DE69904521T2 - Verbrückte Zirconocene, deren Herstellung und deren Verwendung als Katalysatorkomponente für die Polymerisation von Olefinen - Google Patents
Verbrückte Zirconocene, deren Herstellung und deren Verwendung als Katalysatorkomponente für die Polymerisation von OlefinenInfo
- Publication number
- DE69904521T2 DE69904521T2 DE69904521T DE69904521T DE69904521T2 DE 69904521 T2 DE69904521 T2 DE 69904521T2 DE 69904521 T DE69904521 T DE 69904521T DE 69904521 T DE69904521 T DE 69904521T DE 69904521 T2 DE69904521 T2 DE 69904521T2
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compound
- indenyl
- group
- bis
- 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 - Fee Related
Links
- 238000006116 polymerization reaction Methods 0.000 title claims description 42
- 239000003054 catalyst Substances 0.000 title claims description 31
- 150000001336 alkenes Chemical class 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 108
- -1 zirconocene compound Chemical class 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 47
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
- 239000003446 ligand Substances 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 37
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 claims description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 150000002009 diols Chemical class 0.000 claims description 31
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 27
- 239000005977 Ethylene Substances 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 230000008569 process Effects 0.000 claims description 23
- 229920006395 saturated elastomer Polymers 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 19
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 17
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 17
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 16
- 239000003960 organic solvent Substances 0.000 claims description 16
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 16
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 15
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 239000002585 base Substances 0.000 claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 12
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- AQZWEFBJYQSQEH-UHFFFAOYSA-N 2-methyloxaluminane Chemical compound C[Al]1CCCCO1 AQZWEFBJYQSQEH-UHFFFAOYSA-N 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 10
- 230000004913 activation Effects 0.000 claims description 10
- 230000003197 catalytic effect Effects 0.000 claims description 10
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 229910006124 SOCl2 Inorganic materials 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000007334 copolymerization reaction Methods 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
- 229910052782 aluminium Inorganic materials 0.000 claims description 7
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 239000002168 alkylating agent Substances 0.000 claims description 5
- 229940100198 alkylating agent Drugs 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 5
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 5
- 239000000178 monomer Substances 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
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 4
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 claims description 4
- 229910010084 LiAlH4 Inorganic materials 0.000 claims description 4
- 229910007161 Si(CH3)3 Inorganic materials 0.000 claims description 4
- 239000001361 adipic acid Substances 0.000 claims description 4
- 235000011037 adipic acid Nutrition 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N hexanedioic acid Natural products OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000012279 sodium borohydride Substances 0.000 claims description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
- 238000001149 thermolysis Methods 0.000 claims description 4
- WBZVXZGPXBXMSC-UHFFFAOYSA-N 2,5,6,6-tetrakis(2-methylpropyl)oxaluminane Chemical compound CC(C)CC1CC[Al](CC(C)C)OC1(CC(C)C)CC(C)C WBZVXZGPXBXMSC-UHFFFAOYSA-N 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000007848 Bronsted acid Substances 0.000 claims description 2
- 239000003125 aqueous solvent Substances 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 claims description 2
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 2
- 238000011282 treatment Methods 0.000 claims description 2
- ZMMRKRFMSDTOLV-UHFFFAOYSA-N cyclopenta-1,3-diene zirconium Chemical class [Zr].C1C=CC=C1.C1C=CC=C1 ZMMRKRFMSDTOLV-UHFFFAOYSA-N 0.000 claims 1
- 238000007257 deesterification reaction Methods 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 83
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 77
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 60
- 239000000243 solution Substances 0.000 description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 59
- 238000005160 1H NMR spectroscopy Methods 0.000 description 50
- 239000011541 reaction mixture Substances 0.000 description 36
- 125000003118 aryl group Chemical group 0.000 description 32
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 31
- 239000000843 powder Substances 0.000 description 29
- 230000015572 biosynthetic process Effects 0.000 description 27
- IDASTKMEQGPVRR-UHFFFAOYSA-N cyclopenta-1,3-diene;zirconium(2+) Chemical class [Zr+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 IDASTKMEQGPVRR-UHFFFAOYSA-N 0.000 description 27
- 238000003786 synthesis reaction Methods 0.000 description 26
- 238000003756 stirring Methods 0.000 description 23
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- 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 16
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 16
- 229920000642 polymer Polymers 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- 239000010410 layer Substances 0.000 description 12
- KXHNSSHBYAVFMS-UHFFFAOYSA-N 2-[2-(1h-inden-2-yl)ethyl]-1h-indene Chemical compound C1=CC=C2CC(CCC=3CC4=CC=CC=C4C=3)=CC2=C1 KXHNSSHBYAVFMS-UHFFFAOYSA-N 0.000 description 11
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 229910007932 ZrCl4 Inorganic materials 0.000 description 10
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 10
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- 229910052726 zirconium Inorganic materials 0.000 description 8
- UMGHCEPAQJUHNV-UHFFFAOYSA-N 2,5-dibenzylhexanedioic acid Chemical compound C=1C=CC=CC=1CC(C(=O)O)CCC(C(O)=O)CC1=CC=CC=C1 UMGHCEPAQJUHNV-UHFFFAOYSA-N 0.000 description 7
- QSZIHBKUAAAXMD-UHFFFAOYSA-N 2-[2-(1,3-dimethyl-1h-inden-2-yl)ethyl]-1,3-dimethyl-1h-indene Chemical compound C1=CC=C2C(C)C(CCC=3C(C4=CC=CC=C4C=3C)C)=C(C)C2=C1 QSZIHBKUAAAXMD-UHFFFAOYSA-N 0.000 description 7
- 238000012512 characterization method Methods 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000012047 saturated solution Substances 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 6
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 238000010561 standard procedure Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- DDHOUKOWIVVYPE-UHFFFAOYSA-N 2,5-dibenzylhexanedioyl dichloride Chemical compound C=1C=CC=CC=1CC(C(=O)Cl)CCC(C(Cl)=O)CC1=CC=CC=C1 DDHOUKOWIVVYPE-UHFFFAOYSA-N 0.000 description 4
- MWZYHHNUNXLIIG-UHFFFAOYSA-N 2-[2-(3-oxo-7-phenyl-1,2-dihydroinden-2-yl)ethyl]-4-phenyl-2,3-dihydroinden-1-one Chemical compound C1C(C(=CC=C2)C=3C=CC=CC=3)=C2C(=O)C1CCC(C1=O)CC2=C1C=CC=C2C1=CC=CC=C1 MWZYHHNUNXLIIG-UHFFFAOYSA-N 0.000 description 4
- 241000349731 Afzelia bipindensis Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 4
- 229940073608 benzyl chloride Drugs 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- HWWXKBXLPYSRNO-UHFFFAOYSA-N diethyl 2,5-bis[(2-phenylphenyl)methyl]hexanedioate Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1CC(C(=O)OCC)CCC(C(=O)OCC)CC1=CC=CC=C1C1=CC=CC=C1 HWWXKBXLPYSRNO-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- IBKNFVLKFMWWCR-UHFFFAOYSA-N 1-methyl-2-[2-(1-methyl-1h-inden-2-yl)ethyl]-1h-indene Chemical compound C1=CC=C2C(C)C(CCC=3C(C4=CC=CC=C4C=3)C)=CC2=C1 IBKNFVLKFMWWCR-UHFFFAOYSA-N 0.000 description 3
- GNXQGFGJDYUKFU-UHFFFAOYSA-N 1-methyl-2-[2-(1-methyl-4-phenyl-1h-inden-2-yl)ethyl]-4-phenyl-1h-indene Chemical compound C=1C(C(=CC=C2)C=3C=CC=CC=3)=C2C(C)C=1CCC(C1C)=CC2=C1C=CC=C2C1=CC=CC=C1 GNXQGFGJDYUKFU-UHFFFAOYSA-N 0.000 description 3
- VBDPXNNRCIXHFT-UHFFFAOYSA-N 2-(1h-inden-2-ylmethyl)-1h-indene Chemical compound C1=CC=C2CC(CC=3CC4=CC=CC=C4C=3)=CC2=C1 VBDPXNNRCIXHFT-UHFFFAOYSA-N 0.000 description 3
- UBKJRUPGXCPDBI-UHFFFAOYSA-N 4-phenyl-2-[2-(4-phenyl-1-propan-2-yl-1h-inden-2-yl)ethyl]-1-propan-2-yl-1h-indene Chemical compound C=1C(C(=CC=C2)C=3C=CC=CC=3)=C2C(C(C)C)C=1CCC(C1C(C)C)=CC2=C1C=CC=C2C1=CC=CC=C1 UBKJRUPGXCPDBI-UHFFFAOYSA-N 0.000 description 3
- CWUFYNOKNSOWEV-UHFFFAOYSA-N 4-phenyl-2-[2-(4-phenyl-1h-inden-2-yl)ethyl]-1h-indene Chemical compound C=1C(C(=CC=C2)C=3C=CC=CC=3)=C2CC=1CCC(C1)=CC2=C1C=CC=C2C1=CC=CC=C1 CWUFYNOKNSOWEV-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 description 3
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- 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 3
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 3
- SEXZHJJUKFXNDY-UHFFFAOYSA-N 1-(bromomethyl)-2-phenylbenzene Chemical compound BrCC1=CC=CC=C1C1=CC=CC=C1 SEXZHJJUKFXNDY-UHFFFAOYSA-N 0.000 description 2
- IDQFTFSTYVWBIZ-UHFFFAOYSA-N 1-ethyl-2-[2-(1-ethyl-1h-inden-2-yl)ethyl]-1h-indene Chemical compound C1=CC=C2C(CC)C(CCC=3C(C4=CC=CC=C4C=3)CC)=CC2=C1 IDQFTFSTYVWBIZ-UHFFFAOYSA-N 0.000 description 2
- QKIXMSFVWTZXCL-UHFFFAOYSA-N 2,5-bis[(2-phenylphenyl)methyl]hexanedioic acid Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1CC(C(=O)O)CCC(C(O)=O)CC1=CC=CC=C1C1=CC=CC=C1 QKIXMSFVWTZXCL-UHFFFAOYSA-N 0.000 description 2
- LXGREMZUKZRAIA-UHFFFAOYSA-N 2,5-bis[(2-phenylphenyl)methyl]hexanedioyl dichloride Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1CC(C(=O)Cl)CCC(C(Cl)=O)CC1=CC=CC=C1C1=CC=CC=C1 LXGREMZUKZRAIA-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 229940077746 antacid containing aluminium compound Drugs 0.000 description 2
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- 150000007857 hydrazones Chemical class 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 239000006060 molten glass Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
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- QMBQEXOLIRBNPN-UHFFFAOYSA-L zirconocene dichloride Chemical compound [Cl-].[Cl-].[Zr+4].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 QMBQEXOLIRBNPN-UHFFFAOYSA-L 0.000 description 2
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- QPFMBZIOSGYJDE-QDNHWIQGSA-N 1,1,2,2-tetrachlorethane-d2 Chemical compound [2H]C(Cl)(Cl)C([2H])(Cl)Cl QPFMBZIOSGYJDE-QDNHWIQGSA-N 0.000 description 1
- YJEYVOCLUMWWAP-UICOGKGYSA-N 1,4-dichloro-1-deuteriohex-1-ene Chemical compound [2H]C(Cl)=CCC(Cl)CC YJEYVOCLUMWWAP-UICOGKGYSA-N 0.000 description 1
- CZICSOZHJCBPNW-UHFFFAOYSA-N 2-benzylhexanedioic acid Chemical compound OC(=O)CCCC(C(O)=O)CC1=CC=CC=C1 CZICSOZHJCBPNW-UHFFFAOYSA-N 0.000 description 1
- VDBSCMJCMSNQQB-UHFFFAOYSA-N 2-methylpropyl-bis(2,4,4-trimethylpentyl)alumane Chemical compound CC(C)(C)CC(C)C[Al](CC(C)C)CC(C)CC(C)(C)C VDBSCMJCMSNQQB-UHFFFAOYSA-N 0.000 description 1
- HEZSFHRGYPJCQY-UHFFFAOYSA-N 2-methylpropyl-bis(2-phenylpropyl)alumane Chemical compound C=1C=CC=CC=1C(C)C[Al](CC(C)C)CC(C)C1=CC=CC=C1 HEZSFHRGYPJCQY-UHFFFAOYSA-N 0.000 description 1
- ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 238000006418 Brown reaction Methods 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
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- 239000004698 Polyethylene Substances 0.000 description 1
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- 238000000944 Soxhlet extraction Methods 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
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- 230000002378 acidificating effect Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- RIAYWWDCGFUPJC-UHFFFAOYSA-N bis(2,4,4-trimethylpentyl)alumane Chemical compound CC(C)(C)CC(C)C[AlH]CC(C)CC(C)(C)C RIAYWWDCGFUPJC-UHFFFAOYSA-N 0.000 description 1
- UXPLEHPMOSDYLZ-UHFFFAOYSA-N bis(2-methylpropyl)-(2,4,4-trimethylpentyl)alumane Chemical compound CC(C)C[Al](CC(C)C)CC(C)CC(C)(C)C UXPLEHPMOSDYLZ-UHFFFAOYSA-N 0.000 description 1
- AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- MKNXBRLZBFVUPV-UHFFFAOYSA-L cyclopenta-1,3-diene;dichlorotitanium Chemical compound Cl[Ti]Cl.C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 MKNXBRLZBFVUPV-UHFFFAOYSA-L 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 238000000151 deposition 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
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- AEUORZZHALJMBM-UHFFFAOYSA-N dibenzyl hexanedioate Chemical compound C=1C=CC=CC=1COC(=O)CCCCC(=O)OCC1=CC=CC=C1 AEUORZZHALJMBM-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- YLCVEZWMZSGEEK-UHFFFAOYSA-N diethyl 2-[(2-phenylphenyl)methyl]hexanedioate Chemical compound CCOC(=O)CCCC(C(=O)OCC)CC1=CC=CC=C1C1=CC=CC=C1 YLCVEZWMZSGEEK-UHFFFAOYSA-N 0.000 description 1
- ISEJRLXHKSHKPM-UHFFFAOYSA-N dimethyl(2-methylpropyl)alumane Chemical compound CC(C)C[Al](C)C ISEJRLXHKSHKPM-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000002270 exclusion chromatography Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000012685 gas phase polymerization Methods 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NCYHQDWNMCYQHR-UHFFFAOYSA-N methyl-bis(2-methylpropyl)alumane Chemical compound CC(C)C[Al](C)CC(C)C NCYHQDWNMCYQHR-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- MCWWHQMTJNSXPX-UHFFFAOYSA-N tribenzylalumane Chemical compound C=1C=CC=CC=1C[Al](CC=1C=CC=CC=1)CC1=CC=CC=C1 MCWWHQMTJNSXPX-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- CFCIWEFTNUMUJY-UHFFFAOYSA-N tris(2-methylphenyl)alumane Chemical compound CC1=CC=CC=C1[Al](C=1C(=CC=CC=1)C)C1=CC=CC=C1C CFCIWEFTNUMUJY-UHFFFAOYSA-N 0.000 description 1
- MLDSMTVYPPIXMZ-UHFFFAOYSA-N tris(4-methylpentyl)alumane Chemical compound CC(C)CCC[Al](CCCC(C)C)CCCC(C)C MLDSMTVYPPIXMZ-UHFFFAOYSA-N 0.000 description 1
- RKPWAHQNLQXPPH-UHFFFAOYSA-N tris(6-methylheptyl)alumane Chemical compound CC(C)CCCCC[Al](CCCCCC(C)C)CCCCCC(C)C RKPWAHQNLQXPPH-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/45—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing nine carbon atoms
- C07C13/465—Indenes; Completely or partially hydrogenated indenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
- C07C69/616—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety polycyclic
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
-
- 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
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/02—Ethene
-
- 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
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/04—Monomers containing three or four carbon atoms
- C08F110/06—Propene
-
- 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
-
- 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
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65912—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an organoaluminium compound
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98200728 | 1998-03-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69904521D1 DE69904521D1 (de) | 2003-01-30 |
| DE69904521T2 true DE69904521T2 (de) | 2003-10-02 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69904521T Expired - Fee Related DE69904521T2 (de) | 1998-03-09 | 1999-03-03 | Verbrückte Zirconocene, deren Herstellung und deren Verwendung als Katalysatorkomponente für die Polymerisation von Olefinen |
Country Status (4)
| Country | Link |
|---|---|
| US (3) | US6232484B1 (enExample) |
| JP (1) | JP2000053691A (enExample) |
| DE (1) | DE69904521T2 (enExample) |
| ES (1) | ES2188047T3 (enExample) |
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| US6342622B1 (en) * | 1999-06-11 | 2002-01-29 | Dsm B.V. | Indenyl compounds for the polymerization of olefins |
| EP1214364B1 (en) * | 1999-09-22 | 2003-07-16 | Basell Polyolefine GmbH | Catalyst system and process for the polymerization of olefins |
| US7060765B2 (en) * | 2001-07-19 | 2006-06-13 | Univation Technologies, Llc | Low comonomer incorporating metallocene catalyst compounds |
| US6559251B1 (en) * | 2002-08-02 | 2003-05-06 | Equistar Chemicals, Lp | Process for making low-density polyolefins |
| US7176158B2 (en) * | 2002-10-25 | 2007-02-13 | Exxonmobil Chemical Patents Inc. | Polymerization catalyst composition |
| CN100457789C (zh) * | 2004-10-27 | 2009-02-04 | 中国石油化工股份有限公司 | 用于烯烃聚合的催化剂组分及其催化剂 |
| EP1764378B1 (en) * | 2005-08-17 | 2009-03-11 | Saudi Basic Industries Corporation | Catalyst composition for polymerization of olefins, polymerization process using the same, and method for its preparation |
| CN104093730A (zh) * | 2011-12-19 | 2014-10-08 | 沙特基础工业公司 | 用于制备茂金属络合物的方法 |
| US9000200B2 (en) * | 2011-12-19 | 2015-04-07 | Saudi Basic Industries Corporation | Process for the preparation of metallocene complexes |
| JP6326202B2 (ja) * | 2013-05-16 | 2018-05-16 | 三井化学株式会社 | オレフィン重合用固体触媒成分およびそれを用いたオレフィン系重合体の製造方法 |
| GB201407000D0 (en) | 2014-04-17 | 2014-06-04 | Isis Innovation | Catalysts |
| CN104370681A (zh) * | 2014-09-29 | 2015-02-25 | 中国科学院上海高等研究院 | 一种乙烯基桥联的二烷基茚化合物的合成方法 |
| WO2016093678A1 (ko) | 2014-12-12 | 2016-06-16 | 주식회사 엘지화학 | 메탈로센 담지 촉매 및 이를 이용하는 폴리올레핀의 제조방법 |
| EP3492532A1 (en) | 2015-01-06 | 2019-06-05 | Scg Chemicals Co. Ltd. | Sio2-layered double hydroxide microspheres and methods of making them |
| US10221259B2 (en) | 2015-01-06 | 2019-03-05 | Scg Chemicals Co., Ltd. | SiO2-layered double hydroxide microspheres and their use as catalyst supports in ethylene polymerisation |
| GB201608384D0 (en) | 2016-05-12 | 2016-06-29 | Scg Chemicals Co Ltd | Unsymmetrical metallocene catalysts and uses thereof |
| CN110650965B (zh) | 2017-04-04 | 2022-10-04 | Sabic环球技术有限责任公司 | 用于烯烃聚合的二烃基-甲硅烷基-桥连-1,3二取代-2-茚基茂金属络合物 |
| US11155659B2 (en) * | 2017-04-04 | 2021-10-26 | Sabic Global Technologies B.V. | Dimethyl-silyl-bridged-1-substituted-2-indenyl metallocene complexes for olefin polymerization |
| US11613593B2 (en) | 2020-02-24 | 2023-03-28 | Exxonmobil Chemical Patents Inc. | Ansa-bis(inden-2-yl) catalysts for producing vinylidene-terminated polyalphaolefins |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3840772A1 (de) | 1988-12-03 | 1990-06-07 | Hoechst Ag | Verfahren zur herstellung einer heterogenen metallocenkatalysatorkomponente |
| DE59104869D1 (de) | 1990-11-12 | 1995-04-13 | Hoechst Ag | 2-Substituierte Bisindenylmetallocene, Verfahren zu ihrer Herstellung und ihre Verwendung als Katalysatoren bei der Olefinpolymerisation. |
| NL9201970A (nl) * | 1992-11-11 | 1994-06-01 | Dsm Nv | Indenylverbindingen en katalysatorcomponenten voor de polymerisatie van olefinen. |
| IT1290856B1 (it) * | 1996-12-19 | 1998-12-14 | Enichem Spa | Metalloceni, loro preparazione ed uso nella polimerizzazione di alfa-olefine |
| ES2198098T3 (es) * | 1998-03-09 | 2004-01-16 | Basell Poliolefine Italia S.P.A. | Procedimiento multietapas para la polimerizacion de olefinas. |
-
1999
- 1999-03-03 ES ES99104222T patent/ES2188047T3/es not_active Expired - Lifetime
- 1999-03-03 DE DE69904521T patent/DE69904521T2/de not_active Expired - Fee Related
- 1999-03-09 JP JP11062448A patent/JP2000053691A/ja not_active Withdrawn
- 1999-03-09 US US09/265,046 patent/US6232484B1/en not_active Expired - Fee Related
-
2001
- 2001-02-28 US US09/795,894 patent/US6306791B2/en not_active Expired - Fee Related
- 2001-10-05 US US09/972,336 patent/US6673880B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20020039962A1 (en) | 2002-04-04 |
| US20010014751A1 (en) | 2001-08-16 |
| US6232484B1 (en) | 2001-05-15 |
| JP2000053691A (ja) | 2000-02-22 |
| US6673880B2 (en) | 2004-01-06 |
| US6306791B2 (en) | 2001-10-23 |
| ES2188047T3 (es) | 2003-06-16 |
| DE69904521D1 (de) | 2003-01-30 |
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