Title:
TRANSITION METAL COMPLEXES FOR PREPARING OLEFIN OLIGOMERS
Document Type and Number:
WIPO Patent Application WO2003027130
Kind Code:
A3
Abstract:
The invention is a method and catalyst for selectively and efficiently producing short chain linear alpha -olefins. The method includes contacting olefinic monomers under oligomerization conditions with the catalyst composition which comprises a composition prepared in situ by reacting a nickel compound selected from the group consisting of halides, hydrides, triflates, acetates, borates, C1, through Cl2 alkyl, C1 through Cl2 alkoxy, C3 through Cl2 cycloalkyl, C3 through Cl2 cycloalkoxy, aryl, thiolates, carbon monoxide, cyanate, olefins including diolefins and cycloolefins, and any other moiety into which a monomer can insert and mixtures thereof, with an amine ligand wherein said ligand is a nitrogen-containing ligand having one or more nitrogen atoms. The method also includes contacting olefinic monomers under oligomerization conditions with the catalyst composition wherein said catalyst has the formula LNi(X')(X)n, wherein n equals O or 1; X and X' are independently selected from the group consisting of halides, hydride, triflate, acetates, borates, Cl through Cl2 alkyl, Cl through Cl2 alkoxy, C3 through Cl2 cycloalkyl, C3 through Cl2 cycloalkoxy, aryl, thiolates, carbon monoxide, cyanate, olefins, and any other moiety into which a monomer can insert; M is selected from the group consisting of nickel, palladium, and platinum and L is a nitrogen-containing bidentate ligand with more than two nitrogen atoms.
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Inventors:
STIBRANY ROBERT T
MATTURRO ROBERT GERARD
ZUSHMA STEPHEN
PATIL ABHIMANYU ONKAR
MATTURRO ROBERT GERARD
ZUSHMA STEPHEN
PATIL ABHIMANYU ONKAR
Application Number:
PCT/US2002/029993
Publication Date:
December 04, 2003
Filing Date:
September 20, 2002
Export Citation:
Assignee:
EXXONMOBIL RES & ENG CO (US)
International Classes:
C07D235/20; B01J31/14; B01J31/18; B01J31/22; C07B61/00; C07C2/32; C07C11/08; C07C11/107; C07D233/20; C07F15/04; B01J23/755; (IPC1-7): C07F15/00; C07F15/04
Domestic Patent References:
| WO2001030865A1 | 2001-05-03 | |||
| WO1998042665A1 | 1998-10-01 | |||
| WO2000068280A1 | 2000-11-16 | |||
| WO1999062968A1 | 1999-12-09 | |||
| WO1992019573A2 | 1992-11-12 |
Foreign References:
| US6245871B1 | 2001-06-12 | |||
| US6037297A | 2000-03-14 | |||
| DE4447068A1 | 1996-07-04 | |||
| EP0039272A2 | 1981-11-04 | |||
| EP0219936A1 | 1987-04-29 | |||
| EP0241760A2 | 1987-10-21 | |||
| US5164457A | 1992-11-17 |
Other References:
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CHALONER P A: "NICKEL, PALLADIUM AND PLATINUM, ANNUAL SURVEY COVERING THE YEAR 1982", JOURNAL OF ORGANOMETALLIC CHEMISTRY, ELSEVIER-SEQUOIA S.A. LAUSANNE, CH, vol. 357, no. 1 - 3, 13 December 1988 (1988-12-13), pages 51 - 246, XP000002442, ISSN: 0022-328X
GARDINER, MICHAEL G. ET AL: "Dicationic chelating N-heterocyclic carbene complexes of palladium: new catalysts for the copolymerization of C2H4 and CO", JOURNAL OF ORGANOMETALLIC CHEMISTRY (1999), 572(2), 239-247, XP004152871
TULLOCH, ARRAN A. D. ET AL: "Chiral 2,6-lutidinyl-biscarbene complexes of palladium", CHEMICAL COMMUNICATIONS (CAMBRIDGE, UNITED KINGDOM) (2001), (14), 1270-1271, XP002229657
BOEHM, VOLKER P. W. ET AL: "Coordination chemistry and mechanisms of metal-catalyzed C-C coupling reactions;Part 12 nonaqueous ionic liquids: superior reaction media for the catalytic Heck-vinylation of chloroarenes", CHEMISTRY--A EUROPEAN JOURNAL (2000), 6(6), 1017-1025, XP002172926
BAKER, MURRAY V. ET AL: "Palladium carbene complexes derived from imidazolium-linked ortho-cyclophanes", JOURNAL OF THE CHEMICAL SOCIETY, DALTON TRANSACTIONS (2001), (2), 111-120, XP002229658
MAGILL, A. M. ET AL: "Palladium(II) complexes containing mono-, bi- and tridentate carbene ligands. Synthesis, characterization and application as catalysts in C-C coupling reactions", JOURNAL OF ORGANOMETALLIC CHEMISTRY (2001), 617-618, 546-560, XP004315079
TULLOCH, ARRAN A. D. ET AL: "Pyridine functionalized N-heterocyclic carbene complexes of palladium", CHEMICAL COMMUNICATIONS (CAMBRIDGE) (2000), (14), 1247-1248, XP002229659
SCHWARZ, JURGEN ET AL: "Polymer-supported carbene complexes of palladium: well-defined, air-stable, recyclable catalysts for the Heck reaction", CHEMISTRY--A EUROPEAN JOURNAL (2000), 6(10), 1773-1780, XP002229660
MCGUINNESS D S ET AL: "Synthesis and reaction chemistry of mixed ligand methylpalladium-carbene complexes", JOURNAL OF ORGANOMETALLIC CHEMISTRY, ELSEVIER-SEQUOIA S.A. LAUSANNE, CH, vol. 565, no. 1-2, 28 August 1998 (1998-08-28), pages 165 - 178, XP004146093, ISSN: 0022-328X
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; YANG, XINLIN ET AL: "Modification of metal complex on hydrogenation of o-chloronitrobenzene over polymer-stabilized platinum colloidal clusters", XP002229909, retrieved from STN Database accession no. 131:144362 CA
CHEN, XIAOHUA ET AL: "Hydrolysis of methionine-containing peptides in binuclear and mononuclear palladium(II) complexes", POLYHEDRON (1998), 17(13-14), 2271-2278, 1998, XP002229906
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; LECOINTE, P. ET AL: "Correlation between the toxicity of platinum drugs to L1210 leukemia cells and their mutagenic properties", XP002229910, retrieved from STN Database accession no. 92:260 CA
BUCKINGHAM J.: "Dictionary of Organometallic Compounds", 1984, CHAPMAN AND HALL LTD, LONDON, XP002229908, 2
PRICE, CLAYTON ET AL: "Macrochelation, cyclometallation and G-quartet formation: N3- and C8-bound PdII complexes of adenine and guanine", CHEMISTRY--A EUROPEAN JOURNAL (2001), 7(6), 1194-1201, XP002229907
CHALONER P A: "NICKEL, PALLADIUM AND PLATINUM, ANNUAL SURVEY COVERING THE YEAR 1982", JOURNAL OF ORGANOMETALLIC CHEMISTRY, ELSEVIER-SEQUOIA S.A. LAUSANNE, CH, vol. 357, no. 1 - 3, 13 December 1988 (1988-12-13), pages 51 - 246, XP000002442, ISSN: 0022-328X
GARDINER, MICHAEL G. ET AL: "Dicationic chelating N-heterocyclic carbene complexes of palladium: new catalysts for the copolymerization of C2H4 and CO", JOURNAL OF ORGANOMETALLIC CHEMISTRY (1999), 572(2), 239-247, XP004152871
TULLOCH, ARRAN A. D. ET AL: "Chiral 2,6-lutidinyl-biscarbene complexes of palladium", CHEMICAL COMMUNICATIONS (CAMBRIDGE, UNITED KINGDOM) (2001), (14), 1270-1271, XP002229657
BOEHM, VOLKER P. W. ET AL: "Coordination chemistry and mechanisms of metal-catalyzed C-C coupling reactions;Part 12 nonaqueous ionic liquids: superior reaction media for the catalytic Heck-vinylation of chloroarenes", CHEMISTRY--A EUROPEAN JOURNAL (2000), 6(6), 1017-1025, XP002172926
BAKER, MURRAY V. ET AL: "Palladium carbene complexes derived from imidazolium-linked ortho-cyclophanes", JOURNAL OF THE CHEMICAL SOCIETY, DALTON TRANSACTIONS (2001), (2), 111-120, XP002229658
MAGILL, A. M. ET AL: "Palladium(II) complexes containing mono-, bi- and tridentate carbene ligands. Synthesis, characterization and application as catalysts in C-C coupling reactions", JOURNAL OF ORGANOMETALLIC CHEMISTRY (2001), 617-618, 546-560, XP004315079
TULLOCH, ARRAN A. D. ET AL: "Pyridine functionalized N-heterocyclic carbene complexes of palladium", CHEMICAL COMMUNICATIONS (CAMBRIDGE) (2000), (14), 1247-1248, XP002229659
SCHWARZ, JURGEN ET AL: "Polymer-supported carbene complexes of palladium: well-defined, air-stable, recyclable catalysts for the Heck reaction", CHEMISTRY--A EUROPEAN JOURNAL (2000), 6(10), 1773-1780, XP002229660
MCGUINNESS D S ET AL: "Synthesis and reaction chemistry of mixed ligand methylpalladium-carbene complexes", JOURNAL OF ORGANOMETALLIC CHEMISTRY, ELSEVIER-SEQUOIA S.A. LAUSANNE, CH, vol. 565, no. 1-2, 28 August 1998 (1998-08-28), pages 165 - 178, XP004146093, ISSN: 0022-328X
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; YANG, XINLIN ET AL: "Modification of metal complex on hydrogenation of o-chloronitrobenzene over polymer-stabilized platinum colloidal clusters", XP002229909, retrieved from STN Database accession no. 131:144362 CA
CHEN, XIAOHUA ET AL: "Hydrolysis of methionine-containing peptides in binuclear and mononuclear palladium(II) complexes", POLYHEDRON (1998), 17(13-14), 2271-2278, 1998, XP002229906
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; LECOINTE, P. ET AL: "Correlation between the toxicity of platinum drugs to L1210 leukemia cells and their mutagenic properties", XP002229910, retrieved from STN Database accession no. 92:260 CA
BUCKINGHAM J.: "Dictionary of Organometallic Compounds", 1984, CHAPMAN AND HALL LTD, LONDON, XP002229908, 2
PRICE, CLAYTON ET AL: "Macrochelation, cyclometallation and G-quartet formation: N3- and C8-bound PdII complexes of adenine and guanine", CHEMISTRY--A EUROPEAN JOURNAL (2001), 7(6), 1194-1201, XP002229907
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