DE69903388T2 - Verfahren zur herstellung von metallocenen - Google Patents
Verfahren zur herstellung von metallocenenInfo
- Publication number
- DE69903388T2 DE69903388T2 DE69903388T DE69903388T DE69903388T2 DE 69903388 T2 DE69903388 T2 DE 69903388T2 DE 69903388 T DE69903388 T DE 69903388T DE 69903388 T DE69903388 T DE 69903388T DE 69903388 T2 DE69903388 T2 DE 69903388T2
- Authority
- DE
- Germany
- Prior art keywords
- group
- process according
- sub2
- range
- ind
- 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.)
- Expired - Lifetime
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims description 54
- -1 C3-C20 cycloalkyl Chemical group 0.000 claims description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 48
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 24
- 239000003446 ligand Substances 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 15
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 14
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 229910007932 ZrCl4 Inorganic materials 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 229910052726 zirconium Inorganic materials 0.000 claims description 13
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 11
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 10
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 10
- 239000000010 aprotic solvent Substances 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 9
- 229910052732 germanium Inorganic materials 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052710 silicon Inorganic materials 0.000 claims description 9
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 7
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 150000003624 transition metals Chemical class 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000013256 coordination polymer Substances 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- 229910003074 TiCl4 Inorganic materials 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229910052735 hafnium Inorganic materials 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 3
- 229910003865 HfCl4 Inorganic materials 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910019804 NbCl5 Inorganic materials 0.000 claims description 2
- 229910018057 ScCl3 Inorganic materials 0.000 claims description 2
- 229910011005 Ti(OPr)4 Inorganic materials 0.000 claims description 2
- 229910009523 YCl3 Inorganic materials 0.000 claims description 2
- 229910008110 Zr(OPr)4 Inorganic materials 0.000 claims description 2
- 150000001255 actinides Chemical group 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- PDPJQWYGJJBYLF-UHFFFAOYSA-J hafnium tetrachloride Chemical compound Cl[Hf](Cl)(Cl)Cl PDPJQWYGJJBYLF-UHFFFAOYSA-J 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 150000002602 lanthanoids Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- YHBDIEWMOMLKOO-UHFFFAOYSA-I pentachloroniobium Chemical compound Cl[Nb](Cl)(Cl)(Cl)Cl YHBDIEWMOMLKOO-UHFFFAOYSA-I 0.000 claims description 2
- XTTBFCWRLDKOQU-UHFFFAOYSA-N propan-1-ol;titanium Chemical compound [Ti].CCCO.CCCO.CCCO.CCCO XTTBFCWRLDKOQU-UHFFFAOYSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- PCMOZDDGXKIOLL-UHFFFAOYSA-K yttrium chloride Chemical compound [Cl-].[Cl-].[Cl-].[Y+3] PCMOZDDGXKIOLL-UHFFFAOYSA-K 0.000 claims description 2
- 101100311330 Schizosaccharomyces pombe (strain 972 / ATCC 24843) uap56 gene Proteins 0.000 description 58
- 101150018444 sub2 gene Proteins 0.000 description 58
- 239000000243 solution Substances 0.000 description 28
- 230000015572 biosynthetic process Effects 0.000 description 22
- 239000007787 solid Substances 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 12
- 239000000725 suspension Substances 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- 241000349731 Afzelia bipindensis Species 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 150000001336 alkenes Chemical class 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000002168 alkylating agent Substances 0.000 description 6
- 229940100198 alkylating agent Drugs 0.000 description 6
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 6
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- GCZYAOLYVIHWLC-UHFFFAOYSA-N 1-[2-(4,7-dimethyl-1h-inden-1-yl)ethyl]-4,7-dimethyl-1h-indene Chemical compound C1=CC(C(=CC=C2C)C)=C2C1CCC1C(C(C)=CC=C2C)=C2C=C1 GCZYAOLYVIHWLC-UHFFFAOYSA-N 0.000 description 3
- IPBTZXODRJJQBJ-UHFFFAOYSA-N 3-tert-butyl-1-[(3-tert-butyl-1h-inden-1-yl)methyl]-1h-indene Chemical compound C12=CC=CC=C2C(C(C)(C)C)=CC1CC1C2=CC=CC=C2C(C(C)(C)C)=C1 IPBTZXODRJJQBJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000003426 co-catalyst Substances 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- AQZWEFBJYQSQEH-UHFFFAOYSA-N 2-methyloxaluminane Chemical compound C[Al]1CCCCO1 AQZWEFBJYQSQEH-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- LUKADOYBIWUGAR-UHFFFAOYSA-N ClC.C1=CC2=CC=CC=C2C1[Zr](=C(C)C)C1C2=CC=CC=C2C=C1 Chemical compound ClC.C1=CC2=CC=CC=C2C1[Zr](=C(C)C)C1C2=CC=CC=C2C=C1 LUKADOYBIWUGAR-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
- 239000007818 Grignard reagent Substances 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-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
- 239000007983 Tris buffer Substances 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 229940077746 antacid containing aluminium compound Drugs 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000001768 cations 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
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 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
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 1
- PALFTCLHKGGKDW-UHFFFAOYSA-N 1-[2-(1h-inden-1-yl)propan-2-yl]-1h-indene Chemical compound C1=CC2=CC=CC=C2C1C(C)(C)C1C2=CC=CC=C2C=C1 PALFTCLHKGGKDW-UHFFFAOYSA-N 0.000 description 1
- 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
- HANWWAAUFXCNBS-UHFFFAOYSA-N 2,6,6-tris(2-methylpropyl)oxaluminane Chemical compound CC(C)C[Al]1CCCC(CC(C)C)(CC(C)C)O1 HANWWAAUFXCNBS-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
- FSWNZCWHTXTQBY-UHFFFAOYSA-N 4,6-dimethylhept-1-ene Chemical compound CC(C)CC(C)CC=C FSWNZCWHTXTQBY-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- MWROANXKQLDDCZ-UHFFFAOYSA-L [Cl-].[Cl-].C1=C(C(C)(C)C)C2=CC=CC=C2C1[Zr+2](=C)C1C=C(C(C)(C)C)C2=CC=CC=C21 Chemical compound [Cl-].[Cl-].C1=C(C(C)(C)C)C2=CC=CC=C2C1[Zr+2](=C)C1C=C(C(C)(C)C)C2=CC=CC=C21 MWROANXKQLDDCZ-UHFFFAOYSA-L 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- HIGRAKVNKLCVCA-UHFFFAOYSA-N alumine Chemical compound C1=CC=[Al]C=C1 HIGRAKVNKLCVCA-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000004411 aluminium Substances 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
- 150000001450 anions Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- MMUJVDPVMYOVAM-UHFFFAOYSA-N cyclopenta-1,3-diene 5-methylcyclopenta-1,3-diene zirconium(2+) Chemical compound [Zr++].c1cc[cH-]c1.C[c-]1cccc1 MMUJVDPVMYOVAM-UHFFFAOYSA-N 0.000 description 1
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000012685 gas phase polymerization Methods 0.000 description 1
- 238000007429 general method Methods 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
- 239000001282 iso-butane Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-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
- 125000002097 pentamethylcyclopentadienyl group Chemical group 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
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003623 transition metal compounds 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
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98200077 | 1998-01-14 | ||
| PCT/EP1999/000188 WO1999036427A1 (en) | 1998-01-14 | 1999-01-14 | Process for the preparation of metallocene compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69903388D1 DE69903388D1 (de) | 2002-11-14 |
| DE69903388T2 true DE69903388T2 (de) | 2003-06-18 |
Family
ID=8233295
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69903388T Expired - Lifetime DE69903388T2 (de) | 1998-01-14 | 1999-01-14 | Verfahren zur herstellung von metallocenen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6191294B1 (enExample) |
| EP (1) | EP0979232B1 (enExample) |
| JP (1) | JP4208265B2 (enExample) |
| KR (1) | KR20000076111A (enExample) |
| CN (1) | CN1243763C (enExample) |
| CA (1) | CA2283880A1 (enExample) |
| DE (1) | DE69903388T2 (enExample) |
| WO (1) | WO1999036427A1 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20010014072A (ko) | 1998-04-21 | 2001-02-26 | 간디 지오프레이 에이치. | 에틸렌과 알파-올레핀의 공중합체의 제조 방법 |
| JP2002530285A (ja) | 1998-11-18 | 2002-09-17 | バセル テクノロジー カンパニー ビー．ブイ． | オレフィン−重合−触媒成分としてのメチレン橋架けメタロセン |
| US6774253B1 (en) | 1999-06-04 | 2004-08-10 | Basell Polyolefine Gmbh | Process for the preparation of titanium complexes |
| ATE430753T1 (de) * | 2000-01-18 | 2009-05-15 | Basell Polyolefine Gmbh | Ligand für einen metallocenkatalysator für die polymerisation von propylen und dessen herstellungsverfahren |
| DE60226427D1 (de) | 2001-04-10 | 2008-06-19 | Basell Polyolefine Gmbh | Verfahren zur herstellung von mono oder bis halogensubstituierten metallozenverbindungen |
| WO2002100909A1 (en) | 2001-06-12 | 2002-12-19 | Basell Polyolefine Gmbh | Process for the polymerization of 1-butene |
| EP1397371B1 (en) | 2001-06-22 | 2006-03-22 | Basell Polyolefine GmbH | Metallocenes and their use in catalyst systems for producing olefin polymers |
| JP2004535505A (ja) * | 2001-07-17 | 2004-11-25 | バセル ポリオレフィン ジーエムビーエイチ | オレフィン（共）重合のための多工程方法 |
| US7141637B2 (en) | 2001-11-30 | 2006-11-28 | Basell Polyolefine Gmbh | Metallocene compounds and process for the preparation of propylene polymers |
| DE10200422A1 (de) * | 2002-01-08 | 2003-07-17 | Basell Polyolefine Gmbh | Verfahren zur Herstellung von Dialkyl-ansa-Metallocenen |
| JP4417719B2 (ja) * | 2002-01-08 | 2010-02-17 | バーゼル・ポリオレフィン・ゲーエムベーハー | シリコン橋状メタロセン化合物の製造 |
| ATE445651T1 (de) | 2002-09-06 | 2009-10-15 | Basell Polyolefine Gmbh | Verfahren zur copolymerisation von ethylen |
| US7176158B2 (en) * | 2002-10-25 | 2007-02-13 | Exxonmobil Chemical Patents Inc. | Polymerization catalyst composition |
| US6693155B1 (en) * | 2003-03-05 | 2004-02-17 | Equistar Chemicals, Lp | Propylene polymerization process |
| EP1620448B1 (en) | 2003-05-08 | 2010-06-16 | Basell Polyolefine GmbH | Process for the production of halide metallocene compounds |
| RU2351603C2 (ru) | 2003-09-29 | 2009-04-10 | Базелль Полиолефине Гмбх | Способ изомеризации соединений металлоцена |
| CN101245084B (zh) * | 2007-02-14 | 2013-02-20 | 中国石油天然气股份有限公司 | 含膦取代乙烯基茂金属催化剂及其制备方法和应用 |
| JP5461409B2 (ja) * | 2007-10-04 | 2014-04-02 | バーゼル・ポリオレフィン・ゲーエムベーハー | 触媒ペーストの製造法およびその生成物 |
| WO2010022878A1 (en) | 2008-08-25 | 2010-03-04 | Basell Polyolefine Gmbh | Preparation of ansa metallocene compounds |
| MY173869A (en) | 2009-06-16 | 2020-02-25 | Chevron Phillips Chemical Co Lp | Oligomerization of alpha olefins using metallocene-ssa catalyst systems and use of the resultant polyalphaolefins to prepare lubricant blends |
| WO2011044150A1 (en) * | 2009-10-06 | 2011-04-14 | Chevron Phillips Chemical Company Lp | Oligomerization of olefin waxes using metallocene-based catalyst systems |
| KR20140075589A (ko) | 2012-12-11 | 2014-06-19 | 주식회사 엘지화학 | 신규한 리간드 화합물, 이의 제조방법, 전이금속 화합물, 및 이의 제조방법 |
| US9732300B2 (en) | 2015-07-23 | 2017-08-15 | Chevron Phillipa Chemical Company LP | Liquid propylene oligomers and methods of making same |
| JP6038375B1 (ja) * | 2016-06-29 | 2016-12-07 | ポリプラスチックス株式会社 | 触媒の製造方法 |
| KR102073252B1 (ko) * | 2016-12-05 | 2020-02-04 | 주식회사 엘지화학 | 올레핀 공중합체 합성용 촉매 조성물 및 올레핀 공중합체의 제조 방법 |
| KR102765043B1 (ko) * | 2018-05-16 | 2025-02-07 | 주식회사 엘지화학 | 테트라하이드로인덴 유도체로부터 메탈로센 화합물을 제조하는 방법 |
| KR102398899B1 (ko) * | 2019-11-29 | 2022-05-17 | 디엘케미칼 주식회사 | 낮은 점도 알파-올레핀 올리고머 및 이의 제조방법 |
| WO2021173361A1 (en) | 2020-02-24 | 2021-09-02 | Exxonmobil Chemical Patents Inc. | Ansa-bis(inden-2-yl) catalysts for producing vinylidene-terminated polyalphaolefins |
Family Cites Families (6)
| 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 |
| US5057475A (en) * | 1989-09-13 | 1991-10-15 | Exxon Chemical Patents Inc. | Mono-Cp heteroatom containing group IVB transition metal complexes with MAO: supported catalyst for olefin polymerization |
| EP0551277B2 (en) * | 1990-06-22 | 2005-03-09 | ExxonMobil Chemical Patents Inc. | Aluminum-free monocyclopentadienyl metallocene catalysts for olefin polymerization |
| IT1256259B (it) * | 1992-12-30 | 1995-11-29 | Montecatini Tecnologie Srl | Composti mettallocenici aventi leganti di tipo fluorenilico |
| WO1996019488A1 (en) | 1994-12-21 | 1996-06-27 | Exxon Chemical Patents Inc. | A method of preparing high purity racemic metallocene alkyls and use thereof |
| ES2203965T3 (es) | 1997-03-29 | 2004-04-16 | Basell Polyolefine Gmbh | Metalocenos y catalizadores para la polimerizacion de olefinas. |
-
1999
- 1999-01-14 WO PCT/EP1999/000188 patent/WO1999036427A1/en not_active Ceased
- 1999-01-14 JP JP53674499A patent/JP4208265B2/ja not_active Expired - Lifetime
- 1999-01-14 CN CNB99800037XA patent/CN1243763C/zh not_active Expired - Fee Related
- 1999-01-14 EP EP99902538A patent/EP0979232B1/en not_active Expired - Lifetime
- 1999-01-14 CA CA002283880A patent/CA2283880A1/en not_active Abandoned
- 1999-01-14 KR KR1019997008199A patent/KR20000076111A/ko not_active Withdrawn
- 1999-01-14 DE DE69903388T patent/DE69903388T2/de not_active Expired - Lifetime
- 1999-09-13 US US09/381,075 patent/US6191294B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2283880A1 (en) | 1999-07-22 |
| JP4208265B2 (ja) | 2009-01-14 |
| CN1255925A (zh) | 2000-06-07 |
| EP0979232A1 (en) | 2000-02-16 |
| EP0979232B1 (en) | 2002-10-09 |
| KR20000076111A (ko) | 2000-12-26 |
| CN1243763C (zh) | 2006-03-01 |
| WO1999036427A1 (en) | 1999-07-22 |
| JP2001516367A (ja) | 2001-09-25 |
| DE69903388D1 (de) | 2002-11-14 |
| US6191294B1 (en) | 2001-02-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |