Reactant Is An Aldehyde Or Ketone, Or A Compound Having Carbon Double Bonded To Nitrogen (e.g., Ammoxidation Of Acrolein, Etc.) Patents (Class 558/315)
  • Patent number: 10214484
    Abstract: The present invention relates to an improved method for preparing acrolein cyanohydrins from hydrocyanic acid and the corresponding acroleins. The method is characterized in that the acrolein cyanohydrins obtained have a very low hydrocyanic acid content or are free of hydrocyanic acid and are therefore particularly well suited as intermediates for the synthesis of glufosinates.
    Type: Grant
    Filed: March 27, 2018
    Date of Patent: February 26, 2019
    Assignee: Evonik Degussa GmbH
    Inventor: Marianne Omeis
  • Patent number: 9427718
    Abstract: A catalytic reactor including a chamber (1) and separation means (2) arranged inside the chamber (1), said separation means defining at least one reaction area (3) and at least one regeneration area (4), the reaction area (3) being supplied with a reaction flow (15, 16) and connected, at the outlet thereof, to a first gas tapping device (13), the regeneration area (4) being supplied with a regeneration flow (17) and connected, at the outlet thereof, to a second gas tapping device (10), the reactor being suitable for including a fluidized bed of catalyst particles (5) in the reaction area (3), the separation means (2) enabling the catalyst particles to pass from the reaction area (3) to the regeneration area (4), and the reactor making it possible to move catalyst particles into the regeneration area (4) so as to enable the return thereof to the reaction area (3).
    Type: Grant
    Filed: July 9, 2012
    Date of Patent: August 30, 2016
    Assignee: ARKEMA FRANCE
    Inventors: Jean-Luc Dubois, Grégory Patience
  • Patent number: 9187412
    Abstract: The present invention refers to the preparation of 3-cyano-3,5,5-trimethylcyclohexanone (isophorone nitrile, abbreviation IPN) using a calcium alkoxide, particularly calcium ethoxide, as catalyst.
    Type: Grant
    Filed: June 5, 2012
    Date of Patent: November 17, 2015
    Assignee: Evonik Degussa GmbH
    Inventors: Markus Schwarz, Andreas Merkel, Joerg-Joachim Nitz, Gerda Grund
  • Patent number: 9162954
    Abstract: A catalyst composition comprising at least an heteropolyacid deposited on a porous titania carrier. A catalyst composition comprising at least an heteropolyacid in which protons in the heteropolyacid may be partially exchanged by at least one cation selected from elements belonging to Group 1 to Group 16 of the Periodic Table of Elements that have been deposited on a porous titania carrier. A method for preparing the catalyst composition, comprising impregnating a titania carrier with a solution of at least one metal selected from elements belonging to the Group 1 to Group 16 of the Periodic Table of Elements or onium, drying and firing the resulting solid mixture, secondly impregnating the resulting solid mixture with a solution of heteropolyacid, drying, and firing the resulting solid mixture. A process for preparing acrolein and acrylic acid by dehydration of glycerin, carried out in the presence of the catalyst.
    Type: Grant
    Filed: September 19, 2014
    Date of Patent: October 20, 2015
    Assignee: ARKEMA FRANCE
    Inventors: Yasuhiro Magatani, Kimito Okumura, Jean-Luc Dubois, Jean-Francois Devaux
  • Patent number: 8946459
    Abstract: A process for reacting ethylenediamine-formaldehyde adduct (EDFA) and/or ethylene-diamine-monoformaldehyde adduct (EDMFA) with hydrogen cyanide (HCN) in a reactor with limited backmixing at a temperature in the range from 20 to 120° C., wherein the residence time in the reactor is 300 seconds or less.
    Type: Grant
    Filed: August 30, 2012
    Date of Patent: February 3, 2015
    Assignee: BASF SE
    Inventors: Hermann Luyken, Sebastian Ahrens, Gordon Brasche, Jens Baldamus, Robert Baumann, Randolf Hugo, Stephanie Jaegli, Johann-Peter Melder, Jörg Pastre, Boris Buschhaus
  • Publication number: 20150005526
    Abstract: A catalyst composition comprising at least an heteropolyacid deposited on a porous titania carrier. A catalyst composition comprising at least an heteropolyacid in which protons in the heteropolyacid may be partially exchanged by at least one cation selected from elements belonging to Group 1 to Group 16 of the Periodic Table of Elements that have been deposited on a porous titania carrier. A method for preparing the catalyst composition, comprising impregnating a titania carrier with a solution of at least one metal selected from elements belonging to the Group 1 to Group 16 of the Periodic Table of Elements or onium, drying and firing the resulting solid mixture, secondly impregnating the resulting solid mixture with a solution of heteropolyacid, drying, and firing the resulting solid mixture. A process for preparing acrolein and acrylic acid by dehydration of glycerin, carried out in the presence of the catalyst.
    Type: Application
    Filed: September 19, 2014
    Publication date: January 1, 2015
    Applicants: ARKEMA FRANCE, NIPPON KAYAKU KABUSHIKI KAISHA
    Inventors: Yasuhiro MAGATANI, Kimito OKUMURA, Jean-Luc DUBOIS, Jean-Francois DEVAUX
  • Publication number: 20140213811
    Abstract: The present invention relates to the production of acrolein, acrylic acid or methacrylic acid by dehydration reaction of renewable raw material such as glycerin or hydroxycarboxylic acids, in the presence of a novel catalyst system supported on a carrier having a bimodal structure and a high pore volume and distribution. The dehydration reactions can be carried out for longer operation duration, so that acrolein, acrylic acid or methacrylic acid can be produced at higher productivity and for longer running time.
    Type: Application
    Filed: July 27, 2012
    Publication date: July 31, 2014
    Inventors: Jean-Luc Dubois, Kimito Okumura, Yasushi Kobayashi, Ryota Hiraoka
  • Publication number: 20140171676
    Abstract: A method of preparing acrolein from glycerol or glycerine is disclosed. The method includes dehydrating glycerol or glycerine in the presence of a catalyst consisting of at least (a) a mixed oxide of zirconium and at least one metal, said metal being selected from niobium, tantalum and vanadium, or (b) a zirconium oxide and at least one metal oxide, the metal being selected from niobium, tantalum and vanadium, or (c) a silicon oxide and a mixed oxide of zirconium and at least one metal, the metal being selected from tungsten, cerium, manganese, niobium, tantalum, titanium, vanadium and silicon, or (d) a titanium oxide and a mixed oxide of zirconium and at least one metal, said metal being selected from tungsten, cerium, manganese, niobium, tantalum, titanium, vanadium and silicon.
    Type: Application
    Filed: August 27, 2013
    Publication date: June 19, 2014
    Applicants: Centre National De La Recherche Scientifique, Adisseo France S.A.S
    Inventors: Virginie BELLIERE-BACA, STEPHANE LORIDANT, JEAN-MARC MILLET, PASCALINE LAURIOL-GARBEY
  • Patent number: 8604234
    Abstract: The invention relates to a method for preparing acrolein from glycerol or glycerin, according to which dehydration of glycerol or glycerin is carried out in the presence of a catalyst which consists in at least one silica modified with zirconium dioxide, titanium dioxide or tungsten trioxide or any combination of these oxides, and a heteropolyacid. This method may be used for making 3-(methylthio)propionic aldehyde (MMP), 2-hydroxy-4-methylthiobutyronitrile (HMBTN), methionine or its analogs, from acrolein.
    Type: Grant
    Filed: December 21, 2010
    Date of Patent: December 10, 2013
    Assignees: Adisseo France S.A.S., Centre National de la Recherche Scientifique, Universite Lille 1-Sciences et Technologies
    Inventors: Sebastien Paul, Benjamin Katryniok, Franck Dumeignil, Mickael Capron
  • Publication number: 20130324758
    Abstract: The present invention relates to the selective elimination of propanal in acrolein-rich streams to produce acrolein and/or acrylic acid and/or acrylonitrile and/or methylmercaptopropionaldehyde containing low amount of propanal and/or propionic acid and/or propionitrile. One subject of the present invention is a process for manufacturing acrolein comprising a step of selective elimination of propanal in an acrolein-rich stream in contact with a catalyst comprising at least molybdenum. Another subject of the present invention is a process for manufacturing acrylic acid from glycerol including a step of selective elimination of propanal in an acrolein-rich stream in contact with a catalyst comprising at least molybdenum.
    Type: Application
    Filed: January 26, 2012
    Publication date: December 5, 2013
    Applicant: Arkema France
    Inventors: Jean-Francois Devaux, Jean-Luc Dubois
  • Patent number: 8592498
    Abstract: Disclosed herein are a reaction method and a production method of an organic compound which are capable of achieving high reaction selectivity according to the purpose and a high production rate of a target substance. The methods include at least two fluids, wherein at least one kind of the fluids is a fluid containing at least one organic compound and at least one kind of the fluids other than the above fluid is a fluid containing at least one reactant in the form of a liquid or solution, and the respective fluids join together in a thin film fluid foamed between processing surfaces arranged to be opposite to each other so as to be able to approach to and separate from each other, at least one of which rotates relative to the other, whereby an organic reaction is performed in the thin film fluid.
    Type: Grant
    Filed: September 11, 2008
    Date of Patent: November 26, 2013
    Assignee: M. Technique Co., Ltd.
    Inventor: Masakazu Enomura
  • Publication number: 20130310577
    Abstract: Described is a method for the preparation of renin inhibitors such as aliskiren, and intermediates useful therein. The method introduces a nitrogen-containing intermediate such as a lactone of formula (8). with R4 being a branched C3-6 alkyl. In the preparation of the lactone, or related intermediates, a desired stereochemical configuration can be controlled by starting from a chiral aldehyde satisfying formula (10).
    Type: Application
    Filed: July 11, 2013
    Publication date: November 21, 2013
    Applicant: DSM IP ASSETS B.V.
    Inventors: Ben DE LANGE, Anna Maria Cornelia Francisca CASTELIJNS, Johannes Gerardus DE VRIES, Andreas Hendrikus Maria DE VRIES, Jeroen Antonius Franciscus BOOGERS
  • Patent number: 8546601
    Abstract: A storage stable mixture containing 86 to 97% by weight of 2-hydroxy-4-methylthiobutyronitrile, 2 to 14% by weight of water, 0.05 to 0.5% by weight of HCN and having a pH of 1 to 4, measured using a pH electrode at 23° C. is provided. A method to produce the storage stable mixture and its use in manufacture of DL-methionine or 2-hydroxy-4-methylthiobutyric acid is also provided.
    Type: Grant
    Filed: February 22, 2012
    Date of Patent: October 1, 2013
    Assignee: Evonik Degussa GmbH
    Inventors: Dieter Buss, Martin Steurenthaler, Joachim Hans Hasselbach, Michael R. Rinner, Benjamin Fonfe, Martin Koerfer, Stephan Kretz
  • Patent number: 8440852
    Abstract: The invention relates to a process for preparing tetraethylenepentamine (TEPA) by hydrogenation of diethylenetriaminediacetonitrile (DETDN) over a catalyst. If appropriate, DETDN can also be present as a constituent of an amino nitrile mixture which additionally comprises diethylenetriaminemonoacetonitrile (DETMN).
    Type: Grant
    Filed: February 27, 2008
    Date of Patent: May 14, 2013
    Assignee: BASF SE
    Inventors: Kirsten Dahmen, Alfred Oftring, Randolf Hugo, Thilo Hahn, Katrin Baumann, Johann-Peter Melder
  • Publication number: 20130079492
    Abstract: A process for preparing EDDN and/or EDMN by conversion of FA, HCN and EDA, the reaction being effected in the presence of water, and, after the conversion, water being depleted from the reaction mixture in a distillation column, which comprises performing the distillation in the presence of an organic solvent which has a boiling point between water and EDDN and/or EDMN at the distillation pressure existing in the column or which forms a low-boiling azeotrope with water.
    Type: Application
    Filed: August 30, 2012
    Publication date: March 28, 2013
    Applicant: BASF SE
    Inventors: Hermann Luyken, Sebastian Ahrens, Gordon Brasche, Jens Baldamus, Robert Baumann, Randolf Hugo, Stephanie Jaegli, Johann-Peter Melder, Jörg Pastre, Boris Buschhaus
  • Publication number: 20130066100
    Abstract: A process for preparing a catalyst used in a production of acrolein and acrylic acid by dehydration reaction of glycerin, characterized by the steps of mixing a solution of heteropolyacid or constituents of heteropolyacid, a solution of at least one metal selected from elements belonging to Group 1 to Group 16 of the Periodic Table of Elements or its onium and a carrier to obtain a solid substance, and then of effecting at least one time of calcination before said solid substance is used in the dehydration reaction of glycerin. A catalyst obtained by the process for use in a production of acrolein and acrylic acid by dehydration reaction of glycerin. A process for preparing acrolein by catalytic dehydration of glycerin carried out in the presence of the catalyst and under a pressurized condition. A process for preparing acrylic acid obtained by oxydation of acrolein obtained. A process for preparing acrylonitrile obtained by ammoxidation of acrolein obtained.
    Type: Application
    Filed: October 15, 2010
    Publication date: March 14, 2013
    Applicant: NIPPON KAYAKU KABUSHIKI KAISHA
    Inventors: Yasuhiro Magatani, Kimito Okumura, Jean-Luc Dubois
  • Publication number: 20130053584
    Abstract: A process for reacting ethylenediamine-formaldehyde adduct (EDFA) and/or ethylene-diamine-monoformaldehyde adduct (EDMFA) with hydrogen cyanide (HCN) in a reactor with limited backmixing at a temperature in the range from 20 to 120° C., wherein the residence time in the reactor is 300 seconds or less.
    Type: Application
    Filed: August 30, 2012
    Publication date: February 28, 2013
    Applicant: BASF SE
    Inventors: Hermann Luyken, Sebastian Ahrens, Gordon Brasche, Jens Baldamus, Robert Baumann, Randolf Hugo, Stephanie Jaegli, Johann-Peter Melder, Jörg Pastre, Boris Buschhaus
  • Publication number: 20130053536
    Abstract: A process for preparing EDDN and/or EDMN by a) conversion of FA, HCN and EDA, the conversion being effected in the presence of water, b) depleting water from the reaction mixture obtained in stage a), and c) treating the mixture from stage b) with an absorbent in the presence of an organic solvent, wherein the adsorbent is a solid acidic adsorbent.
    Type: Application
    Filed: August 30, 2012
    Publication date: February 28, 2013
    Applicant: BASF SE
    Inventors: Hermann Luyken, Sebastian Ahrens, Gordon Brasche, Jens Baldamus, Robert Baumann, Randolf Hugo, Stephanie Jaegli, Johann-Peter Melder, Jörg Pastre, Boris Buschhaus
  • Publication number: 20130053595
    Abstract: A catalyst composition comprising at least an heteropolyacid deposited on a porous titania carrier. A catalyst composition comprising at least an heteropolyacid in which protons in the heteropolyacid may be partially exchanged by at least one cation selected from elements belonging to Group 1 to Group 16 of the Periodic Table of Elements that have been deposited on a porous titania carrier. A method for preparing the catalyst composition, comprising impregnating a titania carrier with a solution of at least one metal selected from elements belonging to the Group 1 to Group 16 of the Periodic Table of Elements or onium, drying and firing the resulting solid mixture, secondly impregnating the resulting solid mixture with a solution of heteropolyacid, drying, and firing the resulting solid mixture. A process for preparing acrolein and acrylic acid by dehydration of glycerin, carried out in the presence of the catalyst.
    Type: Application
    Filed: September 18, 2009
    Publication date: February 28, 2013
    Applicants: ARKEMA FRANCE, NIPPON KAYAKU KABUSHIKI KAISHA
    Inventors: Yasuhiro Magatani, Kimito Okumura, Jean-Luc Dubois, Jean-Francois Devaux
  • Patent number: 8378136
    Abstract: The subject of the present invention is a process for preparing acrolein by dehydration of glycerol in the presence of a catalyst system comprising oxygen, phosphorus and at least one metal chosen from vanadium, boron or aluminium. The process is preferably carried out in the gas phase in the presence of oxygen starting from aqueous solutions of glycerol.
    Type: Grant
    Filed: October 5, 2009
    Date of Patent: February 19, 2013
    Assignee: Arkema France
    Inventor: Jean-Luc Dubois
  • Publication number: 20120330049
    Abstract: The invention relates to a method for preparing acrolein from glycerol or glycerin, according to which dehydration of glycerol or glycerin is carried out in the presence of a catalyst which consists in at least one silica modified with zirconium dioxide, titanium dioxide or tungsten trioxide or any combination of these oxides, and a heteropolyacid. This method may be used for making 3-(methylthio)propionic aldehyde (MMP), 2-hydroxy-4-methylthiobutyronitrile (HMBTN), methionine or its analogs, from acrolein.
    Type: Application
    Filed: December 21, 2010
    Publication date: December 27, 2012
    Applicants: ADISSEO FRANCE S.A.S., UNIVERSITE LILLE 1 - SCIENCES ET TECHNOLOGIES, CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE
    Inventors: Sebastien Paul, Benjamin Katryniok, Franck Dumeignil, Mickael Capron
  • Patent number: 8309752
    Abstract: A method for producing a compound represented by the following formula (2) (wherein, X, R1 and m represent respectively the same meaning as described below) which comprises reacting a compound represented by the following formula (1) (wherein, X represents an optionally substituted alkyl group or the like. R1 represents an optionally substituted alkyl group or the like. m represents an integer of 0 to 4. When m represents an integer of 2 to 4, R1s may be the same or different from each other) with hydrogen cyanide in an amount of 1.2 to 5 mol with respect to 1 mol of the compound, in the presence of an organic base, in an organic solvent.
    Type: Grant
    Filed: June 24, 2009
    Date of Patent: November 13, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hajime Ishida, Masaji Hirota
  • Publication number: 20120215021
    Abstract: A storage stable mixture containing 86 to 97% by weight of 2-hydroxy-4-methylthiobutyronitrile, 2 to 14% by weight of water, 0.05 to 0.5% by weight of HCN and having a pH of 1 to 4, measured using a pH electrode at 23° C. is provided. A method to produce the storage stable mixture and its use in manufacture of DL-methionine or 2-hydroxy-4-methylthiobutyric acid is also provided.
    Type: Application
    Filed: February 22, 2012
    Publication date: August 23, 2012
    Applicant: Evonik Degussa GmbH
    Inventors: Dieter Buss, Martin Steurenthaler, Hans Joachim Hasselbach, Michael R. Rinner, Benjamin Fonfe, Martin Koerfer, Stephan Kretz
  • Publication number: 20120209007
    Abstract: The present invention relates to titanium catalysts for synthesis reactions produced by bringing a reaction mixture comprising a titanium alkoxide and a ligand in contact with water, wherein the ligand is represented by the general formula (e): wherein R1, R2, R3, and R4 are independently a hydrogen atom, an alkyl group, or the like, and (A) represents a group with two or more carbon atoms. The titanium catalysts may be isolated in solid form and may be stored. The invention further relates to a process for cyanation of imines, wherein the process comprises reacting an imine with a cyanating agent in the presence of the titanium catalyst.
    Type: Application
    Filed: February 11, 2010
    Publication date: August 16, 2012
    Applicants: Agency for Science, Technology and Research, Mitsui Chemicals Inc.
    Inventors: Abdul Majeed Seayad, Balamurugam Ramalingam, Christina Chai, Takushi Nagata, Kazuhiko Yoshinaga, Manabu Wadamoto
  • Publication number: 20120197035
    Abstract: The present invention relates to a novel process for the preparation of cis-1-ammonium-4-alkoxycyclohexanecarbonitrile salts and to novel intermediates or starting compounds which are passed through or used in the process according to the invention.
    Type: Application
    Filed: December 19, 2011
    Publication date: August 2, 2012
    Applicant: Bayer CropScience AG
    Inventors: Frank Volz, Albert Schnatterer, Bernardus Kaptein, Anna Maria Cornelia Francisca Castelijns
  • Publication number: 20110319629
    Abstract: The present invention relates to titanium catalysts for synthesis reactions produced by bringing a reaction mixture comprising a titanium alkoxide and a ligand in contact with water, wherein the ligand is represented by the general formula (e): wherein R1, R2, R3, and R4 are independently a hydrogen atom, an alkyl group, or the like, and (A) represents a group with two or more carbon atoms. The titanium catalysts may be isolated in solid form and may be stored. The invention further relates to a process for cyanation of imines, wherein the process comprises reacting an imine with a cyanating agent in the presence of the titanium catalyst.
    Type: Application
    Filed: February 11, 2010
    Publication date: December 29, 2011
    Applicants: Agency for Science, Technology and Research, Mitsui Chemicals Inc.
    Inventors: Abdul Majeed Seayad, Balamurugam Ramalingam, Christina Chai, Takushi Nagata, Kazuhiko Yoshinaga, Manabu Wadamoto
  • Publication number: 20110288323
    Abstract: The invention relates to a method for preparing acrolein from glycerol or glycerine, comprising dehydrating glycerol or glycerine in the presence of a catalyst consisting of at least a) a mixed oxide of zirconium and at least one metal, said metal being selected from niobium, tantalum and vanadium, b) a zirconium oxide and at least one metal oxide, the metal being selected from niobium, tantalum and vanadium, c) a silicon oxide and a mixed oxide of zirconium and at least one metal, the metal being selected from tungsten, cerium, manganese, niobium, tantalum, titanium, vanadium and silicon, d) a silicon oxide and a mixed oxide of zirconium and at least one metal, the metal being selected from tungsten, cerium, manganese, niobium, tantalum, vanadium and titanium, e) a titanium oxide and a mixed oxide of zirconium and at least one metal, said metal being selected from tungsten, cerium, manganese, niobium, tantalum, titanium, vanadium and silicon, f) a titanium oxide and a mixed oxide or zirconium and at least on
    Type: Application
    Filed: December 16, 2009
    Publication date: November 24, 2011
    Applicants: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, ADISSEO FRANCE S.A.S
    Inventors: Virginie Belliere-Baca, Stephane Loridant, Jean-Marc Millet, Pascaline Lauriol-Garbey
  • Publication number: 20110213174
    Abstract: The subject of the present invention is a process for preparing acrolein by dehydration of glycerol in the presence of a catalyst system comprising oxygen, phosphorus and at least one metal chosen from vanadium, boron or aluminium. The process is preferably carried out in the gas phase in the presence of oxygen starting from aqueous solutions of glycerol.
    Type: Application
    Filed: October 5, 2009
    Publication date: September 1, 2011
    Applicant: Arkema France
    Inventor: Jean-Luc Dubois
  • Publication number: 20110178199
    Abstract: Disclosed herein are a reaction method and a production method of an organic compound which are capable of achieving high reaction selectivity according to the purpose and a high production rate of a target substance. The methods include at least two fluids, wherein at least one kind of the fluids is a fluid containing at least one organic compound and at least one kind of the fluids other than the above fluid is a fluid containing at least one reactant in the form of a liquid or solution, and the respective fluids join together in a thin film fluid foamed between processing surfaces arranged to be opposite to each other so as to be able to approach to and separate from each other, at least one of which rotates relative to the other, whereby an organic reaction is performed in the thin film fluid.
    Type: Application
    Filed: September 11, 2008
    Publication date: July 21, 2011
    Applicant: M. Technique Co., Ltd.
    Inventor: Masakazu Enomura
  • Publication number: 20110118498
    Abstract: A method for producing a compound represented by the following formula (2) (wherein, X, R1 and m represent respectively the same meaning as described below) which comprises reacting a compound represented by the following formula (1) (wherein, X represents an optionally substituted alkyl group or the like. R1 represents an optionally substituted alkyl group or the like. m represents an integer of 0 to 4. When m represents an integer of 2 to 4, R1s may be the same or different from each other) with hydrogen cyanide in an amount of 1.2 to 5 mol with respect to 1 mol of the compound, in the presence of an organic base, in an organic solvent.
    Type: Application
    Filed: June 24, 2009
    Publication date: May 19, 2011
    Inventors: Hajime Ishida, Masaji Hirota
  • Publication number: 20100274038
    Abstract: The invention provides a technology for producing acrolein from glycerol while maintaining high reagent partial pressures, which leads to higher yield. The invention more particularly relates to a method for producing acrolein from glycerol that comprises the intermediate step of forming glycerol and acrolein cyclic acetals.
    Type: Application
    Filed: December 16, 2008
    Publication date: October 28, 2010
    Applicant: Arkema France
    Inventor: Jean-Luc Dubois
  • Publication number: 20100204502
    Abstract: The subject of the present invention is a process for preparing acrolein by dehydration of glycerol in the presence of a catalyst system based on iron phosphorous oxide containing, in addition, one or more elements chosen from alkali metals, alkaline-earth metals, AI, Si, B, Co, Cr, Ni, V, Zn, Zr, Sn, Sb, Ag, Cu, Nb, Mo, Y, Mn, Pt, Rh and the rare earths La, Ce, Sm. The process is preferably carried out in the gas phase in the presence of oxygen starting from aqueous solutions of glycerol. The process according to the invention makes it possible of obtain high acrolein selectivities.
    Type: Application
    Filed: September 11, 2008
    Publication date: August 12, 2010
    Applicant: Arkema France
    Inventor: Jean-Luc Dubois
  • Patent number: 7262316
    Abstract: A novel process for industrially producing an aromatic nitrile compound represented by the following general formula (3): characterized in that one of an aromatic hydroxymethyl compound, an aromatic alkoxymethyl compound and an aromatic aldehyde compound, all represented by the following general formula (1): or a mixture thereof is reacted with an oxidized bromine compound represented by the general formula (2) MBrOm ??(2) in the presence of an acid catalyst and either ammonia or an ammonium sat.
    Type: Grant
    Filed: October 20, 2003
    Date of Patent: August 28, 2007
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventor: Kentaro Kawazoe
  • Patent number: 7102025
    Abstract: In the production method of the invention, a cyclic aldehyde having an alkyl group and/or a cycloalkyl group directly bonded to a skeletal ring and a formyl group directly bonded to the skeletal ring is brought into contact with ammonia and oxygen in vapor phase in the presence of a catalyst. As a result thereof, the formyl group is selectively ammoxidized into a cyano group to convert the cyclic aldehyde into a corresponding cyclic nitrile. The method enables a long-term, high-yield production of the cyclic nitrile using a reduced amount of ammonia.
    Type: Grant
    Filed: September 29, 2004
    Date of Patent: September 5, 2006
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Kentaro Kataoka, Yoshikazu Shima, Kenji Inamasa
  • Patent number: 7098357
    Abstract: The present invention relates to a process for the dehydration of organic compounds to give unsaturated compounds.
    Type: Grant
    Filed: March 1, 2001
    Date of Patent: August 29, 2006
    Assignee: Merck Patent GmbH
    Inventors: Hanns Wurziger, Guido Pieper, Norbert Schwesinger
  • Patent number: 7014796
    Abstract: Nonlinear optically active compounds, methods for making nonlinear optically active compounds, compounds useful for making nonlinear optically active compounds, methods for making compounds useful for making nonlinear optically active compounds, macrostructures that include nonlinear optically active components, and devices including the nonlinear optically active compounds and the macrostructures.
    Type: Grant
    Filed: January 15, 2003
    Date of Patent: March 21, 2006
    Assignee: University of Washington
    Inventors: Kwan-Yue Jen, Hong Ma, Sen Liu, Larry R. Dalton
  • Patent number: 6897332
    Abstract: A process for cyanating an aldehyde is provided. The process comprises reacting the aldehyde with: i) a cyanide source which does not comprise a Si—CN bond or a C—(C?O)—CN moiety; and ii) a substrate susceptible to nucleophilic attack not comprising a halogen leaving group; in the presence of a chiral catalyst. Preferably, the chiral catalyst is a chiral vanadium or titanium catalyst. The cyanide source is preferably an alkali metal cyanide and the substrate susceptible to nucleophilic attack not comprising a halogen leaving group is a carboxylic anhydride.
    Type: Grant
    Filed: January 31, 2003
    Date of Patent: May 24, 2005
    Assignees: Nesmeyanov Institute of Organoelement Compounds, King's College London
    Inventors: Yuri Belokon, Michael North
  • Patent number: 6875883
    Abstract: There is a significant demand for organic nitriles, based on their versatility in reactions. Compounds prepared from nitriles have properties including superoxide inhibition, ferrielectric liquid crystal dopant, antipicornaviral agents, anti-inflammatory agents, anti-asthma agents, and fibringoen antagonists. The present invention discloses a facile synthesis for 2,4-dihydroxybenzonitrile, and ethers and diethers thereof, from 2,4-dihydroxybenzaldehyde or 2,4-dimethoxybenzaldehyde. The present invention also discloses a method of preparing a class of iron chelating agents related to desferrithiocin, all of which contain a thiazoline ring. In this method, 2,4-dihydroxybenzonitrile is condensed with (S)-2-methylcysteine.
    Type: Grant
    Filed: May 15, 2003
    Date of Patent: April 5, 2005
    Assignee: Genzyme Corporation
    Inventors: Mukund S. Chorghade, Mukund K. Gurjar, Joseph Cherian
  • Patent number: 6852873
    Abstract: Process for preparing compounds of the formula (I) where R1, R2 and R3 are independently hydrogen, alkyl or cycloalkyl, characterized in that an aldehyde of the formula (II) is reacted with CH2(CN)2 in the presence of butanol.
    Type: Grant
    Filed: August 19, 2002
    Date of Patent: February 8, 2005
    Assignee: Bayer Aktiengesellschaft
    Inventors: Josef-Walter Stawitz, Stephan Michaelis, Christoph Thiebes
  • Patent number: 6828455
    Abstract: Process for preparing compounds of the formula (I) characterized in that an acrylic compound of the formula is reacted with an amine of the formula in which R1, R2, R3, R4 and Z are as defined in the description.
    Type: Grant
    Filed: January 15, 2003
    Date of Patent: December 7, 2004
    Assignee: Bayer Aktiengesellschaft
    Inventors: Josef-Walter Stawitz, Ulrich Feldhues
  • Patent number: 6822110
    Abstract: The present invention describes a process for preparing isophoronenitrile by adding HCN to isophorone. The catalyst used is CaO which has a BET surface area of >1.5 m2/g. The use of such a catalyst achieves high yields and selectivities.
    Type: Grant
    Filed: November 6, 2003
    Date of Patent: November 23, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Dagmar Pascale Kunsmann-Keitel, Gerold Braun, Ingo Münster, Klaus Mundinger, Gunter Scherhag, Wolfgang Siegel
  • Patent number: 6667020
    Abstract: A process increasing the yield of both HCN and acetonitrile produced during the manufacture of acrylonitrile comprising introducing a hydrocarbon selected from the group consisting of propylene and propane, a crude ketone and/or a mixture of at least two ketones, ammonia and air, into a reaction zone containing an ammoxidation catalyst, reacting the. hydrocarbon, the ketone, ammonia and oxygen over said catalyst at an elevated temperature to produce acrylonitrile, hydrogen cyanide and acetonitrile, and recovering the acrylonitrile, hydrogen cyanide and acetonitrile from the reactor.
    Type: Grant
    Filed: December 10, 2001
    Date of Patent: December 23, 2003
    Assignee: The Standard Oil Company
    Inventors: Michael J. Seely, Sanjay Purushottam Godbole, Dev Dhanaraj Suresh
  • Patent number: 6504043
    Abstract: The present invention relates to a process for preparing a colour-stable, aqueous dimethylaminoacetonitrile solution from a formaldehyde source, dimethylamine and hydrocyanic acid, wherein the reaction mixture contains 2,4-diamino-6-phenyl-1,3,5-triazine(benzoguanamine) in a concentration of from 0.001 to 5% by weight, based on formaldehyde, prior to the reaction and the starting substances are used stoichiometrically or in a ratio of 0.98-1.02 mol of formaldehyde and 0.95-1.10 mol of dimethylamine per mol of hydrocyanic acid. The resulting product remains colour-stable without a further purification step even after prolonged storage.
    Type: Grant
    Filed: March 5, 2001
    Date of Patent: January 7, 2003
    Assignee: Clariant GmbH
    Inventors: Rainer Fell, Götz Wilbert, Thomas Stährfeldt
  • Patent number: 6448416
    Abstract: The present invention is directed to dicyanomethylenedihydrofuran-based electron acceptors which can be used in the preparation of polymeric thin films for waveguide media, and methods of making the same.
    Type: Grant
    Filed: June 16, 2000
    Date of Patent: September 10, 2002
    Assignee: Corning Incorporated
    Inventors: Mingqian He, Thomas M. Leslie
  • Patent number: 6413485
    Abstract: A process increasing the yield of both HCN and acetonitrile produced during the manufacture of acrylonitrile comprising introducing a hydrocarbon selected from the group consisting of propylene and propane, a crude ketone and/or a mixture of at least two ketones, ammonia and air, into a reaction zone containing an ammoxidation catalyst, reacting the hydrocarbon, the ketone, ammonia and oxygen over said catalyst at an elevated temperature to produce acrylonitrile, hydrogen cyanide and acetonitrile, and recovering the acrylonitrile, hydrogen cyanide and acetonitrile from the reactor.
    Type: Grant
    Filed: May 27, 1999
    Date of Patent: July 2, 2002
    Assignee: The Standard Oil Company
    Inventors: Michael J. Seely, Sanjay Purushottam Godbole, Dev Dhanaraj Suresh
  • Publication number: 20020004027
    Abstract: A process increasing the yield of both HCN and acetonitrile produced during the manufacture of acrylonitrile comprising introducing a hydrocarbon selected from the group consisting of propylene and propane, a crude ketone and/or a mixture of at least two ketones, ammonia and air, into a reaction zone containing an ammoxidation catalyst, reacting the hydrocarbon, the ketone, ammonia and oxygen over said catalyst at an elevated temperature to produce acrylonitrile, hydrogen cyanide and acetonitrile, and recovering the acrylonitrile, hydrogen cyanide and acetonitrile from the reactor.
    Type: Application
    Filed: May 27, 1999
    Publication date: January 10, 2002
    Inventors: MICHAEL J. SEELY, SANJAY PURUSHOTTAM GODBOLE, DEV DHANARAJ SURESH
  • Patent number: 6248918
    Abstract: An optically active binaphthyl compound of the formula (1): wherein R1 is a C1-6 alkyl group, an aryl group or an aryl C1-6 alkyl group, X is an oxygen atom or a sulfur atom, R2 is a hydrogen atom, a C1-6 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group or a halogen atom, each of L1 and L2 is a hydrogen atom, or L1 and L2 together form MY wherein M is a rare earth element or a Group 13 element, and Y is a C1-6 alkoxy group, a C1-6 alkylcarbonyloxy group or a halogen atom, and m is an integer of from 1 to 3.
    Type: Grant
    Filed: October 1, 1999
    Date of Patent: June 19, 2001
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Masakatsu Shibasaki, Motomu Kanai, Yoshitaka Hamashima
  • Patent number: 6204406
    Abstract: (S)-cyanohydrins are produced by asymmetric addition of hydrogen cyanide to aldehydes in the presence of a catalyst of cyclo-[(S)-leucyl-(S)-histidyl].
    Type: Grant
    Filed: May 11, 1994
    Date of Patent: March 20, 2001
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Atsunori Mori, Yoshitaka Ikeda, Koichi Kinoshita, Shohei Inoue
  • Patent number: 6191306
    Abstract: Disclosed is a process for the preparation of cyclopropylglycine by a 5-step process wherein cyclopropanecarboxaldehyde is reacted with an &agr;-aminoalkylaromatic compound to obtain an imine which is reacted with a cyanide to produce an aminonitrile compound; the aminonitrile compound is hydrolyzed to the corresponding aminocarboxylic acid and finally the arylalkyl residue is removed from the amino group by hydrogenolysis.
    Type: Grant
    Filed: August 3, 1999
    Date of Patent: February 20, 2001
    Assignee: Eastman Chemical Company
    Inventors: Daniel John Bayston, Jonathan Luke William Griffin, Arne Gruman, Mario Eugenio Cosimino Polywka, Ronald Michael Scott
  • Patent number: 6114565
    Abstract: A process for obtaining a nitrile represented by formula RCN, comprising contacting a corresponding aldehyde represented by formula RCHO with (i) ammonia or ammonium hydroxide, and (ii) hydrogen peroxide, in the presence of a transition metal or a transition metal compound.
    Type: Grant
    Filed: September 3, 1999
    Date of Patent: September 5, 2000
    Assignee: Millennium Specialty Chemicals
    Inventors: Mark B. Erman, Joe W. Snow, Melissa J. Williams