JPH05505593A - モノシクロペンタジエニル遷移金属オレフィン重合触媒 - Google Patents
モノシクロペンタジエニル遷移金属オレフィン重合触媒Info
- Publication number
- JPH05505593A JPH05505593A JP90513762A JP51376290A JPH05505593A JP H05505593 A JPH05505593 A JP H05505593A JP 90513762 A JP90513762 A JP 90513762A JP 51376290 A JP51376290 A JP 51376290A JP H05505593 A JPH05505593 A JP H05505593A
- Authority
- JP
- Japan
- Prior art keywords
- group
- hydrocarbyl
- groups
- reactor
- substituted
- 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
- -1 transition metal olefin Chemical class 0.000 title claims description 84
- 229910052723 transition metal Inorganic materials 0.000 title claims description 35
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title description 6
- 239000002685 polymerization catalyst Substances 0.000 title description 2
- 239000003054 catalyst Substances 0.000 claims description 106
- 150000001875 compounds Chemical class 0.000 claims description 87
- 238000000034 method Methods 0.000 claims description 47
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
- 239000003446 ligand Substances 0.000 claims description 35
- 150000003624 transition metals Chemical group 0.000 claims description 35
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 29
- 125000005843 halogen group Chemical group 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 150000007527 lewis bases Chemical group 0.000 claims description 21
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical group C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 18
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 239000010936 titanium Substances 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 230000000737 periodic effect Effects 0.000 claims description 16
- 229910052719 titanium Inorganic materials 0.000 claims description 16
- 239000002841 Lewis acid Chemical group 0.000 claims description 15
- 125000003368 amide group Chemical group 0.000 claims description 15
- 150000007517 lewis acids Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 230000003197 catalytic effect Effects 0.000 claims description 10
- 229910052735 hafnium Inorganic materials 0.000 claims description 10
- 229910052726 zirconium Inorganic materials 0.000 claims description 10
- 150000002738 metalloids Chemical class 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 8
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 7
- 239000002879 Lewis base Substances 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 6
- 125000000129 anionic group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 238000004132 cross linking Methods 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical group [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052752 metalloid Inorganic materials 0.000 claims description 6
- 230000007935 neutral effect Effects 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 150000004703 alkoxides Chemical class 0.000 claims description 5
- 125000001118 alkylidene group Chemical group 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 5
- PDPJQWYGJJBYLF-UHFFFAOYSA-J hafnium tetrachloride Chemical compound Cl[Hf](Cl)(Cl)Cl PDPJQWYGJJBYLF-UHFFFAOYSA-J 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000013522 chelant Substances 0.000 claims description 4
- 150000004678 hydrides Chemical group 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 125000003367 polycyclic group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 claims description 2
- 125000006659 (C1-C20) hydrocarbyl group Chemical group 0.000 claims 18
- 150000001768 cations Chemical class 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims 1
- 229910001507 metal halide Inorganic materials 0.000 claims 1
- 150000005309 metal halides Chemical class 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 450
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 188
- 239000000243 solution Substances 0.000 description 129
- 239000000203 mixture Substances 0.000 description 113
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 110
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 110
- 239000005977 Ethylene Substances 0.000 description 110
- 239000002904 solvent Substances 0.000 description 97
- 238000006116 polymerization reaction Methods 0.000 description 75
- 238000006243 chemical reaction Methods 0.000 description 66
- 239000007787 solid Substances 0.000 description 61
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 54
- 239000000047 product Substances 0.000 description 52
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 49
- 229920001577 copolymer Polymers 0.000 description 43
- 239000003208 petroleum Substances 0.000 description 40
- 229920000642 polymer Polymers 0.000 description 40
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 238000013461 design Methods 0.000 description 33
- 238000002474 experimental method Methods 0.000 description 31
- 239000000706 filtrate Substances 0.000 description 30
- 229920000573 polyethylene Polymers 0.000 description 30
- 239000004698 Polyethylene Substances 0.000 description 29
- 239000007788 liquid Substances 0.000 description 29
- 238000001704 evaporation Methods 0.000 description 28
- 229940126062 Compound A Drugs 0.000 description 27
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 27
- 230000008020 evaporation Effects 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 239000004711 α-olefin Substances 0.000 description 27
- 238000009826 distribution Methods 0.000 description 25
- 241000894007 species Species 0.000 description 25
- 150000003623 transition metal compounds Chemical class 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000000460 chlorine Substances 0.000 description 19
- 238000004519 manufacturing process Methods 0.000 description 17
- 238000002156 mixing Methods 0.000 description 17
- 239000003085 diluting agent Substances 0.000 description 14
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 12
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 12
- 239000000178 monomer Substances 0.000 description 12
- 229910013470 LiC1 Inorganic materials 0.000 description 10
- 229920000098 polyolefin Polymers 0.000 description 10
- 238000001556 precipitation Methods 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 241000349731 Afzelia bipindensis Species 0.000 description 9
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- AQZWEFBJYQSQEH-UHFFFAOYSA-N 2-methyloxaluminane Chemical group C[Al]1CCCCO1 AQZWEFBJYQSQEH-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 8
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 150000001336 alkenes Chemical class 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical group 0.000 description 7
- 239000007791 liquid phase Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 7
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical group OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
- 239000000470 constituent Substances 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 4
- 229910003865 HfCl4 Inorganic materials 0.000 description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000010348 incorporation Methods 0.000 description 4
- 229910003002 lithium salt Inorganic materials 0.000 description 4
- 159000000002 lithium salts Chemical class 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- 239000011550 stock solution Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 229910003074 TiCl4 Inorganic materials 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000004575 stone Substances 0.000 description 3
- 239000012085 test solution Substances 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 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
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 description 2
- 229910015427 Mo2O3 Inorganic materials 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 240000007817 Olea europaea Species 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 229910007928 ZrCl2 Inorganic materials 0.000 description 2
- 239000012615 aggregate Substances 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
- 150000001923 cyclic compounds Chemical class 0.000 description 2
- PESYEWKSBIWTAK-UHFFFAOYSA-N cyclopenta-1,3-diene;titanium(2+) Chemical compound [Ti+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 PESYEWKSBIWTAK-UHFFFAOYSA-N 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- 239000012968 metallocene catalyst Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- PRBHEGAFLDMLAL-XQRVVYSFSA-N (4z)-hexa-1,4-diene Chemical compound C\C=C/CC=C PRBHEGAFLDMLAL-XQRVVYSFSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- COOXAWDWHWRVRD-UHFFFAOYSA-N C[Ti]C Chemical compound C[Ti]C COOXAWDWHWRVRD-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
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- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical class [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
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- 125000000913 palmityl 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])C([H])([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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- AJBKMHRPHLTCRS-UHFFFAOYSA-L phenylazanide titanium(3+) dichloride Chemical compound [Cl-].[Cl-].[Ti++]Nc1ccccc1 AJBKMHRPHLTCRS-UHFFFAOYSA-L 0.000 description 1
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- 230000035484 reaction time Effects 0.000 description 1
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- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-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
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 1
Classifications
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- 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
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65916—Component covered by group C08F4/64 containing a transition metal-carbon bond supported on a carrier, e.g. silica, MgCl2, polymer
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- C08F4/00—Polymerisation catalysts
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- 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
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- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/6592—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Abstract
Description
Claims (1)
- 【特許請求の範囲】 1 一般式: ▲数式、化学式、表等があります▼ 又は ▲数式、化学式、表等があります▼ (式中、Mは最大のホルマール酸化状態のZr、Hf又はTiであり、 (C5H4−xRx)は、0乃至4の置換基Rで置換されたシクロペンタジエニ ル環、xは置換の程度を意味する0、1、2、3又は4であり、各置換基Rは独 立して、C1−C20ヒドロカルビル基、1つ以上の水素原子がハロゲン基、ア ミド基、ホスファイド基及びアルコキシ基又は、ルイス酸又は塩基官能価を含む その他の基で置換された置換C1−C20ヒドロカルビル基、メタロイドが元素 周期表WA族から選ばれるC1−C20ヒドロカルビル置換メタロイド基、ハロ ゲン基、アミド基、ホスファイド基、アルコキシ基、アルキルボーライド(al kylborido)基又は、ルイス酸又は塩基官能価を有するその他の基から 成る群から選ばれる基、又は(C5H4−xRx)は、2つの隣接したR基が結 合してC4−C20環を形成し、インデニル、テトラヒドロインデニル、フルオ レニル又はオクタヒドロフルオレニルのような飽和又は不飽和の多環式シクロペ ンタジエニル配位子を与えるシクロペンタジエニル環であり、 (JR′z−2)は、Jが3つの配位数を有する元素周期表のVA族の元素又は 、2つの配位数を有する元素周期表のWA族の元素であり、各R′は独立して、 C1−C20ヒドロカルビル基、1つ以上の水素原子がハロゲン基、アミド基、 ホスファイド基及びアルコキシ基又は、ルイス酸又は塩基官能価を含むその他の 基で置換された置換C1−C20ヒドロカルビル基から成る群から選ばれる基で あり、zは元素Jの配位数である、ヘテロ原子配位子であり、 各Qは独立して、ハライド、ハイドライド又は置換された又は非置換のC1−C 20ヒドロカルビル、アルコキシド、アリールオキシド、アミド、アリールアミ ド、ホスファイド又はアリールホスファイドのような1価のアニオン配位子であ り、いずれかのQがヒドロカルビルであるときはそのQは(C5H4−xRx) と異なり、又は両方のQが一緒でアルキリデン又は環状金属化(cyclome tailated)ヒドロカルビル又はその他の2価のアニオンキレート配位子 であり、 Tは、rIVA族又はVA族の元素を含有する共有結合の架橋基であり、 Lはwが1乃至3の数である中性ルイス塩基である) を有する化合物。 2 ヘテロ原子配位子基J元素が、窒素、燐、酵素又は硫黄である、請求項1に 記載の化合物。 3 Qがハライド又はヒドロカルビル基である、請求項1に記載の化合物。 4 ヘテロ原子配位子基J元素が窒素である、請求項2に記載の化合物。 5 Mがハフニウム、ジルコニウム又はチタンである、請求項1に記載の化合物 。 6 (A)式: ▲数式、化学式、表等があります▼ 又は ▲数式、化学式、表等があります▼ (式中、Mは、その最大のホルマール酸化状態のTiであり、 (C2H5−y−xRx)は、0乃至5の置換基Rで置換されたシクロペンタジ エニル環、xは置換の程度を意味する0、1、2、3、4又は5であり、各置換 基Rは独立して、C1−C20ヒドロカルビル基、1つ以上の水素原子がハロゲ ン基、アミド基、ホスファイド基及びアルコキシ基又は、ルイス酸又は塩基官能 価を含むその他の基で置換された置換C1−C20ヒドロカルビル基、メタロイ ドが元素周期表IVA族から選ばれるC1−C20ヒドロカルビル置換メタロイ ド基、ハロゲン基、アミド基、ホスファイド基、アルコキシ基、アルキルボーラ イド(alkylborido)基又は、ルイス酸又は塩基官能価を有するその 他の基から成る群から選ばれる基であるか、又は(C2H5−y−xRx)は、 2つの隣接したR基が結合してC4−C20環を形成し、インデニル、テトラヒ ドロインデニル、フルオレニル又はオクタヒドロフルオレニルのような飽和又は 不飽和の多環式シクロペンタジエニル配位子を与えるシクロペンタジエニル環で あり、 (JR′z−1−y)は、Jが3つの配位数を有する元素周期表のVA族の元素 又は2つの配位数を有するVIA族の元素、各R′は独立して、C1−C20ヒ ドロカルビル基、1つ以上の水素原子がハロゲン基、アミド基、ホスファイド基 、アルコキシ基又は、ルイス酸又は塩基官能価を含むその他の基で置換された置 換C1−C20ヒドロカルビル基から成る群から選ばれる基であり、zは元素J の配位数であり、 各Qは独立して、ハライド、ハイドライド又は、置換された又は非置換のC1− C20ヒドロカルビル、アルコキシド、アリールオキシド、アミド、アリールア ミド、ホスファイド又はアリールホスファイドのような1価のアニオン配位子で あり、いずれかのQがヒドロカルビルであるときそのQは(C2H5−y−xR x)と異なり、又は両方のQが一緒でアルキリデン又は環状金属化ヒドロカルビ ル又はその他の2価のアニオンキレート配位子であり、wが0より大きいときは yは0又は1、wが0のときはyは1であり、yは1のときTはIVA族又はV A族の元素を含有する共有結合の架橋基であり、Lはwが0乃至3の数である中 性ルイス塩基である)を有するIVB族遷移金属成分及び(B)アルモキサン を含む触媒系。 7 ヘテロ原子配位子基J元素が窒素、燐、酸素又は硫黄である、請求項6に記 載の触媒系。 8 Qがハライド又はヒドロカルビル基である、請求項6に記載の触媒系。 9 ヘテロ原子配位子基J元素が窒素である、請求項7に記載の触媒系。 10 Mがチタンである、請求項6に記載の触媒系。 11 アルミニウム原子対遷移金属原子のモル比が10:1乃至20,000: 1である、請求項6に記載の触媒系。 12 一般式: ▲数式、化学式、表等があります▼ 又は ▲数式、化学式、表等があります▼ (式中、Mは最大のホルマール酸化状態のZr、Hf又はTiであり、 (C5H4−xRx)は、0乃至4の置換基Rで置換されたシクロペンタジエニ ル環、xは置換の程度を意味する0、1、2、3又は4であり、各置換基Rは独 立して、C1−C20ヒドロカルビル基、1つ以上の水素原子がハロゲン基、ア ミド基、ホスファイド基、アルコキシ基又は、ルイス酸又は塩基官能価を含むそ の他の基で置換された置換C1−C20ヒドロカルビル基、メタロイドが元素周 期表IVA族から選ばれるC1−C20ヒドロカルビル置換メタロイド基、ハロ ゲン基、アミド基、ホスファイド基、アルコキシ基、アルキルボーライド(al kylborido)基又は、ルイス酸又は塩基官能価を有するその他の基から 成る群から選ばれる基、又は(C5H4−xRx)は、2つの隣接したR基が結 合してC4−C20環を形成し、インデニル、テトラヒドロインデニル、フルオ レニル又はオクタヒドロフルオレニルのような飽和又は不飽和の多環式シクロペ ンタジエニル配位子を与えるシクロペンタジエニル環であり、 (JR′z−2)は、Jが3つの配位数を有する元素周期表のVA族の元素又は 2つの配位数を有するVIA族の元素であり、各R′は独立して、C1−C20 ヒドロカルビル基、1つ以上の水素原子がハロゲン基、アミド基、ホスファイド 基及びアルコキシ基又は、ルイス酸又は塩基官能価を含むその他の基で置換され た置換C1−C20ヒドロカルビル基から成る群から選ばれる基であり、zは元 素Jの配位数である、ヘテロ原子配位子であり、各Qは独立して、ハライド、ハ イドライド又は置換された又は非置換のC1−C20ヒドロカルビル、アルコキ シド、アリールオキサイド、アミド、アリールアミド、ホスファイド又はアリー ルホスファイドのような1価のアニオン配位子であり、Qがヒドロカルビルであ るときはそのQは(C5H4−xRx)と異なり、又は両方のQが一緒でアルキ リデン又は環状金属化ヒドロカルビル又はその他の2価のアニオンキレート配位 子であり、 Tは、IVA族又はVA族の元素を含有する共有結合の架橋基であり、 Lはwが1乃至3の数である中性ルイス塩基である)で表わされる化合物を製造 する方法であって、d0IVB族遷移金属ハライドを式: [(C5H4−xRx)−T−(JR′Z−2)]−2のアニオン及び、元素周 期表IA族の2つのカチオン又は元素周期表IIA族の1つのカチオンとを含む 塩と反応させることから成る方法。 13 カチオンがリチウムである、請求項12に記載の方法。 14 IVB族金属ハライドが塩化ハフニウム(IV)、塩化ジルコニウム(I V)又は塩化チタン(IV)又は、塩化チタン(IV)ジエーテル化合物のよう な類似化合物である、請求項12に記載の方法。
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US40694589A | 1989-09-13 | 1989-09-13 | |
US406,945 | 1989-09-13 | ||
US533,245 | 1990-06-04 | ||
US07/533,245 US5055438A (en) | 1989-09-13 | 1990-06-04 | Olefin polymerization catalysts |
PCT/US1990/005208 WO1991004257A1 (en) | 1989-09-13 | 1990-09-13 | Monocyclopentadienyl transition metal olefin polymerization catalysts |
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JP2243683A Pending JPH03188092A (ja) | 1989-09-13 | 1990-09-13 | オレフィン重合触媒 |
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- 1990-09-10 DE DE0420436T patent/DE420436T1/de active Pending
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WO1994029356A1 (fr) * | 1993-06-15 | 1994-12-22 | Idemitsu Kosan Co., Ltd. | Procede de production de polymere olefinique, et catalyseur pour la polymerisation d'une olefine |
US6462154B1 (en) | 1993-06-15 | 2002-10-08 | Idemitsu Kosan Co., Ltd. | Process for preparing olefin polymer and catalyst for polymerization of olefin |
US5965758A (en) * | 1997-06-19 | 1999-10-12 | Sumitomo Chemical Company, Limited | Method for producing bridged type transition metal complex |
US6136995A (en) * | 1997-11-07 | 2000-10-24 | Sumitomo Chemical Company, Limited | Process for producing aminosilane compounds |
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