CA2084016A1 - Process for the preparation of substituted indenes and their use as ligand systems for metallocene catalysts - Google Patents
Process for the preparation of substituted indenes and their use as ligand systems for metallocene catalystsInfo
- Publication number
- CA2084016A1 CA2084016A1 CA002084016A CA2084016A CA2084016A1 CA 2084016 A1 CA2084016 A1 CA 2084016A1 CA 002084016 A CA002084016 A CA 002084016A CA 2084016 A CA2084016 A CA 2084016A CA 2084016 A1 CA2084016 A1 CA 2084016A1
- Authority
- CA
- Canada
- Prior art keywords
- preparation
- iva
- metallocene catalysts
- compound
- ligand systems
- 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.)
- Granted
Links
Classifications
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- 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
- 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
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- 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
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
- C07C49/67—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system having two rings, e.g. tetralones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
- C07C49/675—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system having three rings
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- 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 System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/20—Acenaphthenes; Hydrogenated acenaphthenes
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- 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
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- 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
- C08F4/63912—Component covered by group C08F4/62 containing a transition metal-carbon bond in combination with an organoaluminium compound
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- 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
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- 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
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- 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
Abstract
The invention relates to a process for the preparation of a compound of the formula IV or IVa (see formula IV and IVa) in which R1-R5 are preferably hydrogen or alkyl, which comprises reacting a compound I
(see formula I) with a compound II
(see formula II) in which X1 and X2 are preferably halogen, to give the corresponding indanones, which are converted into the compounds IV and IVa by reduction and dehydra-tion. The compounds IV and IVa are important intermediate products for the preparation of chiral metallocene complexes which are suitable catalyst components for olefin polymerization.
(see formula I) with a compound II
(see formula II) in which X1 and X2 are preferably halogen, to give the corresponding indanones, which are converted into the compounds IV and IVa by reduction and dehydra-tion. The compounds IV and IVa are important intermediate products for the preparation of chiral metallocene complexes which are suitable catalyst components for olefin polymerization.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4139594 | 1991-11-30 | ||
DEP4139594.8 | 1991-11-30 |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2084016A1 true CA2084016A1 (en) | 1993-05-31 |
CA2084016C CA2084016C (en) | 2004-06-22 |
Family
ID=6446018
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002084016A Expired - Lifetime CA2084016C (en) | 1991-11-30 | 1992-11-27 | Process for the preparation of substituted indenes and their use as ligand systems for metallocene catalysts |
Country Status (12)
Country | Link |
---|---|
US (4) | US5852142A (en) |
EP (1) | EP0545304B1 (en) |
JP (2) | JP3290218B2 (en) |
KR (1) | KR100322976B1 (en) |
AT (1) | ATE219494T1 (en) |
AU (1) | AU655088B2 (en) |
CA (1) | CA2084016C (en) |
DE (1) | DE59209962D1 (en) |
ES (1) | ES2177523T3 (en) |
RU (1) | RU2103250C1 (en) |
TW (1) | TW309523B (en) |
ZA (1) | ZA929215B (en) |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5585508A (en) * | 1993-11-24 | 1996-12-17 | Hoechst Ag | Metallocenes, process for their preparation and their use as catalysts |
US5679814A (en) * | 1995-12-11 | 1997-10-21 | Albemarle Corporation | Purification of metallocenes |
US5710299A (en) * | 1996-06-27 | 1998-01-20 | Albemarle Corporation | Production of bridged metallocene complexes and intermediates therefor |
US5760262A (en) * | 1996-09-17 | 1998-06-02 | Albemarle Corporation | Enhanced production of bridged hafnocenes |
US5936108A (en) * | 1996-10-17 | 1999-08-10 | Albemarle Corporation | Metallocene synthesis |
US6043403A (en) * | 1995-01-23 | 2000-03-28 | Montell Technology Company Bv | Process for the preparation of cyclopentadienyl compounds and compounds obtained therefrom |
US6087536A (en) * | 1996-08-28 | 2000-07-11 | Basf Aktiengesellschaft | Preparation of indene derivatives |
US6245944B1 (en) | 1996-06-21 | 2001-06-12 | Basf Aktiengesellschaft | Process for producing substituted indanones |
US6558808B1 (en) | 1994-02-21 | 2003-05-06 | Basell Polyolefine Gmbh | Heat-sealable, polyolefinic multilayer film, process for the production thereof, and the use thereof |
US6787618B1 (en) | 1995-12-01 | 2004-09-07 | Basell Polypropylen Gmbh | Metallocene compound and high molecular weight copolymers of propylene and olefins having two or four to thirty-two carbon atoms |
US8293855B2 (en) | 2008-07-23 | 2012-10-23 | Basell Polyolefine Gmbh | Method for transitioning between incompatible olefin polymerization catalyst systems |
US8481658B2 (en) | 2008-12-23 | 2013-07-09 | Basell Polyolefine Gmbh | Method for transitioning between incompatible olefin polymerization catalyst systems |
Families Citing this family (63)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW294669B (en) * | 1992-06-27 | 1997-01-01 | Hoechst Ag | |
EP0584609B1 (en) * | 1992-08-15 | 1999-03-10 | TARGOR GmbH | Process for preparing polyolefins |
JP3357186B2 (en) | 1994-07-14 | 2002-12-16 | 三菱化学株式会社 | Method for producing propylene block copolymer |
IT1273662B (en) * | 1994-07-20 | 1997-07-09 | Spherilene Srl | PROCEDURE FOR THE PREPARATION OF AMORPHOUS POLYMERS OF PROPILINE ' |
EP0693502B1 (en) | 1994-07-22 | 1997-11-05 | Mitsubishi Chemical Corporation | Catalyst component for the polymerization of alpha-olefins and a process for preparing alpha-olefin polymers with use of same |
DE69631649T2 (en) * | 1995-03-30 | 2004-07-29 | Idemitsu Kosan Co. Ltd. | TRANSITION METAL COMPOUND, POLYMERIZATION CATALYST FOR OLEFINS AND METHOD FOR PRODUCING OLEFINIC POLYMERS |
DE19517851A1 (en) * | 1995-05-16 | 1996-11-21 | Hoechst Ag | Organometallic compound |
EP0854876A2 (en) * | 1996-06-27 | 1998-07-29 | Albemarle Corporation | Production of bridged metallocene complexes and intermediates therefor |
DE19729833A1 (en) * | 1997-07-11 | 1999-01-14 | Clariant Gmbh | Polypropylene wax |
DE19757540A1 (en) | 1997-12-23 | 1999-06-24 | Hoechst Ag | Supported olefin polymerization catalyst system, particularly for propylene or ethylene |
US6211300B1 (en) | 1998-04-10 | 2001-04-03 | Chisso Corporation | Propylene-ethylene block copolymer compositions and processes for production thereof |
US6025512A (en) * | 1999-01-06 | 2000-02-15 | Univation Technologies, Llc | Pentafulvene synthesis |
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US20040072975A1 (en) * | 2000-03-17 | 2004-04-15 | Jorg Schottek | Salt-like chemical compound, its preparation and its use in catalyst systems for preparing polyolefins |
US6635733B2 (en) * | 2000-05-23 | 2003-10-21 | Chisso Corporation | Elastomeric polypropylene |
US6846943B2 (en) | 2000-05-23 | 2005-01-25 | Chisso Corporation | Metallocene compound, olefin polymerization catalyst containing the compound, and method for producing an olefin polymer by use of the catalyst |
DE10025412A1 (en) | 2000-05-24 | 2001-11-29 | Basell Polypropylen Gmbh | Chemical products suitable as cocatalysts, processes for their preparation and their use in catalyst systems for the production of polyolefins |
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- 1992-11-27 AU AU29727/92A patent/AU655088B2/en not_active Ceased
- 1992-11-27 ZA ZA929215A patent/ZA929215B/en unknown
- 1992-11-27 EP EP92120289A patent/EP0545304B1/en not_active Expired - Lifetime
- 1992-11-27 JP JP31910192A patent/JP3290218B2/en not_active Expired - Fee Related
- 1992-11-27 ES ES92120289T patent/ES2177523T3/en not_active Expired - Lifetime
- 1992-11-27 AT AT92120289T patent/ATE219494T1/en not_active IP Right Cessation
- 1992-11-27 DE DE59209962T patent/DE59209962D1/en not_active Expired - Lifetime
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- 1995-06-05 US US08/462,587 patent/US5840948A/en not_active Expired - Lifetime
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2001
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Cited By (13)
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US5585508A (en) * | 1993-11-24 | 1996-12-17 | Hoechst Ag | Metallocenes, process for their preparation and their use as catalysts |
US6558808B1 (en) | 1994-02-21 | 2003-05-06 | Basell Polyolefine Gmbh | Heat-sealable, polyolefinic multilayer film, process for the production thereof, and the use thereof |
US6043403A (en) * | 1995-01-23 | 2000-03-28 | Montell Technology Company Bv | Process for the preparation of cyclopentadienyl compounds and compounds obtained therefrom |
US6787618B1 (en) | 1995-12-01 | 2004-09-07 | Basell Polypropylen Gmbh | Metallocene compound and high molecular weight copolymers of propylene and olefins having two or four to thirty-two carbon atoms |
US5679814A (en) * | 1995-12-11 | 1997-10-21 | Albemarle Corporation | Purification of metallocenes |
US6245944B1 (en) | 1996-06-21 | 2001-06-12 | Basf Aktiengesellschaft | Process for producing substituted indanones |
US5861522A (en) * | 1996-06-27 | 1999-01-19 | Albemarle Corporation | Production of bridged metallocene complexes and intermediates therefor |
US5710299A (en) * | 1996-06-27 | 1998-01-20 | Albemarle Corporation | Production of bridged metallocene complexes and intermediates therefor |
US6087536A (en) * | 1996-08-28 | 2000-07-11 | Basf Aktiengesellschaft | Preparation of indene derivatives |
US5760262A (en) * | 1996-09-17 | 1998-06-02 | Albemarle Corporation | Enhanced production of bridged hafnocenes |
US5936108A (en) * | 1996-10-17 | 1999-08-10 | Albemarle Corporation | Metallocene synthesis |
US8293855B2 (en) | 2008-07-23 | 2012-10-23 | Basell Polyolefine Gmbh | Method for transitioning between incompatible olefin polymerization catalyst systems |
US8481658B2 (en) | 2008-12-23 | 2013-07-09 | Basell Polyolefine Gmbh | Method for transitioning between incompatible olefin polymerization catalyst systems |
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US5840948A (en) | 1998-11-24 |
JP3434288B2 (en) | 2003-08-04 |
KR100322976B1 (en) | 2002-05-01 |
EP0545304B1 (en) | 2002-06-19 |
JP2002226405A (en) | 2002-08-14 |
AU655088B2 (en) | 1994-12-01 |
ES2177523T3 (en) | 2002-12-16 |
JP3290218B2 (en) | 2002-06-10 |
ZA929215B (en) | 1993-05-27 |
ATE219494T1 (en) | 2002-07-15 |
AU2972792A (en) | 1993-06-03 |
KR930009968A (en) | 1993-06-21 |
TW309523B (en) | 1997-07-01 |
US6051522A (en) | 2000-04-18 |
US5929264A (en) | 1999-07-27 |
JPH06206890A (en) | 1994-07-26 |
EP0545304A1 (en) | 1993-06-09 |
US5852142A (en) | 1998-12-22 |
CA2084016C (en) | 2004-06-22 |
RU2103250C1 (en) | 1998-01-27 |
DE59209962D1 (en) | 2002-07-25 |
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