CN1243763C - 茂金属化合物的制备方法 - Google Patents
茂金属化合物的制备方法 Download PDFInfo
- Publication number
- CN1243763C CN1243763C CNB99800037XA CN99800037A CN1243763C CN 1243763 C CN1243763 C CN 1243763C CN B99800037X A CNB99800037X A CN B99800037XA CN 99800037 A CN99800037 A CN 99800037A CN 1243763 C CN1243763 C CN 1243763C
- Authority
- CN
- China
- Prior art keywords
- base
- indenyl
- cyclopentadienyl
- ind
- implication
- 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
- 238000000034 method Methods 0.000 title claims abstract description 59
- 150000001875 compounds Chemical class 0.000 title claims description 26
- 239000003446 ligand Substances 0.000 claims abstract description 25
- 229910052732 germanium Inorganic materials 0.000 claims abstract description 10
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 6
- 150000003624 transition metals Chemical class 0.000 claims abstract description 6
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 5
- 229910052747 lanthanoid Inorganic materials 0.000 claims abstract description 3
- 150000002602 lanthanoids Chemical class 0.000 claims abstract description 3
- -1 pentadienyl Chemical group 0.000 claims description 54
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000002585 base Substances 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 21
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 17
- 229910007926 ZrCl Inorganic materials 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- 229910052726 zirconium Inorganic materials 0.000 claims description 14
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 241000534944 Thia Species 0.000 claims description 4
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 4
- 229910052728 basic metal Inorganic materials 0.000 claims description 4
- 150000003818 basic metals Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- 238000013019 agitation Methods 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 229910052735 hafnium Inorganic materials 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- ACAMGZASVKWDNU-UHFFFAOYSA-N CN(C)C.C1=CC=CNC=C1 Chemical compound CN(C)C.C1=CC=CNC=C1 ACAMGZASVKWDNU-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001257 actinium Chemical class 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract description 8
- 125000000217 alkyl group Chemical group 0.000 abstract description 7
- 125000003710 aryl alkyl group Chemical group 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 229930195733 hydrocarbon Natural products 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 2
- 150000001342 alkaline earth metals Chemical class 0.000 abstract description 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
- 150000001255 actinides Chemical group 0.000 abstract 1
- 239000013256 coordination polymer Substances 0.000 abstract 1
- 125000004367 cycloalkylaryl group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 17
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 12
- 229910052782 aluminium Inorganic materials 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- 241000349731 Afzelia bipindensis Species 0.000 description 9
- 239000004411 aluminium Substances 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 230000002194 synthesizing effect Effects 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 238000009834 vaporization Methods 0.000 description 6
- 238000000605 extraction Methods 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 125000002524 organometallic group Chemical group 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 239000002168 alkylating agent Substances 0.000 description 3
- 229940100198 alkylating agent Drugs 0.000 description 3
- 230000002152 alkylating effect Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000007429 general method Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 150000002902 organometallic compounds Chemical class 0.000 description 3
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 3
- IEKPDJDYFASRFB-UHFFFAOYSA-N 1-ethyl-1h-indene Chemical compound C1=CC=C2C(CC)C=CC2=C1 IEKPDJDYFASRFB-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 125000006309 butyl amino group Chemical group 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 150000002469 indenes Chemical class 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical group C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 2
- 238000007039 two-step reaction Methods 0.000 description 2
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 1
- SPFZKMMPGXBEPX-UHFFFAOYSA-N 1-propyl-1h-indene Chemical compound C1=CC=C2C(CCC)C=CC2=C1 SPFZKMMPGXBEPX-UHFFFAOYSA-N 0.000 description 1
- ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- JAKYKQHNJUDFCT-UHFFFAOYSA-N C1=CC=C2C([Zr])C=CC2=C1 Chemical compound C1=CC=C2C([Zr])C=CC2=C1 JAKYKQHNJUDFCT-UHFFFAOYSA-N 0.000 description 1
- OJHXZWHMAFAXEO-UHFFFAOYSA-N CC1=C2C=CC(C2=C(C=C1)C)CC Chemical compound CC1=C2C=CC(C2=C(C=C1)C)CC OJHXZWHMAFAXEO-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- UCIKZESDXASJNG-UHFFFAOYSA-L [Cl-].[Cl-].C1=CC=C2C([Zr+2])C=CC2=C1 Chemical compound [Cl-].[Cl-].C1=CC=C2C([Zr+2])C=CC2=C1 UCIKZESDXASJNG-UHFFFAOYSA-L 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000005815 base catalysis Methods 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 150000001941 cyclopentenes Chemical class 0.000 description 1
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- MYRTYDVEIRVNKP-UHFFFAOYSA-N divinylbenzene Substances C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 238000007172 homogeneous catalysis Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000005574 norbornylene group Chemical group 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical group CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 238000012725 vapour phase polymerization Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/943—Polymerization with metallocene catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98200077 | 1998-01-14 | ||
| EP98200077.0 | 1998-01-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1255925A CN1255925A (zh) | 2000-06-07 |
| CN1243763C true CN1243763C (zh) | 2006-03-01 |
Family
ID=8233295
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB99800037XA Expired - Fee Related CN1243763C (zh) | 1998-01-14 | 1999-01-14 | 茂金属化合物的制备方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6191294B1 (enExample) |
| EP (1) | EP0979232B1 (enExample) |
| JP (1) | JP4208265B2 (enExample) |
| KR (1) | KR20000076111A (enExample) |
| CN (1) | CN1243763C (enExample) |
| CA (1) | CA2283880A1 (enExample) |
| DE (1) | DE69903388T2 (enExample) |
| WO (1) | WO1999036427A1 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20010014072A (ko) | 1998-04-21 | 2001-02-26 | 간디 지오프레이 에이치. | 에틸렌과 알파-올레핀의 공중합체의 제조 방법 |
| WO2000029415A1 (en) | 1998-11-18 | 2000-05-25 | Basell Technology Company B.V. | Methylene bridged metallocenes as olefin-polymerization-catalyst components |
| WO2000075151A1 (en) * | 1999-06-04 | 2000-12-14 | Basell Technology Company B.V. | Process for the preparation of titanium complexes |
| JP2003520869A (ja) | 2000-01-18 | 2003-07-08 | バセル テクノロジー カンパニー ビー．ブイ． | 実質的に非晶質のプロピレンベースのポリマーの製造方法 |
| DE60226427D1 (de) | 2001-04-10 | 2008-06-19 | Basell Polyolefine Gmbh | Verfahren zur herstellung von mono oder bis halogensubstituierten metallozenverbindungen |
| US7074864B2 (en) | 2001-06-12 | 2006-07-11 | Basell Polyolefine Gmbh | Process for the polymerization of 1-butene |
| ATE321061T1 (de) | 2001-06-22 | 2006-04-15 | Basell Polyolefine Gmbh | Metallocene, verwendung in katalysatoren für olefinpolymerisation |
| WO2003008496A1 (en) * | 2001-07-17 | 2003-01-30 | Basell Polyolefine Gmbh | Multistep process for the (co)polymerization of olefins |
| ES2268126T3 (es) | 2001-11-30 | 2007-03-16 | Basell Polyolefine Gmbh | Compuestos de metaloceno y procedimiento para la preparacion de polimeros de propileno. |
| DE10200422A1 (de) * | 2002-01-08 | 2003-07-17 | Basell Polyolefine Gmbh | Verfahren zur Herstellung von Dialkyl-ansa-Metallocenen |
| JP4417719B2 (ja) | 2002-01-08 | 2010-02-17 | バーゼル・ポリオレフィン・ゲーエムベーハー | シリコン橋状メタロセン化合物の製造 |
| JP2005538198A (ja) | 2002-09-06 | 2005-12-15 | バセル ポリオレフィン ジーエムビーエイチ | エチレンの共重合方法 |
| US7176158B2 (en) * | 2002-10-25 | 2007-02-13 | Exxonmobil Chemical Patents Inc. | Polymerization catalyst composition |
| US6693155B1 (en) * | 2003-03-05 | 2004-02-17 | Equistar Chemicals, Lp | Propylene polymerization process |
| DE602004027722D1 (de) | 2003-05-08 | 2010-07-29 | Basell Polyolefine Gmbh | Verfahren zur herstellung von halogenidmetallocenverbindungen |
| DE602004004293T2 (de) | 2003-09-29 | 2007-11-15 | Basell Polyolefine Gmbh | Verfahren zur isomerisierung von metallocenverbindungen |
| CN101245084B (zh) * | 2007-02-14 | 2013-02-20 | 中国石油天然气股份有限公司 | 含膦取代乙烯基茂金属催化剂及其制备方法和应用 |
| EP2197581B1 (en) * | 2007-10-04 | 2016-12-14 | Basell Polyolefine GmbH | Process for the preparation of catalyst paste and products thereof |
| EP2328906A1 (en) | 2008-08-25 | 2011-06-08 | Basell Polyolefine GmbH | Preparation of ansa metallocene compounds |
| BRPI1013814B1 (pt) | 2009-06-16 | 2019-11-05 | Chevron Phillips Chemical Co Lp | método de oligomerização e método para produzir uma polialfaolefina |
| EP2485839A1 (en) * | 2009-10-06 | 2012-08-15 | Chevron Phillips Chemical Company LP | Oligomerization of olefin waxes using metallocene-based catalyst systems |
| KR20140075589A (ko) | 2012-12-11 | 2014-06-19 | 주식회사 엘지화학 | 신규한 리간드 화합물, 이의 제조방법, 전이금속 화합물, 및 이의 제조방법 |
| US9732300B2 (en) | 2015-07-23 | 2017-08-15 | Chevron Phillipa Chemical Company LP | Liquid propylene oligomers and methods of making same |
| JP6038375B1 (ja) * | 2016-06-29 | 2016-12-07 | ポリプラスチックス株式会社 | 触媒の製造方法 |
| KR102073252B1 (ko) * | 2016-12-05 | 2020-02-04 | 주식회사 엘지화학 | 올레핀 공중합체 합성용 촉매 조성물 및 올레핀 공중합체의 제조 방법 |
| KR102765043B1 (ko) * | 2018-05-16 | 2025-02-07 | 주식회사 엘지화학 | 테트라하이드로인덴 유도체로부터 메탈로센 화합물을 제조하는 방법 |
| KR102398899B1 (ko) * | 2019-11-29 | 2022-05-17 | 디엘케미칼 주식회사 | 낮은 점도 알파-올레핀 올리고머 및 이의 제조방법 |
| CN115485311B (zh) | 2020-02-24 | 2024-12-06 | 埃克森美孚化学专利公司 | 用于生产乙烯叉基封端的聚α-烯烃的柄型-双(茚-2-基)催化剂 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA844157B (en) | 1983-06-06 | 1986-01-29 | Exxon Research Engineering Co | Process and catalyst for polyolefin density and molecular weight control |
| US5057475A (en) * | 1989-09-13 | 1991-10-15 | Exxon Chemical Patents Inc. | Mono-Cp heteroatom containing group IVB transition metal complexes with MAO: supported catalyst for olefin polymerization |
| DE69124255T3 (de) * | 1990-06-22 | 2005-10-06 | Exxon Chemical Patents Inc. | Aluminiumfreie monocyclopentadienyl-metallocenkatalysatoren für olefinpolymerisation |
| IT1256259B (it) * | 1992-12-30 | 1995-11-29 | Montecatini Tecnologie Srl | Composti mettallocenici aventi leganti di tipo fluorenilico |
| WO1996019488A1 (en) | 1994-12-21 | 1996-06-27 | Exxon Chemical Patents Inc. | A method of preparing high purity racemic metallocene alkyls and use thereof |
| IL127229A0 (en) | 1997-03-29 | 1999-09-22 | Montell Technology Company Bv | Metallocenes and catalysts for polymerization of olefins |
-
1999
- 1999-01-14 WO PCT/EP1999/000188 patent/WO1999036427A1/en not_active Ceased
- 1999-01-14 JP JP53674499A patent/JP4208265B2/ja not_active Expired - Lifetime
- 1999-01-14 KR KR1019997008199A patent/KR20000076111A/ko not_active Withdrawn
- 1999-01-14 DE DE69903388T patent/DE69903388T2/de not_active Expired - Lifetime
- 1999-01-14 CA CA002283880A patent/CA2283880A1/en not_active Abandoned
- 1999-01-14 CN CNB99800037XA patent/CN1243763C/zh not_active Expired - Fee Related
- 1999-01-14 EP EP99902538A patent/EP0979232B1/en not_active Expired - Lifetime
- 1999-09-13 US US09/381,075 patent/US6191294B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP4208265B2 (ja) | 2009-01-14 |
| WO1999036427A1 (en) | 1999-07-22 |
| CA2283880A1 (en) | 1999-07-22 |
| DE69903388T2 (de) | 2003-06-18 |
| KR20000076111A (ko) | 2000-12-26 |
| EP0979232B1 (en) | 2002-10-09 |
| DE69903388D1 (de) | 2002-11-14 |
| CN1255925A (zh) | 2000-06-07 |
| JP2001516367A (ja) | 2001-09-25 |
| EP0979232A1 (en) | 2000-02-16 |
| US6191294B1 (en) | 2001-02-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1243763C (zh) | 茂金属化合物的制备方法 | |
| CN1075819C (zh) | 金属茂、其制备方法和它作为催化剂的应用 | |
| CN1049899C (zh) | 烯烃的聚合方法 | |
| JP3234876B2 (ja) | ブリッジのあるキラルなメタロセン、その製造方法およびそれの触媒としての用途 | |
| US6451724B1 (en) | Metallocenes and catalysts for olefin-polymerisation | |
| US6268518B1 (en) | Metallocene compounds and their use in catalysts for the polymerization of olefins | |
| US6355819B1 (en) | Substituted metallocene compounds for olefin polymerization catalyst systems, their intermediates and methods for preparing them | |
| CN1374973A (zh) | 用于烯烃聚合的催化剂体系及方法 | |
| CN1052736C (zh) | 无定形丙烯聚合物的制备方法 | |
| CN1260350A (zh) | 双环戊二烯基二烯配合物 | |
| CN1087097A (zh) | 制备乙烯共聚物的方法 | |
| US6365764B1 (en) | Bridged bis-fluorenyl metallocenes process for the preparation thereof and use thereof in catalysts for the polymerization of olefins | |
| CN1181386A (zh) | 金属茂 | |
| CN1293677A (zh) | 桥连金属茂的制备和在催化体系中的应用 | |
| JP3986441B2 (ja) | モノハライドまたはジハライドメタロセン化合物の製造方法 | |
| US7002031B2 (en) | Preparation of silicon-bridged metallocene compounds | |
| EP1102778B1 (en) | Process for the preparation of titanium complexes | |
| CN1217891C (zh) | 亚甲基桥接双环戊二烯基化合物的制备方法 | |
| CN100349910C (zh) | 用于制备金属茂的含有至少一个氟硅氧烷取代基的配体 | |
| EP1620448B1 (en) | Process for the production of halide metallocene compounds | |
| CN100448883C (zh) | 金属茂化合物的异构化方法 | |
| CN1345325A (zh) | 制备钛络合物的方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C17 | Cessation of patent right | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20060301 Termination date: 20100222 |