Aldehyde Group In Acid Moiety Patents (Class 560/177)
  • Patent number: 10745369
    Abstract: An integrated process is useful for producing 2,5-furandicarboxylic acid (FDCA) and/or a derivative thereof from a six-carbon sugar-containing feed. The process includes a) dehydrating a feed containing a six-carbon sugar unit, in the presence of a bromine source and of a solvent, to generate an oxidation feed that contains at least one of 5-hydroxymethylfurfural (HMF) and/or a derivative or derivatives of HMF in the solvent, together with at least one bromine containing species; b) contacting the oxidation feed from step (a) with a metal catalyst and with an oxygen source under oxidation conditions to produce an oxidation product mixture of at least FDCA and/or a derivative thereof, the solvent, and a residual catalyst: c) purifying and separating the mixture obtained in step (b) to obtain FDCA and/or a derivative thereof and the solvent; and d) recycling at least a portion of the solvent obtained in step (c) to step (a).
    Type: Grant
    Filed: November 26, 2019
    Date of Patent: August 18, 2020
    Assignees: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC, ARCHER DANIELS MIDLAND COMPANY
    Inventors: Stephen J. Howard, Kristina A. Kreutzer, Bhuma Rajagopalan, Eric R. Sacia, Alexandra Sanborn, Brennan Smith
  • Patent number: 10526356
    Abstract: The invention relates to bisphosphites having 2,4-tert-butylphenyl units and a method for the preparation thereof. Furthermore, the invention relates to the use of the compounds as ligands in a ligand-metal complex. The compound, and also the complex, may be used as a catalytically active composition in hydroformylation reactions.
    Type: Grant
    Filed: November 7, 2017
    Date of Patent: January 7, 2020
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Dieter Hess
  • Publication number: 20150031887
    Abstract: An organocatalyst for oxidizing alcohols in which a primary alcohol is selectively oxidized in a polyol substrate having a plurality of alcohols under environmentally-friendly conditions. The organic oxidation catalyst has an oxygen atom bonded to a nitrogen atom of an azanoradamantane skeleton and at least one alkyl group at positions 1 and 5. The oxidation catalyst has higher activity than TEMPO, which is an existing oxidation catalyst, in the selective oxidation reaction of primary alcohols, and better selectivity than AZADO and 1-Me-AZADO. This DMN-AZADO can be applied to the selective oxidation reaction of primary alcohols that contributes to shortening the synthesizing process for pharmaceuticals, pharmaceutical raw materials, agricultural chemicals, cosmetics, organic materials, and other such high value-added organic compounds.
    Type: Application
    Filed: February 22, 2013
    Publication date: January 29, 2015
    Inventors: Yoshiharu Iwabuchi, Masatoshi Shibuya, Ryusuke Doi
  • Publication number: 20140228579
    Abstract: The present application relates to methods for the catalytic reduction of acid chlorides and/or imidoyl chlorides. The methods comprise reacting the acid chloride or imidoyl chloride with a silane reducing agent in the presence of a catalyst such as [Cp(Pri3P)Ru(NCMe)2]+[PF6]?.
    Type: Application
    Filed: September 11, 2013
    Publication date: August 14, 2014
    Applicant: Brock Unviersity
    Inventors: Georgii Nikonov, Dmitry Gutsulyak, Sun Hwa Lee
  • Patent number: 8801939
    Abstract: A method for increasing ozone concentration in a liquid can include: providing a gas having ozone; introducing the ozone-containing gas into a liquid, wherein the liquid and ozone combination has a temperature between about 0.8 and about 1.5 times the critical temperature of ozone; and increasing isothermally, the pressure of the ozone-containing gas above the liquid to about 0.3 to about 5 times the critical pressure of ozone so as to increase the ozone concentration in the liquid. The temperature is expressed in absolute units (Kelvin or Rankin). The method can be used for removing ozone from a gas or for purifying ozone. The liquid having a high ozone concentration can be used for ozonolysis of a substrate.
    Type: Grant
    Filed: April 19, 2013
    Date of Patent: August 12, 2014
    Assignees: University of Kansas, Archer Daniels Midland Company
    Inventors: Bala Subramaniam, Daryle Busch, Andrew M. Danby, Thomas P Binder
  • Patent number: 8729294
    Abstract: The present invention provides a production method of optically active 3-substituted-3-formyl-2-hydroxypropanoic acid compound (4), which includes a step of reacting glyoxylic acid compound (1-1) or (1-2) with aldehyde (2) in the presence of optically active pyrrolidine compound (3); wherein each symbol is as defined in the specification.
    Type: Grant
    Filed: May 30, 2011
    Date of Patent: May 20, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Yujiro Hayashi
  • Patent number: 8586632
    Abstract: The invention provides oleocanthal analogs and methods of using oleocanthals in various formulations including, food additives; pharmaceuticals; cosmetics; animal repellants; and discovery tools for mammalian irritation receptor genes, gene products, alleles, splice variants, alternate transcripts and the like.
    Type: Grant
    Filed: April 25, 2007
    Date of Patent: November 19, 2013
    Assignees: Monell Chemical Senses Center, The Trustees of The University of Pennsylvania
    Inventors: Catherine Peyrot Des Gachons, Jeffrey B. Sperry, Bruce Bryant, Paul A. S. Breslin, Amos B. Smith, III, Gary K. Beauchamp
  • Publication number: 20130137880
    Abstract: The present invention provides a production method of optically active 3-substituted-3-formyl-2-hydroxypropanoic acid compound (4), which includes a step of reacting glyoxylic acid compound (1-1) or (1-2) with aldehyde (2) in the presence of optically active pyrrolidine compound (3); wherein each symbol is as defined in the specification.
    Type: Application
    Filed: May 30, 2011
    Publication date: May 30, 2013
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventor: Yujiro Hayashi
  • Patent number: 8425784
    Abstract: A method for increasing ozone concentration in a liquid can include: providing a gas having ozone; introducing the ozone-containing gas into a liquid, wherein the liquid and ozone combination has a temperature between about 0.8 and about 1.5 times the critical temperature of ozone; and increasing isothermally, the pressure of the ozone-containing gas above the liquid to about 0.3 to about 5 times the critical pressure of ozone so as to increase the ozone concentration in the liquid. The temperature is expressed in absolute units (Kelvin or Rankin). The method can be used for removing ozone from a gas or for purifying ozone. The liquid having a high ozone concentration can be used for ozonolysis of a substrate.
    Type: Grant
    Filed: November 4, 2008
    Date of Patent: April 23, 2013
    Assignees: University of Kansas, Archer Daniels Midland Company
    Inventors: Bala Subramaniam, Daryle Busch, Andrew M. Danby, Thomas P. Binder
  • Publication number: 20130005807
    Abstract: The objective of the present invention is to provide an antimicrobial composition that can be safely used with a broad range of foods and beverages, cosmetics, drugs, and other similar products while showing growth inhibition activity against a wide variety of microorganisms. The present invention relates to the antimicrobial composition comprising at least one cooling agent selected from the group consisting of menthyl 3-hydroxybutanoate, 2-methyl-3-(menthoxy)propane-1,2-diol, 2-(menthoxy)ethanol, 3-menthoxypropan-1-ol, 2-(2-menthoxyethoxy)ethanol, and menthyl glyoxylate.
    Type: Application
    Filed: June 29, 2012
    Publication date: January 3, 2013
    Applicant: TAKASAGO INTERNATIONAL CORPORATION
    Inventors: Kenya ISHIDA, Tomoko YAMAMOTO, Miho SUZUKI
  • Publication number: 20120198590
    Abstract: The disclosure pertains to isolated white pine toxigenic endophytes and the compounds produced by the fungal endophytes as well as methods and uses of the white pine endophytes. The isolated white pine toxigenic endophytes are useful for preparing white pine seedlings and plants that have increased tolerance to a pest and are prepared by inoculating a white pine seedling during the susceptible time window.
    Type: Application
    Filed: January 27, 2012
    Publication date: August 2, 2012
    Applicant: J.D. IRVING, LIMITED
    Inventors: John David Miller, Greg William Adams, Mark Sumarah
  • Publication number: 20110124904
    Abstract: A process for the production of 4-acetoxybutyraldehyde is described. The process comprises reacting allyl acetate with a mixture of carbon monoxide and hydrogen in the presence of a solvent and a catalyst comprising a rhodium complex and a diphosphine. The diphoshine is a substituted or unsubstituted 2,2?-bis(dihydrocarbylphosphino)diphenyl ether. The process gives a high ratio of 4-acetoxybutyraldehyde:3-acetoxy-2-methylpropionaldehyde.
    Type: Application
    Filed: November 25, 2009
    Publication date: May 26, 2011
    Inventor: Daniel F. White
  • Publication number: 20110020424
    Abstract: The invention provides oleocanthal analogs and methods of using oleocanthals in various formulations including, food additives; pharmaceuticals; cosmetics; animal repellants; and discovery tools for mammalian irritation receptor genes, gene products, alleles, splice variants, alternate transcripts and the like.
    Type: Application
    Filed: April 25, 2007
    Publication date: January 27, 2011
    Inventors: Catherine Peyrot Des Gachons, Jeffrey B. Sperry, Bruce Bryant, Paul A.S. Breslin, Amos B. Smith, III, Gary K. Beauchamp
  • Publication number: 20110004002
    Abstract: A process for preparing alkyl 2-alkoxymethylene-4,4-difluoro-3-oxobutyrates (VI) where R is methyl or ethyl, from crude reaction mixtures of alkyl 4,4-difluoroacetoacetates (I) by a) reacting where M is a sodium or potassium ion, and without additional solvent to form an enolate (V) b) releasing the corresponding alkyl 4,4-difluoroacetoacetate (I) from the enolate (V) by means of acid, c) removing the salt formed from cation M and acid anion as a solid and d) converting (I), without isolation from the crude reaction mixture, to the alkyl 2-alkoxymethylene-4,4-difluoro-3-oxobutyrate (VI), and the use of (VI) for preparing 1-methyl-3-difluoromethyl-pyrazol-3-ylcarboxyates VII
    Type: Application
    Filed: February 27, 2009
    Publication date: January 6, 2011
    Applicant: BASF SE
    Inventors: Volker Maywald, Sebastian Peer Smidt, Bernd Wolf, Christopher Koradin, Thomas Zierke, Michael Rack, Michael Keil
  • Publication number: 20090259065
    Abstract: The invention is directed to methods of making organic compounds by metathesis and hydrocyanation. The method of the invention may be used, for example, to make industrial important organic compounds such as diacids, diesters, acid-amines, acid-alcohols, acid-nitriles, ester-amines, ester-alcohols, and ester-nitriles.
    Type: Application
    Filed: April 10, 2009
    Publication date: October 15, 2009
    Inventors: Timothy W. Abraham, Hiroki Kaido, Choon Woo Lee, Richard L. Pederson, Yann Schrodi, Michael John Tupy, Alexandre A. Pletnev
  • Publication number: 20090118498
    Abstract: A method for increasing ozone concentration in a liquid can include: providing a gas having ozone; introducing the ozone-containing gas into a liquid, wherein the liquid and ozone combination has a temperature between about 0.8 and about 1.5 times the critical temperature of ozone; and increasing isothermally, the pressure of the ozone-containing gas above the liquid to about 0.3 to about 5 times the critical pressure of ozone so as to increase the ozone concentration in the liquid. The temperature is expressed in absolute units (Kelvin or Rankin). The method can be used for removing ozone from a gas or for purifying ozone. The liquid having a high ozone concentration can be used for ozonolysis of a substrate.
    Type: Application
    Filed: November 4, 2008
    Publication date: May 7, 2009
    Inventors: Bala Subramaniam, Daryle Busch, Andrew M. Danby, Thomas P. Binder
  • Patent number: 7432392
    Abstract: A therapeutic agent for hyperlipidemia which has no side effects on the liver unlike conventional MTP inhibitors and has excellent MTP inhibitory activity. Also, provided is an ester compound represented by the general formula (1): or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: February 27, 2006
    Date of Patent: October 7, 2008
    Assignee: Japan Tobacco Inc.
    Inventors: Atsushi Hagiwara, Taku Ikenogami, Yasuko Mera, Yukako Sumida, Akio Iida, Toshio Taniguchi, Mitsuru Takahashi
  • 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: 6521752
    Abstract: The invention relates to a process to separate linear 5-formylvalerate compound from a crude mixture comprising 5-formylvalerate compound and 2-, 3- and/or 4-formylvalerate compound by vacuum distillation, wherein the distillation is performed in the presence of a phenolic compound with a boiling point which is at least 10° C. higher than the boiling point of the 5-formylvalerate at 0.1-100 kPa.
    Type: Grant
    Filed: August 16, 2001
    Date of Patent: February 18, 2003
    Assignees: DSM N.V., E.I. Dupont de Nemours and Co.
    Inventors: Onko J. Gelling, Peter C. Borman
  • Patent number: 6489505
    Abstract: There is provided a process for producing 3,3-dimethyl-2-formylcyclopropanecarboxylic ester of formula (1): wherein R represents an alkyl group, a cycloalkyl group or an optionally substituted aralkyl group, which comprises reacting chrysanthemic acid ester of formula (2): wherein R represents the same meaning as that described above, with hydrogen peroxide in the presence of at least one catalyst selected from tungstic oxide, tungstic acid, tugstate, alkylrhenium trioxide, molybdic oxide, molybdate, a heteropoly acid comprising a hetero atom selected from a phosphorus, boron or silicone atom and a poly atom selected from tungsten or molybdenum and a salt of said heteropoly acid.
    Type: Grant
    Filed: January 26, 2001
    Date of Patent: December 3, 2002
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Hagiya, Ichiro Komoto, Akio Kurihara
  • Patent number: 6407282
    Abstract: Monoester monoacid fluoride of dicarboxylic acid is produced by allowing dicaroxylic acid fluoride represented by the following general formula: FOCCF(CF3)OCF2(A)p(CF2)qCOF where A is a bifunctional perfluorinated group having 1 to 10 carbon atoms; p is 0 or 1; and q is 0 or an integer of 1-10, to react with an alcohol having at least 3 carbon atoms, thereby esterifying the terminal CF2COF group. Such selective monoesterification reaction is effective for separation and purification of a dicarboxylic acid difluoride isomer mixture comprising symmetrical dicarboxylic acid difluoride and asymmetrical dicarboxylic acid difluoride.
    Type: Grant
    Filed: October 30, 2000
    Date of Patent: June 18, 2002
    Assignee: Nippon Mektron, Limited
    Inventors: Hiroaki Murata, Sunao Ikeda, Satoru Saito
  • Patent number: 6313343
    Abstract: Alkylene glycol is oxidized in a vapor phase in the presence of alcohol (a), oxygen, and a catalyst (a) (primary reaction). &agr;-oxoaldehyde, and alcohol (b) or olefin, are oxidized in a vapor phase in the presence of oxygen and a catalyst (b) (secondary reaction). A molar ratio of the alkylene glycol to the alcohol (a) is preferably in a range of 1/100 to 5/1. It is preferable that one same compound is used as the alcohol (a) and the alcohol (b). In the case where the primary and secondary reactions are successively executed, a reaction device in which a primary reactor and a secondary reactor are connected in a two-stage connection type is preferably used. This ensures that a method is provided that is capable of producing &agr;-oxoaldehyde at a higher yield than conventionally, and further, that is capable of stably obtaining an &agr;-oxoaldehyde solution or gas with a higher concentration than conventionally.
    Type: Grant
    Filed: January 7, 2000
    Date of Patent: November 6, 2001
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Yoshitaka Arita, Akihiko Ohta, Noboru Saito, Kimio Ariyoshi
  • Patent number: 6310260
    Abstract: This invention relates to a process for separating one or more organophosphorus ligand degradation products, one or more reaction byproducts and one or more products from a continuously generated reaction product fluid comprising one or more unreacted reactants, a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more organophosphorus ligand degradation products, said one or more reaction byproducts, said one or more products, one or more polar solvents and one or more nonpolar solvents by phase separation wherein (i) the selectivity of the polar phase for the organophosphorus ligand with respect to the one or more products is expressed by a partition coefficient ratio Ef1 which is a value greater than about 2.5, (ii) the selectivity of the polar phase for the organophosphorus ligand with respect to the one or more organophosphorus ligand degradation products is expressed by a partition coefficient ratio Ef2 which is a value greater than about 2.
    Type: Grant
    Filed: March 15, 2000
    Date of Patent: October 30, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John Nicholas Argyropoulos, Jeffrey Scott Kanel, Michael Leo Tulchinsky, David James Miller, Donald Lee Morrison, Paul Foley, David Robert Bryant, Ailene Gardner Phillips, Brian Michael Roesch, John Robert Briggs, Max Min Lee, John Michael Maher
  • Patent number: 6307109
    Abstract: This invention relates to a process for separating one or more products from a reaction product fluid comprising a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more products, one or more nonpolar reaction solvents and one or more polar reaction solvents, in which said reaction product fluid exhibits phase behavior depicted by FIG. 1, wherein said process comprises (1) supplying said reaction product fluid from a reaction zone to a separation zone, (2) controlling concentration of said one or more nonpolar reaction solvents and said one or more polar reaction solvents, temperature and pressure in said separation zone sufficient to obtain by phase separation two immiscible liquid phases depicted by regions 2, 4 and 6 of FIG. 1 comprising a polar phase and a nonpolar phase and to prevent or minimize formation of three immiscible liquid phases depicted by region 5 of FIG. 1 and one homogeneous liquid phase depicted by regions 1, 3 and 7 of FIG.
    Type: Grant
    Filed: March 15, 2000
    Date of Patent: October 23, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Jeffrey Scott Kanel, David Robert Bryant, Brian Michael Roesch, Ailene Gardner Phillips
  • Patent number: 6307110
    Abstract: This invention relates to a process for separating one or more organophosphorus ligand degradation products, one or more reaction byproducts and one or more products from a continuously generated reaction product fluid comprising one or more unreacted reactants, a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more organophosphorus ligand degradation products, said one or more reaction byproducts, said one or more products, one or more nonpolar solvents and one or more polar solvents by phase separation wherein (i) the selectivity of the nonpolar phase for the organophosphorus ligand with respect to the one or more products is expressed by a partition coefficient ratio Ef1which is a value greater than about 2.5, (ii) the selectivity of the nonpolar phase for the organophosphorus ligand with respect to the one or more organophosphorus ligand degradation products is expressed by a partition coefficient ratio Ef2 which is a value greater than about 2.
    Type: Grant
    Filed: March 15, 2000
    Date of Patent: October 23, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John Nicholas Argyropoulos, Jeffrey Scott Kanel, Michael Leo Tulchinsky, David James Miller, Donald Lee Morrison, Paul Foley, David Robert Bryant, Ailene Gardner Phillips, Brian Michael Roesch, John Robert Briggs, Max Min Lee, John Michael Maher
  • Patent number: 6307108
    Abstract: This invention relates to a process for separating one or more organophosphorus ligand degradation products, one or more reaction byproducts and one or more formylester products from a reaction product fluid comprising one or more unreacted unsaturated ester reactants, a metal-organophoshorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more organophosphorus ligand degradation products, said one or more reaction byproducts, said one or more products, a nonpolar solvent and a polar solvent by phase separation wherein (i) the selectivity of the nonpolar phase for the organophosphorus ligand with respect to the one or more products is expressed by a partition coefficient ratio Ef1 which is a value greater than about 2.5 (ii) the selectivity of the nonpolar phase for the organophosphorus ligand with respect to the one or more organophosphorus ligand degradation products is expressed by a partition coefficient ratio Ef2 which is a value greater than about 2.
    Type: Grant
    Filed: March 15, 2000
    Date of Patent: October 23, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John Nicholas Argyropoulos, Jeffrey Scott Kanel, Michael Leo Tulchinsky, David James Miller, Donald Lee Morrison, Paul Foley, David Robert Bryant
  • Patent number: 6303830
    Abstract: This invention relates to a process for separating one or more organophosphorus ligand degradation products, one or more reaction byproducts and one or more formylester products from a reaction product fluid comprising one or more unreacted unsaturated ester reactants, a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more organophosphorus ligand degradation products, said one or more reaction byproducts, said one or more products, a polar solvent and a nonpolar solvent by phase separation wherein(i) the selectivity of the polar phase for the organophosphorus ligand with respect to the one or more products is expressed by a partition coefficient ratio Ef1 which is a value greater than about 2.5, (ii) the selectivity of the polar phase for the organophosphorus ligand with respect to the one or more organophosphorus ligand degradation products is expressed by a partition coefficient ratio Ef2 which is a value greater than about 2.
    Type: Grant
    Filed: March 15, 2000
    Date of Patent: October 16, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John Nicholas Argyropoulos, Jeffrey Scott Kanel, Michael Leo Tulchinsky, David James Miller, Donald Lee Morrison, Paul Foley, David Robert Bryant
  • Patent number: 6303829
    Abstract: This invention relates to a process for separating one or more products from a reaction product fluid comprising a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more products, one or more nonpolar reaction solvents and one or more polar reaction solvents, wherein said process comprises (1) subjecting said reaction product fluid to fractional countercurrent extraction with at least two immiscible extraction solvents, said at least two immiscible extraction solvents comprising at least one nonpolar extraction solvent and at least one polar extraction solvent, to obtain a nonpolar phase comprising said metal-organophosphorus ligand complex catalyst, said optionally free organophosphorus ligand, said one or more nonpolar reaction solvents and said at least one nonpolar extraction solvent and a polar phase comprising said one or more products, said one or more polar reaction solvents and said at least one polar extraction solvent, and (2) recovering said polar
    Type: Grant
    Filed: March 15, 2000
    Date of Patent: October 16, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Jeffrey Scott Kanel, John Nicholas Argyropoulos, Ailene Gardner Phillips, Brian Michael Roesch, John Robert Briggs, Max Min Lee, John Michael Maher, David Robert Bryant
  • Patent number: 6294700
    Abstract: This invention relates to a process for separating one or more products from a reaction product fluid comprising a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more products, one or more polar reaction solvents and one or more nonpolar reaction solvents, wherein said process comprises (1) subjecting said reaction product fluid to fractional countercurrent extraction with at least two immiscible extraction solvents, said at least two immiscible extraction solvents comprising at least one polar extraction solvent and at least one nonpolar extraction solvent, to obtain a polar phase comprising said metal-organophosphorus ligand complex catalyst, said optionally free organophosphorus ligand, said one or more polar reaction solvents and said at least one polar extraction solvent and a nonpolar phase comprising said one or more products, said one or more nonpolar reaction solvents and said at least one nonpolar extraction solvent, and (2) recovering said nonpo
    Type: Grant
    Filed: March 15, 2000
    Date of Patent: September 25, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Jeffrey Scott Kanel, John Nicholas Argyropoulos, Ailene Gardner Phillips, Brian Michael Roesch, John Robert Briggs, Max Min Lee, John Michael Maher, David Robert Bryant
  • Patent number: 6187963
    Abstract: Processes are disclosed for the conversion of propylene to an acrolein derivative by converting propylene to acrolein and converting acrolein to the acrolein derivative. The processes utilize oxygen and recycle propane to the acrolein reactor. Process feeds can comprise, propane, propylene or mixtures thereof. The presence of propane in the propylene-to-acrolein reaction can enhance the efficiency of the processes.
    Type: Grant
    Filed: October 9, 1998
    Date of Patent: February 13, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: William George Etzkorn, Richard A. Galley, Thomas E. Snead, Jonathan Lester Brockwell, Mark Anderson Young, John Michael Maher, Barbara Knight Warren
  • Patent number: 6184376
    Abstract: Methods and novel intermediates of the formula: wherein R6 and R7 are lower alkyl or benzyl or R6 and R7 taken together are —CH2CH2—, —CH2CH2CH2— or —CH2CH2CH2CH2CH2—, R8 is C1-C21 alkyl or a C2-C21 monounsaturated alkenyl, which may optionally be substituted with substitution substituents independently selected from the group consisting of hydroxy, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkanoyl, amino, halo, cyano, azido, oxo, mercapto and nitro, and R9 is an alcohol protecting group. The intermediates are useful for the preparation of acyclic nucleoside derivatives of the formula: where one of R1 and R2 is an amino acid acyl group and the other of R1 and R2 is a —C(O)C3-C21 saturated or monounsaturated, optionally substituted alkyl and R3 is OH or H; or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: August 6, 1998
    Date of Patent: February 6, 2001
    Assignee: Mediver AB
    Inventors: M. Robert Leanna, Steven M. Hannick, Michael Rasmussen, Jien-Heh J. Tien, Lakshmi Bhagavatula, Pulla Reddy Singam, Bradley D. Gates, Lawrence Kolaczkowski, Ramesh R. Patel, Greg Wayne, Greg Lannoye, Weijiang Zhang, Zhenping Tian, Kirill A. Lukin, Bikshandarkoil A. Narayanan, David A. Riley, Howard Morton, Sou-Jen Chang, Cynthia B. Curty, Daniel Plata, John Bellettini, Bhadra Shelat, Tiffany Spitz, Cheng-Xi Yang
  • Patent number: 6090974
    Abstract: This invention includes an alkyl 3-oxoalkanoate, and processes for its preparation and use for the synthesis of fatty hydroxylated amino acids, fatty amino alcohols and ceramides.
    Type: Grant
    Filed: October 15, 1996
    Date of Patent: July 18, 2000
    Assignee: L'Oreal SA
    Inventors: Michel Philippe, Bernadette Luppi, Didier Semeria, Claude Mahieu
  • Patent number: 6037489
    Abstract: A method for purifying glyoxylates includes (1) a coarse distillation process in which a crude glyoxylate in which water coexists is, in a film form, continuously subjected to coarse distillation, and (2) an azeotropic dehydration process in which the crude glyoxylate purified through the coarse distillation process is subjected to azeotropic dehydration in the presence of an azeotropic agent such as propyl acetate. By this method, high-purity glyoxylates can be efficiently and easily obtained at lower costs.
    Type: Grant
    Filed: April 10, 1998
    Date of Patent: March 14, 2000
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Hideyuki Baba, Satoru Miura, Masanori Nonoguchi, Noboru Saito
  • Patent number: 6030505
    Abstract: 5-Formylvaleric esters are prepared in a yield of not less than 90% by distillation of a formylvaleric ester mixture of 5-formylvaleric ester and either 3- or 4-formylvaleric ester or a mixture of 3- and 4-formylvaleric esters, where the ester radicals of the respective formylvaleric esters are identical, wherein the 3- or 4-formylvaleric ester or a mixture thereof is separated from the 5-formylvaleric ester in a distillation column at a pressure in the range from 2 to 100 mbar and a temperature of not above 150.degree. C. (measured as the temperature at the bottom of the column) and the esters used are the corresponding methyl or ethyl esters, where the purity of the 5-formylvaleric ester is not less than 98% and, as impurity, 4-formylvaleric ester is present in an amount of not more than 100 ppm.
    Type: Grant
    Filed: January 27, 1998
    Date of Patent: February 29, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Gunther Achhammer, Michael Roper
  • Patent number: 5952530
    Abstract: This invention relates to a process for separating one or more products from a reaction product fluid comprising a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, a nonpolar solvent and said one or more products, wherein said process comprises (1) mixing said reaction product fluid with a polar solvent to obtain by phase separation a non-polar phase comprising said metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand and said nonpolar solvent and a polar phase comprising said one or more products and polar solvent, and (2) recovering said polar phase from said nonpolar phase; wherein said organophosphorus ligand has a partition coefficient between the nonpolar solvent and the polar solvent of greater than about 5, and said one or more products have a partition coefficient between the polar solvent and the nonpolar solvent of greater than about 0.5.
    Type: Grant
    Filed: February 2, 1998
    Date of Patent: September 14, 1999
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John N. Argyropoulos, David Robert Bryant, Donald Lee Morrison, Kenneth Elwood Stockman
  • Patent number: 5932772
    Abstract: This invention relates to a process for separating one or more products from a reaction product fluid comprising a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, a polar solvent and said one or more products, wherein said process comprises (1) mixing said reaction product fluid with a nonpolar solvent to obtain by phase separation a polar phase comprising said metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand and said polar solvent and a nonpolar phase comprising said one or more products and nonpolar solvent, and (2) recovering said nonpolar phase from said polar phase; wherein said organophosphorus ligand has a partition coefficient between the polar solvent and the nonpolar solvent of greater than about 10, and said one or more products have a partition coefficient between the nonpolar solvent and the polar solvent of greater than about 0.5.
    Type: Grant
    Filed: February 2, 1998
    Date of Patent: August 3, 1999
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John N. Argyropoulos, David Robert Bryant, Donald Lee Morrison, Kenneth Elwood Stockman, Anthony George Abatjoglou
  • 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: 5767277
    Abstract: An optically active .beta.-aminoalkoxyborane complex of the formula (I): ##STR1## wherein R.sup.1 is C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.7 -C.sub.11 aralkyl or C.sub.6 -C.sub.10 aryl, R.sup.2 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.7 cycloalkyl or C.sub.7 -C.sub.11 aralkyl, or R.sup.1 and R.sup.2 together form (CH.sub.2).sub.n wherein n is 3 or 4, and Ar is naphthyl, anthryl or phenanthryl, which may be substituted by from 1 to 3 substituents selected from the group consisting of halogen, nitro, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.7 -C.sub.11 aralkyl, C.sub.6 -C.sub.10 aryl, C.sub.1 -C.sub.6 alkoxy and styrene polymer substituents.
    Type: Grant
    Filed: January 7, 1997
    Date of Patent: June 16, 1998
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Hiroshi Kashihara, Mikio Suzuki, Yoshio Ohara
  • Patent number: 5750769
    Abstract: The invention provides novel compounds of formula:CF.sub.3 --CXCl--CH(OH)CH.sub.2 --C(CH.sub.3).sub.2 --CH.sub.2 --CO.sub.2 R(I)where X represents chloro or bromo and R represents hydrogen or alkyl of up to 4 carbon atoms, processes for preparing them and their use as intermediates in the preparation of insecticidal cyclopropane derivatives. Also provided are novel compounds of formula:BrCH.sub.2 --CH.sub.2 --C(CH.sub.3).sub.2 --CH.sub.2 --CO.sub.2 R(IV)wherein R represents alkyl of up to 4 carbon atoms, useful as intermediates in the preparation of the compounds of formula I.
    Type: Grant
    Filed: November 8, 1995
    Date of Patent: May 12, 1998
    Assignee: Zeneca Limited
    Inventor: Martin Charles Bowden
  • Patent number: 5750768
    Abstract: A method of manufacturing .alpha.-oxocarboxylate includes the steps of: (i) carrying out a vapor phase oxidation of 1,2-diol of formula (1) in a primary reaction vessel, (ii) introducing a resulting gaseous .alpha.-oxoaldehyde and/or .alpha.-hydroxyaldehyde in a secondary reaction vessel together with alcohol or olefin which is converted into a gas form in a vaporizing chamber, and (iii) carrying out an oxidative esterification of the gaseous .alpha.-oxoaldehyde and/or .alpha.-hydroxyaldehyde molecular oxygen in a presence of inorganic oxide containing phosphorus as a catalyst in the secondary reaction vessel, ##STR1## (R is a hydrogen atom or an organic residue). The described method permits .alpha.-oxocarboxylate to be manufactured economically and effectively in practically one step using inexpensive 1,2-diol such as ethylene glycol or propylene glycol.
    Type: Grant
    Filed: August 6, 1996
    Date of Patent: May 12, 1998
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Yoshitaka Arita, Akihiko Ohta, Ren Hasebe, Noboru Saito
  • Patent number: 5719312
    Abstract: The invention relates to a process for the preparation of 5-formylvaleric acid or the corresponding 5-formylvalerate by hydroformylation of 3-pentenoic acid or 3-pentenoate ester with carbon monoxide and hydrogen in the presence of a catalyst comprising of rhodium and a phosphite ligand, wherein the phosphite ligand is represented by the following general formula ##STR1## where R.sup.1 and R.sup.2 are the same or different aromatic organic groups and where A is an n-valent group or atom and where n is an integer chosen upwards of 2 and where the respective ?--O--P(OR.sup.1)(OR.sup.2)! group may be the same group or different groups and where the phosphite forms a chelate-type complex with rhodium.
    Type: Grant
    Filed: June 27, 1996
    Date of Patent: February 17, 1998
    Assignee: DSM N.V.
    Inventors: Carolina B. Hansen, Johannes G. de Vries
  • Patent number: 5663348
    Abstract: An optically active .beta.-aminoalkoxyborane complex of the formula (I): ##STR1## wherein R.sup.1 is C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.7 -C.sub.11 aralkyl or C.sub.6 -C.sub.10 aryl, R.sup.2 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.7 cycloalkyl or C.sub.7 -C.sub.11 aralkyl, or R.sup.1 and R.sup.2 together form (CH.sub.2).sub.n wherein n is 3 or 4, and Ar is naphthyl, anthryl or phenanthryl, which may be substituted by from 1 to 3 substituents selected from the group consisting of halogen, nitro, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.7 -C.sub.11 aralkyl, C.sub.6 -C.sub.10 aryl, C.sub.1 -C.sub.6 alkoxy and styrene polymer substituents.
    Type: Grant
    Filed: July 19, 1995
    Date of Patent: September 2, 1997
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Hiroshi Kashihara, Mikio Suzuki, Yoshio Ohara
  • Patent number: 5648387
    Abstract: Dialkyl ethers lower Lp(a) and triglycerides, and elevate HDL-cholesterol, and are thereby useful for treating vascular diseases and noninsulin-dependent diabetes mellitus.
    Type: Grant
    Filed: March 24, 1995
    Date of Patent: July 15, 1997
    Assignee: Warner-Lambert Company
    Inventors: Charles Larry Bisgaier, Paul Leroy Creger, Alan Robert Saltiel, Sherrie Rae Tafuri
  • Patent number: 5527950
    Abstract: The invention relates to a process for the preparation of a 5-formylvalerate ester by hydroformylating a mixture of pentenoate esters in the presence of a catalyst system which catalyst system comprises a metal from group 8-10 of the Periodic Table of Elements and a mono- or multidentate organic phosphorous ligand, wherein the mixture of pentenoate esters contains less than 500 ppm hydroperoxide compounds.
    Type: Grant
    Filed: December 28, 1994
    Date of Patent: June 18, 1996
    Assignees: DSM N.V., E.I. Du Pont de Nemours & Co.
    Inventors: Carolina B. Hansen, Antonius J. J. M. Teunissen
  • Patent number: 5434281
    Abstract: Process for the stereospecific synthesis of leukotriene B.sub.4 (LTB.sub.4) of 6Z, 8E, 10E configuration of formula ##STR1## in which a dibenzoate triether is prepared which is subjected to a reductive elimination according to the diagram ##STR2## so as to obtain a triether which is converted in order to obtain the leukotriene B.sub.4.
    Type: Grant
    Filed: May 31, 1994
    Date of Patent: July 18, 1995
    Assignee: L'Oreal
    Inventors: Guy Solladie, Guy Stone, Antonio Urbano-Pujol, Jean Maignan
  • Patent number: 5360938
    Abstract: This invention relates to asymmetric syntheses in which a prochiral or chiral compound is contacted in the presence of an optically active metal-ligand complex catalyst to produce an optically active product.
    Type: Grant
    Filed: July 16, 1992
    Date of Patent: November 1, 1994
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: James E. Babin, Gregory T. Whiteker
  • Patent number: 5264616
    Abstract: .omega.-Formyl-C.sub.4 -C.sub.20 -alkanecarboxylic esters are prepared by reacting C.sub.4 -C.sub.20 -alkenecarboxylic esters with carbon monoxide and hydrogen at from 30.degree. to 150.degree. C. and under from 0.01 to 30 bar in the presence of rhodium carbonyl complexes which are modified with polyphosphites.
    Type: Grant
    Filed: February 17, 1993
    Date of Patent: November 23, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Roeper, Peter M. Lorz, Dieter Koeffer
  • Patent number: 5256813
    Abstract: A 3-substituted 2-hydroxy-3-formylpropionic ester of the formula I ##STR1## where R.sup.1 is lower alkyl, and R.sup.2 is straight-chain or branched alkyl of 1 to 10 carbon atoms, is obtained by adding an alkanal of the fomrula II ##STR2## and an alkyl glyoxylate of the formula III ##STR3## simultaneously to a catalyst system composed of a salt or a mixture of a secondary amine and a carboxylic acid in such a way that the temperature does not exceed 90.degree. C., preferably 80.degree. C., or else adding one of the reactants of the formula II or III to a mixture of the catalyst system described above and the other reactant in such a way that the temperature does not exceed 90.degree. C. The 2-hydroxy-3-formylpropionic eater of the formula I can be converted by treatment with dehydrating agents, especially acetic anhydride, into good yields of the corresponding 3-substituted 3-formylacrylic ester.
    Type: Grant
    Filed: May 15, 1992
    Date of Patent: October 26, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Juergen Frank
  • Patent number: 5239086
    Abstract: Disclosed is a substantially optically pure hapten, useful in an immunoassay for dextropropoxyphene and/or nordextropropoxyphene. The hapten corresponds to a specified structural formula (IX).Also disclosed is an immunogen derived from the hapten as well as an antibody raised in response to an immunogen derived from the hapten.Also disclosed is a fluorescent tracer derived from a substantially optically pure compound corresponding to the hapten, the tracer being useful in an immunoassay for dextropropoxyphene and/or nordextropropoxyphene.Also disclosed is an improved immunoassay for determining dextropropoxyphene and/or nordextropropoxyphene in a biological sample involving a step of contacting the sample with antibodies raised in response to the immunogen.
    Type: Grant
    Filed: July 29, 1991
    Date of Patent: August 24, 1993
    Assignee: Abbott Laboratories
    Inventors: Robert E. Dubler, Jonathan Grote, Donna R. Kuhn
  • Patent number: 5239108
    Abstract: A process for producing an aliphatic or alicyclic aldehyde is disclosed, which process comprises the step of hydrogenating an aliphatic or alicyclic carboxylic acid or a derivative thereof with molecular hydrogen in the presence of a catalyst, wherein the catalyst is a zirconium oxide catalyst which contains chromium as an essential component, has a weakly basic site amount of more than 0.03 mmol/g as determined by a temperature programmed desorption method using carbon dioxide as an adsorbate in which the amount of carbon dioxide desorbed in the temperature range of from 100.degree. to 250.degree. C. is measured, and has pores having a radius of from 20 to 500 .ANG. in an amount of not less than 0.1 cc/g and pores having a radius of from 1,000 to 50,000 .ANG. in an amount of not less than 0.05 cc/g as measured with a mercury porosimeter. Aldehydes can be obtained directly from aliphatic or alicyclic carboxylic acids or derivatives thereof in high yield.
    Type: Grant
    Filed: October 20, 1992
    Date of Patent: August 24, 1993
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Toshiharu Yokoyama, Naoko Matsuyama, Takao Maki