Exactly Three Carbons Bonded Directly To The Phosphorus (e.g., Triphenylphosphines, Etc.) Patents (Class 556/21)
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Patent number: 5015747Abstract: The invention relates to organometallic compounds which are stabilized intramolecularly and have a cyclic or bicyclic structure and to the use thereof for the preparation of thin films and epitaxial layers by gas phase deposition.Type: GrantFiled: April 7, 1989Date of Patent: May 14, 1991Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Martin Hostalek, Ludwig Pohl, Dietrich Erdmann, Herbert Schumann, Uwe Hartmann, Meino Heyen, Holger Jurgensen
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Patent number: 5012002Abstract: 2,2'-Bis[di-(m-tolyl)phosphino]-1,1'-binaphthyl represented by formula (I) is disclosed. ##STR1## The compound of formula (I) is capable of forming a complex with a metal, e.g., ruthenium, rhodium, and palladium, which is extremely important and industrially excellent as a catalyst for various asymmetric synthesis reactions.Type: GrantFiled: June 15, 1990Date of Patent: April 30, 1991Assignee: Takasago International CorporationInventors: Hidenori Kumobayashi, Takanao Taketomi
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Patent number: 5004823Abstract: The hydroformylation of olefins with rhodium complex catalysts is described. The catalysts employed comprise a rhodium complex with at least one bidentate ligand having a specified structure, ##STR1## Hydroformylation reactions at relatively low temperatures and pressure and yet with high rates of reaction and high selectivity to aldehyde product are obtained by the practice of the present invention.Type: GrantFiled: February 23, 1990Date of Patent: April 2, 1991Assignee: Eastman Kodak CompanyInventors: Thomas J. Devon, Gerald W. Phillips, Thomas A. Puckette, Jerome L. Stavinoha, Jeffrey J. Vanderbilt
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Patent number: 4994590Abstract: A ruthenium-phosphine complex represented by formula (I)[RuX.sub.l (L).sub.m (R-BINAP)]Y.sub.n (I)wherein R-BINAP represents a tertiary phosphine represented by formula (II): ##STR1## wherein R represents a hydrogen atom or a methyl group; X represents a halogen atom; L represents substituted or unsubstituted benzene or acetonitrile; Y represents a halogen atom, CLO.sub.4, PF.sub.6, BPh.sub.4 (wherein Ph represents a phenyl group) or BF.sub.4 ; when L is substituted or unsubstituted benzene, l represents 1, m represents 1, and n represents 1; and whe L is acetonitrile, when l is 1, then m represents 2, and n represents 1, and when l is 0, the m represents 4, and n represent 2. The complex exhibits excellent catalytic activity in asymmetric reactions to provide a product of high optical purity. The complex can be produced at low cost.Type: GrantFiled: October 24, 1989Date of Patent: February 19, 1991Assignee: Takasago International CorporationInventors: Hidemasa Takaya, Kazushi Mashima, Hidenori Kumobayashi, Noboru Sayo
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Patent number: 4987242Abstract: A coordination compound useful as a hydrogenation catalyst, having the formula: ##STR1## wherein Ph is phenyl; R is hydrogen or C.sub.1 -C.sub.4 alkyl; and X is chloro, bromo or iodo. This compound is particularly useful as a homogeneous hydrogenation catalyst in the production of alpha-6-deoxytetracyclines, particularly the antibiotic doxycycline. The desired alpha-6-deoxy product is produced in high yields and stereospecificities, the process requiring the use of minimal quantities of rhodium metal in the hydrogenation catalyst per mole of the 6-methylenetetracycline hydrogenated.Type: GrantFiled: November 29, 1989Date of Patent: January 22, 1991Inventors: Jagmohan Khanna, Kiran Bala, Inder P. S. Grover
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Patent number: 4947003Abstract: A process for the hydroformylation of alkenes and other olefinically unsaturated reactants by reaction with carbon monoxide and hydrogen in the presence of a heterogeneous catalyst comprising a solid surface having immobilized thereon a solution of one or more rhodium complexes which is essentially immiscible with the organic reactant. Catalyst is subsequently recovered from the resulting hydroformylation product by one or more solid-liquid separation techniques.Type: GrantFiled: November 28, 1988Date of Patent: August 7, 1990Assignee: Virginia Tech Intellectual Properties, Inc.Inventors: Mark E. Davis, Juan P. Arhancet, Brian E. Hanson
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Patent number: 4945174Abstract: New palladium-based complexes permit the complexing of chlorinated aromatic derivatives. These complexes make it possible to perform hydrogenolysis, hydrocarbonylation and alkoxycarbonylation reaction on chlorinated compounds.Type: GrantFiled: July 20, 1989Date of Patent: July 31, 1990Assignee: Rhone Poulenc ChimieInventors: Marc Huser, John Osborn
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Patent number: 4911865Abstract: The present invention refers to complexes prepared by reacting rhodium trinitrate with a suitable hydrazine and a suitable tertiary phosphine, more specifically to the compounds di(.mu.-hydrazine-N.sup.1 :N.sup.2)-bis[bis(triphenylphosphine)rhodium (I)]dinitrate and .mu.-3-carbopentazane-N.sup.1, N.sup.4 :N.sup.2, N.sup.5 -bis[bis(triphenylphosphine)rhodium (I)]dinitrate, which are homogenous hydrogenation catalysts and their application in the hydrogenation of the exocyclic methylene group of acid addition salts of 6-demethyl-6-deoxy-6-methylene-5-hydroxytetracycline (methacycline) to prepare .alpha.-6-deoxy-5-hydroxy-tetracycline (doxycycline).Type: GrantFiled: March 13, 1989Date of Patent: March 27, 1990Assignee: Plurichemie AnstaltInventors: William Heggie, Philip R. Page, Ivan Villax, Indira Ghatak, Michael Hursthouse
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Patent number: 4904808Abstract: A novel ligand for use in hydroformylation reactions wherein at least one olefin having from 2 to 20 carbon atoms is contacted in a reaction zone at a temperature of from about 20.degree. C. to about 250.degree. C. and a pressure of from about 50 psig to about 800 psig with hydrogen, carbon monoxide, and a catalyst containing rhodium, the ligand having the formula ##STR1## wherein: n is 1-4;each R is independently selected from hydrogen, alkyl, alkoxy, aryloxy, aryl, aralkyl, alkaryl, alkoxyalkyl, cycloaliphatic, halogen, alkanoyl, alkanoyloxy, alkoxycarbonyl, carboxyl or cyano;each R.sub.1 and R.sub.2 is independently selected from alkyl, aryl, aralkyl, alkaryl or cycloaliphatic;each R.sub.3 and R.sub.4 is independently selected from hydrogen and the R.sub.1 substituents; andeach Y is independently selected from the elements N, P, As, Sb and Bi.Type: GrantFiled: March 13, 1989Date of Patent: February 27, 1990Assignee: Eastman Kodak CompanyInventors: Thomas J. Devon, Gerald W. Phillips, Thomas A. Puckette, Jerome L. Stavinoha, Jeffrey J. Vanderbilt
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Patent number: 4861918Abstract: A process for improving the catalytic activity of a partially deactivated solubilized rhodium - tertiary organophosphine complex hydroformylation catalyst.Type: GrantFiled: August 12, 1988Date of Patent: August 29, 1989Assignee: Union Carbide CorporationInventors: David J. Miller, David R. Bryant, Ernst Billig, Bernard L. Shaw
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Patent number: 4861890Abstract: A process for producing chiral enamines by isomerizing a beta, gamma unsaturated amine with a rhodium-diphosphine complex with the addition of an achiral triarylphosphine and, if desired, hydrolyzing the compound of the enamine I obtained to the corresponding aldehyde.Type: GrantFiled: August 10, 1987Date of Patent: August 29, 1989Assignee: Hoffmann-La Roche Inc.Inventors: Bernd Heiser, Hansjorg Stoller
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Patent number: 4857235Abstract: The present invention refers to complexes prepared by reacting rhodium trinitrate with a suitable hydrazine and a suitable tertiary phosphine, more specifically to the compounds di(.mu.-hydrazine-N.sup.1 :N.sup.2)-bis[bis(triphenylphosphine)rhodium (I)]dinitrate and .mu.-3-carbopentazane-N.sup.1,N.sup.4 :N.sup.2,N.sup.5 -bis[bis(triphenylphosphine)rhodium (I)]dinitrate, which are homogeneous hydrogenation catalysts and their application in the hydrogenation of the exocyclic methylene group of acid addition salts of 6-demethyl-6-deoxy-6-methylene-5-hydroxytetracycline (methacycline) to prepare .alpha.-6-deoxy-5-hydroxy-tetracycline (doxycycline).Type: GrantFiled: May 15, 1987Date of Patent: August 15, 1989Assignee: Plurichemie AnstaltInventors: William Heggie, Philip R. Page, Ivan Villax, Indira Ghatak, Michael Hursthouse
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Patent number: 4845306Abstract: Disclosed is a process for recovering or concentrating active catalyst materials from a substantially homogeneous system comprising:(a) active catalyst materials which comprise(i) triorganophosphine-rhodium complexes, and(ii) free triorganophosphine;(b) oxidized triorganophosphine residues,(c) iron carboxylate salts,(d) pump oils, and(e) aldehydes and aldol condensation products thereof;said processing comprising:(1) admixing a portion of said homogeneous system with about 1 up to 100 volumes (relative to the volume of said portion) of at least one nonpolar hydrophobic hydrocarbon diluent selected from the group consisting of saturated or unsaturated aliphatic hydrocarbon having in the range of 3 up to 20 carbon atoms and aromatic or hydrocarbyl-substituted aromatic hydrocarbons having in the range of 6 up to 22 carbon atoms to produce a diluted homogeneous system,(2) contacting said diluted homogeneous system with 0.Type: GrantFiled: July 12, 1988Date of Patent: July 4, 1989Assignee: Eastman Kodak CompanyInventor: Thomas A. Puckette
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Patent number: 4831170Abstract: Novel bis[bis(diphenylphosphino)hydrocarbon] and bis[diphenylphosphino-diphenylarsino)hydrocarbon]-group VIII metal compounds of the formula 1 of the formula sheet, whereinD.sub.1 =D.sub.2 =phosphorus or D.sub.1 =phosphorus and D.sub.2 =arsenic;A=(CH.sub.2).sub.2 or cis-CH=CH;X.sub.1 =X.sub.2 (both if present)=halo or nitrato or X.sub.1 +X=peroxo;Y (if present)=halide, nitrate, perchlorate, triflate or tetrahaloferrate (III) p1 n=0, 1 or 2;M=Fe(II) Fe(III), Co(II) Rh(I) , Rh(III), Ir(I), Ir(III), Ni(II) or Pd(II),showing a tumor cell growth-inhibiting activity, novel pharmaceutical compositions containing said compounds and a method for treating tumor cells, sensitive to said compounds.Type: GrantFiled: October 24, 1986Date of Patent: May 16, 1989Assignee: Nedenlandse Centrale Organisatie voor Toegepart-Natuurwetenschappelijk OnderzoekInventors: Klaas Timmer, Harmen A. Meinema, E. Schurig
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Patent number: 4824977Abstract: A hydroformylation process including contacting hydroformylation stock in a reaction zone at a temperature of from about 20.degree. C. to about 250.degree. C. and a pressure of from about 15 psig to about 800 psig with hydrogen and carbon monoxide wherein the catalyst comprises rhodium in chemical complex with one or more ligands of the formulae ##STR1## wherein: Z, when present, represents the atoms necessary to form with adjacent carbons on the benzene nucleus a fused divalent ring structure having up to about 20 ring carbons;each ring is either unsubstituted or one or more of the hydrogens thereof is replaced with a substituent R selected independently from alkyl, alkoxy, aryloxy, aryl, aralkyl, alkaryl, alkoxyalkyl, cycloaliphatic, halogen, alkanoyl, alkanoyloxy, alkoxycarbonyl, carboxyl or cyano;each R.sub.1 and R.sub.Type: GrantFiled: March 11, 1988Date of Patent: April 25, 1989Assignee: Eastman Kodak CompanyInventors: Thomas J. Devon, Gerald W. Phillips, Thomas A. Puckette, Jerome L. Stavinoha, Jr., Jeffrey J. Vanderbilt
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Patent number: 4822925Abstract: Novel vicinal dioxyalkylene organometalates comprising a cation having a hydrocarbyl-containing substituent are disclosed. The vicinal dioxyalkylene organometalates can be reacted with water to yield alkylene glycols.Type: GrantFiled: February 6, 1987Date of Patent: April 18, 1989Assignee: Union Carbide CorporationInventors: John R. Briggs, John H. Robson
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Patent number: 4822915Abstract: An oligomerization or cooligomerization process comprising passing ethylene or a mixture of ethylene and propylene in contact with a catalyst, in the liquid phase.Type: GrantFiled: May 26, 1987Date of Patent: April 18, 1989Assignee: Union Carbide CorporationInventor: Rex E. Murray
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Patent number: 4766227Abstract: A ruthenium-phosphine complex represented by formula (I): ##STR1## wherein R represents a hydrogen atom, a methyl group, or a methoxy group; and X represents ClO.sub.4, BF.sub.4, or PF.sub.6. The ruthenium-phosphine complex is inexpensive and exhibits excellent performance as a catalyst for various organic syntheses, particularly for asymmetric hydrogenation.Type: GrantFiled: December 9, 1987Date of Patent: August 23, 1988Assignee: Takasago International CorporationInventors: Noboru Sayo, Takanao Taketomi, Hidenori Kumobayashi, Susumu Akutagawa
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Patent number: 4743466Abstract: For use in magnetic recording tapes and for other purposes, iron and iron alloy materials are passivated and protected against oxidative corrosion by treatment with a solution of a non-hygroscopic salt of bis(triphenylphosphoranylidene) ammonium cation with an anion such as nitrate or chromate.Type: GrantFiled: June 5, 1987Date of Patent: May 10, 1988Assignee: Eastman Kodak CompanyInventors: Henry J. Gysling, Joseph S. Yudelson
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Patent number: 4739084Abstract: A ruthenium-phosphine complex having a 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl or its derivative as a ligand and carboxyl groups bonded to the ruthenium atom thereof is disclosed. The complex is inexpensive and exhibits excellent performances as a catalyst for various organic syntheses, and particularly for asymmetric hydrogenation.Type: GrantFiled: April 15, 1987Date of Patent: April 19, 1988Assignee: Takasago Perfumery Co., Ltd.Inventors: Hidemasa Takaya, Tetsuo Ohta, Ryoji Noyori, Nobuo Yamada, Toshiyuki Takezawa, Noboru Sayo, Takanao Taketomi, Hidenori Kumobayashi, Susumu Akutagawa
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Patent number: 4739085Abstract: A ruthenium-phosphine complex represented by formula (I):[RuH.sub.l (R-BINAP).sub.m ]X.sub.n' (I)wherein R-BINAP is a tertiary phosphine represented by formula (II): ##STR1## R is a hydrogen atom or a methyl group; X is a ClO.sub.4, BF.sub.4, or PF.sub.6 ; and when l is 0, then m is 1 and n' is 2, and when l is 1, then m is 2 and n' is 1, is disclosed. The complex is inexpensive and exhibits excellent performances as a catalyst for various organic syntheses, and particularly for asymmetric hydrogenation.Type: GrantFiled: June 15, 1987Date of Patent: April 19, 1988Assignee: Takasago Perfumery Co., Ltd.Inventors: Hidemasa Takaya, Tetsuo Ohta, Ryoli Noyori, Noboru Sayo, Hidenori Kumobayashi, Susumu Akutagawa
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Patent number: 4730065Abstract: This disclosure describes novel 15-deoxy-16-hydroxy-16-substituted prostanoic acids and congeners thereof having utility as bronchodilators as hypotensive agents, and as agents for the control of excessive gastric secretion.Type: GrantFiled: July 24, 1987Date of Patent: March 8, 1988Assignee: American Cyanamid CompanyInventors: Middleton B. Floyd, Jr., Martin J. Weiss, Charles V. Grudzinskas, Sow-Mei L. Chen
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Patent number: 4668809Abstract: Compositions of matter are disclosed which are highly useful in hydroformylation processes. The compositions are non-charged, non-chelated bis- and tris-(alkyl diaryl phosphine) rhodium carbonyl hydrides. The substituents of the alkyl group includes heteroorganic radicals containing ether, ester, keto and hydroxy oxygen, phosphine oxide and phosphorus ester phosphorus, amine, amide, amine oxide and heterocyclic nitrogen groups.These compositions are highly stable and selective catalysts for the hydroformylation of olefins under certain conditions. The disclosed catalyst systems contain a large excess of phosphine ligand and employ alpha-olefin plus synthesis gas reactant mixtures having a high H.sub.2 /CO ratio at relatively low pressures. They produce moslty aldehydes derived from terminal attack on the alpha-olefin reactant.Type: GrantFiled: June 6, 1985Date of Patent: May 26, 1987Assignee: Exxon Research and EngineeringInventors: Alexis A. Oswald, Torris G. Jermasen, Andrew A. Westner, I-Der Huang
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Patent number: 4667045Abstract: Novel vicinal dioxyalkylene organometalates comprising a cation having a hydrocarbyl-containing substituent are disclosed. The vicinal dioxyalkylene organometalates can be reacted with water to yield alkylene glycols.Type: GrantFiled: March 28, 1984Date of Patent: May 19, 1987Assignee: Union Carbide CorporationInventors: John R. Briggs, John H. Robson
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Patent number: 4656299Abstract: A complex of an electron-attracting group-substituted .eta..sup.5 -cyclopentadienylcobalt with a polyene or an acetylene for use as a catalyst, for example, for the synthesis of a substituted pyridine from an alkyne and a nitrile.Type: GrantFiled: January 13, 1986Date of Patent: April 7, 1987Assignees: Denki Kagaku Kogyo Kabushiki Kaisha, Rikagaku KenkyusyoInventors: Chiyuki Fujii, Seiichi Watanabe
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Patent number: 4620021Abstract: Olefins such as ethylene can be polymerized with a catalyst which comprises nickel compounds obtained by reacting a nickel-(O) compound or a nickel compound which may be converted in situ into a nickel-(O) compound with an adduct or a mixture of a quinoid compound and a tertiary phosphine and with a compound corresponding to the following general formula: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 independently represent C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.20 alkenyl, C.sub.6 -C.sub.12 aryl or C.sub.3 -C.sub.8 cycloalkyl optionally substituted by halogen, hydroxy, C.sub.1 -C.sub.20 alkoxy, nitro or C.sub.6 -C.sub.12 aryloxy; also C.sub.6 -C.sub.12 aryl-C.sub.1 -C.sub.20 alkyl, C.sub.6 -C.sub.12 aryl-C.sub.2 -C.sub.20 alkenyl, C.sub.1 -C.sub.20 alkyl-C.sub.6 -C.sub.12 aryl, C.sub.1 -C.sub.20 alkyl-C.sub.3 -C.sub.8 cycloalkyl and C.sub.6 -C.sub.12 aryl-C.sub.3 -C.sub.8 cycloalkyl, di-C.sub.1 -C.sub.4 alkylamino, optionally substituted phenoxy or alkoxy; R.sup.4, R.sup.5 and R.sup.Type: GrantFiled: September 25, 1984Date of Patent: October 28, 1986Assignee: Bayer AktiengesellschaftInventors: Karl-Heinz A. O. Starzewski, Josef Witte, Herbert Bartl
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Patent number: 4578522Abstract: This invention relates to a method of synthesis of certain substituted carboxylic acids useful in lowering serum triglyceride and total cholesterol levels in mammals (including man) represented by the general formula I:Ar.sup.1 --Ar.sup.2 (I)whereinAr.sup.1 is selected from ##STR1## Ar.sup.2 is selected from ##STR2## and R is selected from C.sub.1-5 alkyl, halogen, perhalo-C.sub.1-4 alkyl, C.sub.1-4 alkoxy, phenyl, C.sub.1-4 acyl, C.sub.1-6 alkoxycarbonyl, amino or hydroxy.Type: GrantFiled: September 14, 1984Date of Patent: March 25, 1986Inventor: John F. Eaddy, III
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Patent number: 4556720Abstract: Coordination compounds of rhodium are solid salts having donor ligands of [(aryl).sub.3 P].sub.3 Rh.sup.+ and a non-coordinated counterion derived from a fluorochemical acid, the salts having the formula:[(aryl).sub.3 P].sub.3 Rh.sup.+ (counterion).sup.-.The salts are prepared by reacting [(aryl).sub.3 P].sub.4 RhH, which is an uncharged rhodium hydride, with a fluorochemical acid selected form acids having the formulae:HC(R)(SO.sub.2 R.sub.f).sub.2, R.sub.f 'SO.sub.3 H, and HN(SO.sub.2 R.sub.f).sub.2wherein R.sub.f and R.sub.f ' are perfluoroalkyl groups and R is lower alkyl substituted or unsubstituted phenyl, hydrogen, Cl, SO.sub.2 R.sub.f or R.sub.f. Carbonylation of the [(aryl).sub.3 P].sub.3 Rh.sup.+ (counterion).sup.- compounds of this invention, e.g., by contacting the salts of the invention with carbon monoxide gas, produces salts having the formula:[(aryl).sub.3 P].sub.3 Rh(CO).sub.n.sup.+ (counterion).sup.-,wherein n is 1 or 2, and (counterion).sup.- is as defined above.Type: GrantFiled: October 12, 1983Date of Patent: December 3, 1985Assignee: Minnesota Mining and Manufacturing CompanyInventors: Allen R. Siedle, Richard D. Howells
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Patent number: 4539423Abstract: Disclosed is an improved process for preparing diesters of malonic acid by subjecting ketene, carbon monoxide and an ester of nitrous acid to a liquid phase reaction in an organic solvent, in which the reaction is carried out in the presence of a catalyst of a platinum group metal complex represented by the formula:L.sub.2 MX.sub.2wherein, L represents a ligand selected from the group consisting of triorganophosphines, triorganophosphite and triorganoarsines; M represents a platinum group metal; and X represents a halogen or an acetic acid ion.Type: GrantFiled: October 6, 1982Date of Patent: September 3, 1985Assignee: UBE Industries Ltd.Inventors: Hiroshi Itatani, Mikito Kashima, Tsutomu Suehiro
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Patent number: 4537982Abstract: Nickel-compounds, producible by reaction of Nickel-(O)-compound or a compound convertible thereto in situ with two different compounds corresponding to the following formulae ##STR1## are useful as catalysts in the polymerization of olefins.Type: GrantFiled: July 22, 1983Date of Patent: August 27, 1985Assignee: Bayer AktiengesellschaftInventors: Karl-Heinz A. O. Starzewski, Josef Witte
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Patent number: 4533651Abstract: Catalyst systems for the oligomerization and/or isomerization of olefins which comprise a nickel (II) complex and a co-catalyst. The nickel (II) complex is a square planar species with a trivalent Group V donor ligand, preferably a phosphine or phosphite ligand, a halogen or pseudo-halogen ligand and a bidentate dithio ligand, especially a substituted dithio-.beta.-diketone ligand.Type: GrantFiled: October 17, 1983Date of Patent: August 6, 1985Assignee: Commonwealth Scientific and Industrial Research OrganizationInventors: Anthony F. Masters, Kingsley J. Cavell
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Patent number: 4529554Abstract: A process is provided for preparing nickel ylides which are themselves novel compounds defined by the following Formula I: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.Type: GrantFiled: August 18, 1980Date of Patent: July 16, 1985Assignee: Gulf Research & Development CompanyInventors: David L. Beach, James J. Harrison