Formation Of Carboxyl Group By Carbonation Patents (Class 562/550)
  • Patent number: 9982353
    Abstract: Water electrolyzers employs base metal catalysts and an anion-conducting polymeric membrane comprising a polymer of styrene, vinylbenzyl-Rs and possibly vinylbenzyl-Rx. Rs is a positively charged cyclic amine group. Rx is at least one constituent selected from the group consisting of —Cl, —OH, and a reaction product between an —OH or —Cl and a species other than a simple amine or a cyclic amine.
    Type: Grant
    Filed: January 16, 2017
    Date of Patent: May 29, 2018
    Assignee: Dioxide Materials, Inc.
    Inventors: Richard I. Masel, Zengcai Liu
  • Patent number: 9945040
    Abstract: A catalyst layer for an electrochemical device comprises a catalytically active element and an ion conducting polymer. The ion conducting polymer comprises positively charged cyclic amine groups. The ion conducting polymer comprises at least one of an imidazolium, a pyridinium, a pyrazolium, a pyrrolidinium, a pyrrolium, a pyrimidium, a piperidinium, an indolium, a triazinium, and polymers thereof. The catalytically active element comprises at least one of V, Cr, Mn, Fe, Co, Ni, Cu, Sn, Zr, Nb, Mo, Ru, Rh, Pd, Ag, Cd, Hf, Ta, W, Re, Ir, Pt, Au, Hg, Al, Si, In, Tl, Pb, Bi, Sb, Te, U, Sm, Tb, La, Ce and Nd. In an electrolyzer comprising the present catalyst layer, the feed to the electrolyzer comprises at least one of CO2 and H2O.
    Type: Grant
    Filed: May 18, 2016
    Date of Patent: April 17, 2018
    Assignee: Dioxide Materials, Inc.
    Inventors: Richard I. Masel, Zengcai Liu, Robert Kutz, Syed Dawar Sajjad
  • Patent number: 9758461
    Abstract: Catalytic process for preparing an ?,?-ethylenically unsaturated carboxylic acid salt, wherein an alkene and carbon dioxide are reacted in the presence of a carboxylation catalyst and in the presence of a specific aryloxide to obtain the ?,?-ethylenically unsaturated carboxylic acid salt, the carboxylation catalyst being a transition metal complex. The process allows for efficient preparation of ?,?-ethylenically unsaturated carboxylic acid derivatives from CO2 and an alkene.
    Type: Grant
    Filed: May 13, 2015
    Date of Patent: September 12, 2017
    Assignee: BASF SE
    Inventors: Michael Limbach, Michael Lejkowski, Nuria Huguet Subiela, Alvaro Gordillo, Ronald Lindner, Miriam Bru Roig, Stephan A. Schunk
  • Patent number: 9346772
    Abstract: The present application relates to a preparation method for solid powder of a carbamic acid derivative, which includes reacting an amine derivative with carbon dioxide at a temperature in a range of from about ?30° C. to about 500° C. and at a pressure in a range of from about 0.3 MPa to about 100 MPa. In addition, the present disclosure relates to a reduction method for solid powder of a carbamic acid derivative to an amine derivative and carbon dioxide, which includes dissolving solid powder of the carbamic acid derivative prepared in a solvent; refluxing the carbamic acid derivative at a temperature in a range of from about 30° C. to about 100° C.; and evaporating the solvent.
    Type: Grant
    Filed: August 11, 2015
    Date of Patent: May 24, 2016
    Assignee: Sogang University Research Foundation
    Inventors: Nam Hwi Hur, Byeong No Lee
  • Publication number: 20150099886
    Abstract: The present application relates to a preparation method for solid powder of a carbamic acid derivative, which includes reacting an amine derivative with carbon dioxide at a temperature in a range of from about ?30° C. to about 500° C. and at a pressure in a range of from about 0.3 MPa to about 100 MPa. In addition, the present disclosure relates to a reduction method for solid powder of a carbamic acid derivative to an amine derivative and carbon dioxide, which includes dissolving solid powder of the carbamic acid derivative prepared in a solvent; refluxing the carbamic acid derivative at a temperature in a range of from about 30° C. to about 100° C.; and evaporating the solvent.
    Type: Application
    Filed: December 11, 2014
    Publication date: April 9, 2015
    Inventors: Nam Hwi HUR, Byeong No LEE
  • Publication number: 20150051421
    Abstract: The invention relates to a process for the preparation of D,L-methionine, in which carbon dioxide is fed to an aqueous potassium methioninate solution obtained by hydrolysis of 5-(2-methylmercaptoethyl)hydantoin, in order to precipitate out crude methionine, which is separated off and purified, where, for the purposes of purification, an aqueous solution of the separated-off crude methionine is prepared and subjected to a recrystallization, characterized in that the solution from which the recrystallization takes place contains potassium ions and also a crystallization additive, where the crystallization additive is a nonionic or anionic surfactant, or a mixture of different nonionic or anionic surfactants, and that the recrystallization takes place by introducing a 60 to 110° C.-hot methionine solution into a 35 to 80° C.-warm methionine suspension, the temperature of which is lower than that of the introduced solution, the temperature of the methionine suspension being maintained between 35 and 80° C.
    Type: Application
    Filed: February 26, 2013
    Publication date: February 19, 2015
    Applicant: EVONIK INDUSTRIES AG
    Inventors: Martin Koerfer, Hans Joachim Hasselbach, Stefan Reichert, Harald Jakob, Christoph Weckbecker, Klaus Huthmacher, Horst Krull, Bernd Drapal, Rainer Peter
  • Patent number: 8877965
    Abstract: A process for preparing formic acid by reaction of carbon dioxide (1) with hydrogen (2) in a hydrogenation reactor (I) in the presence of a catalyst comprising an element of group 8, 9 or 10 of the Periodic Table, a tertiary amine comprising at least 12 carbon atoms per molecule and a polar solvent comprising one or more monoalcohols selected from among methanol, ethanol, propanols and butanols, to form formic acid/amine adducts as intermediates which are subsequently thermally dissociated, where the work-up of the output (3) from the hydrogenation reactor (I) is carried out by addition of water so as to increase the distribution coefficient of the catalyst between the upper phase (4) and the lower phase.
    Type: Grant
    Filed: June 29, 2011
    Date of Patent: November 4, 2014
    Assignee: BASF SE
    Inventors: Thomas Schaub, Donata Maria Fries, Rocco Paciello, Klaus-Dieter Mohl, Martin Schäfer, Stefan Rittinger, Daniel Schneider
  • Patent number: 8741255
    Abstract: Peroxo-carbonates derived from molten alkali and/or Group II metal salts, particularly carbonate salts are used as catalysts in oxidation and epoxidation reactions. Transition metal compounds may be included to improve the selectivity of the reactions.
    Type: Grant
    Filed: July 27, 2007
    Date of Patent: June 3, 2014
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Helge Jaensch, Gary David Mohr
  • Patent number: 8697909
    Abstract: In a process for preparing an alkali metal or alkaline earth metal salt of an ?,?-ethylenically unsaturated carboxylic acid, a) a transition metal-alkene complex is reacted with CO2 to give a metallalactone, b) the metallalactone is reacted with a base to give an adduct of the alkali metal or alkaline earth metal salt of the ?,?-ethylenically unsaturated carboxylic acid with the transition metal complex, and c) the adduct is reacted with an alkene to release the alkali metal or alkaline earth metal salt of the ?,?-ethylenically unsaturated carboxylic acid and regenerate the transition metal-alkene complex. The base is selected from alkali metal or alkaline earth metal hydroxides and alkali metal or alkaline earth metal superbases. The alkene is, for example, ethene. The transition metal complex comprises, for example, nickel and a bidentate P,P, P,N, P,O or P,carbene ligand, such as 1,2-bis(di-tert-butylphosphino)ethane.
    Type: Grant
    Filed: December 27, 2012
    Date of Patent: April 15, 2014
    Assignee: BASF SE
    Inventors: Michael Limbach, Ronald Lindner, Michael Ludwik Lejkowski, Takeharu Kageyama, Gabriella Eva Bodizs, Stephan Schunk, Cornelia Futter, Jörg Rother
  • Publication number: 20140058132
    Abstract: The invention relates to a method for producing acetylenedicarboxylic acid by reaction of acetylene with carbon dioxide, wherein the reaction is carried out in the presence of a silver or copper salt and an amine base.
    Type: Application
    Filed: August 16, 2013
    Publication date: February 27, 2014
    Applicant: BASF SE
    Inventors: Matthias Arndt, Lukas J. Goossen
  • Publication number: 20140051858
    Abstract: The present disclosure relates to a preparation method for powder of a carbamic acid derivative, which includes reacting a liquid amine derivative with carbon dioxide at a temperature in a range of from about ?30° C. to about 500° C. at a pressure in a range of from about 0.3 MPa to about 100 MPa. In addition, the present disclosure relates to a reduction method for powder of a carbamic acid derivative to a liquid amine derivative and carbon dioxide, which includes dissolving powder of the carbamic acid derivative prepared in a solvent; refluxing the carbamic acid derivative at a temperature in a range of from about 30° C. to about 100° C.; and evaporating the solvent.
    Type: Application
    Filed: August 14, 2013
    Publication date: February 20, 2014
    Applicant: Sogang University Research Foundation
    Inventors: Nam Hwi HUR, Byeong No LEE
  • Publication number: 20140024800
    Abstract: A method for treating carbon dioxide includes preparing a polyamine composition and delivering a stream containing carbon dioxide to the polyamine composition. The carbon dioxide reacts with polyamine in the polyamine composition to form a carbamate salt. A method for producing polyurea from carbon dioxide includes delivering a stream containing carbon dioxide to a polyamine composition. The carbon dioxide reacts with polyamine in the polyamine composition to form a carbamate salt. The method also includes dehydrating the carbamate salt to produce polyurea.
    Type: Application
    Filed: July 17, 2012
    Publication date: January 23, 2014
    Applicant: UNIVERSITY OF NORTH DAKOTA
    Inventor: Qianli Chu
  • Publication number: 20140018573
    Abstract: The present disclosure relates to a method of preparing powder of a solid carbazic acid derivative, which involves inducing a reaction of a liquid hydrazine derivative with carbon dioxide at a high pressure of from about 0.5 MPa to about 100 MPa. During the reaction, the pressure may range from about 0.5 MPa to about 100 MPa. In this regard, although the reaction of the carbon dioxide with the liquid hydrazine derivative occurs when the pressure is adjusted to below than about 0.5 MPa, sticky precipitates in a form of gel are gradually produced but the powder is not produced.
    Type: Application
    Filed: June 27, 2013
    Publication date: January 16, 2014
    Inventors: Nam Hwi HUR, Byeong No LEE
  • Publication number: 20140012000
    Abstract: The invention relates to a process for preparing a propiolic acid or a derivative thereof by reacting a terminal alkyne with carbon dioxide, which comprises performing the reaction in the presence of a base and a copper complex, especially a copper (I) complex having at least one ligand, at least one of the ligands of the copper complex being selected from monodentate ligands which have an aminic or iminic nitrogen atom capable of coordination with copper, and polydentate ligands having at least two atoms or atom groups which are capable of simultaneous coordination with copper and are selected from nitrogen, oxygen, sulfur, phosphorus and carbene carbon.
    Type: Application
    Filed: August 19, 2011
    Publication date: January 9, 2014
    Applicant: BASF SE
    Inventors: Lukas J Goossen, Nuria Rodriguez Garrido, Filipe Manjolinho Costa, Paul P. Lange
  • Publication number: 20120022290
    Abstract: A process for preparing formic acid by reaction of carbon dioxide (1) with hydrogen (2) in a hydrogenation reactor (I) in the presence of a catalyst comprising an element of group 8, 9 or 10 of the Periodic Table, a tertiary amine comprising at least 12 carbon atoms per molecule and a polar solvent comprising one or more monoalcohols selected from among methanol, ethanol, propanols and butanols, to form formic acid/amine adducts as intermediates which are subsequently thermally dissociated, where the work-up of the output (3) from the hydrogenation reactor (I) is carried out by addition of water so as to increase the distribution coefficient of the catalyst between the upper phase (4) and the lower phase.
    Type: Application
    Filed: June 29, 2011
    Publication date: January 26, 2012
    Applicant: BASF SE
    Inventors: Thomas Schaub, Donata Maria Fries, Rocco Paciello, Klaus-Dieter Mohl, Martin Schäfer, Stefan Rittinger, Daniel Schneider
  • Publication number: 20110237830
    Abstract: Catalysts comprised of at least one catalytically active element and at least one helper catalyst are disclosed. The catalysts may be used to increase the rate, the selectivity or lower the overpotential of chemical reactions. These catalysts may be useful for a variety of chemical reactions including in particular the electrochemical conversion of carbon dioxide to formic acid.
    Type: Application
    Filed: July 4, 2010
    Publication date: September 29, 2011
    Applicant: Dioxide Materials Inc
    Inventor: Richard Isaac Masel
  • Patent number: 7893298
    Abstract: The invention relates to a method for concentrating an aqueous ammonium carbamate stream, which has been formed in a process for the preparation of urea, has a pressure between 0.20 MPa and 0.9 MPa, a temperature between 35° C. and 95° C., and contains at least 25 wt. % H2O, comprising: a pressure increase step, in which the aqueous ammonium carbamate stream is increased in pressure to a pressure between 1.0 MPa and 7 MPa; a condensation step, in which the aqueous ammonium carbamate stream is contacted with a gas stream, which has been formed in a process for the preparation of melamine and which consists essentially of NH3, CO2 and optionally H2O and has a lower H2O content than the aqueous ammonium carbamate stream, the gas stream being absorbed in the aqueous ammonium carbamate stream in such a way that a concentrated ammonium carbamate stream is formed that contains between 15 and 35 wt. % H2O; a discharge step, in which the concentrated ammonium carbamate stream is separated and discharged.
    Type: Grant
    Filed: May 15, 2006
    Date of Patent: February 22, 2011
    Assignee: Stamicarbon B.V.
    Inventors: Johannes Henricus J. H. Mennen, Tjay Tjien T. T. Tjioe
  • Publication number: 20090030214
    Abstract: Peroxo-carbonates derived from molten alkali and/or Group II metal salts, particularly carbonate salts are used as catalysts in oxidation and epoxidation reactions, transition metal compounds may be included to improve the selectivity of the reactions.
    Type: Application
    Filed: July 27, 2007
    Publication date: January 29, 2009
    Inventors: Helge Jaensch, Gary David Mohr
  • Patent number: 7399883
    Abstract: Disclosed in a process for making (1) a compound of the formula NC—CH2—CH2—CH2—CH2—CO2R?, wherein R? is H or C1 to C12 alkyl, or (2) adipic acid or (3) dimethyl adipate, using as the substrate, 3-pentenenitrile, (2) 3-pentenoic acid or methyl 3-pentenoate, respectively, by contacting the substrate with carbon monoxide and a nucleophile in the presence of a Group VIII metal, a selected ligand, and an acid promoter. The nucleophile, which (a) an alcohol or water, or (b) water or (c) methanol, respectively, in the presence of a Group VIII metal, preferably palladium, a selected phosphine ligand, and an acid promoter.
    Type: Grant
    Filed: July 17, 2006
    Date of Patent: July 15, 2008
    Assignee: Invista North America S.A.R.L.
    Inventors: Emilio E. Brunel, David A. Clark
  • Publication number: 20080051601
    Abstract: A method for removing aldehyde impurities from an acetic acid stream is disclosed. The method comprises reacting aldehyde impurities with a hydroxyl compound in a drying distillation column or a combined column to form corresponding acetals. The acetals are subsequently removed as heavy impurities from acetic acid by distillation.
    Type: Application
    Filed: August 22, 2006
    Publication date: February 28, 2008
    Inventors: Gary A. Sawyer, Wayne J. Brtko, Ronnie M. Hanes, Brian A. Salisbury
  • Patent number: 6960682
    Abstract: Acetyl anhydrides such as acetyl sulfate are produced by a process for comprising contacting methane and carbon dioxide in an anhydrous environment in the presence of effective amounts of a transition metal catalyst and a reaction promoter, and an acid anhydride compound, and optionally an acid. The acetyl anhydride can be contacted with water to produce acetic acid or with an alcohol to produce a product comprising an acetate ester and that may also comprise acetic acid. Optionally, water in stoichiometric amounts or less, with respect to the acetic anhydride, may be fed to a continuous process of this type to produce some acetic acid in situ.
    Type: Grant
    Filed: July 22, 2004
    Date of Patent: November 1, 2005
    Assignees: The Regents of the University of California, BP Chemicals Limited
    Inventors: Alexis T. Bell, Sudip Mukhopadhyay, Mark Zerella, John Glenn Sunley, Sander Gaemers, Michael James Muskett
  • Patent number: 6914157
    Abstract: The invention relates to a method for obtaining an ammonium carbamate solution from a gas mixture that contains more than 40 wt. % NH3, less than 50 wt. % CO2 and less than 40 wt. % H2O and has a pressure between 0.1 MPa and 4 MPa, comprising a compression step, in which the pressure of the gas mixture is increased to a pressure between 0.5 MPa and 25 MPa, and an absorption step.
    Type: Grant
    Filed: July 3, 2002
    Date of Patent: July 5, 2005
    Assignee: DSM IP Assets B.V.
    Inventor: Guillaume Mario Hubert Jozef Lardinois
  • Patent number: 6646154
    Abstract: A vapor-phase carbonylation method for producing esters and carboxylic acids from reactants comprising lower alkyl alcohols, lower alkyl alcohol generating compounds, and mixtures thereof. The method includes contacting the reactants and carbon monoxide in a carbonylation zone of a carbonylation reactor under vapor-phase carbonylation conditions with a catalyst having a catalytically effective amount of a Group VIII metal selected from platinum or palladium, and tungsten which are associated with a solid catalyst support material.
    Type: Grant
    Filed: June 20, 2001
    Date of Patent: November 11, 2003
    Assignee: Eastman Chemical Company
    Inventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
  • Publication number: 20030065217
    Abstract: A vapor-phase carbonylation method for producing esters and carboxylic acids from reactants comprising lower alkyl alcohols, lower alkyl alcohol generating compounds, and mixtures thereof. The method includes contacting the reactants and carbon monoxide in a carbonylation zone of a carbonylation reactor under vapor-phase conditions with a catalyst having a catalytically effective amount of iridium and tin associated with a solid carrier material.
    Type: Application
    Filed: June 20, 2001
    Publication date: April 3, 2003
    Inventors: Joseph Zoeller, Andy Singleton, Gerald Tustin, Donald Carver
  • Publication number: 20030060660
    Abstract: A vapor-phase carbonylation method for producing esters and carboxylic acids from reactants comprising lower alkyl alcohols, lower alkyl alcohol generating compounds, and mixtures thereof. The method includes contacting the reactants and carbon monoxide in a carbonylation zone of a carbonylation reactor under vapor-phase carbonylation conditions with a catalyst having a catalytically effective amount of a Group VIII metal selected from platinum or palladium, and tungsten which are associated with a solid catalyst support material.
    Type: Application
    Filed: June 20, 2001
    Publication date: March 27, 2003
    Inventors: Joseph Zoeller, Andy Singleton, Gerald Tustin, Donald Carver
  • Publication number: 20030018213
    Abstract: The invention relates to a process for monitoring acetic acid and/or methyl acetate production in a continuous preparative process by the carbonylation of methanol or a carbonylatable derivative of methanol with carbon monoxide in the liquid phase, in the presence of water and a homogeneous catalyst system, carried out in an industrial installation comprising a reaction zone, a flash zone and a distillative purification zone, wherein the reactor temperature and the feed rate of the methanol or carbonylatable derivative in said reactor are brought under the control, preferably via a multivariable predictive controller, of the carbon monoxide feed rate and at least one of the parameters defining the composition of the reaction medium and/or the vents.
    Type: Application
    Filed: September 13, 2001
    Publication date: January 23, 2003
    Inventor: Daniel Thiebaut
  • Publication number: 20020169339
    Abstract: Aliphatic tricarboxylic acids, as exemplified by 9-carboxy-1,18-octadecanedioic acid, may be prepared by the biotransformation of an olefinic monocarboxylic acid such as oleic acid to the corresponding olefinic dicarboxylic acid, preferably 1,18-octadec-9-enedioic acid, in the presence of a strain of yeast, such as a strain of Candida tropicalis, followed by the carboxylation of the olefinic dicarboxylic acid by reaction with carbon monoxide and water in the presence of a catalyst. The product tricarboxylic acids are useful as branching agents for polycarbonates.
    Type: Application
    Filed: January 10, 2002
    Publication date: November 14, 2002
    Inventors: David Paul Mobley, Mohan Mark Amaratunga, John Henry Lobos
  • Publication number: 20010044556
    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.
    Type: Application
    Filed: March 13, 2001
    Publication date: November 22, 2001
    Inventors: Eit Drent, Willem Wabe Jager
  • Patent number: 5981797
    Abstract: Diamine carbamates are prepared by spraying liquid diamine into carbon dioxide gas, in the optional presence of a propellant.
    Type: Grant
    Filed: August 4, 1998
    Date of Patent: November 9, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: John Harry Orth
  • Patent number: 5731486
    Abstract: A method for producing 3-methyl-2-pentene which is substantially free of any other C.sub.6 olefin, except 2-ethyl-1-butene, by first producing a stream that contains 2-ethyl-1-butene from the trimerization of ethylene, and second by recovering the 2-ethyl-1-butene as 3-methyl-2-pentene via etherification, separation of the ether, and decomposition of the ether back to predominantly 3-methyl-2-pentene with some 2-ethyl-1-butene.
    Type: Grant
    Filed: July 17, 1995
    Date of Patent: March 24, 1998
    Assignee: Exxon Chemical Patents Inc
    Inventors: Dan E. Hendriksen, Gerald G. McGlamery, Michael J. Keenan, Derrick D. Pete
  • Patent number: 5463157
    Abstract: A method for producing 3-methyl-2-pentene which is substantially free of any other C.sub.6 olefin, except 2-ethyl-1-butene, by first producing a stream that contains 2-ethyl-1-butene from the trimerization of ethylene, and second by recovering the 2-ethyl-1-butene as 3-methyl-2-pentene via etherification, separation of the ether, and decomposition of the ether back to predominantly 3-methyl-2-pentene with some 2-ethyl-1-butene.
    Type: Grant
    Filed: October 29, 1993
    Date of Patent: October 31, 1995
    Assignee: Exxon Chemical Patents, Inc.
    Inventors: Dan E. Hendriksen, Gerald G. McGlamery, Michael J. Keenan, Derrick D. Pete
  • Patent number: 5455373
    Abstract: A method of producing perfluorocarbon halides in a one-pot reaction is described. The method employs a perfluorocarbon acid, a first halogenating agent and a second halogen which drives the reaction forward. Novel perfluorocarbon halides and a direct method for producing perfluorocarbon hypohalites also are described.
    Type: Grant
    Filed: February 28, 1994
    Date of Patent: October 3, 1995
    Assignee: Exfluor Research Corporation
    Inventor: Hajimu Kawa
  • Patent number: 5202479
    Abstract: A process for preparing glycine which comprises the steps of reacting glycolonitrile, carbon dioxide gas, ammonia and water to obtain a reaction solution containing glycine, concentrating this reaction solution in two steps, recycling a gaseous phase portion formed in a primary concentration step to a reaction zone, and recycling to the reaction zone, a mother liquor left after glycine crystals have been separated from a concentrate obtained in a secondary concentration step.
    Type: Grant
    Filed: February 1, 1991
    Date of Patent: April 13, 1993
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Kenji Fujiwara, Nobutaka Ueda, Yuji Matsuu, Hiroshi Kato, Atsuhiko Hiai
  • Patent number: 5198573
    Abstract: Diesters of hexene-1,6-dioic acids are prepared by reacting at least one 1,2-dialkoxy-3-butene with carbon monoxide in the presence of a catalytically effective amount of a palladium-based catalyst and a halogen compound, in liquid phase, at elevated temperature and at superatmospheric pressure.
    Type: Grant
    Filed: September 19, 1991
    Date of Patent: March 30, 1993
    Assignee: Rhone-Poulenc Chimie
    Inventors: Helene Deweerdt, Jean Jenck, Philippe Kalck, Sylvain Mutez, Robert Perron
  • Patent number: 5189205
    Abstract: A process for preparing isocyanates comprising (a) contacting carbon dioxide and a primary amine in the presence of an aprotic organic solvent and an organic, nitrogenous base to produce the corresponding ammonium carbamate salt, and (b) reacting the ammonium carbamate salt with an electrophilic or oxophilic dehydrating agent to produce the corresponding isocyanate. A second embodiment comprises recovering the ammonium carbamate salt of step (a) prior to reacting the ammonium carbamate salt with an electrophilic or oxophilic dehydrating agent in the presence of an aprotic organic solvent and an organic, nitrogenous base.
    Type: Grant
    Filed: March 16, 1992
    Date of Patent: February 23, 1993
    Assignee: Monsanto Compamy
    Inventors: William D. McGhee, Thomas E. Waldman
  • Patent number: 5124082
    Abstract: A method for preparing .alpha., .beta.-unsaturated carboxylic acids of the formulaR.sub.1 (R.sub.2)C.dbd.C(R.sub.3)CO.sub.2 Hwhere R.sub.1 to R.sub.3 can be hydrogen, fluorine, alkyl, or alkyl containing fluorine, but at least one of R.sub.1 to R.sub.3 is fluorine or alkyl containing fluorine. The method involves reacting an alkenyl halide containing fluorine having the general formulaR.sub.1 (R.sub.2)C.dbd.C(R.sub.3)Xwhere R.sub.1 to R.sub.3 are the same as above, and X is chlorine, bromine, or iodine with carbon dioxide in an aprotic polar organic solvent and in the presence of activated zinc. The activated zinc is activated by pretreatment with a mineral acid or acetic acid. At least one cation is present during the reaction which is an alkali metal ion, alkaline earth metal ion or ammonium ion. The cation is present in an amount of 0.01 to 50 gram atoms per one mol of alkenyl halide containig fluorine. The resulting product is hydrolyzed.
    Type: Grant
    Filed: July 10, 1987
    Date of Patent: June 23, 1992
    Assignee: Tosoh Corporation
    Inventors: Mitsuru Takahashi, Hideo Shuyama, Kiyotaka Oyama
  • Patent number: 4879070
    Abstract: Formate salts of nitrogenous bases containing a tertiary nitrogen atom are prepared by reacting the nitrogenous base with carbon dioxide and hydrogen in the presence of a solvent and a catalyst comprising an inorganic or organometallic compound of rhodium and an organophosphorus compound. The catalysts disclosed effect the reaction at a lower temperature and at higher productivities relative to the Group VIII metal catalysts of the prior art.
    Type: Grant
    Filed: April 7, 1988
    Date of Patent: November 7, 1989
    Assignee: BP Chemicals Limited
    Inventor: Alexander G. Kent
  • Patent number: 4851161
    Abstract: .beta.-substituted polyfluoropropionate salts, derivatives and copolymers and processes for the preparation thereof.
    Type: Grant
    Filed: December 16, 1986
    Date of Patent: July 25, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Carl G. Krespan
  • Patent number: 4578222
    Abstract: A process for preparing a perfluorinated or polyfluorinated aliphatic carboxylic acids wherein a perfluorinated or polyfluorinated aliphatic halide of the formula: R.sub.f X where R.sub.f is a perfluorinated or polyfluorinated aliphatic group and X is a halogen atom is reacted with carbon dioxide in the presence of metal under the irradiation of ultrasound and the reaction product is hydrolyzed to form a perfluorinated or polyfluorinated aliphatic carboxylic acid of the formula: R.sub.f COOH where R.sub.f is the same as defined above.
    Type: Grant
    Filed: August 5, 1985
    Date of Patent: March 25, 1986
    Assignees: Daikin Kogyo Co., Ltd., Toyo Soda Manufacturing Co., Ltd.
    Inventors: Nobuo Ishikawa, Mitsuru Takahashi
  • Patent number: 4474959
    Abstract: Formate salts of nitrogenous bases containing tertiary nitrogen are prepared by reacting the nitrogenous base with carbon dioxide and hydrogen using a soluble transition metal catalyst. For example triethylamine is reacted with carbon dioxide and hydrogen using ruthenium trichloride as catalyst and an isopropanol/water mixture as solvent to yield triethylammonium formate which was separated from the reaction mixture by distillation.
    Type: Grant
    Filed: May 16, 1983
    Date of Patent: October 2, 1984
    Assignee: BP Chemicals Limited
    Inventors: David J. Drury, John E. Hamlin
  • Patent number: 4467089
    Abstract: Novel carbamic and carbonic acid derivatives are provided by simultaneous reaction of a secondary amine and a tertiary amine with carbon dioxide. These derivatives correspond in general to the formula ##STR1## in which R.sub.1 and R.sub.2 may be individual substituents attached to the N or together form with N a heterocyclic moiety; R.sub.3, R.sub.4, R.sub.5 may be individual short chain alkyl or hydroxyalkyl substituents on the N or form therewith a monocyclic or bicyclic heterocyclic moiety. These described compounds find particular use as heat activatable delayed action catalysts especially for use in polyurethane formulations.
    Type: Grant
    Filed: March 4, 1982
    Date of Patent: August 21, 1984
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Ibrahim S. Bechara
  • Patent number: 4234718
    Abstract: Cellulose acetate is produced from methanol, carbon monoxide and cellulose in an integrated series of steps wherein acetic anhydride produced in a first step by the carbonylation of methyl acetate is used to acetylate cellulose to produce cellulose acetate and to co-produce acetic acid is converted to ketene, the ketene is reacted with methanol to produce methyl acetate which is then fed to the first step and carbonylated to produce additional quantities of acetic anhydride.
    Type: Grant
    Filed: June 29, 1979
    Date of Patent: November 18, 1980
    Assignee: Halcon Research and Development Corp.
    Inventor: David Brown
  • Patent number: 4234719
    Abstract: Cellulose acetate is produced from methanol, carbon monoxide and cellulose in an integrated series of steps wherein acetic anhydride produced in a first step by the carbonylation of methyl acetate is used to acetylate cellulose to produce cellulose acetate and to co-produce acetic acid, the co-produced acetic acid is dehydrated and the dehydrated acetic acid reacted with methanol to produce methyl acetate which is then fed to the first step and carbonylated to produce additional quantities of acetic anhydride.
    Type: Grant
    Filed: June 29, 1979
    Date of Patent: November 18, 1980
    Assignee: Halcon Research and Development Corp.
    Inventor: Chee-Gen Wan
  • Patent number: 4221734
    Abstract: A process is disclosed for the preparation of derivatives of perfluoroalkanecarboxylic acids and perfluoroalkanesulphinic acids by reacting a perfluoroalkylhalide having the general formula R.sub.F X, in which X represents an atom of chlorine, bromine, or iodine, and R.sub.F represents an unbranched or branched perfluorinated chain containing from 2 to 12 carbon atoms; with CO.sub.2 or SO.sub.2 in a solvent medium and in the presence of activated or unactivated zinc.
    Type: Grant
    Filed: December 12, 1977
    Date of Patent: September 9, 1980
    Assignee: Produits Chimiques Ugine Kuhlmann
    Inventors: Auguste Commeyras, Hubert Blancou, Andre Lantz
  • Patent number: 4132732
    Abstract: Alpha-formyl acids are prepared by carboxylation of aldehydes in the presence of unsubstituted or substituted alkaline phenates, and of aprotic organic solvents.
    Type: Grant
    Filed: March 2, 1978
    Date of Patent: January 2, 1979
    Assignee: Montedison S.p.A.
    Inventors: Giorgio Bottaccio, Stefano Campolmi, Maria G. Felicioli