Iron, Cobalt, Nickel, Ruthenium, Rhodium, Palladium, Osmium, Iridium, Or Platinum Containing (fe, Co, Ni, Ru, Rh, Pd, Os, Ir Or Pt) Patents (Class 556/16)
  • Patent number: 9834572
    Abstract: The present invention relates to a process for preparing hydridocarbonyltris(triphenylphosphine)rhodium(I), RhH(CO)(PPh3)3, also referred to hereinafter as “Rh-hydrido.” An alcoholic suspension of triphenylphosphine is stirred with an Rh(III) chloride precursor at elevated temperature. The Rh(III) chloride precursor used may be rhodium(III) chloride hydrate RhCl3*xH2O or rhodium(III) chloride solution H3[RhCl6]*(H2O)n. After cooling, alcoholic alkali metal hydroxide solution is added, and the mixture is stirred for a few hours. Finally, sparging is effected with CO gas and the Rh-hydrido formed is removed. Rh-hydrido can be prepared by this process on the industrial scale with high yields and at very good quality.
    Type: Grant
    Filed: July 3, 2015
    Date of Patent: December 5, 2017
    Assignee: Umicore AG & Co. KG
    Inventors: Angelino Doppiu, Ralf Karch, Andreas Rivas-Nass, Eileen Woerner
  • Patent number: 9295983
    Abstract: The invention provides complexes in which a calixarene-related compound is coordinated to an iridium-containing metal colloid. The complexes can be immobilized on a substrate. The complexes of the invention are useful as tunable and highly robust isolated metal colloids that find use in binding of molecules and catalysis of chemical reactions.
    Type: Grant
    Filed: December 23, 2014
    Date of Patent: March 29, 2016
    Assignees: THE REGENTS OF THE UNIVERSITY OF CALIFORNIA, CHEVRON U.S.A. INC.
    Inventors: Alexander Katz, Namal De Silva, Andrew Solovyov, Alexander Kuperman, Cong-Yan Chen, Partha Nandi, Alexander Okrut, Igor Busygin
  • Patent number: 9243016
    Abstract: The present invention is directed to the synthesis of novel stable open metal clusters by selective oxidation of bound ligands. The synthesis comprises, for example, using an amine based oxidant for decarbonylation of specific carbonyl ligands. The synthesis can also comprise further removal of a bound amine group by an acid. The resulting metal cluster contains a coordinatively unsaturated site comprising a carbonyl vacancy. The resulting metal cluster can be used as a catalyst in a variety of chemical transformations.
    Type: Grant
    Filed: September 23, 2013
    Date of Patent: January 26, 2016
    Assignees: Chevron U.S.A. Inc., The Regents of the University of California
    Inventors: Alexander S. Katz, Alexander Kuperman, Alexander Okrut, Ron C. Runnebaum, Xiaoying Ouyang
  • Patent number: 9163045
    Abstract: The invention relates to a process for preparing diketonato-rhodium(I)-carbonyl complexes, especially diketonato-rhodium(I)-triorganophosphine-carbonyl complexes, for example Rh(CO)(PPh3)acac. The process according to the invention is a “one-pot synthesis” and features a process procedure without intermediate isolation stages. After introduction of an Rh(III) halide precursor into a solvent and sparging with carbon monoxide (CO), a diketo compound of the R?—C(?O)—CH2—C(?O)—R? type and a base are added, forming the intermediate compound diketonato-Rh(CO)2. After addition of a triorganophosphine of the PR3 type, the reaction mixture is heated and the diketonatocarbonyltriorganophosphine-rhodium(I) complex is removed. The process enables a rapid operation and a high yield. The complex Rh(CO)(PPh3)acac prepared in accordance with the invention, because of its purity, is particularly suitable as a catalyst or precatalyst for homogeneous catalysis, for example for hydroformylation reactions.
    Type: Grant
    Filed: April 25, 2013
    Date of Patent: October 20, 2015
    Assignee: UMICORE AG & CO. KG
    Inventors: Eileen Woerner, Timo Ebert, Ralf Karch, Andreas Rivas-Nass, Angelino Doppiu, Juergen Widmer
  • Publication number: 20150141685
    Abstract: The invention relates to a process for preparing diketonato-rhodium(I)-carbonyl complexes, especially diketonato-rhodium(I)-triorganophosphine-carbonyl complexes, for example Rh(CO)(PPh3)acac. The process according to the invention is a “one-pot synthesis” and features a process procedure without intermediate isolation stages. After introduction of an Rh(III) halide precursor into a solvent and sparging with carbon monoxide (CO), a diketo compound of the R?—C(?O)—CH2—C(?O)—R? type and a base are added, forming the intermediate compound diketonato-Rh(CO)2. After addition of a triorganophosphine of the PR3 type, the reaction mixture is heated and the diketonatocarbonyltriorganophosphine-rhodium(I) complex is removed. The process enables a rapid operation and a high yield. The complex Rh(CO)(PPh3)acac prepared in accordance with the invention, because of its purity, is particularly suitable as a catalyst or precatalyst for homogeneous catalysis, for example for hydroformylation reactions.
    Type: Application
    Filed: April 25, 2013
    Publication date: May 21, 2015
    Inventors: Eileen Woerner, Timo Ebert, Ralf Karch, Andreas Rivas-Nass, Angelino Doppiu, Juergen Widmer
  • Publication number: 20150101936
    Abstract: This invention relates to an iron-sulfur complex that is capable of efficiently catalyzing formation of hydrogen, and a method for producing hydrogen using the complex as a catalyst. The iron-sulfur complex provided herein comprises: a structure of formula (I) wherein the ligands L1 to L3, L5 and L6 and the groups X1 to X3 are each selected from the group consisting of alkyl, alkenyl, alkynyl and aryl that are substituted or unsubstituted, hydroxyl, carbonyl, aldehyde, and so on; L4 is a bridging ligand selected from the group consisting of hydroxyl, carbonyl, and so on; and the symbol “z” means the charge, which is an integer with the range of ?3 to +2. X1 and X2 may join together to form a bridging group between the two sulfur atoms. X3 may alternatively be a vacant site.
    Type: Application
    Filed: October 8, 2014
    Publication date: April 16, 2015
    Inventors: MING-HSI CHIANG, YU-CHIAO LIU, KAI-TI CHU
  • Publication number: 20150093890
    Abstract: A metal precursor and a method comprising decomposing a metal precursor on an integrated circuit device; and forming a metal from the metal precursor, wherein the metal precursor is selected from the group consisting of (i) a Co2(CO)6(R1C?CR2), wherein R1 and R2 are individually selected from a straight or branched monovalent hydrocarbon group have one to six carbon atoms that may be interrupted and substituted; (ii) a mononuclear cobalt carbonyl nitrosyl; (iii) a cobalt carbonyl bonded to one of a boron, indium, germanium and tin moiety; (iv) a cobalt carbonyl bonded to a mononuclear or binuclear allyl; and (v) a cobalt (II) complex comprising nitrogen-based supporting ligands.
    Type: Application
    Filed: September 27, 2013
    Publication date: April 2, 2015
    Inventors: James M. Blackwell, Scott B. Clendenning, John J. Plombon, Patricio E. Romero
  • Publication number: 20150065339
    Abstract: Catalysts prepared from abundant, cost effective metals, such as cobalt, nickel, chromium, manganese, iron, and copper, and containing one or more neutrally charged ligands (e.g., monodentate, bidentate, and/or polydentate ligands) and methods of making and using thereof are described herein. Exemplary ligands include, but are not limited to, phosphine ligands, nitrogen-based ligands, sulfur-based ligands, and/or arsenic-based ligands. In some embodiments, the catalyst is a cobalt-based catalyst or a nickel-based catalyst. The catalysts described herein are stable and active at neutral pH and in a wide range of buffers that are both weak and strong proton acceptors. While its activity is slightly lower than state of the art cobalt-based water oxidation catalysts under some conditions, it is capable of sustaining electrolysis at high applied potentials without a significant degradation in catalytic current. This enhanced robustness gives it an advantage in industrial and large-scale water electrolysis schemes.
    Type: Application
    Filed: July 2, 2014
    Publication date: March 5, 2015
    Inventors: Aaron J. Bloomfield, Stafford W. Sheehan, Samuel L. Collom, Robert H. Crabtree, Paul T. Anastas
  • Patent number: 8968599
    Abstract: A cholesteric liquid crystal. The liquid crystal includes a metal acetylide, of which the metal is a square, planar transition metal. The metal acetylide includes first and second acylphosphine ligands and first and second phenyl acetylene ligands. Each of the first and second phenyl acetylene ligands have a meta- or para-substituent, which are selected from the group consisting of H, F, CN, OCH3, C?C—C6H5,(COO—C34H50O2), and COO—C5H10—C))—C34H50O2.
    Type: Grant
    Filed: February 28, 2013
    Date of Patent: March 3, 2015
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Thomas M. Cooper, Ronald F. Ziolo, Aaron R. Burke, Anatoliy V. Glushchenko
  • Patent number: 8969607
    Abstract: The invention provides complexes in which a calixarene-related compound is coordinated to an iridium-containing metal colloid. The complexes can be immobilized on a substrate. The complexes of the invention are useful as tunable and highly robust isolated metal colloids that find use in binding of molecules and catalysis of chemical reactions.
    Type: Grant
    Filed: October 22, 2010
    Date of Patent: March 3, 2015
    Assignees: The Regents of the University of California, Chevron U.S.A., Inc.
    Inventors: Alexander Katz, Namal De Silva, Andrew Solovyov, Alexander Kuperman, Cong-Yan Chen, Partha Nandi, Alexander Okrut, Igor Busygin
  • Patent number: 8884044
    Abstract: The invention relates to ruthenium complexes which have a chiral diphosphorus donor ligand and in which the ruthenium has the oxidation state (+11) and the chiral diphosphorus donor ligand has bidentate P—P coordination to the ruthenium. The ruthenium complexes are present in two forms (cationic type A and uncharged type B), are cyclic and have a four- to six-membered ring incorporating the diphosphorus donor ligand. The chiral diphosphorus donor ligands are selected from the group consisting of diphosphines, diphospholanes, diphosphites, diphosphonites and diazaphospholanes. Furthermore, processes for preparing the ruthenium complexes of types A and B, which are based on ligand exchange reactions, are described. The Ru complexes are used as catalysts for homogeneous asymmetric catalysis for preparing organic compounds.
    Type: Grant
    Filed: March 26, 2009
    Date of Patent: November 11, 2014
    Assignee: Umicore AG & Co. KG
    Inventors: Andreas Rivas-Nass, Ralf Karch, Roland Winde, Angelino Doppiu, Tina Schneider
  • Publication number: 20140243526
    Abstract: The present invention relates to processes for the reduction by hydrogenation, using molecular H2, of a C5-C20 substrate containing one or two aldehydes functional groups into the corresponding alcohol or diol, characterized in that said process is carried out in the presence of —at least one catalyst or pre-catalyst in the form of a ruthenium complex having a coordination sphere of the N2P2O2, wherein the coordinating atoms N2 are provided by a first bidentate ligand, the coordinating atoms P2 are provided by a second bidentate ligand and the coordinating atoms O2 are provided by two non-linear carboxylate ligands; and —optionally of an acidic additive.
    Type: Application
    Filed: September 27, 2012
    Publication date: August 28, 2014
    Applicant: FIRMENICH SA
    Inventors: Philippe Dupau, Lucia Bonomo, Laurent Kermorvan
  • Patent number: 8716507
    Abstract: New hexa-coordinate iron (II) complexes comprising compounds of formula (I) are described. These compounds comprise a tetradentate ligand with donor atoms comprising nitrogen and phosphorus. These complexes are shown for the first time to be useful catalysts for the hydrogenation of ketones, aldehydes, or imines to produce alcohols or amines, and the asymmetric hydrogenation of prochiral ketones or imines to produce non-racemic alcohols or amines. The source of the hydrogen can be hydrogen gas or a hydrogen-donating molecule such as isopropanol or hydrogen-donating mixture such as formic acid and an amine depending on the structure of the catalyst. In certain embodiments, the axial ligands on the catalyst comprise organonitrile ligands, carbonyl ligands, isonitrile ligands, or combinations thereof. The catalysts and the preparation thereof are disclosed. A reaction using phosphine and diamine precursors that is templated by the iron ion is the preferred route to the catalysts.
    Type: Grant
    Filed: October 30, 2009
    Date of Patent: May 6, 2014
    Assignee: The Governing Council of University of Toronto
    Inventors: Alexandre Mikhailine, Friederike Freutel, Christine Sui-Seng, Nils Meyer, Robert H. Morris, Paraskevi Olympia Lagaditis
  • Publication number: 20140121427
    Abstract: The present invention is directed to the activation of metal carbonyl clusters by an oxidative agent to prepare a stable metal cluster catalyst exhibiting catalytic rate enhancement. The activation comprises, for example, using oxygen for decarbonylation of carbonyl ligands and changing the oxidation state of the other ligands. In one aspect, treatment of the metal cluster catalyst under oxidative conditions in a flow reactor leads to removal of CO ligands and oxidation of bound calixarene phosphine ligands, and results in a stable activated open metal cluster that is more active for ethylene hydrogenation catalysis. The resulting metal cluster contains coordinatively unsaturated sites comprising carbonyl vacancies. In one aspect, the resulting activated open metal cluster can be used as a catalyst in a variety of chemical transformations.
    Type: Application
    Filed: October 28, 2013
    Publication date: May 1, 2014
    Applicant: The Regents of the University of California
    Inventors: Alexander Katz, Ron C. Runnebaum, Alexander Okrut, Xiaoying Ouyang, Igor Busygin
  • Publication number: 20140088318
    Abstract: The present invention is directed to the synthesis of novel stable open metal clusters by selective oxidation of bound ligands. The synthesis comprises, for example, using an amine based oxidant for decarbonylation of specific carbonyl ligands. The synthesis can also comprise further removal of a bound amine group by an acid. The resulting metal cluster contains a coordinatively unsaturated site comprising a carbonyl vacancy. The resulting metal cluster can be used as a catalyst in a variety of chemical transformations.
    Type: Application
    Filed: September 23, 2013
    Publication date: March 27, 2014
    Applicants: THE REGENTS OF THE UNIVERSITY OF CALIFORNIA, CHEVRON U.S.A. INC.
    Inventors: Alexander S. Katz, Alexander Kuperman, Alexander Okrut, Ron C. Runnebaum, Xiaoying Ouyang
  • Patent number: 8592617
    Abstract: The present application is generally directed to ruthenium or osmium containing complexes and their use as redox mediators in electrochemical biosensors.
    Type: Grant
    Filed: December 21, 2006
    Date of Patent: November 26, 2013
    Assignee: Roche Diagnostics Operations, Inc.
    Inventors: Hugh Oliver Allen Hill, Christopher Paul Newman, Luet Lok Wong, Tai-Chu Lau
  • Patent number: 8592614
    Abstract: The present invention relates to new types of material mixtures composed of at least two substances, one serving as a matrix material and the other being an emission material capable of emission and containing at least one element of atomic number greater than 20, and for their use in organic electronic components such as electroluminescent elements and displays.
    Type: Grant
    Filed: July 7, 2004
    Date of Patent: November 26, 2013
    Assignee: Merck Patent GmbH
    Inventors: Heinrich Becker, Anja Gerhard, Philipp Stössel, Horst Vestweber
  • Publication number: 20130264216
    Abstract: The present disclosure relates generally to carbon to carbon coupling processes, and more specifically, to dimerization or trimerization by electrocatalysis of alkenes and alkynes at room temperature.
    Type: Application
    Filed: April 3, 2013
    Publication date: October 10, 2013
    Applicant: Ball State University Board of Trustees
    Inventors: Daesung Chong, Jesse W. Tye
  • Publication number: 20130244865
    Abstract: Provided is a catalyst for producing hydrogen, which catalyst has higher performance than conventional catalysts since, for example, it exhibits a certain high level of activity in an aqueous formic acid solution at high concentration even without addition of a solvent, amine and/or the like. The metal phosphine complex is a metal phosphine complex represented by General Formula (1): MHm(CO)Ln, wherein M represents an iridium, iron, rhodium or ruthenium atom; in cases where M is an iridium or rhodium atom, m=3 and n=2, and in cases where M is an iron or ruthenium atom, m=2 and n=3; and the number n of Ls each independently represent a tri-substituted phosphine represented by General Formula (2): PR1R2R3. The catalyst for producing hydrogen comprises the metal phosphine complex as a constituent component.
    Type: Application
    Filed: November 24, 2011
    Publication date: September 19, 2013
    Applicant: NATIONAL UNIVERSITY CORPORATION OKAYAMA UNIVERSITY
    Inventors: Makoto Muranaka, Toshiyuki Oshiki
  • Patent number: 8507705
    Abstract: The invention affords C2-symmetrical ruthenocene diphosphine ligands with surface chirality and their manufacture. The present invention uses (S)-(S)-1,1?-2(diphenylphosphino)-2,2?-2[(S)-4-isopropyloxazolinyl] ruthenocene as raw material and the product is prepared through two or three steps of reaction. At the action of trifluoroacetic acid, (S)-(S)-1,1?-2(diphenylphosphino)-2,2?-2[(S)-4-isopropyloxazolinyl] ruthenocene first removes oxazoline and gets ester amides compound which then carries out ester exchange or reduction alkylation and gets the product of ruthenocene diphosphine ligand with surface chirality. The ligands prepared with the structure as follows from the invention can be used in all kinds of metallic catalysis asymmetric reaction and has good reaction activity and stereoselectivity, wherein R is methyl or ethyl, R1 is linear or branched alkyl, cycloalkyl, alkoxy, aryl, aralkyl and alkyl amino.
    Type: Grant
    Filed: June 8, 2007
    Date of Patent: August 13, 2013
    Assignee: Shanghai Jiaotong University
    Inventors: Wanbin Zhang, Fang Xie, Delong Liu, Li Luo, Genghong Hua, Jian Shang
  • Patent number: 8487136
    Abstract: A method for selectively producing a monoaryl norbornene derivative represented by a formula (5) involves having a norbornadiene derivative represented by a formula (3) and a bromine compound represented by a formula (4) react with each other in the presence of a reducing agent, palladium and at least one selected from phosphorus compounds represented by the formulas (1) and (2), whereby the norbornene derivative represented by formula (5) having a monoaryl substituent is an exo configuration.
    Type: Grant
    Filed: July 29, 2008
    Date of Patent: July 16, 2013
    Assignee: Nippon Oil Corporation
    Inventors: Shinichi Komatsu, Toshikatsu Shoko, Tadahiro Kaminade
  • Patent number: 8455671
    Abstract: The invention relates to ruthenium complexes with a chiral ferrocenyldiphosphine ligand, wherein the ruthenium has the oxidation state (+II) and the chiral ferrocenyldiphosphine ligand has bidentate P—P coordination to the ruthenium. The ruthenium complexes are cyclic and with the ferrocenyldiphosphine ligand have an at least eight-membered ring. The ferrocenyldiphosphine ligands are selected from the group consisting of Taniaphos, Taniaphos-OH and Walphos ligands. A process for preparing the Ru complexes is described. The Rn complexes are used as catalysts for homogeneous asymmetric catalysis for preparing organic compounds.
    Type: Grant
    Filed: May 8, 2008
    Date of Patent: June 4, 2013
    Assignee: Umicore AG & Co. KG
    Inventors: Albrecht Salzer, Angelino Doppiu, Nadine Langenscheidt, Andreas Rivas-Nass, Ralf Karch, Roland Winde, Stefanie Mayrhofer
  • Patent number: 8362204
    Abstract: Described herein are methods for forming two or more dicarba bridges, as well as new compounds containing dicarba bridges.
    Type: Grant
    Filed: September 26, 2008
    Date of Patent: January 29, 2013
    Assignee: Syngene Limited
    Inventors: Andrea Robinson, Roy William Jackson, Jim Patel, Jomana Elaridi
  • Publication number: 20130018199
    Abstract: The invention provides complexes in which a calixarene-related compound is coordinated to an iridium-containing metal colloid. The complexes can be immobilized on a substrate. The complexes of the invention are useful as tunable and highly robust isolated metal colloids that find use in binding of molecules and catalysis of chemical reactions.
    Type: Application
    Filed: October 22, 2010
    Publication date: January 17, 2013
    Inventors: Alexander Katz, Namal De Silva, Andrew Solovyov, Alexander Kuperman, Cong-Yan Chen, Partha Nandi, Alexander Okrut, Igor Busygin
  • Publication number: 20110237814
    Abstract: The present invention relates to a ruthenium carbonyl complex that is represented by the following Formula (1): RuXY(CO)(L)??(1) (in the Formula (1), X and Y, which may be the same or different from each other, represent an anionic ligand and L represents a tridentate aminodiphosphine ligand which has two phosphino groups and a —NH— group), its production method, and a method for production of alcohols by hydrogenation-reduction of ketones, esters, and lactones using the complex as a catalyst. The ruthenium carbonyl complex of the invention has a high catalytic activity and it can be easily prepared and handled.
    Type: Application
    Filed: June 30, 2010
    Publication date: September 29, 2011
    Applicant: Takasago International Corporation
    Inventors: Wataru Kuriyama, Takaji Matsumoto, Yasunori Ino, Osamu Ogata
  • Publication number: 20110160474
    Abstract: The invention affords C2-symmetrical ruthenocene diphosphine ligands with surface chirality and their manufacture. The present invention uses (S)—(S)-1,1?-2(diphenylphosphino)-2,2?-2[(S)-4-isopropyloxazolinyl]ruthenocene as raw material and the product is prepared through two or three steps of reaction. At the action of trifluoroacetic acid, (S)—(S)-1,1?-2(diphenylphosphino)-2,2?-2[(S)-4-isopropyloxazolinyl]ruthenocene first removes oxazoline and gets ester amides compound which then carries out ester exchange or reduction alkylation and gets the product of ruthenocene diphosphine ligand with surface chirality. The ligands prepared with the structure as follows from the invention can be used in all kinds of metallic catalysis asymmetric reaction and has good reaction activity and stereoselectivity, wherein R is methyl or ethyl, R1 is linear or branched alkyl, cycloalkyl, alkoxy, aryl, aralkyl and alkyl amino.
    Type: Application
    Filed: June 8, 2007
    Publication date: June 30, 2011
    Applicant: SHANGHAI JIAOTONG UNIVERSITY
    Inventors: Wanbin Zhang, Fang Xie, Delong Liu, Li Luo, Genghong Hua, Jian Shang
  • Publication number: 20110003959
    Abstract: The invention relates to a coordination complex system comprising a ligand having the formula: R1—SO2—NH—P (XR2)2 (1a); or R1—SO2—N?PH (XR2)2 (1b); or R1—SO(OH)?N—P(XR2)2 (1c); wherein X is independently O, S, NH, or a bond; R1 and R2 are independently selected from hydrogen and substituted or unsubstituted alkyl or aryl; wherein at least one equivalent of the ligand is complexed to an equivalent of a metal selected from a transition metal and lanthanide. The invention also relates to the use of said coordination complexes as catalysts in the hydroformylation, hydrogenation, transfer hydrogenation, hydrocyanation, polymerization, isomerization, carbonylation, cross-coupling, metathesis, CH activation, allylic substitution, aldol condensation, or Michael addition.
    Type: Application
    Filed: November 19, 2008
    Publication date: January 6, 2011
    Inventors: Joost Nikolaas Hendrik Reek, Frederic William Patureau, Mark Kuil, Albertus Jacobus Sandee, Jurjen Meeuwissen
  • Publication number: 20100145087
    Abstract: New hexa-coordinate iron (II) complexes comprising compounds of formula (I) are described. These compounds comprise a tetradentate ligand with donor atoms comprising nitrogen and phosphorus. These complexes are shown for the first time to be useful catalysts for the hydrogenation of ketones, aldehydes, or imines to produce alcohols or amines, and the asymmetric hydrogenation of prochiral ketones or imines to produce non-racemic alcohols or amines. The source of the hydrogen can be hydrogen gas or a hydrogen-donating molecule such as isopropanol or hydrogen-donating mixture such as formic acid and an amine depending on the structure of the catalyst. In certain embodiments, the axial ligands on the catalyst comprise organonitrile ligands, carbonyl ligands, isonitrile ligands, or combinations thereof. The catalysts and the preparation thereof are disclosed. A reaction using phosphine and diamine precursors that is templated by the iron ion is the preferred route to the catalysts.
    Type: Application
    Filed: October 30, 2009
    Publication date: June 10, 2010
    Applicant: The Governing Council of the University of Toronto
    Inventors: Alexandre MIKHAILINE, Friederike Freutel, Nils Meyer, Robert H. Morris, Parasekevi Olympia Lagaditis
  • Publication number: 20080269529
    Abstract: The invention relates to an enantiomerically enriched chiral compound comprising a transition metal M, which comprises four, five or six coordinating groups of which at least one pair is linked together to form a bidentate ligand, in which M is directly bound via one single ?-bond to a carbon atom of an optionally substituted and/or optionally fused (hetero)aromatic ring of said bidentate ligand and in which M is directly bound to a nitrogen atom of a primary or secondary amino group of said bidentate ligand, thereby forming a metallacycle between said bidentate ligand and the metal M, said metal M being selected from the metals of groups 8 and 9 of the Periodic Table of the Elements, in particular iron, ruthenium, osmium, cobalt, rhodium, or iridium. The chiral compound can be used as a catalyst, preferably in an asymmetric transfer hydrogenation process.
    Type: Application
    Filed: November 10, 2005
    Publication date: October 30, 2008
    Inventors: Johannes Gerardus (Hans) Vries De, Gerardus Karel Maria Verzijl, Andreas Hendrikus Maria Vries De, Vincent Ritleng, Adeline Marie Josephe Voelklin
  • Patent number: 7435840
    Abstract: The invention relates to compounds having a structural element of formula (I) in an aromatic hydrocarbon ring, wherein: M represents —Li, —MgX3, (C1-C18-Alkyl)3Sn—, —ZnX3 or —B(O—C1-C4-Alkyl)2; X1 and X2, independent of one another, represent O or N, and C-bound hydrocarbon radicals or heterohydrocarbon radicals are bound to the free bonds of the O and N atoms; group —C?C—, together with C atoms, forms a hydrocarbon aromatic compound and represents X3 Cl, Br or I. The inventive compounds are easily obtained by directly substituting the hydrogen in the ortho position to the P atom with metalation reagents. The metal atoms can then be substituted by a reactive electrophilic compound. The group —P(X1—)(X2—) - - - -(BH3)0,1 can then be converted into a secondary phosphine group. The inventive method enables the production of monophosphines and diphosphines even on a large scale, which are valuable ligands for metal complexes serving as catalysts for, e.g. enantioselective hydrogenations.
    Type: Grant
    Filed: December 10, 2004
    Date of Patent: October 14, 2008
    Assignee: Solvias AG
    Inventors: Andreas Pfaltz, Matthias Lotz, Marc Schönleber, Benoît Pugin, Martin Kesselgruber, Marc Thommen
  • Patent number: 7355057
    Abstract: The present invention relates to a series of platinum acetylide nonlinear optical chromophores which are liquid at room temperature. The viscosity of these liquid chromophores is low enough that they are easily processable into optical cells and can be used for nonlinear optical applications. The compounds remain liquids below room temperature, converting to a glass in the range of from about ?80° C. to ?100° C. Neat liquids have a high chromophore concentration (˜1 Mole/liter) making possible the development of optical devices requiring materials with a high chromophore concentration.
    Type: Grant
    Filed: November 17, 2004
    Date of Patent: April 8, 2008
    Inventors: Thomas M. Cooper, Benjamin C. Hall, Aaron R. Burke, Paul A. Fleitz
  • Patent number: 7348290
    Abstract: A novel polymer-supported arene-ruthenium complex represented by the following formula: , wherein A represents an organic polymer with a side chain containing an aromatic ring coordinated to Ru, X1 and X2 represent the same or different halogen atoms, and R represents a hydrocarbon group that may have a substituent is provided for use as a catalyst. This novel polymer-supported arene-ruthenium complex and catalyst thereof can be produced by a simple process, are stable and easy to recover, have a high catalytic activity, and can be used for various organic synthesis reactions. Novel methods for an organic synthesis reaction such as ring-opening metathesis reaction of an olefin compound and reduction of a carbonyl group, using the catalyst are provided.
    Type: Grant
    Filed: March 11, 2003
    Date of Patent: March 25, 2008
    Assignee: Japan Science and Technology Agency
    Inventor: Shu Kobayashi
  • Patent number: 7300639
    Abstract: A process is provided for removing one or more metals from liquids. Also provided is a process for the synthesis of aP2 inhibiting compounds having the formula (I) wherein R1, R2, R3, R4, HET, and X-Z are as described herein, which process comprising the step of removing one or more metals from a solution of the compound of formula I or an intermediate or precursor thereof. The processes for removing metal comprise the step of contacting the liquid with a solid extractant comprising a metal-binding functionality.
    Type: Grant
    Filed: December 2, 2003
    Date of Patent: November 27, 2007
    Assignee: Bristol-Myers Squibb Company
    Inventor: Wansheng Liu
  • Patent number: 7247595
    Abstract: A metallocene compound represented by the following Chemical Formula 1: wherein M is a transition metal of Group 4; Cp denotes a cyclopentadienyl ring unsubstituted or substituted by hydrogen, alkyl, cycloalkyl, aryl, alkenyl, alkylaryl, arylalkyl or arylalkenyl radicals; Qs, which are the same or different, are halogen radicals, alkyl, alkenyl, aryl, alkylaryl, or arylakyl radicals having 1 to 20 carbon atoms, or alkylidene radicals having 1 to 20 carbon atoms; A? is methoxymethyl, t-butoxymethyl, tetrahydropyranyl, tetrahydrofuranyl, 1-ethoxyethyl, 1-methyl-1-methoxyethyl, or t-butyl; and a is an integer of 4 to 8. The metallocene compounds in this invention can be strongly supported on the inorganic support, and the supported catalyst of this invention allows for an olefin polymerization process without any fouling in the reactor, and produces a polymer with better morphology and bulk density.
    Type: Grant
    Filed: November 30, 2005
    Date of Patent: July 24, 2007
    Assignee: LG Chem, Ltd.
    Inventors: Bun-Yeoul Lee, Jae-Seung Oh, Joo-Eun Lee, Do-Hoon Lee
  • Patent number: 7156731
    Abstract: A chiral compound, particularly a chiral secondary alcohol, can be efficiently resolved under a mild condition by acylation with an alkenyl acetate in the presence of a novel aminocyclopentadienyl ruthenium complex, an enzyme catalyst, and a base.
    Type: Grant
    Filed: May 17, 2002
    Date of Patent: January 2, 2007
    Assignee: Postech Foundation
    Inventors: Jaiwook Park, Mahn-Joo Kim, Jun Ho Choi, Yangsoo Ahn
  • Patent number: 7153809
    Abstract: Chiral ligands and metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The metal complexes according to the present invention are useful as catalysts in asymmetric reactions, such as, hydrogenation, hydride transfer, allylic alkylation, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, olefin metathesis, hydrocarboxylation, isomerization, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition; epoxidation, kinetic resolution and [m+n] cycloaddition. Processes for the preparation of the ligands are also described.
    Type: Grant
    Filed: January 7, 2005
    Date of Patent: December 26, 2006
    Assignee: The Penn State Research Foundation
    Inventors: Xumu Zhang, Wenjun Tang
  • Patent number: 7132491
    Abstract: Organometallic reversible addition-fragmentation chain transfer reagents (RAFT reagents), processes of free radical polymerization employing the same and polymers with low polydispersity index obtained thereby. The process includes polymerizing at least one monomer with at least one initiator and at least one organometallic RAFT reagent to obtain polymers having terminal organometallic functional groups with low polydispersity index. In addition, the terminal organometallic functional group may be removed by subjecting the obtained polymer to elimination to provide the corresponding organic polymers.
    Type: Grant
    Filed: May 10, 2004
    Date of Patent: November 7, 2006
    Assignee: Industrial Technology Research Institute
    Inventors: Yih-Hsing Lo, Kuo-Chen Shih, Yi-Chun Chen, Mei-Hua Wang, Fong Yee Hsu, Ming-Siao Hsiao
  • Patent number: 6987202
    Abstract: Phosphine compounds represented by the following formula (1): wherein R1, R2, R3, R4, R5, R6 and R7 represent substituents, and asymmetric synthesis catalysts containing transition metal phosphine complexes with the compounds contained as ligands therein. The novel phosphine compounds according to the present invention are useful especially as ligands in transition metal complexes. The transition metal phosphine complexes are useful as catalysts for asymmetric synthetic reactions. The novel phosphine compounds useful as ligands can be prepared by a relatively economical preparation process. Further, use of these catalysts can afford hydrogenated products with high optically purity and is also extremely useful from the industrial standpoint.
    Type: Grant
    Filed: November 6, 2003
    Date of Patent: January 17, 2006
    Assignee: Takasago International Corporation
    Inventors: Hideo Shimizu, Takao Saito, Izuru Nagasaki
  • Patent number: 6855657
    Abstract: 3,3?-Substituted chiral biaryl phosphine and phosphinite ligands and metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The metal complexes are useful as catalysts in asymmetric reactions, such as, hydrogenation, hydride transfer, allylic alkylation, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, olefin metathesis, hydrocarboxylation, isomerization, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition, epoxidation, kinetic resolution and [m+n] cycloaddition. The metal complexes are particularly effective in Ru-catalyzed asymmetric hydrogenation of beta-ketoesters to beta-hydroxyesters and Ru-catalyzed asymmetric hydrogenation of enamides to beta amino acids.
    Type: Grant
    Filed: September 11, 2003
    Date of Patent: February 15, 2005
    Assignee: The Penn State Research Foundation
    Inventor: Xumu Zhang
  • Publication number: 20040176622
    Abstract: A catalyst system containing a) Ni (0), b) 4-10 mol per mol Ni (0) according to a) a compound (I) of formula P (X1R1) (X2R2) (X3R3) (I) wherein X1, X2, X3 independently represent oxygen or a single bond R1, R2, R3 represent independently, the same or different organic radicals, and c) 1-4 mol per mol Ni (0) according to a) a compound (II) of formula (II) wherein X11, X12, X13, X21, X22, X23 independently oxygen or a single bond, R11, R12 independently represent the same or different individual or bridged organic radicals, R21, R22 independently represent the same or different, individual or bridged organic radicals, Y represents a bridge group.
    Type: Application
    Filed: January 20, 2004
    Publication date: September 9, 2004
    Inventors: Michael Bartsch, Robert Baumann, Dagmar Pascale Kunsmann-Keietel, Gerd Haderlein, Tim Jungkamp, Marco Altmayer, Wolfgang Seigel
  • Publication number: 20040171478
    Abstract: The present invention relates to a process for recovery of homogeneous metal hydride catalyst from a reactor stream as catalyst suitable for recycle to a reactor comprising the steps of: removing a stream from a reactor, said stream comprising the homogeneous metal hydride catalyst; contacting the stream with a solid acidic absorbent under process conditions which allow at least some of the metal to become bound to the absorbent; subjecting the metal bound to the absorbent, under process conditions which allow desorption of the metal, to a fluid stripping medium comprising hydrogen and solvent; and recovering the active metal hydride catalyst.
    Type: Application
    Filed: April 19, 2004
    Publication date: September 2, 2004
    Inventors: Simon Peter Crabtree, Robert Wild, Simon Wayne Jackson, James Andrew Banister
  • Publication number: 20040170547
    Abstract: A process is provided for removing one or more metals from liquids.
    Type: Application
    Filed: December 2, 2003
    Publication date: September 2, 2004
    Inventor: Wansheng Liu
  • Patent number: 6777567
    Abstract: Compounds of the formula (I) and (Ia) in the form of racemates, mixtures of diastereomers or in essentially enantiomerically pure form, (I), (Ia), where R is hydrogen, C1-C8alkyl, C5-C12cycloakyl, phenyl or phenyl substituted by from 1 to 3 C1-C4alky or C1-C4alkoxy groups; n is 0 or an integer from 1 to 4 and R1 are identical or different substituents selected from the group consisting of C1-C4alkyl, C1-C4fluoroalkyl and C1-C4alkoxy; X1 and X2 are each, independently of one another, secondary phosphino; T is C6-C20arylene or C3-C16heteroarylene; and X2 is bound in the ortho position relative to the T-cyclopentadienyl bond.
    Type: Grant
    Filed: December 31, 2002
    Date of Patent: August 17, 2004
    Assignee: Solvias AG
    Inventors: Walter Weissensteiner, Thomas Sturm, Felix Spindler
  • Patent number: 6750373
    Abstract: Disclosed is a new catalyst composition comprising a bimetallic Co—Fe catalyst, optionally complexed with a ligand selected from a N-heterocycle, phosphine, or porphorine ligand, that provides a lower cost alternative for the one step synthesis of 1,3-propanediol (1,3-PDO) from ethylene oxide and synthesis gas. For example, a catalyst containing cobalt carbonyl: iron carbonyl with no ligand, or a catalyst containing a cobalt carbonyl: octaethylporphine iron acetate provide moderate yields of 1,3-PDO in a one step synthesis under mild conditions.
    Type: Grant
    Filed: May 15, 2002
    Date of Patent: June 15, 2004
    Assignee: Shell Oil Company
    Inventors: John Frederick Knifton, Talmadge Gail James, Lynn Henry Slaugh, Kevin Dale Allen, Paul Richard Weider, Joseph Broun Powell
  • Patent number: 6743932
    Abstract: An organometallic compound of the formula I where M1 is selected from among Fe, Ru and Os and M2 is selected from among the transition metals of groups IV to VI of the Periodic Table, which can be prepared by reacting an organometallic compound of the formula II with a transition metal compound of the formula III, M2L1L2(L3)x+1  III where the variables are as defined above and the organometallic compound of the formula II can, if desired, be doubly deproteinated beforehand, can be used as part of a catalyst system for the polymerization or copolymerization of olefins. This catalyst system comprises one or more organometallic compounds of the formula I and at least one activator.
    Type: Grant
    Filed: April 6, 2001
    Date of Patent: June 1, 2004
    Assignee: Basell Polyolefine GmbH
    Inventors: Marc Oliver Kristen, Benno Bildstein, Michael Malaun, Ulrich Siemeling, Oliver Kuhnert
  • Publication number: 20040097672
    Abstract: The invention concerns a catalyst for olefin polymerisation, of formula (I) wherein: E is an oxygen or sulphur atom; X is a phosphorus, arsenic or antimony atom; M is a nickel, palladium or platinum atom comprising a non-attributed valency; a is 1 or 2; R1, R2, R3, identical or different can be selected among hydrogen, alkyl, cycloalkyl, aryl, alkylaryl, arylalkyl radicals, the hydroxyl radical, the alkoxide radicals (with 1 to 20 carbon atoms), the groups —C(O)OR′—, —SO3Y; and Z represents a hydrocarbon radical comprising 2 to 3 carbon atoms; R represents a hydrocarbon radical of valency a, provided that at least one of the radicals Z or R bears at least an electroattractive substituent.
    Type: Application
    Filed: July 10, 2003
    Publication date: May 20, 2004
    Inventors: Jerome Claverie, Remi Soula, Roger Spitz
  • Patent number: 6717018
    Abstract: A process for producing oxygenated products from an olefinic feedstock, which process includes reacting, in a hydroformylation reaction stage, an olefin feedstock with carbon monoxide and hydrogen at elevated temperature and superatmospheric pressure in the presence of a hydroformylation catalyst. The hydroformylation catalyst comprises a mixture of a metal, M, where M is cobalt (Co), rhodium (Rh), ruthenium (Ru) or palladium (Pd); carbon monoxide; and a bicyclic tertiary phosphine having a ligating phosphorus atom. The ligating phosphorus atom is neither in a bridgehead position nor a member of a bridge linkage. The process produces oxygenated products comprising aldehydes and/or alcohols.
    Type: Grant
    Filed: February 5, 2003
    Date of Patent: April 6, 2004
    Assignee: Sasol Technology (Proprietary) Limited
    Inventors: Jan Petrus Steynberg, Khedaren Govender, Petrus Johannes Steynberg
  • Patent number: 6664462
    Abstract: A metal complex having a &bgr;-diketonate represented by the following formula (1): wherein M represents a metal atom of the VIII group, R1, R2 and R3 represent a group or an atom selected from the group consisting of an alkyl group, an aryl group, a hydroxyl group, an amino group, an alkoxy group, a hydrogen atom and a halogen atom; X−1 represents an ion selected from a halogen, nitric acid, sulfonic acid, fluoroboric acid, fluorophosphoric acid, or perchloric acid ion; L1 or L2 represents a 2,2′-bipyridine or 1,10-phenanthroline group where these groups may be substituted with a group or an atom selected from an alkyl group, a carboxyl group, a sulfonic acid group, a phosphonic acid group, a hydroxyl group, an amino group, a hydrogen atom and a halogen atom. A photoelectric conversion element and a photochemical cell using the above-mentioned metal complex.
    Type: Grant
    Filed: November 13, 2001
    Date of Patent: December 16, 2003
    Assignee: National Institute of Advanced Industrial Science and Technology
    Inventors: Hironori Arakawa, Hideki Sugihara, Kohjiro Hara, Yoshiaki Takahashi
  • Patent number: 6660892
    Abstract: This invention is a process for synthesizing aliphatic 1,3-diols in one step by hydroformylation and hydrogenation of oxirane, carbon monoxide, and hydrogen employing a catalyst comprising a cobalt carbonyl compound and a cocatalyst metal compound ligated with a ligand in a ligand to cocatalyst metal atom molar ratio in the range of 0.2:1.0 to 0.6:1.0, optionally in the presence of a promoter, where recovery of product is preferably accomplished via water extraction of a diol rich phase from the bulk reaction mixture. The process modifications can, particularly in combination, be beneficial with respect to product recovery, catalyst recycle, and overall economics of a one-step process for producing aliphatic 1,3-diols.
    Type: Grant
    Filed: February 7, 2003
    Date of Patent: December 9, 2003
    Assignee: Shell Oil Company
    Inventors: Joseph Broun Powell, Paul Richard Weider, John Frederick Knifton, Kevin Dale Allen, Lynn Henry Slaugh, Juan Pedro Arhancet
  • Patent number: 6620342
    Abstract: The disclosure relates to a reversible, electrically controllable light transmission (RECLT) film, article of manufacture composition, process and product produced by the process, comprising a conductive narrow composition distribution polyvinylidene fluoride copolymer in combination with an electrolyte and an RECLT material. The narrow composition distribution polyvinylidene fluoride copolymer has low solubility, high thermal stability and strength, and very high optical clarity. The polyvinylidene fluoride copolymer comprises a nonporous or porous copolymer of vinylidene fluoride preferably with either hexafluoropropylene or tetrafluoroethylene or chlorotrifluoroethylene, or vinyl acetate, or combinations thereof. The RECLT material includes organic or inorganic compounds known in the art. Typical RECLT materials include electrochromic materials, reversible metal electrodeposition materials, liquid crystal materials and dispersed particle materials.
    Type: Grant
    Filed: October 23, 2000
    Date of Patent: September 16, 2003
    Assignee: Atofina Chemicals, Inc.
    Inventors: Michael Timothy Burchill, Marina M. Despotopoulou