Of Olefins Patents (Class 560/233)
  • Patent number: 11773049
    Abstract: Ru-catalysed domino hydroformylation/hydrogenation/esterification using phosphine ligands.
    Type: Grant
    Filed: November 19, 2021
    Date of Patent: October 3, 2023
    Assignee: EVONIK OPERATIONS GMBH
    Inventors: Peter Kucmierczyk, Robert Franke, Matthias Beller, Ricarda Dühren, Ralf Jackstell
  • Patent number: 11542221
    Abstract: The present invention relates to the use of an ?,?-disubstituted carboxylic acid ester of the general formula (I) wherein the variables are as defined in the claims and the description, or of mixtures of two or more of these ?,?-disubstituted carboxylic acid esters or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof as aroma chemicals; to the use thereof for modifying the scent character of a fragranced composition; to an aroma chemical composition containing an ?,?-disubstituted carboxylic acid ester of the general formula (I) or a mixture of two or more of said ?,?-disubstituted carboxylic acid esters or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof; and to a method of preparing a fragranced composition or for modifying the scent character of a fragranced composition. The invention further relates to specific mixtures of ?,?-disubstituted carboxylic acid esters of the general formula (I).
    Type: Grant
    Filed: July 19, 2019
    Date of Patent: January 3, 2023
    Assignee: BASF SE
    Inventors: Manuel Danz, Ralf Pelzer, Miriam Bru Roig, Florian Garlichs
  • Patent number: 8969613
    Abstract: A system and method for removing acetaldehyde from an acetic acid system, including providing a solution from the acetic acid system, the stream having methyl iodide and acetaldehyde, and contacting the solution with an ion-exchange resin and/or liquid catalyst.
    Type: Grant
    Filed: October 31, 2012
    Date of Patent: March 3, 2015
    Assignee: LyondellBasell Acetyls, LLC
    Inventors: Noel C. Hallinan, Brian A. Salisbury
  • Publication number: 20140303387
    Abstract: The invention relates to a process for the manufacture of ?,?-branched carboxylic acids vinyl esters comprising the following steps: isomerising and converting an olefin feed with CO and water under Koch reaction conditions to make an acid with a ratio of Non Blocking isomers (NB) versus Blocking isomers (B) of NB/B above 1.5, wherein a blocking isomer has always a tertiary carbon atom in alpha position of the carboxylic acid and in the beta position of the carboxylic acid, whereas a non-blocking isomer has primary carbon atoms in the beta position of the carboxylic acid converting the resulting acid into a vinyl ester.
    Type: Application
    Filed: April 3, 2012
    Publication date: October 9, 2014
    Applicant: Momentive Specialty Chemicals Inc.
    Inventor: Denis Heymans
  • Patent number: 8815992
    Abstract: Tetraesters of a C4-C5 aliphatic tetracarboxylic acid and OXO-alcohols and plasticized compositions containing said tetraesters are provided.
    Type: Grant
    Filed: April 13, 2011
    Date of Patent: August 26, 2014
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Lisa Saunders Baugh, Enock Berluche, Karla Schall Colle, Manika Varma-Nair, Ramzi Yanni Saleh, Jon Edmond Randolph Stanat, Stephen Zushma, Victor DeFlorio
  • Patent number: 8785678
    Abstract: A continuous process for carbonylation of ethylene in a liquid phase using carbon monoxide, a co-reactant and a suitable catalyst system, including: (i) forming a liquid phase comprising the co-reactant and a suitable catalyst system obtainable by combining: (a) a group VIII metal/compound; (b) a ligand of general formula (I) and c) optionally, a source of anions; wherein Q1 is optionally phosphorous; (ii) forming a gaseous phase in contact with the liquid phase by providing at least an ethylene gas input feed stream and a carbon monoxide gas input feed stream wherein the ethylene:CO molar ratio entering the liquid phase from the input feed streams is greater than 2:1; (iii) reacting ethylene with carbon monoxide in the presence of the co-reactant, and of the suitable catalyst system in the liquid phase; wherein the ethylene:CO gas molar ratio in the gaseous phase is between 20:1 and 1000:1 or wherein the molar ratio of ethylene:CO in the liquid phase is greater than 10:1.
    Type: Grant
    Filed: December 15, 2010
    Date of Patent: July 22, 2014
    Assignee: Lucite International UK Limited
    Inventors: Eastham Graham Ronald, Neil Tindale
  • Patent number: 8686183
    Abstract: The invention provides a method for the hydroxycarbonylation, alkoxycarbonylation, aryloxycarbonylation or thiocarbonylation of an unsaturated molecule. The method includes a hydroxycarbonylation, alkoxycarbonylation, aryloxycarbonylationor thiocarbonylation reaction on the unsaturated molecule in which a complex including a ligand comprising a [n,n?] cyclophane comprising two non-fused monocyclic aromatic rings bridged by two linear and aliphatic linkages, in which each of the non-fused monocyclic aromatic rings is substituted with a phosphorus atom-containing substituent, is used to catalyse the reaction.
    Type: Grant
    Filed: September 10, 2010
    Date of Patent: April 1, 2014
    Assignee: University Court Of The University of St Andrews
    Inventors: Matthew Lee Clarke, Tina Marie Konrad
  • Patent number: 8604236
    Abstract: A continuous carbonylation process for high turnover carbonylation, and a carbonylation reaction medium and product stream thereof. The process comprises carbonylating an ethlenically unsaturated compound with carbon monoxide in the presence of a source of hydroxyl groups and a catalyst system. The catalyst system comprising: (a) a bidentate phosphine, arsine or stibine ligand; and (b) a catalytic metal selected from a group VIB or group VIIIB metal or a compound thereof. The catalytically active concentration of said catalytic metal, measured as the ACCF (product Kg·hr?1·Dm?3), is maintained at less than 0.5.
    Type: Grant
    Filed: August 4, 2006
    Date of Patent: December 10, 2013
    Assignee: Lucite International UK Limited
    Inventors: Ronald Graham Eastham, Neil Tindale
  • Publication number: 20110137059
    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: Application
    Filed: July 2, 2009
    Publication date: June 9, 2011
    Applicant: LUCITE INTERNATIONAL UK LIMITED
    Inventors: Graham Ronald Eastham, Mark Waugh, Paul Pringle, Tamara Fanjul Solares
  • Publication number: 20100197958
    Abstract: A process for the carbonylation of an ethylenically unsaturated compound comprising the step of reacting said compound with carbon monoxide in the presence of a co-5 reactant having a mobile hydrogen atom and a catalyst system is described. The catalyst system is obtainable by combining: (a) a metal of Group 8, 9 or 10 or a suitable compound thereof; (b) a ligand of general formula (I): and c) optionally, a source of anions. The invention is characterised in that the catalyst system includes an enhancer compound comprising an aromatic ring or ring system substituted by at least one hydroxyl group wherein the hydroxyl group pKa at 25° C. is greater than 3.0 and less than 9.1, the said enhancer compound excluding 3-quinolinol.
    Type: Application
    Filed: July 8, 2008
    Publication date: August 5, 2010
    Applicant: LUCITE INTERNATIONAL UK LIMITED
    Inventors: Graham Ronald Eastham, Philip Ian Richards
  • Patent number: 7767770
    Abstract: A method for producing a mixture of ethylene and carbon monoxide by contacting ethane and an oxygen source with a catalyst comprising synthetic cryptomelane or octahedral molecular sieve. The method further comprises condensing the alkyl propionate with formaldehyde to produce an alkyl methacrylate.
    Type: Grant
    Filed: September 17, 2009
    Date of Patent: August 3, 2010
    Assignee: Rohm and Haas Company
    Inventors: Scott Han, Daniel J. Martenak, Lei Jin, Steven Lawrence Suib
  • Publication number: 20100087615
    Abstract: A method for producing a mixture of ethylene and carbon monoxide by contacting ethane and an oxygen source with a catalyst comprising synthetic cryptomelane or octahedral molecular sieve. The method further comprises condensing the alkyl propionate with formaldehyde to produce an alkyl methacrylate.
    Type: Application
    Filed: September 17, 2009
    Publication date: April 8, 2010
    Inventors: Scott Han, Daniel J. Martenak, Lei Jin, Steven Lawrence Suib
  • Publication number: 20090048411
    Abstract: A method for producing a mixture of ethylene and carbon monoxide by contacting ethane and an oxygen source at a temperature of at least 500° C. to produce ethylene and carbon monoxide. A method for producing an alkyl propionate by steps of: (a) contacting ethane and an oxygen source at a temperature of at least 500° C. to produce ethylene; (b) contacting an alcohol, ethylene and carbon monoxide with an ethylene carbonylation catalyst to produce the alkyl propionate; and (c) separating the alkyl propionate from byproducts and starting materials. The method further comprises condensing the alkyl propionate with formaldehyde to produce an alkyl methacrylate.
    Type: Application
    Filed: August 5, 2008
    Publication date: February 19, 2009
    Inventors: Abraham Benderly, Scott Han, Mark Anthony Silvano, Donald Lee Zolotorofe
  • Patent number: 7208635
    Abstract: The invention relates to a hydroformylation process in which at least one olefin having from 2 to 6 carbon atoms is reacted continuously with carbon monoxide and hydrogen in the presence of a hydroformylation catalyst in a reaction zone in which a liquid phase is present and a stream S) is taken from the liquid phase, heat is removed from this stream and the stream is subsequently returned to the reaction zone without removal of a material component.
    Type: Grant
    Filed: January 16, 2003
    Date of Patent: April 24, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Richter, Rolf Müller, Roland Krokoszinski
  • Patent number: 7005537
    Abstract: Disclosed is a process for the production of esters. In particular, the process includes contacting an olefin or an ether with carbon monoxide and an acid composition comprising BF3.2CH3OH to from a product composition, adding an alcohol to the product composition, and separating the BF3.2CH3OH from the ester. The separated BF3.2CH3OH may then be recycled to the reaction unit.
    Type: Grant
    Filed: December 26, 2000
    Date of Patent: February 28, 2006
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Edmund J. Mozeleski, Carl R. Beck, Kirk C. Nadler, Richard H. Schlosberg
  • Patent number: 6998026
    Abstract: A tert-C4–C8-alkyl (meth)acrylate is prepared by reacting (meth)acrylic acid with an olefin of the formula where R1 and R2, which may be identical or different, are methyl or ethyl and R3 is H, methyl or ethyl, in homogeneous phase in the presence of an acidic catalyst and isolating the tert-C4–C8-alkyl (meth)acrylate from the reaction mixture, by a process in which the catalyst is separated off as residue by a two-stage distillation of the reaction mixture and the tert-C4–C8-alkyl (meth)acrylate is isolated from the distillates. The novel process makes it possible to use acetic acid-containing (meth)acrylic acid. The danger of cleavage of the ester and of polymerization of (meth)acrylic compounds is reduced.
    Type: Grant
    Filed: July 27, 2001
    Date of Patent: February 14, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Ruprecht Kroker, Gerhard Nestler, Werner Schmitt, Winfried Schumm
  • Patent number: 6984668
    Abstract: A liquid-phase chemical reaction medium comprises one or more reactants, optionally in the presence of a reaction product(s) and one or more solvents, diluents or other form of liquid carrier, a catalyst system comprising at least a metal or metal compound and optionally further compounds such as ligands or complexing agents; characterized in that the reaction medium further comprises a polymeric dispersant dissolved in said liquid carrier, said polymeric dispersant being capable of stabilizing a colloidal suspension of particles of said metal or metal compound within the liquid carrier. The presence of the polymeric dispersant enables metal formed by catalyst deactivation to be more easily recovered and recycled. Preferably, the polymeric dispersant has sufficiently acidic or basic functionality to stabilize the colloidal suspension of said metal or metal compound.
    Type: Grant
    Filed: August 2, 2000
    Date of Patent: January 10, 2006
    Assignee: Lucite International UK Limited
    Inventors: Graham Ronald Eastham, Raymond Anthony Hadden, David William Johnson
  • Patent number: 6919474
    Abstract: A method for production of pivalic acid comprising the steps of: (a) reacting isobutylene, carbon monoxide, and a first catalyst to produce a reaction mixture; (b) contacting the reaction mixture with water, thereby producing a crude acid product having pivalic acid and oligomeric neo-carboxylic acid; (c) separating the pivalic acid and the oligomeric neo-carboxylic acid from the crude acid product; (d) reacting the oligomeric neo-carboxylic acid with a source of carbon monoxide at a temperature of less than 200° C. in the presence of a second catalyst to produce a C5 carbocation product, wherein the first and second catalyst are either the same or different; and (e) reacting the C5 carbocation product with water; thereby producing pivalic acid having an overall yield of at least 80 wt. %.
    Type: Grant
    Filed: March 31, 2003
    Date of Patent: July 19, 2005
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Edmund J. Mozeleski, Richard H. Schlosberg, Dennis J. Davoren, Carl Robert Beck, Linda J. Broadbelt, Ned C. Haubein
  • Patent number: 6756506
    Abstract: The tert-butyl ester of an aliphatic C1-C4-carboxylic acid is prepared by reacting the carboxylic acid with isobutene in the liquid phase in the presence of an acidic catalyst by a continuous process in which the reaction is carried out in a reactor divided into a plurality of sections, the carboxylic acid, the isoolefin and the catalyst are fed into the first section of the reactor, the reaction mixture obtained is removed from the last section of the reactor and the ester is isolated therefrom, the reaction temperature in the reactor being controlled so that it is from 10 to 40° C. and is highest in the first section of the reactor. The novel process permits the technically simple, economical and environmentally friendly preparation of tertiary butyl esters of saturated and unsaturated C1-C4-carboxylic acids.
    Type: Grant
    Filed: January 27, 2003
    Date of Patent: June 29, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Ruprecht Kroker, Gerhard Nestler, Werner Schmitt, Winfried Schumm
  • Patent number: 6737542
    Abstract: The present invention relates to a process for the carbonylation of conjugated dienes, whereby a conjugated diene is reacted with carbon monoxide and a hydroxyl group containing compound in the presence of a catalyst system including: (a) a source of palladium cations, (b) a phosphorus-containing ligand, (c) a source of anions, wherein the phosphorus-containing ligand is a ligand having the general formula (I): X1—R—X2 wherein X1 and X2 represent a substituted or non-substituted cyclic group with at least 5 ring atoms, of which one is a phosphorus atom, and R represents a bivalent organic bridging group, connecting both phosphorus atoms, containing from 1 to 4 atoms in the bridge, whereby the carbonylation process can be performed batch wise, semi-continuously or continuously.
    Type: Grant
    Filed: September 20, 2001
    Date of Patent: May 18, 2004
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Willem Wabe Jager
  • Patent number: 6706912
    Abstract: Process for the carbonylation of ethylenically unsaturated compounds having 3 or more carbon atoms by reaction with carbon monoxide and an hydroxyl group containing compound in the presence of a catalyst system. The catalyst system includes (a) a source of palladium cations; (b) a bidentate diphosphine of formula I, R1R2>P—R3—R—R4—P<R5R6  (I) wherein P represents a phosphorus atom; R1, R2, R5 and R6 independently represent the same or different optionally substituted organic groups containing a tertiary carbon atom through which the group is linked to the phosphorus atom; R3 and R4 independently represent optionally substituted alkylene groups and R represents an optionally substituted aromatic group; (c) a source of anions derived from an acid having a pKa less than 3, as measured at 18° C. in an aqueous solution. The process is carried out in the presence of an aprotic solvent.
    Type: Grant
    Filed: March 13, 2001
    Date of Patent: March 16, 2004
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Willem Wabe Jager
  • Patent number: 6646159
    Abstract: Long chain alcohols and acids or other similar oxygenates such as esters are produced from paraffins of similar carbon number by a process comprising paraffin dehydrogenation, carbonylation, and separation. Preferably a mixture of paraffins extending over several carbon numbers and recovered from a kerosene fraction is processed, and unconverted paraffins are recycled to a dehydrogenation zone. Alternative reaction zone configurations, catalyst systems and product recovery methods are disclosed.
    Type: Grant
    Filed: December 21, 2000
    Date of Patent: November 11, 2003
    Assignee: UOP LLC
    Inventors: Lance A. Baird, Leonid B. Galperin, R. Joe Lawson, Robert H. Jensen, Oleg L. Eliseev, Albert L. Lapidus, Aduard G. Ostapenco
  • Patent number: 6639091
    Abstract: Bidentate ligand of formula II, R1R2M1—R—M2R3R4  (II) wherein M1 and M2 are independently P, As or Sb; R1, R2, R3 and R4 independently represent tertiary alkyl groups, or R1 and R2 together and/or R3 and R4 together represent an optionally substituted bivalent cycloaliphatic group whereby the two free valencies are linked to M1 or M2, and R represents a bivalent aliphatic bridging group containing from 2 to 6 atoms in the bridge, which is substituted with two or more substituents. A catalyst system comprising: a) a source of group VIII metal cations; b) a source of such a bidentate ligand; and c) a source of anions, and use of such a catalyst system in a process for the carbonylation of optionally substituted ethylenically or acetylenically unsaturated compounds by reaction with carbon monoxide and a coreactant is provided.
    Type: Grant
    Filed: May 17, 2001
    Date of Patent: October 28, 2003
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Michael Rolf Eberhard, Paul Gerard Pringle
  • Patent number: 6570040
    Abstract: The present invention features a chemoselective ligation reaction that can be carried out under physiological conditions. In general, the invention involves condensation of a specifically engineered phosphine, which can provide for formation of an amide bond between the two reactive partners resulting in a final product comprising a phosphine moiety, or which can be engineered to comprise a cleavable linker so that a substituent of the phosphine is transferred to the azide, releasing an oxidized phosphine byproduct and producing a native amide bond in the final product. The selectivity of the reaction and its compatibility with aqueous environments provides for its application in vivo (e.g., on the cell surface or intracellularly) and in vitro (e.g., synthesis of peptides and other polymers, production of modified (e.g., labeled) amino acids).
    Type: Grant
    Filed: March 16, 2001
    Date of Patent: May 27, 2003
    Assignee: The Regents of the University of California
    Inventors: Eliana Saxon, Carolyn Bertozzi
  • Patent number: 6541660
    Abstract: A process is proposed for preparing C5 acetate for Vitamin A synthesis by hydroformylation of 3,4-diacetoxybut-1-ene (3,4-DABE), according to which a 3,4-DABE is used which is obtained by acetoxylation of 1,3-butadiene with acetic acid and air in the presence of a catalyst and removing by distillation the 3,4-DABE formed in this case as by-product.
    Type: Grant
    Filed: March 27, 2002
    Date of Patent: April 1, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Udo Rheude, Maximilian Vicari, Werner Aquila, Günter Wegner, Jörg Niekerken
  • Patent number: 6521801
    Abstract: A process for preparing an 1,3-alkanediol through carbonylation of an epoxide derivative includes the steps of (a) reacting an epoxide derivative with alcohol and carbon monoxide in a solvent at a temperature from about 30 to about 150° C. and at a pressure from about 50 to about 3000 psig in the presence of a catalyst system including an effective amount of a cobalt catalyst and an effective amount of a promoter to afford a reaction mixture including a 3-hydroxyester or derivative thereof in an amount of from 2 to about 95% by weight, (b) separating the reaction product and solvent from the catalyst and promoter, (c) reacting said reaction product and solvent with hydrogen at a temperature from about 30 to about 350° C. and at a pressure from about 50 to about 5000 psig in the presence of a catalyst system for hydrogenation to prepare a hydrogenation product mixture including a 1,3-alkanediol, and (d) recovering the 1,3-alkanediol from the hydrogenation product mixture.
    Type: Grant
    Filed: December 7, 2001
    Date of Patent: February 18, 2003
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Byeong-No Lee, Byung-Soon Chen
  • Patent number: 6521783
    Abstract: This invention relates in part to a processes for the conversion of a feedstock stream comprising carbon monoxide and hydrogen to a product stream comprising at least one of an ester, acid, acid anhydride and mixtures thereof. This invention also relates in part to processes for converting an alcohol and/or ether feedstock to oxygenated products, e.g., esters, acids, acid anhydrides and mixtures thereof. The processes and catalysts are especially suitable for the production of acetic acid and methyl acetate from a synthesis gas feedstock or from an alcohol and/or ether feedstock.
    Type: Grant
    Filed: July 10, 2000
    Date of Patent: February 18, 2003
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Richard William Wegman, David McNeill Somerville, Barry Brent Fish, Raymond Edwin Rooks, Chinsoo Stephen Lee, Paul Frank Bryan, William J. Bartley, David Michael Anthony Minahan, Fungau Ho
  • Patent number: 6489506
    Abstract: A process for the liquid-phase carbonylation of ethylene, according to the equation C2H4+CO+ROH→C2H5CO2R, in the presence of a catalyst system comprising a Group VIII metal or compound thereof, a phosphine ligand and a source of anions, and in the presence of water or a source of organic hydroxyl groups, is carried out in conditions in which the molar ratio of ethylene to carbon monoxide in the gaseous phase of the reactor is greater than 1:1. The higher ratios of ethylene to carbon monoxide are beneficial in increasing the turnover number of the catalyst system.
    Type: Grant
    Filed: June 21, 2001
    Date of Patent: December 3, 2002
    Assignee: Lucite International UK Limited
    Inventors: Jean Margaret Pearson, Raymond Anthony Hadden
  • Patent number: 6476255
    Abstract: A process for the manufacture of an alkyl ester of an aliphatic carboxylic acid comprises the steps of supplying a first feed stream comprising carbon monoxide and an alkene of formula CnH2n to a reactor, supplying a second feed stream comprising an alkyl alcohol, having a formula R—OH where R is an optionally substituted alkyl group, to the reactor, and reacting together said first and second feed streams in the reactor in the presence of a carbonylation catalyst, which catalyses the carbonylation reaction between carbon monoxide and the alkene, to form a product comprising an alkyl alkanoate having the formula CnH2n+1COOR, such that the ratio of alkyl alcohol to alkyl alkanoate present in the reactor is greater than the ratio of alkyl alcohol to alkyl alkanoate present in an azeotropic mixture of the alkyl alcohol and alkyl alkanoate. The process is particularly useful for the manufacture of methyl propionate by the methoxycarbonylation of ethylene.
    Type: Grant
    Filed: November 1, 2000
    Date of Patent: November 5, 2002
    Assignee: Lucite International UK Limited
    Inventors: Raymond A Hadden, Jean M Pearson
  • Patent number: 6452043
    Abstract: A method for producing esters, carboxylic acids and mixtures thereof includes contacting, under carbonylation conditions, lower alkyl alcohols, ethers, lower alkyl alcohol derivatives and mixtures thereof and carbon monoxide with a catalyst having a catalytically effective amount a metal selected from iron, cobalt, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum, tin and mixtures thereof associated with a carbonized polysulfonated divinylbenzene-styrene copolymer matrix. In a preferred aspect of the invention the method is called out under vapor-phase conditions.
    Type: Grant
    Filed: April 5, 2000
    Date of Patent: September 17, 2002
    Assignee: Eastman Chemical Company
    Inventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
  • Patent number: 6355711
    Abstract: A plasticizer ester prepared from the catalytic reaction of (1) at least one branched C7-C11 oxo alcohol prepared from C6-C10 olefins via hydroformylation and having at least 50% methyl branching at the beta carbon, and (2) at least one acid or anhydride.
    Type: Grant
    Filed: March 31, 1999
    Date of Patent: March 12, 2002
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Allen David Godwin, Dwight McLean Lyman
  • Publication number: 20010041808
    Abstract: Disclosed is a process for the production of esters. In particular, the process includes contacting an olefin or an ether with carbon monoxide and an acid composition comprising BF3.2CH3OH to from a product composition, adding an alcohol to the product composition, and separating the BF3.2CH3OH from the ester. The separated BF3.2CH3OH may then be recycled to the reaction unit.
    Type: Application
    Filed: December 26, 2000
    Publication date: November 15, 2001
    Inventors: Edmund J. Mozeleski, Carl R. Beck, Kirk C. Nadler, Richard H. Schlosberg
  • Patent number: 6294687
    Abstract: The present invention discloses this invention relates to a process for the conversion of olefinically unsaturated compounds to corresponding carboxylic acids and their esters of formula III wherein R1, R2, R3 and R4 may independently be hydrogen, alkyl, aryl, arylalkyl, cycloaliphatic with or without substituents, R and R5 may be H and COOR′ or vice versa wherein R′ may be H in the case of acids and may be alkyl, aryl, arylalkyl, cycloaliphatic with or without substituents, in the case of esters, wherein said conversion is carried out in the presence of a transition metal complex catalyst of the formula.
    Type: Grant
    Filed: December 30, 1999
    Date of Patent: September 25, 2001
    Assignee: Council of Scientific and Industrial Research
    Inventors: Raghunath Vitthal Chaudhari, A. Seayad, Jayasree Seayad
  • Patent number: 6284919
    Abstract: A process for the liquid-phase carbonylation of ethylene, according to the equation C2H4+CO+ROH→C2H5CO2R, in the presence of a catalyst system comprising a Group VIII metal or compound thereof, a phosphine ligand and a source of anions, and in the presence of water or a source of organic hydroxyl groups, is carried out in conditions in which the molar ratio of ethylene to carbon monoxide in the gaseous phase of the reactor is greater than 1:1. The higher ratios of ethylene to carbon monoxide are beneficial in increasing the turnover number of the catalyst system.
    Type: Grant
    Filed: September 15, 1999
    Date of Patent: September 4, 2001
    Assignee: Imperial Chemical Industries PLC
    Inventors: Jean Margaret Pearson, Raymond Anthony Hadden
  • Patent number: 6274096
    Abstract: The retrofitting of an existing methanol or methanol/ammonia plant to make acetic acid is disclosed. The plant is retrofitted to feed carbon dioxide into a reformer to which natural gas and steam (water) are fed. Syngas is formed in the reformer wherein both the natural gas and the carbon dioxide are reformed to produce syngas with a large proportion of carbon monoxide relative to reforming without added carbon dioxide. The syngas is split into a first part and a second part. The first syngas part is converted to methanol in a conventional methanol synthesis loop that is operated at about half of the design capacity of the original plant. The second syngas part is processed to separate out carbon dioxide and carbon monoxide, and the separated carbon dioxide is fed back into the feed to the reformer to enhance carbon monoxide formation. The separated carbon monoxide is then reacted with the methanol to produce acetic acid or an acetic acid precursor by a conventional process.
    Type: Grant
    Filed: November 1, 1999
    Date of Patent: August 14, 2001
    Assignee: Acetex (Cyprus) Limited
    Inventors: Daniel Marcel Thiebaut, Kenneth Ebenes Vidalin
  • Patent number: 6049011
    Abstract: A dilute ethylene stream, e.g., one produced by steam cracking, is oxonated to yield propanal, without the need to separate other lower hydrocarbons.
    Type: Grant
    Filed: October 15, 1997
    Date of Patent: April 11, 2000
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Gabor Kiss, Michael G Matturro, Harry William Deckman, Frank Hershkowitz, David R. Lumgair, Jr., Gary F Janda, Daniel N King
  • Patent number: 6037506
    Abstract: A process is presented in which ethylenically unsaturated compounds are reacted with carbon monoxide and hydrogen to form reaction products. The reactants are contacted in the presence of a catalyst system made by combining: (a) a source of palladium, platinum, or nickel,(b) a bidentate ligand of the formula R.sub.1 R.sub.2 M.sub.1 RM.sub.2 R.sub.3 R.sub.4 in which M.sub.1 and M.sub.2 independently may be phosphorus, arsenic, or antimony atoms, R is a bivalent organic bridging group and R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are unsubstituted or substituted aliphatic groups, wherein one or more combinations of R.sub.1, R.sub.2, R.sub.3, and R.sub.4 form a bivalent cyclic group, and(c) an acid,and a promoter which is a formate, formic acid, or formic acid forming reagent provided that it is not an orthoformate.
    Type: Grant
    Filed: September 18, 1998
    Date of Patent: March 14, 2000
    Assignee: Shell Oil Company
    Inventor: Cornelius Mark Bolinger
  • Patent number: 6011171
    Abstract: The present invention provides a process for synthesizing tertiary carboxylic acids or the esters thereof having one or two more carbon atoms than the raw material has, comprising reacting in a strong acid (e.g., sulfuric acid, sulfuric acid-phosphoric acid, hydrogen fluoride, fluorosulfuric acid, boron trifluoride.water complex and trifluoromethanesulfonic acid) a raw material compound (i.e., olefin, alcohol, diene, diol or saturated hydrocarbon) with carbon monoxide in the presence of a specific metal carbonyl catalyst (i.e., platinum carbonyl catalyst, palladium carbonyl catalyst and gold dicarbonyl catalyst).The metal carbonyl catalyst is formed by reacting in a strong acid at least one specific metal compounds (e.g., platinum compound such as platinum (II, IV) oxide, platinum (II, IV) hydroxide, a platinum powder, etc.; palladium compound such as palladium (II, III, IV) oxide, palladium (II) hydroxide, palladium (II) sulfate, palladium (II) carboxylate, a palladium powder, etc.
    Type: Grant
    Filed: November 4, 1997
    Date of Patent: January 4, 2000
    Assignee: Jiro Hiraishi, Director-General, Agency of Industrial Science and Technology
    Inventors: Qiang Xu, Yoshie Souma
  • Patent number: 5936117
    Abstract: Disclosed is a process for the preparation of aliphatic carbonyl compounds selected from aliphatic carboxylic acids, alkyl esters of aliphatic carboxylic acids and anhydrides of aliphatic carboxylic acids by the carbonylation of olefins in the presence of a catalyst system comprising (1) a primary component selected from at least one Group 6 metal, i.e., chromium, molybdenum, and/or tungsten and (2) a secondary component selected from at least one of certain halides and tertiary and quaternary compounds of a Group 15 element, i.e., nitrogen, phosphorus and/or arsenic. The process constitutes and improvement over known processes since it can be carried out at moderate carbonylation conditions without the necessity of using an expensive noble metal catalyst, volatile, toxic materials such as nickel tetracarbonyl, formic acid or a formate ester.
    Type: Grant
    Filed: July 28, 1995
    Date of Patent: August 10, 1999
    Assignee: Eastman Chemical Company
    Inventors: Joseph Robert Zoeller, Elizabeth MacGowan West, Horace Lawrence Browning, Jr., George Geiger Mayfield
  • Patent number: 5932761
    Abstract: It is provided a process for industrially advantageously producing a branched aldehyde represented by the formula; ##STR1## ?wherein Y represents an acyl group of two or more carbon atoms; and X represents an acyloxymethyl group represented by --CH.sub.2 OY' (where Y' represents an acyl group of two or more carbon atoms), cyano group or an alkoxycarbonyl group! which is useful as an intermediate for pharmaceuticals and agricultural chemicals, comprising subjecting an olefinic compound represented by the following formula; ##STR2## (wherein Y and X are the same as defined above), to the reaction with hydrogen and carbon monoxide in the presence of a rhodium compound and a tertiary organic phosphorus compound with an electronic parameter (.upsilon.-value) of 2080 to 2090 cm.sup.-1 or with a steric parameter (.theta.-value) of 150 to 180.degree..
    Type: Grant
    Filed: March 23, 1998
    Date of Patent: August 3, 1999
    Assignee: Kuraray Co., Ltd.
    Inventors: Toshihiro Omatsu, Masahiko Kitayama, Takashi Onishi
  • Patent number: 5834622
    Abstract: A process for the carbonylation of a carbonylatable reactant having a carbonylatable moiety having at least two carbon atoms and/or a reactive derivative thereof which process comprises contacting said carbonylatable reactant and/or a reactive derivative thereof with carbon monoxide in a liquid reaction composition in a carbonylation reactor characterized in that the liquid reaction composition comprises: (a) an iridium catalyst, (b) a halide, (c) at least a finite concentration of water, (d) a carbonylatable reactant having a carbonylatable moiety having at least two carbon atoms and/or a reactive derivative thereof and (e) as promoter, at least one of ruthenium and osmium.
    Type: Grant
    Filed: July 5, 1996
    Date of Patent: November 10, 1998
    Assignee: BP Chemicals Limited
    Inventor: John Glenn Sunley
  • Patent number: 5760284
    Abstract: Disclosed is an improved catalyst system and process for preparing aliphatic carbonyl compounds such as aliphatic carboxylic acids, alkyl esters of aliphatic carboxylic acids and anhydrides of aliphatic carboxylic acids by carbonylating olefins in the presence of a catalyst system comprising (1) a first component selected from at least one Group 6 metal, i.e., chromium, molybdenum, and/or tungsten and (2) a second component selected from at least one of certain halides and tertiary and quaternary compounds of a Group 15 element, i.e., nitrogen, phosphorus and/or arsenic, and (3) as a third component, a polar, aprotic solvent. The process employing the improved catalyst system is carried out under carbonylating conditions of pressure and temperature discussed herein.
    Type: Grant
    Filed: April 10, 1997
    Date of Patent: June 2, 1998
    Assignee: Eastman Chemical Company
    Inventor: Joseph Robert Zoeller
  • Patent number: 5705683
    Abstract: The process for carbonylating olefins with carbon monoxide in the presence of water, an alcohol or a carboxylic acid and a halogen-free catalyst comprises using a catalyst comprising nickel or a nickel compound and at least one of the metals of the group consisting of chromium, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver and gold, or a compound of these metals.
    Type: Grant
    Filed: January 13, 1997
    Date of Patent: January 6, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Ferdinand Lippert, Arthur Hohn, Martin Schafer, Leopold Hupfer
  • Patent number: 5698722
    Abstract: A Koch functionalized product which is the reaction product of at least one polymer having a number average molecular weight of at least 500 and at least ethylenic double bond per polymer chain, with carbon monoxide and a nucleophilic trapping agent. The invention includes functionalized polymer, derivatives thereof and methods of making the same.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: December 16, 1997
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Joseph Victor Cusumano, William Daniel Diana, Jacob Emert, Keith Raymond Gorda, Richard H. Schlosberg, David A. Young, William Bernard Eckstrom, Edris Eileen Manry, Michael John Keenan
  • Patent number: 5679831
    Abstract: Process for the preparation of a terminal ester by carbonylation of an internally unsaturated organic compound in the presence of an alcohol, carbon monoxide, palladium, an acid with a pK.sub.a of less than 2 (measured at 18.degree. C. in an aqueous solution) and a bidentate organic phosphorus, antimony or arsenic ligand compound having a bridging group, wherein the bridging group comprises a bis(.eta.-cyclopentadienyl) coordination group of a transition metal.
    Type: Grant
    Filed: January 5, 1995
    Date of Patent: October 21, 1997
    Assignees: DSM N.V., E. I. Du Pont de Nemours and Company
    Inventor: Otto E. Sielcken
  • Patent number: 5650536
    Abstract: A continuous process for functionalizing olefins, especially polymer olefins in a CSTR or pipe reactor. Esters are preferably produced by continuous reaction of the olefin with carbon monoxide and a nucleophilic trapping agent. The liquid-filled pipe reactor operates in plug flow with static mixers and the CSTR is operated in the substantial absence of air at constant liquid level.
    Type: Grant
    Filed: June 17, 1994
    Date of Patent: July 22, 1997
    Assignee: Exxon Chemical Patents Inc.
    Inventors: David C. Dankworth, William H. Cross, Joseph V. Cusumano, William D. Diana, William B. Eckstrom, Jacob I. Emert, Keith R. Gorda, Robert M. Koros, Harold W. Margo, Jon E. Stanat
  • Patent number: 5463095
    Abstract: A process for the production of esters, comprising allowing an olefin, carbon monoxide and an alcohol to react in the presence of hydrogen fluoride, in which the esters can be produced at high yields at a low temperature for a short period of time, the esters can be easily separated from a reaction solution, hydrogen fluoride can be recycled, the esters can be produced at a low cost, a mixture of esters can be easily produced, the kinetic viscosity of the mixture of the esters can be easily adjusted and the coloring of, and an increase in the viscosity of, the esters can be prevented.
    Type: Grant
    Filed: June 14, 1994
    Date of Patent: October 31, 1995
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Yoshihiro Shiokawa, Tadayoshi Takefumi, Shunichi Matsumoto, Yoshifumi Sato
  • Patent number: 5364957
    Abstract: The invention relates to a process for the carbonylation of an olefinically or acetylenically unsaturated hydrocarbon compound by reaction with carbon monoxide and a hydroxy compound in the presence of a catalyst system comprising a source of cationic palladium, a source of phosphine and a protonic acid, which reaction is carried out in the presence of a free radical inhibitor.
    Type: Grant
    Filed: April 8, 1993
    Date of Patent: November 15, 1994
    Assignee: Shell Oil Company
    Inventors: Peter Arnoldy, Antoon P. M. Kremers
  • Patent number: 5324856
    Abstract: Disclosed is a process for making an .alpha.-hydroxy acid which is essentially all L or all D with respect to the chiral C atom bonded to the carboxy group of said acid which comprises (1) hydrocarboxylating an enol acylate, which has a chiral C atom that is essentially all L or all D, with CO and water or an organic hydroxyl compound, thereby producing a reaction mixture containing diastereomeric .alpha.-acyloxy acids or esters having two chiral centers and having essentially no enantiomeric pairs, (2) separating the diastereomers by conventional physical means and (3) hydrolyzing at least one of said separated diastereomers to make at least the .alpha.-hydroxy acid which is essentially all L or all D with respect to the chiral C atom bonded to the carboxy group of said acid.Also disclosed is a process for making an .alpha.
    Type: Grant
    Filed: August 17, 1992
    Date of Patent: June 28, 1994
    Inventors: Mark C. Cesa, Robert A. Dubbert, James D. Burrington
  • Patent number: 5321155
    Abstract: Cyclohexyladipates are produced by reacting a mixture containing a major amount of benzene and minor amounts of cyclohexene, adipic acid and an acid catalyst.
    Type: Grant
    Filed: April 15, 1993
    Date of Patent: June 14, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: William C. Drinkard, Gerald C. Grunewald