Aldehyde Or Ketone Patents (Class 562/577)
  • Patent number: 4902828
    Abstract: 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: Grant
    Filed: October 18, 1984
    Date of Patent: February 20, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Wickenhaeuser, Bernd Heida, Fritz Graf, Leopold Hupfer
  • Patent number: 4898974
    Abstract: 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: Grant
    Filed: April 23, 1985
    Date of Patent: February 6, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karlfried Dickore, Hans D. Engels, Hans Kratzer, Walter Merz
  • Patent number: 4867849
    Abstract: 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: Grant
    Filed: July 25, 1988
    Date of Patent: September 19, 1989
    Inventors: Dario R. Cova, John M. Thorman
  • Patent number: 4827004
    Abstract: 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: Grant
    Filed: August 24, 1987
    Date of Patent: May 2, 1989
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Albert Fischli, Max Schmid, Rudolf Schmid
  • Patent number: 4758594
    Abstract: 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: Grant
    Filed: May 19, 1986
    Date of Patent: July 19, 1988
    Assignee: Schering Corporation
    Inventors: Anil K. Saksena, Jesse K. Wong, Pietro Mangiaracina
  • Patent number: 4738802
    Abstract: 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: Grant
    Filed: November 16, 1983
    Date of Patent: April 19, 1988
    Assignee: Ethyl Corporation
    Inventor: John Y. Lee
  • Patent number: 4705867
    Abstract: 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: Grant
    Filed: April 4, 1986
    Date of Patent: November 10, 1987
    Assignee: Degussa Aktiengesellschaft
    Inventors: Guenes Giray, Klaus Huthmacher, Axel Kleemann, Thomas Lied
  • Patent number: 4649217
    Abstract: 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: Grant
    Filed: March 15, 1983
    Date of Patent: March 10, 1987
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Takao Maki, Kenji Murayama, Yoshio Asahi
  • Patent number: 4647413
    Abstract: 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: Grant
    Filed: January 20, 1984
    Date of Patent: March 3, 1987
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Patricia M. Savu
  • Patent number: 4643994
    Abstract: 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: Grant
    Filed: December 17, 1984
    Date of Patent: February 17, 1987
    Assignee: The Research Foundation of State University of New York
    Inventors: Eric Block, Saleem Ahmad
  • Patent number: 4628117
    Abstract: 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: Grant
    Filed: February 4, 1985
    Date of Patent: December 9, 1986
    Assignee: National Distillers and Chemical Corporation
    Inventor: Hubert J. Sharkey
  • Patent number: 4628118
    Abstract: 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: Grant
    Filed: October 10, 1985
    Date of Patent: December 9, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventor: Dieter Arlt
  • Patent number: 4620034
    Abstract: 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: Grant
    Filed: January 22, 1985
    Date of Patent: October 28, 1986
    Assignee: Akzo NV
    Inventor: Peter C. C. Smits
  • Patent number: 4614816
    Abstract: 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: Grant
    Filed: October 13, 1983
    Date of Patent: September 30, 1986
    Assignee: BP Chemicals Limited
    Inventors: David J. Drury, Peter S. Williams
  • Patent number: 4614822
    Abstract: 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: Grant
    Filed: August 26, 1980
    Date of Patent: September 30, 1986
    Assignee: Mobay Chemical Corporation
    Inventor: Dennis E. Jackman
  • Patent number: 4612391
    Abstract: 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: Grant
    Filed: September 22, 1980
    Date of Patent: September 16, 1986
    Assignee: Philip Morris Incorporated
    Inventor: William B. Edwards, III
  • Patent number: 4599446
    Abstract: 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: Grant
    Filed: April 17, 1985
    Date of Patent: July 8, 1986
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventor: Tadamitsu Kiyoura
  • Patent number: 4567004
    Abstract: 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: Grant
    Filed: July 18, 1984
    Date of Patent: January 28, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz U. Blank, Erich Wolters
  • Patent number: 4564704
    Abstract: 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: Grant
    Filed: January 22, 1981
    Date of Patent: January 14, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karlfried Dickore, Hans D. Engels, Hans Kratzer, Walter Merz
  • Patent number: 4558153
    Abstract: 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: Grant
    Filed: October 23, 1984
    Date of Patent: December 10, 1985
    Assignee: BP Chemicals Limited
    Inventor: John Cook
  • Patent number: 4556732
    Abstract: 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: Grant
    Filed: May 27, 1980
    Date of Patent: December 3, 1985
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
  • Patent number: 4529704
    Abstract: 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: Grant
    Filed: November 25, 1981
    Date of Patent: July 16, 1985
    Assignee: Miles Laboratories, Inc.
    Inventors: Robert W. Trimmer, William I. White
  • Patent number: 4511734
    Abstract: 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: Grant
    Filed: May 5, 1982
    Date of Patent: April 16, 1985
    Assignee: Lonza Ltd.
    Inventors: Pavel Lehky, Peter Hardt
  • Patent number: 4503246
    Abstract: 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: Grant
    Filed: December 1, 1981
    Date of Patent: March 5, 1985
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Tadayuki Mitani, Mamoru Endo
  • Patent number: 4500720
    Abstract: 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: Grant
    Filed: January 19, 1984
    Date of Patent: February 19, 1985
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
  • Patent number: 4487957
    Abstract: 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: Grant
    Filed: April 21, 1983
    Date of Patent: December 11, 1984
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
  • Patent number: 4487972
    Abstract: 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: Grant
    Filed: April 22, 1980
    Date of Patent: December 11, 1984
    Assignee: Mobil Oil Corporation
    Inventors: Werner O. Haag, Darrell D. Whitehurst
  • Patent number: 4465863
    Abstract: 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: Grant
    Filed: November 12, 1982
    Date of Patent: August 14, 1984
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Steven D. Temes, Theodore J. Tyszkiewicz, Marie R. Hanna
  • Patent number: 4442303
    Abstract: 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: Grant
    Filed: December 9, 1980
    Date of Patent: April 10, 1984
    Assignee: El Paso Products Company
    Inventor: Samuel S. Mims
  • Patent number: 4440740
    Abstract: 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: Grant
    Filed: April 26, 1982
    Date of Patent: April 3, 1984
    Assignee: Merck & Co., Inc.
    Inventors: Joseph A. Fix, Stefano A. Pogany
  • Patent number: 4414418
    Abstract: 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: Grant
    Filed: May 19, 1982
    Date of Patent: November 8, 1983
    Assignee: Lonza Ltd.
    Inventor: Pavel Lehky
  • Patent number: 4390724
    Abstract: 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: Grant
    Filed: April 16, 1982
    Date of Patent: June 28, 1983
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
  • Patent number: 4390702
    Abstract: 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: Grant
    Filed: December 29, 1980
    Date of Patent: June 28, 1983
    Assignees: Daikan Kogyo Co., Ltd., Shionogi and Co., Ltd.
    Inventors: Susumu Misaki, Masahiro Suefuji, Tadahiko Tsushima, Hiroshi Tanida
  • Patent number: 4387245
    Abstract: 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: Grant
    Filed: May 20, 1981
    Date of Patent: June 7, 1983
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Rolf Wittmann, Willi Wintermeyer, Jurgen Butzke
  • Patent number: 4382037
    Abstract: 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: Grant
    Filed: March 23, 1981
    Date of Patent: May 3, 1983
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
  • Patent number: 4381297
    Abstract: 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: Grant
    Filed: May 4, 1981
    Date of Patent: April 26, 1983
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Donald S. Karanewsky, Edward W. Petrillo, Jr.
  • Patent number: 4377709
    Abstract: 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: Grant
    Filed: December 19, 1980
    Date of Patent: March 22, 1983
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Werner H. Muller
  • Patent number: 4366076
    Abstract: 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: Grant
    Filed: May 28, 1981
    Date of Patent: December 28, 1982
    Assignee: Ciba-Geigy Corporation
    Inventor: David R. Clark
  • Patent number: 4357282
    Abstract: 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: Grant
    Filed: April 3, 1981
    Date of Patent: November 2, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Daniel G. Anderson, David C. England, Alwin S. Milian, Jr.
  • Patent number: 4342694
    Abstract: 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: Grant
    Filed: June 23, 1980
    Date of Patent: August 3, 1982
    Assignee: FMC Corporation
    Inventors: Kiyoshi Kondo, Toshiyuki Takashima, Minoru Suda
  • Patent number: 4340753
    Abstract: 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: Grant
    Filed: September 2, 1980
    Date of Patent: July 20, 1982
    Assignee: General Electric Company
    Inventor: James A. Cella
  • Patent number: 4340748
    Abstract: 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: Grant
    Filed: February 6, 1980
    Date of Patent: July 20, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Herbert Baltes, Ernst I. Leupold, Friedrich Wunder
  • Patent number: 4337350
    Abstract: 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: Grant
    Filed: April 25, 1980
    Date of Patent: June 29, 1982
    Assignee: Pfizer Inc.
    Inventor: Glenn C. Andrews
  • Patent number: 4335255
    Abstract: 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: Grant
    Filed: April 3, 1980
    Date of Patent: June 15, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Carl G. Krespan
  • Patent number: 4334087
    Abstract: 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: Grant
    Filed: September 11, 1980
    Date of Patent: June 8, 1982
    Assignee: Zoecon Corporation
    Inventors: Ted A. Baer, Jeffrey N. Labovitz
  • Patent number: 4334094
    Abstract: 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: Grant
    Filed: June 30, 1980
    Date of Patent: June 8, 1982
    Assignee: Texaco Inc.
    Inventor: John F. Knifton
  • Patent number: 4323702
    Abstract: 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: Grant
    Filed: November 17, 1980
    Date of Patent: April 6, 1982
    Assignee: Koei Chemical Co., Ltd.
    Inventors: Nariyoshi Kawabata, Shinichi Yasuda, Takeshi Yamazaki
  • Patent number: 4323507
    Abstract: .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: Grant
    Filed: July 14, 1980
    Date of Patent: April 6, 1982
    Assignee: Syva Company
    Inventors: Danton K. Leung, Prithipal Singh
  • Patent number: 4302402
    Abstract: A novel process for the manufacture of oximinonitriles which comprises the reaction of an oximinohalide with cyanide ion.
    Type: Grant
    Filed: September 11, 1980
    Date of Patent: November 24, 1981
    Assignee: Zoecon Corporation
    Inventor: Jeffrey N. Labovitz
  • Patent number: 4301186
    Abstract: 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: Grant
    Filed: June 28, 1979
    Date of Patent: November 17, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfram Mayer, Hans Rudolph, Eckhard De Cleur, Manfred Schonfelder