JP3986441B2 - モノハライドまたはジハライドメタロセン化合物の製造方法 - Google Patents
モノハライドまたはジハライドメタロセン化合物の製造方法 Download PDFInfo
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- JP3986441B2 JP3986441B2 JP2002581454A JP2002581454A JP3986441B2 JP 3986441 B2 JP3986441 B2 JP 3986441B2 JP 2002581454 A JP2002581454 A JP 2002581454A JP 2002581454 A JP2002581454 A JP 2002581454A JP 3986441 B2 JP3986441 B2 JP 3986441B2
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 43
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 13
- -1 hydrocarbon radical Chemical class 0.000 claims abstract description 70
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 18
- 230000002140 halogenating effect Effects 0.000 claims abstract description 17
- 229910052751 metal Inorganic materials 0.000 claims abstract description 13
- 239000002184 metal Substances 0.000 claims abstract description 13
- 239000010936 titanium Chemical group 0.000 claims abstract description 11
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 9
- 230000000737 periodic effect Effects 0.000 claims abstract description 9
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 6
- 229910052735 hafnium Chemical group 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 5
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims abstract description 4
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical group [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 239000000460 chlorine Substances 0.000 claims description 49
- 238000006243 chemical reaction Methods 0.000 claims description 33
- 229910007926 ZrCl Inorganic materials 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 26
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 21
- 239000003446 ligand Substances 0.000 claims description 17
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 239000011777 magnesium Substances 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 9
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 9
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 239000011630 iodine Substances 0.000 claims description 9
- 229910003902 SiCl 4 Inorganic materials 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 8
- 229910052710 silicon Inorganic materials 0.000 claims description 8
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 7
- 229910052732 germanium Inorganic materials 0.000 claims description 7
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 229910052749 magnesium Inorganic materials 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 238000000746 purification Methods 0.000 claims description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 abstract description 7
- 238000007254 oxidation reaction Methods 0.000 abstract description 7
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 4
- 229930195733 hydrocarbon Natural products 0.000 abstract description 4
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract description 2
- HPYIUKIBUJFXII-UHFFFAOYSA-N Cyclopentadienyl radical Chemical compound [CH]1C=CC=C1 HPYIUKIBUJFXII-UHFFFAOYSA-N 0.000 abstract 2
- 229910052755 nonmetal Inorganic materials 0.000 abstract 1
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 48
- 239000000243 solution Substances 0.000 description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 230000015572 biosynthetic process Effects 0.000 description 27
- 238000005160 1H NMR spectroscopy Methods 0.000 description 26
- 238000003786 synthesis reaction Methods 0.000 description 22
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 20
- 239000000725 suspension Substances 0.000 description 20
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
- 238000003756 stirring Methods 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000007787 solid 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 239000000010 aprotic solvent Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 4
- BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- 238000001914 filtration Methods 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
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical group [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 3
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- AQZWEFBJYQSQEH-UHFFFAOYSA-N 2-methyloxaluminane Chemical compound C[Al]1CCCCO1 AQZWEFBJYQSQEH-UHFFFAOYSA-N 0.000 description 2
- 241000349731 Afzelia bipindensis Species 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 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
- 239000007983 Tris buffer Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 230000017858 demethylation Effects 0.000 description 2
- 238000010520 demethylation reaction Methods 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 229910052747 lanthanoid Inorganic materials 0.000 description 2
- 150000002602 lanthanoids Chemical class 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 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
- 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
- 238000010992 reflux Methods 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 2
- 239000004711 α-olefin Substances 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
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
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- ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 description 1
- USVQDQRLYYGLPV-UHFFFAOYSA-N 2-(2,4,4-trimethylpentyl)oxaluminane Chemical compound CC(C)(C)CC(C)C[Al]1CCCCO1 USVQDQRLYYGLPV-UHFFFAOYSA-N 0.000 description 1
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- LMATZHARTKIWDW-UHFFFAOYSA-L C12=CC=CC=C2N(CC)C2=C1C1=CC=CC=C1C2[Ti](Cl)(Cl)(NC(C)(C)C)[SiH](C)C Chemical compound C12=CC=CC=C2N(CC)C2=C1C1=CC=CC=C1C2[Ti](Cl)(Cl)(NC(C)(C)C)[SiH](C)C LMATZHARTKIWDW-UHFFFAOYSA-L 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
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- 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
- COOXAWDWHWRVRD-UHFFFAOYSA-N C[Ti]C Chemical compound C[Ti]C COOXAWDWHWRVRD-UHFFFAOYSA-N 0.000 description 1
- 101100219382 Caenorhabditis elegans cah-2 gene Proteins 0.000 description 1
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- 244000248349 Citrus limon Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
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- 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
- 101100010166 Mus musculus Dok3 gene Proteins 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- HXXGXRJQJSJMAH-UHFFFAOYSA-L [Cl-].[Cl-].C(C)(C)C1=CC(C=C1)[Zr+2]C1C2=CC=CC=C2C=2C=CC=CC1=2 Chemical compound [Cl-].[Cl-].C(C)(C)C1=CC(C=C1)[Zr+2]C1C2=CC=CC=C2C=2C=CC=CC1=2 HXXGXRJQJSJMAH-UHFFFAOYSA-L 0.000 description 1
- PFXCHHSGDVHOAR-UHFFFAOYSA-L [Cl-].[Cl-].C(C)C1=CC(C=C1)[Zr+2]C1C2=CC=CC=C2C=2C=CC=CC1=2 Chemical compound [Cl-].[Cl-].C(C)C1=CC(C=C1)[Zr+2]C1C2=CC=CC=C2C=2C=CC=CC1=2 PFXCHHSGDVHOAR-UHFFFAOYSA-L 0.000 description 1
- NOQWABVRFAHTQD-UHFFFAOYSA-L [Cl-].[Cl-].C12=CC=CCC2CCC1[Zr+2]C1C2=CC=CCC2CC1 Chemical compound [Cl-].[Cl-].C12=CC=CCC2CCC1[Zr+2]C1C2=CC=CCC2CC1 NOQWABVRFAHTQD-UHFFFAOYSA-L 0.000 description 1
- 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
- UVVHOKMKYKTWHC-UHFFFAOYSA-L [Cl-].[Cl-].CC1=Cc2c([C@H]1[Zr++]([C@@H]1C(C)=Cc3c1c(C)ccc3C)=[Si](C)C)c(C)ccc2C Chemical compound [Cl-].[Cl-].CC1=Cc2c([C@H]1[Zr++]([C@@H]1C(C)=Cc3c1c(C)ccc3C)=[Si](C)C)c(C)ccc2C UVVHOKMKYKTWHC-UHFFFAOYSA-L 0.000 description 1
- YVQPUXMWIMJFBY-UHFFFAOYSA-L [Cl-].[Cl-].CC1=Cc2c(cc(C)cc2C)C1[Zr++](C1C(C)=Cc2c1cc(C)cc2C)=[Si](C)C Chemical compound [Cl-].[Cl-].CC1=Cc2c(cc(C)cc2C)C1[Zr++](C1C(C)=Cc2c1cc(C)cc2C)=[Si](C)C YVQPUXMWIMJFBY-UHFFFAOYSA-L 0.000 description 1
- IOEZEGGCMNVLHK-UHFFFAOYSA-L [Cl-].[Cl-].CC1=Cc2cc(C)c(C)cc2C1[Zr++](C1C(C)=Cc2cc(C)c(C)cc12)=[Si](C)C Chemical compound [Cl-].[Cl-].CC1=Cc2cc(C)c(C)cc2C1[Zr++](C1C(C)=Cc2cc(C)c(C)cc12)=[Si](C)C IOEZEGGCMNVLHK-UHFFFAOYSA-L 0.000 description 1
- 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
- CGELJBSWQTYCIY-UHFFFAOYSA-L [Cl-].[Cl-].CC1=Cc2ccccc2[C@H]1[Zr++]([C@@H]1C(C)=Cc2ccccc12)=[Si](C)C Chemical compound [Cl-].[Cl-].CC1=Cc2ccccc2[C@H]1[Zr++]([C@@H]1C(C)=Cc2ccccc12)=[Si](C)C CGELJBSWQTYCIY-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
- 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
- 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
- 229910052782 aluminium Inorganic materials 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
- 239000012298 atmosphere Substances 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000005890 dearylation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 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
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000605 extraction 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
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 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
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
- DWWZPYPYUFXZTL-UHFFFAOYSA-N lithium;2h-inden-2-ide Chemical compound [Li+].C1=CC=C2[CH-]C=CC2=C1 DWWZPYPYUFXZTL-UHFFFAOYSA-N 0.000 description 1
- 229960002523 mercuric chloride Drugs 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 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
- 230000003287 optical effect Effects 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 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
- HKVFGFGPRISDFM-UHFFFAOYSA-N tris(2,3,3-trimethylbutyl)alumane Chemical compound CC(C)(C)C(C)C[Al](CC(C)C(C)(C)C)CC(C)C(C)(C)C HKVFGFGPRISDFM-UHFFFAOYSA-N 0.000 description 1
- SSEXLBWMXFFGTD-UHFFFAOYSA-N tris(2,3-dimethylbutyl)alumane Chemical compound CC(C)C(C)C[Al](CC(C)C(C)C)CC(C)C(C)C SSEXLBWMXFFGTD-UHFFFAOYSA-N 0.000 description 1
- WUGMXCQCNQHHDC-UHFFFAOYSA-N tris(2,3-dimethylheptyl)alumane Chemical compound CCCCC(C)C(C)C[Al](CC(C)C(C)CCCC)CC(C)C(C)CCCC WUGMXCQCNQHHDC-UHFFFAOYSA-N 0.000 description 1
- VGONMIOMLRCRSS-UHFFFAOYSA-N tris(2,3-dimethylhexyl)alumane Chemical compound CCCC(C)C(C)C[Al](CC(C)C(C)CCC)CC(C)C(C)CCC VGONMIOMLRCRSS-UHFFFAOYSA-N 0.000 description 1
- BENYMJNPVWYYES-UHFFFAOYSA-N tris(2,3-dimethylpentyl)alumane Chemical compound CCC(C)C(C)C[Al](CC(C)C(C)CC)CC(C)C(C)CC BENYMJNPVWYYES-UHFFFAOYSA-N 0.000 description 1
- XZIKSWMNFLIAQP-UHFFFAOYSA-N tris(2,4,4-trimethylpentyl)alumane Chemical compound CC(C)(C)CC(C)C[Al](CC(C)CC(C)(C)C)CC(C)CC(C)(C)C XZIKSWMNFLIAQP-UHFFFAOYSA-N 0.000 description 1
- AMPVHNIRJXJXEN-UHFFFAOYSA-N tris(3-ethyl-2-methylpentyl)alumane Chemical compound CCC(CC)C(C)C[Al](CC(C)C(CC)CC)CC(C)C(CC)CC AMPVHNIRJXJXEN-UHFFFAOYSA-N 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/943—Polymerization with metallocene catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01201327 | 2001-04-10 | ||
| PCT/EP2002/003697 WO2002083699A2 (en) | 2001-04-10 | 2002-04-03 | Process for the production of monohalide or dihalide metallocene compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004531529A JP2004531529A (ja) | 2004-10-14 |
| JP2004531529A5 JP2004531529A5 (enExample) | 2005-12-22 |
| JP3986441B2 true JP3986441B2 (ja) | 2007-10-03 |
Family
ID=8180134
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002581454A Expired - Lifetime JP3986441B2 (ja) | 2001-04-10 | 2002-04-03 | モノハライドまたはジハライドメタロセン化合物の製造方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US6987196B2 (enExample) |
| EP (1) | EP1381618B1 (enExample) |
| JP (1) | JP3986441B2 (enExample) |
| AT (1) | ATE394407T1 (enExample) |
| DE (1) | DE60226427D1 (enExample) |
| WO (1) | WO2002083699A2 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4571798B2 (ja) * | 2001-06-12 | 2010-10-27 | バーゼル・ポリオレフィン・ゲーエムベーハー | １−ブテンの重合方法 |
| WO2002100909A1 (en) * | 2001-06-12 | 2002-12-19 | Basell Polyolefine Gmbh | Process for the polymerization of 1-butene |
| DE60210089T2 (de) | 2001-06-22 | 2006-10-19 | Basell Polyolefine Gmbh | Metallocene, verwendung in katalysatoren für olefinpolymerisation |
| ES2268126T3 (es) | 2001-11-30 | 2007-03-16 | Basell Polyolefine Gmbh | Compuestos de metaloceno y procedimiento para la preparacion de polimeros de propileno. |
| EP1539843B1 (en) * | 2002-09-06 | 2009-10-14 | Basell Polyolefine GmbH | Process for the copolymerization of ethylene |
| DE60329523D1 (de) * | 2002-12-04 | 2009-11-12 | Basell Polyolefine Gmbh | 1-Buten-Copolymere und Herstellungsverfahren dafür |
| US7589160B2 (en) * | 2002-12-04 | 2009-09-15 | Basell Polyolefine Gmbh | Process for preparing 1-butene polymers |
| ATE471332T1 (de) * | 2003-05-08 | 2010-07-15 | Basell Polyolefine Gmbh | Verfahren zur herstellung von halogenidmetallocenverbindungen |
| BRPI0414762A (pt) | 2003-09-29 | 2006-11-28 | Basell Polyolefine Gmbh | processo para a isomerização de compostos metalocênicos |
| SG11201700464RA (en) * | 2014-07-21 | 2017-02-27 | Tinymos Private Ltd | Image capturing device and method |
| WO2016171808A1 (en) | 2015-04-20 | 2016-10-27 | Exxonmobil Chemical Patents Inc. | Catalyst composition comprising fluorided support and processes for use thereof |
| US9796795B2 (en) | 2015-01-14 | 2017-10-24 | Exxonmobil Chemical Patents Inc. | Tetrahydroindacenyl catalyst composition, catalyst system, and processes for use thereof |
| EP3274380B1 (en) | 2015-04-20 | 2020-08-19 | ExxonMobil Chemical Patents Inc. | Catalyst composition comprising fluorided support and processes for use thereof |
| US9803037B1 (en) | 2016-05-03 | 2017-10-31 | Exxonmobil Chemical Patents Inc. | Tetrahydro-as-indacenyl catalyst composition, catalyst system, and processes for use thereof |
| US10703838B2 (en) | 2017-10-31 | 2020-07-07 | Exxonmobil Chemical Patents Inc. | Mixed catalyst systems with four metallocenes on a single support |
Family Cites Families (10)
| 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 |
| TW294669B (enExample) | 1992-06-27 | 1997-01-01 | Hoechst Ag | |
| DE69617706T2 (de) * | 1995-09-07 | 2002-07-18 | MERCK & CO., INC. | Ein verfahren zur herstellung von dimethyl-titanocen |
| JP3694371B2 (ja) | 1996-10-04 | 2005-09-14 | 関東化学株式会社 | メタロセン化合物の新規な合成方法 |
| JP3228328B2 (ja) * | 1996-12-25 | 2001-11-12 | 日亜化学工業株式会社 | メタロセン化合物の合成方法 |
| WO1998057996A1 (en) | 1997-06-14 | 1998-12-23 | The Board Of Trustees Of The Leland Stanford, Jr. University | ETHYLENE ENHANCEMENT OF PROCESSES FOR SYNTHESIS OF HIGH MELTING THERMOPLASTIC ELASTOMERIC α-OLEFIN POLYMERS (PRE/EPE EFFECTS) |
| CA2283880A1 (en) | 1998-01-14 | 1999-07-22 | Montell Technology Company B.V. | Process for the preparation of metallocene compounds |
| KR20010072229A (ko) | 1999-06-04 | 2001-07-31 | 간디 지오프레이 에이치. | 티타늄 착물의 제조 방법 |
| ATE430753T1 (de) | 2000-01-18 | 2009-05-15 | Basell Polyolefine Gmbh | Ligand für einen metallocenkatalysator für die polymerisation von propylen und dessen herstellungsverfahren |
| JP2002088092A (ja) * | 2000-09-12 | 2002-03-27 | Kanto Chem Co Inc | 新規な有機金属錯体及びこれを中間体とした高純度有機金属錯体の合成方法 |
-
2002
- 2002-04-03 EP EP02745208A patent/EP1381618B1/en not_active Expired - Lifetime
- 2002-04-03 DE DE60226427T patent/DE60226427D1/de not_active Expired - Lifetime
- 2002-04-03 AT AT02745208T patent/ATE394407T1/de not_active IP Right Cessation
- 2002-04-03 JP JP2002581454A patent/JP3986441B2/ja not_active Expired - Lifetime
- 2002-04-03 US US10/474,596 patent/US6987196B2/en not_active Expired - Lifetime
- 2002-04-03 WO PCT/EP2002/003697 patent/WO2002083699A2/en not_active Ceased
-
2005
- 2005-09-27 US US11/237,588 patent/US7115761B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US7115761B2 (en) | 2006-10-03 |
| EP1381618B1 (en) | 2008-05-07 |
| ATE394407T1 (de) | 2008-05-15 |
| DE60226427D1 (de) | 2008-06-19 |
| JP2004531529A (ja) | 2004-10-14 |
| US6987196B2 (en) | 2006-01-17 |
| US20060025621A1 (en) | 2006-02-02 |
| WO2002083699A2 (en) | 2002-10-24 |
| US20040147770A1 (en) | 2004-07-29 |
| EP1381618A2 (en) | 2004-01-21 |
| WO2002083699A3 (en) | 2003-05-15 |
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