Rhodium Containing Patents (Class 502/166)
  • Patent number: 9018420
    Abstract: The present invention provides a composition comprising: a) an inert porous support material, b) an ionic liquid, c) a metal selected from group 9 of the Periodic Table of the Elements, d) a phosphorus-containing organic ligand, e) at least one organic amine. The present invention further provides a process for hydroformylating olefin-containing hydrocarbon mixtures to aldehydes with addition of the inventive composition as a catalytically active composition, wherein: a) the water content of the olefin-containing hydrocarbon mixture is adjusted to not more than 20 ppm, b) the content of polyunsaturated compounds in the olefin-containing hydrocarbon mixture is adjusted to not more than 3000 ppm, c) a molar ratio of organic amines according to claims 10-13 to phosphorus-containing organic ligands according to claims 8-9 of at least 4:1 is established, d) a molar ratio of phosphorus-containing organic ligands according to claims 8-9 to rhodium of at least 10:1 is established.
    Type: Grant
    Filed: September 27, 2011
    Date of Patent: April 28, 2015
    Assignee: Evonik Oxeno GmbH
    Inventors: Robert Franke, Nicole Brausch, Dirk Fridag, Andrea Christiansen, Marc Becker, Peter Wasserscheid, Marco Haumann, Michael Jakuttis, Sebastian Werner, Andreas Schoenweiz
  • Patent number: 8859815
    Abstract: A diamine of formula (I) is described in which A is hydrogen or a saturated or unsaturated C1-C20 alkyl group or an aryl group; B is a substituted or unsubstituted C1-C20 alkyl, cycloalkyl, alkaryl, alkaryl or aryl group or an alkylamino group and at least one of X1, X2, Y1, Y2 or Z is a C1-C10 alkyl, cycloalkyl, alkaryl, aralkyl or alkoxy substituting group. The chiral diamine may be used to prepare catalysts suitable for use in transfer hydrogenation reactions.
    Type: Grant
    Filed: December 7, 2011
    Date of Patent: October 14, 2014
    Assignee: Bial-Portela & C.A., S.A.
    Inventors: Beatriz Dominguez, Antonio Zanotti-Gerosa, Gabriela Alexandra Grasa, Jonathan Alan Medlock
  • Patent number: 8816113
    Abstract: A novel bidentate catalytic ligand of general formula (I) is described. R represents a hydrocarbyl aromatic structure having at least one aromatic ring to which Q1 and Q2 are each linked, via the respective linking group, if present, on available adjacent atoms of the at least one aromatic ring. The groups X3 and X4 represent radicals joined via tertiary carbon atoms to the respective atom Q1 and the groups X1 and X2 represent radicals joined via primary, or substituted aromatic ring carbon atom(s) to the respective atom Q2. A and B represent an optional lower alkylene linking group. Q1 and Q2 each represent phosphorus, arsenic or antimony. A process for the carbonylation of ethylenically unsaturated compounds comprising reacting the compound with carbon monoxide in the presence of a source of hydroxyl groups, optionally, a source of anions and catalyst system obtainable by combining a metal of Group 8, 9 or 10 or a compound thereof and the bidentate ligand of general formula (I) is also described.
    Type: Grant
    Filed: July 2, 2009
    Date of Patent: August 26, 2014
    Assignee: Lucite International UK Limited
    Inventors: Graham Ronald Eastham, Mark Waugh, Paul Pringle, Tamara Fanjul Solares
  • Patent number: 8791305
    Abstract: The present invention relates to ligands and catalyst systems for the hydroformylation of short and long chain olefins, preferably for the hydroformylation of ally alcohol producing 4-hydroxybutyraldehyde. The ligands disclosed herein are all-trans phosphinomethyl-cyclobutane ligands, such as, for example, all-trans-1,2,3,4-tetra[bis-(3,5-xylyl)phosphinomethyl]-cyclobutane. The catalyst systems comprise these all-trans phosphinomethyl-cyclobutane ligands in combination with an organometallic rhodium complex such as, e.g., (acctylacetonato)-dicarbonyl-rhodium (I). The ligands and catalyst systems of the present invention may be employed in the hydroformylation of olefins, in particular in the hydroformylation of allylalcohol, and provide improved selectivity and high reaction yields.
    Type: Grant
    Filed: May 25, 2012
    Date of Patent: July 29, 2014
    Assignee: Umicore AG & Co. KG
    Inventor: Dieter Arlt
  • Patent number: 8710276
    Abstract: Disclosed are a catalyst composition for hydroformylation of olefin compounds, comprising a specific phosphine ligand and a transition metal catalyst, and a hydroformylation process using the same. Through a hydroformylation process using the catalyst composition according to the present invention, a suitable selectivity of iso-aldehyde can be maintained, catalyst stability can be improved, the amount of used ligand can be reduced and superior catalyst activity can be obtained.
    Type: Grant
    Filed: July 24, 2013
    Date of Patent: April 29, 2014
    Assignee: LG Chem, Ltd.
    Inventors: Dong Hyun Ko, Sung Shik Eom, O Hak Kwon, Hye Won Yang, Jae Hui Choi
  • Publication number: 20140114090
    Abstract: The present invention relates to ligands and catalyst systems for the hydroformylation of short and long chain olefins, preferably for the hydroformylation of ally alcohol producing 4-hydroxybutyraldehyde. The ligands disclosed herein are all-trans phosphinomethyl-cyclobutane ligands, such as, for example, all-trans-1,2,3, 4-tetra[bis-(3,5-xylyl)phosphinomethyl]-cyclobutane. The catalyst systems comprise these all-trans phosphinomethyl-cyclobutane ligands in combination with an organometallic rhodium complex such as, e.g., (acctylacetonato)-dicarbonyl-rhodium (I). The ligands and catalyst systems of the present invention may be employed in the hydroformylation of olefins, in particular in the hydroformylation of allylalcohol, and provide improved selectivity and high reaction yields.
    Type: Application
    Filed: May 25, 2012
    Publication date: April 24, 2014
    Applicant: UMICORE AG & CO. KG
    Inventor: Dieter Arlt
  • Publication number: 20130289313
    Abstract: The present invention provides a composition comprising: a) an inert porous support material, b) an ionic liquid, c) a metal selected from group 9 of the Periodic Table of the Elements, d) a phosphorus-containing organic ligand, e) at least one organic amine. The present invention further provides a process for hydroformylating olefin-containing hydrocarbon mixtures to aldehydes with addition of the inventive composition as a catalytically active composition, wherein: a) the water content of the olefin-containing hydrocarbon mixture is adjusted to not more than 20 ppm, b) the content of polyunsaturated compounds in the olefin-containing hydrocarbon mixture is adjusted to not more than 3000 ppm, c) a molar ratio of organic amines according to claims 10-13 to phosphorus-containing organic ligands according to claims 8-9 of at least 4:1 is established, d) a molar ratio of phosphorus-containing organic ligands according to claims 8-9 to rhodium of at least 10:1 is established.
    Type: Application
    Filed: September 27, 2011
    Publication date: October 31, 2013
    Applicant: EVONIK OXENO GmbH
    Inventors: Robert Franke, Nicole Brausch, Dirk Fridag, Andrea Christiansen, Marc Becker, Peter Wasserscheid, Marco Haumann, Michael Jakuttis, Sebastian Werner, Andreas Schoenweiz
  • Patent number: 8546570
    Abstract: A process is described for the synthesis of a cationic [rhodium diolefin phosphorus ligand] complex comprising the steps of: (a) reacting a rhodium-diolefin-1,3-diketonate and an acid in a ketone solvent, (b) adding a stabilising olefin to form a stabilised cationic rhodium compound, and (c) mixing a phosphorus ligand with the solution of the stabilised cationic rhodium compound to form a solution of the cationic [rhodium diolefin phosphorus ligand] complex. The solution may be used directly or the complex recovered. In one embodiment, the solution may be combined with a co-solvent and the ketone removed to give a new catalyst solution, from which the complex may be recovered.
    Type: Grant
    Filed: July 2, 2009
    Date of Patent: October 1, 2013
    Assignee: Johnson Matthey Public Limited Co.
    Inventor: Hans Guenter Nedden
  • Patent number: 8492593
    Abstract: Amido-fluorophosphite compounds and catalyst systems comprising at least one amido-fluorophosphite ligand compound in combination with a transition metal are described. Moreover, the use of amido-fluorophosphite containing catalysts for transition metal catalyzed processes, especially to the hydroformylation of various olefins to produce aldehydes are also described.
    Type: Grant
    Filed: August 16, 2011
    Date of Patent: July 23, 2013
    Assignee: Eastman Chemical Company
    Inventor: Thomas Allen Puckette
  • Patent number: 8481735
    Abstract: [Problem] The present invention aims to provide a novel organometallic compound that can be used as a general-use highly active catalyst with superior selectivity for functional groups. [Means for Solving Problem] The present invention relates to an organometallic compound having a novel specific structure of general formula (1): and to a general-use highly active catalyst used in reductive amination reaction with superior selectivity for functional groups that comprises said organometallic compound, and to a process for preparing amine compounds by reductive amination reaction using said catalyst.
    Type: Grant
    Filed: March 12, 2010
    Date of Patent: July 9, 2013
    Assignee: Kanto Kagaku Kabushiki Kaisha
    Inventors: Masahito Watanabe, Junichi Hori, Kunihiko Murata
  • Patent number: 8395003
    Abstract: The object of this invention is a suspension of metal nanoparticles with a mean size of between 1 and 20 nanometers, in at least one non-aqueous ionic liquid, whereby said suspension also contains at least one nitrogen-containing ligand, in which said metal nanoparticles comprise at least one transition metal in the zero valence state that is selected from among rhodium, ruthenium, iridium, nickel, and platinum by themselves or in a mixture and in which said nitrogen-containing ligand is selected from the group that is formed by the linear compounds that comprise at least one nitrogen atom, whereby the non-aromatic cyclic compounds comprise at least one nitrogen atom, the non-condensed aromatic compounds comprise at least one nitrogen atom, the condensed aromatic compounds comprise at least one group of two aromatic cycles that are condensed two by two, and at least one nitrogen atom, whereby the condensed aromatic compounds comprise at least 3 aromatic cycles and 1 nitrogen atom, and whereby the condensed ar
    Type: Grant
    Filed: April 14, 2008
    Date of Patent: March 12, 2013
    Assignee: IFP Energies Nouvelles
    Inventors: Bastien Leger, Alain Roucoux, Helene Olivier-Bourbigou
  • Publication number: 20130046112
    Abstract: Amido-fluorophosphite compounds and catalyst systems comprising at least one amido-fluorophosphite ligand compound in combination with a transition metal are described. Moreover, the use of amido-fluorophosphite containing catalysts for transition metal catalyzed processes, especially to the hydroformylation of various olefins to produce aldehydes are also described.
    Type: Application
    Filed: August 16, 2011
    Publication date: February 21, 2013
    Applicant: Eastman Chemical Company
    Inventor: Thomas Allen Puckette
  • Publication number: 20120322652
    Abstract: An exhaust gas purifying catalyst includes: rhodium; a zirconium-containing oxide which supports rhodium, and comprises: at least one element selected from the group consisting of calcium, lanthanum, cerium, neodymium and yttrium; and zirconium; and a NOx absorbing material comprising at least one selected from the group consisting of magnesium, barium, sodium, potassium and cesium. A degree of dispersion of rhodium is 20% or more after baking at 900° C. in air for three hours. A method for manufacturing the exhaust gas purifying catalyst includes: mixing the zirconium-containing oxide with water, thereby preparing an aqueous liquid of the zirconium-containing oxide; and supporting rhodium on the zirconium-containing oxide by mixing the aqueous liquid of the zirconium-containing oxide with an aqueous solution of a rhodium salt. A pH of a mixed liquid of the aqueous solution of the rhodium salt and the aqueous liquid of the zirconium-containing oxide is adjusted to 7 or more.
    Type: Application
    Filed: August 23, 2012
    Publication date: December 20, 2012
    Inventors: Tetsuro Naito, Masanori Nakamura, Hironori Wakamatsu
  • Publication number: 20120252662
    Abstract: The invention relates to nitrogen-doped carbon nanotubes (NCNT), the surface of which is charged with metal nanoparticles, and to a method for the production thereof and use thereof as a catalyst.
    Type: Application
    Filed: December 14, 2010
    Publication date: October 4, 2012
    Applicant: BAYER INTELLECTUAL PROPERTY GMBH
    Inventors: Jens Assmann, Aurel Wolf, Leslaw Mleczko, Oliver Felix-Karl Schlueter
  • Patent number: 8217204
    Abstract: This invention aims at providing a catalyst for producing an optically active aldehyde or an optically active ketone, which is an optically active carbonyl compound, by carrying out selective asymmetric hydrogenation of an ?,?-unsaturated carbonyl compound, particularly a catalyst which is insoluble in a reaction mixture for obtaining optically active citronellal which is useful as a flavor or fragrance, by carrying out selective asymmetric hydrogenation of citral, geranial or neral; and a method for producing a corresponding optically active carbonyl compound.
    Type: Grant
    Filed: June 2, 2010
    Date of Patent: July 10, 2012
    Assignee: Takasago International Corporation
    Inventors: Hironori Maeda, Yoji Hori
  • Publication number: 20120022252
    Abstract: The disclosure is directed to: (a) phosphacycle ligands; (b) methods of using such phosphacycle ligands in bond forming reactions; and (c) methods of preparing phosphacycle ligands.
    Type: Application
    Filed: July 15, 2011
    Publication date: January 26, 2012
    Applicant: ABBOTT LABORATORIES
    Inventors: Shashank Shekhar, Thaddeus S. Franczyk, David M. Barnes, Travis B. Dunn, Anthony R. Haight, Vincent S. Chan
  • Patent number: 8092720
    Abstract: Polymer supported metal complex catalysts and methods of their preparation and use are described. The polymer supported metal complex catalysts can be obtained via ligand exchange reactions between polymer ligands and a metal complex having catalytic activity. For example, a polymer supported rhodium (II) complex catalyst can be prepared via ligand exchange reaction between an insoluble polymer and a rhodium (II) carboxylate complex, wherein the insoluble polymer is prepared by a copolymerization reaction of (i) a styrene derivative with a substituted carboxylic acid, (ii) a styrene, and (iii) a linear alkane with both ends substituted by vinylbenzyloxy groups. The polymer supported catalysts can be used to catalyze asymmetric carbene reactions such as C—H insertion reactions and the like with high catalytic activity, chemical selectivity, diastereoselectivity, and enantioselectivity.
    Type: Grant
    Filed: June 20, 2007
    Date of Patent: January 10, 2012
    Assignee: National University Corporation Hokkaido University
    Inventors: Shunichi Hashimoto, Masahiro Anada
  • Patent number: 8008529
    Abstract: Ligands of the formula (I) secondary phosphine-Q-P(?O)HR1 (I) in the form of mixtures of diastereomers or pure diastereomers, in which secondary phosphine is a secondary phosphine group with hydrocarbon radicals or heterohydrocarbon radicals as substituents; Q is a bivalent bisaryl or bisheteroaryl radical with an axial chiral centre to which the two phosphorus atoms are bonded in the ortho positions to the bisaryl or bisheteroaryl bridge bond, or Q is a bivalent ferrocenyl radical with a planar chiral centre or without a planar chiral centre, to which the phosphorus atom of the secondary phosphine is bonded directly or via a C1-C4-carbon chain to a cyclopentadienyl ring, the —P*(?O)HR1 group is bonded either on the same cyclopentadienyl ring in ortho position to the bonded secondary phosphine or on the other cyclopentadienyl ring; P* is a chiral phosphorus atom, and R1 is a hydrocarbon radical, a heterohydrocarbon radical or a ferrocenyl radical, where R1 is a ferrocenyl radical with a planar chiral centre w
    Type: Grant
    Filed: May 23, 2007
    Date of Patent: August 30, 2011
    Assignee: Solvias AG
    Inventors: Andreas Pfaltz, Yann Ribourdouille, Xiangdong Feng, Balamurugan Ramalingam, Benoît Pugin, Felix Spindler
  • Patent number: 7928267
    Abstract: Novel trivalent organophosphite ligands having the structure of general formula (I): wherein R is an alkyl or aryl group containing 1 to 30 carbon atoms; Ar1 and Ar2 are aryl groups containing 4 to 30 carbon atoms; R1 to R6 are H or alkyl or aryl hydrocarbon radicals containing 1 to 40 carbon atoms; and X is a connecting group or a simple chemical bond, were developed and found to be very active for hydroformylation processes for ethylenically unsaturated substrates. Catalyst solutions prepared from these ligands with a Rh metal show an unusual “ligand acceleration effect” for simple alkenes, i.e., the hydroformylation activity increases as the concentration of ligand increases, and are capable of producing linear or branched aldehydes under typical hydroformylation conditions.
    Type: Grant
    Filed: June 22, 2009
    Date of Patent: April 19, 2011
    Assignee: Eastman Chemical Company
    Inventors: Thomas Allen Puckette, Yun-Shan Liu
  • Patent number: 7872157
    Abstract: Novel trivalent organophosphonite ligands having the structure of general formula (I): wherein R is an alkyl or aryl group containing 1 to 30 carbon atoms; Ar1 and Ar2 are aryl groups containing 4 to 30 carbon atoms; R1 to R6 are H or alkyl or aryl hydrocarbon radicals containing 1 to 40 carbon atoms; and X is a connecting group or a simple chemical bond, were developed and found to be very active for hydroformylation processes for ethylenically unsaturated substrates. Catalyst solutions prepared from these ligands with a Rh metal show an unusual “ligand acceleration effect” for simple alkenes, i.e., the hydroformylation activity increases as the concentration of ligand increases, and are capable of producing linear or branched aldehydes under typical hydroformylation conditions.
    Type: Grant
    Filed: December 8, 2008
    Date of Patent: January 18, 2011
    Assignee: Eastman Chemical Company
    Inventors: Yun-Shan Liu, Jody Lee Rodgers
  • Patent number: 7872156
    Abstract: Novel fluorophosphite compounds having the structure of general formula (I): where Ar1 and Ar2 are aryl groups containing 4 to 30 carbon atoms; R1 to R6 are H or alkyl or aryl hydrocarbon radicals containing 1 to 40 carbon atoms; and X is a connecting group or a simple chemical bond, were developed and found to be very active for hydroformylation processes for ethylenically unsaturated substrates. Catalyst solutions prepared from these compounds with a Rh metal show an unusual “ligand acceleration effect” for simple alkenes, i.e., the hydroformylation activity increases as the concentration of ligand increases, and are capable of producing linear or branched aldehydes under typical hydroformylation conditions.
    Type: Grant
    Filed: December 8, 2008
    Date of Patent: January 18, 2011
    Assignee: Eastman Chemical Company
    Inventors: Yun-Shan Liu, Jody Lee Rodgers
  • Publication number: 20100324338
    Abstract: This invention aims at providing a catalyst for producing an optically active aldehyde or an optically active ketone, which is an optically active carbonyl compound, by carrying out selective asymmetric hydrogenation of an ?,?-unsaturated carbonyl compound, particularly a catalyst which is insoluble in a reaction mixture for obtaining optically active citronellal which is useful as a flavor or fragrance, by carrying out selective asymmetric hydrogenation of citral, geranial or neral; and a method for producing a corresponding optically active carbonyl compound.
    Type: Application
    Filed: June 2, 2010
    Publication date: December 23, 2010
    Applicant: TAKASAGO INTERNATIONAL CORPORATION
    Inventors: Hironori MAEDA, Yoji HORI
  • Publication number: 20100297724
    Abstract: The present invention provides a composite comprising at least one hydrophobic organic compound and a matrix of at least one metal; wherein said at least one hydrophobic compound is entrapped within said matrix, compositions comprising at least one composite and methods of its preparation.
    Type: Application
    Filed: May 20, 2010
    Publication date: November 25, 2010
    Applicant: YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM
    Inventors: David AVNIR, Raed ABU-REZIQ, Rachael BEN KNAZ, Itzik YOSEF, Guy NESHER, Gad MAROM
  • Publication number: 20100292514
    Abstract: A process for the production of 4-hydroxybutyraldehyde is described. The process comprises reacting allyl alcohol with a mixture of carbon monoxide and hydrogen in the presence of a solvent and a catalyst comprising a rhodium complex and a diphosphine. The diphoshine is a trans-1,2 -bis(bis(3,4-di-n-alkylphenyl)phosphinomethyl)cyclobutane and/or a 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis[bis(3,4-di-n-alkylphenyl)phosphino]butane. The process gives high yield of 4-hydroxybutyraldehyde compared to 3-hydroxy-2-methylpropionaldehyde.
    Type: Application
    Filed: May 13, 2009
    Publication date: November 18, 2010
    Inventor: Daniel F. White
  • Publication number: 20100191027
    Abstract: The object of this invention is a suspension of metal nanoparticles with a mean size of between 1 and 20 nanometers, in at least one non-aqueous ionic liquid, whereby said suspension also contains at least one nitrogen-containing ligand, in which said metal nanoparticles comprise at least one transition metal in the zero valence state that is selected from among rhodium, ruthenium, iridium, nickel, and platinum by themselves or in a mixture and in which said nitrogen-containing ligand is selected from the group that is formed by the linear compounds that comprise at least one nitrogen atom, whereby the non-aromatic cyclic compounds comprise at least one nitrogen atom, the non-condensed aromatic compounds comprise at least one nitrogen atom, the condensed aromatic compounds comprise at least one group of two aromatic cycles that are condensed two by two, and at least one nitrogen atom, whereby the condensed aromatic compounds comprise at least 3 aromatic cycles and 1 nitrogen atom, and whereby the condensed ar
    Type: Application
    Filed: April 14, 2008
    Publication date: July 29, 2010
    Applicant: IFP
    Inventors: Bastien-Thésards Leger, Alain Roucoux, Helene Oliver-Bourigou
  • Patent number: 7709411
    Abstract: Multicomponent nanoparticles include two or more dissimilar components selected from different members of the group of noble metals, base transition metals, alkali earth metals, and rare earth metals and/or different groups of the periodic table of elements. The two or more dissimilar components are dispersed using a polyfunctional dispersing agent such that the multicomponent nanoparticles have a substantially uniform distribution of the two or more dissimilar components. The polyfunctional dispersing agent may include organic molecules, polymers, oligomers, or salts of these. The molecules of the dispersing agent bind to the dissimilar components to overcome same-component attraction, thereby allowing the dissimilar components to form multicomponent nanoparticles. Dissimilar components such as iron and platinum can be alloyed together using the dispersing agent to form substantially uniform multicomponent nanoparticles, which can be used alone or with a support.
    Type: Grant
    Filed: April 9, 2009
    Date of Patent: May 4, 2010
    Assignee: Headwaters Technology Innovation, LLC
    Inventors: Bing Zhou, Sukesh Parasher, Michael Rueter
  • Patent number: 7691772
    Abstract: The present invention provides a method for producing a catalyst comprising the steps of: producing a metal salt solution containing salts of one or more metals; dispersing the metal salt solution, an organic matter and a porous carrier made of one or more metal oxides in a solvent to form a composite complex comprising one or more metal ions having 10 to 50,000 atoms, the organic matter bonded to the metal ions, and simultaneously make the composite complex carried on the porous carrier; and calcining the carrier having the composite complex carried thereon. The method may further comprise a step of reducing the metal ions on the porous carrier by reducing the carrier, after the step of making the composite complex carried on the carrier.
    Type: Grant
    Filed: March 22, 2005
    Date of Patent: April 6, 2010
    Assignee: Tanaka Kikinzoku Kogyo K.K.
    Inventor: Masayuki Saito
  • Publication number: 20100069679
    Abstract: Hydroformylation catalysts which can tolerate high levels of alkyne impurities in an olefin feed stream. The catalysts are composed of rhodium in combination with fluorophosphite ligands or rhodium in combination with certain bidentate ligands. Propionaldehyde has been produced by the hydroformylation of ethylene streams containing up to 1000 parts per million of acetylene without any loss of activity due to the presence of the acetylene. Ethylene contaminated with acetylene at 10,000 ppm can also be converted to propionaldehyde but some loss of activity occurs.
    Type: Application
    Filed: September 12, 2008
    Publication date: March 18, 2010
    Applicant: Eastman Chemical Company
    Inventor: Thomas A. Puckette
  • Patent number: 7674937
    Abstract: This invention is directed to a class of compounds that can be both monodentate and bidentate in their association with a transition metal to form a catalyst for reactions such as the hydroformylation of olefins to produce aldehydes. The compounds contain two phosphorus atoms having different steric and/or electronic nature. In hydroformylation catalysts, the compounds advantageously can produce a variable n/iso product mixture of aldehyde products that can be varied by simply changing process variables such as [H2]/[CO] partial pressure gas ratio or temperature/inert gas partial pressure.
    Type: Grant
    Filed: May 28, 2008
    Date of Patent: March 9, 2010
    Assignee: Eastman Chemical Company
    Inventors: Ginette Struck Tolleson, Thomas Allen Puckette
  • Publication number: 20090299099
    Abstract: This invention is directed to a class of compounds that can be both monodentate and bidentate in their association with a transition metal to form a catalyst for reactions such as the hydroformylation of olefins to produce aldehydes. The compounds contain two phosphorus atoms having different steric and/or electronic nature. In hydroformylation catalysts, the compounds advantageously can produce a variable n/iso product mixture of aldehyde products that can be varied by simply changing process variables such as [H2]/[CO] partial pressure gas ratio or temperature/inert gas partial pressure.
    Type: Application
    Filed: May 28, 2008
    Publication date: December 3, 2009
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Ginette Struck Tolleson, Thomas Allen Puckette
  • Patent number: 7612241
    Abstract: A process for the production of 4-hydroxybutyraldehyde is described. The process comprises reacting allyl alcohol with a mixture of carbon monoxide and hydrogen in the presence of a solvent and a catalyst system comprising a rhodium complex and a substituted or unsubstituted 4,5-bis(di-n-alkylphosphino)xanthene. The process gives high yield of 4-hydroxybutyraldehyde compared to 3-hydroxy-2-methylpropionaldehyde.
    Type: Grant
    Filed: March 23, 2009
    Date of Patent: November 3, 2009
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: Daniel F. White, Wilfred P. Shum, David John Cole-Hamilton
  • Patent number: 7601667
    Abstract: A sulfonate catalyst represented by the formula below and a ketone compound are placed in a solvent, and the ketone compound is hydrogenated by mixing in the presence of hydrogen to produce an optically active alcohol.
    Type: Grant
    Filed: March 10, 2006
    Date of Patent: October 13, 2009
    Assignees: Kanto Kagaku Kabushiki Kaisha, Nagoya Industrial Science Research Institute
    Inventors: Noriyuki Utsumi, Kunihiko Murata, Kunihiko Tsutsumi, Takeaki Katayama, Masahito Watanabe, Takeshi Ohkuma, Ryoji Noyori
  • Patent number: 7586010
    Abstract: Disclosed are catalyst solutions for preparing aldehydes with variable normal- to iso-aldehyde ratios comprising one or more phosphonite ligands, rhodium, and a hydroformylation solvent. Also disclosed is a process for preparing aldehydes with variable normal- to iso-aldehyde ratios comprising contacting an olefin, hydrogen, and carbon monoxide with one or more phosphonite ligands, rhodium, and a hydroformylation solvent. The phosphonite-based catalyst solutions provide the ability to manipulate the normal- to iso-aldehyde ratio by varying one or more process variables including carbon monoxide partial pressure, temperature, and gram moles ligand to gram atoms rhodium.
    Type: Grant
    Filed: November 16, 2007
    Date of Patent: September 8, 2009
    Assignee: Eastman Chemical Company
    Inventors: Yun-Shan Liu, Thomas Allen Puckette
  • Patent number: 7579294
    Abstract: A highly active and recyclable supported transition metal catalyst can be prepared by a simple process comprising mixing with heating a transition metal complex, a metal-chelating agent and an alkoxide of Ti, Al or Si, followed by treatment with water to induce a sol-gel reaction among the reactants.
    Type: Grant
    Filed: February 2, 2005
    Date of Patent: August 25, 2009
    Assignee: Postech Foundation
    Inventors: Jaiwook Park, Namdu Kim, Min Serk Kwon, Cheon Min Park
  • Publication number: 20090197760
    Abstract: The present invention relates to metallic catalysts containing nanoparticles of transition metals in particular of Co, Ru, Fe, Pd and Rh, disposed in pure ionic liquids or impregnated on supports that comprise zeolites, silicas, aluminas and oxides, forming catalytic systems, and to a method for preparation thereof.
    Type: Application
    Filed: January 23, 2009
    Publication date: August 6, 2009
    Applicant: PETROLEO BRASILEIRO S.A. - PETROBRAS
    Inventors: Jairton Dupont, Dagoberto Oliveira Silva, Flavio Andre Pavan, Giovanna Machado, Sergio Ribeiro Teixeira, Henrique Soares Cerqueira, Ana Carlota Belizario dos Santos, Eduardo Falabella Sousa Aguiar
  • Publication number: 20090171114
    Abstract: Ligands of the formula (I) secondary phosphine-Q-P(?O)HR1 (I) in the form of mixtures of diastereomers or pure diastereomers, in which secondary phosphine is a secondary phosphine group with hydrocarbon radicals or heterohydrocarbon radicals as substituents; Q is a bivalent bisaryl or bisheteroaryl radical with an axial chiral centre to which the two phosphorus atoms are bonded in the ortho positions to the bisaryl or bisheteroaryl bridge bond, or Q is a bivalent ferrocenyl radical with a planar chiral centre or without a planar chiral centre, to which the phosphorus atom of the secondary phosphine is bonded directly or via a C1-C4-carbon chain to a cyclopentadienyl ring, the —P*(?O)HR1 group is bonded either on the same cyclopentadienyl ring in ortho position to the bonded secondary phosphine or on the other cyclopentadienyl ring; P* is a chiral phosphorus atom, and R1 is a hydrocarbon radical, a heterohydrocarbon radical or a ferrocenyl radical, where R1 is a ferrocenyl radical with a planar chiral centre w
    Type: Application
    Filed: May 23, 2007
    Publication date: July 2, 2009
    Inventors: Andreas Pfaltz, Yann Ribourdouille, Xiangdong Feng, Balamurugan Ramalingam, Benoit Pugin, Felix Spindler
  • Publication number: 20090171122
    Abstract: Novel trivalent organophosphonite ligands having the structure of general formula (I): wherein R is an alkyl or aryl group containing 1 to 30 carbon atoms; Ar1 and Ar2 are aryl groups containing 4 to 30 carbon atoms; R1 to R6 are H or alkyl or aryl hydrocarbon radicals containing 1 to 40 carbon atoms; and X is a connecting group or a simple chemical bond, were developed and found to be very active for hydroformylation processes for ethylenically unsaturated substrates. Catalyst solutions prepared from these ligands with a Rh metal show an unusual “ligand acceleration effect” for simple alkenes, i.e., the hydroformylation activity increases as the concentration of ligand increases, and are capable of producing linear or branched aldehydes under typical hydroformylation conditions.
    Type: Application
    Filed: December 8, 2008
    Publication date: July 2, 2009
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Yun-Shan Liu, Jody Lee Rodgers
  • Publication number: 20090171121
    Abstract: Novel fluorophosphite compounds having the structure of general formula (I): where Ar1 and Ar2 are aryl groups containing 4 to 30 carbon atoms; R1 to R6 are H or alkyl or aryl hydrocarbon radicals containing 1 to 40 carbon atoms; and X is a connecting group or a simple chemical bond, were developed and found to be very active for hydroformylation processes for ethylenically unsaturated substrates. Catalyst solutions prepared from these compounds with a Rh metal show an unusual “ligand acceleration effect” for simple alkenes, i.e., the hydroformylation activity increases as the concentration of ligand increases, and are capable of producing linear or branched aldehydes under typical hydroformylation conditions.
    Type: Application
    Filed: December 8, 2008
    Publication date: July 2, 2009
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Yun-Shan Liu, Jody Lee Rodgers
  • Publication number: 20090156824
    Abstract: A method includes reacting an amino group, a composition including rhodium and an organic ligand, and a substrate having structural formula (I) in a reaction mixture. R1 is an organic group including a sp3 carbon atom bonded to CA. R2 is selected from the group consisting of hydrogen, methyl, and an organic group including a sp3 carbon atom bonded to CA. R3 and R4 independently are selected from the group consisting of hydrogen, methyl, and an organic group including a sp3 carbon atom bonded to CB. The method further includes forming a hydroaminated product in the reaction mixture.
    Type: Application
    Filed: October 14, 2008
    Publication date: June 18, 2009
    Applicant: BOARD OF TRUSTEES OF UNIVERSITY OF ILLINOIS
    Inventors: Akihiro Takemiya, Zhijian Liu, John F. Hartwig
  • Patent number: 7538235
    Abstract: A process for preparing an epoxidation catalyst comprising silver and a high-selectivity dopant on a support, which process comprises depositing a base having a pKb of at most 3.5 when measured in water at 25° C., on the support prior to depositing silver on the support, and depositing silver and a high-selectivity dopant on the support; the epoxidation catalyst; and a process for preparing an olefin oxide by reacting an olefin with oxygen in the presence of the epoxidation catalyst.
    Type: Grant
    Filed: March 31, 2005
    Date of Patent: May 26, 2009
    Assignee: Shell Oil Company
    Inventor: John Robert Lockemeyer
  • Patent number: 7462731
    Abstract: A process for the preparation of a compound of Formula (1): wherein: X is S, O or NR3, wherein R3 is H or an organic group; R is H or an organic group; R1 and R2 each independently are H, optionally substituted alkyl or optionally substituted aryl; G is a substituent; and n is 0 to 3: which comprises the steps: (a) reacting a compound of Formula (2) with a compound of Formula NHR1R2 to give a compound of Formula (3): wherein X, R, G and n are as defined above and R4 is optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl or a combination thereof; and (b) reducing the compound of Formula (3) to give a compound of Formula (1) is provided.
    Type: Grant
    Filed: September 12, 2003
    Date of Patent: December 9, 2008
    Assignee: NPIL Pharmaceuticals (UK) Limited
    Inventor: Ian Nicholas Houson
  • Publication number: 20080281128
    Abstract: Disclosed is a process for hydroformylation of ?-olefin wherein said ?-olefin is reached with carbon monoxide or carbon monoxide and hydrogen and/or a reducing agent in presence of a catalyst complex based on a rhodium precursor and a ligand mixture comprising at least 1% by weight of trphenylphosphine and at least 5% by weight of diphenylcyclohexylphosphine, tris-(o-tolyl)phosphine, tris-(p-tolyl)phosphine or (2-methyl-phenyl)diphenylphospine.
    Type: Application
    Filed: March 15, 2006
    Publication date: November 13, 2008
    Inventors: Esko Karvinen, Juha Lehtonen, Joni Kunnas, Merja Harteva
  • Publication number: 20080154067
    Abstract: Disclosed are catalyst solutions for preparing aldehydes with variable normal- to iso-aldehyde ratios comprising one or more phosphonite ligands, rhodium, and a hydroformylation solvent. Also disclosed is a process for preparing aldehydes with variable normal- to iso-aldehyde ratios comprising contacting an olefin, hydrogen, and carbon monoxide with one or more phosphonite ligands, rhodium, and a hydroformylation solvent. The phosphonite-based catalyst solutions provide the ability to manipulate the normal- to iso-aldehyde ratio by varying one or more process variables including carbon monoxide partial pressure, temperature, and gram moles ligand to gram atoms rhodium.
    Type: Application
    Filed: November 16, 2007
    Publication date: June 26, 2008
    Applicant: Eastman Chemical Company
    Inventors: Yun-Shan Liu, Thomas Allen Puckette
  • Patent number: 7385064
    Abstract: Disclosed are compounds having the following formula: in which Z11 is selected from a substituted or unsubstituted saturated adamantyl or other polycyclic group and a substituted or unsubstituted branched acyclic group containing at least 5 carbon atoms at least one of which is a tertiary carbon; and in which Z12 is a cyclic imide. Methods of using these compounds as chiral catalysts for carbenoid reactions and for enantioselective C—H aminations are also described.
    Type: Grant
    Filed: November 30, 2006
    Date of Patent: June 10, 2008
    Assignee: The Research Foundation of State University of New York
    Inventors: Huw M. L. Davies, Ravisekhara P. Reddy
  • Publication number: 20080081759
    Abstract: Disclosed are catalyst solutions for the hydroformylation of formaldehyde comprising one or more fluorophosphite compounds, rhodium and a hydroformylation solvent comprising at least one N,N-disubstituted amide, N-substituted cyclic amide, or a mixture thereof. Also disclosed are hydroformylation processes wherein formaldehyde is contacted with carbon monoxide, hydrogen one or more fluorophosphite compounds, rhodium and a hydroformylation solvent to produce glycolaldehyde. The fluorophosphite-based catalysts provide good reaction rates and high selectivity to glycolaldehyde.
    Type: Application
    Filed: August 15, 2007
    Publication date: April 3, 2008
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventor: Thomas Allen Puckette
  • Patent number: 7294602
    Abstract: A process for the production of 4-hydroxybutyraldehyde is described. The process comprises reacting allyl alcohol with a mixture of carbon monoxide and hydrogen in the presence of a solvent and a catalyst system comprising a rhodium complex and a trans-1,2-bis(bis(3,5-di-n-alkylphenyl)phosphinomethyl)-cyclobutane. The process gives high yield of 4-hydroxybutyraldehyde compared to 3-hydroxy-2-methylpropionaldehyde.
    Type: Grant
    Filed: August 3, 2007
    Date of Patent: November 13, 2007
    Assignee: Lyondell Chemical Technology, L.P.
    Inventor: Daniel F. White
  • Patent number: 7250526
    Abstract: A catalytic transfer hydrogenation process is provided. The catalyst employed in the process is a metal hydrocarbyl complex which is coordinated to defined bidentate ligands substituted with at least one group selected from an optionally substituted sulphonated hydrocarbyl group, a sulphonated perhalogenated hydrocarbyl group, or an optionally substituted sulphonated heterocyclyl group. Preferred metals include rhodium, ruthenium and iridium. Preferred bidentate ligands are diamines and aminoalcohols, particularly those comprising chiral centres. The hydrogen donor is advantageously a secondary alcohol or a mixture of triethylamine and formic acid. The process can be employed to transfer hydrogenate ketones and imines, which are preferably prochiral. Catalysts for use in such a process are also provided.
    Type: Grant
    Filed: November 29, 2001
    Date of Patent: July 31, 2007
    Assignee: NPIL Pharmaceuticals (UK) Limited
    Inventors: Andrew John Blacker, Christian Bubert, Jonathan Michael Jeremy Williams, Stephen Martin Brown
  • Patent number: 7217675
    Abstract: This invention relates to transition metal catalyst compounds represented by the formula: LMX2 wherein M is a Group 7 to 11 metal; L is a tridentate or tetradentate neutrally charged ligand that is bonded to M by least three or four nitrogen atoms, and at least one terminal nitrogen atom is part of a pyridinyl ring, a different terminal nitrogen atom is substituted with one C3–C50 hydrocarbyl, and one hydrogen atom or two hydrocarbyls; wherein at least one hydrocarbyl is a C3–C50 hydrocarbyl, and the central nitrogen atom is bonded to at least three different carbon atoms or two different carbon atoms, and one hydrogen atom; X is independently a monoanionic ligand or both X are joined together to form a bidentate dianionic ligand.
    Type: Grant
    Filed: March 17, 2004
    Date of Patent: May 15, 2007
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Gregory Adam Solan, Christopher James Davies
  • Patent number: 7176158
    Abstract: Copolymerization of Ni(H) or Co(II) acenaphthene diimine complexes containing olefinic substituents on aryl groups in the presence of a free radical initiator results in polymerized late transition metal catalysts which can be used for olefin polymerization or oligomerization. These catalysts have high catalyst activity for olefin polymerization or oligomerization.
    Type: Grant
    Filed: October 24, 2003
    Date of Patent: February 13, 2007
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Stanley Wai-Yan Chow, Guo-Xin Jin, Zerong Lin, Robert J. Wittenbrink, Dao Zhang
  • Patent number: 7148176
    Abstract: The present invention is directed to phosphine ligands and the use of such ligands in catalytic complexes with transition metals. The catalysts may be used in a variety of reactions and are especially useful for refining halogenoaromatics.
    Type: Grant
    Filed: July 27, 2001
    Date of Patent: December 12, 2006
    Assignee: Degussa AG
    Inventors: Matthias Beller, Wilhelm Hubert Ehrentraut, legal representative, Theresia Elisabeth Ehrentraut, legal representative, Christa Fuhrmann, Alexander Zapf, Andreas Ehrentraut, deceased