JP6026662B2 - 固体形態の有機金属化合物を調製するプロセス、およびその使用により触媒組成物および触媒系を調製するプロセス - Google Patents
固体形態の有機金属化合物を調製するプロセス、およびその使用により触媒組成物および触媒系を調製するプロセス Download PDFInfo
- Publication number
- JP6026662B2 JP6026662B2 JP2015528002A JP2015528002A JP6026662B2 JP 6026662 B2 JP6026662 B2 JP 6026662B2 JP 2015528002 A JP2015528002 A JP 2015528002A JP 2015528002 A JP2015528002 A JP 2015528002A JP 6026662 B2 JP6026662 B2 JP 6026662B2
- Authority
- JP
- Japan
- Prior art keywords
- magnesium
- group
- chloride
- titanium
- transition metal
- 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.)
- Active
Links
- 239000003054 catalyst Substances 0.000 title claims description 107
- 239000007787 solid Substances 0.000 title claims description 64
- 239000000203 mixture Substances 0.000 title claims description 57
- 238000004519 manufacturing process Methods 0.000 title claims description 17
- 150000002902 organometallic compounds Chemical class 0.000 title description 3
- 239000011777 magnesium Substances 0.000 claims description 99
- 238000000034 method Methods 0.000 claims description 85
- 229910052749 magnesium Inorganic materials 0.000 claims description 80
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 76
- 230000008569 process Effects 0.000 claims description 70
- -1 alkyl radicals Chemical class 0.000 claims description 66
- 239000010936 titanium Substances 0.000 claims description 46
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 42
- 150000004820 halides Chemical group 0.000 claims description 42
- 229910052719 titanium Inorganic materials 0.000 claims description 42
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 40
- 238000006116 polymerization reaction Methods 0.000 claims description 37
- 239000002243 precursor Substances 0.000 claims description 36
- 150000001336 alkenes Chemical class 0.000 claims description 34
- 150000002901 organomagnesium compounds Chemical class 0.000 claims description 34
- 229910052723 transition metal Inorganic materials 0.000 claims description 32
- 239000003795 chemical substances by application Substances 0.000 claims description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
- 125000002734 organomagnesium group Chemical group 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 25
- 230000015572 biosynthetic process Effects 0.000 claims description 24
- 150000003624 transition metals Chemical class 0.000 claims description 24
- 150000002430 hydrocarbons Chemical group 0.000 claims description 23
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 20
- 238000003786 synthesis reaction Methods 0.000 claims description 20
- 150000003609 titanium compounds Chemical class 0.000 claims description 17
- 229930195733 hydrocarbon Natural products 0.000 claims description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 10
- 150000003623 transition metal compounds Chemical class 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 238000001556 precipitation Methods 0.000 claims description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 230000000379 polymerizing effect Effects 0.000 claims description 7
- 239000008096 xylene Substances 0.000 claims description 7
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 6
- 150000001350 alkyl halides Chemical class 0.000 claims description 6
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 6
- MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical compound CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 6
- 239000011949 solid catalyst Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 4
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 claims description 4
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 claims description 4
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 4
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 4
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 claims description 4
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 claims description 4
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 claims description 4
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Chemical compound CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 claims description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 4
- FHUODBDRWMIBQP-UHFFFAOYSA-N Ethyl p-anisate Chemical compound CCOC(=O)C1=CC=C(OC)C=C1 FHUODBDRWMIBQP-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 4
- 229940073608 benzyl chloride Drugs 0.000 claims description 4
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims description 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 4
- 150000004678 hydrides Chemical class 0.000 claims description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 4
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 claims description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical group COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 4
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 4
- 239000002002 slurry Substances 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical group Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 3
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 claims description 3
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 claims description 3
- NTWOIGOPFDMZAE-UHFFFAOYSA-M CCO[Ti](Cl)(OCC)OCC Chemical compound CCO[Ti](Cl)(OCC)OCC NTWOIGOPFDMZAE-UHFFFAOYSA-M 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000012662 bulk polymerization Methods 0.000 claims description 3
- 229940117389 dichlorobenzene Drugs 0.000 claims description 3
- 150000002009 diols Chemical class 0.000 claims description 3
- XGZNHFPFJRZBBT-UHFFFAOYSA-N ethanol;titanium Chemical compound [Ti].CCO.CCO.CCO.CCO XGZNHFPFJRZBBT-UHFFFAOYSA-N 0.000 claims description 3
- RMTCVMQBBYEAPC-UHFFFAOYSA-K ethanolate;titanium(4+);trichloride Chemical compound [Cl-].[Cl-].[Cl-].CCO[Ti+3] RMTCVMQBBYEAPC-UHFFFAOYSA-K 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000012456 homogeneous solution Substances 0.000 claims description 3
- 229910001502 inorganic halide Inorganic materials 0.000 claims description 3
- 239000003350 kerosene Substances 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 3
- OKENUZUGNVCOMC-UHFFFAOYSA-K methanolate titanium(4+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].CO[Ti+3] OKENUZUGNVCOMC-UHFFFAOYSA-K 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- 150000003900 succinic acid esters Chemical class 0.000 claims description 3
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 claims description 3
- NLLZTRMHNHVXJJ-UHFFFAOYSA-J titanium tetraiodide Chemical compound I[Ti](I)(I)I NLLZTRMHNHVXJJ-UHFFFAOYSA-J 0.000 claims description 3
- WIHMGGWNMISDNJ-UHFFFAOYSA-N 1,1-dichloropropane Chemical compound CCC(Cl)Cl WIHMGGWNMISDNJ-UHFFFAOYSA-N 0.000 claims description 2
- YHRUOJUYPBUZOS-UHFFFAOYSA-N 1,3-dichloropropane Chemical compound ClCCCCl YHRUOJUYPBUZOS-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- KJDRSWPQXHESDQ-UHFFFAOYSA-N 1,4-dichlorobutane Chemical compound ClCCCCCl KJDRSWPQXHESDQ-UHFFFAOYSA-N 0.000 claims description 2
- LBKDGROORAKTLC-UHFFFAOYSA-N 1,5-dichloropentane Chemical compound ClCCCCCCl LBKDGROORAKTLC-UHFFFAOYSA-N 0.000 claims description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 2
- GPCJORQWYXQSJB-UHFFFAOYSA-N 1-chloro-8-iodooctane Chemical compound ClCCCCCCCCI GPCJORQWYXQSJB-UHFFFAOYSA-N 0.000 claims description 2
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 claims description 2
- RQUBQBFVDOLUKC-UHFFFAOYSA-N 1-ethoxy-2-methylpropane Chemical compound CCOCC(C)C RQUBQBFVDOLUKC-UHFFFAOYSA-N 0.000 claims description 2
- PZHIWRCQKBBTOW-UHFFFAOYSA-N 1-ethoxybutane Chemical compound CCCCOCC PZHIWRCQKBBTOW-UHFFFAOYSA-N 0.000 claims description 2
- ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical compound COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 claims description 2
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 claims description 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 2
- NFRKUDYZEVQXTE-UHFFFAOYSA-N 2-chloropentane Chemical compound CCCC(C)Cl NFRKUDYZEVQXTE-UHFFFAOYSA-N 0.000 claims description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 2
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 claims description 2
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 claims description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 2
- FUZLRTGGPPIBJQ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n-tetramethylpyrimidine-2,4-diamine Chemical compound CN(C)C1=CC=NC(N(C)C)=N1 FUZLRTGGPPIBJQ-UHFFFAOYSA-N 0.000 claims description 2
- BHPDSAAGSUWVMP-UHFFFAOYSA-N 3,3-bis(methoxymethyl)-2,6-dimethylheptane Chemical compound COCC(C(C)C)(COC)CCC(C)C BHPDSAAGSUWVMP-UHFFFAOYSA-N 0.000 claims description 2
- CXQSCYIVCSCSES-UHFFFAOYSA-N 3-chloropentane Chemical compound CCC(Cl)CC CXQSCYIVCSCSES-UHFFFAOYSA-N 0.000 claims description 2
- PVWCLOAAEFMTLH-UHFFFAOYSA-N 4,4-bis(methoxymethyl)-2,6-dimethylheptane Chemical compound COCC(COC)(CC(C)C)CC(C)C PVWCLOAAEFMTLH-UHFFFAOYSA-N 0.000 claims description 2
- SIXWIUJQBBANGK-UHFFFAOYSA-N 4-(4-fluorophenyl)-1h-pyrazol-5-amine Chemical compound N1N=CC(C=2C=CC(F)=CC=2)=C1N SIXWIUJQBBANGK-UHFFFAOYSA-N 0.000 claims description 2
- HRAQMGWTPNOILP-UHFFFAOYSA-N 4-Ethoxy ethylbenzoate Chemical compound CCOC(=O)C1=CC=C(OCC)C=C1 HRAQMGWTPNOILP-UHFFFAOYSA-N 0.000 claims description 2
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 claims description 2
- DNZXTVCIOVBBGV-UHFFFAOYSA-N 5,5-bis(methoxymethyl)-2,8-dimethylnonane Chemical compound CC(C)CCC(COC)(CCC(C)C)COC DNZXTVCIOVBBGV-UHFFFAOYSA-N 0.000 claims description 2
- FXBITRHTKQZLRX-UHFFFAOYSA-N 7-chloroheptanenitrile Chemical compound ClCCCCCCC#N FXBITRHTKQZLRX-UHFFFAOYSA-N 0.000 claims description 2
- ZWINORFLMHROGF-UHFFFAOYSA-N 9,9-bis(methoxymethyl)fluorene Chemical group C1=CC=C2C(COC)(COC)C3=CC=CC=C3C2=C1 ZWINORFLMHROGF-UHFFFAOYSA-N 0.000 claims description 2
- FFYKQJQYGLFCHQ-UHFFFAOYSA-N 9-chloro-9-ethyl-6-methylicosane Chemical compound ClC(CCC(CCCCC)C)(CCCCCCCCCCC)CC FFYKQJQYGLFCHQ-UHFFFAOYSA-N 0.000 claims description 2
- MVECFARLYQAUNR-UHFFFAOYSA-N CCCC[Mg]CC Chemical compound CCCC[Mg]CC MVECFARLYQAUNR-UHFFFAOYSA-N 0.000 claims description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 2
- 239000004803 Di-2ethylhexylphthalate Substances 0.000 claims description 2
- YUXIBTJKHLUKBD-UHFFFAOYSA-N Dibutyl succinate Chemical compound CCCCOC(=O)CCC(=O)OCCCC YUXIBTJKHLUKBD-UHFFFAOYSA-N 0.000 claims description 2
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 claims description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 2
- LMXFTMYMHGYJEI-UHFFFAOYSA-N Menthoglycol Natural products CC1CCC(C(C)(C)O)C(O)C1 LMXFTMYMHGYJEI-UHFFFAOYSA-N 0.000 claims description 2
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 claims description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 229910021607 Silver chloride Inorganic materials 0.000 claims description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- PQIDFVXMOZQINS-UHFFFAOYSA-N [1-methoxy-2-(methoxymethyl)-3-methylbutan-2-yl]cyclohexane Chemical compound COCC(COC)(C(C)C)C1CCCCC1 PQIDFVXMOZQINS-UHFFFAOYSA-N 0.000 claims description 2
- GUMQWPGMMSFQEQ-UHFFFAOYSA-M [I-].CC(C)(C)[Mg+] Chemical compound [I-].CC(C)(C)[Mg+] GUMQWPGMMSFQEQ-UHFFFAOYSA-M 0.000 claims description 2
- XMRNQLVCJLGBDQ-UHFFFAOYSA-M [I-].CC(C)C[Mg+] Chemical compound [I-].CC(C)C[Mg+] XMRNQLVCJLGBDQ-UHFFFAOYSA-M 0.000 claims description 2
- CDKFWIMBZAUBRS-UHFFFAOYSA-M [I-].CC[Mg+] Chemical compound [I-].CC[Mg+] CDKFWIMBZAUBRS-UHFFFAOYSA-M 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 2
- UDEWPOVQBGFNGE-UHFFFAOYSA-N benzoic acid n-propyl ester Natural products CCCOC(=O)C1=CC=CC=C1 UDEWPOVQBGFNGE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052790 beryllium Inorganic materials 0.000 claims description 2
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- QCOAPBRVQHMEPF-UHFFFAOYSA-N bis(2-methylpropyl) butanedioate Chemical compound CC(C)COC(=O)CCC(=O)OCC(C)C QCOAPBRVQHMEPF-UHFFFAOYSA-N 0.000 claims description 2
- YIEMNXLZDZBWQU-UHFFFAOYSA-N bis(7-methyloctan-2-yl) cyclohexane-1,2-dicarboxylate Chemical compound C1(C(CCCC1)C(=O)OC(C)CCCCC(C)C)C(=O)OC(C)CCCCC(C)C YIEMNXLZDZBWQU-UHFFFAOYSA-N 0.000 claims description 2
- DEFMLLQRTVNBOF-UHFFFAOYSA-K butan-1-olate;trichlorotitanium(1+) Chemical compound [Cl-].[Cl-].[Cl-].CCCCO[Ti+3] DEFMLLQRTVNBOF-UHFFFAOYSA-K 0.000 claims description 2
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052793 cadmium Inorganic materials 0.000 claims description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical group [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 claims description 2
- NDTCXABJQNJPCF-UHFFFAOYSA-N chlorocyclopentane Chemical compound ClC1CCCC1 NDTCXABJQNJPCF-UHFFFAOYSA-N 0.000 claims description 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 2
- DQZKGSRJOUYVPL-UHFFFAOYSA-N cyclohexyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1CCCCC1 DQZKGSRJOUYVPL-UHFFFAOYSA-N 0.000 claims description 2
- 229960002097 dibutylsuccinate Drugs 0.000 claims description 2
- RPNFNBGRHCUORR-UHFFFAOYSA-N diethyl 2-butylpropanedioate Chemical compound CCCCC(C(=O)OCC)C(=O)OCC RPNFNBGRHCUORR-UHFFFAOYSA-N 0.000 claims description 2
- VQAZCUCWHIIFGE-UHFFFAOYSA-N diethyl 2-ethylpropanedioate Chemical compound CCOC(=O)C(CC)C(=O)OCC VQAZCUCWHIIFGE-UHFFFAOYSA-N 0.000 claims description 2
- BYQFBFWERHXONI-UHFFFAOYSA-N diethyl 2-propan-2-ylpropanedioate Chemical compound CCOC(=O)C(C(C)C)C(=O)OCC BYQFBFWERHXONI-UHFFFAOYSA-N 0.000 claims description 2
- GRRSDGHTSMJICM-UHFFFAOYSA-N diethyl 2-propylpropanedioate Chemical compound CCOC(=O)C(CCC)C(=O)OCC GRRSDGHTSMJICM-UHFFFAOYSA-N 0.000 claims description 2
- ZTUZDYWYNQDJKR-UHFFFAOYSA-N diethyl cyclohexane-1,2-dicarboxylate Chemical group CCOC(=O)C1CCCCC1C(=O)OCC ZTUZDYWYNQDJKR-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- KZLUHGRPVSRSHI-UHFFFAOYSA-N dimethylmagnesium Chemical compound C[Mg]C KZLUHGRPVSRSHI-UHFFFAOYSA-N 0.000 claims description 2
- YPLYFEUBZLLLIY-UHFFFAOYSA-N dipropan-2-yl butanedioate Chemical compound CC(C)OC(=O)CCC(=O)OC(C)C YPLYFEUBZLLLIY-UHFFFAOYSA-N 0.000 claims description 2
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 claims description 2
- ZLRROLLKQDRDPI-UHFFFAOYSA-L disodium;4,5-dihydroxybenzene-1,3-disulfonate;hydrate Chemical compound O.[Na+].[Na+].OC1=CC(S([O-])(=O)=O)=CC(S([O-])(=O)=O)=C1O ZLRROLLKQDRDPI-UHFFFAOYSA-L 0.000 claims description 2
- SNRUBQQJIBEYMU-NJFSPNSNSA-N dodecane Chemical class CCCCCCCCCCC[14CH3] SNRUBQQJIBEYMU-NJFSPNSNSA-N 0.000 claims description 2
- 229960003750 ethyl chloride Drugs 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical class CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims description 2
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- DQDWATOXYCARFV-UHFFFAOYSA-M magnesium;2-methanidylpropane;bromide Chemical compound [Mg+2].[Br-].CC(C)[CH2-] DQDWATOXYCARFV-UHFFFAOYSA-M 0.000 claims description 2
- YSMZEMQBSONIMJ-UHFFFAOYSA-M magnesium;2-methanidylpropane;chloride Chemical compound [Mg+2].[Cl-].CC(C)[CH2-] YSMZEMQBSONIMJ-UHFFFAOYSA-M 0.000 claims description 2
- UKZCGMDMXDLAGZ-UHFFFAOYSA-M magnesium;2-methylpropane;bromide Chemical compound [Mg+2].[Br-].C[C-](C)C UKZCGMDMXDLAGZ-UHFFFAOYSA-M 0.000 claims description 2
- CQRPUKWAZPZXTO-UHFFFAOYSA-M magnesium;2-methylpropane;chloride Chemical compound [Mg+2].[Cl-].C[C-](C)C CQRPUKWAZPZXTO-UHFFFAOYSA-M 0.000 claims description 2
- KJJBSBKRXUVBMX-UHFFFAOYSA-N magnesium;butane Chemical compound [Mg+2].CCC[CH2-].CCC[CH2-] KJJBSBKRXUVBMX-UHFFFAOYSA-N 0.000 claims description 2
- KXDANLFHGCWFRQ-UHFFFAOYSA-N magnesium;butane;octane Chemical compound [Mg+2].CCC[CH2-].CCCCCCC[CH2-] KXDANLFHGCWFRQ-UHFFFAOYSA-N 0.000 claims description 2
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 claims description 2
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical group [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 claims description 2
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 claims description 2
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 claims description 2
- YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 claims description 2
- RVOYYLUVELMWJF-UHFFFAOYSA-N magnesium;hexane Chemical compound [Mg+2].CCCCC[CH2-].CCCCC[CH2-] RVOYYLUVELMWJF-UHFFFAOYSA-N 0.000 claims description 2
- LZFCBBSYZJPPIV-UHFFFAOYSA-M magnesium;hexane;bromide Chemical compound [Mg+2].[Br-].CCCCC[CH2-] LZFCBBSYZJPPIV-UHFFFAOYSA-M 0.000 claims description 2
- QGEFGPVWRJCFQP-UHFFFAOYSA-M magnesium;methanidylbenzene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C1=CC=CC=C1 QGEFGPVWRJCFQP-UHFFFAOYSA-M 0.000 claims description 2
- SCEZYJKGDJPHQO-UHFFFAOYSA-M magnesium;methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC=C1 SCEZYJKGDJPHQO-UHFFFAOYSA-M 0.000 claims description 2
- KMYFNYFIPIGQQZ-UHFFFAOYSA-N magnesium;octane Chemical compound [Mg+2].CCCCCCC[CH2-].CCCCCCC[CH2-] KMYFNYFIPIGQQZ-UHFFFAOYSA-N 0.000 claims description 2
- DQZLQYHGCKLKGU-UHFFFAOYSA-N magnesium;propane Chemical compound [Mg+2].C[CH-]C.C[CH-]C DQZLQYHGCKLKGU-UHFFFAOYSA-N 0.000 claims description 2
- XGITVAYMIKUXIN-UHFFFAOYSA-M magnesium;propane;iodide Chemical compound [Mg+2].[I-].C[CH-]C XGITVAYMIKUXIN-UHFFFAOYSA-M 0.000 claims description 2
- WVWZECQNFWFVFW-UHFFFAOYSA-N methyl 2-methylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C WVWZECQNFWFVFW-UHFFFAOYSA-N 0.000 claims description 2
- 229940095102 methyl benzoate Drugs 0.000 claims description 2
- DDIZAANNODHTRB-UHFFFAOYSA-N methyl p-anisate Chemical compound COC(=O)C1=CC=C(OC)C=C1 DDIZAANNODHTRB-UHFFFAOYSA-N 0.000 claims description 2
- OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 claims description 2
- UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 2
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 claims description 2
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 claims description 2
- YKNWIILGEFFOPE-UHFFFAOYSA-N pentacosane Chemical class CCCCCCCCCCCCCCCCCCCCCCCCC YKNWIILGEFFOPE-UHFFFAOYSA-N 0.000 claims description 2
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 claims description 2
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 claims description 2
- 150000003003 phosphines Chemical class 0.000 claims description 2
- 125000005498 phthalate group Chemical class 0.000 claims description 2
- JQCXWCOOWVGKMT-UHFFFAOYSA-N phthalic acid diheptyl ester Natural products CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC JQCXWCOOWVGKMT-UHFFFAOYSA-N 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 235000013772 propylene glycol Nutrition 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 238000005185 salting out Methods 0.000 claims description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 claims description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 2
- 150000003871 sulfonates Chemical class 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- 150000003462 sulfoxides Chemical class 0.000 claims description 2
- CRNIHJHMEQZAAS-UHFFFAOYSA-N tert-amyl chloride Chemical compound CCC(C)(C)Cl CRNIHJHMEQZAAS-UHFFFAOYSA-N 0.000 claims description 2
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 claims description 2
- BGHCVCJVXZWKCC-NJFSPNSNSA-N tetradecane Chemical class CCCCCCCCCCCCC[14CH3] BGHCVCJVXZWKCC-NJFSPNSNSA-N 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- LGWZGBCKVDSYPH-UHFFFAOYSA-N triacontane Chemical class [CH2]CCCCCCCCCCCCCCCCCCCCCCCCCCCCC LGWZGBCKVDSYPH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 4
- QUYFPNWYGLFQQU-UHFFFAOYSA-N 5-methyldecane Chemical compound CCCCCC(C)CCCC QUYFPNWYGLFQQU-UHFFFAOYSA-N 0.000 claims 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims 1
- FMGGHNGKHRCJLL-UHFFFAOYSA-N 1,2-bis(chloromethyl)benzene Chemical group ClCC1=CC=CC=C1CCl FMGGHNGKHRCJLL-UHFFFAOYSA-N 0.000 claims 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims 1
- SFGBOBMTMFHZJH-UHFFFAOYSA-N 1-chloro-6-methylheptane Chemical compound CC(C)CCCCCCl SFGBOBMTMFHZJH-UHFFFAOYSA-N 0.000 claims 1
- ZVERWTXKKWSSHH-UHFFFAOYSA-N 4-propan-2-yloxybenzoic acid Chemical compound CC(C)OC1=CC=C(C(O)=O)C=C1 ZVERWTXKKWSSHH-UHFFFAOYSA-N 0.000 claims 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- IYGZPNSIEQRRIL-UHFFFAOYSA-M [I-].[Mg+]CC1=CC=CC=C1 Chemical compound [I-].[Mg+]CC1=CC=CC=C1 IYGZPNSIEQRRIL-UHFFFAOYSA-M 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 150000004792 aryl magnesium halides Chemical class 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 235000019445 benzyl alcohol Nutrition 0.000 claims 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 claims 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 claims 1
- DROMNWUQASBTFM-UHFFFAOYSA-N dinonyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCC DROMNWUQASBTFM-UHFFFAOYSA-N 0.000 claims 1
- UHSDHNXHBQDMMH-UHFFFAOYSA-L ethanolate;titanium(4+);dichloride Chemical group CCO[Ti](Cl)(Cl)OCC UHSDHNXHBQDMMH-UHFFFAOYSA-L 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 150000001469 hydantoins Chemical class 0.000 claims 1
- DLPASUVGCQPFFO-UHFFFAOYSA-N magnesium;ethane Chemical compound [Mg+2].[CH2-]C.[CH2-]C DLPASUVGCQPFFO-UHFFFAOYSA-N 0.000 claims 1
- LVKCSZQWLOVUGB-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].C[CH-]C LVKCSZQWLOVUGB-UHFFFAOYSA-M 0.000 claims 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 1
- 235000021317 phosphate Nutrition 0.000 claims 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 150000002681 magnesium compounds Chemical class 0.000 description 13
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 13
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- 239000011954 Ziegler–Natta catalyst Substances 0.000 description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 9
- 239000005977 Ethylene Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 229910052735 hafnium Inorganic materials 0.000 description 9
- 229910052720 vanadium Inorganic materials 0.000 description 9
- 229910052726 zirconium Inorganic materials 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 229920000098 polyolefin Polymers 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- 239000012433 hydrogen halide Substances 0.000 description 4
- 229910000039 hydrogen halide Inorganic materials 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000002685 polymerization catalyst Substances 0.000 description 4
- 125000005234 alkyl aluminium group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 3
- 239000004711 α-olefin Substances 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 2
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002879 Lewis base Substances 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000004708 Very-low-density polyethylene Substances 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- SJJCABYOVIHNPZ-UHFFFAOYSA-N cyclohexyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C1CCCCC1 SJJCABYOVIHNPZ-UHFFFAOYSA-N 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- NSYCXGBGJZBZKI-UHFFFAOYSA-L dichlorotitanium;ethanol Chemical group CCO.CCO.Cl[Ti]Cl NSYCXGBGJZBZKI-UHFFFAOYSA-L 0.000 description 2
- JWCYDYZLEAQGJJ-UHFFFAOYSA-N dicyclopentyl(dimethoxy)silane Chemical compound C1CCCC1[Si](OC)(OC)C1CCCC1 JWCYDYZLEAQGJJ-UHFFFAOYSA-N 0.000 description 2
- YQGOWXYZDLJBFL-UHFFFAOYSA-N dimethoxysilane Chemical compound CO[SiH2]OC YQGOWXYZDLJBFL-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- MGDOJPNDRJNJBK-UHFFFAOYSA-N ethylaluminum Chemical compound [Al].C[CH2] MGDOJPNDRJNJBK-UHFFFAOYSA-N 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- 229920001903 high density polyethylene Polymers 0.000 description 2
- 239000004700 high-density polyethylene Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 229920001580 isotactic polymer Polymers 0.000 description 2
- 150000007527 lewis bases Chemical class 0.000 description 2
- 150000002680 magnesium Chemical class 0.000 description 2
- 235000011147 magnesium chloride Nutrition 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000003495 polar organic solvent Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZLMGMVJGEULFPP-UHFFFAOYSA-J titanium(4+) trichloride phenoxide Chemical compound Cl[Ti](Cl)(Cl)OC1=CC=CC=C1 ZLMGMVJGEULFPP-UHFFFAOYSA-J 0.000 description 2
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 2
- 229920001866 very low density polyethylene Polymers 0.000 description 2
- WCFQIFDACWBNJT-UHFFFAOYSA-N $l^{1}-alumanyloxy(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]O[Al] WCFQIFDACWBNJT-UHFFFAOYSA-N 0.000 description 1
- SXNLMXPRYYYOSO-UHFFFAOYSA-N (2,3-dimethylcyclopentyl)-trimethoxysilane Chemical compound CO[Si](OC)(OC)C1CCC(C)C1C SXNLMXPRYYYOSO-UHFFFAOYSA-N 0.000 description 1
- TUDQZWSZMFQUBS-UHFFFAOYSA-N (2,5-dimethylcyclopentyl)-trimethoxysilane Chemical compound CO[Si](OC)(OC)C1C(C)CCC1C TUDQZWSZMFQUBS-UHFFFAOYSA-N 0.000 description 1
- YQXKUILMUQPCPU-UHFFFAOYSA-N 2,2,2-tricyclopentylethoxysilane Chemical compound C1CCCC1C(C1CCCC1)(CO[SiH3])C1CCCC1 YQXKUILMUQPCPU-UHFFFAOYSA-N 0.000 description 1
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 description 1
- HXLAEGYMDGUSBD-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN HXLAEGYMDGUSBD-UHFFFAOYSA-N 0.000 description 1
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- GXNMWIOLHVTXBK-UHFFFAOYSA-N 5-chloro-5-methyldecane Chemical compound CCCCCC(C)(Cl)CCCC GXNMWIOLHVTXBK-UHFFFAOYSA-N 0.000 description 1
- RQHRDLRTRXSOBY-UHFFFAOYSA-N 9h-fluoren-1-yl-(1h-inden-1-yl)-dimethoxysilane Chemical compound C1C2=CC=CC=C2C2=C1C([Si](OC)(C1C3=CC=CC=C3C=C1)OC)=CC=C2 RQHRDLRTRXSOBY-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VJDVCMFKVTWCCA-UHFFFAOYSA-N C1(C=CC=C1)[Si](OC)(OC)C1C=CC2=CC=CC=C12 Chemical compound C1(C=CC=C1)[Si](OC)(OC)C1C=CC2=CC=CC=C12 VJDVCMFKVTWCCA-UHFFFAOYSA-N 0.000 description 1
- VQDGVBRKMCJOTD-UHFFFAOYSA-N C1(CCCC1)[Si](OC)(OC)C1C=CC=C1 Chemical compound C1(CCCC1)[Si](OC)(OC)C1C=CC=C1 VQDGVBRKMCJOTD-UHFFFAOYSA-N 0.000 description 1
- PSXLCTPHDAEPLK-UHFFFAOYSA-N CC(C)[Mg] Chemical compound CC(C)[Mg] PSXLCTPHDAEPLK-UHFFFAOYSA-N 0.000 description 1
- LVKGXKTYGHIATJ-UHFFFAOYSA-N CCCCC(CC)C(CC)OC(C1(CCCCC1)C(O)=O)=O Chemical compound CCCCC(CC)C(CC)OC(C1(CCCCC1)C(O)=O)=O LVKGXKTYGHIATJ-UHFFFAOYSA-N 0.000 description 1
- RASBDVLERRNNLJ-UHFFFAOYSA-N CCCCO[Ti] Chemical compound CCCCO[Ti] RASBDVLERRNNLJ-UHFFFAOYSA-N 0.000 description 1
- FEMZNOOBXHLPFP-UHFFFAOYSA-N CCO[SiH](OCC)CC(C)(C)CC Chemical compound CCO[SiH](OCC)CC(C)(C)CC FEMZNOOBXHLPFP-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-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
- GUDBSTJKAWCJQP-UHFFFAOYSA-N [Mg]CC1=CC=CC=C1 Chemical compound [Mg]CC1=CC=CC=C1 GUDBSTJKAWCJQP-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- DEKYCKZXEQLEEJ-UHFFFAOYSA-N bis(2,3-dimethylcyclopentyl)-dimethoxysilane Chemical compound C1CC(C)C(C)C1[Si](OC)(OC)C1CCC(C)C1C DEKYCKZXEQLEEJ-UHFFFAOYSA-N 0.000 description 1
- DNOZBDGJLZXQIQ-UHFFFAOYSA-N bis(2,5-dimethylcyclopent-3-en-1-yl)-dimethoxysilane Chemical compound CC1C=CC(C)C1[Si](OC)(OC)C1C(C)C=CC1C DNOZBDGJLZXQIQ-UHFFFAOYSA-N 0.000 description 1
- BSFTTXIBGVMKCF-UHFFFAOYSA-N bis(2,5-dimethylcyclopentyl)-dimethoxysilane Chemical compound CC1CCC(C)C1[Si](OC)(OC)C1C(C)CCC1C BSFTTXIBGVMKCF-UHFFFAOYSA-N 0.000 description 1
- XMBQAUOJKIQYHZ-UHFFFAOYSA-N bis(2-cyclopentylpropan-2-yl)-dimethoxysilane Chemical compound C1CCCC1C(C)(C)[Si](OC)(OC)C(C)(C)C1CCCC1 XMBQAUOJKIQYHZ-UHFFFAOYSA-N 0.000 description 1
- HQMRIBYCTLBDAK-UHFFFAOYSA-M bis(2-methylpropyl)alumanylium;chloride Chemical compound CC(C)C[Al](Cl)CC(C)C HQMRIBYCTLBDAK-UHFFFAOYSA-M 0.000 description 1
- YKCNYZDXCPLTBK-UHFFFAOYSA-N bis(3-tert-butylcyclopentyl)-dimethoxysilane Chemical compound C1CC(C(C)(C)C)CC1[Si](OC)(OC)C1CCC(C(C)(C)C)C1 YKCNYZDXCPLTBK-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- KVCNVTICIMHGNP-UHFFFAOYSA-N butane-1,4-diol;propane-1,3-diol Chemical compound OCCCO.OCCCCO KVCNVTICIMHGNP-UHFFFAOYSA-N 0.000 description 1
- XGZGKDQVCBHSGI-UHFFFAOYSA-N butyl(triethoxy)silane Chemical compound CCCC[Si](OCC)(OCC)OCC XGZGKDQVCBHSGI-UHFFFAOYSA-N 0.000 description 1
- OCFSGVNHPVWWKD-UHFFFAOYSA-N butylaluminum Chemical compound [Al].[CH2]CCC OCFSGVNHPVWWKD-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- JEZFASCUIZYYEV-UHFFFAOYSA-N chloro(triethoxy)silane Chemical compound CCO[Si](Cl)(OCC)OCC JEZFASCUIZYYEV-UHFFFAOYSA-N 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- CCRJEJIPEOBMFG-UHFFFAOYSA-N cyclobutyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C1CCC1 CCRJEJIPEOBMFG-UHFFFAOYSA-N 0.000 description 1
- CURJWPPVLYJSIX-UHFFFAOYSA-N cyclobutyl-cyclopropyl-diethoxysilane Chemical compound C1CCC1[Si](OCC)(OCC)C1CC1 CURJWPPVLYJSIX-UHFFFAOYSA-N 0.000 description 1
- ATGKAFZFOALBOF-UHFFFAOYSA-N cyclohexyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C1CCCCC1 ATGKAFZFOALBOF-UHFFFAOYSA-N 0.000 description 1
- RTYZQVDVGVAXSW-UHFFFAOYSA-N cyclohexylmethyl(diethoxy)silane Chemical compound CCO[SiH](OCC)CC1CCCCC1 RTYZQVDVGVAXSW-UHFFFAOYSA-N 0.000 description 1
- SMRPGTWKAWGUNE-UHFFFAOYSA-N cyclopent-3-en-1-yl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C1CC=CC1 SMRPGTWKAWGUNE-UHFFFAOYSA-N 0.000 description 1
- NEFYMAXZJXQULZ-UHFFFAOYSA-N cyclopenta-2,4-dien-1-yl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C1C=CC=C1 NEFYMAXZJXQULZ-UHFFFAOYSA-N 0.000 description 1
- VZNFEFZDFPUTFJ-UHFFFAOYSA-N cyclopenten-1-yl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C1=CCCC1 VZNFEFZDFPUTFJ-UHFFFAOYSA-N 0.000 description 1
- FRHGTFOSPGFDIE-UHFFFAOYSA-N cyclopenten-1-yl-cyclopentyl-dimethoxysilane Chemical compound C=1CCCC=1[Si](OC)(OC)C1CCCC1 FRHGTFOSPGFDIE-UHFFFAOYSA-N 0.000 description 1
- FGDHZJKEYPNZAV-UHFFFAOYSA-N cyclopenten-1-ylmethoxy(dicyclopentyl)silane Chemical compound C1(CCCC1)[SiH](OCC1=CCCC1)C1CCCC1 FGDHZJKEYPNZAV-UHFFFAOYSA-N 0.000 description 1
- MGGAITMRMJXXMT-UHFFFAOYSA-N cyclopentyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C1CCCC1 MGGAITMRMJXXMT-UHFFFAOYSA-N 0.000 description 1
- YRMPTIHEUZLTDO-UHFFFAOYSA-N cyclopentyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C1CCCC1 YRMPTIHEUZLTDO-UHFFFAOYSA-N 0.000 description 1
- JEIAREHEXNLWFN-UHFFFAOYSA-N cyclopentyl-(9h-fluoren-1-yl)-dimethoxysilane Chemical compound C=1C=CC(C2=CC=CC=C2C2)=C2C=1[Si](OC)(OC)C1CCCC1 JEIAREHEXNLWFN-UHFFFAOYSA-N 0.000 description 1
- LITADYQPNQQQCR-UHFFFAOYSA-N cyclopentyl-diethyl-methoxysilane Chemical compound CC[Si](CC)(OC)C1CCCC1 LITADYQPNQQQCR-UHFFFAOYSA-N 0.000 description 1
- NGUKXKTXADXBIB-UHFFFAOYSA-N cyclopentyl-ethoxy-dimethylsilane Chemical compound CCO[Si](C)(C)C1CCCC1 NGUKXKTXADXBIB-UHFFFAOYSA-N 0.000 description 1
- BVNCDRJKUJGGTL-UHFFFAOYSA-N cyclopentyl-methoxy-dimethylsilane Chemical compound CO[Si](C)(C)C1CCCC1 BVNCDRJKUJGGTL-UHFFFAOYSA-N 0.000 description 1
- FQYDKXZVLQHDPJ-UHFFFAOYSA-N cyclopentylmethoxy-bis(2,5-dimethylcyclopentyl)silane Chemical compound CC1C(C(CC1)C)[SiH](OCC1CCCC1)C1C(CCC1C)C FQYDKXZVLQHDPJ-UHFFFAOYSA-N 0.000 description 1
- LHMFNXSUCBBOGJ-UHFFFAOYSA-N cyclopentylmethyl(methoxy)silane Chemical compound C1(CCCC1)C[SiH2]OC LHMFNXSUCBBOGJ-UHFFFAOYSA-N 0.000 description 1
- FWCBQAXNMWDAFK-UHFFFAOYSA-N cyclopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C1CC1 FWCBQAXNMWDAFK-UHFFFAOYSA-N 0.000 description 1
- BAAAEEDPKUHLID-UHFFFAOYSA-N decyl(triethoxy)silane Chemical compound CCCCCCCCCC[Si](OCC)(OCC)OCC BAAAEEDPKUHLID-UHFFFAOYSA-N 0.000 description 1
- KQAHMVLQCSALSX-UHFFFAOYSA-N decyl(trimethoxy)silane Chemical compound CCCCCCCCCC[Si](OC)(OC)OC KQAHMVLQCSALSX-UHFFFAOYSA-N 0.000 description 1
- IHUIEBZUNDVFFW-UHFFFAOYSA-N di(cyclobutyl)-diethoxysilane Chemical compound C1CCC1[Si](OCC)(OCC)C1CCC1 IHUIEBZUNDVFFW-UHFFFAOYSA-N 0.000 description 1
- VVXWGMCRFPITIH-UHFFFAOYSA-N di(cyclopent-3-en-1-yl)-dimethoxysilane Chemical compound C1C=CCC1[Si](OC)(OC)C1CC=CC1 VVXWGMCRFPITIH-UHFFFAOYSA-N 0.000 description 1
- YZDFSKMSVNGTNQ-UHFFFAOYSA-N di(cyclopenta-2,4-dien-1-yl)-dimethoxysilane Chemical compound C1=CC=CC1[Si](OC)(OC)C1C=CC=C1 YZDFSKMSVNGTNQ-UHFFFAOYSA-N 0.000 description 1
- VJRUISVXILMZSL-UHFFFAOYSA-M dibutylalumanylium;chloride Chemical compound CCCC[Al](Cl)CCCC VJRUISVXILMZSL-UHFFFAOYSA-M 0.000 description 1
- ZVMRWPHIZSSUKP-UHFFFAOYSA-N dicyclohexyl(dimethoxy)silane Chemical compound C1CCCCC1[Si](OC)(OC)C1CCCCC1 ZVMRWPHIZSSUKP-UHFFFAOYSA-N 0.000 description 1
- FVAXOELGJXMINU-UHFFFAOYSA-N dicyclopentyl(diethoxy)silane Chemical compound C1CCCC1[Si](OCC)(OCC)C1CCCC1 FVAXOELGJXMINU-UHFFFAOYSA-N 0.000 description 1
- RUHGCFSYBXWPNF-UHFFFAOYSA-N dicyclopentylmethyl(ethoxy)silane Chemical compound C1CCCC1C([SiH2]OCC)C1CCCC1 RUHGCFSYBXWPNF-UHFFFAOYSA-N 0.000 description 1
- ZZNQQQWFKKTOSD-UHFFFAOYSA-N diethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OCC)(OCC)C1=CC=CC=C1 ZZNQQQWFKKTOSD-UHFFFAOYSA-N 0.000 description 1
- WCJFZAFGBBIZAA-UHFFFAOYSA-N diethoxy-bis(4-methylphenyl)silane Chemical compound C=1C=C(C)C=CC=1[Si](OCC)(OCC)C1=CC=C(C)C=C1 WCJFZAFGBBIZAA-UHFFFAOYSA-N 0.000 description 1
- HJXBDPDUCXORKZ-UHFFFAOYSA-N diethylalumane Chemical compound CC[AlH]CC HJXBDPDUCXORKZ-UHFFFAOYSA-N 0.000 description 1
- JJSGABFIILQOEY-UHFFFAOYSA-M diethylalumanylium;bromide Chemical compound CC[Al](Br)CC JJSGABFIILQOEY-UHFFFAOYSA-M 0.000 description 1
- LWBWGOJHWAARSS-UHFFFAOYSA-N diethylalumanyloxy(diethyl)alumane Chemical compound CC[Al](CC)O[Al](CC)CC LWBWGOJHWAARSS-UHFFFAOYSA-N 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 1
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 1
- OSZVQUZIQCJAPJ-UHFFFAOYSA-N dimethoxy-bis(2-methylcyclopentyl)silane Chemical compound C1CCC(C)C1[Si](OC)(OC)C1CCCC1C OSZVQUZIQCJAPJ-UHFFFAOYSA-N 0.000 description 1
- AAMBIAPMLISIDH-UHFFFAOYSA-N dimethoxy-bis(2-methylphenyl)silane Chemical compound C=1C=CC=C(C)C=1[Si](OC)(OC)C1=CC=CC=C1C AAMBIAPMLISIDH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- IWEAAVHEPCUQHR-UHFFFAOYSA-N dimethoxy-bis(3-methylphenyl)silane Chemical compound C=1C=CC(C)=CC=1[Si](OC)(OC)C1=CC=CC(C)=C1 IWEAAVHEPCUQHR-UHFFFAOYSA-N 0.000 description 1
- SZIZIGBTHTUEBU-UHFFFAOYSA-N dimethoxy-bis(4-methylphenyl)silane Chemical compound C=1C=C(C)C=CC=1[Si](OC)(OC)C1=CC=C(C)C=C1 SZIZIGBTHTUEBU-UHFFFAOYSA-N 0.000 description 1
- VHPUZTHRFWIGAW-UHFFFAOYSA-N dimethoxy-di(propan-2-yl)silane Chemical compound CO[Si](OC)(C(C)C)C(C)C VHPUZTHRFWIGAW-UHFFFAOYSA-N 0.000 description 1
- CVQVSVBUMVSJES-UHFFFAOYSA-N dimethoxy-methyl-phenylsilane Chemical compound CO[Si](C)(OC)C1=CC=CC=C1 CVQVSVBUMVSJES-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229920001198 elastomeric copolymer Polymers 0.000 description 1
- 229920013728 elastomeric terpolymer Polymers 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- GCPCLEKQVMKXJM-UHFFFAOYSA-N ethoxy(diethyl)alumane Chemical compound CCO[Al](CC)CC GCPCLEKQVMKXJM-UHFFFAOYSA-N 0.000 description 1
- RSIHJDGMBDPTIM-UHFFFAOYSA-N ethoxy(trimethyl)silane Chemical compound CCO[Si](C)(C)C RSIHJDGMBDPTIM-UHFFFAOYSA-N 0.000 description 1
- OKWWGIURLYRQCW-UHFFFAOYSA-N ethyl 4-propan-2-yloxybenzoate Chemical compound CCOC(=O)C1=CC=C(OC(C)C)C=C1 OKWWGIURLYRQCW-UHFFFAOYSA-N 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
- MYEJNNDSIXAGNK-UHFFFAOYSA-N ethyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](CC)(OC(C)C)OC(C)C MYEJNNDSIXAGNK-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229920000092 linear low density polyethylene Polymers 0.000 description 1
- 239000004707 linear low-density polyethylene Substances 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- PBRISDSJNMSBKT-UHFFFAOYSA-N methoxy(penta-1,3-dienyl)silane Chemical compound C(=CC=CC)[SiH2]OC PBRISDSJNMSBKT-UHFFFAOYSA-N 0.000 description 1
- POPACFLNWGUDSR-UHFFFAOYSA-N methoxy(trimethyl)silane Chemical compound CO[Si](C)(C)C POPACFLNWGUDSR-UHFFFAOYSA-N 0.000 description 1
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 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 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 150000004762 orthosilicates Chemical class 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920005606 polypropylene copolymer Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OBRKWFIGZSMARO-UHFFFAOYSA-N propylalumane Chemical compound [AlH2]CCC OBRKWFIGZSMARO-UHFFFAOYSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- ASEHKQZNVUOPRW-UHFFFAOYSA-N tert-butyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C(C)(C)C ASEHKQZNVUOPRW-UHFFFAOYSA-N 0.000 description 1
- JHVNMGWNEQGGDU-UHFFFAOYSA-N tert-butyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(C(C)(C)C)OCC JHVNMGWNEQGGDU-UHFFFAOYSA-N 0.000 description 1
- NETBVGNWMHLXRP-UHFFFAOYSA-N tert-butyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C(C)(C)C NETBVGNWMHLXRP-UHFFFAOYSA-N 0.000 description 1
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 1
- SGCFZHOZKKQIBU-UHFFFAOYSA-N tributoxy(ethenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C=C SGCFZHOZKKQIBU-UHFFFAOYSA-N 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- PTCWADDVLPYBBZ-UHFFFAOYSA-N tricyclopentylmethoxysilane Chemical compound C1CCCC1C(C1CCCC1)(O[SiH3])C1CCCC1 PTCWADDVLPYBBZ-UHFFFAOYSA-N 0.000 description 1
- ALVYUZIFSCKIFP-UHFFFAOYSA-N triethoxy(2-methylpropyl)silane Chemical compound CCO[Si](CC(C)C)(OCC)OCC ALVYUZIFSCKIFP-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-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
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- IOPAQHDEQBHWEB-UHFFFAOYSA-N trimethoxy-(2-methylcyclopentyl)silane Chemical compound CO[Si](OC)(OC)C1CCCC1C IOPAQHDEQBHWEB-UHFFFAOYSA-N 0.000 description 1
- OJAJJFGMKAZGRZ-UHFFFAOYSA-N trimethyl(phenoxy)silane Chemical compound C[Si](C)(C)OC1=CC=CC=C1 OJAJJFGMKAZGRZ-UHFFFAOYSA-N 0.000 description 1
- 229920001862 ultra low molecular weight polyethylene Polymers 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
- C08F4/60—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 refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/65—Pretreating the metal or compound covered by group C08F4/64 before the final contacting with the metal or compound covered by group C08F4/44
- C08F4/652—Pretreating with metals or metal-containing compounds
- C08F4/654—Pretreating with metals or metal-containing compounds with magnesium or compounds thereof
- C08F4/6541—Pretreating with metals or metal-containing compounds with magnesium or compounds thereof and metals of C08F4/64 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
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/10—Magnesium; Oxides or hydroxides thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
- B01J37/0018—Addition of a binding agent or of material, later completely removed among others as result of heat treatment, leaching or washing,(e.g. forming of pores; protective layer, desintegrating by heat)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
-
- 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
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/34—Polymerisation in gaseous state
-
- 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
- C08F4/06—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen
- C08F4/16—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen of silicon, germanium, tin, lead, titanium, zirconium or hafnium
-
- 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
- C08F4/52—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 selected from boron, aluminium, gallium, indium, thallium or rare earths
-
- 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
- C08F4/60—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 refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/65—Pretreating the metal or compound covered by group C08F4/64 before the final contacting with the metal or compound covered by group C08F4/44
- C08F4/652—Pretreating with metals or metal-containing compounds
- C08F4/654—Pretreating with metals or metal-containing compounds with magnesium or compounds thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Description
(a)生成溶液を得るために、M(OR''')pX4−pで表される遷移金属化合物の溶液を、式{Mg(OR')X}.a{MgX2}.b{Mg(OR')2}.c{R'OH}を有する固体の有機マグネシウム前駆体と接触させる。Mは遷移金属であってTi、V、Zr、およびHfから選択され、Mは好ましくはチタニウムであり、Xはハロゲン原子であり、R'''は炭化水素基であり、pは4に等しいか4よりも小さい値を有する整数であり、R'は炭化水素基から選択され、Xはハロゲン化物基から選択され、a:b:cは0.01−0.5:0.01−0.5:0.01−5の範囲内にある。固体の有機マグネシウム前駆体と遷移金属化合物との接触温度は、約−50℃から約150℃の間、好ましくは約−30℃から約120℃の間である。
(b)有機マグネシウム前駆体成分またはチタニウム成分のどちらかに対して内部供与体を添加する。約−50℃から約100℃の間、好ましくは約−30℃から約90℃の間の接触温度において、内部電子供与体との当該成分の接触の時間は、瞬間的であるかまたは少なくとも1分から60分までのどちらかである。
(c)ステップ(a)で得られた生成溶液を、ニートな(neat)チタニウム成分または溶媒中のチタニウム成分を含む溶液で処理し、固体のチタニウム触媒成分を回収し、これを、100から120℃の範囲内の温度値に約10から60分間維持する。
(d)任意で、ステップ(c)を予め定められた回数繰り返し、その後、固体の触媒組成物を得るために、20℃から90℃の温度において不活性溶媒によって十分に洗浄が行われる。
ここで、
Mg − 金属マグネシウム、
RX − ハロゲン化アルキル、
RMgX − グリニャール試薬、
*中間体、
R'OH − アルコール、
a:b:cの比率は0.01−0.5:0.01−0.5:0.01−5の範囲内、
RおよびR'は炭化水素基から選択され、
XはCl、Br、またはIから選択されるハロゲンであり、
nは値1−10を有する整数である。
(a)生成溶液を得るために、M(OR''')pX4−pで表される遷移金属化合物の溶液を、本発明の固体の有機マグネシウム前駆体成分と接触させる。Mは遷移金属であってTi、V、Zr、およびHfを含む群から選択され、好ましくはTiであり、Xはハロゲン原子であり、R'''は炭化水素基であり、pは4に等しいか4よりも小さい値を有する整数である。固体の有機マグネシウム前駆体と遷移金属化合物との接触温度は、約−50℃から約150℃の間、好ましくは約−30℃から約120℃の間である。
(b)固体の有機マグネシウム前駆体成分またはチタニウム成分のどちらかに対して、好ましくは有機マグネシウム化合物に対して内部供与体を添加する。約−50℃から約100℃の間、好ましくは約−30℃から約90℃の間の接触温度において、上記成分の内部電子供与体との接触の時間は、瞬間的であるかまたは少なくとも1分から60分までである。
(c)上記ステップ(a)において得られた生成溶液を、溶媒中のチタニウム成分を含む溶液で処理し、固体のチタニウム触媒成分を回収し、これを約10から60分間、100から120℃の範囲内の温度値に維持する。
(d)任意で、ステップ(c)を予め定められた回数繰り返し、その後、20℃から80℃の温度で不活性溶媒によって十分に洗浄されて、固体の触媒組成物を得る。
(a)遷移金属四ハロゲン化物は、四塩化チタン、四臭化チタン、および四よう化チタン、並びに、V、Zr、およびHfに対するこれらの同等物を含む群から選択される。
(b)アルコキシ遷移金属三ハロゲン化物/アリールオキシ遷移金属三ハロゲン化物は、三塩化メトキシチタン、三塩化エトキシチタン、三塩化ブトキシチタン、および、三塩化フェノキシチタン、並びに、V、Zr、およびHfに対するこれらの同等物を含む群から選択される。
(c)ジアルコキシ遷移金属二ハロゲン化物は、二塩化ジエトキシチタン、並びに、V、Zr、およびHfに対するこの同等物である。
(d)トリアルコキシ遷移金属一ハロゲン化物は、塩化トリエトキシチタン、並びに、V、Zr、およびHfに対するこの同等物である。
(e)テトラアルコキシ遷移金属は、テトラブトキシチタンおよびテトラエトキシチタン、並びに、V、Zr、およびHfに対するこれらの同等物を含む群から選択される。
有機マグネシウム化合物の調製
0℃に維持された500mlガラス反応器中で、計算された量のマグネシウム(粉末または削りくず)が秤量され、反応器へと加えられ、続いてジエチルエーテル、続いて計算された量の有機ハロゲン化物が添加された。この混合物は撹拌され、反応の活性化の後、全てのマグネシウムが反応されるまで、混合物は同じ温度に維持された。生成溶液に対して、計算された量のアルコールが、1−2時間の期間にわたって滴下で加えられた。添加が完了した後、溶液はさらに0.5時間撹拌された。最後に、エーテルが蒸発され、固体の化合物が分析された。
触媒成分の調製
所望温度に維持されたTiCl4溶液60mlに対して、100mlの有機マグネシウム前駆体が内部供与体とともに(ID/Mg=0.11モル)、10分の期間にわたって加えられ、撹拌された。系が所望温度に到達した後、得られた溶液が15分間同じ温度に維持された。得られた溶液はきれいなオレンジ色であった。反応温度が110℃まで徐々に上げられ、1時間維持された。沈降およびデカンテーション後に、懸濁された固体が60mlのTiCl4および60mlのクロロベンゼンで再び処理され、温度が110℃に達した後、混合物は15分間撹拌状態を維持された。上記のステップが再び繰り返された。反応が終了した後、固体はデカンテーションされ、70℃でヘキサンによってそれぞれ十分に洗浄され、自由に流れるまで熱い窒素下でさらに乾燥された。
プロピレンのスラリー重合
窒素下で予め調整された1Lのビューチ(buchi)反応器中でプロピレン重合が実行された。反応器には、10wt%トリエチルアルミニウムの溶液を含む250mlの乾燥ヘキサン、続いてトリエチルアルミニウムの10wt%溶液を含む100mlの乾燥ヘキサン、シクロヘキシルメチルジメトキシシランの5wt%溶液、および秤量された量の触媒が充填された。反応器は60mlまで水素によって加圧され、その後、750rpmでの撹拌下、71psiのプロピレンで充填された。反応器は70℃に加熱され、その後、70℃で2時間維持された。最後に反応器が通気され、ポリマが周囲環境条件で回収された。
Claims (30)
- 式{Mg(OR')X}.a{MgX2}.b{Mg(OR')2}.c{R'OH}を有する固体の有機マグネシウム前駆体を調製するプロセスであって、式中、R'は炭化水素基から選択され、Xはハロゲン化物基から選択され、a:b:cは0.01−0.5:0.01−0.5:0.01−5の範囲内にあり、
前記固体の有機マグネシウム前駆体を得るために、マグネシウム源を、溶媒和剤、有機ハロゲン化物、およびアルコールに接触させるステップを有し、
前記溶媒和剤は、ジメチルエーテル、ジエチルエーテル、ジプロピルエーテル、ジイソプロピルエーテル、エチルメチルエーテル、n−ブチルメチルエーテル、n−ブチルエチルエーテル、ジ−n−ブチルエーテル、ジイソブチルエーテル、イソブチルメチルエーテル、イソブチルエチルエーテル、ジオキサン、テトラヒドロフラン、2−メチルテトラヒドロフラン、テトラヒドロピランおよび、これらの組合わせを含む群から選択され、
前記溶媒和剤との前記マグネシウム源の反応の後に、前記有機ハロゲン化物および前記アルコールの混合物が加えられる、プロセス。 - 沈殿された固体の有機マグネシウム前駆体を得るために、前記固体の有機マグネシウム前駆体は、加熱を伴うまたは伴わない減圧を用いてか、沈殿、再結晶を経てのどちらかによって、前記溶媒和剤から単離される、請求項1に記載のプロセス。
- 前記沈殿された固体の有機マグネシウム前駆体は、触媒合成用に直接または溶液形態のどちらかで使用される、請求項2に記載のプロセス。
- 前記沈殿された固体は、沈殿された固体の溶液形態を得るために、溶媒中に溶解される、請求項2に記載のプロセス。
- 沈殿された固体を溶解させるために使用される前記溶媒は、極性脂肪族炭化水素、非極性脂肪族炭化水素、極性芳香族炭化水素、非極性芳香族炭化水素、およびこれらの組合わせを含む群から選択される、請求項2に記載のプロセス。
- 前記沈殿の手順は、前駆体合成の任意の段階の間に採用される、請求項2に記載のプロセス。
- 前記マグネシウム源は、金属マグネシウム、ジアルキルマグネシウム、アルキル/アリールマグネシウムハロゲン化物、およびこれらの混合物を含む群から選択され、
(a)前記金属マグネシウムは、粉末、顆粒、リボン、削りくず、ワイヤ、ブロック、塊、または小片の形態であり、
(b)前記ジアルキルマグネシウムは、ジメチルマグネシウム、ジエチルマグネシウム、ジイソプロピルマグネシウム、ジブチルマグネシウム、ジヘキシルマグネシウム、ジオクチルマグネシウム、エチルブチルマグネシウム、およびブチルオクチルマグネシウムを含む群から選択され、
(c)前記アルキル/アリールマグネシウムハロゲン化物は、メチルマグネシウムクロリド、エチルマグネシウムクロリド、イソプロピルマグネシウムクロリド、イソブチルマグネシウムクロリド、tert−ブチルマグネシウムクロリド、ベンジルマグネシウムクロリド、メチルマグネシウムブロミド、エチルマグネシウムブロミド、イソプロピルマグネシウムブロミド、イソブチルマグネシウムブロミド、tert−ブチルマグネシウムブロミド、ヘキシルマグネシウムブロミド、ベンジルマグネシウムブロミド、メチルマグネシウムヨージド、エチルマグネシウムヨージド、イソプロピルマグネシウムヨージド、イソブチルマグネシウムヨージド、tert−ブチルマグネシウムヨージド、およびベンジルマグネシウムヨージドを含む群から選択される、請求項1に記載のプロセス。 - 前記マグネシウム源は金属マグネシウムである、請求項1に記載のプロセス。
- 前記有機ハロゲン化物は、ハロゲン化アルキル、10個から15個の炭素原子を含んだアルキルラジカルを有するハロゲン化されたアルキルベンゼン/ハロゲン化ベンジル、およびこれらの混合物を含む群から選択され、
(a)前記ハロゲン化アルキルは、塩化メチル、塩化エチル、塩化プロピル、塩化イソプロピル、1,1−ジクロロプロパン、1,2−ジクロロプロパン、1,3−ジクロロプロパン、2,3−ジクロロプロパン、塩化ブチル、1,4−ジクロロブタン、塩化tert−ブチル、塩化アミル、塩化tert−アミル、2−クロロペンタン、3−クロロペンタン、1,5−ジクロロペンタン、1−クロロ−8−ヨードオクタン、1−クロロ−6−シアノヘキサン、塩化シクロペンチル、塩化シクロヘキシル、塩素化されたドデカン、塩素化されたテトラデカン、塩素化されたエイコサン、塩素化されたペンタコサン、塩素化されたトリアコンタン、塩化イソオクチル、5−クロロ−5−メチルデカン、9−クロロ−9−エチル−6−メチルエイコサンを含む群から選択され、
(b)前記ハロゲン化されたアルキルベンゼン/ハロゲン化ベンジルは、塩化ベンジルおよびα,α'ジクロロキシレンを含む群から選択される、請求項1に記載のプロセス。 - 前記有機ハロゲン化物は、塩化ベンジルまたは塩化ブチルまたはこれらの混合物である、請求項1に記載のプロセス。
- 前記溶媒和剤は、ジエチルエーテルまたはテトラヒドロフランまたはこれらの混合物である、請求項1に記載のプロセス。
- 前記アルコールは、脂肪族アルコール、脂環式アルコール、芳香族アルコール、アルコキシ基を含んだ脂肪族アルコール、ジオール、およびこれらの混合物を含む群から選択され、
(a)前記脂肪族アルコールは、メタノール、エタノール、プロパノール、ブタノール、イソブタノール、t−ブタノール、n−ペンタノール、イソペンタノール、ヘキサノール、2−メチルペンタノール、2−エチルブタノール、n−ヘプタノール、n−オクタノール、2−エチルヘキサノール、デカノール、およびドデカノールを含む群から選択され、
(b)前記脂環式アルコールは、シクロヘキサノールおよびメチルシクロヘキサノールを含む群から選択され、
(c)前記芳香族アルコールは、ベンジルアルコールおよびメチルベンジルアルコールを含む群から選択され、
(d)前記アルコキシ基を含んだ脂肪族アルコールは、エチルグリコールおよびブチルグリコールを含む群から選択され、
(e)前記ジオールは、カテコール、エチレングリコール、1,3−プロパンジオール、1,4−ブタンジオール、1,5−ペンタンジオール、1,8−オクタンジオール、1,2−プロパンジオール、1,2−ブタンジオール、2,3−ブタンジオール、1,3−ブタンジオール、1,2−ペンタンジオール、p−メンタン−3,8−ジオール、および2−メチル−2,4−ペンタンジオールを含む群から選択される、請求項1に記載のプロセス。 - 前記マグネシウム源は、1:20から1:0.2の間のモル比で、前記有機ハロゲン化物と反応される、請求項1に記載のプロセス。
- 前記マグネシウム源および前記溶媒和剤のモル比は、1:20から1:0.2の間である、請求項1に記載のプロセス。
- 溶媒和剤中でのマグネシウム成分の均一溶液を形成するために、前記マグネシウム源、前記有機ハロゲン化物、および前記溶媒和剤は、−20℃から200℃の間の温度で接触され、接触の時間は、0.5から12時間である、請求項1に記載のプロセス。
- 任意で必要な反応促進剤は、ヨウ素、無機ハロゲン化物、窒素ハロゲン化物、およびこれらの混合物を含む群から選択され、
(a)前記無機ハロゲン化物は、CuCl、MnCl2、およびAgClを含む群から選択され、
(b)前記窒素ハロゲン化物は、N−ハロゲン化スクシンイミド、トリハロイソシアヌル酸、N−ハロフタルイミド、およびヒダントイン化合物を含む群から選択される、請求項1に記載のプロセス。 - 触媒組成物を調製するプロセスであって、
(a)生成溶液を得るために、M(OR''')pX4−pで表される遷移金属化合物の溶液を、請求項1に記載のプロセスにより調製される前記固体の有機マグネシウム前駆体成分と接触させるステップであって、式中、MはTiであり、Xはハロゲン原子であり、R'''は炭化水素基であり、pは4に等しいか4よりも小さい値を有する整数であり、前記固体の有機マグネシウム前駆体と前記遷移金属化合物との接触温度は、−50℃から150℃の間であるステップと、
(b)前記固体の有機マグネシウム前駆体成分または前記遷移金属化合物である成分のどちらかに対して内部電子供与体を添加するステップであって、−50℃から100℃の間の接触温度において、前記内部電子供与体とのどちらかの前記成分の接触の時間は、瞬間的であるかまたは少なくとも1分から60分までであるステップと、
(c)前記ステップ(a)で得られた前記生成溶液を、溶媒中のチタニウム成分を含む溶液で処理し、固体のチタニウム触媒成分を回収し、前記チタニウム触媒成分を、100から120℃の範囲内の温度値に10から60分間維持するステップと、
(d)任意でステップ(c)を予め定められた回数繰り返し、その後、固体の触媒組成物を得るために、20℃から80℃の温度において不活性溶媒によって十分に洗浄が成されるステップと、
を有し、
前記触媒組成物は、2.0wt%から20wt%の内部電子供与体、0.5wt%から10.0wt%のチタニウム、および10wt%から20wt%のマグネシウムである、プロセス。 - ステップ(a)において、前記遷移金属化合物が前記有機マグネシウム前駆体に対して加えられるか、あるいはその逆である、請求項17に記載のプロセス。
- ステップ(b)は、内部電子供与体を伴う有機マグネシウム前駆体を添加するステップを有する、請求項17に記載のプロセス。
- M(OR''')pX4−pで表される前記遷移金属の化合物は、遷移金属四ハロゲン化物、アルコキシ遷移金属三ハロゲン化物/アリールオキシ遷移金属三ハロゲン化物、ジアルコキシ遷移金属二ハロゲン化物、トリアルコキシ遷移金属一ハロゲン化物、テトラアルコキシ遷移金属、およびこれらの混合物を含む群から選択され、
(a)前記遷移金属四ハロゲン化物は、四塩化チタン、四臭化チタン、および四よう化チタンを含む群から選択され、
(b)前記アルコキシ遷移金属三ハロゲン化物/アリールオキシ遷移金属三ハロゲン化物は、三塩化メトキシチタン、三塩化エトキシチタン、三塩化ブトキシチタン、および三塩化フェノキシチタンを含む群から選択され、
(c)前記ジアルコキシ遷移金属二ハロゲン化物は、二塩化ジエトキシチタンであり、
(d)前記トリアルコキシ遷移金属一ハロゲン化物は、塩化トリエトキシチタンであり、
(e)前記テトラアルコキシ遷移金属は、テトラブトキシチタンおよびテトラエトキシチタンを含む群から選択される、請求項17に記載のプロセス。 - 使用される前記内部電子供与体は、フタル酸エステル、安息香酸エステル、コハク酸エステル、マロン酸エステル、炭酸塩、ジエーテル、およびこれらの組合わせを含む群から選択され、
(a)前記フタル酸エステルは、フタル酸ジ−n−ブチル、フタル酸ジイソブチル、フタル酸ジ−2−エチルヘキシル、フタル酸ジ−n−オクチル、フタル酸ジイソオクチル、フタル酸ジ−n−ノニルを含む群から選択され、
(b)前記安息香酸エステルは、安息香酸メチル、安息香酸エチル、安息香酸プロピル、安息香酸フェニル、安息香酸シクロヘキシル、トルイル酸メチル、トルイル酸エチル、p−エトキシ安息香酸エチル、p−イソプロポキシ安息香酸エチルを含む群から選択され、
(c)前記コハク酸エステルは、コハク酸ジエチル、コハク酸ジプロピル、コハク酸ジイソプロピル、コハク酸ジブチル、コハク酸ジイソブチルを含む群から選択され、
(d)前記マロン酸エステルは、マロン酸ジエチル、エチルマロン酸ジエチル、プロピルマロン酸ジエチル、イソプロピルマロン酸ジエチル、ブチルマロン酸ジエチルを含む群から選択され、
(e)前記炭酸塩は、1,2−シクロヘキサンジカルボン酸ジエチル、1,2−シクロヘキサンジカルボン酸ジ−2−エチルヘキシル、1,2−シクロヘキサンジカルボン酸ジ−2−イソノニル、アニス酸メチル、アニス酸エチルを含む群から選択され、
(f)前記ジエーテルは、9,9−ビス(メトキシメチル)フルオレン、2−イソプロピル−2−イソペンチル−1,3−ジメトキシプロパン、2,2−ジイソブチル−1,3−ジメトキシプロパン、2,2−ジイソペンチル−1,3−ジメトキシプロパン、および2−イソプロピル−2−シクロヘキシル−1,3−ジメトキシプロパンを含む群から選択される、請求項17に記載のプロセス。 - ステップ(a)において、有機マグネシウム化合物のチタニウム化合物との前記接触は、ニートであるか溶媒中かのどちらかである、請求項17に記載のプロセス。
- ステップ(a)において、前記固体の有機マグネシウム化合物は、固体としてまたは溶媒中で使用される、請求項17に記載のプロセス。
- 前記溶媒は、塩素化された芳香族炭化水素、塩素化されていない芳香族炭化水素、塩素化された脂肪族炭化水素、塩素化されていない脂肪族炭化水素、およびそれらの組合わせを含む群から選択される、請求項22または請求項23に記載のプロセス。
- 前記溶媒を5から95容量パーセント含み、前記溶媒は、ベンゼン、デカン、ケロシン、エチルベンゼン、クロロベンゼン、ジクロロベンゼン、トルエン、o−クロロトルエン、キシレン、ジクロロメタン、クロロホルム、シクロヘキサン、およびこれらの組合わせを含む群から選択される、請求項22から請求項24のいずれか1項に記載のプロセス。
- ステップ(b)において、前記内部電子供与体は、マグネシウムの1モルに対して、0モルより大きく1モル以下の量で使用される、請求項17に記載のプロセス。
- 触媒系を調製するプロセスであって、前記触媒系を得るために、前記プロセスは、請求項17に記載のプロセスにより得られた触媒組成物を少なくとも1つの共触媒および少なくとも1つの外部電子供与体に接触させるステップを有し、
前記共触媒は、水素化物、有機アルミニウム、リチウム、亜鉛、スズ、カドミウム、ベリリウム、マグネシウム、およびこれらの組合わせを含む群から選択され、
前記外部電子供与体は、有機ケイ素化合物、ジエーテル、アルコキシ安息香酸塩、アミン、エステル、カルボン酸塩、ケトン、アミド、ホスフィン、カルバミン酸塩、リン酸塩、スルホン酸塩、スルホン、スルホキシド、およびこれらの組合わせを含む群から選択される、プロセス。 - 重合条件下において、2個から20個の炭素原子を有するオレフィンを請求項27に記載の前記触媒系と接触させる前記ステップを含む、オレフィンを重合するおよび共重合するうちの少なくとも一方であるプロセス。
- 重合は、希釈剤として不活性炭化水素溶媒を用いたスラリー重合によって、または、反応媒体として液体モノマを用い、1または複数の流動層反応器または機械的に撹拌された床反応器中で気相において動作するバルク重合により実行される、請求項28に記載のプロセス。
- 前記オレフィンは、エチレン、プロピレン、1−ブテン、4−メチル−1−ペンテン、1−ヘキセン、1−オクテン、およびこれらの組合わせを含む群から選択される、請求項28または請求項29に記載のプロセス。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IN2765/MUM/2012 | 2012-09-24 | ||
IN2765MU2012 | 2012-09-24 | ||
PCT/IB2013/058797 WO2014045260A2 (en) | 2012-09-24 | 2013-09-24 | Organometallic compound in solid form, process for preparing the same and use thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2015527359A JP2015527359A (ja) | 2015-09-17 |
JP6026662B2 true JP6026662B2 (ja) | 2016-11-16 |
Family
ID=54188021
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2015528002A Active JP6026662B2 (ja) | 2012-09-24 | 2013-09-24 | 固体形態の有機金属化合物を調製するプロセス、およびその使用により触媒組成物および触媒系を調製するプロセス |
Country Status (8)
Country | Link |
---|---|
US (3) | US9587041B2 (ja) |
EP (2) | EP2897966B1 (ja) |
JP (1) | JP6026662B2 (ja) |
KR (1) | KR101677737B1 (ja) |
CN (1) | CN104583219B (ja) |
RU (1) | RU2615128C2 (ja) |
SA (2) | SA516371258B1 (ja) |
WO (1) | WO2014045260A2 (ja) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014045259A2 (en) * | 2012-09-24 | 2014-03-27 | Indian Oil Corporation Limited | Precursor for catalyst, process for preparing the same and its use thereof |
EP2966099B1 (en) | 2014-07-08 | 2020-03-11 | Indian Oil Corporation Limited | Particle size distribution control through internal donor in ziegler-natta catalyst |
EP3050906B1 (en) | 2015-01-27 | 2020-07-22 | Indian Oil Corporation Limited | Catalyst process modification and polymerization thereof |
ES2700449T3 (es) | 2015-02-23 | 2019-02-15 | Indian Oil Corp Ltd | Procedimiento para preparar un catalizador para la polimerización de olefinas y polimerización |
EP3162819B1 (en) * | 2015-06-26 | 2018-09-05 | Indian Oil Corporation Limited | Improved ziegler-natta catalyst synthesis and process thereof |
US11186653B2 (en) | 2017-03-17 | 2021-11-30 | Sabic Global Technologies B.V. | Process of making polyolefins |
RU2692246C1 (ru) * | 2017-06-15 | 2019-06-24 | Индийская Нефтяная Корпорация Лимитэд | Внешний донор для полимеризации олефинов |
KR102467586B1 (ko) * | 2017-11-17 | 2022-11-15 | 롯데케미칼 주식회사 | 폴리에틸렌 합성용 촉매의 제조방법 및 이를 이용한 폴리에틸렌의 제조방법 |
KR102467604B1 (ko) * | 2017-11-22 | 2022-11-15 | 롯데케미칼 주식회사 | 담체 입자의 제조방법 |
CN109912735B (zh) * | 2017-12-12 | 2020-09-29 | 中国科学院化学研究所 | 烯烃聚合催化剂用外给电子体、催化剂体系以及聚烯烃的制备方法 |
RU2674440C1 (ru) * | 2017-12-20 | 2018-12-10 | Федеральное государственное бюджетное учреждение науки Институт катализа им. Г.К. Борескова Сибирского отделения Российской академии наук (ИК СО РАН) | Способ получения катализатора и способ полимеризации олефинов с его использованием |
CN110327842B (zh) * | 2019-07-15 | 2021-07-13 | 四川轻化工大学 | 一种八氟戊醇基含氟表面活性剂及其制备方法 |
CN112794935B (zh) * | 2019-10-28 | 2023-01-03 | 中国石油化工股份有限公司 | 固体催化剂及其制备方法与应用 |
KR102487347B1 (ko) * | 2020-12-04 | 2023-01-11 | 한화토탈에너지스 주식회사 | 초고분자량 폴리에틸렌의 분자량분포 조절을 위한 지글러-나타 촉매의 제조방법 |
EP4155325A1 (en) | 2021-09-27 | 2023-03-29 | Indian Oil Corporation Limited | A process for preparation of a catalyst for polymerization of olefins |
Family Cites Families (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1603724A (en) | 1977-05-25 | 1981-11-25 | Montedison Spa | Components and catalysts for the polymerisation of alpha-olefins |
IT1098272B (it) * | 1978-08-22 | 1985-09-07 | Montedison Spa | Componenti,di catalizzatori e catalizzatori per la polimerizzazione delle alfa-olefine |
JPS59207904A (ja) * | 1983-05-11 | 1984-11-26 | Mitsui Petrochem Ind Ltd | オレフイン重合体の製造方法 |
DE3501858A1 (de) * | 1985-01-22 | 1986-07-24 | Neste Oy, Espoo | Katalysator-komponenten, katalysator und verfahren fuer die polymerisation von olefinen |
US4792640A (en) | 1986-04-18 | 1988-12-20 | Lithium Corporation Of America | Hydrocarbyloxy magnesium halides |
US4727051A (en) | 1986-12-15 | 1988-02-23 | Stauffer Chemical Company | Production of halide-and alkoxy-containing magnesium compositions |
US4820879A (en) * | 1987-06-05 | 1989-04-11 | Lithium Corporation Of America | Preparation of hydrocarbyloxy magnesium halides |
US4820672A (en) | 1987-06-25 | 1989-04-11 | Lithium Corporation Of America | Hydrocarbon soluble and insoluble organo magnesium chloride complexes, processes and uses |
IT1227259B (it) * | 1988-09-30 | 1991-03-28 | Himont Inc | Catalizzatori per la polimerizzazione di olefine. |
US5108972A (en) | 1989-10-16 | 1992-04-28 | Akzo Nv | Process of making halide/alkoxy-containing magnesium complex |
US5081320A (en) | 1990-03-22 | 1992-01-14 | Akzo Nv | Novel halide/alkoxy-containing magnesium compounds |
DE4108204A1 (de) | 1991-03-14 | 1992-09-17 | Schering Ag | Verfahren zur herstellung von alkoxymagnesiumhalogeniden |
WO1996032426A1 (en) * | 1995-04-10 | 1996-10-17 | Dsm N.V. | Method for the preparation of a catalyst suitable for the polymerisation of an olefine |
JP4467778B2 (ja) * | 1999-12-15 | 2010-05-26 | 出光興産株式会社 | マグネシウム化合物の製造方法、オレフィン重合触媒及びオレフィン重合体の製造方法 |
WO2002030998A1 (en) * | 2000-10-13 | 2002-04-18 | Basell Technology Company B.V. | Catalyst components for the polymerization of olefins |
EP1165633B1 (en) * | 2000-02-02 | 2004-07-14 | Basell Poliolefine Italia S.p.A. | Components and catalysts for the polymerization of olefins |
KR100428885B1 (ko) * | 2001-06-14 | 2004-04-28 | 건 희 서 | 산화마그네슘을 이용한 건자재 성형방법 |
ATE328912T1 (de) | 2001-06-20 | 2006-06-15 | Borealis Tech Oy | Herstellung eines katalysatorbestandteils zur olefinpolymerisation |
EP1403292B1 (en) * | 2002-09-30 | 2016-04-13 | Borealis Polymers Oy | Process for preparing an olefin polymerisation catalyst component with improved high temperature activity |
RU2330863C2 (ru) * | 2003-03-27 | 2008-08-10 | Базелль Полиолефин Италия С.Р.Л. | Аддукты дихлорид магния-спирт и компоненты катализатора, полученные из них |
US7135531B2 (en) | 2004-01-28 | 2006-11-14 | Basf Catalysts Llc | Spherical catalyst for olefin polymerization |
CA2561576A1 (en) * | 2004-03-29 | 2005-10-13 | Basell Poliolefine Italia S.R.L. | Magnesium chloride-based adducts and catalyst components obtained therefrom |
EP2027164B1 (en) | 2006-05-24 | 2012-08-15 | Saudi Basic Industries Corporation | Process for preparing a catalyst component for propylene polymerization |
KR101716507B1 (ko) * | 2007-12-21 | 2017-03-14 | 더블유.알. 그레이스 앤드 캄파니-콘. | 두자리 내부 공여체를 가진 자기-제한성 촉매 조성물 |
EP2283048B1 (en) * | 2008-05-21 | 2016-03-02 | Reliance Industries Limited | A catalyst system for polymerization of olefins |
WO2014045259A2 (en) * | 2012-09-24 | 2014-03-27 | Indian Oil Corporation Limited | Precursor for catalyst, process for preparing the same and its use thereof |
-
2013
- 2013-09-24 WO PCT/IB2013/058797 patent/WO2014045260A2/en active Application Filing
- 2013-09-24 RU RU2015105286A patent/RU2615128C2/ru active
- 2013-09-24 EP EP13802109.2A patent/EP2897966B1/en active Active
- 2013-09-24 JP JP2015528002A patent/JP6026662B2/ja active Active
- 2013-09-24 KR KR1020157004532A patent/KR101677737B1/ko active IP Right Grant
- 2013-09-24 CN CN201380043620.7A patent/CN104583219B/zh active Active
- 2013-09-24 EP EP19212958.3A patent/EP3653631A1/en not_active Ceased
- 2013-09-24 US US14/416,609 patent/US9587041B2/en active Active
-
2015
- 2015-03-08 SA SA516371258A patent/SA516371258B1/ar unknown
- 2015-03-08 SA SA515360122A patent/SA515360122B1/ar unknown
-
2016
- 2016-12-06 US US15/371,193 patent/US10100136B2/en active Active
-
2018
- 2018-08-20 US US16/105,580 patent/US10611865B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
SA516371258B1 (ar) | 2019-04-01 |
WO2014045260A3 (en) | 2014-07-03 |
US9587041B2 (en) | 2017-03-07 |
CN104583219B (zh) | 2018-03-16 |
JP2015527359A (ja) | 2015-09-17 |
KR101677737B1 (ko) | 2016-11-18 |
CN104583219A (zh) | 2015-04-29 |
SA515360122B1 (ar) | 2016-08-21 |
WO2014045260A2 (en) | 2014-03-27 |
US10100136B2 (en) | 2018-10-16 |
US20170081440A1 (en) | 2017-03-23 |
US10611865B2 (en) | 2020-04-07 |
US20150191553A1 (en) | 2015-07-09 |
US20180355082A1 (en) | 2018-12-13 |
RU2015105286A (ru) | 2016-09-10 |
EP2897966A2 (en) | 2015-07-29 |
KR20150038224A (ko) | 2015-04-08 |
EP2897966B1 (en) | 2020-04-01 |
RU2615128C2 (ru) | 2017-04-04 |
EP3653631A1 (en) | 2020-05-20 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6026662B2 (ja) | 固体形態の有機金属化合物を調製するプロセス、およびその使用により触媒組成物および触媒系を調製するプロセス | |
JP6026661B2 (ja) | 触媒用前駆体を調製するプロセス、触媒組成物を調製するプロセス、触媒系を調製するプロセス、及び、オレフィンを重合するおよび共重合するうちの少なくとも一方である方法 | |
EP2872538B1 (en) | Ziegler-natta catalyst systems comprising a 1,2-phenylenedioate as internal donor and process for preparing the same | |
US9644050B2 (en) | Particle size distribution control through internal donor in Ziegler-Natta catalyst | |
JP5984173B2 (ja) | オレフィン重合用の触媒を調製するプロセス | |
EP3018150B1 (en) | Process for the preparation of spherical catalyst particles | |
US9896523B2 (en) | Ziegler-Natta catalyst synthesis and process thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20160112 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20160412 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20160809 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20160819 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20160913 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20161012 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6026662 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |