Aldehyde Group In Acid Moiety Patents (Class 560/177)
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Patent number: 10745369Abstract: 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: GrantFiled: November 26, 2019Date of Patent: August 18, 2020Assignees: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC, ARCHER DANIELS MIDLAND COMPANYInventors: Stephen J. Howard, Kristina A. Kreutzer, Bhuma Rajagopalan, Eric R. Sacia, Alexandra Sanborn, Brennan Smith
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Patent number: 10526356Abstract: 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: GrantFiled: November 7, 2017Date of Patent: January 7, 2020Assignee: EVONIK DEGUSSA GMBHInventors: Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Dieter Hess
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Publication number: 20150031887Abstract: 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: ApplicationFiled: February 22, 2013Publication date: January 29, 2015Inventors: Yoshiharu Iwabuchi, Masatoshi Shibuya, Ryusuke Doi
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Publication number: 20140228579Abstract: 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: ApplicationFiled: September 11, 2013Publication date: August 14, 2014Applicant: Brock UnviersityInventors: Georgii Nikonov, Dmitry Gutsulyak, Sun Hwa Lee
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Patent number: 8801939Abstract: 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: GrantFiled: April 19, 2013Date of Patent: August 12, 2014Assignees: University of Kansas, Archer Daniels Midland CompanyInventors: Bala Subramaniam, Daryle Busch, Andrew M. Danby, Thomas P Binder
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Patent number: 8729294Abstract: 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: GrantFiled: May 30, 2011Date of Patent: May 20, 2014Assignee: Sumitomo Chemical Company, LimitedInventor: Yujiro Hayashi
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Patent number: 8586632Abstract: 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: GrantFiled: April 25, 2007Date of Patent: November 19, 2013Assignees: Monell Chemical Senses Center, The Trustees of The University of PennsylvaniaInventors: Catherine Peyrot Des Gachons, Jeffrey B. Sperry, Bruce Bryant, Paul A. S. Breslin, Amos B. Smith, III, Gary K. Beauchamp
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Publication number: 20130137880Abstract: 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: ApplicationFiled: May 30, 2011Publication date: May 30, 2013Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventor: Yujiro Hayashi
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Patent number: 8425784Abstract: 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: GrantFiled: November 4, 2008Date of Patent: April 23, 2013Assignees: University of Kansas, Archer Daniels Midland CompanyInventors: Bala Subramaniam, Daryle Busch, Andrew M. Danby, Thomas P. Binder
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Publication number: 20130005807Abstract: 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: ApplicationFiled: June 29, 2012Publication date: January 3, 2013Applicant: TAKASAGO INTERNATIONAL CORPORATIONInventors: Kenya ISHIDA, Tomoko YAMAMOTO, Miho SUZUKI
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Publication number: 20120198590Abstract: 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: ApplicationFiled: January 27, 2012Publication date: August 2, 2012Applicant: J.D. IRVING, LIMITEDInventors: John David Miller, Greg William Adams, Mark Sumarah
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Publication number: 20110124904Abstract: 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: ApplicationFiled: November 25, 2009Publication date: May 26, 2011Inventor: Daniel F. White
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Publication number: 20110020424Abstract: 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: ApplicationFiled: April 25, 2007Publication date: January 27, 2011Inventors: Catherine Peyrot Des Gachons, Jeffrey B. Sperry, Bruce Bryant, Paul A.S. Breslin, Amos B. Smith, III, Gary K. Beauchamp
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Publication number: 20110004002Abstract: 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 VIIType: ApplicationFiled: February 27, 2009Publication date: January 6, 2011Applicant: BASF SEInventors: Volker Maywald, Sebastian Peer Smidt, Bernd Wolf, Christopher Koradin, Thomas Zierke, Michael Rack, Michael Keil
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Publication number: 20090259065Abstract: 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: ApplicationFiled: April 10, 2009Publication date: October 15, 2009Inventors: Timothy W. Abraham, Hiroki Kaido, Choon Woo Lee, Richard L. Pederson, Yann Schrodi, Michael John Tupy, Alexandre A. Pletnev
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Publication number: 20090118498Abstract: 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: ApplicationFiled: November 4, 2008Publication date: May 7, 2009Inventors: Bala Subramaniam, Daryle Busch, Andrew M. Danby, Thomas P. Binder
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Patent number: 7432392Abstract: 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: GrantFiled: February 27, 2006Date of Patent: October 7, 2008Assignee: Japan Tobacco Inc.Inventors: Atsushi Hagiwara, Taku Ikenogami, Yasuko Mera, Yukako Sumida, Akio Iida, Toshio Taniguchi, Mitsuru Takahashi
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Patent number: 6541660Abstract: 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: GrantFiled: March 27, 2002Date of Patent: April 1, 2003Assignee: BASF AktiengesellschaftInventors: Udo Rheude, Maximilian Vicari, Werner Aquila, Günter Wegner, Jörg Niekerken
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Patent number: 6521752Abstract: 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: GrantFiled: August 16, 2001Date of Patent: February 18, 2003Assignees: DSM N.V., E.I. Dupont de Nemours and Co.Inventors: Onko J. Gelling, Peter C. Borman
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Patent number: 6489505Abstract: 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: GrantFiled: January 26, 2001Date of Patent: December 3, 2002Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Hagiya, Ichiro Komoto, Akio Kurihara
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Patent number: 6407282Abstract: 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: GrantFiled: October 30, 2000Date of Patent: June 18, 2002Assignee: Nippon Mektron, LimitedInventors: Hiroaki Murata, Sunao Ikeda, Satoru Saito
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Patent number: 6313343Abstract: 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: GrantFiled: January 7, 2000Date of Patent: November 6, 2001Assignee: Nippon Shokubai Co., Ltd.Inventors: Yoshitaka Arita, Akihiko Ohta, Noboru Saito, Kimio Ariyoshi
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Patent number: 6310260Abstract: 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: GrantFiled: March 15, 2000Date of Patent: October 30, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: 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
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Patent number: 6307110Abstract: 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: GrantFiled: March 15, 2000Date of Patent: October 23, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: 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
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Patent number: 6307109Abstract: 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: GrantFiled: March 15, 2000Date of Patent: October 23, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Jeffrey Scott Kanel, David Robert Bryant, Brian Michael Roesch, Ailene Gardner Phillips
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Patent number: 6307108Abstract: 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: GrantFiled: March 15, 2000Date of Patent: October 23, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: John Nicholas Argyropoulos, Jeffrey Scott Kanel, Michael Leo Tulchinsky, David James Miller, Donald Lee Morrison, Paul Foley, David Robert Bryant
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Patent number: 6303829Abstract: 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 polarType: GrantFiled: March 15, 2000Date of Patent: October 16, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Jeffrey Scott Kanel, John Nicholas Argyropoulos, Ailene Gardner Phillips, Brian Michael Roesch, John Robert Briggs, Max Min Lee, John Michael Maher, David Robert Bryant
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Patent number: 6303830Abstract: 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: GrantFiled: March 15, 2000Date of Patent: October 16, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: John Nicholas Argyropoulos, Jeffrey Scott Kanel, Michael Leo Tulchinsky, David James Miller, Donald Lee Morrison, Paul Foley, David Robert Bryant
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Patent number: 6294700Abstract: 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 nonpoType: GrantFiled: March 15, 2000Date of Patent: September 25, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Jeffrey Scott Kanel, John Nicholas Argyropoulos, Ailene Gardner Phillips, Brian Michael Roesch, John Robert Briggs, Max Min Lee, John Michael Maher, David Robert Bryant
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Patent number: 6187963Abstract: 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: GrantFiled: October 9, 1998Date of Patent: February 13, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: William George Etzkorn, Richard A. Galley, Thomas E. Snead, Jonathan Lester Brockwell, Mark Anderson Young, John Michael Maher, Barbara Knight Warren
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Patent number: 6184376Abstract: 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: GrantFiled: August 6, 1998Date of Patent: February 6, 2001Assignee: Mediver ABInventors: 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
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Patent number: 6090974Abstract: 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: GrantFiled: October 15, 1996Date of Patent: July 18, 2000Assignee: L'Oreal SAInventors: Michel Philippe, Bernadette Luppi, Didier Semeria, Claude Mahieu
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Patent number: 6037489Abstract: 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: GrantFiled: April 10, 1998Date of Patent: March 14, 2000Assignee: Nippon Shokubai Co., Ltd.Inventors: Hideyuki Baba, Satoru Miura, Masanori Nonoguchi, Noboru Saito
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Patent number: 6030505Abstract: 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: GrantFiled: January 27, 1998Date of Patent: February 29, 2000Assignee: BASF AktiengesellschaftInventors: Gunther Achhammer, Michael Roper
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Patent number: 5952530Abstract: 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: GrantFiled: February 2, 1998Date of Patent: September 14, 1999Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: John N. Argyropoulos, David Robert Bryant, Donald Lee Morrison, Kenneth Elwood Stockman
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Patent number: 5932761Abstract: 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: GrantFiled: March 23, 1998Date of Patent: August 3, 1999Assignee: Kuraray Co., Ltd.Inventors: Toshihiro Omatsu, Masahiko Kitayama, Takashi Onishi
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Patent number: 5932772Abstract: 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: GrantFiled: February 2, 1998Date of Patent: August 3, 1999Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: John N. Argyropoulos, David Robert Bryant, Donald Lee Morrison, Kenneth Elwood Stockman, Anthony George Abatjoglou
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Patent number: 5767277Abstract: 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: GrantFiled: January 7, 1997Date of Patent: June 16, 1998Assignee: Nissan Chemical Industries Ltd.Inventors: Hiroshi Kashihara, Mikio Suzuki, Yoshio Ohara
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Patent number: 5750768Abstract: 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: GrantFiled: August 6, 1996Date of Patent: May 12, 1998Assignee: Nippon Shokubai Co., Ltd.Inventors: Yoshitaka Arita, Akihiko Ohta, Ren Hasebe, Noboru Saito
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Patent number: 5750769Abstract: 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: GrantFiled: November 8, 1995Date of Patent: May 12, 1998Assignee: Zeneca LimitedInventor: Martin Charles Bowden
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Patent number: 5719312Abstract: 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: GrantFiled: June 27, 1996Date of Patent: February 17, 1998Assignee: DSM N.V.Inventors: Carolina B. Hansen, Johannes G. de Vries
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Patent number: 5663348Abstract: 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: GrantFiled: July 19, 1995Date of Patent: September 2, 1997Assignee: Nissan Chemical Industries Ltd.Inventors: Hiroshi Kashihara, Mikio Suzuki, Yoshio Ohara
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Patent number: 5648387Abstract: 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: GrantFiled: March 24, 1995Date of Patent: July 15, 1997Assignee: Warner-Lambert CompanyInventors: Charles Larry Bisgaier, Paul Leroy Creger, Alan Robert Saltiel, Sherrie Rae Tafuri
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Patent number: 5527950Abstract: 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: GrantFiled: December 28, 1994Date of Patent: June 18, 1996Assignees: DSM N.V., E.I. Du Pont de Nemours & Co.Inventors: Carolina B. Hansen, Antonius J. J. M. Teunissen
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Patent number: 5434281Abstract: 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: GrantFiled: May 31, 1994Date of Patent: July 18, 1995Assignee: L'OrealInventors: Guy Solladie, Guy Stone, Antonio Urbano-Pujol, Jean Maignan
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Patent number: 5360938Abstract: 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: GrantFiled: July 16, 1992Date of Patent: November 1, 1994Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: James E. Babin, Gregory T. Whiteker
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Patent number: 5264616Abstract: .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: GrantFiled: February 17, 1993Date of Patent: November 23, 1993Assignee: BASF AktiengesellschaftInventors: Michael Roeper, Peter M. Lorz, Dieter Koeffer
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Patent number: 5256813Abstract: 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: GrantFiled: May 15, 1992Date of Patent: October 26, 1993Assignee: BASF AktiengesellschaftInventors: Franz Merger, Juergen Frank
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Patent number: 5239108Abstract: 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: GrantFiled: October 20, 1992Date of Patent: August 24, 1993Assignee: Mitsubishi Kasei CorporationInventors: Toshiharu Yokoyama, Naoko Matsuyama, Takao Maki
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Patent number: 5239086Abstract: 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: GrantFiled: July 29, 1991Date of Patent: August 24, 1993Assignee: Abbott LaboratoriesInventors: Robert E. Dubler, Jonathan Grote, Donna R. Kuhn