(=O)C1=CCCCC1 NMEZJSDUZQOPFE-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- KCXZNSGUUQJJTR-UHFFFAOYSA-N Di-n-hexyl phthalate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCC KCXZNSGUUQJJTR-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 229910005267 GaCl3 Inorganic materials 0.000 description 2
- 101100439244 Glycine max CHI2-A gene Proteins 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- YZBOVSFWWNVKRJ-UHFFFAOYSA-N Monobutylphthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(O)=O YZBOVSFWWNVKRJ-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- LEKJTGQWLAUGQA-UHFFFAOYSA-N acetyl iodide Chemical compound CC(I)=O LEKJTGQWLAUGQA-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 229910052785 arsenic Inorganic materials 0.000 description 2
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- VJVUKRSEEMNRCM-UHFFFAOYSA-L butan-1-olate titanium(4+) dichloride Chemical compound [Cl-].[Cl-].CCCCO[Ti+2]OCCCC VJVUKRSEEMNRCM-UHFFFAOYSA-L 0.000 description 2
- NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 description 2
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 101150071577 chi2 gene Proteins 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 2
- WMPOZLHMGVKUEJ-UHFFFAOYSA-N decanedioyl dichloride Chemical compound ClC(=O)CCCCCCCCC(Cl)=O WMPOZLHMGVKUEJ-UHFFFAOYSA-N 0.000 description 2
- HJXBDPDUCXORKZ-UHFFFAOYSA-N diethylalumane Chemical compound CC[AlH]CC HJXBDPDUCXORKZ-UHFFFAOYSA-N 0.000 description 2
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 2
- MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical compound CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- GCPCLEKQVMKXJM-UHFFFAOYSA-N ethoxy(diethyl)alumane Chemical compound CCO[Al](CC)CC GCPCLEKQVMKXJM-UHFFFAOYSA-N 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 description 2
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N iodoform Chemical compound IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- YDSWCNNOKPMOTP-UHFFFAOYSA-N mellitic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O YDSWCNNOKPMOTP-UHFFFAOYSA-N 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- YSTQWZZQKCCBAY-UHFFFAOYSA-L methylaluminum(2+);dichloride Chemical compound C[Al](Cl)Cl YSTQWZZQKCCBAY-UHFFFAOYSA-L 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- BCRPRYVGWGKIEQ-UHFFFAOYSA-J titanium(4+) dichloride diphenoxide Chemical compound Cl[Ti+2]Cl.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 BCRPRYVGWGKIEQ-UHFFFAOYSA-J 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- PFYGZTWREWTDJX-LNKPDPKZSA-N (Z)-4-ethoxy-4-oxobut-2-enoic acid hydrochloride Chemical compound Cl.CCOC(=O)\C=C/C(O)=O PFYGZTWREWTDJX-LNKPDPKZSA-N 0.000 description 1
- CXENHBSYCFFKJS-OXYODPPFSA-N (Z,E)-alpha-farnesene Chemical compound CC(C)=CCC\C(C)=C\C\C=C(\C)C=C CXENHBSYCFFKJS-OXYODPPFSA-N 0.000 description 1
- WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 1
- XGSSMJZGYVOGEM-OWOJBTEDSA-N (e)-but-2-enedioyl dibromide Chemical compound BrC(=O)\C=C\C(Br)=O XGSSMJZGYVOGEM-OWOJBTEDSA-N 0.000 description 1
- ZLYYJUJDFKGVKB-OWOJBTEDSA-N (e)-but-2-enedioyl dichloride Chemical compound ClC(=O)\C=C\C(Cl)=O ZLYYJUJDFKGVKB-OWOJBTEDSA-N 0.000 description 1
- RJUIDDKTATZJFE-NSCUHMNNSA-N (e)-but-2-enoyl chloride Chemical compound C\C=C\C(Cl)=O RJUIDDKTATZJFE-NSCUHMNNSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- POJPQMDDRCILHJ-UHFFFAOYSA-N 1,1,1,2,2,2-hexabromoethane Chemical compound BrC(Br)(Br)C(Br)(Br)Br POJPQMDDRCILHJ-UHFFFAOYSA-N 0.000 description 1
- QQAHAGNPDBPSJP-UHFFFAOYSA-N 1,1,1,2,2,3,3,3-octachloropropane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)C(Cl)(Cl)Cl QQAHAGNPDBPSJP-UHFFFAOYSA-N 0.000 description 1
- IGDVFIQVQXDOFA-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,4-decabromobutane Chemical compound BrC(Br)(Br)C(Br)(Br)C(Br)(Br)C(Br)(Br)Br IGDVFIQVQXDOFA-UHFFFAOYSA-N 0.000 description 1
- ZDUOUNIIAGIPSD-UHFFFAOYSA-N 1,1,1-tribromoethane Chemical compound CC(Br)(Br)Br ZDUOUNIIAGIPSD-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- BASDZFQDZBHCAV-UHFFFAOYSA-N 1,1,1-triiodoethane Chemical compound CC(I)(I)I BASDZFQDZBHCAV-UHFFFAOYSA-N 0.000 description 1
- ZFMWDTNZPKDVBU-UHFFFAOYSA-N 1,2,3,4-tetrachlorocyclopentane Chemical compound ClC1CC(Cl)C(Cl)C1Cl ZFMWDTNZPKDVBU-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 1
- DMRXISNUOWIOKV-UHFFFAOYSA-N 1-bromobutan-2-ol Chemical compound CCC(O)CBr DMRXISNUOWIOKV-UHFFFAOYSA-N 0.000 description 1
- FQJZPYXGPYJJIH-UHFFFAOYSA-N 1-bromonaphthalen-2-ol Chemical compound C1=CC=CC2=C(Br)C(O)=CC=C21 FQJZPYXGPYJJIH-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- FTGLKPMFTLNUBN-UHFFFAOYSA-N 1-chloro-2-iodo-3-methylbenzene Chemical compound CC1=CC=CC(Cl)=C1I FTGLKPMFTLNUBN-UHFFFAOYSA-N 0.000 description 1
- KJESGYZFVCIMDE-UHFFFAOYSA-N 1-chloroethanol Chemical compound CC(O)Cl KJESGYZFVCIMDE-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- IBTLFDCPAJLATQ-UHFFFAOYSA-N 1-prop-2-enoxybutane Chemical compound CCCCOCC=C IBTLFDCPAJLATQ-UHFFFAOYSA-N 0.000 description 1
- UZGKAASZIMOAMU-UHFFFAOYSA-N 124177-85-1 Chemical class NP(=O)=O UZGKAASZIMOAMU-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- HSQFVBWFPBKHEB-UHFFFAOYSA-N 2,3,4-trichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1Cl HSQFVBWFPBKHEB-UHFFFAOYSA-N 0.000 description 1
- RAVQRLMNFPYRSD-UHFFFAOYSA-N 2,3-dihydroxybutanedioyl dibromide Chemical compound BrC(=O)C(O)C(O)C(Br)=O RAVQRLMNFPYRSD-UHFFFAOYSA-N 0.000 description 1
- JODXKZAUFHEYGO-UHFFFAOYSA-N 2,3-dihydroxybutanedioyl dichloride Chemical compound ClC(=O)C(O)C(O)C(Cl)=O JODXKZAUFHEYGO-UHFFFAOYSA-N 0.000 description 1
- PSGUDVJPEWTBRM-UHFFFAOYSA-N 2,4-dibromonaphthalen-1-ol Chemical compound C1=CC=C2C(O)=C(Br)C=C(Br)C2=C1 PSGUDVJPEWTBRM-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- CUEJHYHGUMAGBP-UHFFFAOYSA-N 2-[2-(1h-indol-5-yl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1C1=CC=C(NC=C2)C2=C1 CUEJHYHGUMAGBP-UHFFFAOYSA-N 0.000 description 1
- NCKMMSIFQUPKCK-UHFFFAOYSA-N 2-benzyl-4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1CC1=CC=CC=C1 NCKMMSIFQUPKCK-UHFFFAOYSA-N 0.000 description 1
- MTIDYGLTAOZOGU-UHFFFAOYSA-N 2-bromo-4-methylphenol Chemical compound CC1=CC=C(O)C(Br)=C1 MTIDYGLTAOZOGU-UHFFFAOYSA-N 0.000 description 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- BZWMYDJJDBFAPE-UHFFFAOYSA-N 2-chloro-4-phenylphenol Chemical compound C1=C(Cl)C(O)=CC=C1C1=CC=CC=C1 BZWMYDJJDBFAPE-UHFFFAOYSA-N 0.000 description 1
- NYEWDMNOXFGGDX-UHFFFAOYSA-N 2-chlorocyclohexan-1-ol Chemical compound OC1CCCCC1Cl NYEWDMNOXFGGDX-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- HFHFGHLXUCOHLN-UHFFFAOYSA-N 2-fluorophenol Chemical compound OC1=CC=CC=C1F HFHFGHLXUCOHLN-UHFFFAOYSA-N 0.000 description 1
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- IFVLZKSUYNTRHJ-UHFFFAOYSA-N 2-methylpropyl 2,2-dimethylpropanoate Chemical compound CC(C)COC(=O)C(C)(C)C IFVLZKSUYNTRHJ-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- NMVXHZSPDTXJSJ-UHFFFAOYSA-L 2-methylpropylaluminum(2+);dichloride Chemical compound CC(C)C[Al](Cl)Cl NMVXHZSPDTXJSJ-UHFFFAOYSA-L 0.000 description 1
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- YHCCCMIWRBJYHG-UHFFFAOYSA-N 3-(2-ethylhexoxymethyl)heptane Chemical compound CCCCC(CC)COCC(CC)CCCC YHCCCMIWRBJYHG-UHFFFAOYSA-N 0.000 description 1
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 description 1
- MPCCNXGZCOXPMG-UHFFFAOYSA-N 4-bromobenzene-1,3-diol Chemical compound OC1=CC=C(Br)C(O)=C1 MPCCNXGZCOXPMG-UHFFFAOYSA-N 0.000 description 1
- OSDLLIBGSJNGJE-UHFFFAOYSA-N 4-chloro-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1Cl OSDLLIBGSJNGJE-UHFFFAOYSA-N 0.000 description 1
- JQVAPEJNIZULEK-UHFFFAOYSA-N 4-chlorobenzene-1,3-diol Chemical compound OC1=CC=C(Cl)C(O)=C1 JQVAPEJNIZULEK-UHFFFAOYSA-N 0.000 description 1
- WWOBYPKUYODHDG-UHFFFAOYSA-N 4-chlorocatechol Chemical compound OC1=CC=C(Cl)C=C1O WWOBYPKUYODHDG-UHFFFAOYSA-N 0.000 description 1
- LVSPDZAGCBEQAV-UHFFFAOYSA-N 4-chloronaphthalen-1-ol Chemical compound C1=CC=C2C(O)=CC=C(Cl)C2=C1 LVSPDZAGCBEQAV-UHFFFAOYSA-N 0.000 description 1
- VSMDINRNYYEDRN-UHFFFAOYSA-N 4-iodophenol Chemical compound OC1=CC=C(I)C=C1 VSMDINRNYYEDRN-UHFFFAOYSA-N 0.000 description 1
- VFKIQINEAKWHGO-UHFFFAOYSA-N 4-methylbenzoyl bromide Chemical compound CC1=CC=C(C(Br)=O)C=C1 VFKIQINEAKWHGO-UHFFFAOYSA-N 0.000 description 1
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 1
- KDVYCTOWXSLNNI-UHFFFAOYSA-N 4-t-Butylbenzoic acid Chemical compound CC(C)(C)C1=CC=C(C(O)=O)C=C1 KDVYCTOWXSLNNI-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- DCBJCKDOZLTTDW-UHFFFAOYSA-N 5-chloropentan-1-ol Chemical compound OCCCCCCl DCBJCKDOZLTTDW-UHFFFAOYSA-N 0.000 description 1
- YLDFTMJPQJXGSS-UHFFFAOYSA-N 6-bromo-2-naphthol Chemical compound C1=C(Br)C=CC2=CC(O)=CC=C21 YLDFTMJPQJXGSS-UHFFFAOYSA-N 0.000 description 1
- JVKJKTZQMQSICC-UHFFFAOYSA-N 6-methoxy-6-oxohexanoic acid;hydrochloride Chemical compound Cl.COC(=O)CCCCC(O)=O JVKJKTZQMQSICC-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- RVEGFWPPTBDWOV-UHFFFAOYSA-N CCCCOC(C1=CC=CC=C1C(O)=O)=O.Cl Chemical compound CCCCOC(C1=CC=CC=C1C(O)=O)=O.Cl RVEGFWPPTBDWOV-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- QCZVIXQXGWIBHR-UHFFFAOYSA-N ClC(CCCO[Ti])(Cl)Cl Chemical compound ClC(CCCO[Ti])(Cl)Cl QCZVIXQXGWIBHR-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000004803 Di-2ethylhexylphthalate Substances 0.000 description 1
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 1
- YUXIBTJKHLUKBD-UHFFFAOYSA-N Dibutyl succinate Chemical compound CCCCOC(=O)CCC(=O)OCCCC YUXIBTJKHLUKBD-UHFFFAOYSA-N 0.000 description 1
- LQLQDKBJAIILIQ-UHFFFAOYSA-N Dibutyl terephthalate Chemical compound CCCCOC(=O)C1=CC=C(C(=O)OCCCC)C=C1 LQLQDKBJAIILIQ-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
- AQZGPSLYZOOYQP-UHFFFAOYSA-N Diisoamyl ether Chemical compound CC(C)CCOCCC(C)C AQZGPSLYZOOYQP-UHFFFAOYSA-N 0.000 description 1
- RDOFJDLLWVCMRU-UHFFFAOYSA-N Diisobutyl adipate Chemical compound CC(C)COC(=O)CCCCC(=O)OCC(C)C RDOFJDLLWVCMRU-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- KBEBGUQPQBELIU-CMDGGOBGSA-N Ethyl cinnamate Chemical compound CCOC(=O)\C=C\C1=CC=CC=C1 KBEBGUQPQBELIU-CMDGGOBGSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 238000004615 MNDO calculation Methods 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- FNJSWIPFHMKRAT-UHFFFAOYSA-N Monomethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(O)=O FNJSWIPFHMKRAT-UHFFFAOYSA-N 0.000 description 1
- 101100456571 Mus musculus Med12 gene Proteins 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 208000034177 Self-improving collodion baby Diseases 0.000 description 1
- 241001001836 Talpa stankovici Species 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001334 alicyclic compounds Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 1
- 150000001463 antimony compounds Chemical group 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- MDUYJUQASRFAOG-UHFFFAOYSA-N benzene-1,2-dicarbonyl bromide Chemical compound BrC(=O)C1=CC=CC=C1C(Br)=O MDUYJUQASRFAOG-UHFFFAOYSA-N 0.000 description 1
- FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 description 1
- YAZXITQPRUBWGP-UHFFFAOYSA-N benzene-1,3-dicarbonyl bromide Chemical compound BrC(=O)C1=CC=CC(C(Br)=O)=C1 YAZXITQPRUBWGP-UHFFFAOYSA-N 0.000 description 1
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- AQIHMSVIAGNIDM-UHFFFAOYSA-N benzoyl bromide Chemical compound BrC(=O)C1=CC=CC=C1 AQIHMSVIAGNIDM-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- ONZOGXRINCURBP-NXEZZACHSA-N bis(2-methylpropyl) (2r,3r)-2,3-dihydroxybutanedioate Chemical compound CC(C)COC(=O)[C@H](O)[C@@H](O)C(=O)OCC(C)C ONZOGXRINCURBP-NXEZZACHSA-N 0.000 description 1
- RSRICHZMFPHXLE-AATRIKPKSA-N bis(2-methylpropyl) (e)-but-2-enedioate Chemical compound CC(C)COC(=O)\C=C\C(=O)OCC(C)C RSRICHZMFPHXLE-AATRIKPKSA-N 0.000 description 1
- LKUXNJPSPNDDLI-UHFFFAOYSA-N bis(2-methylpropyl) benzene-1,3-dicarboxylate Chemical compound CC(C)COC(=O)C1=CC=CC(C(=O)OCC(C)C)=C1 LKUXNJPSPNDDLI-UHFFFAOYSA-N 0.000 description 1
- QCOAPBRVQHMEPF-UHFFFAOYSA-N bis(2-methylpropyl) butanedioate Chemical compound CC(C)COC(=O)CCC(=O)OCC(C)C QCOAPBRVQHMEPF-UHFFFAOYSA-N 0.000 description 1
- HMOFGLGHQFZQDS-UHFFFAOYSA-N bis(2-methylpropyl) decanedioate Chemical compound CC(C)COC(=O)CCCCCCCCC(=O)OCC(C)C HMOFGLGHQFZQDS-UHFFFAOYSA-N 0.000 description 1
- UFWRCRCDRAUAAO-UHFFFAOYSA-N bis(2-methylpropyl) pentanedioate Chemical compound CC(C)COC(=O)CCCC(=O)OCC(C)C UFWRCRCDRAUAAO-UHFFFAOYSA-N 0.000 description 1
- SWBJZPDGKVYSLT-UHFFFAOYSA-N bis(2-methylpropyl) propanedioate Chemical compound CC(C)COC(=O)CC(=O)OCC(C)C SWBJZPDGKVYSLT-UHFFFAOYSA-N 0.000 description 1
- WEDLYHNDZPHFLT-UHFFFAOYSA-M bis(2-methylpropyl)-phenoxyalumane Chemical compound [O-]C1=CC=CC=C1.CC(C)C[Al+]CC(C)C WEDLYHNDZPHFLT-UHFFFAOYSA-M 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 229950005228 bromoform Drugs 0.000 description 1
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
- APKYUQFPWXLNFH-UHFFFAOYSA-M butan-1-olate titanium(4+) chloride Chemical compound [Cl-].CCCCO[Ti+](OCCCC)OCCCC APKYUQFPWXLNFH-UHFFFAOYSA-M 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- YVXPOZFNECJRIC-UHFFFAOYSA-N butanedioyl dibromide Chemical compound BrC(=O)CCC(Br)=O YVXPOZFNECJRIC-UHFFFAOYSA-N 0.000 description 1
- IRXBNHGNHKNOJI-UHFFFAOYSA-N butanedioyl dichloride Chemical compound ClC(=O)CCC(Cl)=O IRXBNHGNHKNOJI-UHFFFAOYSA-N 0.000 description 1
- QAWBXZYPFCFQLA-UHFFFAOYSA-N butanoyl bromide Chemical compound CCCC(Br)=O QAWBXZYPFCFQLA-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JOHCVVJGGSABQY-UHFFFAOYSA-N carbon tetraiodide Chemical compound IC(I)(I)I JOHCVVJGGSABQY-UHFFFAOYSA-N 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- VEZNCHDBSQWUHQ-UHFFFAOYSA-N chlorocyclopropane Chemical compound ClC1CC1 VEZNCHDBSQWUHQ-UHFFFAOYSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- AJPXTSMULZANCB-UHFFFAOYSA-N chlorohydroquinone Chemical compound OC1=CC=C(O)C(Cl)=C1 AJPXTSMULZANCB-UHFFFAOYSA-N 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- KBEBGUQPQBELIU-UHFFFAOYSA-N cinnamic acid ethyl ester Natural products CCOC(=O)C=CC1=CC=CC=C1 KBEBGUQPQBELIU-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- OXARPLABDJXAQJ-UHFFFAOYSA-N cyclohexene-1-carbonyl chloride Chemical compound ClC(=O)C1=CCCCC1 OXARPLABDJXAQJ-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- PCYQQSKDZQTOQG-NXEZZACHSA-N dibutyl (2r,3r)-2,3-dihydroxybutanedioate Chemical compound CCCCOC(=O)[C@H](O)[C@@H](O)C(=O)OCCCC PCYQQSKDZQTOQG-NXEZZACHSA-N 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- ISXDVFNOXYQPIA-UHFFFAOYSA-N dibutyl pentanedioate Chemical compound CCCCOC(=O)CCCC(=O)OCCCC ISXDVFNOXYQPIA-UHFFFAOYSA-N 0.000 description 1
- 229960002380 dibutyl phthalate Drugs 0.000 description 1
- 229960002097 dibutylsuccinate Drugs 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- JLVWYWVLMFVCDI-UHFFFAOYSA-N diethyl benzene-1,3-dicarboxylate Chemical compound CCOC(=O)C1=CC=CC(C(=O)OCC)=C1 JLVWYWVLMFVCDI-UHFFFAOYSA-N 0.000 description 1
- ONIHPYYWNBVMID-UHFFFAOYSA-N diethyl benzene-1,4-dicarboxylate Chemical compound CCOC(=O)C1=CC=C(C(=O)OCC)C=C1 ONIHPYYWNBVMID-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical compound CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 description 1
- OUWSNHWQZPEFEX-UHFFFAOYSA-N diethyl glutarate Chemical compound CCOC(=O)CCCC(=O)OCC OUWSNHWQZPEFEX-UHFFFAOYSA-N 0.000 description 1
- YSAVZVORKRDODB-WDSKDSINSA-N diethyl tartrate Chemical compound CCOC(=O)[C@@H](O)[C@H](O)C(=O)OCC YSAVZVORKRDODB-WDSKDSINSA-N 0.000 description 1
- UWAMTZZJXXCIOH-UHFFFAOYSA-M diethyl(phenoxy)alumane Chemical compound CC[Al+]CC.[O-]C1=CC=CC=C1 UWAMTZZJXXCIOH-UHFFFAOYSA-M 0.000 description 1
- JJSGABFIILQOEY-UHFFFAOYSA-M diethylalumanylium;bromide Chemical compound CC[Al](Br)CC JJSGABFIILQOEY-UHFFFAOYSA-M 0.000 description 1
- PPQUYYAZSOKTQD-UHFFFAOYSA-M diethylalumanylium;iodide Chemical compound CC[Al](I)CC PPQUYYAZSOKTQD-UHFFFAOYSA-M 0.000 description 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 1
- 229940031769 diisobutyl adipate Drugs 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- TUTOKIOKAWTABR-UHFFFAOYSA-N dimethylalumane Chemical compound C[AlH]C TUTOKIOKAWTABR-UHFFFAOYSA-N 0.000 description 1
- JGHYBJVUQGTEEB-UHFFFAOYSA-M dimethylalumanylium;chloride Chemical compound C[Al](C)Cl JGHYBJVUQGTEEB-UHFFFAOYSA-M 0.000 description 1
- DWNAQMUDCDVSLT-UHFFFAOYSA-N diphenyl phthalate Chemical compound C=1C=CC=C(C(=O)OC=2C=CC=CC=2)C=1C(=O)OC1=CC=CC=C1 DWNAQMUDCDVSLT-UHFFFAOYSA-N 0.000 description 1
- XOCWTYIVWYOSGQ-UHFFFAOYSA-N dipropylalumane Chemical compound C(CC)[AlH]CCC XOCWTYIVWYOSGQ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- NRHMQDVIKPCCRT-UHFFFAOYSA-N ethanol;titanium Chemical compound [Ti].CCO.CCO.CCO NRHMQDVIKPCCRT-UHFFFAOYSA-N 0.000 description 1
- MNLMLEWXCMFNFO-UHFFFAOYSA-K ethanol;trichlorotitanium Chemical compound CCO.Cl[Ti](Cl)Cl MNLMLEWXCMFNFO-UHFFFAOYSA-K 0.000 description 1
- MNFTYNIMQNJVJI-UHFFFAOYSA-N ethoxy(dipropyl)alumane Chemical compound CC[O-].CCC[Al+]CCC MNFTYNIMQNJVJI-UHFFFAOYSA-N 0.000 description 1
- XGAIERUWZADBAO-UHFFFAOYSA-N ethoxy-bis(2-methylpropyl)alumane Chemical compound CCO[Al](CC(C)C)CC(C)C XGAIERUWZADBAO-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- LIQWHXBLFOERRD-UHFFFAOYSA-N ethyl 4-tert-butylbenzoate Chemical compound CCOC(=O)C1=CC=C(C(C)(C)C)C=C1 LIQWHXBLFOERRD-UHFFFAOYSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- JJOYCHKVKWDMEA-UHFFFAOYSA-N ethyl cyclohexanecarboxylate Chemical compound CCOC(=O)C1CCCCC1 JJOYCHKVKWDMEA-UHFFFAOYSA-N 0.000 description 1
- XCTLDQQOHIEUCJ-UHFFFAOYSA-N ethyl naphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OCC)=CC=CC2=C1 XCTLDQQOHIEUCJ-UHFFFAOYSA-N 0.000 description 1
- NARCMUVKZHPJHP-UHFFFAOYSA-L ethyl(diiodo)alumane Chemical compound [I-].[I-].CC[Al+2] NARCMUVKZHPJHP-UHFFFAOYSA-L 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- JLYXXMFPNIAWKQ-GNIYUCBRSA-N gamma-hexachlorocyclohexane Chemical compound Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl JLYXXMFPNIAWKQ-GNIYUCBRSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229940093920 gynecological arsenic compound Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- CAYGQBVSOZLICD-UHFFFAOYSA-N hexabromobenzene Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1Br CAYGQBVSOZLICD-UHFFFAOYSA-N 0.000 description 1
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 description 1
- VUNCWTMEJYMOOR-UHFFFAOYSA-N hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-UHFFFAOYSA-N 0.000 description 1
- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 1
- VFDYKPARTDCDCU-UHFFFAOYSA-N hexachloropropene Chemical group ClC(Cl)=C(Cl)C(Cl)(Cl)Cl VFDYKPARTDCDCU-UHFFFAOYSA-N 0.000 description 1
- UJGPNLWJDSIACI-UHFFFAOYSA-N hexanedioyl dibromide Chemical compound BrC(=O)CCCCC(Br)=O UJGPNLWJDSIACI-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- JCYWCSGERIELPG-UHFFFAOYSA-N imes Chemical compound CC1=CC(C)=CC(C)=C1N1C=CN(C=2C(=CC(C)=CC=2C)C)[C]1 JCYWCSGERIELPG-UHFFFAOYSA-N 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 229960002809 lindane Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- YSMZEMQBSONIMJ-UHFFFAOYSA-M magnesium;2-methanidylpropane;chloride Chemical compound [Mg+2].[Cl-].CC(C)[CH2-] YSMZEMQBSONIMJ-UHFFFAOYSA-M 0.000 description 1
- CQRPUKWAZPZXTO-UHFFFAOYSA-M magnesium;2-methylpropane;chloride Chemical compound [Mg+2].[Cl-].C[C-](C)C CQRPUKWAZPZXTO-UHFFFAOYSA-M 0.000 description 1
- NIXOIRLDFIPNLJ-UHFFFAOYSA-M magnesium;benzene;bromide Chemical compound [Mg+2].[Br-].C1=CC=[C-]C=C1 NIXOIRLDFIPNLJ-UHFFFAOYSA-M 0.000 description 1
- QUXHCILOWRXCEO-UHFFFAOYSA-M magnesium;butane;chloride Chemical compound [Mg+2].[Cl-].CCC[CH2-] QUXHCILOWRXCEO-UHFFFAOYSA-M 0.000 description 1
- YHNWUQFTJNJVNU-UHFFFAOYSA-N magnesium;butane;ethane Chemical compound [Mg+2].[CH2-]C.CCC[CH2-] YHNWUQFTJNJVNU-UHFFFAOYSA-N 0.000 description 1
- DLPASUVGCQPFFO-UHFFFAOYSA-N magnesium;ethane Chemical compound [Mg+2].[CH2-]C.[CH2-]C DLPASUVGCQPFFO-UHFFFAOYSA-N 0.000 description 1
- YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- BQBCXNQILNPAPX-UHFFFAOYSA-N methoxy(dimethyl)alumane Chemical compound [O-]C.C[Al+]C BQBCXNQILNPAPX-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical compound COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000004219 molecular orbital method Methods 0.000 description 1
- NKHAVTQWNUWKEO-NSCUHMNNSA-N monomethyl fumarate Chemical compound COC(=O)\C=C\C(O)=O NKHAVTQWNUWKEO-NSCUHMNNSA-N 0.000 description 1
- 229940005650 monomethyl fumarate Drugs 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 125000005487 naphthalate group Chemical group 0.000 description 1
- NSNPSJGHTQIXDO-UHFFFAOYSA-N naphthalene-1-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=CC=CC2=C1 NSNPSJGHTQIXDO-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- AJYOOHCNOXWTKJ-UHFFFAOYSA-N p-Chlorobenzhydrol Chemical compound C=1C=C(Cl)C=CC=1C(O)C1=CC=CC=C1 AJYOOHCNOXWTKJ-UHFFFAOYSA-N 0.000 description 1
- BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 description 1
- PHLZDCSVSDSPPH-UHFFFAOYSA-N pentanedioyl dibromide Chemical compound BrC(=O)CCCC(Br)=O PHLZDCSVSDSPPH-UHFFFAOYSA-N 0.000 description 1
- YVOFTMXWTWHRBH-UHFFFAOYSA-N pentanedioyl dichloride Chemical compound ClC(=O)CCCC(Cl)=O YVOFTMXWTWHRBH-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229960003857 proglumide Drugs 0.000 description 1
- VWQXLMJSFGLQIT-UHFFFAOYSA-N prop-2-enoyl bromide Chemical compound BrC(=O)C=C VWQXLMJSFGLQIT-UHFFFAOYSA-N 0.000 description 1
- GLFSWJDJMXUVEV-UHFFFAOYSA-N prop-2-enoyl iodide Chemical compound IC(=O)C=C GLFSWJDJMXUVEV-UHFFFAOYSA-N 0.000 description 1
- SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- QMKUYPGVVVLYSR-UHFFFAOYSA-N propyl 2,2-dimethylpropanoate Chemical compound CCCOC(=O)C(C)(C)C QMKUYPGVVVLYSR-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 208000003665 self-healing collodion baby Diseases 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- FRBIXZIRQKZWGN-UHFFFAOYSA-N tetraethyl benzene-1,2,4,5-tetracarboxylate Chemical compound CCOC(=O)C1=CC(C(=O)OCC)=C(C(=O)OCC)C=C1C(=O)OCC FRBIXZIRQKZWGN-UHFFFAOYSA-N 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、ポリα−オレフィンの製造法に関し、特にメ
ルトフローレートが50以上の高溶融流動性のポリα−
オレフィンの製造法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing polyα-olefin, and particularly to a method for producing polyα-olefin with a melt flow rate of 50 or more.
Concerning a method for producing olefins.
従来の技術
マグネシウム、チタン、ハロゲン及び電子供与性化合物
を含有する成分を主触媒としてポリα−オレフィンを製
造する場合、有機アルミニウム化合物と共に、有機珪素
化合物を用いると生成するポリマーの立体規則性が向上
する。しかしながら、同時に触媒の重合活性の低下を引
き起こす。立体規則性を向上させる度合及び重合活性を
低下させる割合は、用いる珪素化合物の種類により大き
くことなる。一般に芳香族基を有する珪素化合物は、良
好な性能を示すが、ことがある。Conventional technology When producing polyα-olefin using a component containing magnesium, titanium, halogen, and an electron-donating compound as the main catalyst, using an organosilicon compound together with an organoaluminum compound improves the stereoregularity of the resulting polymer. do. However, at the same time, this causes a decrease in the polymerization activity of the catalyst. The degree to which stereoregularity is improved and the rate to which polymerization activity is reduced vary greatly depending on the type of silicon compound used. Generally, silicon compounds having aromatic groups show good performance, but there are cases where silicon compounds have good performance.
一方、ポリマーの溶融流動性を向上するために、一般に
水素によりポリマーのメルトフローレイトを高める方法
が採用されているが、この方法ではポリマーの立体規則
性が低下するのが通常である。On the other hand, in order to improve the melt flowability of a polymer, a method is generally adopted in which the melt flow rate of the polymer is increased using hydrogen, but this method usually reduces the stereoregularity of the polymer.
最近、(A)マグネシウム化合物、チタン化合物及び多
価カルボン酸エステルを接触させることによって形成さ
れるマグネシウム、チタン、ハロゲン及び多価カルボン
酸エステルを必須成分として含有する固体チタン触媒成
分、(B)有機アルミニウム化合物触媒成分、(C)一
般式SiR’、(OR”)=−、で表わされる有機珪素
化合物触媒成分、から形成される触媒系の存在下に、M
FRが10g/10分以上のプロピレンブロック共重合
体を製造する方法が提案されている(特開昭63−27
517号公報)。Recently, (A) a solid titanium catalyst component containing as essential components magnesium, titanium, a halogen, and a polyvalent carboxylic acid ester formed by contacting a magnesium compound, a titanium compound, and a polyvalent carboxylic acid ester; (B) an organic In the presence of a catalyst system formed from an aluminum compound catalyst component, (C) an organosilicon compound catalyst component represented by the general formula SiR', (OR")=-, M
A method for producing a propylene block copolymer with an FR of 10 g/10 min or more has been proposed (Japanese Patent Laid-Open No. 63-27
Publication No. 517).
しかし、この方法は、特定のプロピレンブロック共重合
体の製造法であり、得られる共重合体のMFRも40g
/10分未満迄の実施例しか存在しない。However, this method is a method for producing a specific propylene block copolymer, and the MFR of the resulting copolymer is also 40g.
/ There are only examples in which the time is less than 10 minutes.
又、上記特開昭63−27517号公報に記載されてい
る(^)成分、(B)成分及び(C)一般式SiR’R
’(OR’)2で表わされる有機珪素化合物触媒成分、
から形成される触媒の存在下に、オレフィンを重合もし
くは共重合させる方法も知られており(特開昭63−2
23008号公報)、この方法においては、水素により
重合体のメルトフローレートを変えても、ポリマーの立
体規則性の低下が少ないとしている。しかし、この方法
では、実質的に用いられている有機珪素化合物はメトキ
シ基含有珪素化合物であり、又得られるポリマーのMF
Rも40g/10分未満である。In addition, the (^) component, (B) component and (C) general formula SiR'R described in the above-mentioned Japanese Patent Application Laid-Open No. 63-27517
An organosilicon compound catalyst component represented by '(OR')2,
A method of polymerizing or copolymerizing olefins in the presence of a catalyst formed from
No. 23008), in this method, even if the melt flow rate of the polymer is changed by hydrogen, the stereoregularity of the polymer is said to be less degraded. However, in this method, the organic silicon compound essentially used is a methoxy group-containing silicon compound, and the MF of the resulting polymer is
R is also less than 40 g/10 minutes.
発明が解決しようとする課題
本発明は、水素によるメルトフローレートへの作用効果
(すなわち、水素リスポンス)が良好で、しかもポリマ
ーの立体規則性の低下が少ない有機珪素化合物を組み合
せた触媒を用いた高溶融流動性のポリα−オレフィンを
高収率で得る方法を提供することを目的とする。Problems to be Solved by the Invention The present invention uses a catalyst in combination with an organosilicon compound that has a good effect on the melt flow rate due to hydrogen (i.e., hydrogen response) and less decreases in the stereoregularity of the polymer. It is an object of the present invention to provide a method for obtaining a poly-α-olefin with high melt fluidity in high yield.
課題を解決するための手段
本発明者らは、有機珪素化合物を一成分とした重合触媒
を用いたα−オレフィンの重合法について鋭意研究を行
った結果、分子の体積が成る程度大きく、しかもエトキ
シ基の酸素原子の電子密度が特定の範囲のエトキシ基含
有シラン化合物を、−成分とした特定の重合触媒が、高
活性を示し、高立体規則性のポリα−オレフィンを製造
可能であり、しかも水素リスポンスが良好で、多量の水
素を用いても立体規則性の低・下が僅少であることを見
出して本発明を完成した。Means for Solving the Problems The present inventors have conducted intensive research on a method for polymerizing α-olefins using a polymerization catalyst containing an organosilicon compound as one component. A specific polymerization catalyst containing an ethoxy group-containing silane compound in which the electron density of the oxygen atom of the group is in a specific range exhibits high activity and can produce polyα-olefins with high stereoregularity. The present invention was completed based on the discovery that the hydrogen response is good and that even when a large amount of hydrogen is used, there is only a slight decrease in stereoregularity.
発明の要旨
すなわち、本発明は、
(A)金属酸化物、マグネシウム、チタン、ハロゲン及
び電子供与性化合物を必須成分とする固体触媒成分、
(B)有機金属化合物及び
(C)一般式R,,Sl (OC2H−) −−−(但
し、Rは炭素数3〜10個の脂肪族炭化水素基、nはl
又は2である。〕で表わされ、量子化学計算で算出した
体積が200〜500A’、同じくエトキシ基の酸素原
子の電子密度が0.680〜0.800A、U、 (ア
トミックユニット)のエトキシ基含有シラン化合物
とからなる触媒の存在下、α−オレフィンを重合するこ
とからなるポリα−オレフィンの製造法を要旨とする。Summary of the Invention That is, the present invention comprises: (A) a solid catalyst component containing a metal oxide, magnesium, titanium, halogen, and an electron-donating compound as essential components; (B) an organometallic compound; and (C) a general formula R. Sl (OC2H-)---(However, R is an aliphatic hydrocarbon group having 3 to 10 carbon atoms, n is l
Or 2. ], the volume calculated by quantum chemical calculation is 200 to 500 A', and the electron density of the oxygen atom of the ethoxy group is 0.680 to 0.800 A, U, (atomic unit). The gist of the invention is a method for producing a poly-α-olefin, which comprises polymerizing an α-olefin in the presence of a catalyst comprising:
固体触媒成分
本発明で用いられる触媒の一成分である固体触媒成分(
以下、成分Aという)は、金属酸化物、マグネシウム、
チタン、ハロゲン及び電子供与性化合物を必須成分とす
るが、このような成分は通常金属酸化物、マグネシウム
化合物、チタン化合物及び電子供与性化合物、更に前記
各化合物がハロゲンを有しない化合物の場合は、ハロゲ
ン含有化合物を、それぞれ接触することにより調製され
る。Solid catalyst component A solid catalyst component (which is one component of the catalyst used in the present invention)
Hereinafter, component A) is a metal oxide, magnesium,
Titanium, a halogen, and an electron-donating compound are essential components, but such components are usually metal oxides, magnesium compounds, titanium compounds, and electron-donating compounds, and if each of the above compounds does not have a halogen, It is prepared by contacting halogen-containing compounds, respectively.
(1〕金属酸化物
本発明で用いられる金属酸化物は、元素の周期表第■族
〜第■族の元素の群から選ばれる元素の酸化物であり、
それらを例示すると、B、03、MgO、A 12 Q
s S i、o 2 、 CaOTiO
2,2nO1ZrO,、SnO2、Ban Th0
z等が挙げられる。これらの中でもB201、MgO1
AI20a、S+02、TI[+2、Z「0.が望まし
く、特にSiLが望ましい。更に、これら金属酸化物を
含む複合酸化物、例えばS+Oz−MgO1SiOz−
Ah[ls、5i02−TiQa、5iOz−V20s
SiL−Cr2wls、Si0S102−TiO
z−等も使用し得る。(1) Metal oxide The metal oxide used in the present invention is an oxide of an element selected from the group of elements of Groups 1 to 2 of the Periodic Table of Elements,
To illustrate them, B, 03, MgO, A 12 Q
s S i, o 2 , CaOTiO
2,2nO1ZrO,, SnO2, Ban Th0
Examples include z. Among these, B201, MgO1
AI20a, S+02, TI[+2, Z"0. is desirable, and SiL is particularly desirable. Furthermore, composite oxides containing these metal oxides, such as S+Oz-MgO1SiOz-
Ah [ls, 5i02-TiQa, 5iOz-V20s
SiL-Cr2wls, Si0S102-TiO
z-, etc. may also be used.
これら金属酸化物の形状は通常粉末状のものが用いられ
る。粉末の大きさ及び形状等の形体は、得られるオレフ
ィン重合体の形体に影響を及ぼすことが多いので、適宜
調節することが望ましい。金属酸化物は、使用に当って
被毒物質を除去する目的等から、可能な限り高温で焼成
し、更に大気と直接接触しないように取扱うのが望まし
い。These metal oxides are usually in the form of powder. The size and shape of the powder often affect the shape of the obtained olefin polymer, so it is desirable to adjust it appropriately. For the purpose of removing poisonous substances before use, it is desirable to sinter metal oxides at as high a temperature as possible, and to handle them in a manner that prevents them from coming into direct contact with the atmosphere.
(2)マグネシウム化合物
マグネシウム化合物は、一般弐MgR’R”で表わされ
る。式において、R’及びR2は同一か異なる炭化水素
基、OR基(Rは炭化水素基) ハロゲン原子を示す。(2) Magnesium Compound A magnesium compound is generally represented by MgR'R''. In the formula, R' and R2 are the same or different hydrocarbon groups, OR group (R is a hydrocarbon group) and represent a halogen atom.
より詳細には、11′及びR2の炭化水素基としては、
炭素数l〜20個のアルキル基、シクロアルキル基、ア
リール基、アルアルキル基が、OR基としては、Rが炭
素数1−12個のアルキル基、シクロアルキル基、アリ
ール基、アルアルキル基が、ハロゲン原子としては塩素
、臭素、ヨウ素、弗素等である。More specifically, the hydrocarbon groups of 11' and R2 are:
As the OR group, R is an alkyl group, cycloalkyl group, aryl group, or aralkyl group having 1 to 20 carbon atoms; , halogen atoms include chlorine, bromine, iodine, fluorine, etc.
それら化合物の具体例を下記に示すが、化学式において
、Me:メチル、Bt:エチル、Pr:プロピル、Bu
ニブチル、He:ヘキシル、Oct :オクチル、Ph
:フェニル、cylleニジクロヘキシルをそれぞれ示
す。Specific examples of these compounds are shown below, and in the chemical formula, Me: methyl, Bt: ethyl, Pr: propyl, Bu
Nibutyl, He: hexyl, Oct: octyl, Ph
: Indicates phenyl and cylle dichlorohexyl, respectively.
MgMez 、 MgBt2. Mg1−Prz 、
MgBu2. Mg1le2゜MgDct* 、 Mg
BtBu 、 MgPh2. Mg1le2 。MgMez, MgBt2. Mg1-Prz,
MgBu2. Mg1le2゜MgDct*, Mg
BtBu, MgPh2. Mg1le2.
Mg(QMe)2. Mg(OBt)z 、 Mg(O
Bu)z、 Mg([1He)2゜Mg(00ct)z
、 Mg(OPhL 、 Mg((]cyHe)z
。Mg(QMe)2. Mg(OBt)z, Mg(O
Bu)z, Mg([1He)2゜Mg(00ct)z
, Mg(OPhL , Mg((]cyHe)z
.
BtMgCl 、 BuMgCl 、 tleMgcl
、 i−BuMgCl 、 t−ロuMgC1、P
hMgC1、PhClI2MgCl 、 BtMg
Br 。BtMgCl, BuMgCl, tleMgcl
, i-BuMgCl, t-BuMgCl, P
hMgC1, PhClI2MgCl, BtMg
Br.
[]uMgBr 、 PhMgBr 、 BuMgl
、 BtOMgCI 。[]uMgBr, PhMgBr, BuMgl
, BtOMgCI.
tlluOMgcl 、 He0MgCl 、 Ph0
MgCl 、 BtOMgBr 。tlluOMgcl, He0MgCl, Ph0
MgCl, BtOMgBr.
BuOMgBr 、BtOMgl 、MgCl2
、MgBrz 、MgL 。BuOMgBr, BtOMgl, MgCl2
, MgBrz, MgL.
上記マグネシウム化合物は、成分Aを調製する際に、金
属マグネシウム又はその他のマグネシウム化合物から調
製することも可能である。The above magnesium compound can also be prepared from metallic magnesium or other magnesium compounds when preparing component A.
その−例として、金属マグネシウム、ハロゲン化炭化水
素及び一般式XhM(OR)、、のアルコキシ基含有化
合物〔式において、Xは水素原子、ハロゲン原子又は炭
素数1〜20個の炭化水素基、Mは硼素、炭素、アルミ
ニウム、珪素又は燐原子、Rは炭素数1〜20個の炭化
水素基、mはMの原子価、man≧0を示す。〕を接触
させる方法が挙げられる。該アルコキシ基含有化合物の
一般式のX及びRの炭化水素基としては、メチル(Me
) エチル(Bt) プロピル(Pr)、i−プロ
ピル(1−Pr) ブチル(8u) 、’j−ブチル
(1−Bu) ヘキシル(He) オクチル(0c
t) 等のアルキル基、シクロヘキシル(cyHe)
メチルシクロヘキシル等のシクロアルキル基、アリル
、プロペニル、ブテニル等のアルケニル基、フェニル(
Ph) )IJル、キシリル基のアリール基、フェ
ネチル、3−フェニルプロピル等のアルアルキル等が挙
げられる。Examples thereof include metallic magnesium, halogenated hydrocarbons, and alkoxy group-containing compounds of the general formula represents a boron, carbon, aluminum, silicon or phosphorus atom, R represents a hydrocarbon group having 1 to 20 carbon atoms, m represents the valence of M, and man≧0. ] is mentioned. The hydrocarbon groups represented by X and R in the general formula of the alkoxy group-containing compound include methyl (Me
) Ethyl (Bt) Propyl (Pr), i-propyl (1-Pr) Butyl (8u), 'j-butyl (1-Bu) Hexyl (He) Octyl (0c
t) alkyl groups such as cyclohexyl (cyHe)
Cycloalkyl groups such as methylcyclohexyl, alkenyl groups such as allyl, propenyl, butenyl, phenyl (
Ph)) IJ, aryl groups such as xylyl groups, and aralkyl groups such as phenethyl and 3-phenylpropyl.
これらの中でも、特に炭素数1〜10個のアルキル基が
望ましい。以下、アルコキシ基含有化合物の具体例を挙
げる。Among these, alkyl groups having 1 to 10 carbon atoms are particularly desirable. Specific examples of alkoxy group-containing compounds are listed below.
0Mが炭素の場合の化合物
式C(OR)、に含まれる C(OMe)< 、 C(
OBt−)< 。When 0M is carbon, C(OMe)< , C(
OBt-)<.
C(OPr)i 、 C(OBu)< 、 C
(01−BLI)4 、 C(口He)<。C(OPr)i, C(OBu)<, C
(01-BLI) 4, C (mouth He)<.
C(00ct) a ’ 式 XC(OR)、に含ま
れるIC(OMe) s。C(00ct) a' IC(OMe) s contained in the formula XC(OR).
11C(口Bt)s 、 HC(OPr)a 、
HC(OBU)3 、 HC(OMa)3
。11C(mouthBt)s, HC(OPr)a,
HC(OBU)3, HC(OMa)3
.
11c(OPh)s ; MeC(OMa)s
、 MeC(口at)s 、 BtC(OMe)
j。11c(OPh)s; MeC(OMa)s
, MeC(mouth at)s, BtC(OMe)
j.
已tC(OBt)a 、 cyHec((]OBts
、 PhC(OMe)s 。已tC(OBt)a, cyHec((]OBts
, PhC(OMe)s.
PhC(OBt)s 、 CLCIC(Oat)a 、
MeCHBrC(OBt)s、MeCtlCIC(口
Bt)a ; CIC(OMe)s 、 [’
IC(OBtL 。PhC(OBt)s, CLCIC(Oat)a,
MeCHBrC(OBt)s, MeCtlCIC(mouthBt)a; CIC(OMe)s, ['
IC(OBtL.
CIC(Di−Bu)a 、 BrC(OBtL ;式
X、C(OR)、に含まれるMaCtl(OMe)z
、 MeCH(Of!t)i 、 C112C112(
O。CIC(Di-Bu)a, BrC(OBtL; MaCtl(OMe)z contained in formula X, C(OR),
, MeCH(Of!t)i, C112C112(
O.
C)+2(口Bt)i 、 CLCICH(OBt
)z 、 CHCl*CII(OBt)2 。C)+2(mouthBt)i, CLCICH(OBt
)z, CHCl*CII(OBt)2.
CC1,C!((OBt)z 、 C11aBrCH(
OBt)2. PhCH([)Bt)i。CC1,C! ((OBt)z, C11aBrCH(
OBt)2. PhCH([)Bt)i.
■Mが珪素の場合の化合物
式5i(OR)<に含まれる Si(OMe)1. 5
i(OBt)*。■When M is silicon, Si(OMe) included in the compound formula 5i(OR)<1. 5
i(OBt)*.
5i(OBu)* 、 5i(Di−Bu)a 、 5
i(DI!a)< 。5i(OBu)*, 5i(Di-Bu)a, 5
i(DI!a)<.
5i(00ct)4.5i(OPh)a : 式XS
i (OR) s ニ含まれる)ISi(OBt)a
、 ll5i(OBu)s 、 flsi(OH
a)、。5i(00ct)4.5i(OPh)a: Formula XS
i (OR) s d)ISi(OBt)a
, ll5i(OBu)s, flsi(OH
a).
tlsi(OPh)a ; MeSi(OMe)s
、 MeSi(OBt):、 。tlsi(OPh)a ; MeSi(OMe)s
, MeSi(OBt):, .
MeSi(OBu)3. BtSi(OBt)a 、
Ph5i(OBt)a 。MeSi(OBu)3. BtSi(OBt)a,
Ph5i(OBt)a.
BtSi(OPh)s ; CISiCl5i(O
、Cl5i(OBt)3゜Cl5i(OBu)s 、
Cl5i(OPh)3. [1rSi(OBtL ;式
%式%)
):
)
■Mが硼素の場合の化合物
弐B (OR) 3に含まれるB(OBtL 、 B(
081)3 。BtSi(OPh)s; CISiCl5i(O
, Cl5i(OBt)3゜Cl5i(OBu)s,
Cl5i(OPh)3. [1rSi(OBtL; formula%formula%) ): ) ■B contained in compound 2B (OR) 3 when M is boron (OBtL, B(
081)3.
13(Dtle)3. B(OPh)、。13(Dtle)3. B (OPh).
■Mがアルミニウムの場合の化合物
式AI(OR)3に含まれるAI(OMe)s 、 A
I(OBt)s 。■AI(OMe)s, A contained in the compound formula AI(OR)3 when M is aluminum
I(OBt)s.
A1(OPr)s 、 AI(Oi−Pr)s
、 AI(口Bu)3゜AI (Ot−Bu) s
、A1(Otle)s 、 AI(OPh)、。A1(OPr)s, AI(Oi-Pr)s
, AI(口Bu)3゜AI(Ot-Bu)s
, A1(Otle)s, AI(OPh),.
■Mが燐の場合の化合物
弐P(OR)、に含まれるP(OMa)s 、 P(O
[!t)! 。■When M is phosphorus, P(OMa)s, P(O
[! t)! .
P (OBu) −、P (OHe) ! 、 P (
(]Ph) a。P (OBu) −, P (OHe)! , P (
(]Ph) a.
更に、前記マグネシウム化合物は、周期表第■族又は第
1IIa族金属(M)の有機化合物との錯体も使用する
ことができる。該錯体は一般式MgR’R2・n(Mn
2.)で表わされる。該金属としては、アルミニウム、
亜鉛、カルシウム等であり、R3は炭素数1〜12個の
アルキル基、シクロアルキル基、アリール基、アルアル
キル基である。Further, as the magnesium compound, a complex with an organic compound of a metal (M) of Group 1 or Group 1IIa of the periodic table can also be used. The complex has the general formula MgR'R2.n(Mn
2. ). The metal includes aluminum,
Zinc, calcium, etc., and R3 is an alkyl group, cycloalkyl group, aryl group, or aralkyl group having 1 to 12 carbon atoms.
又、mは金属Mの原子価を、nは0,1〜10の数を示
す。Mn2.で表わされる化合物の具体例としては、A
IMes 、 AIBta 、 A11−Bus 、
AlPh、。Further, m represents the valence of the metal M, and n represents a number of 0, 1 to 10. Mn2. Specific examples of compounds represented by A
IMes, AIBta, A11-Bus,
AlPh,.
ZnMe、 、 ZnBt、 、 ZnBu2. Zn
Ph2. Cart、 。ZnMe, , ZnBt, , ZnBu2. Zn
Ph2. Cart.
CaPh2等が挙げられる。Examples include CaPh2.
(2)チタン化合物
チタン化合物は、二価、三価及び四価のチタンの化合物
であり、それらを例示すると、四塩化チタン、四臭化チ
タン、トリクロルエトキシチタン、トリクロルブトキシ
チタン、ジクロルジェトキシチタン、ジクロルジブトキ
シチタン、ジクロルジフェノキシチタン、り0ルトリエ
トキシチタン、クロルトリブトキシチタン、テトラブト
キシチタン、三塩化チタン等を挙げることができる。こ
れらの中でも、四塩化チタン、トリクロルエトキシチタ
ン、ジクロルジブトキシチタン、ジクロルジフェノキシ
チタン等の四価のチタンハロゲン化物が望ましく、特に
四塩化チタンが望ましい。(2) Titanium compounds Titanium compounds are divalent, trivalent, and tetravalent titanium compounds, and examples thereof include titanium tetrachloride, titanium tetrabromide, trichloroethoxytitanium, trichlorobutoxytitanium, and dichlorjetoxytitanium. , dichlordibutoxytitanium, dichlordiphenoxytitanium, triethoxytitanium, chlortributoxytitanium, tetrabutoxytitanium, titanium trichloride, and the like. Among these, tetravalent titanium halides such as titanium tetrachloride, trichlorethoxytitanium, dichlorodibutoxytitanium, and dichlordiphenoxytitanium are preferred, and titanium tetrachloride is particularly preferred.
(3)電子供与性化合物
電子供与性化合物としては、カルボン酸類、カルボン酸
無水物、カルボン酸エステル類、カルホン酸ハロゲン化
物、アルコール類、エーテル類、ケトン類、アミン類、
アミド類、ニトリル類、アルデヒド類、アルコレート類
、有機基と炭素もしくは酸素を介して結合した燐、ヒ素
およびアンチモン化合物、ホスホアミド類、チオエーテ
ル類、チオエステル類、炭酸エステル等が挙げられる。(3) Electron-donating compounds Examples of electron-donating compounds include carboxylic acids, carboxylic anhydrides, carboxylic esters, carbonic acid halides, alcohols, ethers, ketones, amines,
Examples include amides, nitriles, aldehydes, alcoholates, phosphorus, arsenic and antimony compounds bonded to organic groups via carbon or oxygen, phosphoamides, thioethers, thioesters, carbonic esters and the like.
これのうちカルボン酸類、カルボン酸無水物、カルボン
酸エステル類、カルボン酸ハロゲン化物、アルコール類
、エーテル類が好ましく用いられる。Among these, carboxylic acids, carboxylic anhydrides, carboxylic esters, carboxylic halides, alcohols, and ethers are preferably used.
カルボン酸の具体例としては、ギ酸、酢酸、プロピオン
酸、酪酸、イソ酪酸、吉草酸、カプロン酸、ピバリン酸
、アクリル酸、メタクリル酸、クロトン酸等の脂肪族モ
ノカルボン酸、マロン酸、コハク酸、グルタル酸、アジ
ピン酸、セバシン酸、マレイン酸、フマル酸等の脂肪族
ジカルボン酸、酒石酸等の脂肪族オキシカルボン酸、シ
クロへ牛サンモノカルボン酸、シクロヘキセンモノカル
ボン酸、シス−1,2−シクロへ牛サンジカルボン酸、
シス−4−メチルシクロヘキセン−1,2−ジカルボン
酸等の脂環式カルボン酸、安息香酸、トルイル酸、アニ
ス酸、p−第三級ブチル安息香酸、ナフトエ酸、ケイ皮
酸等の芳香族モノカルボン酸、フタル酸、イソフタル酸
、テレフタル酸、ナフタル酸、トリメリド酸、ヘミメリ
ト酸、トリメシン酸、ビロメIJ )酸、メリト酸等の
芳香族多価カルボン酸等が挙げられる。Specific examples of carboxylic acids include aliphatic monocarboxylic acids such as formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, caproic acid, pivalic acid, acrylic acid, methacrylic acid, and crotonic acid, malonic acid, and succinic acid. , aliphatic dicarboxylic acids such as glutaric acid, adipic acid, sebacic acid, maleic acid, fumaric acid, aliphatic oxycarboxylic acids such as tartaric acid, cyclohexene monocarboxylic acid, cyclohexene monocarboxylic acid, cis-1,2- cyclohe bovine dicarboxylic acid,
Alicyclic carboxylic acids such as cis-4-methylcyclohexene-1,2-dicarboxylic acid, aromatic monomers such as benzoic acid, toluic acid, anisic acid, p-tert-butylbenzoic acid, naphthoic acid, and cinnamic acid. Examples include aromatic polycarboxylic acids such as carboxylic acid, phthalic acid, isophthalic acid, terephthalic acid, naphthalic acid, trimellidic acid, hemimellitic acid, trimesic acid, bilometic acid, and mellitic acid.
カルボン酸無水物としては、上記のカルボン酸類の酸無
水物が使用し得る。As the carboxylic acid anhydride, acid anhydrides of the above-mentioned carboxylic acids can be used.
カルボン酸エステルとしては、上記のカルボン酸類のモ
ノ又は多価エステルが使用することができ、その具体例
として、ギ酸ブチル、酢酸エチル、酢酸ブチル、イソ酪
酸イソブチル、ピバリン酸プロピル、ピバリン酸イソブ
チル、アクリル酸エチル、メタクリル酸メチル、メタク
リル酸エチル、メタクリル酸イソブチル、マロン酸ジエ
チル、マロン酸ジイソブチル、コハク酸ジエチル、コハ
ク酸ジブチル、コハク酸ジイソブチル、グルタル酸ジエ
チル、グルタル酸ジブチル、グルタル酸ジイソブチル、
アジピン酸ジイソブチル、セバシン酸ジブチル、セバシ
ン酸ジイソブチル、マレイン酸ジエチル、マレイン酸ジ
ブチル、マレイン酸ジイソブチル、フマル酸モノメチル
、フマル酸ジエチル、フマル酸ジイソブチル、酒石酸ジ
エチル、酒石酸ジブチル、酒石酸ジイソブチル、シクロ
ヘキサンカルボン酸エチル、安息香酸メチル、安息香酸
エチル、p−)ルイル酸メチル、p−第三級ブチル安息
tF 酸エチル、p−アニス酸エチル、α−ナフトエ酸
エチル、α−ナフトエ酸イソブチル、ケイ皮酸エチル、
フタル酸モノメチル、フタル酸モノブチル、フタル酸ジ
ブチル、フタル酸ジイソブチル、フタル酸ジヘキシル、
フタル酸ジオクチル、フタル酸ジ2−エチルヘキシル、
フタル酸ジアリル、フタル酸ジフェニル、イソフタル酸
ジエチル、イソフタル酸ジイソブチル、テレフタル酸ジ
エチル、テレフタル酸ジブチル、ナフタル酸ジエチル、
ナフタル酸ジブチル、トリメリド酸トリエチル、トリメ
リド酸トリブチル、ピロメリト酸テトラメチル、ピロメ
リト酸テトラエチル、ピロメリト酸テトラブチル等が挙
げられる。As the carboxylic acid ester, mono- or polyvalent esters of the above-mentioned carboxylic acids can be used, and specific examples thereof include butyl formate, ethyl acetate, butyl acetate, isobutyl isobutyrate, propyl pivalate, isobutyl pivalate, acrylic. Ethyl acid, methyl methacrylate, ethyl methacrylate, isobutyl methacrylate, diethyl malonate, diisobutyl malonate, diethyl succinate, dibutyl succinate, diisobutyl succinate, diethyl glutarate, dibutyl glutarate, diisobutyl glutarate,
Diisobutyl adipate, dibutyl sebacate, diisobutyl sebacate, diethyl maleate, dibutyl maleate, diisobutyl maleate, monomethyl fumarate, diethyl fumarate, diisobutyl fumarate, diethyl tartrate, dibutyl tartrate, diisobutyl tartrate, ethyl cyclohexanecarboxylate, Methyl benzoate, ethyl benzoate, methyl p-)rulyate, ethyl p-tert-butylbenzoate, p-ethyl anisate, ethyl α-naphthoate, isobutyl α-naphthoate, ethyl cinnamate,
Monomethyl phthalate, monobutyl phthalate, dibutyl phthalate, diisobutyl phthalate, dihexyl phthalate,
Dioctyl phthalate, di-2-ethylhexyl phthalate,
Diallyl phthalate, diphenyl phthalate, diethyl isophthalate, diisobutyl isophthalate, diethyl terephthalate, dibutyl terephthalate, diethyl naphthalate,
Examples include dibutyl naphthalate, triethyl trimellidate, tributyl trimellidate, tetramethyl pyromellitate, tetraethyl pyromellitate, and tetrabutyl pyromellitate.
カルボン酸ハロゲン化物としては、上記のカルボン酸類
の酸ハロゲン化物が使用することができ、その具体例と
して、酢酸クロリド、酢酸プロミド、酢酸アイオダイド
、プロピオン酸クロリド、酪酸クロリド、酪酸プロミド
、醋酸アイオダイド、ピバリン酸クロリド、ピバリン酸
プロミド、アクリル酸クロリド、アクリル酸プロミド、
アクリル酸アイオダイド、メタクリル酸クロリド、メタ
クリル酸プロミド、メタクリル酸アイオダイド、クロト
ン酸クロリド、マロン酸クロリド、マロン酸プロミド、
コハク酸クロリド、コハク酸プロミド、グルタル酸クロ
リド、グルタル酸プロミド、アジピン酸クロリド、アジ
ピン酸プロミド、セバシン酸クロリド、セバシン酸プロ
ミド、マレイン酸クロリド、マレイン酸プロミド、フマ
ル酸クロリド、フマル酸プロミド、酒石酸クロリド、酒
石酸プロミド、シクロヘキサンカルボン酸クロリド、シ
クロヘキサンカルボン酸プロミド、1−シクロヘキセン
カルボン酸クロリド、シス−4−メチルシクロヘキセン
カルボン酸クロリド、シス−4−メチルシクロヘキセン
カルボン酸プロミド、塩化ベンゾイル、臭化ベンゾイル
、p−トルイル酸クロリド、p−トルイル酸プロミド、
p−アニス酸クロリド、p−アニス酸プロミド、α−ナ
フトエ酸クロリド、ケイ皮酸クロリド、ケイ皮酸フロミ
ド、フタル酸ジクロリド、フタル酸ジブロミド、イソフ
タル酸ジクロリド、イソフタル酸ジブロミド、テレフタ
ル酸ジクロリド、ナフタル酸ジクロリドが挙げられる。As the carboxylic acid halide, acid halides of the above-mentioned carboxylic acids can be used, and specific examples thereof include acetic acid chloride, acetic acid bromide, acetic acid iodide, propionic acid chloride, butyric acid chloride, butyric acid chloride, butyric acid bromide, acetic acid iodide, and pivalin. Acid chloride, pivalic acid bromide, acrylic acid chloride, acrylic acid bromide,
Acrylic acid iodide, methacrylic acid chloride, methacrylic acid iodide, methacrylic acid iodide, crotonic acid chloride, malonic acid chloride, malonic acid promide,
Succinic acid chloride, succinic acid bromide, glutaric acid chloride, glutaric acid bromide, adipic acid chloride, adipic acid bromide, sebacic acid chloride, sebacic acid chloride, maleic acid chloride, maleic acid chloride, fumaric acid chloride, fumaric acid bromide, tartaric acid chloride , tartaric acid bromide, cyclohexanecarboxylic acid chloride, cyclohexanecarboxylic acid chloride, 1-cyclohexenecarboxylic acid chloride, cis-4-methylcyclohexenecarboxylic acid chloride, cis-4-methylcyclohexenecarboxylic acid chloride, benzoyl chloride, benzoyl bromide, p- Toluic acid chloride, p-toluic acid bromide,
p-anisyl chloride, p-anisyl bromide, α-naphthoic chloride, cinnamic chloride, cinnamic furomide, phthalic dichloride, phthalic dibromide, isophthalic dichloride, isophthalic dibromide, terephthalic dichloride, naphthalic acid Dichloride is mentioned.
又、アジピン酸モノメチルクロリド、マレイン酸モノエ
チルクロリド、マレイン酸モノメチルクロリド、フタル
酸ブチルクロリドのようなジカルボン酸のモノアルキル
ハロゲン化物も使用し得る。Monoalkyl halides of dicarboxylic acids such as monomethyl adipate chloride, monoethyl maleate chloride, monomethyl maleate, and butyl phthalate chloride may also be used.
アルコール類は、一般式ROHで表わされる。Alcohols are represented by the general formula ROH.
式においてRは炭素数1〜12個のアルキル、アルケニ
ル、シクロアルキル、アリール、アルアルキルである。In the formula, R is alkyl, alkenyl, cycloalkyl, aryl, or aralkyl having 1 to 12 carbon atoms.
その具体例としては、メタノール、エタノール、プロパ
ツール、イソプロパツール、ブタノール、イソブタノー
ル、ペンタノール、ヘキサノール、オクタツール、2−
エチルヘキサノール、シクロヘキサノール、ベンジルア
ルコール、アリルアルコール、フェノール、クレゾール
、キシレノール、エチルフェノール、イソプロピルフェ
ノール、p−ターシャリーブチルフェノール、n−オク
チルフェノール等である。エーテル類は、一般式nOR
’で表わされる。式においてR,R’は炭素数1〜12
個のアルキル、アルケニル、シクロアルキル、アリール
、アルアルキルであり、RとR1はは同じでも異っても
よい。その具体例としては、ジエチルエーテル、ジイソ
プロピルエーテル、ジブチルエーテル、ジイソブチルエ
ーテル、ジイソアミルエーテル、ジー2−エチルヘキシ
ルエーテル、ジアリルエーテル、エチル了りルエーテル
、ブチルアリルエーテル、ジフェニルエーテル、アニソ
ール、エチルフェニルエーテル等である。Specific examples include methanol, ethanol, propatool, isoproptool, butanol, isobutanol, pentanol, hexanol, octatool, 2-
These include ethylhexanol, cyclohexanol, benzyl alcohol, allyl alcohol, phenol, cresol, xylenol, ethylphenol, isopropylphenol, p-tert-butylphenol, n-octylphenol, and the like. Ethers have the general formula nOR
' In the formula, R and R' have 1 to 12 carbon atoms.
alkyl, alkenyl, cycloalkyl, aryl, and aralkyl, and R and R1 may be the same or different. Specific examples include diethyl ether, diisopropyl ether, dibutyl ether, diisobutyl ether, diisoamyl ether, di-2-ethylhexyl ether, diallyl ether, ethyl ether, butyl allyl ether, diphenyl ether, anisole, ethylphenyl ether, etc. .
成分Aの調製法としては、■金属酸化物(tj。The method for preparing component A is as follows: ■Metal oxide (tj.
分1) マグネシウム化合物(tL分2) チタン化合
物(t!、分3)及び電子供与性化合物(成分4〉をそ
の順序に接触させる。■成分1と成分2を接触させた後
、成分4と成分3をその順序に接触させる。■成分1.
戊分2を接触させた後、成分3と成分4を同時に用いて
接触させる、■成分2と成分3を接触させた後、成分4
と成分lをその順序に接触させる、■成分2と成分4を
接触させた後、成分3と成分1をその順序に接触させる
、■成分2.成分3及び成分4を同時に接触させた後、
成分lを接触させる等の方法が採用し得る。又、成分3
を用いて接触させる前にハロゲン含有化合物と接触させ
ることもできる。min 1) Magnesium compound (tL min 2) Titanium compound (t!, min 3) and electron-donating compound (component 4) are brought into contact in that order. ■ After bringing component 1 and component 2 into contact, component 4 and Component 3 is contacted in that order. Component 1.
After contacting Bokubun 2, component 3 and component 4 are brought into contact at the same time. ■After contacting component 2 and component 3, component 4 is brought into contact.
and component 1 in that order; (2) component 2 and component 4 are brought into contact, and then component 3 and component 1 are brought into contact in that order; (2) component 2. After contacting component 3 and component 4 simultaneously,
A method such as bringing component 1 into contact may be adopted. Also, ingredient 3
It is also possible to contact with a halogen-containing compound before contacting with a halogen-containing compound.
ハロゲン含有化合物としては、ハロゲン化炭化水素、ハ
ロゲン含有アルコール、水素−珪素結合を有するハロゲ
ン化珪素化合物、周期表第Ha族、I’Va族、Va族
元素のハロゲン化物(以下、金属ハライドという。)等
が挙げられる。Examples of the halogen-containing compound include halogenated hydrocarbons, halogen-containing alcohols, halogenated silicon compounds having a hydrogen-silicon bond, and halides of Group Ha, Group I'Va, and Group Va elements of the periodic table (hereinafter referred to as metal halides). ) etc.
ハロゲン化炭化水素としては、炭素数l〜12個の飽和
又は不飽和の脂肪族、脂環式及び芳香族炭化水素のモノ
及びポリハロゲン置換体である。それら化合物の具体的
な例は、脂肪族化合物では、メチルクロライド、メチル
ブロマイド、メチル了イオダ1゛ド、メチレンクロライ
下、メチレンブロマイド、メチレンアイオダイド、クロ
ロホルム、ブロモホルム、ヨードホルム、四塩化炭素、
四臭化炭素、四沃化炭素、エチルクロライド、エチルブ
ロマイド、エチルアイオダイド、1.2−ジクロルエタ
ン、1,2−ジブロムエタン、1,2−ショートエタン
、メチルクロロホルム、メチルブロモホルム、メチルヨ
ードホルム、1.1.2−トリクロルエチレン、1.1
.2−)リブロモエチレン、1.1.2゜2−テトラク
ロルエチレン、ペンタクロルエタン、ヘキサクロルエタ
ン、ヘキサブロモエタン、n−プロピルクロライド、1
.2−ジクロルプロパン、ヘキサクロロプロピレン、オ
クタクロロプロパン、デカブロモブタン、塩素化パラフ
ィンが、脂環式化合物ではクロロシクロプロパン、テト
ラクロルシクロペンタン、ヘキサクロロシクロペンタジ
ェン、ヘキサクロルシクロヘキサンが、芳香族化合物で
はクロルベンゼン、ブロモベンゼン、0−ジクロルベン
ゼン、p−ジクロルベンゼン、ヘキサクロロベンゼン、
ヘキサブロモベンゼン、ペンシトリクロライド、p−ク
ロロベンシトリクロライド等が挙げられる。これらの化
合物は、一種のみならず二種以上用いてもよい。Examples of halogenated hydrocarbons include mono- and polyhalogen-substituted saturated or unsaturated aliphatic, alicyclic and aromatic hydrocarbons having 1 to 12 carbon atoms. Specific examples of these compounds include, for aliphatic compounds, methyl chloride, methyl bromide, methyl iodide, methylene chloride, methylene bromide, methylene iodide, chloroform, bromoform, iodoform, carbon tetrachloride,
Carbon tetrabromide, carbon tetraiodide, ethyl chloride, ethyl bromide, ethyl iodide, 1,2-dichloroethane, 1,2-dibromoethane, 1,2-short ethane, methylchloroform, methylbromoform, methyliodoform, 1. 1.2-trichlorethylene, 1.1
.. 2-) Libromoethylene, 1.1.2゜2-tetrachloroethylene, pentachloroethane, hexachloroethane, hexabromoethane, n-propyl chloride, 1
.. 2-dichloropropane, hexachloropropylene, octachloropropane, decabromobutane, and chlorinated paraffins; alicyclic compounds such as chlorocyclopropane, tetrachlorocyclopentane, hexachlorocyclopentadiene, and hexachlorocyclohexane; Benzene, bromobenzene, 0-dichlorobenzene, p-dichlorobenzene, hexachlorobenzene,
Examples include hexabromobenzene, pencitrichloride, p-chlorobencitrichloride, and the like. Not only one kind but also two or more kinds of these compounds may be used.
ハロゲン含有アルコールとしては、−分子中に一個又は
二個以上の水酸基を有するモノ又は多価アルコール中の
、水酸基以外の任意の一個又は二個以上の水素原子がハ
ロゲン原子で置換された化合物を意味する。ハロゲン原
子としては、塩素、臭素、ヨウ素、弗素原子が挙げられ
るが、塩素原子が望ましい。A halogen-containing alcohol refers to a compound in which one or more hydrogen atoms other than the hydroxyl group in a mono- or polyhydric alcohol having one or more hydroxyl groups in the molecule are substituted with a halogen atom. do. Examples of the halogen atom include chlorine, bromine, iodine, and fluorine atoms, with chlorine atoms being preferred.
それら化合物を例示すると、2−クロルエタノール、1
−クロル−2−プロパツール、3−クロル−1−プロパ
ツール、1−クロル−2−メチル−2−プロパツール、
4−90ルー1−ブタノール、5−クロル−1−ペンタ
ノール、6 9 CI JL/ −1−ヘキサノール、
3−クロル−1,2−プロパンジオール、2−クロルシ
クロヘキサノール、4−クロルベンズヒドロール、(m
、 o、 p)−クロルベンジルアルコール、4−クロ
ルカテコール、4−クロル−(m、○)−りレゾール、
6−クロル−(m、o)−クレゾール、4−クロル−3
,5−ジメチルフェノール、クロルハイドロキノン、2
−ベンジル−4−クロルフェノール、4−クロル−1−
ナフトール、(m、o、p)−クロルフェノール、p−
クロル−α−メチルベンジルアルコール、2−クロル−
4−フェニルフェノール、6−クロルチモール、4−ク
ロルレゾルシン、2−ブロムエタノール、3−ブロム−
l−プロパツール、1−ブルムー2−プロパツール、1
−ブロム−2−ブタノール、2−ブロム−p−クレゾー
ル、1−ブロム−2−ナフトール、6−ブロム−2−ナ
フトール、(m、o、p)−ブロムフェノール、4−ブ
ロムレゾルシン、(m、o、p)フロロフェノール、p
−イオドフェノール:2゜2−ジクロルエタノール、2
.3−ジクロル−1−プロパツール、1.3−ジクロル
−2−プロパツール、3−クロル−1−(α−クロルメ
チル)−1−プロパツール、2.3−ジブロム−1−プ
ロパツール、1,3−ジブロム−2−ブロパノール、2
,4−ジブロムフェノール、2.4−ジブロム−1−ナ
フトール:2,2゜2−トリクロルエタノール、1、l
1−)リクロルー2−プロパツール、β、β、β−
トリクロルーtert−ブタノール、2,3.4−トリ
クロルフェノール、2.4.5−)リクロルフェノール
、2,4.6−)リクロルフェノール、2.4.6−ト
リブロムフエノール、2,3゜5−トリブロム−2−ヒ
ドロキシトルエン、2゜3.5−トリブロム−4−ヒド
ロキシトルエン、2.2.2−)リフルオロエタノール
、α、α。Examples of these compounds include 2-chloroethanol, 1
-chlor-2-propatol, 3-chlor-1-propatol, 1-chloro-2-methyl-2-propatol,
4-90-1-butanol, 5-chloro-1-pentanol, 69 CI JL/-1-hexanol,
3-chloro-1,2-propanediol, 2-chlorocyclohexanol, 4-chlorobenzhydrol, (m
, o, p)-chlorobenzyl alcohol, 4-chlorocatechol, 4-chloro-(m,○)-resol,
6-chloro-(m,o)-cresol, 4-chloro-3
, 5-dimethylphenol, chlorohydroquinone, 2
-benzyl-4-chlorophenol, 4-chloro-1-
naphthol, (m,o,p)-chlorophenol, p-
Chlor-α-methylbenzyl alcohol, 2-chloro-
4-phenylphenol, 6-chlorthymol, 4-chlorresorcin, 2-bromoethanol, 3-bromo-
l-Proper Tools, 1-Brumoo 2-Proper Tools, 1
-bromo-2-butanol, 2-bromo-p-cresol, 1-bromo-2-naphthol, 6-bromo-2-naphthol, (m,o,p)-bromophenol, 4-bromoresorcin, (m, o, p) Fluorophenol, p
-Iodophenol: 2゜2-dichloroethanol, 2
.. 3-dichloro-1-propatol, 1.3-dichlor-2-propatol, 3-chloro-1-(α-chloromethyl)-1-propatol, 2.3-dibromo-1-propatol, 1, 3-dibromo-2-bropanol, 2
, 4-dibromophenol, 2,4-dibromo-1-naphthol: 2,2゜2-trichloroethanol, 1,l
1-) Rechloroo 2-propatool, β, β, β-
Trichloro-tert-butanol, 2,3.4-trichlorophenol, 2.4.5-)lichlorphenol, 2,4.6-)lichlorphenol, 2.4.6-tribromophenol, 2,3° 5-tribromo-2-hydroxytoluene, 2゜3.5-tribromo-4-hydroxytoluene, 2.2.2-) Refluoroethanol, α, α.
α−トリプルオローm−クレゾール、2,4゜6−ドリ
イオドフエノール:2,3.4.6−チトラクロルフエ
ノール、テトラクロルハイドロキノン、テトラクロルビ
スフェノールA1テトラブロムビスフエノールA、2.
2,3.3−テトラフルオロ−1−プロパツール、2.
3゜5.6−チトラフルオロフエノール、テトラフルオ
ロレゾルシン等が挙げられる。α-triple ol-m-cresol, 2,4°6-doliodophenol: 2,3.4.6-titrachlorphenol, tetrachlorhydroquinone, tetrachlorbisphenol A1 tetrabromobisphenol A, 2.
2,3.3-tetrafluoro-1-propertool, 2.
Examples include 3°5.6-titrafluorophenol and tetrafluororesorcin.
水素−珪素結合を有するハロゲン化珪素化合物としては
、H3iC1,、LSiCL 、 H3SiCIHC1
l+Si[’lz 、HCJsSiCla 、H(
t−Calls)SiCI2 。Examples of halogenated silicon compounds having a hydrogen-silicon bond include H3iC1, LSiCL, H3SiCIHC1
l+Si['lz, HCJsSiCla, H(
t-Calls) SiCI2.
11c、Hssiclz 、 H(CHs)zsi
cl 、 H(i−Call、)zsic1112
cJssic1 、Hz(n−CJs)SICI
、I2(Ca)laces)SiC1、H3iC1(C
aHs) 2等が挙げられる。11c, Hssiclz, H(CHs)zsi
cl, H(i-Call,)zsic1112
cJssic1, Hz (n-CJs) SICI
, I2(Ca) laces) SiC1, H3iC1(C
aHs) 2, etc.
金属ハライドとしては、B、 AI 、 Ga、 I
n。Metal halides include B, AI, Ga, I
n.
TI 、 Si 、 Ga、 Sn、 Pb、 As、
Sb、 Biの塩化物、弗化物、臭化物、ヨウ化物が
挙げられ、特にBCIs 、 8Brs 、 BI+
、AlCl3. Al0r、 。TI, Si, Ga, Sn, Pb, As,
Examples include chloride, fluoride, bromide, and iodide of Sb and Bi, especially BCIs, 8Brs, BI+
, AlCl3. Al0r, .
GaCl3 、 Ga口ra 、 InCIa
、 TIC+3 、 5iC1* 。GaCl3, GaCl3, InCIa
, TIC+3, 5iC1*.
5nC1i 、 5bC1s 、 5bFs 等が好
適である。5nC1i, 5bC1s, 5bFs, etc. are suitable.
成分1.成分2.戊分3及び成分4、更に必要に応じて
接触させることのできるハロゲン含有化合物との接触は
、不活性媒体の存在下、又は不存在下、混合攪拌するが
、機械的に共粉砕することによりなされる。接触は40
〜150℃の加熱下で行うことができる。Ingredient 1. Ingredient 2. Contact with the halogen-containing compound that can be brought into contact with Bokubun 3 and component 4 is carried out by mixing and stirring in the presence or absence of an inert medium, but by mechanical co-pulverization. It will be done. 40 contacts
It can be carried out under heating at ~150°C.
不活性媒体としては、ヘキサン、ヘプタン、オクタン等
の飽和脂肪族炭化水素、シクロペンタン、シクロヘキサ
ン等の飽和脂環式炭化水素、ベンゼン、トルエン、キシ
レン等の芳香族炭化水素が使用し得る。As the inert medium, saturated aliphatic hydrocarbons such as hexane, heptane and octane, saturated alicyclic hydrocarbons such as cyclopentane and cyclohexane, aromatic hydrocarbons such as benzene, toluene and xylene can be used.
本発明における成分Aの調製法の具体例としては、特開
昭58−162607号、同55−94909号、同5
5−115405号、同57−108107号、同al
−21109号、同61−174204号、同61−1
74205号、同61−174206号、同62−77
06号公報等に開示されている方法等が挙げられる。よ
り詳細には、
■ 金属酸化物とマグネシウムジアルコキシドとの反応
生成物を、電子供与性化合物及び4価のハロゲン化チタ
ンと接触させる方法(特開昭58−162607号公報
)
■ 無機酸化物とマグネシウムヒドロカルビルハライド
化合物との反応生成物を、ルイス塩基化合物及び四塩化
チタンと接触させる方法(特開昭55−94909号公
報)
■ シリカ等の多孔質担体とアルキルマグネシウム化合
物との反応生成物を、チタン化合物と接触させる前に電
子供与性化合物及びハロゲン化珪素化合物と接触させる
方法(特開昭55−115405号、同57−1081
07号公報:■ 金属酸化物、アルコキシ基含有マグネ
シウム化合物、オルト位にカルボキシル基を持つ芳香族
多価カルボン酸若しくはその誘導体及びチタン化合物を
接触させる方法(特開昭61−174204号公報)
■ 金属酸化物、アルコキシ含有マグネシウム化合物、
水素−珪素結合を有する珪素化合物、電子供与性化合物
及びチタン化合物を接触させる方法(特開昭61−17
4205号公報)■ 金R酸化物、アルコキシ含有マグ
ネシウム化合物、ハロゲン元素若しくはハロゲン含有化
合物、電子供与性化合物及びチタン化合物を接触させる
方法(特開昭61−174206号公報)
■ 金属酸化物、ジヒドロカルビルマグネシウム及びハ
ロゲン含有アルコールを接触させることによって得られ
る反応生成物を、電子供与性化合物及びチタン化合物と
接触させる方法(特開昭61−21109号公報)
■ 金属酸化物、ヒドロカルビルマグネシウム及びヒド
ロカルビルオキシ基含有化合物(前記アルコキシ基含有
化合物に相当)を接触させることによって得られる固体
を、ハロゲン含有アルコールと接触させ、更に電子供与
性化合物及びチタン化合物と接触させる方法(特開昭6
2−7706号公報)である。これらの内でも■〜■の
方法が、特に■、■の方法が望ましい。Specific examples of the method for preparing component A in the present invention include JP-A-58-162607, JP-A-55-94909, and JP-A-5.
No. 5-115405, No. 57-108107, al.
-21109, 61-174204, 61-1
No. 74205, No. 61-174206, No. 62-77
Examples include the method disclosed in Japanese Patent No. 06 and the like. More specifically, ■ A method in which a reaction product of a metal oxide and a magnesium dialkoxide is brought into contact with an electron-donating compound and a tetravalent titanium halide (JP-A-58-162607). A method of contacting a reaction product with a magnesium hydrocarbyl halide compound with a Lewis base compound and titanium tetrachloride (JP-A-55-94909) ■ A reaction product between a porous carrier such as silica and an alkylmagnesium compound, Method of contacting with an electron donating compound and a silicon halide compound before contacting with a titanium compound (JP-A-55-115405, JP-A No. 57-1081)
Publication No. 07: ■ A method of bringing a metal oxide, an alkoxy group-containing magnesium compound, an aromatic polycarboxylic acid having a carboxyl group at the ortho position or a derivative thereof, and a titanium compound into contact (Japanese Unexamined Patent Publication No. 174204/1983) ■ Metal oxide, alkoxy-containing magnesium compound,
A method of bringing a silicon compound having a hydrogen-silicon bond, an electron-donating compound, and a titanium compound into contact (Unexamined Japanese Patent Publication No. 61-17
4205 Publication) ■ Method of bringing gold R oxide, alkoxy-containing magnesium compound, halogen element or halogen-containing compound, electron-donating compound, and titanium compound into contact (JP-A-61-174206) ■ Metal oxide, dihydrocarbyl Method of contacting a reaction product obtained by contacting magnesium and a halogen-containing alcohol with an electron-donating compound and a titanium compound (JP-A-61-21109) ■ Metal oxide, hydrocarbylmagnesium, and hydrocarbyloxy group-containing A method of contacting a solid obtained by contacting a compound (corresponding to the alkoxy group-containing compound) with a halogen-containing alcohol, and further contacting an electron-donating compound and a titanium compound (JP-A-6
2-7706). Among these methods, methods ① to ① are particularly desirable, and methods ① and ② are particularly preferable.
上記のようにして成分Aは調製されるが、成分Aは必要
に応じて前記の不活性媒体で洗浄してもよく、更に乾燥
してもよい。Component A is prepared as described above, and if necessary, component A may be washed with the above-mentioned inert medium and may be further dried.
又、成分Aは、更に有機アルミニウム化合物の存在下、
オレフィンと接触させて成分A中に生成するオレフィン
ポリマーを含有させてもよい。有機アルミニウム化合物
としては、本発明で用いられる触媒の〜成分である後記
の有機金属化合物の中から選ばれる。In addition, component A further comprises, in the presence of an organoaluminum compound,
Olefin polymers formed in component A upon contact with olefins may also be included. The organoaluminum compound is selected from the organometallic compounds described below that are components of the catalyst used in the present invention.
オレフィンとしては、エチレンのイ也プロピレン、1−
ブテン、1−ヘキセン、4−メチル−1−ペンテン等の
α−オレフィンが使用し得る。Examples of olefins include ethylene, propylene, 1-
α-olefins such as butene, 1-hexene, 4-methyl-1-pentene can be used.
オレフィンとの接触は、前記の不活性媒体の存在下行う
のが望ましい。接触は、通常100℃辺下、望ましくは
一10〜+50℃の温度で行われる。成分人中に含有さ
せるオレフィンポリマーの量は、成分A1g当り通常0
.1〜100gである。Contact with the olefin is preferably carried out in the presence of the inert medium described above. The contacting is usually carried out at a temperature below 100°C, preferably between -10°C and +50°C. The amount of olefin polymer contained in the ingredient is usually 0 per gram of ingredient A.
.. It is 1-100g.
成分Aとオレフィンの接触は、有機アルミニウム化合物
と共に電子供与性化合物を存在させてもよい。電子供与
性化合物は、成分Aを調製させる際に用いられる化合物
の中から選択される。オレフィンと接触した成分Aは必
要に応じて前記の不活性媒体で洗浄することができ、又
更に乾燥することができる。In the contact between component A and the olefin, an electron-donating compound may be present together with the organoaluminum compound. The electron-donating compound is selected from among the compounds used in preparing component A. Component A that has been in contact with the olefin can be washed with the above-mentioned inert medium, if necessary, or further dried.
有機金属化合物
有機金属化合物(以下成分Bという。)は、周期表第1
族ないし第■族金属の有機化合物である。成分Bとして
は、リチウム、マグネシウム、カルシウム、亜鉛及びア
ルミニウムの有機化合物が使用し得る。これらの中でも
特に、有機アルミニウム化合物が好適である。用い得る
有機アルミニウム化合物としては、一般式11、、Al
X3−n(但し、Rはアルキル基又はアリール基、Xは
ハロゲン原子、アルコキシ基又は水素原子を示し、nは
1≦n≦3の範囲の任意の数である。)で示されるもの
であり、例えばトリアルキルアルミニウム、ジアルキル
アルミニウムモノハライド、モノアルキルアルミニウム
ジ゛ハライド、アルキルアルミニウムセスキハライド、
ジアルキルアルミニウムモノアルコキシド及びジアルキ
ルアルミニウムモノハイドライドなどの炭素数1ないし
18個、好ましくは炭素数2ないし6個のアルキルアル
ミニウム化合物又はその混合物もしくは錯化合物が特に
好ましい。具体的には、トリメチルアルミニウム、トリ
エチルアルミニウム、トリプロピルアルミニウム、トリ
イソブチルアルミニウム、トリヘキシルアルミ・ニウム
などのトリアルキルアルミニウム、ジメチルアルミニウ
ムクロリド、ジエチルアルミニウムクロリド、ジエチル
アルミニウムプロミド、ジエチルアルミニウムアイオダ
イド、ジイソブチルアルミニウムクロリドなどのジアル
キルアルミニウムモノハライド、メチルアルミニウムジ
クロリド、エチルアルミニウムジクロリド、メチルアル
ミニウムジクロリド、エチルアルミニウムジクロリド、
エチルアルミニウムジアイオダイド、イソブチルアルミ
ニウムジクロリドなどのモノアルキルアルミニウムシバ
ライド、エチルアルミニウムセスキクロリドなどのアル
キルアルミニウムセスキハライド、ジメチルアルミニウ
ムメトキシド、ジエチルアルミニウムエトキシド、ジエ
チルアルミニウムフェノキシド、ジプロピルアルミニウ
ムエトキシド、ジイソブチルアルミニウムエトキシド、
ジイソブチルアルミニウムフェノキシドなどのジアルキ
ルアルミニウムモノアルコキシド、ジメチルアルミニウ
ムハイドライド、ジエチルアルミニウムハイドライド、
ジプロピルアルミニウムハイドライド、ジイソブチルア
ルミニウムハイドライドなどのジアルキルアルミニウム
ハイドライドが挙げられる。これらの中でも、トリアル
キルアルミニウムが、特にトリエチルアルミニウム、ト
リイソブチルアルミニウムが望ましい。又、これらトリ
アルキルアルミニウムは、その他の有機アルミニウム化
合物、例えば、工業的に人手し易いジエチルアルミニウ
ムクロリド、エチルアルミニウムジクロリド、エチルア
ルミニウムセスキクロリド、ジエチルアルミニウムエト
キシド、ジエチルアルミニウムハイドライド又はこれら
の混合物若しくは錯化合物等と併用することができる。Organometallic compoundsOrganometallic compounds (hereinafter referred to as component B) are found in the first part of the periodic table.
It is an organic compound of a group metal to a group II metal. As component B, organic compounds of lithium, magnesium, calcium, zinc and aluminum can be used. Among these, organoaluminum compounds are particularly suitable. As the organoaluminum compound that can be used, general formula 11, Al
It is represented by , such as trialkyl aluminum, dialkyl aluminum monohalide, monoalkyl aluminum dihalide, alkyl aluminum sesquihalide,
Particularly preferred are alkyl aluminum compounds having 1 to 18 carbon atoms, preferably 2 to 6 carbon atoms, such as dialkyl aluminum monoalkoxides and dialkyl aluminum monohydrides, or mixtures or complexes thereof. Specifically, trialkylaluminum such as trimethylaluminum, triethylaluminum, tripropylaluminum, triisobutylaluminum, and trihexylaluminum, dimethylaluminum chloride, diethylaluminum chloride, diethylaluminum bromide, diethylaluminium iodide, diisobutylaluminum Dialkyl aluminum monohalides such as chloride, methyl aluminum dichloride, ethyl aluminum dichloride, methyl aluminum dichloride, ethyl aluminum dichloride,
Monoalkylaluminum cibarides such as ethylaluminum diiodide, isobutylaluminum dichloride, alkylaluminum sesquihalides such as ethylaluminum sesquichloride, dimethylaluminum methoxide, diethylaluminum ethoxide, diethylaluminum phenoxide, dipropylaluminum ethoxide, diisobutylaluminum ethoxide,
Dialkyl aluminum monoalkoxides such as diisobutyl aluminum phenoxide, dimethyl aluminum hydride, diethyl aluminum hydride,
Examples include dialkyl aluminum hydrides such as dipropyl aluminum hydride and diisobutyl aluminum hydride. Among these, trialkylaluminum is preferred, particularly triethylaluminum and triisobutylaluminum. In addition, these trialkylaluminums can be used with other organoaluminum compounds, such as diethylaluminum chloride, ethylaluminum dichloride, ethylaluminum sesquichloride, diethylaluminum ethoxide, diethylaluminum hydride, or mixtures or complexes thereof, which are industrially easy to handle. Can be used in combination with etc.
又、酸素原子や窒素原子を介して2個以上のアルミニウ
ムが結合した有機アルミニウム化合物も使用可能である
。そのような化合物としては、例えば (C2H5)2
AIOA1(C,85)2 。Furthermore, an organic aluminum compound in which two or more pieces of aluminum are bonded via an oxygen atom or a nitrogen atom can also be used. Such compounds include, for example, (C2H5)2
AIOA1(C,85)2.
(C4Hs)Jl[]^1 ([:4H1l) 2 、
(C2H5) 2AINAI (C2H5) 22
H5
等を例示できる。(C4Hs)Jl[]^1 ([:4H1l) 2,
(C2H5) 2AINAI (C2H5) 22
Examples include H5.
アルミニウム金属以外の金属の有機化合物としては、ジ
エチルマグネシウム、エチルマグネシウムクロリド、ジ
エチル亜鉛等の他
LiA1(Cz)Is)< 、 LiA1(CJ+s)
n 等の化合物が挙げられる。Examples of organic compounds of metals other than aluminum metal include diethylmagnesium, ethylmagnesium chloride, diethylzinc, etc., as well as LiA1(Cz)Is) < , LiA1(CJ+s)
Examples include compounds such as n.
エトキシ基含有シラン化合物
本発明で用いられるエトキシ基含有シラン化合物(以下
、成分Cという。)は、一般式R,Sl ((]C2H
3) 4−0で表わされ、量子化学計算で算出した分子
の体積が200〜500人3 エトキシ基の酸素原子の
電子密度が0.680〜0、800八、U、(アトミッ
クユニット〉のものである。Ethoxy group-containing silane compound The ethoxy group-containing silane compound (hereinafter referred to as component C) used in the present invention has the general formula R, Sl ((]C2H
3) It is expressed as 4-0, and the volume of the molecule calculated by quantum chemical calculation is 200 to 500 people.3 The electron density of the oxygen atom of the ethoxy group is 0.680 to 0.800, U, (atomic unit). It is something.
量子化学計算は、以下の方法による。分子の体積は、分
子軌道法プログラムであるMOPAC〔アメリカ、イン
デイアナ大学内にある化学用の各種プログラムの普及を
目的とする非営利機関であるQCPE (量子化学プロ
グラム交換機構)から購入]のMNDO法(半経験的分
子軌道法の一種) CJ、 Am、 Chem、 S
ac、、ジャーナル オブ アメリカン ケミカル ソ
サイテイ)99巻、4899頁、490?頁(1977
年);同U籾−巻、3607頁、(1978年)〕及び
Vander Waals半径CJ、 Phys、 C
hem9. (ジャーナルオブ フィジカル ケミスト
リー>68巻。Quantum chemical calculations are performed using the following method. The volume of a molecule is calculated using the MNDO method of the molecular orbital method program MOPAC (purchased from QCPE (Quantum Chemistry Program Exchange), a non-profit organization located at Indiana University in the United States that aims to disseminate various chemistry programs). (a type of semi-empirical molecular orbital method) CJ, Am, Chem, S
ac, Journal of the American Chemical Society) Volume 99, Page 4899, 490? Page (1977
(1978)] and Vander Waals radius CJ, Phys, C
hem9. (Journal of Physical Chemistry>68 volumes.
441〜451頁(1964年)〕から求めたものであ
り、エトキシ基の酸素原子の電子密度は、上記MOPA
CのMNl法により算出したものである。なお、計算に
はDEC社(DIGITAL BQU−IPMBNT
C0IIPOnATION)製ノVAX 11/785
を用いた。441-451 (1964)], and the electron density of the oxygen atom of the ethoxy group is calculated from the above MOPA
It was calculated using the MNl method of C. In addition, the calculation was carried out by DEC (DIGITAL BQU-IPMBNT).
C0IIPOnATION) VAX 11/785
was used.
成分Cの一般式におけるRは、炭素数3〜10個の脂肪
族炭化水素基、すなわちアルキル基及びアルケニル基で
ある。R in the general formula of component C is an aliphatic hydrocarbon group having 3 to 10 carbon atoms, that is, an alkyl group and an alkenyl group.
成分Cは、上記計算方法で求めた200〜500A’の
体積と、0.680〜0.800八6(I。Component C has a volume of 200 to 500 A' determined by the above calculation method and a volume of 0.680 to 0.80086 (I).
の酸素原子の電子密度を持つものであるが、特に240
〜350人3の体積と0.684〜0、700 A、U
、の該電子密度をもつものが望ましい。It has an electron density of an oxygen atom of 240
~350 people 3 volume and 0.684 ~ 0,700 A, U
It is desirable to have an electron density of .
上記のような体積と電子密度を満たす成分Cの具体例を
、化学式にて以下に例示する。式において、Me :
CHs 、 Bt : C2H5、Pr : C:+L
。A specific example of component C that satisfies the volume and electron density as described above is illustrated below using a chemical formula. In the formula, Me:
CHs, Bt: C2H5, Pr: C:+L
.
Bu : CJs 、 Pa : Cs’H++、 H
e : C11H13をそれぞれ示す。Bu: CJs, Pa: Cs'H++, H
e: Indicates C11H13.
(n−ロu)2SI (Oat)2 、 (+
Bu)2SI (OBt)2 。(n-rou)2SI (Oat)2, (+
Bu)2SI (OBt)2.
(s−Bu)zsi(Oat)z 、 (t−Bu)
zs+(OBt)a 。(s-Bu)zsi(Oat)z, (t-Bu)
zs+(OBt)a.
[(n−Pr)(Me)CHI *5i(OBt)+
、 (t−Pe)zS!(OBt)2゜[(t−Bu
)CL) 2Si(Oat)z 、 ((Bt)(M
e)CH・C1(2] 2si(OBt)2. (n
−He)2si(OBt)2゜(:(8t)(Me)2
cmcH2:] 2si(OBt)z 、 [:(t
−Bu)(CH2)2] 2si(Oat)z ;
(n−Pr)Si(QBt)s 。[(n-Pr)(Me)CHI *5i(OBt)+
, (t-Pe)zS! (OBt)2゜[(t-Bu
)CL) 2Si(Oat)z, ((Bt)(M
e) CH・C1(2] 2si(OBt)2.(n
-He)2si(OBt)2゜(:(8t)(Me)2
cmcH2:] 2si(OBt)z, [:(t
-Bu)(CH2)2] 2si(Oat)z;
(n-Pr)Si(QBt)s.
(n−Bu)Si(OBt)a 、 (t−Bu
)Si(OBt)+ 、 (n−Pe)Si(O
Bt)s 、 (t−Pe)Si(OBt)s
、 (n−Pr)(Me)C1l−5i(OBt
)a 、(t−Bu)CHI2・S+([]OBts
、(Bt) (Me)CIlCllz・5t(OBt)
s 、 (n−He)Si(Oat)a 、 (E
t)(Me)zC−CL −5i(OBt)s 、
(t−Bu) (C112)2−5i(OBt)a :
Cl1z=C1l (CHI2) s・5i(OBt)
3. CH2=CII(CLL・5i(OBt) a
、 CH2二CH(C1la) s・5i(OBt)a
、 CH2=[:H((:B2)6 ・5i(OBt
)−、(Me)Cll=CH(Cl12)−・5i(O
Bt)s ; [Cll=CH(CH2)z〕 2si
(OBt)z 、 [:CH2二CH(CH2)
4〕2si(OBt)2. [(Me)Cl=CHC
L3 −3i(OBt)2 等が挙げられる。(n-Bu)Si(OBt)a, (t-Bu
)Si(OBt)+ , (n-Pe)Si(O
Bt)s, (t-Pe)Si(OBt)s
, (n-Pr)(Me)C1l-5i(OBt
)a, (t-Bu)CHI2・S+([]OBts
, (Bt) (Me)CIlCllz・5t(OBt)
s, (n-He)Si(Oat)a, (E
t)(Me)zC-CL-5i(OBt)s,
(t-Bu) (C112)2-5i(OBt)a:
Cl1z=C1l (CHI2) s・5i(OBt)
3. CH2=CII(CLL・5i(OBt) a
, CH22CH(C1la) s・5i(OBt)a
, CH2=[:H((:B2)6 ・5i(OBt
)-, (Me)Cll=CH(Cl12)-・5i(O
Bt)s; [Cll=CH(CH2)z] 2si
(OBt)z, [:CH2CH(CH2)
4]2si(OBt)2. [(Me)Cl=CHC
L3-3i(OBt)2 etc. are mentioned.
本発明で用いられる触媒は、成分A、酸成分及び成分C
からなるが、それらの構成割合は、成分Bが成分A中の
チタン1グラム原子当り1〜2.000グラムモル、望
ましくは20〜500グラムモル、成分Cが成分B1モ
ルに対して0、001〜10モル、望ましくは0.01
〜1.0モルとなるように用いられる。The catalyst used in the present invention consists of component A, acid component and component C.
The composition ratio of component B is 1 to 2.000 g mol, preferably 20 to 500 g mol per 1 gram atom of titanium in component A, and component C is 0.001 to 10 gram mol per 1 mol of component B. mole, preferably 0.01
It is used so that it becomes 1.0 mol.
α−オレフィンの重合
本発明は、上記の触媒を用いてα−オレフィンを重合し
、ポリα−オレフィンを製造するものである。α−オレ
フィンとしては炭素数3〜10個のものであり、その具
体例としてプロピレン、1−ブテン、l−ヘキセン、4
−メチル−1−ペンテン等が挙げられる。重合は、α−
オレフィンの単独重合の他、α−オレフィンとエチレン
若しくは他のα−オレフィンとのランダム共重合も含む
。Polymerization of α-olefin In the present invention, α-olefin is polymerized using the above catalyst to produce polyα-olefin. α-olefins have 3 to 10 carbon atoms, and specific examples include propylene, 1-butene, 1-hexene,
-methyl-1-pentene and the like. Polymerization is α-
In addition to homopolymerization of olefins, it also includes random copolymerization of α-olefins and ethylene or other α-olefins.
重合反応は、気相、液相のいずれでもよく、液相で重合
させる場合は、ノルマルブタン、イソブタン、ノルマル
ペンタン、イソペンタン、ヘキサン、ヘプタン、オクタ
ン、シクロヘキサン、ベンゼン、トルエン、キシレン等
の不活性炭化水素中及び液状モノマー中で行うことがで
きる。重合温度は、通常−80℃〜+150℃、好まし
くは40〜120℃の範囲である。重合圧力は、例えば
1〜60気圧でよい。The polymerization reaction may be performed in either a gas phase or a liquid phase. When polymerizing in a liquid phase, inert carbonization of normal butane, isobutane, normal pentane, isopentane, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, etc. It can be carried out in hydrogen and in liquid monomers. The polymerization temperature is usually in the range of -80°C to +150°C, preferably 40 to 120°C. The polymerization pressure may be, for example, 1 to 60 atmospheres.
又、共重合においてα−オレフィンに共重合させる他の
オレフィンの量は、α−オレフィンに対して通常30重
量%迄、特に0.3〜15重量%の範囲で選ばれる。重
合反応は、連続又はバッチ式反応で行い、その条件は通
常用いられる条件でよい。又、重合反応は一段で行って
もよく、三役以上で行ってもよい。Further, the amount of other olefin to be copolymerized with the α-olefin in the copolymerization is usually selected within the range of 30% by weight, particularly from 0.3 to 15% by weight based on the α-olefin. The polymerization reaction may be carried out continuously or batchwise, and the conditions may be those commonly used. Further, the polymerization reaction may be carried out in one stage or may be carried out in three or more stages.
本発明は、特にメルトフローレート(MFR)が50g
/10分以上のポリα−オレフィンの製造に適しており
、MFRは公知の分子量調節剤、特に水素により調整す
ることができる。In particular, the present invention has a melt flow rate (MFR) of 50 g.
/10 minutes or more, and the MFR can be adjusted using known molecular weight regulators, especially hydrogen.
発明の効果
本発明は、特にMFRが50g/10分以上、望ましく
は70g/IQ分以上、更に望ましくは100g/10
分以上の高MFRのポリα−オレフィンの製造において
、分子量調節剤としての水素を多量に用いても熱へブタ
ン不溶分(Hl)が96%以上の高立体規則性を維持し
たまま、高収率でポリα−オレフィンを製造することが
できる。しかも、本発明で用いられるシラン化合物は、
芳香式基を有しないにもかかわらず、芳香族基を有する
シラン化合物を用いた場合と同等或いはそれ以上の触媒
性能を示す。Effects of the Invention The present invention particularly provides an MFR of 50 g/10 min or more, preferably 70 g/IQ min or more, and more preferably 100 g/10 min.
In the production of polyα-olefins with a high MFR of more than 10 minutes, even if a large amount of hydrogen is used as a molecular weight regulator, the thermally hemolyte butane insoluble content (Hl) maintains high stereoregularity of 96% or more, and the yield is high. It is possible to produce poly-alpha-olefins at a high rate. Moreover, the silane compound used in the present invention is
Although it does not have an aromatic group, it exhibits catalytic performance equivalent to or better than when using a silane compound having an aromatic group.
実施例
本発明を実施例及び比較例により具体的に説明する。な
お、例におけるパーセント(%)は特に断らない限り重
量による。EXAMPLES The present invention will be specifically explained with reference to Examples and Comparative Examples. Note that percentages (%) in the examples are based on weight unless otherwise specified.
ポリマー中の、結晶性ポリマーの割合を示すヘプタン不
溶分(以下HIと略称する。)は、改良型ソックスレー
抽出器で沸Pan−へブタンにより6時間抽出した場合
の残量である。MFRの測定は、ASTM−D 12
38に従った。The heptane-insoluble content (hereinafter abbreviated as HI), which indicates the proportion of crystalline polymer in the polymer, is the remaining amount when extracted with boiling Pan-hebutane for 6 hours using an improved Soxhlet extractor. MFR measurement is performed using ASTM-D 12
38 was followed.
実施例1
成分Aの調製
滴下ロート及び攪拌機を取付けた200mt’、のフラ
スコを窒素ガスで置換した。このフラスコに、酸化’f
イs (DAVISON社製、商品名G−952)を窒
素気流中において200℃で2時間、更に700℃で5
時間焼成したものを5g及びn−へブタンを40−入れ
た。更にn−ブチルエチルマグネシウム(以下、OHM
という。)の20%n−へブタン溶液(テキサスアルキ
ルズ社製、商品名MAGALA BBM) 20 ml
を加え、90℃で1時間攪拌した。Example 1 Preparation of Component A A 200 mt' flask equipped with a dropping funnel and a stirrer was purged with nitrogen gas. In this flask, oxidized 'f
(manufactured by DAVISON, trade name G-952) at 200℃ for 2 hours in a nitrogen stream, and then at 700℃ for 5 hours.
5 g of the calcined product and 40 g of n-hebutane were added. Furthermore, n-butylethylmagnesium (hereinafter referred to as OHM
That's what it means. ) in 20% n-hebutane solution (manufactured by Texas Alkyls, trade name: MAGALA BBM) 20 ml
was added and stirred at 90°C for 1 hour.
上記懸濁液を0℃に冷却した後、これにテトラエトキシ
シラン11.2 gを20m1’のn−へブタンに溶解
した溶液を滴下ロートから30分掛けて滴下した。滴下
終了後、2時間掛けて50℃に昇温し、50℃で1時間
攪拌を続けた。反応終了後、デカンテーションにより上
澄液を除去し、生成した固体を60m1のn−へブタン
により室温で洗浄し、更にデカンテーションにより上澄
液を除去した。このn−へブタンによる洗浄処理を更に
4回行った。After the suspension was cooled to 0° C., a solution of 11.2 g of tetraethoxysilane dissolved in 20 ml of n-hebutane was added dropwise from the dropping funnel over 30 minutes. After the dropwise addition was completed, the temperature was raised to 50°C over 2 hours, and stirring was continued at 50°C for 1 hour. After the reaction was completed, the supernatant liquid was removed by decantation, the produced solid was washed with 60 ml of n-hebutane at room temperature, and the supernatant liquid was further removed by decantation. This washing treatment with n-hebutane was further repeated four times.
上記の固体に、50m17のn−へブタンを加えて懸濁
液とし、これに2.2.2−)!Jクロルエタノール8
.0gを10rrLlのn−へブタンに溶解した溶液を
、滴下ロートから25℃において15分間掛けて滴下し
た。滴下終了後25℃で30分間攪拌を続けた。反応終
了後、室温において、60m1のn−ヘプタンにて2回
、60m1のトルエンにて3回それぞれ洗浄を行った。50ml of n-hebutane was added to the above solid to form a suspension, and 2.2.2-)! J Chlorethanol 8
.. A solution prepared by dissolving 0 g in 10 rrLl of n-hebutane was added dropwise from the dropping funnel at 25° C. over 15 minutes. After the dropwise addition was completed, stirring was continued for 30 minutes at 25°C. After the reaction was completed, washing was performed at room temperature twice with 60 ml of n-heptane and three times with 60 ml of toluene.
得られた固体(固体成分■)を分析したところ、Sl[
1236,6%、マグネシウム5.1%、塩素38.5
%を含んでいた。When the obtained solid (solid component ■) was analyzed, it was found that Sl[
1236.6%, magnesium 5.1%, chlorine 38.5
It contained %.
上記で得られた固体成分■に、n−ヘプタン10−及び
四塩化チタン40m1!を加え、90℃迄昇温し、n−
へブタン5mlに溶解したフタル酸ジn−ブチル0.6
gを5分間掛けて添加した。To the solid component (1) obtained above, 10-ml of n-heptane and 40 ml of titanium tetrachloride! was added, the temperature was raised to 90°C, and n-
0.6 di-n-butyl phthalate dissolved in 5 ml hebutane
g was added over 5 minutes.
その後、115℃に昇温し、2時間反応させた。Thereafter, the temperature was raised to 115°C, and the reaction was carried out for 2 hours.
90℃に降温した後、デカンテーションにより上澄液を
除き、n−ヘプタン70meで2回洗浄を行った。更に
、n−へブタン15rnlと四塩化チタン40Tn!、
を加え、115℃で2時間反応させた。反応終了後、得
られた固体物質を60rrf!のn−ヘキサンにて室温
で8回洗浄を行った。After the temperature was lowered to 90°C, the supernatant liquid was removed by decantation, and the mixture was washed twice with n-heptane 70me. Additionally, 15rnl of n-hebutane and 40Tn of titanium tetrachloride! ,
was added and reacted at 115°C for 2 hours. After the reaction is completed, the obtained solid material is 60rrf! Washing was performed 8 times with n-hexane at room temperature.
次いで、減圧下室源にて1時間乾燥を行い、8.3gの
触媒成分(成分A)を得た。この成分Aには、3.1%
のチタンの他酸化ケイ素、塩素及びフタル酸ジn−ブチ
ルが含まれていた。Next, drying was performed for 1 hour in a vacuum source to obtain 8.3 g of catalyst component (component A). This component A contains 3.1%
of titanium, as well as silicon oxide, chlorine and di-n-butyl phthalate.
プロピレンの重合
攪拌機を取付けた1、 51のステンレス製オートクレ
ーブに、窒素ガス雰囲気下、上記で得られた成分A10
.1mg、n−ヘプタンll中に0.8モルのトリエチ
ルアルミニウム(以下TBALと称する。)を含む溶液
4−及びn−へブタン11中に0,08モルのn−ブチ
ルトリエトキシシランを含む溶液1m2を混合し5分間
保持したものを入れた。次いで、分子量制御剤としての
水素ガス2.51及び液体プロピレン11を圧入した後
、反応系を70℃に昇温しで、1時間プロピレンの重合
を行った。重合終了後、未反応のプロピレンをパージし
、HI96.3%の白色のポリプロピレン粉末を得た。Component A10 obtained above was placed in a stainless steel autoclave No. 1 and 51 equipped with a propylene polymerization stirrer under a nitrogen gas atmosphere.
.. 1 mg of a solution containing 0.8 mol of triethylaluminum (hereinafter referred to as TBAL) in 1 ml of n-heptane (4) and a solution of 0.08 mol of n-butyltriethoxysilane in 1 ml of n-heptane (1 m2) were mixed and held for 5 minutes. Next, after 2.5 liters of hydrogen gas and 11 liters of liquid propylene as a molecular weight control agent were injected, the temperature of the reaction system was raised to 70° C., and propylene was polymerized for 1 hour. After the polymerization was completed, unreacted propylene was purged to obtain a white polypropylene powder with an HI of 96.3%.
触媒の重合活性(RC)は12.5 kg / =g−
成分A−時間であった。ポリマーのMFRは175g/
fO分であった。The polymerization activity (RC) of the catalyst is 12.5 kg/=g-
Component A - time. MFR of polymer is 175g/
It was fO minutes.
又、n−ブチルトリエトキシシランの体積及びそのエト
キシ基の酸素原子の電子密度を前記に従い計算し、その
結果を第1表に示した。Further, the volume of n-butyltriethoxysilane and the electron density of the oxygen atom of its ethoxy group were calculated as described above, and the results are shown in Table 1.
更に、水素の使用量を第1表に示す通りに変化させた以
外は、上記と同様にしてプロピレンの重合を行い、それ
らの結果を第1表を示した。Furthermore, propylene was polymerized in the same manner as above except that the amount of hydrogen used was changed as shown in Table 1, and the results are shown in Table 1.
実施例2〜12
n−ブチルトリエトキシシランの代りに、第1表に示す
シラン化合物を用い、かつ水素の使用量を第1表の通り
にした以外は、実施例1と同様にしてプロピレンの重合
を行い、それらの結果、を第1表に示した。又、それら
化合物の体積及び該電子密度を計算し、その結果を第1
表に示した。Examples 2 to 12 Propylene was prepared in the same manner as in Example 1, except that the silane compounds shown in Table 1 were used instead of n-butyltriethoxysilane, and the amount of hydrogen used was as shown in Table 1. Polymerization was carried out and the results are shown in Table 1. Also, calculate the volumes and electron densities of these compounds, and use the results as the first
Shown in the table.
比較例1〜6
シラン化合物として第2表に示す化合物を用い、かつ水
素使用量を第2表の通りにした以外は、実施例1と同様
にしてプロピレンの重合を行い、それらの結果を第2表
に示した。又、それら化合物の体積及び該電子密度の計
算値は、第2表に示す通りである。Comparative Examples 1 to 6 Propylene was polymerized in the same manner as in Example 1, except that the compounds shown in Table 2 were used as silane compounds, and the amount of hydrogen used was as shown in Table 2. It is shown in Table 2. Further, the volumes of these compounds and the calculated values of the electron densities are as shown in Table 2.
参考例1〜3
シラン化合物として第2表に示す芳香族基含有化合物を
用い、かつ水素使用量を第2表の通りにした以外は、実
施例1と同様にしてプロピレンの重合を行い、それらの
結果を第2表に示した。又、それら化合物の体積及び該
電子密度の計算値は第2表に示す通りである。Reference Examples 1 to 3 Propylene was polymerized in the same manner as in Example 1, except that the aromatic group-containing compounds shown in Table 2 were used as the silane compounds, and the amount of hydrogen used was as shown in Table 2. The results are shown in Table 2. Further, the volumes of these compounds and the calculated values of the electron densities are as shown in Table 2.
実施例
シラン化合物
体積
(人3)
一!王密掌
(^、U、)
(n−Bu) Si (OBt) 5
230、4
0、6846
(t−Bu) 5i(Oat) 3
(II−Pe) Si (OEt) 3230゜6
247、7
0、6901
0、6860
(n−Pr)(Me)CH−Si(OBt)s(t−P
a) Si (OEt) 5
(n−He) S i (0[!t) 5(s−Bu)
zsi (OEt) 2[(n−Pr) (Me)
CHI as i (OEt) *C(Et) (Me
) xc−C)I) isi (OEt) x(n−H
e) !S i (OEt) 2248、0
247、6
6t8
256、8
290、7
324.6
324、2
0、6898
0、6940
0、6871
0、6870
0、6990
0.6893
0、6810
CH,=CH(CH2) 4・5i(OEt)a[:H
2=CH(C)lx) 1S+ (OEt) 。Example silane compound volume (3 people) 1! Wang secret palm (^, U,) (n-Bu) Si (OBt) 5 230, 4 0, 6846 (t-Bu) 5i (Oat) 3 (II-Pe) Si (OEt) 3230゜6 247, 7 0,6901 0,6860 (n-Pr)(Me)CH-Si(OBt)s(t-P
a) Si (OEt) 5 (n-He) Si (0[!t) 5 (s-Bu)
zsi (OEt) 2[(n-Pr) (Me)
CHI as i (OEt) *C(Et) (Me
) xc-C)I) isi (OEt) x(n-H
e)! S i (OEt) 2248, 0 247, 6 6t8 256, 8 290, 7 324.6 324, 2 0, 6898 0, 6940 0, 6871 0, 6870 0, 6990 0.6893 0, 6810 CH,=CH( CH2) 4・5i(OEt)a[:H
2=CH(C)lx) 1S+ (OEt).
259、9
293、9
0、6865
0、6877
2.5
11.5
96.8
35
15.1
12.9
14.9
15.8
18.3
17.5
97.8
97.8
97.1
97.7
97.5
98、l
14.7
62
96.9
97.5
例
シラン化合物
比較例1
S、i (OEt) 4
〃 2
〃 3
〃 4
〃 5
〃 6
MeSi (OEt) s
εtSi(0εt)s
(Me) 2Sl (DEt) 2
(n−Pe) 2S i (OEt) a(t−Bu)
(Me) Si (OEt) x参考例1
〃 2
〃 3
CJsSt (OEt) 3
(Cells) (Me) Si (OEt) 2(C
,Hs) (Me) Si (DMe) 2体積
(A’)
204.6
第 2 表
電子密度
(A、 [1,〉
0、6762
179、3
196、5
154.1
903
205、1
0、6845
0、6858
0、6658
0、6765
0、6799
2.5
2.5
2.5
2.5
8.0
92.0
21
■1.6
95.2
20
13.2
96.1
45
11.2
91.8
74259, 9 293, 9 0, 6865 0, 6877 2.5 11.5 96.8 35 15.1 12.9 14.9 15.8 18.3 17.5 97.8 97.8 97.1 97 .7 97.5 98, l 14.7 62 96.9 97.5 Example Silane Compound Comparative Example 1 S, i (OEt) 4 〃 2 〃 3 〃 4 〃 5 〃 6 MeSi (OEt) s εtSi(0εt) s (Me) 2Sl (DEt) 2 (n-Pe) 2S i (OEt) a(t-Bu)
(Me) Si (OEt) x Reference example 1 〃 2 〃 3 CJsSt (OEt) 3 (Cells) (Me) Si (OEt) 2 (C
, Hs) (Me) Si (DMe) 2 Volume (A') 204.6 Second table Electron density (A, [1,〉 0, 6762 179, 3 196, 5 154.1 903 205, 1 0, 6845 0, 6858 0, 6658 0, 6765 0, 6799 2.5 2.5 2.5 2.5 8.0 92.0 21 ■1.6 95.2 20 13.2 96.1 45 11.2 91 .8 74
第 1図は、 本発明の方法を示すフローチャー ト図である。 No. Figure 1 is Flowchart illustrating the method of the invention This is a diagram.
Claims (1)
び電子供与性化合物を必須成分とする固体触媒成分、 (B)有機金属化合物及び (C)一般式R_nSi(OC_1H_5)_4_−_
n〔但し、Rは炭素数3〜10個の脂肪族炭化水素基、
nは1又は2である。〕で表わされ、量子化学計算で算
出した体積が200〜500Å^3、同じくエトキシ基
の酸素原子の電子密度が0.680〜0.800A.U
.(アトミックユニット)のエトキシ基含有シラン化合
物 とからなる触媒の存在下、α−オレフィンを重合するこ
とからなるポリα−オレフィンの製造法。[Scope of Claims] (A) a solid catalyst component containing a metal oxide, magnesium, titanium, halogen, and an electron-donating compound as essential components, (B) an organometallic compound, and (C) a general formula R_nSi(OC_1H_5)_4_- _
n [However, R is an aliphatic hydrocarbon group having 3 to 10 carbon atoms,
n is 1 or 2. ], the volume calculated by quantum chemical calculation is 200 to 500 Å^3, and the electron density of the oxygen atom of the ethoxy group is 0.680 to 0.800 A. U
.. A method for producing a poly-α-olefin, which comprises polymerizing an α-olefin in the presence of a catalyst comprising an ethoxy group-containing silane compound (atomic unit).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2071829A JP2775508B2 (en) | 1989-09-25 | 1990-03-23 | Method for producing poly-α-olefin |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1-246512 | 1989-09-25 | ||
JP24651289 | 1989-09-25 | ||
JP2071829A JP2775508B2 (en) | 1989-09-25 | 1990-03-23 | Method for producing poly-α-olefin |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH03174412A true JPH03174412A (en) | 1991-07-29 |
JP2775508B2 JP2775508B2 (en) | 1998-07-16 |
Family
ID=26412930
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2071829A Expired - Fee Related JP2775508B2 (en) | 1989-09-25 | 1990-03-23 | Method for producing poly-α-olefin |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP2775508B2 (en) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02229806A (en) * | 1989-03-02 | 1990-09-12 | Mitsui Petrochem Ind Ltd | Method for polymerizing olefin |
JPH02283703A (en) * | 1989-04-24 | 1990-11-21 | Sumitomo Chem Co Ltd | Production of highly stereoregular alpha-olefin polymer |
-
1990
- 1990-03-23 JP JP2071829A patent/JP2775508B2/en not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02229806A (en) * | 1989-03-02 | 1990-09-12 | Mitsui Petrochem Ind Ltd | Method for polymerizing olefin |
JPH02283703A (en) * | 1989-04-24 | 1990-11-21 | Sumitomo Chem Co Ltd | Production of highly stereoregular alpha-olefin polymer |
Also Published As
Publication number | Publication date |
---|---|
JP2775508B2 (en) | 1998-07-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2772573B2 (en) | α-Olefin polymerization catalyst | |
JPH0333103A (en) | Catalyst for polymerization of alpha-olefin | |
JPH0333106A (en) | Catalyst for polymerization of alpha-olefin | |
JPH04117411A (en) | Production of poly-alpha-olefin | |
JPH0333102A (en) | Catalyst for polymerization of alpha-olefin | |
JPH03174412A (en) | Production of poly-alpha-olefin | |
JPH0333105A (en) | Catalyst for polymerization of alpha-olefin | |
JPH11349622A (en) | Preparation of propylene copolymer | |
JPH0797411A (en) | Production of propylene block copolymer | |
JPH0480207A (en) | Alpha-olefin polymerization catalyst | |
JP2775507B2 (en) | Method for producing poly-α-olefin | |
JP3364138B2 (en) | α-olefin polymerization catalyst | |
JPH04372610A (en) | Production of polypropylene | |
JPH06157650A (en) | Catalyst component for polymerization of alpha-olefin | |
JPH0480210A (en) | Alpha-olefin polymerization catalyst | |
JPH06179718A (en) | Catalyst component for polymerizing alpha-olefin | |
JPH0376709A (en) | Catalyst component for alpha-olefin polymerization | |
JPH0480209A (en) | Catalyst component for alpha-olefin polymerization | |
JPH11302316A (en) | Production of propylene copolymer | |
JPH0472305A (en) | Catalyst for polymerization of alpha-olefin | |
JP2000007726A (en) | Production of propylene copolymer | |
JPH11322851A (en) | Production of propylene copolymer | |
JPH048707A (en) | Catalyst component for alpha-olefin polymerization | |
JPH0376708A (en) | Catalyst component for alpha-olefin polymerization | |
JPH048708A (en) | Catalyst component for alpha-olefin polymerization |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |