Saturated Lower Fatty Acids Patents (Class 562/606)
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Patent number: 4447643Abstract: A thermally efficient process for recovering an oxygenated organic material, such as ethanol, present in dilute aqueous solution is disclosed which comprises contacting said dilute aqueous solution with at least one inert extractant which is liquid at ambient temperature and pressure, said extractant being selected from the group consisting of unsubstituted and substituted cyclic secondary amines and unsubstituted and substituted aromatic cyclic amines having a distribution coefficient of at least about 0.70 or a separation factor of at least about 1.0.Type: GrantFiled: August 11, 1982Date of Patent: May 8, 1984Assignee: National Distillers and Chemical CorporationInventor: Julian Feldman
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Patent number: 4444881Abstract: A process is provided for the recovery of organic acids from dilute aqueous solutions. The acid in the form of its calcium salt is treated with a tertiary amine carbonate and the resulting trialkylammonium salt of the acid is isolated and heated to give the acid plus a tertiary amine.Type: GrantFiled: June 27, 1983Date of Patent: April 24, 1984Assignee: CPC International Inc.Inventor: Branko Urbas
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Patent number: 4442124Abstract: The compound pivaloyloxymethyl 2-propyl-pentanoate of formula I: ##STR1## is described. The process for the preparation consists of reacting 2-propyl-pentanoic acid with chloromethyl pivalate and isolating the pivaloyloxymethyl 2-propyl-pentanoate from the reaction mixture. Pharmaceutical compositions with antiepileptic and anticonvulsant activity containing an effective amount of compound I are described.Type: GrantFiled: June 2, 1980Date of Patent: April 10, 1984Assignee: Texcontor-AnstaltInventor: Zemp J. Niklaus
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Patent number: 4442303Abstract: In one of its embodiments this invention provides a process for recovering C.sub.4 -C.sub.6 dicarboxylic acid components contained in a waste byproduct stream derived from a reaction system in which adipic acid is produced by nitric acid oxidation of cyclohexanone/cyclohexanol.An important aspect of the process is the esterification and extraction of the C.sub.4 -C.sub.6 dicarboxylic acids in the aqueous byproduct stream with a mixture of C.sub.1 -C.sub.3 alkanol and C.sub.6 -C.sub.20 alkanol, and the subsequent recovery of di(C.sub.6 -C.sub.20 alkyl) esters of succinic acid, glutaric acid and adipic acid.In a broader aspect this invention provides a process for recovery of water miscible organic acid components contained in an aqueous solution as C.sub.6 -C.sub.20 alkyl esters of the organic acids.Type: GrantFiled: December 9, 1980Date of Patent: April 10, 1984Assignee: El Paso Products CompanyInventor: Samuel S. Mims
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Patent number: 4433175Abstract: For the production of neohexanol with a purity above 99%, a chlorine content of less than 10 ppm, and a sulfur content of less than 5 ppm, 3,3-dimethylbutyric acid with a chlorine content below 650 ppm, preferably below 100 ppm, is first esterified, optionally after distillatory separation into a portion richer in chlorine with a chlorine content above 650 ppm, preferably above 100 ppm, and into a portion low in chlorine with a chlorine content below 650 ppm, preferably below 100, with an alcohol boiling above 117.degree. C., preferably an octyl alcohol. The resultant ester is separated by distillation into fractions richer in chlorine with chlorine contents above 10 ppm and into fractions low in chlorine with chlorine contents below 10 ppm. The ester of low chlorine contents below 10 ppm is hydrogenated to neohexanol over a barium-activated copper chromite catalyst under a pressure of 200-300 bar, at 120.degree.-22.degree. C., and with catalyst loads of 0.05-1.Type: GrantFiled: November 24, 1982Date of Patent: February 21, 1984Assignee: Chemische Werke Huels, A.G.Inventor: Manfred Kaufhold
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Patent number: 4431835Abstract: Alkyl carboxylates are hydrocarbonylated and/or carbonylated with carbon monoxide and hydrogen, in an aqueous medium, and in the presence of a catalytically effective amount of a catalyst system comprising (i) ruthenium, (ii) cobalt, (iii) at least one iodine-containing promoter, and (iv) chromium. The subject hydrocarbonylation/carbonylation is admirably well suited, e.g., for the preparation of acetaldehyde, ethanol, ethyl acetate and acetic acid, especially from a methyl carboxylate.Type: GrantFiled: July 6, 1981Date of Patent: February 14, 1984Assignee: Rhone-Poulenc IndustriesInventors: Jean Gauthier-Lafaye, Robert Perron
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Patent number: 4430506Abstract: Alkyl carboxylates are hydrocarbonylated and/or carbonylated with carbon monoxide and hydrogen, in an aqueous medium, and in the presence of a catalytically effective amount of a catalyst system comprising (i) ruthenium, (ii) cobalt, (iii) at least one iodine-containing promoter, and (iv) vanadium. The subject hydrocarbonylation/carbonylation is admirably well suited, e.g., for the preparation of acetaldehyde, ethanol, ethyl acetate and acetic acid, especially from a methyl carboxylate.Type: GrantFiled: July 6, 1981Date of Patent: February 7, 1984Assignee: Rhone-Poulenc IndustriesInventors: Jean Gauthier-Lafaye, Robert Perron
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Patent number: 4417073Abstract: A process for the preparation of substituted acetic acids and derivatives thereof, having the formula ##STR1## wherein X is --COOH, --COOY or --CN,Y is --CH.sub.3 or --C.sub.2 H.sub.5,R.sub.1 is a saturated, branched or unbranched aliphatic radical having from 1 to 6 carbon atoms, a phenyl radical, or a phenyl radical substituted by alkyl or alkoxy groups, andR.sub.2 is hydrogen or a saturated, branched or unbranched aliphatic radical having from 1 to 6 carbon atoms, a phenyl radical, or a phenyl radical substituted by alkyl or alkoxy groups,wherein R.sub.1 and R.sub.2 may be the same or different which process comprises converting the corresponding malonic or cyanoacetic ester of the formula ##STR2## wherein Z is --COOY or --CN, andY, R.sub.1 and R.sub.2 are identified as above at elevated temperature in the presence of a catalyst, e.g., a catalyst containing from about 50 to 75 weight percent SiO.sub.2 and from 15 to 19 weight percent Al.sub.2 O.sub.Type: GrantFiled: November 25, 1981Date of Patent: November 22, 1983Assignee: Dynamit Nobel A.G.Inventors: Otto Ackermann, Gerhard Daum
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Patent number: 4413118Abstract: Organic sulfur compounds containing a carbon-sulfur double bond are used to remove homogeneous catalyst group VIII metals from chemical process streams.Type: GrantFiled: March 2, 1981Date of Patent: November 1, 1983Assignee: Merck & Co., Inc.Inventors: F. Edward Roberts, Victor J. Grenda
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Patent number: 4401624Abstract: A method is disclosed for preparing and using buffered aqueous solutions of carboxylic acids and metal salts of carboxylic acids. Such solutions are useful as mold inhibitors in bread, cakes, and animal feeds. Buffered aqueous solutions of about 40 to 80 percent of compounds of carboxylic acids and carboxylic acid metal salts, such as sodium diacetate, sodium dipropionate, sodium dibutyrate or sodium dibenzoate have been found to have a reduced corrosive nature to metals and alloys used to contain, transport, and apply these solutions, thereby permitting the use of these metals and alloys in existing and new facilities.Type: GrantFiled: March 8, 1982Date of Patent: August 30, 1983Inventor: Charles B. Atwater
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Patent number: 4377708Abstract: Vinyl esters such as vinyl acetate are hydrocarboxylated with tertiary organo-phosphine stabilized palladium catalysts utilizing low water concentration; the ready hydrolysis of the .alpha.-acetoxypropionic acid affords a convenient route to lactic acid.Type: GrantFiled: October 14, 1977Date of Patent: March 22, 1983Assignee: Monsanto CompanyInventor: Donald E. Morris
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Patent number: 4377533Abstract: Process for introducing a substituent selected from branched- or straight-chain alkyl radicals having from 1 to 12 carbon atoms, aralkyl or cycloalkyl radicals in which the alkyl moiety has from 1 to 4 carbon atoms, into a carbon chain bearing a stable functional group the said carbon chain having at least one proton in .alpha.-position in relation to this functional group, process whereby, in a first step, this carbon chain is reacted with a complex base comprising a mixture of alkali metal amide and alkali metal alcoholate suspended in an anhydrous organic solvent to provide temporarily a carbanion, then in a second step this carbanion is reacted in an anhydrous organic solvent with an alkyl, aralkyl or cycloalkyl halide corresponding to the substituent to be introduced.Type: GrantFiled: April 3, 1981Date of Patent: March 22, 1983Assignee: SanofiInventors: Michel Bouisset, Michel Chignac, Claude Grain, Charles Pigerol
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Patent number: 4358609Abstract: A process for the recovery of carboxylic acids from mixtures containing glycol esters derived from these acids. The process comprises reacting these mixtures at boiling with water to form carboxylic acid and entraining the carboxylic acid formed by means of the water by azeotropic distillation, so as to separate off a mixture of carboxylic acid and water. This mixture is subjected to extractive distillation by means of an organic solvent which is insoluble in water and in which water is insoluble. A mixture of water and organic solvent is thereby separated from a solution of carboxylic acid in the organic solvent.Type: GrantFiled: October 1, 1980Date of Patent: November 9, 1982Assignee: Propylox (Societe Anonyme)Inventor: Nicolas Hardy
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Patent number: 4353835Abstract: A process for hydrogenating unsaturated carboxylic acids and esters of unsaturated carboxylic acids such as fatty acids which comprises reacting the unsaturated composition with hydrogen in contact with a catalyst prepared from a layered complex nickel silicate which has been prepared in a multi-stage procedure comprising reduction in a hydrogen atmosphere, oxidation in an atmosphere containing molecular oxygen and then again reduction in a hydrogen atmosphere.Type: GrantFiled: April 2, 1981Date of Patent: October 12, 1982Assignee: Gulf Research & Development CompanyInventor: Harold E. Swift
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Patent number: 4350522Abstract: Compounds of the formula ##STR1## wherein X is a hydrogen atom, a halogen atom, a trihalomethyl group, an alkyl group, or a cyano group,Y is a hydrogen atom, a halogen atom, or a trihalomethyl group, andZ is a hydroxy group, an alkoxy group, an alkyl group, a halogen atom, an amino group, an alkylthio group, a cyano group, a carboxy group, a carbalkoxy group, a carboxyalkyl group, a carbalkoxyalkyl group, an alkanoyloxy group, or a carbamoyloxy group,and compositions containing these compounds exhibit herbicidal activity.Type: GrantFiled: September 1, 1978Date of Patent: September 21, 1982Assignee: Rohm and Haas CompanyInventors: Horst O. Bayer, Colin Swithenbank
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Patent number: 4342877Abstract: Process for the preparation of Compound I by treating Compound II with X.sub.2 or SO.sub.2 X.sub.2 in the presence of a free radical initiator and an anhydride having the formula (RCO).sub.2 O while eliminating the acid halide formed having the formula RCOX from the reaction mixture, wherein Compounds I and II have the formulas ##STR1## and R is C.sub.1 -C.sub.3 alkyl, X is Cl or Br and n is 1, 2 or 3.Type: GrantFiled: November 13, 1979Date of Patent: August 3, 1982Assignee: Eastman Kodak CompanyInventors: Dah-Chieh O. Cheng, Joseph S. Bowers, Jr., Ronald J. Maner
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Patent number: 4337209Abstract: An alkali metal salt of an organic carboxylic acid, i.e. a soap, is prepared by saponifying the corresponding organic carboxylic acid, its ester or mixtures thereof with a concentrated aqueous solution of alkali metal hydroxide in the presence of an inorganic salt, in a liquid reaction medium comprising acetone, separating the organic salt from the reaction medium and removing excess acetone from the organic salt. The inorganic salt, i.e. soap, so produced is in the form of a dry finely divided powder.Type: GrantFiled: January 16, 1981Date of Patent: June 29, 1982Assignee: Internationale Octrooi Maatschappij "Octropa" B.V.Inventors: John B. Akers, Jane A. Littler, David C. Peters
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Patent number: 4334094Abstract: This invention pertains to the production of higher homologues of aliphatic carboxylic acids by reaction of said acids with carbon monoxide and hydrogen in the presence of one or more palladium-containing catalysts in combination with a Group VB tertiary donor ligand and in the presence of an iodide or bromide promoter.Type: GrantFiled: June 30, 1980Date of Patent: June 8, 1982Assignee: Texaco Inc.Inventor: John F. Knifton
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Patent number: 4328163Abstract: A process for preparing a secondary or tertiary 2-carboxyethyl- or carboxymethylphosphine or a salt thereof comprisessaponifying the corresponding cyanoalkyl phosphine with an aqueous-alcoholic alkali metal hydroxide solution, to prepare the alkali metal salt of the corresponding phosphino carboxylic acid,treating an aqueous solution of the acid salt so produced with a strongly acidic ion exchanger, andneutralizing the resultant free acid with an alkali metal hydroxide, ammonia or an amine when a salt thereof is to be prepared.Type: GrantFiled: January 17, 1980Date of Patent: May 4, 1982Assignee: Chemische Werke Huels, A.G.Inventor: Peter Hanssle
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Patent number: 4323702Abstract: A process for recovering carboxylic acids with a material of which the main component is a polymeric compound having a pyridine skeletal structure and a crosslinked structure, followed by desorbing the captured carboxylic acids by use of a desorbing agent.Type: GrantFiled: November 17, 1980Date of Patent: April 6, 1982Assignee: Koei Chemical Co., Ltd.Inventors: Nariyoshi Kawabata, Shinichi Yasuda, Takeshi Yamazaki
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Patent number: 4317925Abstract: A process for the preparation of di-n-propylacetic acid which comprises the steps ofA. converting n-valeraldehyde-diallyl acetal into allyl-1-pentenyl ether by cleaving one mol of allyl alcohol per one mol of n-valeraldehye-diallyl acetal;B. rearranging the allyl-1-pentenyl ether thermally into 2-propyl-pent-4-en-1-al,C. partially hydrogenating the 2-propyl-pent-en-1-al catalytically to form 2-propyl valeraldehyde, andD. oxidizing the 2-propyl valeraldehyde to form dipropyl-acetic acid.Type: GrantFiled: July 25, 1979Date of Patent: March 2, 1982Assignee: Ruhrchemie AktiengesellschaftInventors: Jurgen Weber, Wolfgang Bernhagen, Helmut Springer
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Patent number: 4315867Abstract: Secondary and tertiary 2-carboxyethyl or carboxymethylphosphines or a salt thereof, of the formulaR--P(CH.sub.2 COOMe).sub.2 or R--P(CH.sub.2 --CH.sub.2 --COOMe).sub.2whereinMe is hydrogen, an alkali metal or NR'.sub.4 wherein R' is hydrogen, C.sub.1-10 alkyl or C.sub.6-14 aryl, andR is hydrogen or a saturated or unsaturated, aliphatic or cycloaliphatic group of 1-20 carbon atoms and, for the 2-carboxyethylphosphines, also C.sub.6-14 aryl,are useful as components in catalysts for ethylene oligomerization.Type: GrantFiled: January 17, 1980Date of Patent: February 16, 1982Assignee: Chemische Werke Huels, AktiengesellschaftInventor: Peter Hanssle
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Patent number: 4311854Abstract: A process for the preparation of di-n-propyl-acetic acid, comprising the steps of:A. catalytically reacting n-butyric acid with cleavage of carbon dioxide and water to form heptanone-4;B. hydrogenating heptanone-4 in teh presence of a catalyst to form heptanol-4;C. dehydrating heptanol-4 in the presence of an Al.sub.2 O.sub.3 catalyst to form heptene-3;D. hydroformylating heptene-3 in the presence of a rhodium complex compound as catalyst to form a mixture of 2-propyl pentanal and 2-ethyl hexanal;E. oxidizing the 2-propyl pentanal/2-ethyl hexanal mixture to form a mixture of di-n-propyl acetic acid and 2-ethyl hexanoic acid, andF. separating the mixture of di-n-propyl acetic acid and 2-ethyl hexanoic acid to recover pure di-n-propyl acetic acid.If desired, step B can be carried out without purification of the product of step A. Moreover, the dehydration of step C can be carried out without previous purification of the product of step B.Type: GrantFiled: July 25, 1979Date of Patent: January 19, 1982Assignee: Ruhrchemie AktiengesellschaftInventors: Jurgen Weber, Volker Falk, Claus Kniep
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Patent number: 4284796Abstract: A process for the preparation of a 4-acyloxy-2-methyl-crotonaldehyde of the formula ##STR1## where R is hydrogen or an aliphatic radical of 1 to 5 carbon atoms, by reacting a 1,1,4-triacyloxy-2-methyl-but-2-ene of the formula ##STR2## where R.sup.1 and R.sup.2 are each hydrogen or an aliphatic radical of 1 to 5 carbon atoms, with water in the presence of a carboxylic acid of the formulaR--COOH III.Type: GrantFiled: September 25, 1979Date of Patent: August 18, 1981Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Hans-Martin Weitz
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Patent number: 4273936Abstract: A one-step process is disclosed for forming a carboxylic acid and its anhydride directly from the corresponding olefin which comprises reacting the olefin with carbon monoxide, hydrogen and oxygen in the presence of a stable rhodium complex catalyst. The rhodium catalyst is stabilized by a pentavalent Group V ligand, such as a phosphine oxide. The reaction is preferably conducted in an inert organic solvent. In an alternate embodiment, a carboxylic acid may be obtained by oxidation of an aldehyde (produced, for example, by hydroformylation of the corresponding olefin) in the presence of a rhodium complex catalyst stabilized by a pentavalent Group V ligand. This reaction is also preferably conducted in an inert organic solvent.Type: GrantFiled: June 16, 1980Date of Patent: June 16, 1981Assignee: Union Carbide CorporationInventors: Rocco A. Fiato, Roy L. Pruett
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Patent number: 4269705Abstract: A method of removing chromium ion from an aqueous solution of an organic acid of an acid concentration of up to 95% which comprises treating the solution with a cation exchange resin at a temperature higher than 55.degree. C.Type: GrantFiled: April 18, 1979Date of Patent: May 26, 1981Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Teruhiko Yoshioka, Hideo Matsuzawa, Kazuya Okada, Minoru Ikeda
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Patent number: 4263443Abstract: Hydrocarbons and esters and/or acids are produced by heating aldehydes in the presence of an alcohol or an alcohol equivalent and in the presence of an iodine or bromine moiety and a rhodium or iridium catalyst.Type: GrantFiled: November 22, 1978Date of Patent: April 21, 1981Assignee: Halcon Research and Development Corp.Inventor: John F. White
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Patent number: 4260820Abstract: This invention pertains to the production of higher homologues of aliphatic carboxylic acids by reaction of said acids with carbon monoxide and hydrogen in the presence of one or more ruthenium catalyst components and an iodide or bromide promoter.Type: GrantFiled: September 24, 1979Date of Patent: April 7, 1981Assignee: Texaco Development Corp.Inventor: John F. Knifton
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Patent number: 4250331Abstract: Process for recovering carboxylic acids from dilute aqueous solutions of alkali metal salts of such carboxylic acids by mixing such solutions with from 10 to 1000% of a supercritical solution comprising at least 10 mole % carbon dioxide at a pressure from 80 to 500 atm and preferably 100 to 350 atm and at a temperature of from 35.degree. to 200.degree. C. and preferably from 35.degree. to 100.degree. C. whereby the salt reacts with the carbon dioxide to form the carboxylic acid which dissolves in the supercritical fluid. The aqueous phase is allowed to separate from the supercritical fluid phase. The pressure of the supercritical phase is lowered which lowers the solubility of the carboxylic acid in the supercritical fluid so that an acid phase is formed separate from the supercritical fluid phase whereby recovery of the acid is effected.Type: GrantFiled: October 9, 1979Date of Patent: February 10, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventor: Edward J. Shimshick
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Patent number: 4242265Abstract: New indolylalkyl esters of mercaptoalkanoic acids, and salts thereof, which have the general formula ##STR1## are useful as hypotensive agents.Type: GrantFiled: January 10, 1979Date of Patent: December 30, 1980Assignee: E. R. Squibb & Sons, Inc.Inventors: Peter C. Wade, Miguel A. Ondetti
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Patent number: 4238294Abstract: A process for recovering heavy metal ions or heavy metal ions and halogen values from a solution comprising a lower aliphatic monocarboxylic acid, which comprises the steps of:(1) contacting a lower aliphatic carboxylic acid solution containing heavy metal ions or heavy metal ions and halogen values with an anion exchange resin, at least 60% of the ion-exchange groups of said anion exchange resin being in the bromide or chloride state, while the water concentration in the lower aliphatic monocarboxylic acid solution has been adjusted to a level lower than 20% by weight, thereby to adsorb the heavy metal ions or the heavy metal ions and the halogen values on the anion exchange resin; and(2) desorbing the adsorbed heavy metal ions or the adsorbed heavy metal ions and the adsorbed halogen values from the anion exchange resin by elution with an eluent.Type: GrantFiled: July 28, 1978Date of Patent: December 9, 1980Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Hiroshi Takeuchi, Tetsuya Miyake, Masatoshi Tanouchi, Tatsushi Saeki, Kazuki Ban
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Patent number: 4230887Abstract: C.sub.2 -C.sub.6 monocarboxylic and dicarboxylic acids are scrubbed from gas phase mixtures of such acids and water by gas absorption techniques utilizing a liquid solvent comprising a polyoxyalkylene glycol or a monoalkyl or dialkyl ether thereof. The solvent enriched with the acid is subjected to distillation to recover a substantially anhydrous acid product.Type: GrantFiled: February 16, 1978Date of Patent: October 28, 1980Assignee: Celanese CorporationInventors: William T. Mitchell, Phillip S. Snyder
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Patent number: 4218386Abstract: A process for hydrolyzing triglyceride having its carboxylic acid moieties containing from 6 to 26 carbon atoms involves reacting with water in the presence of low molecular weight displacing acid catalyst, strong acid catalyst and sufficient water to form water and oil phases, to produce carboxylic acids corresponding to said moieties and glycerine.Type: GrantFiled: June 15, 1978Date of Patent: August 19, 1980Assignee: The Procter & Gamble CompanyInventors: Ted J. Logan, David C. Underwood, Tom C. Rheinecker
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Patent number: 4217460Abstract: Carboxylic acids of the general formula IR.sup.1 -COOH Iwhere R.sup.1 is hydrogen, methyl, ethyl or vinyl, are isolated from their dilute aqueous solutions by extraction followed by distillation of the mixtures obtained, the extractant used being a secondary amide of the general formula II ##STR1## where R.sup.2 and R.sup.3 are alkyl, cycloalkyl, aryl or aralkyl or conjointly are 1,4- or 1,5-alkylene, in each case of not more than 8 carbon atoms, with the proviso that the sum of the carbon atoms of R.sup.2 and R.sup.3 is from 7 to 14 and that only one of these radicals is aryl, and where R.sup.4 is one of the radicals R.sup.1.Type: GrantFiled: April 6, 1978Date of Patent: August 12, 1980Assignee: BASF AktiengesellschaftInventors: Heinz Hohenschutz, Johannes E. Schmidt, Hans Kiefer
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Patent number: 4215225Abstract: An ammonium salt of an alkanoic acid having about 1-10 carbon atoms per molecule is prepared by reacting ammonia with an excess of the alkanoic acid in an aqueous system in a tubular reactor.An ammonium salt of an alkanoic acid having about 12-18 carbon atoms per molecule is prepared by reacting ammonia with the alkanoic acid in a tubular reactor. The reaction can be conducted in the presence or absence of water.Type: GrantFiled: July 28, 1978Date of Patent: July 29, 1980Assignee: W. R. Grace & Co.Inventors: Andrew B. Funk, Max B. Williams
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Patent number: 4187153Abstract: According to the present invention an impure liquid containing ethylene glycol or propylene glycol, lower carboxylate esters of the glycol, water, carboxylic acid and glycol-azeotroping agent is treated for removal of substantially all of said glycol-azeotroping agent by a process which comprises distilling the impure liquid in a distillation zone to form an overheads product comprising water and glycol-azeotroping agent and a bottoms product comprising the glycol, esters and carboxylic acid, which is substantially free of said glycol-azeotroping agent, said bottoms product containing water in an amount of at least about 1 weight percent of the amount of water passed to said distillation zone with said impure liquid.Type: GrantFiled: November 14, 1977Date of Patent: February 5, 1980Assignee: Halcon Research & Development CorporationInventors: Alan Peltzman, Charles C. Yang
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Patent number: 4185027Abstract: A process for hydrolyzing methyl esters having carboxylic acid moieties containing 6 to 22 carbon atoms involves reacting said esters with water in the presence of carboxylic acid and strong acid catalysts to produce acid corresponding to reactant ester and methanol and driving the reaction toward completion by removing the methanol.Type: GrantFiled: June 15, 1978Date of Patent: January 22, 1980Assignee: The Procter & Gamble CompanyInventor: Ted J. Logan
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Patent number: 4167510Abstract: Improved fugitive tints are provided wherein such tints are characterized as having from 2 to about 300 repeating alkyleneoxy capped units in the molecule and having a dyestuff molecule attached to the alkyleneoxy capped units. The solubility of the tint compositions can be altered by varying the number of alkyleneoxy capped units in the tint molecule. The fugitive tints are characterized by the formulaR{A--(alkyleneoxy constituent).sub.n R.sub.1 ].sub.m }.sub.xwherein R--A is an organic dyestuff molecule, A is a linking moiety in said organic dyestuff molecule selected from the group consisting of N, O, S, or CO.sub.2, the alkylene moiety of the alkyleneoxy constituent contains from 2 to about 4 carbon atoms, n is an integer of from 2 to about 300, m is 1 when A is O, S, or CO.sub.2 and 2 when A is N, x is an integer of from 1 to about 5, and the product of n times m times x (n.multidot.m.multidot.x) is from 2 to about 300, and R.sub.1 is ##STR1## and sulfonates and sulfates thereof in which R.sub.Type: GrantFiled: January 23, 1978Date of Patent: September 11, 1979Assignee: Milliken Research CorporationInventor: Ralph N. Brendle
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Patent number: 4143066Abstract: A lower carboxylic acid such as acetic acid is separated and recovered from an aqueous medium by the steps which include contacting, in an extraction zone, the aqueous medium with an extracting agent such as trioctyl phosphine oxide dissolved in an organic solvent such as a mixture of paraffins having a boiling range of about 160.degree. C. to 175.degree. C.Type: GrantFiled: December 16, 1976Date of Patent: March 6, 1979Assignee: The Dow Chemical CompanyInventor: Victor Kalcevic
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Patent number: 4142059Abstract: An aqueous solution of sodium or potassium 2-ethylhexanoate is spray dried in a spray drier having an inlet temperature ranging from about 100.degree. C. to about 160.degree. C. and an outlet temperature ranging from 60.degree. C. to about 130.degree. C. to provide the corresponding sodium or potassium 2-ethylhexanoate having a moisture content of from about 0.5 to about 5.0 percent by weight and having improved purity and crystalline texture.Type: GrantFiled: July 29, 1977Date of Patent: February 27, 1979Assignee: Eli Lilly and CompanyInventors: James M. Greene, Sigmund A. Schildcrout, Gary D. Zintgraff
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Patent number: 4127604Abstract: Process for the preparation of di-n-propyl acetic acid of formula: ##STR1## and its non-toxic alkali and alkaline earth metal salts whereby in a single stage, sodium n-propylate in n-propanol medium is added to a reaction medium formed of a cyanacetic ester of general formula: ##STR2## in which R represents an alkyl radical having from 1 to 4 carbon atoms, and n-propyl bromide or iodide, the alkylation reaction taking place under reflux, the crude ester obtained is saponified with a 10 to 20% solution of sodium or potassium hydroxide, the salt thus obtained is acidified with a strong acid, to give the crude di-n-propyl cyanacetic acid, which is decarboxylated by heating at a temperature between 140.degree. and 190.degree. C, to provide the di-n-propyl acetonitrile, the di-n-propyl acetonitrile obtained is hydrolysed by means of an aqueous solution of 75 to 80% sulphuric acid at a temperature of 80.degree.-140.degree.Type: GrantFiled: May 25, 1977Date of Patent: November 28, 1978Assignee: LabazInventors: Michel Chignac, Claude Grain, Charles Pigerol
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Patent number: 4119652Abstract: Process for the homogeneous catalytic hydrogenation of olefins, capable of existing as enantiomorphs upon hydrogenation of the olefinic bond, which yields on hydrogenation an optically active mixture. The process comprises the hydrogenation of the olefin in the presence of an optically active coordinated metal hydrogenation catalyst, in which the metal is selected from the group consisting of rhodium, iridium, ruthenium, osmium, palladium and platinum.This process is a generalized process for any asymmetric hydrogenation of olefins in which one optical enantiomorph is desired. It is also a generalized process for the selective hydrogenation of olefins in the presence of other reactive groups which are easily hydrogenated. It is especially useful for the preparation of natural products which possess optical activity, such as amino acids, and for products such as flavors, fragrances which may require optical activity for their utilitization.Type: GrantFiled: June 25, 1976Date of Patent: October 10, 1978Assignee: Monsanto CompanyInventors: William S. Knowles, Milton J. Sabacky
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Patent number: RE29981Abstract: A process for the preparation of organic carboxylic acids which comprises converting a formic acid ester expressed by the general formulaHCOORwherein R stands for a chain or cyclic aliphatic hydrocarbon radical which may have an aliphatic unsaturation, an aryl radical, an aralkyl radical or a heterocyclic radical,At an elevated temperature under raised pressure of carbon monixide to an organic carboxylic acid expressed by the general formulaRCOOHwherein R is as defined above.Type: GrantFiled: July 22, 1977Date of Patent: May 1, 1979Assignee: Mitsubishi Gas Chemical Company, Inc.Inventor: Nobuo Isogai