CA2098258A1 - Process for the preparation of bridged, chiral metallocene catalysts of the bisindenyl type - Google Patents
Process for the preparation of bridged, chiral metallocene catalysts of the bisindenyl typeInfo
- Publication number
- CA2098258A1 CA2098258A1 CA002098258A CA2098258A CA2098258A1 CA 2098258 A1 CA2098258 A1 CA 2098258A1 CA 002098258 A CA002098258 A CA 002098258A CA 2098258 A CA2098258 A CA 2098258A CA 2098258 A1 CA2098258 A1 CA 2098258A1
- Authority
- CA
- Canada
- Prior art keywords
- solvent
- formula
- suspension
- mixture
- group
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 50
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 239000012968 metallocene catalyst Substances 0.000 title abstract description 3
- 239000002904 solvent Substances 0.000 claims abstract description 67
- 239000000725 suspension Substances 0.000 claims abstract description 38
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000011877 solvent mixture Substances 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 101
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 84
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 69
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 68
- 239000000203 mixture Substances 0.000 claims description 55
- 238000006243 chemical reaction Methods 0.000 claims description 51
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 39
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 32
- 239000003446 ligand Substances 0.000 claims description 24
- 229910052751 metal Inorganic materials 0.000 claims description 20
- 239000002184 metal Substances 0.000 claims description 20
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 18
- 125000004429 atom Chemical group 0.000 claims description 13
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 239000003849 aromatic solvent Substances 0.000 claims description 10
- 125000003106 haloaryl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical group 0.000 claims description 9
- 229910052710 silicon Inorganic materials 0.000 claims description 8
- 239000010703 silicon Substances 0.000 claims description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 239000008096 xylene Substances 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 229910052726 zirconium Inorganic materials 0.000 claims description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052735 hafnium Inorganic materials 0.000 claims description 5
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- 229910052719 titanium Inorganic materials 0.000 claims description 5
- 239000010936 titanium Substances 0.000 claims description 5
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical group Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 claims description 5
- 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 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
- AECTWRMNKTVPEM-UHFFFAOYSA-L [Cl-].[Cl-].CC1=C(C(C2=CC=CC=C12)[Zr+2](C1C=CC2=CC=CC=C12)=[SiH2])C Chemical group [Cl-].[Cl-].CC1=C(C(C2=CC=CC=C12)[Zr+2](C1C=CC2=CC=CC=C12)=[SiH2])C AECTWRMNKTVPEM-UHFFFAOYSA-L 0.000 claims description 4
- CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 claims description 4
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052758 niobium Inorganic materials 0.000 claims description 4
- 239000010955 niobium Substances 0.000 claims description 4
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 4
- 229910000105 potassium hydride Inorganic materials 0.000 claims description 4
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 4
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 4
- 239000012312 sodium hydride Substances 0.000 claims description 4
- 229910052715 tantalum Inorganic materials 0.000 claims description 4
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 4
- 229910052718 tin Inorganic materials 0.000 claims description 4
- 229910052720 vanadium Inorganic materials 0.000 claims description 4
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052732 germanium Inorganic materials 0.000 claims description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 3
- 230000000269 nucleophilic effect Effects 0.000 claims description 3
- 229920000098 polyolefin Polymers 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 2
- 239000001993 wax Substances 0.000 claims description 2
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 claims description 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 4
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- 229910007932 ZrCl4 Inorganic materials 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 125000000217 alkyl group Chemical group 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- -1 polypropylene Polymers 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 239000002585 base Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 238000000605 extraction Methods 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000003480 eluent Substances 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 150000002469 indenes Chemical class 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000005580 one pot reaction Methods 0.000 description 4
- 230000000135 prohibitive effect Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 102000004726 Connectin Human genes 0.000 description 3
- 108010002947 Connectin Proteins 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 244000309464 bull Species 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000003111 delayed effect Effects 0.000 description 3
- 230000005595 deprotonation Effects 0.000 description 3
- 238000010537 deprotonation reaction Methods 0.000 description 3
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical class C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000011097 chromatography purification Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 238000006418 Brown reaction Methods 0.000 description 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 1
- 101100494265 Caenorhabditis elegans best-15 gene Proteins 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- 238000004639 Schlenk technique Methods 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- DXYTUIWIDDBVLU-UHFFFAOYSA-N bis(1h-inden-1-yl)-dimethylsilane Chemical compound C1=CC2=CC=CC=C2C1[Si](C)(C)C1C2=CC=CC=C2C=C1 DXYTUIWIDDBVLU-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- YOBAEOGBNPPUQV-UHFFFAOYSA-N iron;trihydrate Chemical compound O.O.O.[Fe].[Fe] YOBAEOGBNPPUQV-UHFFFAOYSA-N 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 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
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000005599 propionic acid derivatives Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000012721 stereospecific polymerization Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 150000003754 zirconium Chemical class 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
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/0827—Syntheses with formation of a Si-C bond
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2208—Compounds having tin linked only to carbon, hydrogen and/or halogen
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/30—Germanium compounds
-
- 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
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/639—Component covered by group C08F4/62 containing a transition metal-carbon bond
- C08F4/6392—Component covered by group C08F4/62 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
- C08F4/63922—Component covered by group C08F4/62 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not
- C08F4/63927—Component covered by group C08F4/62 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not two cyclopentadienyl rings being mutually bridged
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP92109988.3 | 1992-06-13 | ||
| EP92109988A EP0574597B2 (en) | 1992-06-13 | 1992-06-13 | Process for the preparation of bridged, chiral metallocene catalysts of the bisindenyl type |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2098258A1 true CA2098258A1 (en) | 1993-12-14 |
Family
ID=8209704
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002098258A Abandoned CA2098258A1 (en) | 1992-06-13 | 1993-06-11 | Process for the preparation of bridged, chiral metallocene catalysts of the bisindenyl type |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US5391790A (en:Method) |
| EP (1) | EP0574597B2 (en:Method) |
| JP (1) | JP3419501B2 (en:Method) |
| KR (1) | KR100293042B1 (en:Method) |
| AT (1) | ATE162529T1 (en:Method) |
| AU (1) | AU664896B2 (en:Method) |
| CA (1) | CA2098258A1 (en:Method) |
| DE (1) | DE69224184T2 (en:Method) |
| DK (1) | DK0574597T3 (en:Method) |
| ES (1) | ES2113900T3 (en:Method) |
| GR (1) | GR3026690T3 (en:Method) |
| TW (1) | TW223645B (en:Method) |
| ZA (1) | ZA934148B (en:Method) |
Families Citing this family (102)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5700896A (en) * | 1988-07-30 | 1997-12-23 | Hoechst Aktiengesellschaft | Polymer having long isotactic sequences and randomly-distributed ethylene content obtained by polymerizing propylene in presence of specific catalysts |
| EP0882731A3 (de) * | 1992-08-15 | 2000-05-31 | TARGOR GmbH | Verbrückte Metallocenverbindungen und ihre Verwendung als Olefinpolymerisationskatalysatore |
| JPH06271594A (ja) * | 1993-03-22 | 1994-09-27 | Mitsui Petrochem Ind Ltd | シクロペンタジエニル基含有ケイ素化合物またはシクロペンタジエニル基含有ゲルマニウム化合物の製造方法 |
| DE59409642D1 (de) * | 1993-11-24 | 2001-03-01 | Targor Gmbh | Metallocene, Verfahren zu ihrer Herstellung und ihrer Verwendung als Katalysatoren |
| DE4344689A1 (de) * | 1993-12-27 | 1995-06-29 | Hoechst Ag | Metallocenverbindung |
| DE69631649T2 (de) * | 1995-03-30 | 2004-07-29 | Idemitsu Kosan Co. Ltd. | Übergangsmetallverbindung, polymerisationskatalysator für olefine und verfahren zur herstellung olefinischer polymere |
| US5705578A (en) * | 1995-05-04 | 1998-01-06 | Phillips Petroleum Company | Method for making and using a supported metallocene catalyst system |
| US5631203A (en) * | 1995-05-04 | 1997-05-20 | Phillips Petroleum Company | Metallocene compounds and preparation thereof containing terminal alkynes |
| DE19517851A1 (de) * | 1995-05-16 | 1996-11-21 | Hoechst Ag | Organometallverbindung |
| US5679814A (en) * | 1995-12-11 | 1997-10-21 | Albemarle Corporation | Purification of metallocenes |
| DE59609748D1 (de) * | 1995-12-18 | 2002-11-07 | Basell Polyolefine Gmbh | Verfahren zur Abreicherung von Nebenprodukten in Produktgemischen |
| ID16442A (id) | 1996-01-22 | 1997-10-02 | Dow Chemical Co | Polimer etilena berat molekul ultra rendah |
| AT403919B (de) | 1996-02-02 | 1998-06-25 | Danubia Petrochem Polymere | Verfahren zur herstellung von katalysatorträgern und geträgerter polyolefin-katalysatoren sowie deren verwendung für die herstellung von polyolefinen |
| EP0816371A1 (de) * | 1996-06-28 | 1998-01-07 | PCD-Polymere Gesellschaft m.b.H. | Verfahren zur stereoselektiven Herstellung von chiralen Metallocenen |
| 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 |
| JP3566819B2 (ja) * | 1996-10-04 | 2004-09-15 | 関東化学株式会社 | 新規な有機遷移金属化合物 |
| DK0835886T3 (da) * | 1996-10-09 | 2004-05-17 | Atofina Res | Fremgangsmåde til fremstilling og anvendelse af meso/racemiske (bis(indenyl)ethan)zirconiumdichloridforbindelser |
| US5780660A (en) * | 1996-11-07 | 1998-07-14 | Albemarle Corporation | Zirconocene ismerization process |
| EP0883623B1 (en) * | 1996-11-22 | 2003-03-05 | Boulder Scientific Company | Preparation of chiral titanocenes |
| BR9714409A (pt) | 1996-12-17 | 2000-04-18 | Advanced Elastomer Sistems L P | Composiçãos termoplásticas de olefina |
| ID19264A (id) * | 1996-12-20 | 1998-06-28 | Union Carbide Chem Plastic | Pro-katalisator dan pengolahan untuk membuatnya |
| US6107501A (en) * | 1997-01-30 | 2000-08-22 | Fina Technology, Inc. | Synthesis of metallocenes and enrichment of their rac isomer |
| EP0958313B1 (en) | 1997-02-07 | 2002-09-25 | ExxonMobil Chemical Patents Inc. | Thermoplastic elastomer compositions from branched olefin copolymers |
| CN1246127A (zh) | 1997-02-07 | 2000-03-01 | 埃克森化学专利公司 | 含乙烯基的大分子单体的制备 |
| US6117962A (en) * | 1997-12-10 | 2000-09-12 | Exxon Chemical Patents Inc. | Vinyl-containing stereospecific polypropylene macromers |
| US6184327B1 (en) | 1997-12-10 | 2001-02-06 | Exxon Chemical Patents, Inc. | Elastomeric propylene polymers |
| US6197910B1 (en) | 1997-12-10 | 2001-03-06 | Exxon Chemical Patents, Inc. | Propylene polymers incorporating macromers |
| EP0953582A1 (en) | 1998-04-27 | 1999-11-03 | Fina Research S.A. | Polyolefin production |
| ES2220058T3 (es) | 1998-05-13 | 2004-12-01 | Exxonmobil Chemical Patents Inc. | Homopolimeros de propileno y metodos de fabricarlos. |
| US6306960B1 (en) | 1998-05-13 | 2001-10-23 | Exxonmobil Chemical Patents Inc. | Articles formed from foamable polypropylene polymer |
| US6784269B2 (en) | 1998-05-13 | 2004-08-31 | Exxonmobil Chemical Patents Inc. | Polypropylene compositions methods of making the same |
| US6245868B1 (en) | 1998-05-29 | 2001-06-12 | Univation Technologies | Catalyst delivery method, a catalyst feeder and their use in a polymerization process |
| EP1115761B1 (en) | 1998-08-26 | 2013-09-18 | ExxonMobil Chemical Patents Inc. | Branched polypropylene compositions |
| US5965759A (en) * | 1998-09-23 | 1999-10-12 | Albemarle Corporation | Catalytic process for isomerizing metallocenes |
| DE60036158T2 (de) * | 1999-01-21 | 2008-05-21 | Boulder Scientific Co., Mead | Synthese und isomerisierung von 1,2-bis(indenyl)-ethanen |
| US6174930B1 (en) | 1999-04-16 | 2001-01-16 | Exxon Chemical Patents, Inc. | Foamable polypropylene polymer |
| JP4564612B2 (ja) * | 1999-10-18 | 2010-10-20 | 日本ポリプロ株式会社 | ラセミ体メタロセン化合物の製造方法 |
| US6153777A (en) * | 1999-11-02 | 2000-11-28 | University Of Iowa Research Foundation | Synthesis of ansa-metallocene catalysts |
| US6809168B2 (en) * | 1999-12-10 | 2004-10-26 | Exxonmobil Chemical Patents Inc. | Articles formed from propylene diene copolymers |
| US6977287B2 (en) * | 1999-12-10 | 2005-12-20 | Exxonmobil Chemical Patents Inc. | Propylene diene copolymers |
| CA2393414A1 (en) * | 1999-12-10 | 2001-06-14 | Main Chang | Propylene diene copolymerized polymers |
| WO2001062690A1 (en) | 2000-02-23 | 2001-08-30 | Akzo Nobel N.V. | Process for preparing bisindenylalkanes |
| US7122498B2 (en) * | 2000-06-30 | 2006-10-17 | Exxonmobil Chemical Patents Inc. | Metallocenes and catalyst compositions derived therefrom |
| ATE519789T1 (de) * | 2001-06-12 | 2011-08-15 | Basell Polyolefine Gmbh | Verfahren zur polymerisation von buten-1 |
| CA2447769C (en) * | 2001-06-13 | 2011-07-26 | Energy & Environmental International, L.C. | Bulk polymerization reactors and methods for polymerization |
| EP1444739B1 (en) * | 2001-11-16 | 2009-11-04 | CDT Oxford Limited | Light emitting device and compounds for use therein |
| US6916892B2 (en) * | 2001-12-03 | 2005-07-12 | Fina Technology, Inc. | Method for transitioning between Ziegler-Natta and metallocene catalysts in a bulk loop reactor for the production of polypropylene |
| JP4576126B2 (ja) * | 2002-04-12 | 2010-11-04 | ダウ グローバル テクノロジーズ インコーポレイティド | アザボロリル４族金属錯体、触媒及びオレフィン重合方法 |
| US20030236365A1 (en) * | 2002-06-24 | 2003-12-25 | Fina Technology, Inc. | Polyolefin production with a high performance support for a metallocene catalyst system |
| US20040052690A1 (en) * | 2002-09-12 | 2004-03-18 | Eaton Gerald B. | Polymerization reactant injection system |
| US7589160B2 (en) * | 2002-12-04 | 2009-09-15 | Basell Polyolefine Gmbh | Process for preparing 1-butene polymers |
| US7534848B2 (en) * | 2002-12-04 | 2009-05-19 | Basell Polyolefine Gmbh | 1-butene copolymers and process for preparing them |
| US7195806B2 (en) * | 2003-01-17 | 2007-03-27 | Fina Technology, Inc. | High gloss polyethylene articles |
| WO2004094487A1 (en) | 2003-03-21 | 2004-11-04 | Dow Global Technologies, Inc. | Morphology controlled olefin polymerization process |
| US20050234198A1 (en) * | 2004-04-20 | 2005-10-20 | Fina Technology, Inc. | Heterophasic copolymer and metallocene catalyst system and method of producing the heterophasic copolymer using the metallocene catalyst system |
| US20060052540A1 (en) | 2004-09-09 | 2006-03-09 | Maria Ellul | Thermoplastic vulcanizates |
| US7169864B2 (en) * | 2004-12-01 | 2007-01-30 | Novolen Technology Holdings, C.V. | Metallocene catalysts, their synthesis and their use for the polymerization of olefins |
| US8920891B2 (en) | 2004-12-17 | 2014-12-30 | Dow Global Technologies Llc | Rheology modified relatively high melt strength polyethylene compositions and methods of making pipes, films, sheets, and blow-molded articles |
| US7232869B2 (en) * | 2005-05-17 | 2007-06-19 | Novolen Technology Holdings, C.V. | Catalyst composition for olefin polymerization |
| DE102005061326A1 (de) * | 2005-12-20 | 2007-06-21 | Basell Polyolefine Gmbh | Verfahren zur Herstellung von Metallocenen aus recycelten, substituierten Cyclopentadienylderivaten |
| EP1803747A1 (en) | 2005-12-30 | 2007-07-04 | Borealis Technology Oy | Surface-modified polymerization catalysts for the preparation of low-gel polyolefin films |
| DE102006020486A1 (de) | 2006-04-28 | 2007-10-31 | Basell Polyolefine Gmbh | Geträgerte Metallalkylverbindung und Verfahren zur Polymerisation von Olefinen in deren Gegenwart |
| EP2016127B1 (en) | 2006-05-02 | 2010-03-17 | Dow Global Technologies Inc. | High-density polyethylene compositions, method of making the same, articles made therefrom, and method of making such articles |
| US7456244B2 (en) * | 2006-05-23 | 2008-11-25 | Dow Global Technologies | High-density polyethylene compositions and method of making the same |
| CN101490163A (zh) | 2007-05-02 | 2009-07-22 | 陶氏环球技术公司 | 高密度聚乙烯组合物、其制备方法、由其制得的注塑制品以及该制品的制备方法 |
| US8487033B2 (en) | 2007-05-16 | 2013-07-16 | Exxonmobil Chemical Patents Inc. | Thermoplastic elastomer compositions, methods for making the same, and articles made therefrom |
| US8962762B2 (en) * | 2007-06-13 | 2015-02-24 | Exxonmobil Chemical Patents Inc. | Thermoplastic polymer compositions, methods for making the same, and articles made therefrom |
| US7981517B2 (en) * | 2007-08-28 | 2011-07-19 | Dow Global Technologies Inc. | Bituminous compositions and methods of making and using same |
| BRPI0722163A2 (pt) * | 2007-10-25 | 2014-03-18 | Lummus Novolen Technology Gmbh | Síntese racemoseletiva de compostos de ansa-metaloceno, compostos de ansa-metaloceno, catalisadores compreendendo os mesmos, processo para produzir um polímero de olefina pelo uso dos catalisadores, e homo- e copolímeros de olefina |
| ES2408589T3 (es) | 2008-12-18 | 2013-06-21 | Univation Technologies, Llc | Método para tratamiento de un lecho de siembra para una reacción de polimerización |
| MX2011008053A (es) | 2009-01-30 | 2012-01-12 | Dow Global Technologies Llc | Composiciones de polietileno de alta densidad, metodo para producir las mismas, dispositivos de cierre elaborados de las mismas, y metodo para elaborar dichos dispositivos de cierre. |
| WO2011159400A1 (en) | 2010-06-15 | 2011-12-22 | Exxonmobil Chemical Patents Inc. | Nonwoven fabrics made from polymer blends and methods for making same |
| EP2573091A1 (en) | 2011-09-23 | 2013-03-27 | Lummus Novolen Technology Gmbh | Process for recycling of free ligand from their corresponding metallocene complexes |
| BR112015015373B1 (pt) | 2012-12-28 | 2020-12-15 | Univation Technologies, Llc | Método para integração da produção de aluminoxano na produçâo de um catalisador |
| US9938361B2 (en) | 2013-01-14 | 2018-04-10 | Univation Technologies, Llc | Methods for preparing catalyst systems with increased productivity |
| WO2015030996A1 (en) * | 2013-08-28 | 2015-03-05 | Exxonmobil Chemical Patents Inc. | Racemo selective metallation process |
| US9376518B2 (en) | 2013-08-28 | 2016-06-28 | Exxonmobil Chemical Patents Inc. | Racemo selective metallation process |
| US10351639B2 (en) | 2014-12-12 | 2019-07-16 | Exxonmobil Research And Engineering Company | Organosilica materials for use as adsorbents for oxygenate removal |
| WO2016094843A2 (en) | 2014-12-12 | 2016-06-16 | Exxonmobil Chemical Patents Inc. | Olefin polymerization catalyst system comprising mesoporous organosilica support |
| US10640583B2 (en) | 2015-04-20 | 2020-05-05 | Exxonmobil Chemical Patents, Inc. | Catalyst composition comprising fluorided support and processes for use thereof |
| WO2016172099A1 (en) | 2015-04-20 | 2016-10-27 | Exxonmobil Chemical Patents Inc. | Polyethylene composition |
| BR112017023386B1 (pt) | 2015-05-08 | 2022-04-05 | Exxonmobil Chemical Patents Inc | Processo de polimerização em fase gasosa em modo condensado |
| WO2018063764A1 (en) | 2016-09-27 | 2018-04-05 | Exxonmobil Chemical Patents Inc. | Polymerization process |
| WO2018063767A1 (en) | 2016-09-27 | 2018-04-05 | Exxonmobil Chemical Patents Inc. | Polymerization process |
| WO2018063765A1 (en) | 2016-09-27 | 2018-04-05 | Exxonmobil Chemical Patents Inc. | Polymerization process |
| WO2018118155A1 (en) | 2016-12-20 | 2018-06-28 | Exxonmobil Chemical Patents Inc. | Polymerization process |
| WO2019118073A1 (en) | 2017-12-13 | 2019-06-20 | Exxonmobil Chemical Patents Inc. | Deactivation methods for active components from gas phase polyolefin polymerization process |
| WO2019173030A1 (en) | 2018-03-08 | 2019-09-12 | Exxonmobil Chemical Patents Inc. | Methods of preparing and monitoring a seed bed for polymerization reactor startup |
| US11459408B2 (en) | 2018-05-02 | 2022-10-04 | Exxonmobil Chemical Patents Inc. | Methods for scale-up from a pilot plant to a larger production facility |
| US11447587B2 (en) | 2018-05-02 | 2022-09-20 | Exxonmobil Chemical Patents Inc. | Methods for scale-up from a pilot plant to a larger production facility |
| WO2020014138A1 (en) | 2018-07-09 | 2020-01-16 | Exxonmobil Chemical Patents Inc. | Polyethylene cast films and methods for making the same |
| CN112469556B (zh) | 2018-07-26 | 2023-05-02 | 埃克森美孚化学专利公司 | 多层泡沫膜及其制造方法 |
| WO2020056119A1 (en) | 2018-09-14 | 2020-03-19 | Fina Technology, Inc. | Polyethylene and controlled rheology polypropylene polymer blends and methods of use |
| WO2020102380A1 (en) | 2018-11-13 | 2020-05-22 | Exxonmobil Chemical Patents Inc. | Polyethylene blends and films |
| EP3880739B1 (en) | 2018-11-13 | 2025-03-19 | ExxonMobil Chemical Patents Inc. | Polyethylene films |
| WO2020163079A1 (en) | 2019-02-06 | 2020-08-13 | Exxonmobil Chemical Patents Inc. | Films and backsheets for hygiene articles |
| KR20210127954A (ko) | 2019-02-20 | 2021-10-25 | 피나 테크놀러지, 인코포레이티드 | 휨이 적은 중합체 조성물 |
| KR20220094212A (ko) | 2019-10-30 | 2022-07-05 | 차이나 페트로리움 앤드 케미컬 코포레이션 | 메탈로센 화합물, 및 이의 제조 방법 및 적용 |
| US20230018505A1 (en) | 2019-12-17 | 2023-01-19 | Exxonmobil Chemical Patents Inc. | Films Made of Polyethylene Blends for Improved Sealing Performance and Mechanical Properties |
| US12152135B2 (en) | 2020-03-12 | 2024-11-26 | Exxonmobil Chemical Patents Inc. | Films made of polyethylene blends for improved bending stiffness and high MD tear resistance |
| WO2022232123A1 (en) | 2021-04-26 | 2022-11-03 | Fina Technology, Inc. | Thin single-site catalyzed polymer sheets |
| EP4330294A1 (en) | 2021-04-30 | 2024-03-06 | ExxonMobil Chemical Patents Inc. | Processes for transitioning between different polymerization catalysts in a polymerization reactor |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3742934A1 (de) * | 1987-12-18 | 1989-06-29 | Hoechst Ag | Verfahren zur herstellung einer chiralen, stereorigiden metallocen-verbindung |
| US5017714A (en) * | 1988-03-21 | 1991-05-21 | Exxon Chemical Patents Inc. | Silicon-bridged transition metal compounds |
| IL89525A0 (en) * | 1988-03-21 | 1989-09-10 | Exxon Chemical Patents Inc | Silicon-bridged transition metal compounds |
| DE3844282A1 (de) * | 1988-12-30 | 1990-07-05 | Hoechst Ag | Bisindenyl-derivat und verfahren zu seiner herstellung |
| US5117020A (en) * | 1989-10-30 | 1992-05-26 | Fina Research, S.A. | Process for the preparation of metallocenes |
| EP0426643B1 (en) * | 1989-10-30 | 1995-12-27 | Fina Research S.A. | Process for the preparation of metallocenes |
| EP0485823B1 (de) * | 1990-11-12 | 1995-03-08 | Hoechst Aktiengesellschaft | 2-Substituierte Bisindenylmetallocene, Verfahren zu ihrer Herstellung und ihre Verwendung als Katalysatoren bei der Olefinpolymerisation |
| TW300901B (en:Method) † | 1991-08-26 | 1997-03-21 | Hoechst Ag | |
| NL9101502A (nl) † | 1991-09-06 | 1993-04-01 | Dsm Nv | Werkwijze voor het bereiden van een gebrugde metalloceenverbinding alsmede een katalysatorcomponent en een werkwijze voor de polymerisatie van een olefinen. |
-
1992
- 1992-06-13 DE DE69224184T patent/DE69224184T2/de not_active Expired - Lifetime
- 1992-06-13 AT AT92109988T patent/ATE162529T1/de not_active IP Right Cessation
- 1992-06-13 EP EP92109988A patent/EP0574597B2/en not_active Expired - Lifetime
- 1992-06-13 ES ES92109988T patent/ES2113900T3/es not_active Expired - Lifetime
- 1992-06-13 DK DK92109988T patent/DK0574597T3/da active
-
1993
- 1993-06-01 TW TW082104348A patent/TW223645B/zh active
- 1993-06-11 ZA ZA934148A patent/ZA934148B/xx unknown
- 1993-06-11 CA CA002098258A patent/CA2098258A1/en not_active Abandoned
- 1993-06-11 AU AU40181/93A patent/AU664896B2/en not_active Ceased
- 1993-06-11 KR KR1019930010582A patent/KR100293042B1/ko not_active Expired - Fee Related
- 1993-06-14 JP JP14194993A patent/JP3419501B2/ja not_active Expired - Lifetime
- 1993-06-15 US US08/076,991 patent/US5391790A/en not_active Expired - Lifetime
-
1994
- 1994-11-15 US US08/339,535 patent/US5616747A/en not_active Expired - Lifetime
-
1998
- 1998-04-21 GR GR980400888T patent/GR3026690T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE162529T1 (de) | 1998-02-15 |
| ZA934148B (en) | 1994-01-13 |
| JPH06122692A (ja) | 1994-05-06 |
| EP0574597B2 (en) | 2002-06-26 |
| AU664896B2 (en) | 1995-12-07 |
| GR3026690T3 (en) | 1998-07-31 |
| KR100293042B1 (ko) | 2001-11-22 |
| AU4018193A (en) | 1993-12-16 |
| KR940000472A (ko) | 1994-01-03 |
| JP3419501B2 (ja) | 2003-06-23 |
| US5391790A (en) | 1995-02-21 |
| DE69224184D1 (de) | 1998-02-26 |
| TW223645B (en:Method) | 1994-05-11 |
| DE69224184T2 (de) | 1999-06-02 |
| DK0574597T3 (da) | 1998-09-14 |
| EP0574597B1 (en) | 1998-01-21 |
| ES2113900T3 (es) | 1998-05-16 |
| EP0574597A1 (en) | 1993-12-22 |
| US5616747A (en) | 1997-04-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2098258A1 (en) | Process for the preparation of bridged, chiral metallocene catalysts of the bisindenyl type | |
| US5756608A (en) | Polymerization process using metallocene complexes in the catalyst system | |
| JP2755635B2 (ja) | キラル立体剛性メタロセン化合物の製造方法 | |
| US5621127A (en) | Preparation of bridged half sandwich complexes | |
| CA2057477A1 (en) | Metallocenes having bicyclic cyclopentadiene derivatives as ligands, processes for their preperation and their use as catalysts | |
| JP2813057B2 (ja) | メタロセンの製造法 | |
| JP2002509950A (ja) | 触媒組成物、その製造方法及びオレフィン重合用としての使用法 | |
| US5627246A (en) | Supported metallocene complexes having heterofunctional groups in the cyclopentadienyl system as catalyst systems | |
| CA2144607C (en) | Process for the synthesis of monomethylmetallocenes and dimethylmetallocenes and their solutions specifically for use in the polymerization of olefins | |
| RU2168515C2 (ru) | Способ получения мостикового металлоценового соединения, мостиковый бис-циклопентадиенильный лиганд | |
| US20060025621A1 (en) | Process for the production of monohalide or dihalide metallocene compounds | |
| US5554776A (en) | Racemic metallocene complexes and their preparation | |
| DE4332009A1 (de) | Verfahren zur Herstellung von Organometallfluoriden | |
| JP4454225B2 (ja) | ラセミメタロセン錯体の製造方法 | |
| US5859276A (en) | Organotransition metal compounds | |
| Döring et al. | Preparation of 1, 2, 3, 4-Tetramethylpentafulvene by Hydride Anion Abstraction from Lithium Pentamethylcyclopentadienide Employing Tritylchloride | |
| EP0926150B1 (en) | Production of alkali metal cyclopentadienylides and production of dihalobis(eta-substituted-cyclopentadienyl) zirconium from alkali metal cyclopentadienylides | |
| US3027392A (en) | Organic compounds of fourth-group metals | |
| KR100449473B1 (ko) | 티타노센의 방향족 유도체를 제조하기 위한 방법 | |
| Dorado et al. | Regioselective formation of [2-(η5-cyclopentadienyl)-2-fluorenylpropane]-titanium complexes: precursors, synthesis, structure and reactivity | |
| JP3839176B2 (ja) | アルカリ金属シクロペンタジエニリド類の製造方法およびアルカリ金属シクロペンタジエニリド類を用いるジハロビス（η−置換シクロペンタジエニル）ジルコニウム類の製造方法 | |
| RU2190619C2 (ru) | Способ получения соединений титаноцена | |
| CA2299536A1 (en) | Production of bridged hafnocenes | |
| JP3713405B2 (ja) | 架橋ジルコノセン化合物の製造方法 | |
| Brintzinger | ansa-Metallocene derivatives XVII*. Racemic and meso diastereomers of group IV metallocene derivatives with symmetrically substituted, dimethylsilanediyl-bridged ligand frameworks. Crystal structure of R, S-Me2Si (3-t. Bu-5-MeCsH 2) 2ZrCI2 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |