Rhodium Containing Patents (Class 502/166)
  • Patent number: 6017843
    Abstract: The present invention discloses an improved catalyst composition for preparing 5-formylvalerate esters by hydroformylation of pentenoic esters monoxide with good activity, high selectivity in the presence of hydrogen and carbon.
    Type: Grant
    Filed: June 19, 1998
    Date of Patent: January 25, 2000
    Assignee: Industrial Technology Research Institute
    Inventors: Jing-Cherng Tsai, Hsi-Hui Tai, Tsai-Tien Su, Bor-Ping Wang
  • Patent number: 5981422
    Abstract: Stoichiometric and catalytic chemical transformations may be carried out in solution using novel fluorous multiphase systems (FMS). The term "fluorous" is defined as a carbon-fluorine bond rich organic molecule which is generated by replacing hydrogen atoms bonded to carbon atoms with fluorine. The novel complexes suitable for use as fluorous catalysts and reagents in the present invention contain sufficient number of fluorous moieties to render them preferentially soluble in the appropriate fluorous solvent without impairing the ability of the catalyst or reagent to be effective or participate in the corresponding reaction.
    Type: Grant
    Filed: August 26, 1997
    Date of Patent: November 9, 1999
    Assignee: Exxon Research and Engineering Co.
    Inventors: Istvan Tamas Horvath, Jozsef Rabai
  • Patent number: 5935892
    Abstract: Supported phase catalysts in which the support phase is highly polar, most preferably ethylene glycol or glycerol, are disclosed. An organometallic compound, preferably a metal complex of chiral sulfonated 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) is dissolved in the support phase. Such supported phase catalysts are useful for asymmetric synthesis of optically active compounds, including the asymmetric hydrogenation of prochiral unsaturated carbon-hetero atom bonds, such as ketones, imines and beta-keto esters. The phenyl groups of the BINAP ligand are at least meno-sulfonated and the ligand overall is terra- to hexa-sulfonated. Ruthemium is the perferred metal.
    Type: Grant
    Filed: April 10, 1997
    Date of Patent: August 10, 1999
    Assignee: California Institute of Technology
    Inventors: Mark E. Davis, Kam To Wan
  • Patent number: 5929289
    Abstract: The present invention provides a hydroformylation process comprising: (1) forming a reaction mixture containing: (a) an olefinic compound, (b) hydrogen, (c) carbon monoxide, (d) a phosphite in which each phosphorus atom is bonded to three oxygen atoms and at least one such oxygen atom is bonded to a carbon atom of an aromatic ring that is adjacent to another carbon atom of said ring having a pendant monovalent group having a steric hindrance at least as great as the steric hindrance of the isopropyl group, (e) a catalytic amount of rhodium, and (f) a Group VIII metal (other than a rhodium) in an amount sufficient to reduce the rhodium-catalyzed decomposition of the phosphite during the hydroformylation process; and (2) maintaining the reaction mixture under conditions at which the olefinic compound reacts with the hydrogen and carbon monoxide to form an aldehyde.
    Type: Grant
    Filed: March 3, 1998
    Date of Patent: July 27, 1999
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Anthony George Abatjoglou, David Robert Bryant, John Michael Maher
  • Patent number: 5922634
    Abstract: A water-soluble catalyst composition comprising rhodium complexes containing diphosphine ligands, wherein the diphosphine ligands present are compounds of the formula ##STR1## where R.sup.1 is selected from the group consisting of carboxylate (COO.sup.-), sulfonate (SO.sub.3.sup.-), phosphonate (PO.sub.3.sup.2-) and 2-amino ethanebisphosphonate ?NH--CH.sub.2 --CH(PO.sub.3.sup.2-).sub.2 !, R.sup.2 is selected from the group consisting of a straight-chain alkylene of 1 to 8 carbon atoms, an oxygen-containing alkylene of 2 to 6 carbon atoms, cycloalkylene of 3 to 10 carbon atoms and a member of the formulae II, III, IV or V ##STR2## a, b, c, d, e, f, g, h, k and l are individually 0 to 1, where at least one of a, b, c, d, e, f, g, h, k or l has to be equal to 1, x(s) are individually 0 or 1, y is an integer of 1 to 24, R.sup.3 and R.sup.
    Type: Grant
    Filed: April 17, 1997
    Date of Patent: July 13, 1999
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Bahrmann, Peter Lappe, Thomas Muller
  • Patent number: 5872273
    Abstract: A novel diphosphine compound of the formula (I): ##STR1## where R.sup.1 and R.sup.2 represent independently cycloalkyl, unsubstituted or substituted phenyl, or a five-membered heteroaromatic ring. The compound is useful as a ligand for an asymmetric reaction, in particular, as an asymmetric hydrogenation catalyst.
    Type: Grant
    Filed: December 22, 1997
    Date of Patent: February 16, 1999
    Assignee: Takasago International Corporation
    Inventors: Takao Saito, Tohru Yokozawa, Xiaoyaong Zhang, Noburo Sayo
  • Patent number: 5858905
    Abstract: Catalyst systems which comprise a transition metal and a pyrophosphite ligand are particularly effective as catalysts for hydrosilation reactions. The transition metal is from groups 7-11 of the Periodic Table, and the pyrophosphite has the following formula: ##STR1## wherein E and E' are independently a direct bond, --S--, --Se--, or --CR.sub.9 R.sub.10 -- where R.sub.9 and R.sub.10 are independently hydrogen or alkyl of 1-18 carbon atoms, and R.sub.10 can also be phenyl. R is H or methyl, R.sub.1-8 are independently H, C.sub.1-18 alkyl, C.sub.5-12 cycloalkyl, or C.sub.7-15 phenylalkyl.
    Type: Grant
    Filed: July 23, 1997
    Date of Patent: January 12, 1999
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Andrea R. Smith, Stephen D. Pastor
  • Patent number: 5827794
    Abstract: The present invention relates to water soluble chiral sulfonated 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl and its use as organometallic catalysts for asymmetric synthesis of optically active compounds. Asymmetric reactions of the present invention include those reactions in which organometallic catalysts are commonly used. Such reactions include, but are not limited to, reduction and isomerization reactions on unsaturated substrates and carbon--carbon bond forming reactions. Examples of such reactions include, but are not limited to, hydrogenation, hydroboration, hydrosilylation, hydride reduction, hydroformylation, alkylation, allylic alkylation, arylation, alkenylation, epoxidation, hydrocyanation, disilylation, cyclization and isomerization reactions.The catalysts of the present invention provide the advantage of functioning in the presence of water without loss in enantioselectivity relative to the nonsulfonated BINAP catalyst in an organic solvent.
    Type: Grant
    Filed: September 28, 1995
    Date of Patent: October 27, 1998
    Assignee: California Institute of Technology
    Inventors: Mark E. Davis, Kam To Wan
  • Patent number: 5817848
    Abstract: The invention relates to a bidentate phosphine ligand, the phosphorus atoms of the phosphine being connected via a bridge group, the bridge group of the bidentate phosphine ligand consisting of an ortho-anellated annular system, comprising two aryl groups, which aryl groups are connected by two bridges, the first bridge consisting of an --O-- or an --S-- atom and the second bridge being a group that contains an oxygen, sulphur, nitrogen, silicon or carbon atom or a combination of these atoms, the two phosphorus atoms being connected to the two aryl groups of the bridge group at the ortho-position relative to the --O-- or --S-- atom of the first bridge.The invention also relates to the use of this bidentate phosphium ligand in a catalyst system comprising also a transition metal compound which is used in the following type of reactions: hydroformylation hydrogenation, hydrocyanation, polymerization, isomerisation, carboxylation, cross coupling and metathesis.
    Type: Grant
    Filed: November 6, 1996
    Date of Patent: October 6, 1998
    Assignee: DSM N.V.
    Inventors: Paulus C. J. Kamer, Mirko Kranenburg, Petrus W. N. M. van Leeuwen, Johannes G. de Vries
  • Patent number: 5801261
    Abstract: The invention relates to enantiomerically pure bisphosphines of the general formula (I) ##STR1## where R is as defined in the description,a process for their preparation and their use in metal complexes as catalysts for asymmetric reactions, in particular asymmetric hydrogenations.
    Type: Grant
    Filed: October 17, 1997
    Date of Patent: September 1, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Christian Laue, Georg Schroder, Dieter Arlt
  • Patent number: 5789333
    Abstract: The present invention provides new catalyst formats which comprise a supported catalyst tethered to a second and different catalyst by a suitable tethering ligand. A preferred system comprises a heterogeneous supported metal catalyst tethered to a homogeneous catalyst. This combination of homogeneous and heterogeneous catalysts has a sufficient lifetime and unusually high catalytic activity in arene hydrogenations, and potentially many other reactions as well, including, but not limited to hydroformylation, hydrosilation, olefin oxidation, isomerization, hydrocyanation, olefin metathesis, olefin polymerization, carbonylation, enantioselective catalysis and photoduplication. These catalysts are easily separated from the products, and can be reused repeatedly, making these systems very economical.
    Type: Grant
    Filed: March 5, 1997
    Date of Patent: August 4, 1998
    Assignee: Iowa State University Research Foundation, Inc.
    Inventors: Robert J. Angelici, Hanrong Gao
  • Patent number: 5731255
    Abstract: A carbonylation catalytic system comprises (A) a combination of (A1) a Group VIII metal source of Periodic Table of the Elements (e.g., palladium, palladium chloride) supported on a carrier, (A2) a ligand such as triphenylphosphine and (A3) an acid such as an alkyl-sulfonic acid, or (B) a combination of (B1) the Group VIII metal source except for palladium (e.g., a platinum compound), (B2) a ligand such as triphenylphosphine and (B3) an electron donative compound having an electron donability .DELTA..nu.D of not less than 2 (for instance, an amine such as a heterocyclic tertiary amine). The catalytic system (B) may further comprise (B4) an acid such as methanesulfonic acid.
    Type: Grant
    Filed: July 20, 1995
    Date of Patent: March 24, 1998
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Li Rui Pan, Tomohide Ina, Kazuyuki Matsuoka
  • Patent number: 5625107
    Abstract: The present invention relates to a new catalyst for converting methane into ethane, preparation thereof, and process for manufacturing ethylene using said catalyst. The conversion reaction catalyst in the present invention is employed in converting directly methane or methane-containing gas in the presence of the above catalyst with the following general formula (1).Ma.Pc.D/S (1)Where,M is a metal cluster or metal complex compound selected from the group of VIII, VII and VI series;S is an inorganic carrier;P is a promoter of phosphorus compound;D is a cobalt compound.And "a" is weight percentage of metal cluster or metal complex compound in catalyst, having a value of 0.01 to 10, "c" is weight percentage of promoter in catalyst, ranging from 1.0 to 35.0.
    Type: Grant
    Filed: August 30, 1995
    Date of Patent: April 29, 1997
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Dae C. Park, Pyung K. Ahn
  • Patent number: 5580991
    Abstract: The disclosure describes a method for separating a ruthenium complex, which comprises removing an objective hydrogenation reaction product from a hydrogenation reaction solution of an organic carbonyl compound in the presence of a ruthenium complex having a tertiary organic phosphorus compound as ligand to obtain a catalyst solution, contacting said catalyst solution with a polar solvent, and carrying out a phase-separation into a liquid phase substantially composed of the polar solvent and an another liquid phase substantially containing the ruthenium complex.
    Type: Grant
    Filed: April 4, 1995
    Date of Patent: December 3, 1996
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Hitoshi Sugiyama, Kazunari Takahashi, Haruhiko Kusaka
  • Patent number: 5574171
    Abstract: Enantioselective hydroformylation of vinyl compounds using a catalyst composition of a chiral carbohydrate phosphorous ligand with a Rh, Pt, Co or Ir metal, to produce chiral 2-substituted propanals, wherein the phosphorous of the ligand is substituted with electron withdrawing groups.
    Type: Grant
    Filed: April 24, 1995
    Date of Patent: November 12, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Timothy A. Ayers, Thaliyil V. Rajanbabu
  • Patent number: 5565398
    Abstract: Sulfonated diphosphines of the formula ##STR1## in which Ar is m--C.sub.6 H.sub.4 --SO.sub.3 M, M is hydrogen, ammonium, a monovalent metal, or the chemical equivalent of a polyvalent metal; Ph is phenyl; the m's are individually 1 or 2, and the n's are individually 0, 1, or 2. A method of their preparation and the hydroformylation of olefins and olefinically unsaturated compounds using these compounds as a constituent of water-soluble catalyst systems are also disclosed.
    Type: Grant
    Filed: November 2, 1995
    Date of Patent: October 15, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang A. Herrmann, Rainer Manetsberger, Helmut Bahrmann, Christian Kohlpaintner
  • Patent number: 5556998
    Abstract: The present invention provides a novel transition metal complex which catalyzes asymmetric hydrogenation reaction. The present invention also provides a process for the preparation of the foregoing novel complex. The present invention further provides an asymmetric hydrogenation catalyst comprising the foregoing novel complex.
    Type: Grant
    Filed: March 13, 1995
    Date of Patent: September 17, 1996
    Assignee: Takasago International Corporation
    Inventors: Akira Miyashita, Takeshi Chiba, Hiroyuki Nohira, Hidemasa Takaya
  • Patent number: 5516739
    Abstract: A catalyst and method for the co-and terpolymerization of monomers of ethylene, other olefins, and alkynes with carbon monoxide is provided. Such a catalyst a method can be used for form living polymers. The catalyst of the present invention comprises an active cationic portion of the formula ##STR1## wherein M is a Group VIII metal, L.sup.1 and L.sup.2 are two electron donor ligands or are joined to form a bidentate four electron donor ligand, R is alkyl, aryl or acyl, and L.sup.3 is CO or a ligand capable of being displaced by CO; and a non-coordinating anionic portion, soluble in inert solvents of the formulaX.sub.n G.sup.-wherein G is B, CH, N, SO.sub.3, SO.sub.3 CH, R.sub.f SO.sub.2 CH, or NSO.sub.2 R.sub.f wherein R.sub.f is C.sub.n F.sub.2+1 where n is 1 to 10 and X is F,R.sub.f SO.sub.2, FSO.sub.2 or C.sub.6 H.sub.(5-m) Z.sub.m wherein Z is F, C1, a hydrocarbyl radical, substituted hydrocarbyl radical or combinations thereof, and m is from 1 to 5, and n of X.sub.n is from 1 to 4.
    Type: Grant
    Filed: November 24, 1993
    Date of Patent: May 14, 1996
    Assignees: The University of North Carolina at Chapel Hill, The University of North Carolina at Greensboro
    Inventors: James C. Barborak, Maurice S. Brookhart
  • Patent number: 5498584
    Abstract: Disclosed in a process for the homogeneous, catalytic hydrogenation of epoxyalkenes and epoxycyclo-alkenes, especially conjugated .gamma.,.delta.-epoxyalkenes and epoxycycloalkenes, to the corresponding epoxyalkanes and epoxycycloalkanes using a solution of a complex rhodium catalyst whereby the olefinic unsaturation is hydrogenated without significant hydrogenolysis of the conjugated epoxy group.
    Type: Grant
    Filed: September 23, 1994
    Date of Patent: March 12, 1996
    Assignee: Eastman Chemical Company
    Inventor: Thomas A. Puckette
  • Patent number: 5488153
    Abstract: A process or the liquid phase carbonylation of methanol or a reactive derivative thereof comprises contacting carbon monoxide with a liquid reaction composition comprising methanol or a reactive derivative thereof, a halogen promoter and a rhodium catalyst system comprising a rhodium component and a bidentate phosphorus-sulphur ligand, the ligand comprising a phosphorus dative center linked to a sulphur dative or anionic center by a substantially unreactive backbone structure comprising two connecting carbon atoms or a connecting carbon and a connecting phosphorus atom. Novel rhodium ligand complexes of formula [Rh(CO)L].sub.m and Rh(CO)LY] wherein Y is a halogen, m is a number less than 10 and L is ##STR1## wherein the R groups are independently selected from C.sub.1 to C.sub.20 alkyl, cycloalkyl, aryl, substituted aryl and optionally substituted aralkyl; the R.sup.5 groups are selected from hydrogen, C.sub.1 to C.sub.
    Type: Grant
    Filed: June 21, 1994
    Date of Patent: January 30, 1996
    Assignee: BP Chemicals Limited
    Inventors: Michael J. Baker, Jonathan R. Dilworth, John G. Sunley, Nigel Wheatley
  • Patent number: 5481006
    Abstract: A process and catalyst composition are provided for the highly efficient enantioselective hydrogenation of dehydroamino acid derivatives. The catalyst composition comprises rhodium or iridium and a diphosphinite carbohydrate ligand, wherein the phosphorous atoms are attached to aromatic groups substituted with electron-donating substituents. Also provided is a means to selectively produce .alpha. amino acids in either the L or the D form, based upon use of a sugar in the ligand with phosphinites attached in an absolute Right-Left or Left-Right configuration, respectively.
    Type: Grant
    Filed: January 11, 1994
    Date of Patent: January 2, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Timothy A. Ayers, Thaliyil V. Rajanbabu
  • Patent number: 5449653
    Abstract: A process for producing a 1,3-diol, e.g., 1,3-propanediol, and/or a 3-hydroxyaldehyde, e.g., 3-hydroxypropionaldehyde, is disclosed which comprises contacting a combination of an epoxide, carbon monoxide and hydrogen in the presence of a rhodium-containing.catalyst composition effective to promote the hydroformylation of the epoxide at conditions effective to form at least one of a 1,3-diol and a 3-hydroxyaldehyde. The rhodium-containing catalyst composition comprises an anionic rhodium-containing complex. A promoter component is preferably provided to enhance at least one of the rate and selectivity of the epoxide hydroformylation reaction. Rhodium-containing compositions and a processes for producing rhodium-containing compositions are also disclosed.
    Type: Grant
    Filed: February 5, 1993
    Date of Patent: September 12, 1995
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John R. Briggs, John M. Maher, Arnold M. Harrison
  • Patent number: 5411995
    Abstract: Xanthate, dithiocarbamate and dithiophosphate salts of transition metals, together with a coinitiator selected from organic halogen and tertiary amine compounds provide light activated initiator systems for radically polymerizable ethylenically unsaturated compounds such as (meth)acrylate esters.
    Type: Grant
    Filed: April 8, 1993
    Date of Patent: May 2, 1995
    Assignee: Loctite Corporation
    Inventor: Darchun B. Yang
  • Patent number: 5391773
    Abstract: Disclosed is a process for the homogeneous, catalytic hydrogenation of epoxyalkenes and epoxycycloalkenes, especially conjugated .gamma.,.delta.-epoxyalkenes and .gamma.,.delta.-epoxycycloalkenes, to the corresponding epoxyalkanes and epoxycycloalkanes using a solution of a complex rhodium catalyst whereby the olefinic unsaturation is hydrogenated without significant hydrogenolysis of the conjugated epoxy group.
    Type: Grant
    Filed: June 17, 1994
    Date of Patent: February 21, 1995
    Assignee: Eastman Chemical Company
    Inventor: Thomas A. Puckette
  • Patent number: 5387569
    Abstract: A catalyst solution comprising one or more compounds of a metal catalyst and an organic solvent selected from the group consisting of a glycol derivative, an alkyl pyrrolidone, and an alkoxy ethyl ether, wherein no additional chloride-containing compounds are added to the solution. The metal can be selected from the group consisting of platinum, rhenium and rhodium. The compounds can be selected from the group consisting of H.sub.2 PtCl.sub.6.6H.sub.2 O, Re.sub.2 (CO).sub.10, Re.sub.2 O.sub.7, LiReO.sub.4 and RhCl.sub.3.4H.sub.2 O. The catalytic solutions are useful in conversion of pollutants from automotive engines and the like. In a particularly preferred embodiment, the solution contains three metals: platinum, rhenium, and rhodium.
    Type: Grant
    Filed: February 25, 1992
    Date of Patent: February 7, 1995
    Assignee: Blue Planet Technologies Co., L.P.
    Inventors: Eugene Shustorovich, Richard Montano, Aleksandr Bragin, Veniamin Kalner, Konstantin Solntsev, Nikolai Moiseev, Yuri Buslaev
  • Patent number: 5352813
    Abstract: An improved process is provided for the carbonylation of methanol to acetic acid and/or its derivatives, especially methyl acetate, under mild reaction conditions using a novel catalyst precursor. The precursor is a transition metal complex having a heterodifunctional bidentate phosphorus--nitrogen ligand attached to the metal. The carbonylation reaction can now typically be carried out at 80.degree. C. and CO pressure of 40 p.s.i.g.
    Type: Grant
    Filed: September 3, 1991
    Date of Patent: October 4, 1994
    Assignee: University of Alberta
    Inventors: Ronald G. Cavell, Kattesh V. Katti
  • Patent number: 5334791
    Abstract: A process is provided for hydrogenating a non-aromatic unsaturated hydrocarbon, comprising reacting the hydrocarbon with a catalyst precursor which includes a source of a group VIIIB transition metal from the second or third rows of the periodic table and a heterobifunctional ligand constructed with a phosphine center and an imine nitrogen center, in the presence of hydrogen and a promoter selected from secondary or tertiary acyclic alkyl amines in a suitable solvent which solubilizes the hydrocarbon, the catalyst precursor, the hydrogen, and the promoter.
    Type: Grant
    Filed: May 22, 1992
    Date of Patent: August 2, 1994
    Assignee: Ligands Inc.
    Inventors: Ronald G. Cavell, David J. Law, Robert W. Reed
  • Patent number: 5321139
    Abstract: Two processes are described for the preparation of the optically pure compounds of formula 1: ##STR1## in which R.sup.1 and R.sup.2 are e.g. alkyl, R.sup.3 and R.sup.4 are e.g. hydrogen and R.sup.5 is e.g. hydrogen. Both processes include, as key steps, the enantioselective hydrogenation of a C.dbd.C double bond and the regioselective formation of a dicarboxylic acid monoamide derivative. In one process a phenylitaconic acid derivative is asymmetrically hydrogenated to give an optically active (R)-benzylsuccinic acid which is then converted to a diester, said diester being converted to the monoamide compound of formula 1. In the second process, a phenylitaconic acid derivative is converted to its anhydride, and the anhydride is then converted to a monoamide which is then asymmetrically hydrogenated to give the compound of formula 1.
    Type: Grant
    Filed: February 16, 1993
    Date of Patent: June 14, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ulrich Lerch, Heiner Jendralla, Bernhard Seuring, Rainer Henning
  • Patent number: 5308819
    Abstract: Compounds where a solid carrier material which contains diphosphine rhodium or iridium complexes fixed on the surface thereof, of which the carrier material has the formula IV or IVa: ##STR1## wherein Y denotes two monoolefin ligands or a diene ligand, M is Ir(I) or Rh(i), Z is --Cl, --Br or -I, A.crclbar. is the anion of an oxyacid or complex acid, T is a solid carrier material, r is 0, 1 or 2, and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are as defined in claim 1. These materials are heterogeneous and separable catalysts for the asymmetrical hydrogenation of prochiral compounds containing carbon double bonds or carbon/hetero atom double bonds, for example ketones and imines.
    Type: Grant
    Filed: July 14, 1993
    Date of Patent: May 3, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Benoit Pugin, Felix Spindler, Manfred Muller
  • Patent number: 5276210
    Abstract: An improved allyl alcohol hydroformylation process and catalyst are disclosed. The process uses a catalyst system comprising a Group VIII metal carbonyl complex catalyst, a trisubstituted phosphine, a neutral Group VIII(a) metal complex cocatalyst, and optionally, a diphosphinoalkane. The process uniquely gives an enhanced linear:branched aldehyde product ratio.
    Type: Grant
    Filed: March 29, 1993
    Date of Patent: January 4, 1994
    Assignee: ARCO Chemical Technology, L.P.
    Inventors: Rangasamy Pitchai, Anne M. Gaffney, Manish K. Nandi, Yuan-Zhang Han
  • Patent number: 5266545
    Abstract: A catalyst composition useful in the preparation of a polymer composition includes a Group VIII metal and a phosphorus bidentate ligand of the general formula (R.sub.2)(R.sub.4)P--R.sub.3 --P(R.sub.2)(R.sub.4) wherein R.sub.2 and R.sub.4 are optionally polar substituted alkyl groups, differing from each other in carbon number, and wherein R.sub.3 is a divalent organic bridging group which contains four atoms. Such catalyst compositions are particularly useful for preparing copolymers of carbon monoxide with .alpha.-olefins having at least three carbon atoms.
    Type: Grant
    Filed: January 21, 1993
    Date of Patent: November 30, 1993
    Assignee: Shell Oil Company
    Inventors: Peter A. A. Klusener, Johannes J. M. Snel
  • Patent number: 5260491
    Abstract: Cationic rhodium bis(dioxaphosphorus heterocycle) complexes of the formula: ##STR1## in which R is preferably ##STR2## or (CH.sub.2).sub.2-5, Y . . . Y is any backbone chain of 2-5 atoms, and L and L' are any stabilizing ligands, used in hydroformylation of olefins to obtain regioselectivity of branched aldehyde products. The formula of the catalyst may include substituents which do not interfere with the branched product regioselectivity of the catalyst as a whole. In the hydroformylation method the olefin is reacted with hydrogen and carbon monoxide in the presence of the catalyst at a temperature and pressure sufficient to permit the desired branched product regioselectivity.
    Type: Grant
    Filed: October 27, 1992
    Date of Patent: November 9, 1993
    Assignee: New York University
    Inventors: Donald J. Wink, Thomas J. Kwok
  • Patent number: 5242878
    Abstract: Polyketones can be formed from carbon monoxide and at least one olefin by using, as a catalytic complex, a catalyst which comprises a Group VIII metal, an anion of an acid having a pK.sub.a of less than about four, and a tin tetradentate phosphine ligand, preferably of the formula Sn(RPR'.sub.2).sub.4 where R is methylene and R' is phenyl.
    Type: Grant
    Filed: April 8, 1992
    Date of Patent: September 7, 1993
    Assignee: Akzo N.V.
    Inventor: David L. Kershner
  • Patent number: 5225387
    Abstract: A process for producing a 1,3-diol, e.g., 1,3-propanediol, or a 3-hydroxyaldehyde is disclosed which comprises contacting a combination of an epoxide, carbon monoxide and hydrogen in the present of a rhodium-containing catalyst effective to promote the hydroformylation of the epoxide at conditions effective to form at least one of a 1,3-diol and a 3-hydroxyaldehyde, the contacting occurring in the substantial absence of a promoting amount of alkali metal ions, and at least a portion of the rhodium-containing catalyst being formed substantially without incorporation of the epoxide. A process for producing such rhodium-containing compositions is also disclosed.
    Type: Grant
    Filed: April 25, 1991
    Date of Patent: July 6, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John R. Briggs, John M. Maher, Arnold M. Harrison
  • Patent number: 5223648
    Abstract: The hydroformylation of olefins and olefinically unsaturated compounds in the presence of a water-soluble rhodium complex compound Which contains, as a ligand, at least one sulfonated diphosphine, and a catalyst therefor.
    Type: Grant
    Filed: August 25, 1992
    Date of Patent: June 29, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Herrmann, Christian Kohlpaintner, Helmut Bahrmann
  • Patent number: 5217760
    Abstract: Xanthate, dithiocarbamate and dithiophosphate salts of transition metals, together with a coinitiator selected from organic halogen and tertiary amine compounds provide light activated initiator systems for radically polymerizable ethylenically unsaturated compounds such as (meth)acrylate esters.
    Type: Grant
    Filed: July 20, 1990
    Date of Patent: June 8, 1993
    Assignee: Loctite Corporation
    Inventor: Darchun B. Yang
  • Patent number: 5210318
    Abstract: A process for producing a 1,3-diol, e.g., 1,3-propanediol, and/or a 3-hydroxyaldehyde, e.g., 3-hydroxypropionaldehyde, is disclosed which comprises contacting a combination of an epoxide, carbon monoxide and hydrogen in the presence of a rhodium-containing catalyst composition effective to promote the hydroformylation of the epoxide at conditions effective to form at least one of a 1,3-diol and a 3-hydroxyaldehyde. The rhodium-containing catalyst composition comprises an anionic rhodium-containing complex. A promoter component is preferably provided to enhance at least one of the rate and selectivity of the epoxide hydroformylation reaction Rhodium-containing compositions and a processes for producing rhodium-containing compositions are also disclosed.
    Type: Grant
    Filed: March 18, 1991
    Date of Patent: May 11, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John R. Briggs, John M. Maher, Arnold M. Harrison
  • Patent number: 5200380
    Abstract: The hydroformylation of olefins and olefinically unsaturated compounds in the presence of a water-soluble rhodium complex compound which contains, as a ligand, at least one sulfonated diphosphine, and a catalyst therefor.
    Type: Grant
    Filed: December 6, 1991
    Date of Patent: April 6, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Herrmann, Christian Kohlpaintner, Helmut Bahrmann
  • Patent number: 5187134
    Abstract: This invention relates to formed, polymeric complexes of metals of the eighth subgroup of the periodic system with ligands of an organosiloxane copolycondensate optionally cross-linked by means of cross-linking agents containing Si, Ti, Zr and/or Al, in the form of statistical, block or mixed copolycondensates. The ratio between the number of moles of phosphine units and the number of moles of bound metal atoms is 1:1 to 1000 to 1 and the ratio between the amine units and the phosphine is preferably 5:95 to 95:5 mole %. The polymeric complex compounds are present macroscopically as spherical particles with a diameter in the range of 0.01 to 3.0 mm, a BET surface of greater than 0 to 1000 m.sup.2 /g, a specific pore volume of 0.01 to 6.5 ml/g and a bulk density of 50 to 1000 g/l. The invention also includes several methods of preparing the complexes with post-treatment stages and the use of the polymeric metal complexes as catalysts in organic chemistry.
    Type: Grant
    Filed: November 1, 1991
    Date of Patent: February 16, 1993
    Assignee: Degussa AG
    Inventors: Peter Panster, Robert Gradl
  • Patent number: 5179055
    Abstract: Cationic rhodium bis(dioxaphosphorus heterocycle) complexes of the formula: ##STR1## in which R is preferably ##STR2## or (CH.sub.2).sub.2-5, Y . . . Y is any backbone chain of 2-5 atoms, and L and L' are any stabilizing ligands, used in hydroformylation of olefins to obtain regioselectivity of branched aldehyde products. The formula of the catalyst may include substituents which do not interfere with the branched product regioselectivity of the catalyst as a whole. In the hydroformylation method the olefin is reacted with hydrogen and carbon monoxide in the presence of the catalyst at a temperature and pressure sufficient to permit the desired branched product regioselectivity.
    Type: Grant
    Filed: September 24, 1990
    Date of Patent: January 12, 1993
    Assignee: New York University
    Inventors: Donald J. Wink, Thomas J. Kwok
  • Patent number: 5177044
    Abstract: A novel catalyst composition containing a Group VIII metal and a phosphorus bidentate ligand wherein each phosphorus atom forms part of a phosphacyclohexyl structure.
    Type: Grant
    Filed: November 20, 1991
    Date of Patent: January 5, 1993
    Assignee: Shell Oil Company
    Inventors: Johannes A. van Doorn, Johannes J. M. Snel, Peter A. A. Klusener
  • Patent number: 5175311
    Abstract: A chiral catalyst is disclosed together with methods of using it for enantioselective syntheses. The chiral catalyst includes a nucleus with two metal atoms that has four bridging ligands oriented radially to the axis of the nucleus. Each of these ligands includes two complexing atoms each complexed to one of the metal atoms. At least one of the bridging ligands includes a chiral center which is bonded to one of the complexing atoms. Preferably, all four of the bridging ligands include a chiral center bonded to one of the complexing atoms. The catalyst of the invention has been found to be useful in catalyzing carbenoid transformation reactions such as cyclopropanation.
    Type: Grant
    Filed: March 29, 1990
    Date of Patent: December 29, 1992
    Assignee: Research Corporation Technologies, Inc.
    Inventor: Michael F. Doyle
  • Patent number: 5162279
    Abstract: An immobilized metal complex is disclosed, which is immobilized on an inorganic carrier to which a long molecular chain compound capable of surrounding the metal complex is bound in an amount of at least 1.5 mols per mol of the metal complex. This novel immobilized metal complex has an excellent stability and can be used as a metal complex catalyst providing excellent reactivity.
    Type: Grant
    Filed: July 8, 1991
    Date of Patent: November 10, 1992
    Assignee: Director-General of Agency of Industrial Science and Technology
    Inventor: Keiji Miki
  • Patent number: 5135901
    Abstract: A catalyst used in a process for producing a .beta.-hydroxyester product or a .beta.-hydroxyaldehyde product from ethylene oxide, carbon monoxide, and, optionally, hydrogen, is disclosed. This process uses, as a catalyst, a catalyst comprising rhodium, ruthenium, and a Group Va promoter.
    Type: Grant
    Filed: June 7, 1991
    Date of Patent: August 4, 1992
    Assignee: Eastman Chemical Company
    Inventor: William A. Beavers
  • Patent number: 5124300
    Abstract: A catalyst system, which comprises:a) a source of a Group VIII metal;b) a phosphine having an aromatic substituent which contains an imino nitrogen atom;c) a source of protons; andd) a tertiary amine.
    Type: Grant
    Filed: February 4, 1991
    Date of Patent: June 23, 1992
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 5124294
    Abstract: The present invention concerns a catalyst system and a process for selectively producing alcohols from olefines and synthesis gas. The catalyst system comprises one or several metal cluster compounds belonging to the cobalt group on an inorganic carrier and an amine of the form NR.sub.1 R.sub.2 R.sub.3, where R.sub.1,R.sub.2 and R.sub.3 are either hydrogen or an aliphatic or aromatic group containing 1 to 8 carbon atoms.
    Type: Grant
    Filed: August 25, 1987
    Date of Patent: June 23, 1992
    Assignee: Neste Oy
    Inventors: Leila Alvila, Tapani Pakkanen, Outi Krause, Matteus Joutsimo
  • Patent number: 5113022
    Abstract: This invention relates to novel ionic phosphites and the use thereof as ligands in homogenous transition metal catalyzed processes, especially hydroformylation.
    Type: Grant
    Filed: August 8, 1991
    Date of Patent: May 12, 1992
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Anthony G. Abatjoglou, David R. Bryant
  • Patent number: 5086027
    Abstract: A catalyst composition comprised of: about 0.005 to 5.0 wt. % noble metal, about 0.5 to 5 wt. % of at least one Group VIII metal, and about 3 to 18 wt. % of a Group VI metal, and a refractory support, wherein the noble metal is incorporated into the refractory support by use of a precursor represented by ML.sub.2 when the noble metal is Pt or Pd and ML.sub.3, when the noble metal is Rh or Ir, where M is the noble metal and L is a ligand selected from the dithiocarbamates, dithiophosphates, dithiophosphinates, xanthates, thioxanthates, and further wherein L has organo groups having a sufficient number of carbon atoms to render the noble metal complex soluble in oil.
    Type: Grant
    Filed: December 18, 1990
    Date of Patent: February 4, 1992
    Assignee: Exxon Research and Engineering Company
    Inventors: Gopal H. Singhal, William E. Winter, Kenneth L. Riley, Kenneth L. Trachte
  • Patent number: 5075470
    Abstract: A process for the preparation of .mu.-3-carbopentazane-N.sup.1, N.sup.4 :N.sup.2, N.sup.5 -bis-[bis(triphenylphosphine)rhodium (I)] dinitrate by the reaction of tris(triphenylphosphine)nitratorhodium (I) with hydrazine in degassed methanol under an inert atmosphere.
    Type: Grant
    Filed: July 26, 1990
    Date of Patent: December 24, 1991
    Assignee: Plurichemie Anstalt
    Inventors: William Heggie, Philip R. Page, Ivan Villax, Indira Ghatak, Michael B. Hursthouse
  • Patent number: 5028576
    Abstract: A catalyst system which comprises:a) a group VIII metal compound, andb) a monophosphine of formula ##STR1## where R.sup.1 represents an aliphatic hydrocarbyl group, R.sup.2 represents an optionally substituted aromatic heterocyclic group having 5 or 6 ring atoms of which at least one is nitrogen, which may form part of an optionally substituted larger condensed ring structure, and R.sup.3 independently has the meaning of R.sup.2 or represents an optionally substituted aryl group or an acid addition salt thereof, and their use in the carbonylation of unsaturated compounds.
    Type: Grant
    Filed: March 1, 1990
    Date of Patent: July 2, 1991
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Petrus H. M. Budzelaar