JP2006525264A - ハロゲン化メタロセン化合物の製造方法 - Google Patents
ハロゲン化メタロセン化合物の製造方法 Download PDFInfo
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- JP2006525264A JP2006525264A JP2006505316A JP2006505316A JP2006525264A JP 2006525264 A JP2006525264 A JP 2006525264A JP 2006505316 A JP2006505316 A JP 2006505316A JP 2006505316 A JP2006505316 A JP 2006505316A JP 2006525264 A JP2006525264 A JP 2006525264A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 63
- 238000004519 manufacturing process Methods 0.000 title abstract description 9
- 239000000460 chlorine Substances 0.000 claims abstract description 25
- 229910052751 metal Inorganic materials 0.000 claims abstract description 19
- 239000002184 metal Substances 0.000 claims abstract description 19
- 230000000737 periodic effect Effects 0.000 claims abstract description 17
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 14
- 230000002140 halogenating effect Effects 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 230000003647 oxidation Effects 0.000 claims abstract description 9
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 7
- 239000011630 iodine Substances 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 31
- 239000003446 ligand Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 9
- 229910052732 germanium Inorganic materials 0.000 claims description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229910052710 silicon Inorganic materials 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 239000002002 slurry Substances 0.000 claims description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000010936 titanium Chemical group 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- 229910052726 zirconium Inorganic materials 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052802 copper Chemical group 0.000 claims description 2
- 239000010949 copper Chemical group 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- 229910052735 hafnium Chemical group 0.000 claims description 2
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical group [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 2
- 230000026030 halogenation Effects 0.000 claims description 2
- 238000005658 halogenation reaction Methods 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Chemical group 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- -1 ethylene-bis (1-indenyl) zirconium dichloride Chemical compound 0.000 description 59
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 52
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 23
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 21
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000011521 glass Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- PWYVVBKROXXHEB-UHFFFAOYSA-M trimethyl-[3-(1-methyl-2,3,4,5-tetraphenylsilol-1-yl)propyl]azanium;iodide Chemical compound [I-].C[N+](C)(C)CCC[Si]1(C)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PWYVVBKROXXHEB-UHFFFAOYSA-M 0.000 description 8
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 7
- UGVVIPAIDGTTNN-UHFFFAOYSA-N C[Zr]C Chemical compound C[Zr]C UGVVIPAIDGTTNN-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 229910007926 ZrCl Inorganic materials 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 241000349731 Afzelia bipindensis Species 0.000 description 5
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 4
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 4
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000000010 aprotic solvent Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical compound C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000002168 alkylating agent Substances 0.000 description 3
- 229940100198 alkylating agent Drugs 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 description 3
- QPFMBZIOSGYJDE-QDNHWIQGSA-N 1,1,2,2-tetrachlorethane-d2 Chemical compound [2H]C(Cl)(Cl)C([2H])(Cl)Cl QPFMBZIOSGYJDE-QDNHWIQGSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- QINWTRVONXWXKE-UHFFFAOYSA-L [Cl-].[Cl-].C[SiH](C)[Ti+2] Chemical compound [Cl-].[Cl-].C[SiH](C)[Ti+2] QINWTRVONXWXKE-UHFFFAOYSA-L 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 229910052796 boron Inorganic materials 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
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 150000001923 cyclic compounds Chemical class 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- IVTQDRJBWSBJQM-UHFFFAOYSA-L dichlorozirconium;indene Chemical compound C1=CC2=CC=CC=C2C1[Zr](Cl)(Cl)C1C2=CC=CC=C2C=C1 IVTQDRJBWSBJQM-UHFFFAOYSA-L 0.000 description 2
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 2
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 2
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 1
- WAADRLKGQPOVGL-UHFFFAOYSA-N 1-[1-(1h-inden-1-yl)ethyl]-1h-indene Chemical compound C1=CC2=CC=CC=C2C1C(C)C1C2=CC=CC=C2C=C1 WAADRLKGQPOVGL-UHFFFAOYSA-N 0.000 description 1
- RGNHLFZGJBKNHR-UHFFFAOYSA-N 7-methyloct-2-ene Chemical compound CC=CCCCC(C)C RGNHLFZGJBKNHR-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- VCFVRHAQERGNFA-UHFFFAOYSA-L C1=CC2=CC=CC=C2C1[Zr](Cl)(Cl)(=[Si](C)C)C1C2=CC=CC=C2C=C1 Chemical compound C1=CC2=CC=CC=C2C1[Zr](Cl)(Cl)(=[Si](C)C)C1C2=CC=CC=C2C=C1 VCFVRHAQERGNFA-UHFFFAOYSA-L 0.000 description 1
- ZHPQWTBKIUMSSW-UHFFFAOYSA-L CC(C)(C)C1(C=CC=C1)[Zr](Cl)(Cl)C1C2=CC=CC=C2C2=C1C=CC=C2 Chemical compound CC(C)(C)C1(C=CC=C1)[Zr](Cl)(Cl)C1C2=CC=CC=C2C2=C1C=CC=C2 ZHPQWTBKIUMSSW-UHFFFAOYSA-L 0.000 description 1
- GQIHHZDGFJJOKJ-UHFFFAOYSA-L CC(C)c1cc2C(C(C)=Cc2c(c1)C(C)C)[Zr](Cl)(Cl)(C1C(C)=Cc2c1cc(cc2C(C)C)C(C)C)=[Si](C)c1ccccc1 Chemical compound CC(C)c1cc2C(C(C)=Cc2c(c1)C(C)C)[Zr](Cl)(Cl)(C1C(C)=Cc2c1cc(cc2C(C)C)C(C)C)=[Si](C)c1ccccc1 GQIHHZDGFJJOKJ-UHFFFAOYSA-L 0.000 description 1
- VWTVXOSCPQSDLG-UHFFFAOYSA-L CC(C)c1cccc2C(C(C)=Cc12)[Zr](Cl)(Cl)(C1C(C)=Cc2c1cccc2C(C)C)=[Si](C)c1ccccc1 Chemical compound CC(C)c1cccc2C(C(C)=Cc12)[Zr](Cl)(Cl)(C1C(C)=Cc2c1cccc2C(C)C)=[Si](C)c1ccccc1 VWTVXOSCPQSDLG-UHFFFAOYSA-L 0.000 description 1
- FLFNHHSXSLXYQB-UHFFFAOYSA-L CC1=CC(C(=CC=C2)C=3C=CC=CC=3)=C2C1[Zr](Cl)(Cl)(=[Si](C)C)C1C(C)=CC2=C1C=CC=C2C1=CC=CC=C1 Chemical compound CC1=CC(C(=CC=C2)C=3C=CC=CC=3)=C2C1[Zr](Cl)(Cl)(=[Si](C)C)C1C(C)=CC2=C1C=CC=C2C1=CC=CC=C1 FLFNHHSXSLXYQB-UHFFFAOYSA-L 0.000 description 1
- OXLXAPYJCPFBFT-UHFFFAOYSA-L CC1=CC(C)(C=C1)[Zr](Cl)(Cl)C1(C)C=CC(C)=C1 Chemical compound CC1=CC(C)(C=C1)[Zr](Cl)(Cl)C1(C)C=CC(C)=C1 OXLXAPYJCPFBFT-UHFFFAOYSA-L 0.000 description 1
- JVSWSVRMIZJVGL-UHFFFAOYSA-L CC1=CC(C=C1)[Zr](Cl)(Cl)(C1c2ccccc2-c2ccccc12)=[Si](C)C Chemical compound CC1=CC(C=C1)[Zr](Cl)(Cl)(C1c2ccccc2-c2ccccc12)=[Si](C)C JVSWSVRMIZJVGL-UHFFFAOYSA-L 0.000 description 1
- UCEHIGDTIYELOU-UHFFFAOYSA-L CC1=CC(C=C1)[Zr](Cl)(Cl)C1C2=CC=CC=C2C2=C1C=CC=C2 Chemical compound CC1=CC(C=C1)[Zr](Cl)(Cl)C1C2=CC=CC=C2C2=C1C=CC=C2 UCEHIGDTIYELOU-UHFFFAOYSA-L 0.000 description 1
- GASYKBUWZJBPAN-UHFFFAOYSA-N C[SiH2]C.CC1=Cc2ccccc2C1.CC1=Cc2ccccc2C1 Chemical compound C[SiH2]C.CC1=Cc2ccccc2C1.CC1=Cc2ccccc2C1 GASYKBUWZJBPAN-UHFFFAOYSA-N 0.000 description 1
- QFKNJQCLGWXWQF-UHFFFAOYSA-L C[Si](C)=[Zr](Cl)(Cl)(C1c2ccccc2-c2ccccc12)C1(C=CC=C1)C(C)(C)C Chemical compound C[Si](C)=[Zr](Cl)(Cl)(C1c2ccccc2-c2ccccc12)C1(C=CC=C1)C(C)(C)C QFKNJQCLGWXWQF-UHFFFAOYSA-L 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 208000034809 Product contamination Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
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- WJGBYUIGLYVGQL-UHFFFAOYSA-L [Cl-].[Cl-].C12=CC=CC=C2N(CC)C2=C1CC([Ti+2])C2 Chemical compound [Cl-].[Cl-].C12=CC=CC=C2N(CC)C2=C1CC([Ti+2])C2 WJGBYUIGLYVGQL-UHFFFAOYSA-L 0.000 description 1
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- KBOAIUOMHXNSGH-UHFFFAOYSA-L [Cl-].[Cl-].CC(C)c1cccc2[C@H](C(C)=Cc12)[Zr++]([C@@H]1C(C)=Cc2c1cccc2C(C)C)=[Si](C)C Chemical compound [Cl-].[Cl-].CC(C)c1cccc2[C@H](C(C)=Cc12)[Zr++]([C@@H]1C(C)=Cc2c1cccc2C(C)C)=[Si](C)C KBOAIUOMHXNSGH-UHFFFAOYSA-L 0.000 description 1
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- PNRJUCXJBYLCRR-UHFFFAOYSA-L [Cl-].[Cl-].CC1=Cc2cccc(C)c2C1[Zr++](C1C(C)=Cc2cccc(C)c12)=[Si](C)C Chemical compound [Cl-].[Cl-].CC1=Cc2cccc(C)c2C1[Zr++](C1C(C)=Cc2cccc(C)c12)=[Si](C)C PNRJUCXJBYLCRR-UHFFFAOYSA-L 0.000 description 1
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- MHNCNVODAWZQFP-UHFFFAOYSA-L [Cl-].[Cl-].CC=1C=CC=2C3=C(N(C=2C=1)C1=CC=CC=C1)CC(C3)[Ti+2] Chemical compound [Cl-].[Cl-].CC=1C=CC=2C3=C(N(C=2C=1)C1=CC=CC=C1)CC(C3)[Ti+2] MHNCNVODAWZQFP-UHFFFAOYSA-L 0.000 description 1
- RQRUFYUHVVRCIK-UHFFFAOYSA-L [Cl-].[Cl-].CN1C2=C(C=3C=CC=CC1=3)CC(C2)[Ti+2] Chemical compound [Cl-].[Cl-].CN1C2=C(C=3C=CC=CC1=3)CC(C2)[Ti+2] RQRUFYUHVVRCIK-UHFFFAOYSA-L 0.000 description 1
- UUIUJCXTMQKYOC-UHFFFAOYSA-L [Cl-].[Cl-].CN1C2=CC(C)=CC=C2C2=C1CC([Ti+2])C2 Chemical compound [Cl-].[Cl-].CN1C2=CC(C)=CC=C2C2=C1CC([Ti+2])C2 UUIUJCXTMQKYOC-UHFFFAOYSA-L 0.000 description 1
- DQRKVKZCSFYRFF-UHFFFAOYSA-L [Cl-].[Cl-].COC=1C=CC=2C3=C(N(C=2C=1)C)CC(C3)[Ti+2] Chemical compound [Cl-].[Cl-].COC=1C=CC=2C3=C(N(C=2C=1)C)CC(C3)[Ti+2] DQRKVKZCSFYRFF-UHFFFAOYSA-L 0.000 description 1
- ODMDDPWFRJKCAL-UHFFFAOYSA-L [Cl-].[Cl-].COC=1C=CC=2C3=C(N(C=2C=1)C1=CC=CC=C1)CC(C3)[Ti+2] Chemical compound [Cl-].[Cl-].COC=1C=CC=2C3=C(N(C=2C=1)C1=CC=CC=C1)CC(C3)[Ti+2] ODMDDPWFRJKCAL-UHFFFAOYSA-L 0.000 description 1
- CYZWONHMLZJHMM-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Zr+2](C1C(=C(C2=CC=CC=C12)C1=CC=C(C=C1)C(C)(C)C)C(C)C)C1C(=C(C2=CC=CC=C12)C1=CC=C(C=C1)C(C)(C)C)C)C Chemical compound [Cl-].[Cl-].C[Si](=[Zr+2](C1C(=C(C2=CC=CC=C12)C1=CC=C(C=C1)C(C)(C)C)C(C)C)C1C(=C(C2=CC=CC=C12)C1=CC=C(C=C1)C(C)(C)C)C)C CYZWONHMLZJHMM-UHFFFAOYSA-L 0.000 description 1
- ALMWVHTWOAEXRV-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Zr+2](C1C(=C(C2=CC=CC=C12)C1=CC=C(C=C1)C(C)(C)C)C)C1C(=C(C2=CC=CC=C12)C1=CC=C(C=C1)C(C)(C)C)C)C Chemical compound [Cl-].[Cl-].C[Si](=[Zr+2](C1C(=C(C2=CC=CC=C12)C1=CC=C(C=C1)C(C)(C)C)C)C1C(=C(C2=CC=CC=C12)C1=CC=C(C=C1)C(C)(C)C)C)C ALMWVHTWOAEXRV-UHFFFAOYSA-L 0.000 description 1
- HFPDVMYYRBTBCE-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Zr+2](C1C2=CC=CC=C2C=2C=CC=CC1=2)C1C=C(C=C1)C(C)C)C Chemical compound [Cl-].[Cl-].C[Si](=[Zr+2](C1C2=CC=CC=C2C=2C=CC=CC1=2)C1C=C(C=C1)C(C)C)C HFPDVMYYRBTBCE-UHFFFAOYSA-L 0.000 description 1
- PRWXJVOJCUXJHK-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Zr+2](C1C2=CC=CC=C2C=2C=CC=CC1=2)C1C=C(C=C1)CC)C Chemical compound [Cl-].[Cl-].C[Si](=[Zr+2](C1C2=CC=CC=C2C=2C=CC=CC1=2)C1C=C(C=C1)CC)C PRWXJVOJCUXJHK-UHFFFAOYSA-L 0.000 description 1
- GFLNNNBAGJKAFE-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](C)=[Zr++](C1C=Cc2c1cccc2-c1cccc2ccccc12)C1C=Cc2c1cccc2-c1cccc2ccccc12 Chemical compound [Cl-].[Cl-].C[Si](C)=[Zr++](C1C=Cc2c1cccc2-c1cccc2ccccc12)C1C=Cc2c1cccc2-c1cccc2ccccc12 GFLNNNBAGJKAFE-UHFFFAOYSA-L 0.000 description 1
- KUNZSLJMPCDOGI-UHFFFAOYSA-L [Cl-].[Cl-].[Hf+2] Chemical compound [Cl-].[Cl-].[Hf+2] KUNZSLJMPCDOGI-UHFFFAOYSA-L 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- HIGRAKVNKLCVCA-UHFFFAOYSA-N alumine Chemical compound C1=CC=[Al]C=C1 HIGRAKVNKLCVCA-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- YEDVUDDWJVRKIS-UHFFFAOYSA-N cyclopenta[b]pyrrole Chemical compound C1=C[C]2[N]C=CC2=C1 YEDVUDDWJVRKIS-UHFFFAOYSA-N 0.000 description 1
- QRUYYSPCOGSZGQ-UHFFFAOYSA-L cyclopentane;dichlorozirconium Chemical compound Cl[Zr]Cl.[CH]1[CH][CH][CH][CH]1.[CH]1[CH][CH][CH][CH]1 QRUYYSPCOGSZGQ-UHFFFAOYSA-L 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- HLEXTMGMJVVHSM-UHFFFAOYSA-L dichlorozirconium(2+);1,9-dihydrofluoren-1-ide Chemical compound Cl[Zr+2]Cl.C1=C[C-]=C2CC3=CC=CC=C3C2=C1.C1=C[C-]=C2CC3=CC=CC=C3C2=C1 HLEXTMGMJVVHSM-UHFFFAOYSA-L 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 238000012685 gas phase polymerization Methods 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 150000002363 hafnium compounds Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- GEAWFZNTIFJMHR-UHFFFAOYSA-N hepta-1,6-diene Chemical compound C=CCCCC=C GEAWFZNTIFJMHR-UHFFFAOYSA-N 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- NMLXKNNXODLJIN-UHFFFAOYSA-M zinc;carbanide;chloride Chemical compound [CH3-].[Zn+]Cl NMLXKNNXODLJIN-UHFFFAOYSA-M 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- 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
- C07F17/00—Metallocenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03101268 | 2003-05-08 | ||
| US46919103P | 2003-05-09 | 2003-05-09 | |
| PCT/EP2004/004525 WO2004099225A1 (en) | 2003-05-08 | 2004-04-29 | Process for the production of halide metallocene compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006525264A true JP2006525264A (ja) | 2006-11-09 |
| JP2006525264A5 JP2006525264A5 (enExample) | 2007-04-12 |
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| JP2006505316A Pending JP2006525264A (ja) | 2003-05-08 | 2004-04-29 | ハロゲン化メタロセン化合物の製造方法 |
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| Country | Link |
|---|---|
| US (1) | US7468451B2 (enExample) |
| EP (1) | EP1620448B1 (enExample) |
| JP (1) | JP2006525264A (enExample) |
| CN (1) | CN101341162A (enExample) |
| AT (1) | ATE471332T1 (enExample) |
| DE (1) | DE602004027722D1 (enExample) |
| RU (1) | RU2335504C2 (enExample) |
| WO (1) | WO2004099225A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1668019B1 (en) | 2003-09-29 | 2007-01-10 | Basell Polyolefine GmbH | Process for the isomerization of metallocene compounds |
| SG10201403259SA (en) | 2009-06-16 | 2014-10-30 | Chevron Phillips Chemical Co | Oligomerization of alpha olefins using metallocene-ssa catalyst systems and use of the resultant polyalphaolefins to prepare lubricant blends |
| EP2485839A1 (en) * | 2009-10-06 | 2012-08-15 | Chevron Phillips Chemical Company LP | Oligomerization of olefin waxes using metallocene-based catalyst systems |
| US9732300B2 (en) | 2015-07-23 | 2017-08-15 | Chevron Phillipa Chemical Company LP | Liquid propylene oligomers and methods of making same |
| KR101790672B1 (ko) | 2015-08-24 | 2017-10-26 | 주식회사 엘지화학 | 전이 금속 화합물, 이를 포함하는 촉매 조성물 및 이를 이용한 올레핀 중합체의 제조 방법 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH09509149A (ja) * | 1994-01-25 | 1997-09-16 | ザ ダウ ケミカル カンパニー | 金属ヒドロカルビロキシドからのシクロペンタジエニル金属配位錯体の合成 |
| WO2002083699A2 (en) * | 2001-04-10 | 2002-10-24 | Basell Polyolefine Gmbh | Process for the production of monohalide or dihalide metallocene compounds |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA844157B (en) | 1983-06-06 | 1986-01-29 | Exxon Research Engineering Co | Process and catalyst for polyolefin density and molecular weight control |
| PL286365A1 (en) | 1989-08-03 | 1991-04-22 | Exxon Chemical Patents Inc | Method of polymerizing especially ethylene any polymerization catalyst and method of obtaining same |
| EP0672689A1 (en) | 1990-06-22 | 1995-09-20 | Exxon Chemical Patents Inc. | Aluminum-free monocyclopentadienyl metallocene catalysts for olefin polymerization |
| CN1243763C (zh) | 1998-01-14 | 2006-03-01 | 蒙特尔技术有限公司 | 茂金属化合物的制备方法 |
| DE60001902T2 (de) | 1999-06-04 | 2003-11-13 | Basell Polyolefine Gmbh | Verfahren zur herstellung titankomplexen |
| DE19962910A1 (de) * | 1999-12-23 | 2001-07-05 | Targor Gmbh | Chemische Verbindung, Verfahren zu deren Herstellung und deren Verwendung in Katalysatorsystemen zur Herstellung von Polyolefinen |
| DE19962814A1 (de) * | 1999-12-23 | 2001-06-28 | Targor Gmbh | Neues Katalysatorsystem und dessen Verwendung |
| ES2220725T3 (es) | 2000-02-24 | 2004-12-16 | Basell Polyolefine Gmbh | Compuesto organometalico utilizable como c-catalizador para polimerizar olefinas. |
| US7002031B2 (en) * | 2002-01-08 | 2006-02-21 | Basell Polyolefine Gmbh | Preparation of silicon-bridged metallocene compounds |
| US7098354B2 (en) * | 2002-10-25 | 2006-08-29 | Basell Polyolefine Gmbh | Racemoselective synthesis of rac-diorganosilylbis(2-methylbenzo[e]indeyl)zirconium compounds |
| US6869903B2 (en) * | 2002-11-07 | 2005-03-22 | Univation Technologies, Llc | Synthesis of polymerization catalyst components |
-
2004
- 2004-04-29 EP EP04730240A patent/EP1620448B1/en not_active Expired - Lifetime
- 2004-04-29 DE DE602004027722T patent/DE602004027722D1/de not_active Expired - Lifetime
- 2004-04-29 WO PCT/EP2004/004525 patent/WO2004099225A1/en not_active Ceased
- 2004-04-29 JP JP2006505316A patent/JP2006525264A/ja active Pending
- 2004-04-29 CN CNA2004800124121A patent/CN101341162A/zh active Pending
- 2004-04-29 US US10/555,434 patent/US7468451B2/en not_active Expired - Fee Related
- 2004-04-29 AT AT04730240T patent/ATE471332T1/de not_active IP Right Cessation
- 2004-04-29 RU RU2005138107/04A patent/RU2335504C2/ru active
Patent Citations (2)
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| JPH09509149A (ja) * | 1994-01-25 | 1997-09-16 | ザ ダウ ケミカル カンパニー | 金属ヒドロカルビロキシドからのシクロペンタジエニル金属配位錯体の合成 |
| WO2002083699A2 (en) * | 2001-04-10 | 2002-10-24 | Basell Polyolefine Gmbh | Process for the production of monohalide or dihalide metallocene compounds |
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| JPN6009041150, Ｒｏｂｅｒｔ Ｃｈｏｕｋｒｏｕｎ ｅｔ ａｌ．, "Ｓｕｂｓｔｉｔｕｔｅｄ Ｃｙｃｌｏｐｅｎｔａｄｉｅｎｙｌ Ｐｈｏｓｐｈｉｎｏｍｅｔｈｙｌ Ｃｏｍｐｌｅｘｅｓ ｏｆ Ｚｉｒｃｏｎｉｕｍ． Ｓｙｎｔｈｅｓｉｓ， Ｃｈｅｍｉｃａｌ Ｃｈａｒａｃｔｅｒｉｓ", Ｏｒｇａｎｏｍｅｔａｌｌｉｃｓ, 1990, Ｖｏｌ．９， Ｎｏ．６, ｐ．１９８２−１９８７ * |
| JPN6009041151, Ｍａｒｋｕｓ Ｒｉｎｇｗａｌｄ ｅｔ ａｌ．, "Ａｓｙｍｍｅｔｒｉｃ Ｔｈｅｒｍａｌ Ｔｒａｎｓｆｏｒｍａｔｉｏｎ， ａ Ｎｅｗ Ｗａｙ ｔｏ Ｅｎａｎｔｉｏｐｕｒｅ Ｂｉｐｈｅｎｙｌ−Ｂｒｉｄｇｅｄ Ｔｉｔａｎｏｃｅｎｅ ａｎｄ Ｚｉｒｃｏｎｏｃ", Ｊｏｕｒｎａｌ ｏｆ ｔｈｅ Ａｍｅｒｉｃａｎ Ｃｈｅｍｉｃａｌ Ｓｏｃｉｅｔｙ, 1999, Ｖｏｌ．１２１， Ｎｏ．７, ｐ．１５２４−１５２７ * |
| JPN6009041154, Ｊｏｏｎ Ｔ． Ｐａｒｋ ｅｔ ａｌ．, "Ａｎ ｅｆｆｉｃｉｅｎｔ ｓｙｎｔｈｅｔｉｃ ｍｅｔｈｏｄ ｏｆ ａｎｓａ−ｚｉｒｃｏｎｏｃｅｎｅ ｄｉｍｅｔｈｙｌ ｃｏｍｐｌｅｘｅｓ ｖｉａ Ｍｅ２ＺｒＣｌ２", Ｊｏｕｒｎａｌ ｏｆ Ｏｒｇａｎｏｍｅｔａｌｌｉｃ Ｃｈｅｍｉｓｔｒｙ, 1997, Ｖｏｌ．５３５， Ｎｏ．１−２, ｐ．２９−３２ * |
| JPN6009041157, Ｃｏｌｉｎ Ｌ． Ｂｅｓｗｉｃｋ ａｎｄ Ｔｏｂｉｎ Ｊ． Ｍａｒｋｓ, "Ｍｅｔａｌ−Ａｌｋｙｌ Ｇｒｏｕｐ Ｅｆｆｅｃｔｓ ｏｎ ｔｈｅ Ｔｈｅｒｍｏｄｙｎａｍｉｃ Ｓｔａｂｉｌｉｔｙ ａｎｄ Ｓｔｅｒｅｏｃｈｅｍｉｃａｌ Ｍｏｂｉｌｉｔｙ ｏｆ Ｂ（Ｃ６Ｆ５）３−Ｄｅｒ", Ｊｏｕｒｎａｌ ｏｆ ｔｈｅ Ａｍｅｒｉｃａｎ Ｃｈｅｍｉｃａｌ Ｓｏｃｉｅｔｙ, 2000, Ｖｏｌ．１２２， Ｎｏ．４２, ｐ．１０３５８−１０３７０ * |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2335504C2 (ru) | 2008-10-10 |
| WO2004099225A1 (en) | 2004-11-18 |
| EP1620448B1 (en) | 2010-06-16 |
| US20070043228A1 (en) | 2007-02-22 |
| US7468451B2 (en) | 2008-12-23 |
| ATE471332T1 (de) | 2010-07-15 |
| DE602004027722D1 (de) | 2010-07-29 |
| RU2005138107A (ru) | 2006-04-27 |
| CN101341162A (zh) | 2009-01-07 |
| EP1620448A1 (en) | 2006-02-01 |
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