Aldehyde Or Ketone Patents (Class 562/577)
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Patent number: 4902828Abstract: Aqueous glyoxylic acid solutions, essentially free of other acids, are recovered from aqueous solutions which still contain other acids, by a method in which the aqueous solution is mixed with an organic nitrogen compound at as high as 50.degree. C., the phases are separated, and the glyoxylic acid is extracted from the organic phase with water, at a higher temperature.Type: GrantFiled: October 18, 1984Date of Patent: February 20, 1990Assignee: BASF AktiengesellschaftInventors: Gerhard Wickenhaeuser, Bernd Heida, Fritz Graf, Leopold Hupfer
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Patent number: 4898974Abstract: Dichloropinacolone is produced by introducing into pinacolone twice the molar amount of chlorine, the exothermic reaction mass being cooled initially to maintain the temperature below about 50.degree. C. until about 60 to 80% of the chlorine has been introduced, and then heating the reaction mass to a temperature above 50.degree. C. during introducing of the remainder of the chlorine, thereby to produce dichloropinacolone, and terminating chlorine introduction when the dichloropinacolone content of the reaction mass is at least about 97%. The molten product is added to an aqueous solution of an alkali maintained at a temperature of at least about 50.degree. C., the alkali being present in more than three times the molar amount of the dichloropinacolone. To the resulting solution of a salt of 3,3-dimethyl-2-hydroxy-butyric acid, brought to a pH of about 9 to 12, there is added approximately the stoichiometric amount of potassium permanganate. Solid MnO.sub.Type: GrantFiled: April 23, 1985Date of Patent: February 6, 1990Assignee: Bayer AktiengesellschaftInventors: Karlfried Dickore, Hans D. Engels, Hans Kratzer, Walter Merz
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Patent number: 4867849Abstract: There is disclosed an improved process for the manufacture of glyoxylic acid obtained by oxidation of glycolic acid. For processing purposes alkyl esters of these acids are employed. Increased efficiency is obtained by recovering glycolate rich streams from one or more distillation operations and after treatment to remove acetic acid by-product the streams are recycled to the oxidation reaction.Type: GrantFiled: July 25, 1988Date of Patent: September 19, 1989Inventors: Dario R. Cova, John M. Thorman
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Patent number: 4827004Abstract: Novel Isoprene Derivatives which have mucosa-protective and gastric acid secretion-inhibiting properties and are useful for combatting ulcers both by treating and as a prophylaxis against gastric and/or duodenal ulcers.Type: GrantFiled: August 24, 1987Date of Patent: May 2, 1989Assignee: Hoffmann-La Roche Inc.Inventors: Albert Fischli, Max Schmid, Rudolf Schmid
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Patent number: 4758594Abstract: Novel compounds and compositions which inhibit SRS-A in mammals are disclosed. Methods for preparing said compounds and compositions and methods for their use for treating allergic reactions, inflammation and for reducing the severity of myocardial infarction resulting from heart attack are disclosed.Useful intermediates for preparing said compounds are also disclosed.Type: GrantFiled: May 19, 1986Date of Patent: July 19, 1988Assignee: Schering CorporationInventors: Anil K. Saksena, Jesse K. Wong, Pietro Mangiaracina
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Patent number: 4738802Abstract: A process for the production of an alkyl .alpha.-keto-carboxylic acid of the general formula: ##STR1## wherein: R is a linear or branched alkyl radical having from 1 to about 20 carbon atoms which comprises reacting an alkyl halide of the formula:RXwhere R is as defined above and X represents halogen, in a liquid solvent medium, with carbon monoxide at elevated temperature and pressure in the presence of a catalytic amount of a metal carbonyl compound and an alkali metal inorganic base or an alkaline earth metal inorganic base. Optionally, small amounts of LiI and/or bis(1,2-diphenylphosphino)ethane may be present in the reaction as co-catalysts.Type: GrantFiled: November 16, 1983Date of Patent: April 19, 1988Assignee: Ethyl CorporationInventor: John Y. Lee
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Patent number: 4705867Abstract: 1,2-Dithiolane-3-pentanoic acid (D,L-thioctic acid) of the formula ##STR1## is prepared by a process comprising (a) reacting a 2-(3-alkylthiopropionyl)-cyclopentanone-1 of the formula ##STR2## where R is a C.sub.1 -C.sub.4 alkyl, phenyl or benzyl in aqueous alkaline solution at a temperature of about 20.degree. C. to about 90.degree. C. to form the corresponding carboxylic acid of formula VI ##STR3## (b) reacting the compound of formula VI with an alkyl mercaptan at a temperature between -20.degree. C. and 0.degree. C. to form the corresponding thioketal of formula VII ##STR4## (c) reacting the compound of formula VII with sodium in liquid ammonia at a temperature between -60.degree. C. and -10.degree. C.Type: GrantFiled: April 4, 1986Date of Patent: November 10, 1987Assignee: Degussa AktiengesellschaftInventors: Guenes Giray, Klaus Huthmacher, Axel Kleemann, Thomas Lied
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Patent number: 4649217Abstract: Oxocarboxylic acids, for example adipaldehydic acid can be advantageously produced by a process, in which cyclohexanones are oxidized with molecular oxygen in the presence of water and iron or iridium compound, preferably also in the presence of a sulfur or organic nitrogen compound.Type: GrantFiled: March 15, 1983Date of Patent: March 10, 1987Assignee: Mitsubishi Chemical Industries LimitedInventors: Takao Maki, Kenji Murayama, Yoshio Asahi
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Patent number: 4647413Abstract: Perfluoropolyether oligomers or block polymers, having a backbone with one or a plurality of perfluoropolyether segments each consisting essentially of (1) at least one perfluoroisopropyleneoxy unit, (2) a bis(perfluoromethyleneoxy-terminated) unit, and (3) a perfluoroethylidene unit terminating each segment, the backbone of the perfluoropolyether being terminated with COF and/or a functional or nonfunctional derivative thereof, said perfluoropolyethers being made by reacting a perfluoroaliphatic diacid fluoride with hexafluoropropylene epoxide to produce an acid fluoride-terminated perfluoropolyether adduct or oligomer which then can be photopolymerized to yield an acid fluoride-terminated perfluoropolyether block polymer. These oligomers and block polymers are useful as high temperature lubricants, hydraulic fluids, gaskets, adhesives and coatings as well as co-reactants wtih urethane in forming propellant binders.Type: GrantFiled: January 20, 1984Date of Patent: March 3, 1987Assignee: Minnesota Mining and Manufacturing CompanyInventor: Patricia M. Savu
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Patent number: 4643994Abstract: This invention relates to novel organic trithio oxides of the formula:R.sup.1 --X --R--X.sup.1 --R.sup.1wherein R is selected from --CH.sub.2 CH.dbd.CH--, ##STR1## and (CH.sub.2).sub.3 ; X is selected from ##STR2## X.sup.1 is selected from --S--S, ##STR3## and, each R.sup.1 is independently selected from carboxyalkyl, alkoxy, alkylthio, amino, alkylamino and acyl substituted and unsubstituted lower alkyl, lower alkenyl, lower alkynyl, phenyl and lower alkylphenyl; provided when R is --CH.sub.2 CH.dbd.CH--, X is ##STR4## and X.sup.1 is --S--S--, then R.sup.1 is not in both instances --CH.sub.2 CH.dbd.CH.sub.2.This invention also relates to a method of preparing the above-identified compounds by heating and further oxidizing various oxides of organic disulfides and to antithrombotic uses of the compounds.Type: GrantFiled: December 17, 1984Date of Patent: February 17, 1987Assignee: The Research Foundation of State University of New YorkInventors: Eric Block, Saleem Ahmad
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Patent number: 4628117Abstract: An improved process for the ozonization of .alpha.,.beta.-unsaturated cyclohexanones, most notably isophorone and piperatone, to produce 5-ketoalkanoic acids is provided. For the process, the .alpha.,.beta.-unsaturated cyclohexanone is ozonized in an aliphatic monocarboxylic acid participating solvent which may optionally contain water and a soluble manganous salt.Type: GrantFiled: February 4, 1985Date of Patent: December 9, 1986Assignee: National Distillers and Chemical CorporationInventor: Hubert J. Sharkey
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Patent number: 4628118Abstract: The following process steps are shown: ##STR1## Intermediates I, II and IV are new. End product III is known, useful as an intermediate in the manufacture of pesticides, pharmaceuticals and dyestuffs.Type: GrantFiled: October 10, 1985Date of Patent: December 9, 1986Assignee: Bayer AktiengesellschaftInventor: Dieter Arlt
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Patent number: 4620034Abstract: Preparation of 2-keto-aldonic acids, e.g., 2-keto-gluconic acid, by oxidizing an aldose, e.g. glucose, or aldonic acid in aqueous solution with molecular oxygen. Use is made of a platinum catalyst together with a catalytic amount of lead and/or bismuth and/or a compound thereof. The pH of the solution is in the range of from 4 to 12 and preferably in the range of from 7 to 9. The reaction may be carried out at a temperature in the range of 0.degree. to 200.degree. C. and preferably in the range of from 25.degree. to 80.degree. C.Type: GrantFiled: January 22, 1985Date of Patent: October 28, 1986Assignee: Akzo NVInventor: Peter C. C. Smits
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Patent number: 4614816Abstract: A carboxylic acid or an ester thereof having at least two carbon atoms more than formic acid is prepared by reacting at elevated temperature e.g. 100.degree. to 250.degree. C. formic acid or a formate ester with an olefin e.g. ethylene in the presence of, as catalyst, a Group VIII noble metal e.g. iridium, preferably promoted by iodide, to cause addition of the formic acid or ester to the olefin and form the a higher acid e.g. propionic acid or ester thereof.A strong acid such as a sulphonic acid may be used as a copromoter. The catalyst is employed in solution.Type: GrantFiled: October 13, 1983Date of Patent: September 30, 1986Assignee: BP Chemicals LimitedInventors: David J. Drury, Peter S. Williams
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Patent number: 4614822Abstract: Sodium 3,3-dimethyl-2-hydroxybutyrate and ruthenium dioxide hydrate are added to water, the pH rendered alkaline, and sodium hypochlorite is slowly added to produce sodium 3,3-dimethyl-2-oxobutyrate in high yield and purity. The solid catalyst is filtered off and may be re-used while the filtrate can be directly used in further synthesis.Type: GrantFiled: August 26, 1980Date of Patent: September 30, 1986Assignee: Mobay Chemical CorporationInventor: Dennis E. Jackman
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Patent number: 4612391Abstract: This invention provides a process for the conversion of an alicyclic .alpha.,.beta.-olefinically unsaturated ketone compound to an acyclic oxocarboxylic acid product which contains at least one less carbon atom per molecule than the ketone starting material.The conversion involves ozonation of the alicyclic .alpha.,.beta.-olefinically unsaturated ketone in an aqueous alcohol reaction medium, followed by a heating step.Type: GrantFiled: September 22, 1980Date of Patent: September 16, 1986Assignee: Philip Morris IncorporatedInventor: William B. Edwards, III
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Patent number: 4599446Abstract: A process for the preparation of 2-keto-L-gulonic acid by the oxidation of L-sorbose with an oxygen-containing gas in water used as the solvent, wherein the reaction is carried out in the presence of a specific catalyst, preferably with the pH of the reaction fluid kept within the range of 6 to 10. The catalyst contains platinum and/or palladium, as well as lead or bismuth. 2-Keto-L-gulonic acid is a compound which is useful as a precursor of vitamin C.Type: GrantFiled: April 17, 1985Date of Patent: July 8, 1986Assignee: Mitsui Toatsu Chemicals, IncorporatedInventor: Tadamitsu Kiyoura
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Patent number: 4567004Abstract: Monomethyl-substituted methylene compounds are obtained by reacting methylene compounds of the formula ##STR1## in which R.sup.1 and R.sup.2 independently of one another represent --CN, --CO--R.sup.3, --SO.sub.2 --R.sup.3 or --NO.sub.2 andR.sup.1 can additionally denote -aryl(R.sup.1).sub.n,whereinR.sup.3 denotes --OH, alkyl, aralkyl, aryl, alkoxy, aralkoxy or aryloxy, or amino which is substituted by alkyl and/or aralkyl and/or aryl, and furthermoretwo radicals R.sup.3 together can be an alkylene group, the radical of an aliphatic diol or of an aliphatic diamine or the group --NH--CO--NH-- and n represents 1, 2 or 3,with formaldehyde and with hydrogen in the presence of a condensation catalyst and a hydrogenation catalyst at elevated temperature, the methylene compound being introduced into the liquid phase of the mixture of reactants in the course of the reaction.Type: GrantFiled: July 18, 1984Date of Patent: January 28, 1986Assignee: Bayer AktiengesellschaftInventors: Heinz U. Blank, Erich Wolters
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Patent number: 4564704Abstract: Dichloropinacolone is produced by introducing into pinacolone twice the molar amount of chlorine, the exothermic reaction mass being cooled initially to maintain the temperature below about 50.degree. C. until about 60 to 80% of the chlorine has been introduced, and then heating the reaction mass to a temperature above 50.degree. C. during introducing of the remainder of the chlorine, thereby to produce dichloropinacolone, and terminating chlorine introduction when the dichloropinacolone content of the reaction mass is at least about 97%. The molten product is added to an aqueous solution of an alkali maintained at a temperature of at least about 50.degree. C., the alkali being present in more than three times the molar amount of the dichloropinacolone. To the resulting solution of a salt of 3,3-dimethyl-2-hydroxy-butyric acid, brought to a pH of about 9 to 12, there is added approximately the stoichiometric amount of potassium permanganate. Solid MnO.sub.Type: GrantFiled: January 22, 1981Date of Patent: January 14, 1986Assignee: Bayer AktiengesellschaftInventors: Karlfried Dickore, Hans D. Engels, Hans Kratzer, Walter Merz
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Patent number: 4558153Abstract: Carboxylic acids having two or more carbon atoms than formic acid, or esters of such carboxylic acids are prepared by reacting either formic acid or an ester of formic acid with an olefin at elevated temperature in the presence of a Group VIB metal catalyst. The Group VIB metal which is chromium, molybdenum or tungsten is suitably added as a carbonyl or carbonyl halide. In addition to the catalyst a halide promoter and a phosphorus containing copromoter may optionally be added. The process can be used, for example to prepare propionic acid or a propionic acid ester from ethylene and either formic acid of an ester of formic acid.Type: GrantFiled: October 23, 1984Date of Patent: December 10, 1985Assignee: BP Chemicals LimitedInventor: John Cook
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Patent number: 4556732Abstract: Novel 3-formyl-4-methyl-pent-3-ene-1-oic acid of the formula ##STR1## and a process for its preparation and intermediates and a process for the preparation of compounds of the formula ##STR2## wherein W is selected from the group consisting of hydrogen and R.sub.1 of an optionally chiral alcohol R.sub.1 OH, useful as an intermediate for the production of numerous esters having elevated insecticidal activity.Type: GrantFiled: May 27, 1980Date of Patent: December 3, 1985Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
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Patent number: 4529704Abstract: A device for preparing a control solution for ketone analysis is disclosed, as well as a method for preparing it. The device comprises a carrier vehicle incorporated with an ester of a .beta.-ketoalkanoic acid, and a hydrolyzing substance capable of converting the ester to the corresponding .beta.-ketoalkanoic acid. The ester has the structure ##STR1## in which R is a lower alkyl group and R' is an aliphatic or cyclic group having 1 to about 7 carbon atoms. The method comprises contacting a predetermined volume of solvent with the device.Type: GrantFiled: November 25, 1981Date of Patent: July 16, 1985Assignee: Miles Laboratories, Inc.Inventors: Robert W. Trimmer, William I. White
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Patent number: 4511734Abstract: Process for the production of 3,3-dimethylglutaric acid from isophorone. In a first step the isophorone is converted with ozone into an ozone-addition product. The ozone-addition product is converted by hydrolysis into 3,3-dimethyl-5-oxohexanoic acid. The latter is converted into 3,3-dimethylglutaric acid by treatment with hydrogen peroxide.Type: GrantFiled: May 5, 1982Date of Patent: April 16, 1985Assignee: Lonza Ltd.Inventors: Pavel Lehky, Peter Hardt
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Patent number: 4503246Abstract: A process for the preparation of glyoxylic acid is disclosed which comprises reacting an aqueous solution of glyoxal with chlorine. The reaction is preferably carried out under pressure, under the condition that the hydrochloric acid concentration in the aqueous solution of glyoxal is 1 to 15%. The reaction can be carried out in the presence of a catalytically effective amount of bromine as a catalyst.Type: GrantFiled: December 1, 1981Date of Patent: March 5, 1985Assignee: Daicel Chemical Industries, Ltd.Inventors: Tadayuki Mitani, Mamoru Endo
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Patent number: 4500720Abstract: Novel 3-formyl-4-methyl-pent-3-ene-1-oic acid of the formula ##STR1## and a process for its preparation and intermediates and a process for the preparation of compounds of the formula ##STR2## wherein W is selected from the group consisting of hydrogen and R.sub.1 of an optionally chiral alcohol R.sub.1 OH, useful as an intermediate for the production of numerous ester having elevated insecticidal activity.Type: GrantFiled: January 19, 1984Date of Patent: February 19, 1985Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
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Patent number: 4487957Abstract: A novel alkyl 4-methyl-3-formyl-penten-1-oate of the formula ##STR1## wherein R is alkyl of 1 to 5 carbon atoms and the dotted lines represent a double bond in the 3,4 or 4,5-position and their preparation and novel intermediates therefore and a novel process for the preparation of 4-methyl-3-formyl-pent-3-en-1-oic acid which is an intermediate for the preparation of compounds of the formula ##STR2## wherein R.sub.3 is selected from the group consisting of hydrogen and the residue of an alcohol R.sub.3 OH by the process of European Patent Application Ser. No. 0023849 published Feb. 11, 1981, which are used to prepare very active insecticidal esters.Type: GrantFiled: April 21, 1983Date of Patent: December 11, 1984Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
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Patent number: 4487972Abstract: This specification discloses a process for the production of oxygenated compounds, more specifically aldehydes and alcohols, by reacting an olefin with hydrogen and carbon monoxide in the presence of, as a ctalyst, an insoluble polymer containing a functional group, which may be an amine, thiol, phosphine, or arsine group, having chemically bonded thereto a metal of Group VIII of the Periodic Table. The metal can be, for example, rhodium, cobalt, or ruthenium. The olefin can contain more than one carbon-to-carbon double bond, may be an open chain or a cyclic olefin, and may be substituted. Further, the olefin may be contained in a refinery stream such as a cracked gasoline. The reaction may be carried out in the presence of a polar solvent.Type: GrantFiled: April 22, 1980Date of Patent: December 11, 1984Assignee: Mobil Oil CorporationInventors: Werner O. Haag, Darrell D. Whitehurst
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Patent number: 4465863Abstract: Described are compounds defined according to the structure: ##STR1## wherein R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 represent hydrogen or methyl with the provisos that:(i) the sum total of carbon atoms in R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 is three;(ii) when R.sub.7 is methyl, then R.sub.5 and R.sub.6 are both methyl, and(iii) when either R.sub.3 or R.sub.4 is methyl, then R.sub.7 is hydrogenand wherein R.sub.8 represents hydrogen, acetyl, alkoxyacyl, hydroxyacyl, or alkali metal carboxylate; and R.sub.9 is hydrogen or allyl with the additional proviso that R.sub.8 and R.sub.9 are not both hydrogen.Also described is the use of the subgenus of such compounds defined according to the structure: ##STR2## in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including solid or liquid nonionic, cationic, anionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, cosmetic powders, hair preparations and the like.Type: GrantFiled: November 12, 1982Date of Patent: August 14, 1984Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Steven D. Temes, Theodore J. Tyszkiewicz, Marie R. Hanna
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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: 4440740Abstract: A method and drug form enhancing the absorption of a rectally or orally administered drug from the rectal compartment into the blood stream of a warm blooded animal. The method includes the steps of preparing a drug form capable of being rectally and orally administered. The drug form comprises a therapeutically effective unit dosage amount of a selected drug of the type which is capable of being absorbed into the blood stream from the gastrointestinal area and an .alpha.-keto aldehyde or salts thereof being present in the drug form in a sufficient amount to be effective in enhancing the drug absorption rate, when administering the drug form to warm blooded animals.Type: GrantFiled: April 26, 1982Date of Patent: April 3, 1984Assignee: Merck & Co., Inc.Inventors: Joseph A. Fix, Stefano A. Pogany
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Patent number: 4414418Abstract: Process for the production of dimedone from isophorone. The isophorone is converted in the presence of a solvent with ozone into an ozone-addition product. An alcohol corresponding to the ester radical is added at the latest after the formation of the ozone-addition product for the formation of the intermediate product, 3,3-dimethyl-5-oxo-hexanoic acid ester. The ozone addition product is heated in the presence of acids to a temperature of 20.degree. to 150.degree. C. The 3,3-dimethyl-5-oxo-hexanoic acid ester is isolated thereby. The ester is then converted in a further step into dimedone by treatment of the ester with an alkali alcoholate in an anhydrous milieu.Type: GrantFiled: May 19, 1982Date of Patent: November 8, 1983Assignee: Lonza Ltd.Inventor: Pavel Lehky
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Patent number: 4390724Abstract: Novel 3-formyl-4-methyl-pentanoic acid derivatives of the formula ##STR1## wherein Y is an aromatic group, R.sub.2 and R.sub.3 are individually alkyl of 1 to 4 carbon atoms or taken together with the carbon atom to which they are attached form a carbon homocycle of 3 to 6 carbon atoms, the Rs are alkyl of 1 to 6 carbon atoms or together form a polymethylene of 2 to 3 carbon atoms and Z' is selected from the group consisting of --COOH and Z and Z is selected from the group consisting of cyano and --COOR.sub.1 wherein R.sub.1 is alkyl of 1 to 6 carbon atoms and their preparation which are useful for the preparation of 3-formyl-4-R.sub.2 R.sub.3 -but-3-ene-1-oic acid which is an intermediate for the preparation of a compound of the formula ##STR2## wherein R.sub.4 is hydrogen or the remainder of an alcohol of the formula R.sub.1 OH by the process of copending, commonly assigned U.S. patent application Ser. No. 153,338 filed May 27, 1980.Type: GrantFiled: April 16, 1982Date of Patent: June 28, 1983Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
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Patent number: 4390702Abstract: A 3-substituted-3-fluoropyruvic acid and its ester and salt of the formula: ##STR1## wherein R is a lower alkyl group, a lower alkanoyl group, a fluorinated lower alkanoyl group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted pyridyl group and R' is a hydrogen atom, an ester-forming residue or a salt-forming residue, and their production.Type: GrantFiled: December 29, 1980Date of Patent: June 28, 1983Assignees: Daikan Kogyo Co., Ltd., Shionogi and Co., Ltd.Inventors: Susumu Misaki, Masahiro Suefuji, Tadahiko Tsushima, Hiroshi Tanida
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Patent number: 4387245Abstract: A process for preparing diacetoneketogulonic acid comprises oxidizing diacetonesorbose in two or more oxidizing steps using different oxidizing agents in each step. In preferred embodiments the first oxidation is done electrochemically or using air and the second oxidation is via hypochlorite treatment.Type: GrantFiled: May 20, 1981Date of Patent: June 7, 1983Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Rolf Wittmann, Willi Wintermeyer, Jurgen Butzke
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Patent number: 4382037Abstract: Novel 3-formyl-4-methyl-pentanoic acid derivatives of the formula ##STR1## wherein Y is an aromatic group, R.sub.2 and R.sub.3 are individually alkyl of 1 to 4 carbon atoms or taken together with the carbon atom to which they are attached form a carbon homocycle of 3 to 6 carbon atoms, the Rs are alkyl of 1 to 6 carbon atoms or together form a polymethylene of 2 to 3 carbon atoms and Z' is selected from the group consisting of --COOH and Z and Z is selected from the group consisting of cyano and --COOR.sub.1 wherein R.sub.1 is alkyl of 1 to 6 carbon atoms and their preparation which are useful for the preparation of 3-formyl-4-R.sub.2 R.sub.3 -but-3-ene-1-oic acid which is an intermediate for the preparation of a compound of the formula ##STR2## wherein R.sub.4 is hydrogen or the remainder of an alcohol of the formula R.sub.1 OH by the process of copending, commonly assigned U.S. patent application No. 153,338 filed May 27, 1980.Type: GrantFiled: March 23, 1981Date of Patent: May 3, 1983Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
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Patent number: 4381297Abstract: Compounds of the formula ##STR1## wherein X is an imino acid or ester are disclosed as useful hypotensive agents due to their angiotensin converting enzyme inhibition activity.Type: GrantFiled: May 4, 1981Date of Patent: April 26, 1983Assignee: E. R. Squibb & Sons, Inc.Inventors: Donald S. Karanewsky, Edward W. Petrillo, Jr.
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Patent number: 4377709Abstract: 5-Oxoalkanoic acids are prepared by addition of a ketone containing at least one hydrogen atom in the .alpha.-position with regard to the keto group, to an .alpha.,.beta.-unsaturated acid. As catalysts secondary amines are present.Type: GrantFiled: December 19, 1980Date of Patent: March 22, 1983Assignee: Hoechst AktiengesellschaftInventor: Werner H. Muller
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Patent number: 4366076Abstract: Corrosion-inhibited compositions are described comprising a functional fluid in contact with a ferrous metal and, as corrosion inhibitor, a compound having the formula: ##STR1## wherein X is H, an alkali- or alkaline earth metal, NH.sub.4, the residue of a protonated amine, or the group --OX is the residue of an alkanol having from 1 to 20 carbon atoms or of di-, tri- or tetra-ol having from 2 to 12 carbon atoms; R.sup.1, R.sup.2 and R.sup.4 are the same or different and each is H or --CH.sub.2 CH.sub.2 COOX wherein X has its previous meaning; R.sup.3 and R.sup.5 are the same or different and each is H, --CH.sub.2 CH.sub.2 COOX wherein X has its previous meaning, or R.sup.3 or R.sup.5 is a straight- or branched chain alkyl group having from 3 to 16 carbon atoms; or R.sup.3 and R.sup.5, together with the carbon atom to which they are each attached, may form a cycloalkanone ring containing from 5 to 15 carbon atoms.Type: GrantFiled: May 28, 1981Date of Patent: December 28, 1982Assignee: Ciba-Geigy CorporationInventor: David R. Clark
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Patent number: 4357282Abstract: Fluorinated carbonyl compounds are prepared by contacting a fluorinated methyl or ethyl ether containing at least one methoxylated carbon atom-containing group selected from: --CF.sub.2 OR.sup.3, .dbd.CFOR.sup.3, ##STR1## wherein R.sup.3 is CH.sub.3 or C.sub.2 H.sub.5, with a catalyst selected from:SbX.sub.5, TaX.sub.5, NbX.sub.5, AsX.sub.5, BiX.sub.5, TiX.sub.4, ZrX.sub.4, HfX.sub.4, FeX.sub.3,mixtures of SbX.sub.3 and SbX.sub.5, ZM'X'.sub.6, and mixtures of ZM'X'.sub.6 and M'X.sub.5 where X, independently, is F, Cl, Br or I, X' is F or Cl; and Z is H, NO, O.sub.2, alkali metal or NY.sub.4 where Y, independently, is H or alkyl of 1 to 6 carbon atoms, and M' is Sb or As at a temperature of -20.degree. to 200.degree. C.Type: GrantFiled: April 3, 1981Date of Patent: November 2, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventors: Daniel G. Anderson, David C. England, Alwin S. Milian, Jr.
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Patent number: 4342694Abstract: Processes for producing a (1.alpha., 4.alpha., 5.alpha.)-6,6-dimethyl-4-halo-substituted-methyl-3-oxabicyclo[3.1.0]hexan- 2-one and its novel intermediates from known and inexpensive starting materials are described and exemplified. The halomethyl bicyclic lactone is a useful intermediate for the preparation of insecticidal cis-3-(2,2-dihaloethenyl)-2,2-dimethylcyclopropanecarboxylates or cis-3-(2-halo-2-trihalomethylethenyl)-2,2-dimethylcyclopropanecarboxylates .Type: GrantFiled: June 23, 1980Date of Patent: August 3, 1982Assignee: FMC CorporationInventors: Kiyoshi Kondo, Toshiyuki Takashima, Minoru Suda
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Patent number: 4340753Abstract: A method is provided for oxidatively cleaving .alpha.,.beta.-unsaturated cyclic ketones, such as isophorone, with an oxidizing agent, for example, ozone, and thereafter recovering the resulting keto acid. In instances where ozone is used, an aqueous hydroperoxide and phase transfer catalyst can be used to recover the keto acid. Dione cyclics, for example, dimedone, can be obtained by direct dehydration of the keto acid.Type: GrantFiled: September 2, 1980Date of Patent: July 20, 1982Assignee: General Electric CompanyInventor: James A. Cella
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Patent number: 4340748Abstract: The invention relates to a process for the manufacture of glyoxylic acid esters by catalytic dehydrogenation of glycolic acid esters in the gaseous phase.Type: GrantFiled: February 6, 1980Date of Patent: July 20, 1982Assignee: Hoechst AktiengesellschaftInventors: Herbert Baltes, Ernst I. Leupold, Friedrich Wunder
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Patent number: 4337350Abstract: The novel stereoselective and regioselective alkali metal borohydride reduction of 2,5-diketogluconic acid, alkyl esters or salts thereof to form 2-ketogulonic acid together with lesser amounts of 2-ketogluconic acid is disclosed. The 2-ketogulonic acid is readily converted to ascorbic acid.Type: GrantFiled: April 25, 1980Date of Patent: June 29, 1982Assignee: Pfizer Inc.Inventor: Glenn C. Andrews
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Patent number: 4335255Abstract: Ketoester of the formula ##STR1## .alpha.-carboxylate-.omega.-acyl fluoride of the formula ##STR2## vinyl ether of the formula ##STR3## divinyl ether of the formula ##STR4## allyl ether of the formula ##STR5## and film-forming copolymers, useful as molding resins, of the vinyl ether and/or the divinyl ether or the allyl ether and a fluorinated vinyl monomer, for example, tetrafluoroethylene, wherein, in the above formulas, n is 0 to 6, p is 0 to 7, X is CO.sub.2 M, CO.sub.2 R, CO.sub.2 H, CONH.sub.2, COF, COCl or CN, M is alkali metal, ammonium or quaternary ammonium and R is C.sub.1-8 alkyl, selected copolymers, after hydrolysis, being water-wettable and dyeable, exhibiting ion-exchange properties and being useful in curable fluoroelastomer compositions and, in film form, as the membrane in a chloroalkali electrolysis cell.Type: GrantFiled: April 3, 1980Date of Patent: June 15, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventor: Carl G. Krespan
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Patent number: 4334087Abstract: A novel process for the manufacture of .alpha.-ketocarboxylic acids which comprises the reaction of oximinohalide with cyanide ion to form oximinonitrile which is reacted with hydroxide ion to form oximinoacid and hydrolysis thereof to the .alpha.-ketoacid.Type: GrantFiled: September 11, 1980Date of Patent: June 8, 1982Assignee: Zoecon CorporationInventors: Ted A. Baer, Jeffrey N. Labovitz
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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: 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: 4323507Abstract: .alpha.-substituted derivatives of valproic acid are provided for conjugation to antigenic compositions, particularly poly(amino acids), and enzymes. The antigenic conjugates are employed for the production of antibodies, which find particular use in immunoassays for the determination of valproate, while the enzyme conjugate finds use in a homogeneous enzyme immunoassay for the determination of valproate. The compounds are synthesized by alkylating valproate at the tertiary carbon atom by an aliphatic chain with a terminal double bond which is cleaved to provide an acid or aldehyde group.Type: GrantFiled: July 14, 1980Date of Patent: April 6, 1982Assignee: Syva CompanyInventors: Danton K. Leung, Prithipal Singh
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Patent number: 4302402Abstract: A novel process for the manufacture of oximinonitriles which comprises the reaction of an oximinohalide with cyanide ion.Type: GrantFiled: September 11, 1980Date of Patent: November 24, 1981Assignee: Zoecon CorporationInventor: Jeffrey N. Labovitz
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Patent number: 4301186Abstract: This invention relates to new ammonium salts of .alpha.-ketocarboxylic acids, to their use for the production of amines in situ by photochemical decomposition and to photochemically hardenable coating compositions containing these ammonium salts.Type: GrantFiled: June 28, 1979Date of Patent: November 17, 1981Assignee: Bayer AktiengesellschaftInventors: Wolfram Mayer, Hans Rudolph, Eckhard De Cleur, Manfred Schonfelder