Alicyclic Acids Having An Oxy, Aldehyde, Or Ketone Group Patents (Class 562/508)
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Patent number: 4331608Abstract: Unsaturated compounds having at least 4 carbon atoms, including unsaturated alicyclic compounds having at least 4 carbon atoms, unsaturated aliphatic compounds having at least one carbon-carbon unsaturated bond and having at least 4 carbon atoms and unsaturated aromatic compounds having at least one carbon-carbon unsaturated bond in the branched chain thereof and (ii) aldehydes or ketones having at least 4 carbon atoms are catalytically co-oxidized with an oxygen-containing gas in a liquid phase to form a cleaveged product or products of unsaturated bond of the unsaturated compounds at a high yield. This co-oxidation reaction is carried out in the presence of a heavy metal containing iron, cobalt, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum, copper, silver, chromium, molybdenum, tungsten, manganese and rhenium and the compounds thereof.Type: GrantFiled: June 2, 1980Date of Patent: May 25, 1982Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Keiji Kawamoto, Toshihiro Yoshioka
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Patent number: 4310709Abstract: The process for the manufacture of but-2-en-1-ol compounds by isomerizing but-3-en-1-ol compounds in the presence of a palladium catalyst and of hydrogen is improved by modifying the palladium catalyst with selenium or tellurium.The but-2-en-1-ols manufactured according to the invention are either solvents or valuable starting materials for the manufacture of solvents, dyes, surface coatings, paints and pesticides.Type: GrantFiled: April 23, 1980Date of Patent: January 12, 1982Assignee: BASF AktiengesellschaftInventor: Walter Rebafka
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Patent number: 4286068Abstract: A process for oxidizing organic substrates such as ketones and ethylenically unsaturated compounds. The substrate is contacted with aqueous hydrogen peroxide in a solution or in a two-phase liquid system, in the presence of a polymeric catalyst containing chemically bonded arsenic. This process can lead to lactones or hydroxy acids from cyclic ketones or to esters or mixtures of alcohol and carboxylic acid from open chain ketones. Unsaturated compounds afford epoxides and/or diols. Preparations of certain polymers substituted by arsenic groups, particularly from polystyrene, poly(vinylpyridine) and copolymers thereof, useful as catalysts in such oxidation process, are described. For example, polystyrene is brominated, bromine therein is replaced by lithium and the resulting lithiated polymer is converted into a polymer containing an arsenic group, such as arsono, --As(O)(OH).sub.2, as substituent group, by reaction with arsine triethoxide followed by oxidation and hydrolysis by aqueous hydrogen peroxide.Type: GrantFiled: April 28, 1980Date of Patent: August 25, 1981Assignee: Allied Chemical CorporationInventors: Frank Mares, Stephen E. Jacobson
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Patent number: 4283420Abstract: The chemical compounds of the invention are useful as the active compound in drugs because of their anticonvulsant and/or antianoxic activity. They have the general formula ##STR1## wherein Z is a hydroxyl group; a group--OM wherein M is an alkali metal atom or an equivalent atom fraction of an alkaline-earth metal or an amino group such as --NH.sub.2, and R is a linear or branched alkyl group containing from 1 to 9 carbon atoms, and optionally substituted by one or more halogen atoms; a linear or branched alkenyl or alkynyl, alkoxyalkyl, or acylalkyl group containing from 2 to 9 carbon atoms and optionally substituted by one or more halogen atoms; an aryl or arylalkyl or aryloxyalkyl group comprising at least one aromatic radical and an alkyl chain having from 1 to 4 carbon atoms.Type: GrantFiled: April 18, 1979Date of Patent: August 11, 1981Assignee: LabazInventors: Charles Pigerol, Jean-Claude Vernieres, Pierre Eymard, Jacques Simiand, Madeleine Broll, Jean-Yves Lacolle
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Patent number: 4267362Abstract: A process is described for the preparation of delta keto-acids wherein there is used as a catalyst the condensation adduct of a cyclic secondary amine with an .alpha.-.beta.-acrylic-type unsaturated compound, providing high selectivity and conversion results.Type: GrantFiled: August 17, 1979Date of Patent: May 12, 1981Assignee: Stamicarbon, B.V.Inventors: Peter J. N. Meyer, Josef M. Penders
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Patent number: 4259512Abstract: Preparation of 5,5-Dimethyl-8-carboalkoxybicyclo [4.3.0]non-1-(6)-ene-2,7-dione by condensing dimethylpyruvic acid and 5-ono-6-heptenoic acid to produce a dibasic acid. Esterification of the acid produces a diester which is cyclized to produce the compound.Type: GrantFiled: October 15, 1976Date of Patent: March 31, 1981Assignee: State Board of Higher Education for and on Behalf of the University of OregonInventor: Lloyd J. Dolby
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Patent number: 4259250Abstract: The present invention provides novel thromboxane analogs and intermediates. Particularly, the present invention provides novel 11a-homo-PG intermediates for preparing 11a-methano TXA.sub.2 compounds.Type: GrantFiled: January 28, 1980Date of Patent: March 31, 1981Assignee: The Upjohn CompanyInventor: Gordon L. Bundy
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Patent number: 4249015Abstract: Carboxylic acids and/or esters are prepared by converting the ##STR1## moiety in a 1-substituted 2,2-trihaloethanol, or derivative wherein X represents halogen and R is hydrogen or an acyl group to an organic acid and/or ester grouping of the formula ##STR2## wherein R' is hydrogen or alkyl of 1 to 6 carbon atoms, in the process which comprises reacting the 1-substituted 2,2,2-trihaloethanol or acylated derivative with molecular oxygen in the presence of a catalyst comprising a complex of a transition metal having an atomic number from 21-30, 39-48 or 57-80 and at least one molecule of a ligand containing trivalent nitrogen, phosphorus, arsenic or antimony. This reaction is carried out in a reaction medium comprising an alcohol or aqueous alcohol having 1 to 6 carbon atoms optionally containing an alkali metal, said alcoholic solvent also serving as a reactant source when carboxylic acid esters are formed.Type: GrantFiled: January 26, 1979Date of Patent: February 3, 1981Assignee: Shell Oil CompanyInventors: John A. Schofield, John E. Hawes
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Patent number: 4234739Abstract: Glyoxylic acids or derivatives thereof are prepared by reacting an acyl nitrile compound with concentrated sulfuric acid in the presence of halide anion to form a first reaction product and then further reacting the first reaction product with a compound of the general formula ROH to form the desired glyoxylic acid or glyoxylic acid derivative.Type: GrantFiled: December 5, 1978Date of Patent: November 18, 1980Assignee: Stauffer Chemical CompanyInventors: James M. Photis, Fred S. Eiseman, Sidney M. Gister
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Patent number: 4218378Abstract: The present invention provides novel 11a-methano-TXA compounds and intermediates and processs for their preparation. Further provided are methods for using these novel TXA analogs as inhibitors of thromboxane synthetase, rendering these analogs useful for a variety of pharmacological purposes. These pharmacological uses include anti-inflammatory, anti-thromobitc, and anti-asthma indications.Type: GrantFiled: May 1, 1979Date of Patent: August 19, 1980Assignee: The Upjohn CompanyInventor: Gordon L. Bundy
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Patent number: 4217290Abstract: This invention consists of a process for preparing bifunctional aliphatic organic compounds of at least 6 carbon atoms, wherein a cycloaliphatic oxyhydroperoxide is reacted with an alpha-olefine having its double bond activated by a conjugate electron-attracting group, in the presence of a bivalent Cr salt, a bivalent V salt or a trivalent Ti salt.Type: GrantFiled: June 20, 1979Date of Patent: August 12, 1980Assignee: Brichima S.p.A.Inventors: Paolo Maggioni, Francesco Mauri, Attilio Citterio
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Patent number: 4209642Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO, --C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.Type: GrantFiled: March 15, 1979Date of Patent: June 24, 1980Assignee: Shell Oil CompanyInventor: Steven A. Roman
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Patent number: 4196303Abstract: The compound d-isomenthoxyacetic acid and various ester and amide derivatives are useful resolving agents and perfume ingredients.Type: GrantFiled: March 20, 1978Date of Patent: April 1, 1980Assignee: SCM CorporationInventors: Bernard J. Kane, Sean G. Traynor
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Patent number: 4194053Abstract: A diester of .alpha.-acetyl-.alpha.'-methyl succinic acid is prepared in improved yield under substantially anhydrous process conditions which minimizes decomposition of that diester by reacting an acetoacetate ester with an .alpha.-halopropionate ester in a solvent containing a nonpolar, aprotic liquid at from about 50.degree. C. to reflux temperature in the presence of a phase transfer agent, a catalytic amount of iodide ion and solid form, substantially anhydrous alkali metal base or basic salt having a high surface area (a size of about 60 mesh or smaller). The resulting diesters can also be used under the stabilizing reaction mixture conditions of this invention as intermediates in processes for making ibuprofen by combining and reacting the .alpha.-acetyl-.alpha.'-methylsuccinate diester with vinyl isobutyl ketone, (or the corresponding Mannich base plus an alkylating agent) and an alkali metal base for a time sufficient to form a reaction mixture containing the .alpha.-methyl-.alpha.'-acetyl-.alpha.Type: GrantFiled: September 1, 1978Date of Patent: March 18, 1980Assignee: The Upjohn CompanyInventor: David R. White
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Patent number: 4189604Abstract: Bestatin, which is [(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]-L-leucine, and related compounds which inhibit aminopeptidase B, leucino aminopeptidase and Bleomycin hydrolase, enhance the anti-tumor effect of Bleomycin and exhibit an antifertility effect were synthesized and tested.Type: GrantFiled: June 24, 1977Date of Patent: February 19, 1980Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Hamao Umezawa, Takaaki Aoyagi, Tomohisa Takita, Rinzo Nishizawa, Tetsushi Saino
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Patent number: 4189596Abstract: 2-Aryl-C.sub.2 to C.sub.5 -alkanoic acids and esters thereof are prepared by heating a 2-(2-oxo-3-cyclohexenyl)-alkanoic acid or ester derivative in the presence of a sulfonic acid or a phosphonic acid at 75.degree. C. to 130.degree. C. while providing a means for removing water from the reaction mixture. In the process new butenolide derivative intermediates have been discovered. Alternatively, the 2-aryl-C.sub.2 to C.sub.6 -alkanoic acids can be prepared from the butenolides by forming a mixture of the 2-(2-oxo-3-cyclohexenyl)-alkanoic acid with acetic anhydride in the presence of an acid scavenging base, allowing the mixture to stand for a time sufficient to form an acetate intermediate, heating the resulting mixture to about 75.degree. C. to about 130.degree. C. to form the betenolide intermediates. Thereafter these intermediates can be heated with sulfonic or phosphonic acid as above while removing water to form the 2-aryl-C.sub.2 to C.sub.Type: GrantFiled: May 2, 1977Date of Patent: February 19, 1980Assignee: The Upjohn CompanyInventor: Verlan H. VanRheenen
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Patent number: 4182684Abstract: A machine dishwashing composition is provided which comprises the following: (a) from 5 to 90 percent by weight of a compound corresponding to the formula ##STR1## wherein M is alkali metal or ammonium and wherein n is a number from 1 through 3, and wherein R is selected from an alkyl radical having from 1 to 20 carbon atoms, an alkenyl radical having from 1 to 20 carbon atoms, an alkynyl radical having from 1 to 20 carbon atoms, a cycloalkane radical having from 3 to 20 carbon atoms, an alkanol radical having from 2 to 20 carbon atoms, an ether radical having at least 3 carbon atoms, an aryl radical having at least 6 carbon atoms, a substituted aryl radical having at least 6 carbon atoms wherein the substituents are halogen, nitro, amide or carboxyalkyl substituents, aralkyl radicals having at least 7 carbon atoms and arylether radicals having at least 7 carbon atoms, and (b) from 0 to 5 percent by weight of a low-foaming anionic or nonionic surfactant, (c) a chlorine-providing material in an amount sufficieType: GrantFiled: November 17, 1978Date of Patent: January 8, 1980Assignee: Monsanto CompanyInventor: Kent P. Lannert
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Patent number: 4172954Abstract: Organic compounds having a substituent represented by the formula ##STR1## wherein M is alkali metal or ammonium are useful complexing agents for metal and/or alkaline earth metal ions.Type: GrantFiled: September 2, 1977Date of Patent: October 30, 1979Assignee: Monsanto CompanyInventor: Kent P. Lannert
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Patent number: 4154962Abstract: A new process by which cyclohexanone is treated, in the presence of a suitable acid or a salt of an organic base, with pyruvic acid or with one of its simple derivatives (ester or salt) to give hydratropic acid.Type: GrantFiled: November 1, 1977Date of Patent: May 15, 1979Assignee: Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.p.A.Inventor: Leandro Baiocchi
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Patent number: 4152456Abstract: Tropone derivatives substituted with an amino-, thio- or oxy-derivative of oxalic acid or acetic acid are disclosed. In addition, the tropone nucleus can be optionally further substituted. The foregoing compounds are useful for preventing or treating allergic conditions in a mammal. Methods for the preparation and use of the compounds are disclosed.Type: GrantFiled: October 7, 1977Date of Patent: May 1, 1979Assignee: Ayerst, McKenna and Harrison LimitedInventors: Jehan F. Bagli, Tibor Bogri
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Patent number: 4139717Abstract: 1,3-Dicarbonyl compounds useful as medicines, agricultural chemicals, perfumes, and their intermediates are prepared by reacting a specific .alpha.,.beta.-unsaturated carbonyl compound with a specific organic copper lithium compound in the presence of an aprotic inert organic solvent, and then reacting the reaction product with an organic carboxylic acid halide or anhydride. In particular, novel 2-acyl-3-substituted cyclopentan-1-ones and 2-acyl-3-substituted cyclohexan-1-ones having important physiological activities are provided.Type: GrantFiled: January 4, 1977Date of Patent: February 13, 1979Assignee: Teijin LimitedInventors: Seizi Kurozumi, Takeshi Toru, Toshio Tanaka, Shuzi Miura, Makiko Kobayashi, Sachio Ishimoto
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Patent number: 4118420Abstract: Organic compounds having a substituent represented by the formula ##STR1## wherein M is alkali metal or ammonium are useful complexing agents for metal and/or alkaline earth metal ions.Type: GrantFiled: March 25, 1976Date of Patent: October 3, 1978Assignee: Monsanto CompanyInventor: Kent P. Lannert
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Patent number: 4116987Abstract: A process for the production of alcohols and esters comprises hydroxylating a saturated hydrocarbon at between about 20.degree. and about 130.degree. C. with an oxygenated amine. The amine may be a hydroxylated secondary amine or an oxide of a tertiary amine. The reaction medium includes a Lewis acid and a salt of divalent or trivalent iron.Type: GrantFiled: March 21, 1977Date of Patent: September 26, 1978Assignee: Fats and Proteins Research Foundation, Inc.Inventor: Norman C. Deno