Hydroformylation By Reacting Ethylenically Unsaturated Compound, Carbon Monoxide, And Gaseous Hydrogen Patents (Class 568/451)
  • Patent number: 5811589
    Abstract: Process for the preparation of a linear aldehyde organic compound by hydroformylation (b) starting from an internally unsaturated functionalised organic compound whereby first (a) a portion of the internally unsaturated functionalized organic compound is isomerized to a terminally unsaturated functionalised organic compound in the presence of a suitable isomerization catalyst, wherein following the isomerization step (a), the hydroformylation (b) is effected in the presence of carbon monoxide, hydrogen and a catalyst which preferentially catalyzes the hydroformylation reaction of the terminally unsaturated functionalised organic compound to the linear aldehyde organic compound, the internally unsaturated functionalised organic compound remaining practically unhydroformylated, whereupon (c) the linear aldhyde organic compound is separated out of the mixture and (d) the remainder of the unsaturated functionalised organic compound-containing mixture is recirculated to the isomerization step (a).
    Type: Grant
    Filed: November 3, 1995
    Date of Patent: September 22, 1998
    Assignee: DSM N.V.
    Inventors: Antonius J. J. M. Teunissen, Johannes G. De Vries, Onko J. Gelling, Cornelis Lensink
  • Patent number: 5808168
    Abstract: Waste gas obtained in the hydroformylation of olefinically unsaturated compounds in the presence of an aqueous catalyst solution comprising water-soluble rhodium complexes (1st reaction stage) is fed to a homogeneous reaction system in which residual amounts of the olefinically unsaturated compounds from the first reaction stage are reacted in a homogeneous reaction system (2nd reaction stage).
    Type: Grant
    Filed: April 17, 1997
    Date of Patent: September 15, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Bahrmann, Dieter Frohning, Wilhelm Gick, Wolfgang Hofs, Heinz Kalbfell, Harald Kappesser, Peter Lappe, Kurt Schalapski, Ernst Wiebus, Wolfgang Zgorzelski
  • Patent number: 5801291
    Abstract: The present invention relates to a process for the preparation of aldehydes, which comprises reacting an olefinic compound having 2 to 20 carbon atoms with carbon monoxide and hydrogen, in the presence or absence of a solvent, in the presence of a catalyst comprising rhodium and a compound or a mixture of compounds of the formula (I) ##STR1## in which R.sup.1 is H or an alkyl radical having 1 to 12 carbon atoms, R.sup.2 is a straight-chain alkylene radical having 1 to 8 carbon atoms, an oxygen-containing alkylene radical having 2 to 4 carbon atoms, a radical of the formula (II) or (III) ##STR2## or a cycloalkylene radical having 3 to 10 carbon atoms, R.sup.3 is an alkyl radical having 1 to 25 carbon atoms or an aryl radical having 6 to 10 carbon atoms, A is a radical --COO.sup.- or --SO.sub.3.sup.- and x=0, y=1, m=1 and n=1, or x=0.1, y=1, m=(1 or 2) and n=(1 or 2), or, if R.sup.2 is a radical of the formula (II) or (III), x=1, y=0, m=(0 or 1) and n=(0 or 1), at a temperature from 50.degree. to 190.degree. C.
    Type: Grant
    Filed: March 7, 1997
    Date of Patent: September 1, 1998
    Assignee: Hoechst AG
    Inventors: Helmut Bahrmann, Hans-Jerg Kleiner, Dieter Regnat
  • Patent number: 5789625
    Abstract: This invention relates to a process for separating one or more phosphorus acidic compounds from a reaction product fluid containing said one or more phosphorus acidic compounds, a metal-organophosphite ligand complex catalyst and optionally free organophosphite ligand which process comprises (a) treating said reaction product fluid with water sufficient to remove at least some amount of said one or more phosphorus acidic compounds from said reaction product fluid and (b) treating the water which contains phosphorus acidic compounds removed from said reaction product fluid with an acid removal substance sufficient to remove at least some amount of said one or more phosphorus acidic compounds from said water.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: August 4, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: David Robert Bryant, James Clair Nicholson
  • Patent number: 5786517
    Abstract: This invention relates to a process for separating one or more phosphorus acidic compounds from a reaction product fluid containing said one or more phosphorus acidic compounds, a metal-organophosphite ligand complex catalyst and optionally free organophosphite ligand which process comprises treating said reaction product fluid with water sufficient to remove at least some amount of said one or more phosphorus acidic compounds from said reaction product fluid.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: July 28, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: David Robert Bryant, James Clair Nicholson
  • Patent number: 5780684
    Abstract: The invention relates to a process for hydroformylating olefins with carbon monoxide and a hydrogen atom source in the presence of a catalyst system obtainable by combining (a) a source of a Group VIII metal cation, (b) a compound acting as bidentate ligand of the formula R.sup.1 R.sup.2 M.sup.1 --R--M.sup.2 R.sup.3 R.sup.4, wherein M.sup.1 and M.sup.2 independently are P, As or Sb, R represents a bivalent substituted or non-substituted bridging group containing from 1 to 5 atoms in the bridge, R.sup.1 and R.sup.2 together are a substituted or non-substituted bivalent group whereby the two free valencies are linked to M.sup.1, and R.sup.3 and R.sup.4 together are a substituted or non-substituted bivalent group whereby the two free valencies are linked to M.sup.2 or R.sup.3 and R.sup.4 independently are substituted or non-substituted hydrocarbyl groups, and (c) a source of anions; wherein the hydrogen atom source comprises water or a primary or secondary alcohol.
    Type: Grant
    Filed: January 15, 1997
    Date of Patent: July 14, 1998
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Willem Wabe Jager
  • Patent number: 5773667
    Abstract: A process for preparing aldehydes comprising hydroformylating olefinically unsaturated compounds with hydrogen and carbon monoxide in a homogeneous phase in the presence of a catalyst system comprising rhodium complex compounds and aromatic phosphines in a molar excess and separating off the catalyst system from the hydroformylation reaction mixture by pressure filtration on a semipermeable membrane of an aromatic polyamide by carrying out the hydroformylation at a pH of 2.5 to 4.3 using a molar ratio of phosphine:rhodium of at least 60 and at a rhodium concentration of at least 10 ppm by weight, based on the olefinically unsaturated compound used, and using, as aromatic phosphines, special alkylammonium and/or arylammonium salts of sulfonated or carboxylated triarylphosphines which process leads to excellent activities and selectivities in the hydroformylation step itself and also to high retention values in the membrane filtration step.
    Type: Grant
    Filed: May 14, 1997
    Date of Patent: June 30, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Bahrmann, Thomas Muller, Rainer Lukas
  • Patent number: 5773665
    Abstract: Active Rhodium catalyst and impurities are separated from a hydroformylation process stream containing both active and inactive organo-rhodium catalyst by binding active catalyst and impurities to an acidic ion exchange resin containing an acidic group. The purified hydroformylation stream can be returned to the hydroformylation reactor. All or a portion of inactive rhodium can be reactivated before recycling purified hydroformylation process stream to the reactor. During regeneration of the resin, a neutral solvent is used first to remove impurities which are discarded, then an acidic solvent is used to remove active organic rhodium catalyst from the resin. Such active catalyst can be rehydrided and returned to the hydroformylation reactor. An ion exchange resin having at least one acid group disposed on a silica backbone and an active organo-rhodium complex from a hydroformylation process stream bound to the resin can be produced.
    Type: Grant
    Filed: July 15, 1996
    Date of Patent: June 30, 1998
    Assignee: ELF Atochem North America, Inc.
    Inventors: Gary Stephen Silverman, Paul Mercando
  • Patent number: 5773666
    Abstract: Described is a process for hydroformylation of an olefinic compound, which comprises, carrying out the reaction in the presence of:a) a rhodium compound,b) a tertiary organic phosphorus compound represented by the following formula (1):P(X.sub.1)(X.sub.2)(X.sub.3 --SO.sub.3 M) (1)wherein X.sub.1 and X.sub.2 each independently represents a monovalent hydrocarbon group having 1-15 carbon atoms and X.sub.
    Type: Grant
    Filed: May 27, 1997
    Date of Patent: June 30, 1998
    Assignee: Kuraray Co., Ltd.
    Inventors: Toshihiro Omatsu, Jin Tokuyasu, Masahiro Muranaka, Takashi Onishi
  • Patent number: 5767321
    Abstract: This invention relates to a process which comprises reacting one or more reactants in the presence of a metal-organopolyphosphite ligand complex catalyst to produce a reaction product fluid comprising one or more products, wherein said process is conducted at a free organopolyphosphite ligand concentration sufficient to prevent and/or lessen hydrolytic degradation of the organopolyphosphite ligand and deactivation of the metal-organopolyphosphite ligand complex catalyst.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: June 16, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Ernst Billig, David Robert Bryant
  • Patent number: 5763671
    Abstract: This invention relates to a process for separating one or more phosphorus acidic compounds from a hydroformylation reaction product fluid containing said one or more phosphorus acidic compounds, a metal-organophosphite ligand complex catalyst and optionally free organophosphite ligand which process comprises (a) treating said hydroformylation reaction product fluid with water sufficient to remove at least some amount of said one or more phosphorus acidic compounds from said hydroformylation reaction product fluid and (b) treating the water which contains phosphorus acidic compounds removed from said hydroformylation reaction product fluid with an acid removal substance sufficient to remove at least some amount of said one or more phosphorus acidic compounds from said water.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: June 9, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: David Robert Bryant, James Clair Nicholson
  • Patent number: 5763679
    Abstract: This invention relates to a process which comprises reacting one or more reactants in the presence of a metal-organopolyphosphite ligand complex catalyst and optionally free organopolyphosphite ligand to produce a reaction product fluid comprising one or more products, wherein said process is conducted at a carbon monoxide partial pressure such that reaction rate increases as carbon monoxide partial pressure decreases and reaction rate decreases as carbon monoxide partial pressure increases and which is sufficient to prevent and/or lessen deactivation of the metal-organopolyphosphite ligand complex catalyst.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: June 9, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: James Clair Nicholson, David Robert Bryant, James Russell Nelson
  • Patent number: 5763678
    Abstract: An exothermic chemical reaction, for example, hydroformylation, is carried out in a series of loop reactors. Fresh reactant feed is supplied not only to the first reactor in the series but also to the second reactor, thereby achieving improved overall throughput while maintaining a stable temperature in at least the first reactor.
    Type: Grant
    Filed: May 1, 1996
    Date of Patent: June 9, 1998
    Assignee: Exxon Chemical Patents Inc
    Inventors: Hubertus Jozeph Beckers, Jan Martin De Rijke, Ronald Dean Garton
  • Patent number: 5763677
    Abstract: This invention relates to a process for separating one or more phosphorus acidic compounds from a hydroformylation reaction product fluid containing said one or more phosphorus acidic compounds, a metal-organophosphite ligand complex catalyst and optionally free organophosphite ligand which process comprises (a) treating said hydroformylation reaction product fluid with water sufficient to remove at least some amount of said one or more phosphorus acidic compounds from said hydroformylation reaction product fluid and (b) treating the water which contains phosphorus acidic compounds removed from said hydroformylation reaction product fluid with an ion exchange resin sufficient to remove at least some amount of said one or more phosphorus acidic compounds from said water.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: June 9, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: David Robert Bryant, James Clair Nicholson, Ernst Billig
  • Patent number: 5763680
    Abstract: This invention relates to a process for separating one or more phosphorus acidic compounds from a reaction product fluid containing said one or more phosphorus acidic compounds, a metal-organophosphite ligand complex catalyst and optionally free organophosphite ligand which process comprises (a) treating said reaction product fluid with water sufficient to remove at least some amount of said one or more phosphorus acidic compounds from said reaction product fluid and (b) treating the water which contains phosphorus acidic compounds removed from said reaction product fluid with an ion exchange resin sufficient to remove at least some amount of said one or more phosphorus acidic compounds from said water.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: June 9, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: David Robert Bryant, James Clair Nicholson, Ernst Billig
  • Patent number: 5763670
    Abstract: This invention relates to a hydroformylation process which comprises reacting one or more olefinic unsaturated compounds with carbon monoxide and hydrogen in the presence of a metal-organopolyphosphite ligand complex catalyst to produce a reaction product fluid comprising one or more aldehydes, wherein said hydroformylation process is conducted at a free organopolyphosphite ligand concentration sufficient to prevent and/or lessen hydrolytic degradation of the organopolyphosphite ligand and deactivation of the metal-organopolyphosphite ligand complex catalyst.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: June 9, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Ernst Billig, David Robert Bryant
  • Patent number: 5756838
    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: August 16, 1995
    Date of Patent: May 26, 1998
    Assignee: California Institute of Technology
    Inventors: Mark E. Davis, Kam To Wan
  • Patent number: 5756855
    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: August 19, 1994
    Date of Patent: May 26, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Anthony George Abatjoglou, David Robert Bryant, John Michael Maher
  • Patent number: 5744650
    Abstract: This invention relates to a process which comprises reacting one or more reactants in the presence of a metal-organopolyphosphite ligand complex catalyst and optionally free organopolyphosphite ligand to produce a reaction product fluid comprising one or more products, wherein said process is conducted at (a) a carbon monoxide partial pressure such that reaction rate increases as carbon monoxide partial pressure decreases and reaction rate decreases as carbon monoxide partial pressure increases and which is sufficient to prevent and/or lessen deactivation of the metal-organopolyphosphite ligand complex catalyst and (b) a temperature such that the temperature difference between reaction product fluid temperature and inlet coolant temperature is sufficient to prevent and/or lessen cycling of carbon monoxide partial pressure, hydrogen partial pressure, total reaction pressure, reaction rate and/or temperature during said process.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: April 28, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: James Clair Nicholson, David Robert Bryant, James Russell Nelson
  • Patent number: 5744649
    Abstract: This invention relates to a process for separating one or more phosphorus acidic compounds from a hydroformylation reaction product fluid containing said one or more phosphorus acidic compounds, a metal-organophosphite ligand complex catalyst and optionally free organophosphite ligand which process comprises treating said hydroformylation reaction product fluid with water sufficient to remove at least some amount of said one or more phosphorus acidic compounds from said hydroformylation reaction product fluid.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: April 28, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: David Robert Bryant, James Clair Nicholson
  • Patent number: 5741943
    Abstract: This invention relates to a hydroformylation process which comprises reacting one or more olefinic unsaturated compounds with carbon monoxide and hydrogen in the presence of a metal-organopolyphosphite ligand complex catalyst and optionally free organopolyphosphite ligand, and an amount of a sterically hindered organophosphorus ligand different from the organopolyphosphite ligand of said metal-organopolyphosphite ligand complex catalyst, to produce one or more aldehydes. The sterically hindered organophosphorus ligands are useful as indicators of organopolyphosphite ligand depletion in said hydroformylation process.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: April 21, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: David Robert Bryant, Tak Wai Leung
  • Patent number: 5741944
    Abstract: This invention relates to a process for separating one or more phosphorus acidic compounds from a hydroformylation reaction product fluid containing said one or more phosphorus acidic compounds, a metal-organophosphite ligand complex catalyst and optionally free organophosphite ligand which process comprises treating said hydroformylation reaction product fluid with an aqueous buffer solution sufficient to neutralize and remove at least some amount of said one or more phosphorus acidic compounds from said hydroformylation reaction product fluid.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: April 21, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: David Robert Bryant, Tak Wai Leung, Ernst Billig, Thomas Carl Eisenschmid, James Clair Nicholson
  • Patent number: 5741941
    Abstract: A process for preparing aldehydes by reacting straight-chain or branched olefins of at least 4 carbon atoms with carbon monoxide and hydrogen in the liquid phase in the presence of water, solubilizers and a catalyst system comprising water-soluble rhodium complexes, wherein the rhodium complexes present in the catalyst system contain specific sulfonated diphosphines as ligands and the solubilizers are quaternary ammonium salts.
    Type: Grant
    Filed: March 5, 1997
    Date of Patent: April 21, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Helmut Bahrmann
  • Patent number: 5741945
    Abstract: This invention relates to processes which comprise reacting one or more reactants in the presence of a metal-organopolyphosphite ligand complex catalyst and optionally free organopolyphosphite ligand, and an amount of a sterically hindered organophosphorus ligand different from the organopolyphosphite ligand of said metal-organopolyphosphite ligand complex catalyst, to produce one or more products. The sterically hindered organophosphorus ligands are useful as indicators of organopolyphosphite ligand depletion in said processes.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: April 21, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: David Robert Bryant, Tak Wai Leung
  • Patent number: 5741942
    Abstract: This invention relates to a process for separating one or more phosphorus acidic compounds from a reaction product fluid containing said one or more phosphorus acidic compounds, a metal-organophosphite ligand complex catalyst and optionally free organophosphite ligand which process comprises treating said reaction product fluid with an aqueous buffer solution sufficient to neutralize and remove at least some amount of said one or more phosphorus acidic compounds from said reaction product fluid.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: April 21, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: David Robert Bryant, Tak Wai Leung, Ernst Billig, Thomas Carl Eisenschmid, James Clair Nicholson
  • Patent number: 5731472
    Abstract: This invention relates to a method of stabilizing a metal-organopolyphosphite ligand complex catalyst against deactivation in a process which comprises reacting one or more reactants in the presence of a metal-organopolyphosphite ligand complex catalyst and optionally free organopolyphosphite ligand to produce a reaction product fluid comprising one or more products, which method comprises conducting said process in the presence of one or more free heterocyclic nitrogen compounds sufficient to prevent and/or lessen deactivation of the metal-organopolyphosphite ligand complex catalyst.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: March 24, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Tak Wai Leung, David Robert Bryant, Bernard Leslie Shaw
  • Patent number: 5731473
    Abstract: This invention relates to a process which comprises reacting one or more reactants in the presence of a metal-organophosphite ligand complex catalyst and dissolved water and optionally free organophosphite ligand to produce a reaction product fluid comprising one or more products, wherein said process is conducted in the presence of carbon dioxide in an amount sufficient not to effect substantial degradation of any said organophosphite ligand and/or substantial deactivation of said metal-organophosphite ligand complex catalyst.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: March 24, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: David Robert Bryant, James Clair Nicholson, Donald Leroy Bunning, Thomas Carl Eisenschmid, Donald Lee Morrison
  • Patent number: 5728893
    Abstract: This invention relates to a process for producing one or more products in a staged reactor having more than one reactive stage which process comprises reacting in said staged reactor one or more reactants with carbon monoxide in the presence of a metal-organophosphorus ligand complex catalyst and optionally free organophosphorus ligand to produce said one or more products, wherein said metal-organophosphorus ligand complex catalyst does not undergo substantial deactivation in the presence of solely carbon monoxide and/or effects a change in normal product selectivity of less than 0.2 percent of normal product per 1 pound per square inch of carbon monoxide partial pressure and/or effects a change in reaction rate of less than 2 percent per 1 pound per square inch of carbon monoxide partial pressure.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: March 17, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Michael Carl Becker, David Robert Bryant, Donald LeRoy Bunning, James Clair Nicholson, Ernst Billig
  • Patent number: 5723680
    Abstract: Aldehydes and/or alcohols are prepared by the hydroformylation of olefins of more than 3 carbon atoms by means of a bare rhodium catalyst dissolved homogeneously in the reaction medium, at superatmospheric pressure and at elevated temperatures, and separation of the rhodium catalyst from the liquid reaction mixture, by a process in which a magnetizable, inorganic pigment coated with a polymeric binder is used for separating the homogeneously dissolved, bare rhodium catalyst from the hydroformylation medium, and this pigment, after it has been laden with the rhodium contained in the hydroformylation medium, is separated from the liquid hydroformylation medium by applying an external magnetic field.
    Type: Grant
    Filed: April 18, 1997
    Date of Patent: March 3, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Claudius Kormann, Heinz-Josef Kneuper
  • Patent number: 5710344
    Abstract: The invention relates to a process for the preparation of linear aldehydes by hydroformylation of ethylenically unsaturated organic compounds in the presence of a catalyst system comprising a Group VIII metal and a bidentate organic ligand. The bidentate organic ligand is characterized in that it has two trivalent phosphorus atoms each containing at least one P--C or one P--N bond.
    Type: Grant
    Filed: November 8, 1996
    Date of Patent: January 20, 1998
    Assignees: E. I. Du Pont de Nemours and Company, DSM N.V.
    Inventors: Anne Irisa Breikss, Patrick M. Burke, James Michael Garner, Wilson Tam
  • Patent number: 5696297
    Abstract: Aldehydes or aldehydes and alcohols are prepared by hydroformylation of olefins of more than 3 carbon atoms by a process comprising the stage of hydroformylation by means of a rhodium catalyst homogeneously dissolved in the reaction medium, the separation of the rhodium catalyst from the discharge from the hydroformylation reaction and the recycling of the rhodium separated from the hydroformylation discharge to the hydroformylation stage, wherein the rhodium catalyst is extracted from the hydroformylation discharge into the aqueous phase by means of an aqueous solution of a water-soluble, phosphorus-containing complexing agent selected from the group consisting of the mono- or polysulfonated mono- and oligophosphines and/or from the group consisting of the mono- or polycarboxylated mono- or oligophosphines or the mono- or polysulfonated oligophosphites and the aldehyde or the aldehyde and the alcohol are isolated from the extracted hydroformylation discharge, the aqueous rhodium-containing extract is fed to
    Type: Grant
    Filed: August 2, 1995
    Date of Patent: December 9, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz-Josef Kneuper, Rocco Paciello, Michael Roper
  • Patent number: 5689010
    Abstract: Aldehydes with a higher number of carbon atoms and high selection are prepared by reacting olefins, in particular from petrochemical refinery products, by a hydroformylation with aldol condensation using a mixed catalyst of rhodium-carbonyl-phosphines and Mannich catalyst.
    Type: Grant
    Filed: April 29, 1996
    Date of Patent: November 18, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Rocco Paciello, Franz Merger, Michael Roper, Heinz-Josef Kneuper
  • Patent number: 5684208
    Abstract: In the process for hydroformylation of 1,3-butadiene with carbon monoxide and hydrogen to form pentenals, the improvement comprising effecting the hydroformylation with 1,3-butadiene dissolved in an inert reaction medium at 100.degree. to 180.degree. C. at 5 to 35 MPa in the presence of an aqueous solution of a rhodium/phosphine complex and optionally a further phosphine as catalyst.
    Type: Grant
    Filed: August 15, 1996
    Date of Patent: November 4, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Bahrmann, Peter Lappe, Ernst Wiebus, Bernhard Fell, Peter Hermanns
  • Patent number: 5663451
    Abstract: A process for the hydroformylation of olefins and olefinically unsaturated compounds in the presence of cobalt or rhodium complexes which contain, as complexing ligands, heterocyclic carbenes and, if desired, further ligands.
    Type: Grant
    Filed: December 29, 1995
    Date of Patent: September 2, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang A. Herrmann, Martina Elison, Jakob Fischer, Christian Kocher
  • Patent number: 5654491
    Abstract: A process for catalytic partial oxidation of a hydrocarbon is provided. The process includes: providing a feed gas mixture comprising an oxygen-containing gas and a hydrocarbon gas comprising one or more normal (C.sub.2 -C.sub.4)alkanes; providing a catalyst structure having a transparency of at least about 40%; and passing the feed gas mixture through the catalyst structure at a rate such that the superficial contact time of the feed gas mixture with the catalyst structure is no greater than about 1000 microseconds to produce an exit gas mixture comprising partial oxidation products.
    Type: Grant
    Filed: February 9, 1996
    Date of Patent: August 5, 1997
    Assignee: Regents of the University of Minnesota
    Inventors: Duane A. Goetsch, Lanny D. Schmidt
  • Patent number: 5648554
    Abstract: A method for producing aldehydes, which comprises reacting an olefinic unsaturated compound with carbon monoxide and hydrogen in a liquid phase in the presence of a Group 8 metal-phosphite complex catalyst, wherein a reaction product solution containing the complex catalyst and a high boiling by-product, obtained by the reaction, is intimately contacted with an extraction solution containing a polar solvent, to have either the complex catalyst or the high boiling by-product extracted selectively, followed by phase separation to separate a layer of the extraction solution from a layer of the reaction product solution.
    Type: Grant
    Filed: April 10, 1996
    Date of Patent: July 15, 1997
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Tomoyuki Mori, Masaki Takai, Tomohiko Inoue
  • Patent number: 5648553
    Abstract: A method for producing aldehydes, which comprises reacting an olefin with carbon monoxide and hydrogen in a hydroformylation reaction zone in the presence of a rhodium catalyst having an organophosphorus compound as a ligand, wherein a liquid mixture derived from an effluent from the hydroformylation reaction zone, which contains an unreacted olefin and aldehyde products, is heated and then supplied to a gas-liquid contact zone, where the heated liquid mixture is countercurrently contacted with carbon monoxide and hydrogen, and a gas stream of carbon monoxide and hydrogen containing an unreacted olefin is withdrawn from the gas-liquid contact zone to separate and recover the unreacted olefin, and the recovered unreacted olefin is supplied together with the carbon monoxide and the hydrogen to the hydroformylation reaction zone.
    Type: Grant
    Filed: November 8, 1995
    Date of Patent: July 15, 1997
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Akio Ueda, Masaki Nakagawa
  • Patent number: 5618983
    Abstract: A hydroformylation process for the production of linear aldehydes from linear olefins, by the reaction of the olefin with hydrogen and carbon monoxide in a solvent containing a catalyst having a platinum component or palladium component, a bidentate diaryl phosphine component where the bridging group is ferrocenyl or 3 to 6 carbon atoms, and a metal promoter component.
    Type: Grant
    Filed: August 25, 1995
    Date of Patent: April 8, 1997
    Assignees: E. I. Du Pont de Nemours and Company, DSM N. V.
    Inventor: Patrick M. Burke
  • Patent number: 5600031
    Abstract: A process for preparing oxo alcohols and aldehydes by the cobalt catalyzed hydroformylation of C.sub.2 to C.sub.17 linear or branched monoolefins with subsequent hydrogenation of the hydroformylation product, in which oxo process aqueous solutions of cobalt salts are converted to active hydrido cobalt carbonyl species in a preformer reactor under preforming reaction conditions, the improvement characterized by the preformer reactor containing a shell-type, metal on substrate, preformer catalyst.
    Type: Grant
    Filed: August 18, 1995
    Date of Patent: February 4, 1997
    Assignee: Exxon Chemical Patents, Inc.
    Inventor: Patricia B. Roussel
  • Patent number: 5585524
    Abstract: Method for the preparation of an aldehyde in a process in which cobalt is being recycled by:(a) hydroformylating of an ethylenically unsaturated compound with carbon monoxide and hydrogen at a pressure higher than 5 MPa and a temperature higher than 80.degree. C. in the presence of a cobalt carbonyl compound in an organic phase, following which(b) removing cobalt from the organic phase by contacting the organic phase with a polar mixture, which mixture is substantially immiscible with the organic phase, first the pressure being reduced to a pressure lower than 5 MPa and simultaneously or afterwards cooling being applied down to a temperature below 80.degree. C.
    Type: Grant
    Filed: June 23, 1995
    Date of Patent: December 17, 1996
    Assignee: DSM N.V.
    Inventors: Otto E. Sielcken, Nicolaas F. Haasen
  • Patent number: 5545767
    Abstract: 1,3-propanediol is prepared in a process comprising the steps of:contacting ethylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of an effective amount of a non-phosphine-ligated cobalt catalyst and an effective amount of a lipophilic phenol at a temperature within the range of about 50.degree. to about 100.degree. C. and a pressure within the range of about 500 to about 5000 psig, under reaction conditions effective to produce an intermediate product mixture comprising less than about 15 wt % 3-hydroxypropanal;adding an aqueous liquid to said intermediate product mixture and extracting into said aqueous liquid at a temperature less than about 100.degree. C.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: August 13, 1996
    Assignee: Shell Oil Company
    Inventors: Paul R. Weider, Joseph B. Powell, Lynn H. Slaugh, Thomas C. Forschner, Thomas C. Semple
  • Patent number: 5498801
    Abstract: A process is effected using water soluble metal complex catalysts in the presence of a promoter in the organic (water immiscible) phase. The process results in the enhancement of the rate of hydroformylation by interfacial catalysis induced by the presence of a ligand (promoter) in a catalyst immiscible phase. The reaction comprises of two phases viz - organic phase and aqueous phase. The organic phase consists of an olefin and P- containing water insoluble ligand with or without water immiscible solvent. The aqueous phase consists of a metal complex catalyst comprising of group VIII element such as Rh, Ru, Ir or Co and a water soluble ligand.
    Type: Grant
    Filed: December 30, 1994
    Date of Patent: March 12, 1996
    Assignee: Council of Scientific & Industrial Interest
    Inventors: Raghunath V. Chaudhari, Bhalchandra M. Bhanage, Sunil S. Divekar, Raj M. Deshpande
  • Patent number: 5491266
    Abstract: This invention relates to asymmetric syntheses in which a prochiral or chiral compound is contacted in the presence of an optically active metal-ligand complex catalyst to produce an optically active product.
    Type: Grant
    Filed: June 20, 1994
    Date of Patent: February 13, 1996
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: James E. Babin, Gregory T. Whiteker
  • Patent number: 5488174
    Abstract: Process for the hydroformylation of ethylenically unsaturated compounds, by reaction with carbon monoxide and hydrogen in the presence of a catalyst based on a metal of the platinum group, a source of anions and a bidentate ligand of the formula R.sup.1 R.sup.2 M.sup.1 RM.sup.2 R.sup.3 R.sup.4 wherein M.sup.1 and M.sup.2 are phosphorus, arsenic or antimony, R is a bivalent organic bridging group with 1 to 4 atoms in the bridge, R.sup.1 and R.sup.2 together represent a bivalent cyclic group and R.sup.3 and R.sup.4 independently represent an optionally substituted hydrocarbyl group or together have the same meaning as R.sup.1 and R.sup.2.
    Type: Grant
    Filed: August 12, 1994
    Date of Patent: January 30, 1996
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Dennis H. L. Pello, Jacoba C. L. J. Suykerbuyk
  • Patent number: 5481044
    Abstract: .alpha.-alkyl aldehydes having 8 to 17 carbon atoms are obtained from terminal olefins containing one less carbon atom. The olefins are first isomerized in the presence of iron carbonyl and then, without separating out the iron compound, hydroformylated in the presence of rhodium as catalyst.
    Type: Grant
    Filed: December 15, 1994
    Date of Patent: January 2, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jurgen Weber, Helmut Springer
  • Patent number: 5475146
    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: September 2, 1993
    Date of Patent: December 12, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Timothy A. Ayers, Thaliyil V. Rajanbabu
  • Patent number: 5463145
    Abstract: 1,3-Propanediol is prepared in a process comprising the steps of:contacting, in an essentially non-water-miscible organic solvent, ethylene oxide with carbon monoxide and hydrogen in the presence of a catalytic amount of a non-phosphine-ligated cobalt compound and an effective amount of a lipophilic quaternary phosphonium salt promoter at a temperature within the range of about 50.degree. to about 100.degree. C. and a pressure within the range of about 500 to about 5000 psig, to produce an intermediate product mixture comprising less than 15 wt % 3-hydroxypropanal;adding an aqueous liquid to said intermediate product mixture and extracting into said aqueous liquid a major portion of the 3-hydroxypropanal at a temperature less than about 100.degree. C.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: October 31, 1995
    Assignee: Shell Oil Company
    Inventors: Joseph B. Powell, Lynn H. Slaugh, Thomas C. Forschner, Thomas C. Semple, Paul R. Weider
  • Patent number: 5463144
    Abstract: 1,3-propanediol is prepared in a process comprising the steps of:contacting ethylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of an effective amount of a non-phosphine-ligated cobalt catalyst and an effective amount of a lipophilic quaternary ammonium salt at a temperature within the range of about 50.degree. to about 100.degree. C. and a, pressure within the range of about 500 to about 5000 psig, under reaction conditions effective to produce an intermediate product mixture comprising less than 15 wt % 3-hydroxypropanal;adding an aqueous liquid to said intermediate product mixture and extracting into said aqueous liquid at a temperature less than about 100.degree. C.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: October 31, 1995
    Assignee: Shell Oil Company
    Inventors: Joseph B. Powell, Lynn H. Slaugh, Thomas C. Forschner, Terry B. Thomason, Thomas C. Semple, Paul R. Weider, Juan P. Arhancet
  • Patent number: 5463146
    Abstract: 1,3-propanediol is prepared in a process comprising the steps of:(a) contacting ethylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of an effective amount of a non-phosphine-ligated cobalt catalyst and an effective amount of a lipophilic arsine at a temperature within the range of about 50 to about 100.degree. C. and a pressure within the range of about 500 to about 5000 psig, under reaction conditions effective to produce an intermediate product mixture comprising less than about 15 wt % 3-hydroxypropanal;(b) adding an aqueous liquid to said intermediate product mixture and extracting into said aqueous liquid at a temperature less than about 100.degree. C.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: October 31, 1995
    Assignee: Shell Oil Company
    Inventors: Lynn H. Slaugh, Joseph B. Powell, Thomas C. Forschner, Thomas C. Semple, Paul R. Weider
  • Patent number: 5463137
    Abstract: A propylene stream which contains propane as an impurity is contacted with carbon monoxide and hydrogen in the presence of a hydroformylation catalyst thereby producing a product stream containing butyraldehyde and/or n-butyl alcohol, unreacted propylene and propane. A gas mixture containing propylene and propane is separated from the product stream and subjected to adsorption at a temperature of 0.degree. to 250.degree. C. in a bed of adsorbent which selectively adsorbs propylene, thereby adsorbing substantially all of the propylene from the gas mixture. The propylene is desorbed from the adsorbent and recycled to the reaction zone. The process is operated on a low per pass conversion with recycle of unreacted propylene. In the system of the invention the propylene adsorption unit may be upstream or downstream of the hydroformylation reactor.
    Type: Grant
    Filed: April 22, 1994
    Date of Patent: October 31, 1995
    Assignee: The BOC Group, Inc.
    Inventors: Ramakrishnan Ramachandran, Loc H. Dao