Decarboxylation Of Polycarboxylic Acid Or Salt Patents (Class 562/479)
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Patent number: 8951750Abstract: The present invention relates to a method for the enzymatic decarboxylation of malonic acid (propanedioic acid) derivatives catalyzed by enzymes structurally and/or functionally related to arylmalonate decarboxylase (AMDase) as isolated from microorganisms of the genus Bordetella. The present invention also relates to novel enzymes with a decarboxylase activity, useful for performing the claimed method, mutants thereof, corresponding coding sequences and expression systems, methods of preparing said novel enzymes, and screening methods for obtaining further suitable enzymes also having said decarboxylase activity.Type: GrantFiled: November 28, 2008Date of Patent: February 10, 2015Assignee: BASF SEInventors: Bernhard Hauer, Nina Schneider, Krzysztof Okrasa, Jason Micklefield, David Leys, Colin Levy
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Patent number: 8304575Abstract: The present invention relates to a process for producing an ether carboxylate which includes the steps of (1) reacting an aliphatic monohydric alcohol with an alkylene oxide in the presence of an alkali catalyst; (2) neutralizing a reaction solution obtained in the step (1) with an acid such as hydroxycarboxylic acids to obtain an ether alcohol; and (3-1) reacting the obtained ether alcohol with a monohalogenofatty acid or a salt thereof and an alkali metal hydroxide, or (3-2) subjecting the obtained ether alcohol to catalytic oxidation reaction in the presence of a catalyst. The obtained ether carboxylate has a less odor and a high quality and is therefore suitably used in the applications such as cosmetics and toiletries.Type: GrantFiled: April 3, 2008Date of Patent: November 6, 2012Assignee: Kao CorporationInventors: Akira Matsunaga, Kaoru Ohmae
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Patent number: 6784134Abstract: A catalyst suited for catalytic vapor-phase oxidation of isobutylene, t-butanol or propylene to produce respectively corresponding unsaturated aldehyde and unsaturated carboxylic acid is provided. Said catalyst consists of ring-formed shaped bodies composed of (i) a catalyst composition containing at least molybdenum and bismuth as the active ingredients and (ii) inorganic fibers. The catalyst excels in mechanical strength, can give the object products at high yield and shows little activity degradation with time.Type: GrantFiled: March 20, 2002Date of Patent: August 31, 2004Assignee: Nippon Shokubai Co., Ltd.Inventors: Hiroto Kasuga, Eiichi Shiraishi
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Publication number: 20040068141Abstract: The present invention addresses a process for the preparation of 2,4,5-trifluorophenylacetic acid using a Cu(I) salt as a catalyst.Type: ApplicationFiled: October 7, 2003Publication date: April 8, 2004Inventors: Joseph D. Armstrong, Spencer D. Dreher, Norihiro Ikemoto
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Patent number: 6191307Abstract: A process of producing benzoic acids from phthalimides is described. The ability to dramatically reduce the reaction time in comparison to currently practiced processes by the addition of readily available compounds is demonstrated.Type: GrantFiled: April 6, 1999Date of Patent: February 20, 2001Assignee: Albemarle CorporationInventors: Tse-Chong Wu, R. Carl Herndon, Jr.
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Patent number: 5922906Abstract: The present invention is directed to an improved process for preparing the phenylacetic acid side chain of the compound of the formula ##STR1## This compound exhibits utility as a Class III antiarrhythmic agent.Type: GrantFiled: August 3, 1998Date of Patent: July 13, 1999Assignee: Merck & Company, Inc.Inventors: Joseph E. Lynch, Yao-Jun Shi, Kenneth M. Wells
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Patent number: 5872283Abstract: Halogenated aromatic carboxylic acids are decarboxylated by heating them in the presence of water at temperatures of 80.degree. to 180.degree. C. and in the presence of water and other acids at temperatures above 80.degree. C.Type: GrantFiled: June 26, 1997Date of Patent: February 16, 1999Assignee: Bayer AktiengesellschaftInventors: Stefan Antons, Guido Steffan, Helmut Fiege
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Patent number: 5792887Abstract: A process for the monodecarboxylation of a halogenated aromatic dicarboxylic acid or derivative thereof in which the halogenated aromatic dicarboxylic acid or derivative thereof in a liquid medium is heated characterized in that the liquid medium is a polar aprotic liquid medium.Type: GrantFiled: November 4, 1996Date of Patent: August 11, 1998Assignee: Zeneca LimitedInventors: Stewart Reid Korn, Michael Scott Howarth, Gordon Jamieson
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Patent number: 5786494Abstract: Process for the synthesis of a-substituted acrylic acids and their application.Process for the synthesis of a-substituted acrylic acids of general formula (I) and their application to the synthesis of N- (mercaptoacyl) aminoacid derivatives of formula (II).Type: GrantFiled: March 1, 1996Date of Patent: July 28, 1998Assignee: Societe Civile BioprojetInventors: Pierre Duhamel, Lucette Duhamel, Denis Danvy, Thierry Monteil, Jeanne-Marie Lecomte, Jean-Charles Schwartz
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Patent number: 5739388Abstract: The present invention relates to a process for the preparation of compounds of the formula ##STR1## in which the radicals R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are COOH, H, F, Cl, Br, CF.sub.3, OH, an alkoxy or alkyl radical having in each case 1 to 4 carbon atoms or a radical --NR.sup.6 R.sup.7, in which R.sup.6 and R.sup.7 are identical or different and are H, an alkyl radical having 1 to 4 carbon atoms or a phenyl radical, by dissolving in water a compound of the formula ##STR2## in which the radicals R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and have the abovementioned meaning or, in departure therefrom, instead of H can be COOH, admixing the aqueous solution with a water-insoluble amine which is inert under the reaction conditions and carrying out the decarboxylation at a pH of 3 to 9 and a temperature of 70.degree. to 210.degree. C.Type: GrantFiled: May 2, 1996Date of Patent: April 14, 1998Assignee: Hoechst AktiengesellschaftInventors: Ralf Pfirmann, Hans Schubert
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Patent number: 5668186Abstract: The invention relates to a novel process for depolymerizing polyesters by subjecting the polyesters to catalysts and organic solvents which are substantially free of oxygen and water in order to produce macrocyclic polyester oligomers substantially free of hydroxybutyl terminated linear impurities.Type: GrantFiled: March 20, 1996Date of Patent: September 16, 1997Assignee: General Electric CompanyInventors: Daniel Joseph Brunelle, Ganesh Kailasam, Judith Ann Serth-Guzzo, Paul Russell Wilson
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Patent number: 5523476Abstract: A process for producing tetrafluorophthalic anhydride, which comprises chlorinating tetrachlorophthalic anhydride to obtain 3,3,4,5,6,7-hexachloro-1-[3H]-isobenzofuranone, then fluorinating it to obtain 3,4,5,6-tetrafluorophthaloyldifluoride and/or 3,3,4,5,6,7-hexafluoro-1-[3H]-isobenzofuranone, and further reacting the tetrafluorophthalolyldifluoride and/or the hexafluoro-1-[3H]-isobenzofuranone with an inorganic base or an organic acid to obtain tetrafluorophthalic anhydride.Type: GrantFiled: February 21, 1995Date of Patent: June 4, 1996Assignee: Asahi Glass Company Ltd.Inventors: Ryuji Seki, Koji Sugimoto, Seisaku Kumai
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Patent number: 5336806Abstract: Disclosed is a process for isolating and purifying 2,4,5-trifluorobenzoic acid from a solution in a decarboxylating solvent such as NMP. The solution is neutralized with a hydroxide. This results in the formation of a salt of the 2,4,5-trifluorobenzoic acid, which precipitates. The slurry is filtered to collect the precipitated salt and the precipitated salt is dissolved in water. The aqueous solution of the salt is then acidified which results in the reformation and precipitation of the 2,4,5-trifluorobenzoic acid.Type: GrantFiled: September 20, 1993Date of Patent: August 9, 1994Assignee: Occidental Chemical CorporationInventor: Jian S. Qi
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Patent number: 5329054Abstract: Activated carboxylic acids and esters such as pentafluorobenzoic acid are rapidly decarboxylated in high yields by reacting the acid or ester with an alkanolamine reagent which catalyzes the reaction.Type: GrantFiled: July 19, 1993Date of Patent: July 12, 1994Assignee: Albemarle CorporationInventors: Kevin J. Theriot, Niomi L. Krzystowczyk, Yueh-Dong Chen, Edward A. Burt, Lawrence H. Shepherd, Jr.
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Patent number: 5275950Abstract: Intermediates and a process for their preparation are disclosed which are useful for the preparation of a renin inhibiting compound of the formula: ##STR1## wherein R is a nitrogen-containing heterocycle which is bonded via a nitrogen atom to the sulfonyl group, R.sub.6 is hydrogen, alkoxy, halogen or loweralkyl, R.sub.7 is loweralkyl having 2 to 7 carbon atoms, and R.sub.8 is loweralkyl, cycloalkyl, or aryl or a pharmaceutically acceptable acid addition salt thereof.Type: GrantFiled: February 10, 1993Date of Patent: January 4, 1994Assignee: Abbott LaboratoriesInventors: Daniel A. Dickman, Bruce W. Horrom, Chi-Nung W. Hsiao, M. Robert Leanna, Hormoz Mazdiyasni, Howard E. Morton, Thomas M. Zydowsky, William R. Baker, Stephen L. Condon
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Patent number: 5233085Abstract: 3,4,6-Trifluorophthalic acid may be decarboxylated in a controlled manner to form 2,4,5-trifluorobenzoic acid by heating the phthalic acid in a dipolar aprotic solvent in the absence of any catalyst.Type: GrantFiled: June 12, 1992Date of Patent: August 3, 1993Assignee: Occidental Chemical CorporationInventors: Neil J. O'Reilly, William S. Derwin, Henry C. Lin
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Patent number: 5144067Abstract: Disclosed is a process for the coproduction of (1) an alkyl iodide and (2) an .alpha.-iodocarboxylic acid, a mono-.alpha.-iodocarboxylic anhydride or a mixture thereof which comprises contacting a mixture of an iodine compound and a carboxylic anhydride with a peroxide at an elevated temperature.Type: GrantFiled: September 29, 1989Date of Patent: September 1, 1992Assignee: Eastman Kodak CompanyInventors: Joseph R. Zoeller, Michael R. Cushman, Regina M. Moncier, Brent A. Tennant
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Patent number: 5089661Abstract: A new process is described for the preparation of a 2-aryl-propionic acid, such as for instance 2-[4-(2-methyl-propyl)phenyl]propionic or 2-(6'-methoxy-2'-naphthyl)propionic acid, through hydrogenation of a complex salt which consists of the mono- and/or di-valent anion of the corresponding 2-hydroxy-2-aryl-propionic acid, a di- or tri-valent metal cation, such as for instance Al(+3), Fe(+3), Zn(+2), or Mg(+2), and optionally other anonic or neutral ligands.This new process is particularly advantageous in that the starting salt can be obtained directly via electrocarboxylation of the corresponding aryl methyl ketone, e.g. 4-(2-methyl-propyl)acetophenone or (6-methoxy-2-naphthyl) methyl ketone, with metal anodes which dissolve during the electrolysis.Type: GrantFiled: September 10, 1990Date of Patent: February 18, 1992Assignee: Enichem Synthesis S.p.A.Inventors: Federico Maspero, Oreste Piccolo, Ugo Romano, Salvatore Gambino
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Patent number: 5003103Abstract: 2-Chloro-4,5-difluorobenzoic acid may be prepared by decarboxylating 4,5-difluorophthalic anhydride or 4,5-difluorophthalic acid by heating in N-methyl-2-pyrrolidone or dimethyl acetamide optionally using copper, copper oxide, copper salts, or halides or salts of Zn, Cd, Ag and Ni as a catalyst to form 3,4-difluorobenzoic acid, reacting said 3,4-difluorobenzoic acid with a mixture of nitric and sulfuric acids to form 2-nitro-4,5-difluorobenzoic acid, reacting said 2-nitro-4,5-difluorobenzoic acid with elemental chlorine at a temperature of between 185.degree. and 195.degree. C. to form 2-chloro-4,5-difluorobenzoic acid.Type: GrantFiled: June 4, 1990Date of Patent: March 26, 1991Assignee: Occidental Chemical CorporationInventors: Lawrence B. Fertel, Henry C. Lin
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Patent number: 4994606Abstract: 4,5-Difluoroanthranilic acid may be prepared by decarboxylating 4,5-difluorophthalic anhydride or 4,5-difluorophthalic acid by heating in dimethyl acetamide, N-methyl-2-pyrrolidone or quinoline, optionally by reaction with copper, copper oxide, copper salts, or halides and salts of Zn, Cd, Ag and Ni as a catalyst, whereby 3,4-difluorobenzoic acid is formed; nitrating said 3,4-difluorobenzoic acid in a mixture of nitric and sulfuric acids to form 2-nitro-4,5-difluorobenzoic acid, and reducing said 2-nitro-4,5-difluorobenzoic acid to form 4,5-difluoroanthranilic acid.Type: GrantFiled: June 4, 1990Date of Patent: February 19, 1991Assignee: Occidental Chemical CorporationInventors: Lawrence B. Fertel, Henry C. Lin
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Patent number: 4937377Abstract: 4,5-Difluorphthalic anhydride and 4,5-difluorophthalic acid may be decarboxylated in high yield to 3,4-difluorobenzoic acid by heating in N-methyl-2-pyrrolidone or dimethyl acetamide using copper, copper oxide, copper salts, or halides and salts of Zn, Cd, Ag and Ni as a catalyst.Type: GrantFiled: November 20, 1989Date of Patent: June 26, 1990Assignee: Occidental Chemical CorporationInventors: Lawrence B. Fertel, Neil J. O'Reilly
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Patent number: 4935541Abstract: It has been discovered that 3,4,6-trifluorophthalic anhydride may be decarboxylated by heating in a polar aprotic solvent to yield 2,4,5-trifluorobenzoic acid.Type: GrantFiled: November 20, 1989Date of Patent: June 19, 1990Assignee: Occidental Chemical CorporationInventors: Neil J. O'Reilly, William S. Derwin, Henry C. Lin
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Patent number: 4782180Abstract: An improved process for the preparation of 2,3,4,5-tetrafluorobenzoic acid is described which involves decarboxylation of tetrafluorophthalic acid in the presence of a base catalyst. Also described is an improved method for preparing tetrafluorophthalic acid and, in turn, a one-pot process for tetrafluorobenzoic acid using the combination of the two improvements.Type: GrantFiled: May 7, 1986Date of Patent: November 1, 1988Assignee: Warner-Lambert CompanyInventors: James N. Wemple, Timothy P. Puls, James Vande Vusse
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Patent number: 4782176Abstract: Phenoxycarboxylic acids of the formula ##STR1## wherein R, R.sub.1, R.sub.2, R.sub.3, R.sub.4 R.sub.5, Z and n are as hereinafter set forth, are as described. The compounds of formula I are antagonists of slow reacting substance of anaphylaxis (SRS-A), which renders them useful as agents for the treatment of allergic conditions.Type: GrantFiled: May 23, 1983Date of Patent: November 1, 1988Assignee: Hoffmann-La Roche Inc.Inventors: Matthew Carson, Ronald A. LeMahieu, William C. Nason
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Patent number: 4769492Abstract: A method for the production of 2,3,4,5-tetrafluorobenzoic acid, which comprises effecting said production by decarbonating 3,4,5,6-tetrafluorophthalic acid in an aqueous medium adjusted to a pH in the range of 0.7 to 2.2 at a temperature in the range of 100.degree. to 220.degree. C.Type: GrantFiled: March 7, 1986Date of Patent: September 6, 1988Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.Inventors: Osamu Kaieda, Isao Okitaka, Toshiaki Nakamura, Koichi Hirota
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Patent number: 4485244Abstract: A thermal process for the decarboxylation and dehydration of aromatic acid residue to convert such residue to grindable form and recover the solvent of reaction therefrom.Type: GrantFiled: November 3, 1982Date of Patent: November 27, 1984Assignee: The Standard Oil CompanyInventors: Joseph D. Fox, George E. Kuhlmann, John G. Hundley
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Patent number: 4345098Abstract: A process for producing an isomerized benzene carboxylic acid salt by treating a mixture of an aromatic material, water, and a water soluble reagent comprising a Group Ia or IIa metal with oxygen under conditions sufficient to convert at least a portion of the aromatic material to a benzene carboxylic acid salt of the metal; isomerizing the benzene carboxylic acid salt by heating without converting the benzene carboxylic acid salt to a benzene carboxylic acid salt of a different Group Ia or IIa metal prior to isomerizing; and recovering the benzene carboxylic acid salt. Another embodiment further comprises converting the isomerized benzene carboxylic acid salt to isomerized benzene carboxylic acid; regenerating the reagent; recovering the isomerized benzene carboxylic acid; and recycling the reagent thusly regenerated to supply a portion of the reagent required for producing the benzene carboxylic acid salt.Type: GrantFiled: February 29, 1980Date of Patent: August 17, 1982Assignee: Occidental Research CorporationInventor: Raymond A. Schep
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Patent number: 4324904Abstract: The invention concerns the novel compounds dialkyl 2-(3-fluoro-4-nitrophenyl)-2-methylmalonate IIIa and dialkyl 2-(3-fluoro-4-aminophenyl)-2-methylmalonate IVa useful as intermediates in an improved process for making 2-(2-fluoro-4-biphenylyl)propionic acid, known as flurbiprofen, having the formula ##STR1## and ester thereof. It has anti-inflammatory activity which is about 240 times that of aspirin and analgesic activity which is about 180 times that of aspirin in standard laboratory tests. However, despite this high activity, the toxicity (LD.sub.50) is only 1.2 to 2.4 times greater than that of aspirin in standard laboratory tests.Also within the invention is a novel method of making the above intermediates and analogs thereof useful to prepare corresponding biaryl compounds which have pharmaceutical uses.Type: GrantFiled: December 19, 1979Date of Patent: April 13, 1982Assignee: The Upjohn CompanyInventors: Thomas A. Hylton, Jerry A. Walker
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Patent number: 4304930Abstract: 2-(3-Phenoxy-phenyl)-propionic acid or its pharmaceutical treatments, are prepared by hydrolyzing and partially decarboxylating ##STR1## wherein R=C.sub.1 -C.sub.6 alkyl or amino, the latter compounds being themselves new and, where R=C.sub.1 -C.sub.6 alkyl, have antiinflammatory pharmaceutical properties.Type: GrantFiled: December 21, 1979Date of Patent: December 8, 1981Assignee: Chinoin Gyogyszer- es Vegyeszeti Termekek Gyara RtInventors: Endre Palosi, Gergely Heja, Dezso Korbonits, Pal Kiss, Csaba Gonczi, Judit Cser nee Kun, Ida Szvoboda nee Kanzel, Gabor Szabo, Tamas Kallay, Laszlo Ledniczky, Maria Szomor nee Wundele
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Patent number: 4275229Abstract: Monoethylenically unsaturated beta-carbonyl-containing carboxyl functional monomers and addition polymers containing them and other monoethylenically unsaturated monomers are disclosed, as are methods of coating substrates with the polymers to provide films of improved water resistance. The monomers are especially stable in the form of a salt with a volatile base, and the removal of the base when a polymer containing the monomer is cured causes decarboxylation, and the removal of the carboxyl groups improves the water resistance.Type: GrantFiled: February 12, 1979Date of Patent: June 23, 1981Assignee: DeSoto, Inc.Inventors: Stamatios G. Mylonakis, Anthony J. Tortorello
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Patent number: 4271316Abstract: A process for the continuous rearrangement of alkali metal salts of aromatic carboxylic acids is disclosed. The process is conducted under an atmosphere of carbon dioxide and in the presence of an organic diluent and results in high conversion rates and practically quantitative yields of the rearranged alkali metal salt of the aromatic carboxylic acid.Type: GrantFiled: July 20, 1979Date of Patent: June 2, 1981Assignee: Rhone-Poulenc IndustriesInventors: Jean-Claude Choulet, Jacques Nouvel
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Patent number: 4258227Abstract: Short, less than one second, residence time non-catalytic hydropyrolysis is conducted by rapid heating at more than 600.degree. C. per second of a solid mixture of aldehydo-, carboxy-, keto- and carboxy-, and aldehydo- and carboxy- substituted benzene and toluene and such solid also containing cobalt and/or manganese salts of organic acids and organic and/or inorganic bromides obtained from the manufacture of benzene di- and tricarboxylic acids up to a temperature of at least 700.degree. C. Such short residence hydropyrolysis produces attractive amounts of readily recoverable benzene and toluene as well as lower alkanes and alkenes and a solid carbonaceous char which can be burned to provide heat for the hydropyrolysis. The short residence hydropyrolysis is not subject to short activity and frequent periods of off-stream time as are the catalytic pyrolysis conducted at lower temperatures of from 300.degree. up to 500.degree. C.Type: GrantFiled: December 6, 1979Date of Patent: March 24, 1981Assignee: Standard Oil Company (Indiana)Inventors: John K. Allen, Agnes M. Palka, Edward A. Lambers
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Patent number: 4194053Abstract: A diester of .alpha.-acetyl-.alpha.'-methyl succinic acid is prepared in improved yield under substantially anhydrous process conditions which minimizes decomposition of that diester by reacting an acetoacetate ester with an .alpha.-halopropionate ester in a solvent containing a nonpolar, aprotic liquid at from about 50.degree. C. to reflux temperature in the presence of a phase transfer agent, a catalytic amount of iodide ion and solid form, substantially anhydrous alkali metal base or basic salt having a high surface area (a size of about 60 mesh or smaller). The resulting diesters can also be used under the stabilizing reaction mixture conditions of this invention as intermediates in processes for making ibuprofen by combining and reacting the .alpha.-acetyl-.alpha.'-methylsuccinate diester with vinyl isobutyl ketone, (or the corresponding Mannich base plus an alkylating agent) and an alkali metal base for a time sufficient to form a reaction mixture containing the .alpha.-methyl-.alpha.'-acetyl-.alpha.Type: GrantFiled: September 1, 1978Date of Patent: March 18, 1980Assignee: The Upjohn CompanyInventor: David R. White