JP4360754B2 - ラセミメタロセン錯体の選択的製造 - Google Patents
ラセミメタロセン錯体の選択的製造 Download PDFInfo
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- JP4360754B2 JP4360754B2 JP2000512843A JP2000512843A JP4360754B2 JP 4360754 B2 JP4360754 B2 JP 4360754B2 JP 2000512843 A JP2000512843 A JP 2000512843A JP 2000512843 A JP2000512843 A JP 2000512843A JP 4360754 B2 JP4360754 B2 JP 4360754B2
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- Prior art keywords
- alkyl
- aryl
- carbon atoms
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- 238000002360 preparation method Methods 0.000 title description 2
- 125000003118 aryl group Chemical group 0.000 claims abstract description 98
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 18
- 150000003624 transition metals Chemical class 0.000 claims abstract description 16
- 229910052784 alkaline earth metal Chemical class 0.000 claims abstract description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 7
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 7
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 97
- 125000000217 alkyl group Chemical group 0.000 claims description 87
- -1 iodine, hydrogen Chemical class 0.000 claims description 56
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 37
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 36
- 239000011777 magnesium Substances 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 33
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 26
- 239000000460 chlorine Substances 0.000 claims description 25
- 229920006395 saturated elastomer Polymers 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 125000004122 cyclic group Chemical group 0.000 claims description 20
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 19
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 19
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 229910052727 yttrium Inorganic materials 0.000 claims description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 17
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
- 239000011737 fluorine Substances 0.000 claims description 17
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 16
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 11
- 229910052749 magnesium Inorganic materials 0.000 claims description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- 229910052726 zirconium Inorganic materials 0.000 claims description 11
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 10
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 9
- 229910052732 germanium Inorganic materials 0.000 claims description 9
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 9
- 229910052710 silicon Inorganic materials 0.000 claims description 9
- 239000010703 silicon Substances 0.000 claims description 9
- 229910052718 tin Inorganic materials 0.000 claims description 9
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 7
- 229910052735 hafnium Inorganic materials 0.000 claims description 7
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 229910052719 titanium Inorganic materials 0.000 claims description 7
- 239000010936 titanium Substances 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 230000007704 transition Effects 0.000 claims description 6
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 5
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 5
- 229910052804 chromium Inorganic materials 0.000 claims description 5
- 239000011651 chromium Substances 0.000 claims description 5
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 5
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 5
- 150000002602 lanthanoids Chemical class 0.000 claims description 5
- 229910052750 molybdenum Inorganic materials 0.000 claims description 5
- 239000011733 molybdenum Substances 0.000 claims description 5
- 229910052758 niobium Inorganic materials 0.000 claims description 5
- 239000010955 niobium Substances 0.000 claims description 5
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 5
- 230000000737 periodic effect Effects 0.000 claims description 5
- 229910052715 tantalum Inorganic materials 0.000 claims description 5
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 5
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 5
- 229910052721 tungsten Inorganic materials 0.000 claims description 5
- 239000010937 tungsten Substances 0.000 claims description 5
- 229910052720 vanadium Inorganic materials 0.000 claims description 5
- 125000004407 fluoroaryl group Chemical group 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 claims description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- KSCFJBIXMNOVSH-UHFFFAOYSA-N dyphylline Chemical group O=C1N(C)C(=O)N(C)C2=C1N(CC(O)CO)C=N2 KSCFJBIXMNOVSH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims 1
- 239000003446 ligand Substances 0.000 abstract description 11
- 150000001342 alkaline earth metals Chemical class 0.000 abstract description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 117
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 58
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 51
- 239000000243 solution Substances 0.000 description 44
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 14
- UHOVQNZJYSORNB-MZWXYZOWSA-N deuterated benzene Substances [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical class CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 7
- KJJBSBKRXUVBMX-UHFFFAOYSA-N magnesium;butane Chemical compound [Mg+2].CCC[CH2-].CCC[CH2-] KJJBSBKRXUVBMX-UHFFFAOYSA-N 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000012452 mother liquor Substances 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 230000005068 transpiration Effects 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 4
- 102000015782 Electron Transport Complex III Human genes 0.000 description 4
- 108010024882 Electron Transport Complex III Proteins 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 4
- 125000004126 inden-3-yl group Chemical group [H]C1=C(*)C2=C([H])C([H])=C([H])C([H])=C2C1([H])[H] 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000000962 organic group Chemical group 0.000 description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical group [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 4
- FKTXDTWDCPTPHK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical group FC(F)(F)[C](F)C(F)(F)F FKTXDTWDCPTPHK-UHFFFAOYSA-N 0.000 description 3
- 239000002879 Lewis base Substances 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 229910007926 ZrCl Inorganic materials 0.000 description 3
- 229910007928 ZrCl2 Inorganic materials 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 3
- 125000006343 heptafluoro propyl group Chemical group 0.000 description 3
- 150000007527 lewis bases Chemical class 0.000 description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 230000000707 stereoselective effect Effects 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- PNOKPXONAKHYJS-UHFFFAOYSA-J CC(C)(C)C1=CC(C)=CC=C1O[Zr](Cl)(Cl)OC1=CC=C(C)C=C1C(C)(C)C Chemical compound CC(C)(C)C1=CC(C)=CC=C1O[Zr](Cl)(Cl)OC1=CC=C(C)C=C1C(C)(C)C PNOKPXONAKHYJS-UHFFFAOYSA-J 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 229910052790 beryllium Inorganic materials 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- 229910052700 potassium Inorganic materials 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
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 229910052701 rubidium Inorganic materials 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229910052712 strontium Inorganic materials 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 description 2
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- JKNBOJLBCUPZFW-UHFFFAOYSA-N C(C)[Si](=CC1=CC(=CC1[Mg]C1C=C(C=C1C)C(C)(C)C)C(C)(C)C)CC Chemical compound C(C)[Si](=CC1=CC(=CC1[Mg]C1C=C(C=C1C)C(C)(C)C)C(C)(C)C)CC JKNBOJLBCUPZFW-UHFFFAOYSA-N 0.000 description 1
- HBDBRFCMDXDCER-UHFFFAOYSA-L C(C)[Si](=[Zr](OC1=CC=C(C=C1C(C)(C)C)C)(OC1=CC=C(C=C1C(C)(C)C)C)(C1C=C(C=C1C)C(C)(C)C)C1C=C(C=C1C)C(C)(C)C)CC Chemical compound C(C)[Si](=[Zr](OC1=CC=C(C=C1C(C)(C)C)C)(OC1=CC=C(C=C1C(C)(C)C)C)(C1C=C(C=C1C)C(C)(C)C)C1C=C(C=C1C)C(C)(C)C)CC HBDBRFCMDXDCER-UHFFFAOYSA-L 0.000 description 1
- MUMUTOQCGJZBCH-UHFFFAOYSA-L C1(=CC=CC=C1)C[SiH]=[Zr](OC1=CC=C(C=C1C(C)(C)C)C)(OC1=CC=C(C=C1C(C)(C)C)C)(C1C(=CC2=CC=C3C(=C12)C=CC=C3)C)C1C(=CC2=CC=C3C(=C12)C=CC=C3)C Chemical compound C1(=CC=CC=C1)C[SiH]=[Zr](OC1=CC=C(C=C1C(C)(C)C)C)(OC1=CC=C(C=C1C(C)(C)C)C)(C1C(=CC2=CC=C3C(=C12)C=CC=C3)C)C1C(=CC2=CC=C3C(=C12)C=CC=C3)C MUMUTOQCGJZBCH-UHFFFAOYSA-L 0.000 description 1
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- HGQXHLMWDZFKTN-UHFFFAOYSA-L C[Si](=[Zr](OC1=CC=C(C=C1C(C)(C)C)C)(OC1=CC=C(C=C1C(C)(C)C)C)(C1C(CC2CC=C3C(=C12)C=CC=C3)C)C1C(CC2CC=C3C(=C12)C=CC=C3)C)C Chemical compound C[Si](=[Zr](OC1=CC=C(C=C1C(C)(C)C)C)(OC1=CC=C(C=C1C(C)(C)C)C)(C1C(CC2CC=C3C(=C12)C=CC=C3)C)C1C(CC2CC=C3C(=C12)C=CC=C3)C)C HGQXHLMWDZFKTN-UHFFFAOYSA-L 0.000 description 1
- JRZMBRPXWAYIOG-UHFFFAOYSA-L C[Si](=[Zr](OC1=CC=C(C=C1C(C)(C)C)C)(OC1=CC=C(C=C1C(C)(C)C)C)(C1C=C(C=C1C)C(C)(C)C)C1C=C(C=C1C)C(C)(C)C)C Chemical compound C[Si](=[Zr](OC1=CC=C(C=C1C(C)(C)C)C)(OC1=CC=C(C=C1C(C)(C)C)C)(C1C=C(C=C1C)C(C)(C)C)C1C=C(C=C1C)C(C)(C)C)C JRZMBRPXWAYIOG-UHFFFAOYSA-L 0.000 description 1
- MNDDFKRLDKDGCM-UHFFFAOYSA-L C[Si](=[Zr](OC1=CC=C(C=C1C(C)(C)C)C)(OC1=CC=C(C=C1C(C)(C)C)C)(C1C=C(C=C1C)C(C)(C)CC)C1C=C(C=C1C)C(C)(C)CC)C Chemical compound C[Si](=[Zr](OC1=CC=C(C=C1C(C)(C)C)C)(OC1=CC=C(C=C1C(C)(C)C)C)(C1C=C(C=C1C)C(C)(C)CC)C1C=C(C=C1C)C(C)(C)CC)C MNDDFKRLDKDGCM-UHFFFAOYSA-L 0.000 description 1
- UGAFCTNJGITRKG-UHFFFAOYSA-L C[Si](=[Zr](OC1=CC=C(C=C1C(C)(C)C)C)(OC1=CC=C(C=C1C(C)(C)C)C)(C1C=C(C=C1CC)C(C)(C)C)C1C=C(C=C1CC)C(C)(C)C)C Chemical compound C[Si](=[Zr](OC1=CC=C(C=C1C(C)(C)C)C)(OC1=CC=C(C=C1C(C)(C)C)C)(C1C=C(C=C1CC)C(C)(C)C)C1C=C(C=C1CC)C(C)(C)C)C UGAFCTNJGITRKG-UHFFFAOYSA-L 0.000 description 1
- NMPIJVWQFKDRQY-UHFFFAOYSA-L C[Si](=[Zr](OC1=CC=C(C=C1C(C)(C)C)C)(OC1=CC=C(C=C1C(C)(C)C)C)(C1C=CC2=CC=CC=C12)C1C=CC2=CC=CC=C12)C Chemical compound C[Si](=[Zr](OC1=CC=C(C=C1C(C)(C)C)C)(OC1=CC=C(C=C1C(C)(C)C)C)(C1C=CC2=CC=CC=C12)C1C=CC2=CC=CC=C12)C NMPIJVWQFKDRQY-UHFFFAOYSA-L 0.000 description 1
- VUNDGYPPDBDDLS-UHFFFAOYSA-L C[Si](=[Zr](OC1=CC=C(C=C1C(C)(C)C)C)(OC1=CC=C(C=C1C(C)(C)C)C)(C1C=CC=2CCCCC1=2)C1C=CC=2CCCCC1=2)C Chemical compound C[Si](=[Zr](OC1=CC=C(C=C1C(C)(C)C)C)(OC1=CC=C(C=C1C(C)(C)C)C)(C1C=CC=2CCCCC1=2)C1C=CC=2CCCCC1=2)C VUNDGYPPDBDDLS-UHFFFAOYSA-L 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical group OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- BFWBNXWTEWSMEJ-UHFFFAOYSA-N [He]c(cc1)cc(OCCOc(cc(C)cc2)c2C(CC)=C)c1C(CC)=C Chemical compound [He]c(cc1)cc(OCCOc(cc(C)cc2)c2C(CC)=C)c1C(CC)=C BFWBNXWTEWSMEJ-UHFFFAOYSA-N 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005104 aryl silyl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 230000002146 bilateral effect Effects 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- WYURNTSHIVDZCO-SVYQBANQSA-N deuterated tetrahydrofuran Substances [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- PDPJQWYGJJBYLF-UHFFFAOYSA-J hafnium tetrachloride Chemical compound Cl[Hf](Cl)(Cl)Cl PDPJQWYGJJBYLF-UHFFFAOYSA-J 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene chloride Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000011915 stereoselective alkylation Methods 0.000 description 1
- 238000011916 stereoselective reduction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 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
-
- 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)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19741876.7 | 1997-09-23 | ||
| DE19741876A DE19741876A1 (de) | 1997-09-23 | 1997-09-23 | Verfahren zur selektiven Herstellung racemischer Metallocenkomplexe |
| PCT/EP1998/005918 WO1999015538A1 (de) | 1997-09-23 | 1998-09-17 | Verfahren zur selektiven herstellung racemischer metallocenkomplexe |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2001517673A JP2001517673A (ja) | 2001-10-09 |
| JP2001517673A5 JP2001517673A5 (enExample) | 2009-06-04 |
| JP4360754B2 true JP4360754B2 (ja) | 2009-11-11 |
Family
ID=7843294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000512843A Expired - Lifetime JP4360754B2 (ja) | 1997-09-23 | 1998-09-17 | ラセミメタロセン錯体の選択的製造 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6262286B1 (enExample) |
| EP (1) | EP1017702B1 (enExample) |
| JP (1) | JP4360754B2 (enExample) |
| KR (1) | KR20010024225A (enExample) |
| CN (1) | CN1220694C (enExample) |
| AT (1) | ATE232538T1 (enExample) |
| BR (1) | BR9812084A (enExample) |
| DE (2) | DE19741876A1 (enExample) |
| ES (1) | ES2192791T3 (enExample) |
| WO (1) | WO1999015538A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10030638A1 (de) * | 2000-06-29 | 2002-01-10 | Basell Polyolefine Gmbh | Verfahren zur selektiven Herstellung racemischer Metallocenkomplexe |
| DE10200422A1 (de) * | 2002-01-08 | 2003-07-17 | Basell Polyolefine Gmbh | Verfahren zur Herstellung von Dialkyl-ansa-Metallocenen |
| AR038189A1 (es) | 2002-01-29 | 2005-01-05 | Merck & Co Inc | Proceso para la preparacion de intermediarios de antagonistas de integrina |
| DE10250025A1 (de) * | 2002-10-25 | 2004-05-06 | Basell Polyolefine Gmbh | Verfahren zur Darstellung teilweise hydrierter rac-ansa-Metallocen-Komplexe |
| DE10250062A1 (de) * | 2002-10-25 | 2004-05-06 | Basell Polyolefine Gmbh | Verfahren zur racemoselektiven Darstellung von verbrückten Metallocenkomplexen mit unsubstituierten oder 2-substituierten Indenylliganden |
| AU2003283286A1 (en) * | 2002-10-25 | 2004-05-13 | Basell Polyolefine Gmbh | Racemoselective preparation of isolable ansa-metallocene biphenoxide complexes |
| RU2337104C9 (ru) * | 2002-10-25 | 2009-08-27 | Базелль Полиолефине Гмбх | СПОСОБ ДИАСТЕРЕОСЕЛЕКТИВНОГО СИНТЕЗА РАЦЕМИЧЕСКИХ ДИОРГАНОСИЛИЛБИС(2-МЕТИЛБЕНЗО[е]ИНДЕНИЛ)ЦИРКОНИЕВЫХ СОЕДИНЕНИЙ И РАЦЕМИЧЕСКОЕ СОЕДИНЕНИЕ ПЕРЕХОДНОГО МЕТАЛЛА |
| US7700614B2 (en) | 2005-12-14 | 2010-04-20 | Abbott Laboratories | One pot synthesis of tetrazole derivatives of rapamycin |
| DE102005061326A1 (de) * | 2005-12-20 | 2007-06-21 | Basell Polyolefine Gmbh | Verfahren zur Herstellung von Metallocenen aus recycelten, substituierten Cyclopentadienylderivaten |
| EA015044B1 (ru) * | 2006-02-08 | 2011-04-29 | Сауди Бейсик Индастриз Корпорейшн | Способ олигомеризации этилена |
| KR101278336B1 (ko) | 2007-10-25 | 2013-06-25 | 루머스 노보렌 테크놀로지 게엠베하 | 안사-메탈로센 화합물의 라세모선택적 합성, 안사-메탈로센 화합물, 이를 포함하는 촉매, 그 촉매를 이용한 올레핀 폴리머 제조 공정, 그리고 올레핀 호모- 및 코폴리머 |
| WO2021058742A1 (en) | 2019-09-25 | 2021-04-01 | Borealis Ag | Heterophasic polypropylene copolymers |
| WO2025051400A1 (en) | 2023-09-07 | 2025-03-13 | Borealis Ag | Methods of producing metallocene catalyst components |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE136878T1 (de) | 1990-11-21 | 1996-05-15 | Massachusetts Inst Technology | Neue methoden zur katalytischen reduktion organischer substrate |
| DE19525184A1 (de) | 1995-07-11 | 1997-01-16 | Basf Ag | Verfahren zur Umwandlung der achiralen meso-Form oder des Racemats eines ansa-Metallocenkomplexes oder deren Mischungen in eines seiner Enantiomeren |
-
1997
- 1997-09-23 DE DE19741876A patent/DE19741876A1/de not_active Withdrawn
-
1998
- 1998-09-17 KR KR1020007003040A patent/KR20010024225A/ko not_active Withdrawn
- 1998-09-17 JP JP2000512843A patent/JP4360754B2/ja not_active Expired - Lifetime
- 1998-09-17 US US09/508,970 patent/US6262286B1/en not_active Expired - Lifetime
- 1998-09-17 AT AT98948986T patent/ATE232538T1/de not_active IP Right Cessation
- 1998-09-17 DE DE59807204T patent/DE59807204D1/de not_active Expired - Lifetime
- 1998-09-17 CN CNB988094266A patent/CN1220694C/zh not_active Expired - Lifetime
- 1998-09-17 WO PCT/EP1998/005918 patent/WO1999015538A1/de not_active Ceased
- 1998-09-17 ES ES98948986T patent/ES2192791T3/es not_active Expired - Lifetime
- 1998-09-17 EP EP98948986A patent/EP1017702B1/de not_active Expired - Lifetime
- 1998-09-17 BR BR9812084-0A patent/BR9812084A/pt not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO1999015538A1 (de) | 1999-04-01 |
| EP1017702B1 (de) | 2003-02-12 |
| BR9812084A (pt) | 2000-09-26 |
| CN1220694C (zh) | 2005-09-28 |
| EP1017702A1 (de) | 2000-07-12 |
| KR20010024225A (ko) | 2001-03-26 |
| US6262286B1 (en) | 2001-07-17 |
| ATE232538T1 (de) | 2003-02-15 |
| DE19741876A1 (de) | 1999-03-25 |
| JP2001517673A (ja) | 2001-10-09 |
| CN1271362A (zh) | 2000-10-25 |
| ES2192791T3 (es) | 2003-10-16 |
| DE59807204D1 (de) | 2003-03-20 |
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