JP2006521451A - 電子供与体としてシクロアルカンジカルボキシレートを含むオレフィン重合触媒 - Google Patents
電子供与体としてシクロアルカンジカルボキシレートを含むオレフィン重合触媒 Download PDFInfo
- Publication number
- JP2006521451A JP2006521451A JP2006507495A JP2006507495A JP2006521451A JP 2006521451 A JP2006521451 A JP 2006521451A JP 2006507495 A JP2006507495 A JP 2006507495A JP 2006507495 A JP2006507495 A JP 2006507495A JP 2006521451 A JP2006521451 A JP 2006521451A
- Authority
- JP
- Japan
- Prior art keywords
- magnesium
- carbon atoms
- catalyst component
- electron donor
- butyl
- 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
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 16
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 12
- 239000002685 polymerization catalyst Substances 0.000 title claims description 5
- 239000011777 magnesium Substances 0.000 claims abstract description 150
- 239000003054 catalyst Substances 0.000 claims abstract description 124
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 106
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 88
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 74
- 239000010936 titanium Substances 0.000 claims abstract description 64
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 54
- 239000007787 solid Substances 0.000 claims abstract description 43
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 40
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 22
- 125000001424 substituent group Chemical group 0.000 claims abstract description 20
- 150000001924 cycloalkanes Chemical class 0.000 claims abstract description 17
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 17
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 17
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 16
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical class 0.000 claims abstract description 11
- -1 2-ethylhexyl Chemical group 0.000 claims description 83
- 150000001875 compounds Chemical class 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 150000007942 carboxylates Chemical class 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 229910052782 aluminium Inorganic materials 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 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 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 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 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 abstract description 43
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 description 39
- 238000007334 copolymerization reaction Methods 0.000 description 38
- 238000000034 method Methods 0.000 description 37
- 239000000203 mixture Substances 0.000 description 32
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 239000007788 liquid Substances 0.000 description 26
- 239000002245 particle Substances 0.000 description 25
- 239000000243 solution Substances 0.000 description 21
- 239000003085 diluting agent Substances 0.000 description 18
- 239000000463 material Substances 0.000 description 18
- 239000003607 modifier Substances 0.000 description 17
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 16
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 16
- 239000004711 α-olefin Substances 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 239000000178 monomer Substances 0.000 description 15
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 15
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 15
- 239000001569 carbon dioxide Substances 0.000 description 14
- 229910002092 carbon dioxide Inorganic materials 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 229920001155 polypropylene Polymers 0.000 description 13
- 125000004429 atom Chemical group 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 0 CC(*)(C1)C(C)(*)C2C1(CC1)C1C2 Chemical compound CC(*)(C1)C(C)(*)C2C1(CC1)C1C2 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000002002 slurry Substances 0.000 description 10
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 10
- 229910052723 transition metal Inorganic materials 0.000 description 10
- 150000003624 transition metals Chemical class 0.000 description 10
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 9
- 239000002841 Lewis acid Substances 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 150000007517 lewis acids Chemical class 0.000 description 9
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 9
- 239000011701 zinc Substances 0.000 description 9
- RVDLHGSZWAELAU-UHFFFAOYSA-N 5-tert-butylthiophene-2-carbonyl chloride Chemical compound CC(C)(C)C1=CC=C(C(Cl)=O)S1 RVDLHGSZWAELAU-UHFFFAOYSA-N 0.000 description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 8
- 125000005907 alkyl ester group Chemical group 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 150000003609 titanium compounds Chemical class 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 150000001282 organosilanes Chemical class 0.000 description 7
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
- 150000001491 aromatic compounds Chemical class 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 229910000077 silane Inorganic materials 0.000 description 6
- 150000004756 silanes Chemical class 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical group CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 150000002681 magnesium compounds Chemical class 0.000 description 5
- 150000007524 organic acids Chemical class 0.000 description 5
- 235000005985 organic acids Nutrition 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000006228 supernatant Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 150000003623 transition metal compounds Chemical class 0.000 description 5
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000004292 cyclic ethers Chemical class 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000012685 gas phase polymerization Methods 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Chemical group 0.000 description 4
- 239000011949 solid catalyst Substances 0.000 description 4
- 239000002195 soluble material Substances 0.000 description 4
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- UAEPNZWRGJTJPN-UHFFFAOYSA-N Methylcyclohexane Natural products CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 150000005840 aryl radicals Chemical class 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- NHYFIJRXGOQNFS-UHFFFAOYSA-N dimethoxy-bis(2-methylpropyl)silane Chemical compound CC(C)C[Si](OC)(CC(C)C)OC NHYFIJRXGOQNFS-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 description 3
- HONQAQNYJBKAMA-UHFFFAOYSA-L magnesium;ethyl carbonate Chemical compound [Mg+2].CCOC([O-])=O.CCOC([O-])=O HONQAQNYJBKAMA-UHFFFAOYSA-L 0.000 description 3
- 125000005498 phthalate group Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000001226 reprecipitation Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229910001868 water Inorganic materials 0.000 description 3
- 150000003738 xylenes Chemical class 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-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
- 238000005698 Diels-Alder reaction Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- FHUODBDRWMIBQP-UHFFFAOYSA-N Ethyl p-anisate Chemical compound CCOC(=O)C1=CC=C(OC)C=C1 FHUODBDRWMIBQP-UHFFFAOYSA-N 0.000 description 2
- UUGLJVMIFJNVFH-UHFFFAOYSA-N Hexyl benzoate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1 UUGLJVMIFJNVFH-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229910003902 SiCl 4 Inorganic materials 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 150000001934 cyclohexanes Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 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 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
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-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
- 150000002576 ketones Chemical class 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical class O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- ROTONRWJLXYJBD-UHFFFAOYSA-N oxan-2-ylmethanol Chemical compound OCC1CCCCO1 ROTONRWJLXYJBD-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- HXLWJGIPGJFBEZ-UHFFFAOYSA-N tert-butyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C(C)(C)C HXLWJGIPGJFBEZ-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- XYJRNCYWTVGEEG-UHFFFAOYSA-N trimethoxy(2-methylpropyl)silane Chemical compound CO[Si](OC)(OC)CC(C)C XYJRNCYWTVGEEG-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- JBIQAPKSNFTACH-UHFFFAOYSA-K vanadium oxytrichloride Chemical compound Cl[V](Cl)(Cl)=O JBIQAPKSNFTACH-UHFFFAOYSA-K 0.000 description 1
- JTJFQBNJBPPZRI-UHFFFAOYSA-J vanadium tetrachloride Chemical compound Cl[V](Cl)(Cl)Cl JTJFQBNJBPPZRI-UHFFFAOYSA-J 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/58—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with silicon, germanium, tin, lead, antimony, bismuth or compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/04—Monomers containing three or four carbon atoms
- C08F110/06—Propene
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Abstract
Description
本発明のアルキルジカルボン酸エステルにおいて、カルボキシレート基は立体配座的に近い位置に置かれる。好ましくは、このようなカルボキシレート基は、隣接する炭素原子に付いてアルキルシクロアルカン 1,2 ジカルボキシレートを形成する。本発明の別の側面において、このようなカルボキシレート基は、カルボキシレート基が隣接する炭素原子上にはないシクロアルカン 1,3 ジカルボキシレートなどを形成してもよい。いかなる場合にも、シクロアルカンの配座構造は、カルボキシレート基が立体配座的に近い位置に置かれるように置換基(又はビシクロ構造の場合には化学結合)によって制約される。特定の配座が好ましいなどの結合回転変化又は環配座変化が限定される場合に構造は制約される。
これらの化合物の典型例は、置換シクロヘキサン:
により表される。
カルボキシル基の配座を示すこれらの置換シクロヘキサンの他の代表例は、
である。このような環構造の残りの置換基は、通常は水素であるが、所望の環配座を作る他の親和性基でもよい。
このような環構造の残りの置換基は、通常は水素であるが、所望の環配座を形成する他の親和性基であってもよい。
本発明の一側面において、カルボキシレート基は、少なくとも2個のカルボキシレート基が立体配座的に近い位置、すなわちシクロアルキル環構造の好ましい配座にあるようにシクロアルキル構造上に位置づけられ、カルボキシレート基は基間のファンデルワールス(Van der Waals)斥力を受けるために十分近いが離間されるであろう。このような斥力は、典型的には、環配座がその他の点では制約されていなかったならば、環を別の好ましい配座に置くために十分である。
立体配座的に近いカルボキシレート基の一例は、トランス-ジ-n-ブチル-4,5-ジ-イソプロピルシクロヘキサン トランス-ジカルボキシレートおよびトランス-ジイソプロピル 4,5-ジ-t-ブチルシクロヘキサン トランス-ジカルボキシレートである:
無水シクロヘキサンを、エタノールおよびp-トルエンスルホン酸触媒でエステル化して、シス-ジエステルを得て、上記に概略を記載した手順に従って、触媒を調製するための内部供与体として用いた。シス-ジエステルは、ナトリウムエトキシドおよびエタノールで、より熱力学的に安定なトランス異性体にエピマー化されてもよく、触媒は上述のように調製されてもよい。
y+n=2の場合、
マグネシウム含有種を形成するマグネシウム化合物は、式XMgR(式中、Xはハロゲンであり、Rは炭素数1〜20のヒドロカルビル基である)を有するヒドロカルビルマグネシウム化合物であり、ヒドロカルビルマグネシウム化合物と二酸化炭素との反応はマグネシウムカルボキシレートを形成し、以下のように表すことができる:
本発明に有用なヒドロカルビルマグネシウム化合物は構造R-Mg-Q(式中、Qは水素、ハロゲンもしくはR'(各R'は独立に炭素数1〜20のヒドロカルビル基である))を有する。本発明に有用なヒドロカルビルマグネシウム化合物の特定の例としては、Mg(CH3)2、Mg(C2H5)2、Mg(C4H9)2、Mg(C6H5)2、Mg(C6H13)2、Mg(C9H19)2、Mg(C10H7)2、Mg(C12H9)2、Mg(C12H25)2、Mg(C16H33)2、Mg(C20H41)2、Mg(CH3)(C2H5)、Mg(CH3)(C6H13)、Mg(C2H5)(C8H17)、Mg(C6H13)(C20H41)、Mg(C3H7)(C10H7)、Mg(C2H4Cl)2およびMg(Cl6H33)(Cl8H37)、Mg(C2H5)(H)、Mg(C2H5)(Cl)、Mg(C2H5)(Br)などを挙げることができる。所望により、ヒドロカルビルマグネシウム化合物の混合物もまた用いることができる。費用および入手性の観点から、本発明で用いるために好ましいジヒドロカルビルマグネシウム化合物は式MgR2(式中、Rは上記定義したとおりである)の化合物である。触媒活性および立体特異性の点で、最良の結果は式MgR'Q'(式中、R'は炭素数1〜約18のアルキルラジカル、炭素数6〜約12のアリールラジカル又は炭素数7〜約12のアルカリルもしくはアラルキルラジカルであり、Q'はクロライド又はブロミドである)のヒドロカルビルマグネシウムハライド化合物を用いることにより達成される。
例えば、反転したマグネシウム金属をメタノール、エタノール又は1-プロパノールなどの低分子量アルコールと反応させることにより調製したマグネシウムアルコレートを用いて、四塩化ヨウ素又は四塩化炭素などの触媒を用いて又は用いずに、固体マグネシウムアルコレートを形成してもよい。任意の過剰アルコールは濾過、蒸発又は傾瀉により除かれる。この態様で製造されたマグネシウムアルコレートのマグネシウム含有化合物としての使用は、実質的に粘度が減少したマグネシウム含有種溶液を与える。
好ましくは、各ヒドロカルビル基(R1、R2およびR3)はアルキル基である。好ましくは、ホスホネートが用いられる。上述の好ましい成分として使用するに適切な特定のホスホネートとしては、ジメチルメチルホスホネート、ジエチルエチルホスホネート、ジイソプロピルメチルホスホネート、ジブチルブチルホスホネートおよびジ(2-エチルヘキシル)-2-エチルヘキシルホスホネートを挙げることができる。
機械的撹拌装置を具備し乾燥窒素でフラッシュされた2リットル反応器に、153gのマグネシウムエトキシド、276mlの2-エチル-1-ヘキサノールおよび1100mlのトルエンの混合物を移す。この混合物を450rpmにて30psigの二酸化炭素下で撹拌し、93℃にて3時間加熱する。得られた溶液(1530ml)を2リットルのボトルに移す。溶液は1mlあたり0.10グラム当量のマグネシウムエトキシドを含む。
1.0リットル反応器に、一面の乾燥窒素下で、150mlのトルエン、20.5mlのテトラエトキシシランおよび14mlのチタンテトラクロライドを仕込む。混合物を300rpmにて22〜27℃で15分間撹拌した後、高圧容器(bomb)を通して114mlの工程Aで得たマグネシウムヒドロカルビルカーボネート溶液を反応器に添加し、その後、固体粒子を沈降させる。
沈降物を含む混合物をさらに5分間撹拌した後、シリンジを通して27mlのテトラヒドロフラン(THF)を速やかに添加した。反応器内温度は26℃から38℃に上昇する。その後、300rpmにて撹拌を維持し、温度を15分以内で60℃まで上昇させる。最初に形成された固体は、THF溶液中に溶解する。THF添加後約5分以内に、固体が溶液から沈降し始めた。60℃で1時間にわたり撹拌し続け、その後、撹拌を中止し、得られた固体を沈殿させる。上澄み液を傾瀉して、固体を50mlのトルエンで2回洗浄した。
1リットル反応器内の工程Cからの固体に125mlのトルエンおよび50mlのチタンテトラクロライドを添加する。得られる混合物を116℃まで30分以内で加熱して、300rpmで1時間撹拌する。撹拌を停止した後、得られる固体を沈殿させ、上澄み液を傾瀉する。150mlのトルエン、50mlのチタンテトラクロライド、本発明の電子供与体化合物を得られる固体に添加した後、混合物を300rpmで117℃にて90分間撹拌し、固体を沈殿させ、上澄み液体を傾瀉する。95mlのトルエンを添加した後、混合物を91℃まで30分間で加熱する。撹拌を停止した後、固体を沈殿させ、上澄み液を傾瀉する。さらに125mlのチタンテトラクロライドを添加し、混合物を91℃にて撹拌しながら30分間加熱し、その後、撹拌を停止し、上澄み液体を傾瀉する。残留物を50mlのヘキサンで4回洗浄し、固体を回収する。反応体中のマグネシウム/チタン/電子供与体成分のモル比は、例えば1/5/0.45である。
Claims (15)
- マグネシウム、チタンおよびハロゲンを含み、さらに置換ヒドロカルビル4〜8員シクロアルカンジカルボキシレート(置換基はシクロアルカンに位置づけられて、ジカルボキシレート基を立体配座的に近い位置に置き、置換基は1〜20個の炭素原子を含み、シクロアルカン構造と結合してビシクロ構造を形成し得る)を含む内部電子供与体を含有するオレフィン類を重合する際に有用な固体炭化水素不溶性触媒成分。
- 前記内部電子供与体は、トランス-ジ-n-ブチル-4,5-ジ-イソプロピルシクロヘキサン トランス-ジカルボキシレート又はトランス-ジイソプロピル-4,5-ジ-t-ブチルシクロヘキサン トランス-ジカルボキシレートである、請求項1に記載の触媒成分。
- Rは、エチル、プロピル、イソプロピル、n-ブチル、イソブチル、s-ブチル、t-ブチル、n-ペンチル、イソペンチル、ヘキシル、2-エチルヘキシル又はオクチルである、請求項1に記載の触媒成分。
- Rは3〜8個の炭素原子を含む、請求項1に記載の触媒成分。
- Rはエチル、プロピル、イソプロピル、n-ブチル、イソブチル又はs-ブチルである、請求項1に記載の触媒成分。
- 少なくとも1の嵩高い置換基は3〜20個の炭素原子を含む、請求項1に記載の触媒成分。
- イソプロピル、イソブチル、t-ブチル、s-ブチル、イソペンチル、イソヘキシル又は2-エチルヘキシルの少なくとも1である、請求項1に記載の触媒成分。
- イソプロピル、イソブチル、t-ブチル又はs-ブチルの少なくとも1である、請求項1に記載の触媒成分。
- 少なくとも1の嵩高い置換基は1個のヘテロ原子を含む、請求項1に記載の触媒成分。
- マグネシウム、チタンおよびハロゲンおよび内部電子供与体化合物を含む固体炭化水素不溶性成分、アルミニウムアルキル化合物および置換ヒドロカルビル4〜8員シクロアルカンジカルボキシレート(置換基はシクロアルカンに位置づけられていてジカルボキシレート基を立体配座的に近い位置に置き、置換基は1〜20個の炭素原子を含み、シクロアルカン構造に結合してビシクロ構造を形成し得る)を含む外部電子供与体化合物を含むオレフィン重合触媒系。
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Cited By (4)
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---|---|---|---|---|
WO2009057747A1 (ja) * | 2007-11-01 | 2009-05-07 | Mitsui Chemicals, Inc. | 固体状チタン触媒成分、オレフィン重合用触媒およびオレフィンの重合方法 |
KR101228202B1 (ko) * | 2007-11-27 | 2013-01-30 | 미쓰이 가가쿠 가부시키가이샤 | 고체상 타이타늄 촉매 성분, 올레핀 중합용 촉매 및 올레핀의 중합 방법 |
JP2013516535A (ja) * | 2010-01-13 | 2013-05-13 | サムスン トータル ペトロケミカルズ カンパニー リミテッド | プロピレン重合用固体触媒の製造方法及びそれによって製造された触媒 |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006077946A1 (ja) * | 2005-01-19 | 2006-07-27 | Mitsui Chemicals, Inc. | オレフィン重合体の製造方法および固体状チタン触媒成分 |
US7491781B2 (en) | 2005-03-08 | 2009-02-17 | Ineos Usa Llc | Propylene polymer catalyst donor component |
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US10822438B2 (en) | 2017-05-09 | 2020-11-03 | Formosa Plastics Corporation | Catalyst system for enhanced stereo-specificity of olefin polymerization and method for producing olefin polymer |
US10124324B1 (en) | 2017-05-09 | 2018-11-13 | Formosa Plastics Corporation, Usa | Olefin polymerization catalyst components and process for the production of olefin polymers therewith |
CN114426603B (zh) * | 2020-10-16 | 2023-11-14 | 中国石油化工股份有限公司 | 乙烯聚合的方法及聚乙烯 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH03168207A (ja) * | 1989-11-06 | 1991-07-22 | Basf Ag | ツィーグラー/ナッタの触媒タイプの触媒系 |
JPH09104714A (ja) * | 1996-08-28 | 1997-04-22 | Mitsui Petrochem Ind Ltd | α−オレフインの重合方法 |
JP2001114811A (ja) * | 1999-10-15 | 2001-04-24 | Idemitsu Petrochem Co Ltd | オレフィン重合用触媒及びオレフィン重合体の製造方法 |
JP2001151816A (ja) * | 1999-11-25 | 2001-06-05 | Japan Polychem Corp | プロピレン系重合体およびその製造方法 |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1805765C3 (de) | 1968-10-29 | 1980-09-11 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Polymerisation von Propylen |
US4003712A (en) | 1970-07-29 | 1977-01-18 | Union Carbide Corporation | Fluidized bed reactor |
US3971786A (en) | 1972-09-05 | 1976-07-27 | Smith Kline & French Laboratories Limited | Pyridyl alkylguanidine compounds, composition therewith, and methods of inhibiting H-2 histamine receptors |
US3957448A (en) | 1974-12-16 | 1976-05-18 | Standard Oil Company | Divided horizontal reactor for the vapor phase polymerization of monomers at different hydrogen levels |
US3970611A (en) | 1974-12-16 | 1976-07-20 | Standard Oil Company | Melt finishing process for polymers produced by vapor state polymerization processes |
CA1053846A (en) | 1974-12-16 | 1979-05-01 | The Standard Oil Company | Horizontal reactor for the vapor phase polymerization of monomers |
US3965083A (en) | 1974-12-16 | 1976-06-22 | Standard Oil Company | Process for the vapor phase polymerization of monomers in a horizontal, quench-cooled, stirred-bed reactor using essentially total off-gas recycle and melt finishing |
US4101289A (en) | 1975-12-19 | 1978-07-18 | Standard Oil Company A Corporation Of Indiana | Horizontal reactor for the vapor phase polymerization of monomers |
DE2805838A1 (de) * | 1977-02-24 | 1978-08-31 | Ciba Geigy Ag | Neue 4-acyloxypiperidine |
JPS5883006A (ja) | 1981-11-13 | 1983-05-18 | Mitsui Petrochem Ind Ltd | オレフインの重合方法 |
ATE22452T1 (de) | 1982-02-12 | 1986-10-15 | Mitsui Petrochemical Ind | Verfahren zur herstellung von polymeren von olefinen. |
US4442276A (en) | 1982-02-12 | 1984-04-10 | Mitsui Petrochemical Industries, Ltd. | Process for polymerizing or copolymerizing olefins |
US4866022A (en) | 1984-03-23 | 1989-09-12 | Amoco Corporation | Olefin polymerization catalyst |
US4540679A (en) | 1984-03-23 | 1985-09-10 | Amoco Corporation | Magnesium hydrocarbyl carbonate supports |
US4612299A (en) | 1984-07-09 | 1986-09-16 | Amoco Corporation | Magnesium carboxylate supports |
US4579836A (en) | 1985-05-22 | 1986-04-01 | Amoco Corporation | Exhaustively prepolymerized supported alpha-olefin polymerization catalyst |
JPH01178710A (ja) | 1988-01-06 | 1989-07-14 | Mazda Motor Corp | エンジンのバルブ駆動装置 |
US5166113A (en) * | 1989-11-06 | 1992-11-24 | Harald Schwager | Zieger-natta-type catalyst systems |
ID28200A (id) | 1999-04-15 | 2001-05-10 | Basell Technology Co Bv | Komponen katalis untuk polimerisasi olefin |
-
2004
- 2004-03-24 CN CNA2007101286379A patent/CN101117364A/zh active Pending
- 2004-03-24 US US10/548,819 patent/US8716514B2/en active Active
- 2004-03-24 WO PCT/US2004/008888 patent/WO2004087771A1/en active Application Filing
- 2004-03-24 JP JP2006507495A patent/JP4624986B2/ja not_active Expired - Lifetime
- 2004-03-24 CN CNA2004800082538A patent/CN1771268A/zh active Pending
- 2004-03-24 EP EP04758228.3A patent/EP1613670B1/en not_active Expired - Lifetime
- 2004-03-24 EP EP10180083.7A patent/EP2261267B1/en not_active Expired - Lifetime
-
2014
- 2014-02-20 US US14/184,973 patent/US20140171294A1/en not_active Abandoned
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH03168207A (ja) * | 1989-11-06 | 1991-07-22 | Basf Ag | ツィーグラー/ナッタの触媒タイプの触媒系 |
JPH09104714A (ja) * | 1996-08-28 | 1997-04-22 | Mitsui Petrochem Ind Ltd | α−オレフインの重合方法 |
JP2001114811A (ja) * | 1999-10-15 | 2001-04-24 | Idemitsu Petrochem Co Ltd | オレフィン重合用触媒及びオレフィン重合体の製造方法 |
JP2001151816A (ja) * | 1999-11-25 | 2001-06-05 | Japan Polychem Corp | プロピレン系重合体およびその製造方法 |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009057747A1 (ja) * | 2007-11-01 | 2009-05-07 | Mitsui Chemicals, Inc. | 固体状チタン触媒成分、オレフィン重合用触媒およびオレフィンの重合方法 |
JP5457835B2 (ja) * | 2007-11-01 | 2014-04-02 | 三井化学株式会社 | 固体状チタン触媒成分、オレフィン重合用触媒およびオレフィンの重合方法 |
US8822366B2 (en) | 2007-11-01 | 2014-09-02 | Mitsui Chemicals, Inc. | Solid titanium catalyst component, catalyst for olefin polymerization and process for polymerizing olefin |
KR101228202B1 (ko) * | 2007-11-27 | 2013-01-30 | 미쓰이 가가쿠 가부시키가이샤 | 고체상 타이타늄 촉매 성분, 올레핀 중합용 촉매 및 올레핀의 중합 방법 |
JP2013516535A (ja) * | 2010-01-13 | 2013-05-13 | サムスン トータル ペトロケミカルズ カンパニー リミテッド | プロピレン重合用固体触媒の製造方法及びそれによって製造された触媒 |
JP2014009359A (ja) * | 2012-06-27 | 2014-01-20 | Samsung Total Petrochemicals Co Ltd | プロピレン重合用固体触媒およびこれを用いたポリプロピレン製造方法 |
Also Published As
Publication number | Publication date |
---|---|
EP1613670A1 (en) | 2006-01-11 |
JP4624986B2 (ja) | 2011-02-02 |
US20140171294A1 (en) | 2014-06-19 |
EP2261267B1 (en) | 2017-05-10 |
WO2004087771A1 (en) | 2004-10-14 |
CN1771268A (zh) | 2006-05-10 |
US20080113860A1 (en) | 2008-05-15 |
EP2261267A2 (en) | 2010-12-15 |
EP1613670B1 (en) | 2017-05-10 |
CN101117364A (zh) | 2008-02-06 |
US8716514B2 (en) | 2014-05-06 |
EP2261267A3 (en) | 2012-01-25 |
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