Cyclic Alcohol Moiety Patents (Class 560/193)
  • Patent number: 4283414
    Abstract: The invention concerns novel pesticidal esters of the pyrethrin or pyrethroid type in which the methylene group bonded to the ester carbonyl and/or ester oxygen bears a fluorine substituent. The compounds of the invention are active against insect pests including flies, moths, aphids and beetles and acarina pests including ticks.
    Type: Grant
    Filed: June 8, 1979
    Date of Patent: August 11, 1981
    Assignee: ICI Australia Limited
    Inventors: Donald W. G. Harney, Peter G. Lehman, Joseph C. Rundle
  • Patent number: 4266046
    Abstract: Cyclic carbonate esters are reacted with polycarboxylic acids to produce bis(hydroxyalkyl) esters from aromatic polycarboxylic acids in the presence of selected catalysts comprising at least one of phosphines, phosphonium halides, sulfonium halides, sulfoxonium halides, and ammonium and alkyl ammonium halides. In the preferred embodiment, ethylene carbonate is reacted with terephthalic acid to produce bis(2-hydroxyethyl) terephthalate and/or polymers thereof.
    Type: Grant
    Filed: September 17, 1976
    Date of Patent: May 5, 1981
    Assignee: Phillips Petroleum Company
    Inventor: Yulin Wu
  • Patent number: 4261912
    Abstract: This invention describes novel antioxidant compounds which are esters of .omega.,.omega.-bis(dialkylhydroxyphenyl) alkanols having the formula: ##STR1## wherein R.sub.1 is a tertiary alkyl group having 4-8 carbon atoms;R.sub.2 is alkyl having 1-4 carbon atoms;R.sub.3 is a straight chain or branched alkylene group having 1-4 carbon atoms;x is 1-4,n is 1 or 2, and,Y is a group of the formulas ##STR2## when n is 1, where R.sub.4 is alkyl having from 12 to 24 carbon atoms, phenyl, or phenyl substituted with hydroxy of alkyl having 1 to 4 carbon atoms, or combinations thereof, or ##STR3## when n is 2, where R.sub.5 is a direct bond, a straight chain or branched alkylene having 1 to 8 carbon atoms, or a phenylene group, and m is 0 to 4.
    Type: Grant
    Filed: August 1, 1979
    Date of Patent: April 14, 1981
    Assignee: GAF Corporation
    Inventor: David J. Tracy
  • Patent number: 4260810
    Abstract: A process for preparing a diester of a dicarboxylic acid having two more carbon atoms than the unsaturated hydrocarbon used as a starting material, which comprises subjecting an unsaturated hydrocarbon, carbon monoxide and an ester of nitrous acid to catalytic vapor phase reaction at a temperature of 50.degree. to 200.degree. C. in the presence of a platinum group metal or a salt thereof and a halogen compound.
    Type: Grant
    Filed: June 27, 1979
    Date of Patent: April 7, 1981
    Assignee: Ube Industries, Ltd.
    Inventors: Sumio Umemura, Kanenobu Matsui, Yoshinari Ikeda, Katsuro Masunaga, Takumi Kadota, Kozo Fujii, Keigo Nishihira, Masaoki Matsuda
  • Patent number: 4259519
    Abstract: Conjugated diolefins (e.g., 1,3-butadiene) are carbonylated by the palladium-catalyzed addition of carbon monoxide and an alcohol of the formula ROH (e.g., benzyl alcohol) whereby polycarboxylic esters are formed in which the pair of double bonds of the conjugated diolefin has been transformed into a moiety having the formula: ##STR1## In the process, the olefin, carbon monoxide, and alcohol are reacted in the presence of a palladium(II) salt, a copper(II) salt, and a base, at certain concentrations and at a pressure and temperature sufficient to effect the carbonylation. The resulting unsaturated diester can be hydrolyzed and hydrogenated or vice versa to obtain the corresponding linear diacid (e.g., adipic acid).
    Type: Grant
    Filed: July 19, 1978
    Date of Patent: March 31, 1981
    Assignee: Polymer Sciences Corporation
    Inventor: John K. Stille
  • Patent number: 4252738
    Abstract: 1,2-Halohydrincarboxylic acid esters of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are identical or different and represent hydrogen, cyano and optionally substituted alkyl, alkenyl, aralkyl, aryl, alkoxycarbonyl, acyloxy, alkoxy and aryloxy, and furthermoreR.sup.1 and R.sup.2 and/or R.sup.3 and R.sup.4, or R.sup.1 and R.sup.3 and/or R.sup.2 and R.sup.4 can be linked, forming a ring with the carbon atoms to which they are bonded;R.sup.5 represents hydrogen and optionally substituted alkyl, alkenyl, aralkyl, aryl, alkoxy and alkoxycarbonyl andX represents fluorine, chlorine, bromine and iodine; a process for preparing such 1,2-halohydrincarboxylic acid esters by reacting a cyclobutane-cis-1,2-diol of the formula ##STR2## with an orthoester of the formula ##STR3## wherein R.sup.1 -R.sup.5 have the previously ascribed significance and R.sup.6 -R.sup.
    Type: Grant
    Filed: March 17, 1978
    Date of Patent: February 24, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Willy Hartmann, Hans-Georg Heine
  • Patent number: 4252727
    Abstract: A resin for coatings, particularly useful as a medium for printing inks and paints, comprising a modified polymer produced by adding at least one .alpha.,.beta.-unsaturated dicarboxylic acid or anhydride thereof to at least one liquid conjugated diolefinic polymer having a number average molecular weight of 150 to 3,000, a viscosity of 2 to 5,000 cps at 30.degree. C. and at least 50% of cis-1,4 structure and subjecting the resulting adduct to diesterification with at least one alcohol having 1 to 27 carbon atoms and whereby the acid value owing to the carboxyl group or the carboxylic anhydride group of the resulting modified polymer being made not more than 10.
    Type: Grant
    Filed: February 5, 1976
    Date of Patent: February 24, 1981
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Seimei Yasui, Minoru Hino, Kunio Izumi, Otsugu Hayashi
  • Patent number: 4250327
    Abstract: A group of water-soluble polymeric yellow colors and their preparation is disclosed. These colors comprise a plurality of units of a chromophore of the formula ##STR1## wherein M.sup.+ is a pharmaceutically acceptable monovalent cation attached directly to amine units present in a nonchromophoric polymer backbone. In a preferred embodiment of the invention the backbone is a homopolymer or copolymer of vinylamine. These colorants find special utility as nonabsorbable colorants for edibles, especially foods and beverages, where their yellow hue is an excellent color match for existing monomeric azo food colors such as tartrazine, and as components of acid-insoluble pigment lakes which are themselves suitable for use in edibles.
    Type: Grant
    Filed: January 2, 1979
    Date of Patent: February 10, 1981
    Assignee: Dynapol
    Inventors: Daniel J. Dawson, Kenneth M. Otteson, Roman Davis
  • Patent number: 4249019
    Abstract: A carboxylic ester is produced in one step in a high yield and with a high selectivity by reacting an aldehyde with an alcohol in the presence of oxygen by using a catalyst comprising (I) palladium, (II) at least one compound selected from the group consisting of lead compounds, thallium compounds and mercury compounds and (III) at least one compound selected from the group consisting of alkali metal compounds and alkaline earth metal compounds.
    Type: Grant
    Filed: November 13, 1978
    Date of Patent: February 3, 1981
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Nobuhiro Tamura, Yohei Fukuoka, Setsuo Yamamatsu, Yoshio Suzuki, Ryoichi Mitsui, Tadayuki Ibuki
  • Patent number: 4243572
    Abstract: A plasticizer for polyvinyl butyral wherein the plasticizer is an alkyl alkylaryl adipate and particularly a benzyl alkyl adipate. The plasticized polyvinyl butyral is specially useful in the manufacture of transparent sheets and particularly as an interlayer for laminated safety glass.
    Type: Grant
    Filed: November 19, 1979
    Date of Patent: January 6, 1981
    Assignee: Saint-Gobain Industries
    Inventor: Daniel Dages
  • Patent number: 4237312
    Abstract: In the oxidation of acyclic conjugated dienes, recovery and recycle of the oxidation catalyst is accomplished by distilling off the oxidation solvent, extraction of the oxidation product with a suitable solvent, and removal of the extraction solvent residue from the catalyst, and recycle of the catalyst to the oxidation step.
    Type: Grant
    Filed: April 2, 1979
    Date of Patent: December 2, 1980
    Assignee: Phillips Petroleum Company
    Inventor: Paul R. Stapp
  • Patent number: 4234740
    Abstract: A process for preparing a diester of a dicarboxylic acid having two more carbon atoms than the unsaturated hydrocarbon used as the starting material, which comprises subjecting an unsaturated hydrocarbon, carbon monoxide and an alcohol to reaction in the presence of a platinum group metal or a salt thereof; a compound selected from the group consisting of nitric acid, a nitrogen oxide and an ester of nitrous acid; and a halogen compound.
    Type: Grant
    Filed: November 28, 1978
    Date of Patent: November 18, 1980
    Assignee: Ube Industries, Ltd.
    Inventors: Sumio Umemura, Kanenobu Matsui, Yoshinari Ikeda, Katsuro Masunaga, Takumi Kadota
  • Patent number: 4233230
    Abstract: A process for preparing esters and halides is disclosed comprising the step of reacting a cyclic olefin having the formula I ##STR1## wherein R.sub.1 and R.sub.4 are the same or different from each other and each represents hydrogen, methyl, or ethyl;R.sub.2 and R.sub.3 are the same or different from each other and each represents hydrogen or alkyl containing 1 to 5 carbon atoms; andn represents a whole number from 2 to 12, with an acyclic olefin having the formula II ##STR2## wherein R.sub.5 represents hydrogen, methyl, ethyl or the group ##STR3## wherein R.sub.12 and R.sub.13 are the same or different from each other and each represents hydrogen or alkyl containing 1 to 5 carbon atoms;Y represents halogen; an acyloxy group R.sub.14 --CO--O wherein R.sub.14 represents alkyl containing 1-12 carbon atoms, phenyl or phenyl alkyl containing 7-12 carbon atoms, or an oxycarbonyl group R.sub.15 --O--CO wherein R.sub.
    Type: Grant
    Filed: May 4, 1978
    Date of Patent: November 11, 1980
    Assignee: Rhone-Poulenc Industries
    Inventor: Jean Otton
  • Patent number: 4230881
    Abstract: A method for the preparation of organic esters of oxalic acid by reaction of carbon monoxide under pressure with the corresponding alcohol is disclosed, the improvement consisting in the use of a quite particular catalyst system. The catalyst is a binary system in which the principal member is a palladium complex and the co-catalyst is a compound, preferably an organic compound having an acidic nature, no matter how weak.
    Type: Grant
    Filed: April 6, 1978
    Date of Patent: October 28, 1980
    Assignee: Snamprogetti, S.p.A.
    Inventors: Ugo Romano, Franco Rivetti
  • Patent number: 4229587
    Abstract: A process for preparing aromatic esters by oxyacylation which comprises contacting benzene or an aryl alkyl compound with a carboxylic acid and oxygen in the vapor phase in the presence of a catalytically effective amount of a catalyst comprising an oxide of uranium and at least one oxide selected from the group consisting of arsenic, antimony and bismuth oxide.
    Type: Grant
    Filed: December 26, 1978
    Date of Patent: October 21, 1980
    Assignee: National Distillers and Chemical Corporation
    Inventor: Jawad H. Murib
  • Patent number: 4229589
    Abstract: A process for preparing a diester of oxalic acid which comprises bringing carbon monoxide into contact with an ester of nitrous acid in the liquid phase, in the presence of metallic palladium or a salt thereof, preferably with introduction of a gas containing molecular oxygen into the reaction system, more preferably with further incorporation of an alcohol in the reaction system.
    Type: Grant
    Filed: August 31, 1978
    Date of Patent: October 21, 1980
    Assignee: UBE Industries, Ltd.
    Inventors: Kenji Nishimura, Shinichiro Uchiumi, Kozo Fujii, Keigo Nishihira, Masayoshi Yamashita, Hiroshi Itatani
  • Patent number: 4229591
    Abstract: A process for preparing a diester of oxalic acid which comprises bringing carbon monoxide into contact with an ester of nitrous acid or with an alcohol and a nitrogen oxide or a hydrate of the nitrogen oxide in the gaseous phase in the presence of a solid catalyst containing metallic palladium or a salt thereof, a gas containing molecular oxygen being introduced into the reaction system in cases where said nitrogen oxide or a hydrate of the nitrogen oxide requires molecular oxygen together with the alcohol to form an ester of nitrous acid.
    Type: Grant
    Filed: August 31, 1978
    Date of Patent: October 21, 1980
    Assignee: UBE Industries, Ltd.
    Inventors: Kenji Nishimura, Kozo Fujii, Keigo Nishihira, Masaoki Matsuda, Shinichiro Uchiumi
  • Patent number: 4226808
    Abstract: Described are D-(threo)-1-p-substituted phenyl-2-dihalogeno-.alpha.-deuterioalkanoylamido-1,3-propanediols and their use as antibacterial agents.
    Type: Grant
    Filed: August 17, 1979
    Date of Patent: October 7, 1980
    Assignee: Schering Corporation
    Inventor: Tattanahalli L. Nagabhushan
  • Patent number: 4224455
    Abstract: New reactive surfactants or emulsifiers useful in a broad range of emulsion polymerization processes are provided, along with processes for making and using such. The reactive surfactants are comprised of ring sulfonated half esters of maleic anhydride with alkoxylated alkyl arylols.
    Type: Grant
    Filed: November 13, 1978
    Date of Patent: September 23, 1980
    Assignee: Stepan Chemical Company
    Inventor: Julius H. Deutsch
  • Patent number: 4222964
    Abstract: 2-(2,2-Dihalovinyl-3,3-dimethylcyclopropyl)ethanal is a new chemical compound and useful intermediate in the preparation of certain pyrethroid esters. It is prepared by hydrolysis of 2-[2-(2,2-dihalovinyl)-3,3-dimethylcyclopropyl]ethylidene diacetate, preferably in the presence of an acid.
    Type: Grant
    Filed: July 9, 1979
    Date of Patent: September 16, 1980
    Assignee: Shell Oil Company
    Inventors: Johannes Van Berkel, Johannes L. M. Syrier, Hendrik C. Kelderman
  • Patent number: 4221916
    Abstract: Saturated vicinal esters produced by reacting olefins with carboxylic acid and anhydrides thereof in the presence of oxygen and a vanadium- or ruthenium-containing catalyst.
    Type: Grant
    Filed: August 25, 1978
    Date of Patent: September 9, 1980
    Assignee: Phillips Petroleum Company
    Inventor: Paul R. Stapp
  • Patent number: 4221917
    Abstract: Monoolefins and diolefins are converted to corresponding esters in a process by contacting together at least one monoolefin, diolefin or mixture thereof, oxygen, at least one iodosoaryl dicarboxylate and at least one carboxylic acid, carboxylic acid anhydride or mixture thereof.
    Type: Grant
    Filed: March 3, 1978
    Date of Patent: September 9, 1980
    Assignee: Phillips Petroleum Company
    Inventor: Paul R. Stapp
  • Patent number: 4220800
    Abstract: Saturated vicinal esters are produced by reacting olefins with carboxylic acids and oxygen in the presence of a boron-containing catalyst component.
    Type: Grant
    Filed: September 5, 1978
    Date of Patent: September 2, 1980
    Assignee: Phillips Petroleum Company
    Inventor: Paul R. Stapp
  • Patent number: 4217290
    Abstract: 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: Grant
    Filed: June 20, 1979
    Date of Patent: August 12, 1980
    Assignee: Brichima S.p.A.
    Inventors: Paolo Maggioni, Francesco Mauri, Attilio Citterio
  • Patent number: 4214068
    Abstract: Phenolic curing agents, especially suitable for use in powder coatings, are prepared by reacting a dihydric phenol (diphenylol propane), a diepoxide (liquid diglycidyl ether of diphenylol propane), and a dicarboxylic acid (adipic acid) with the phenolic functionality in excess over the difference between the epoxy functionality and the acid functionality.
    Type: Grant
    Filed: May 10, 1979
    Date of Patent: July 22, 1980
    Assignee: Shell Oil Company
    Inventors: Gerardus C. M. Schreurs, Werner Th. Raudenbusch, Theodorus N. Visser
  • Patent number: 4209411
    Abstract: Methylol polyester derivatives of C.sub.12 -C.sub.22 hydrocarbon substituted succinic anhydride or acid which are the equimolar reaction products of said C.sub.12 -C.sub.22 hydrocarbon substituted succinic anhydride or acid and a cyclic poly(methylol) compound provide activity: in fuels as rust inhibitors; in automatic transmission fluids as copper corrosion inhibitors; and, in automotive, industrial and lubricating oils as sludge dispersants, rust-inhibitors, friction reducers (lubricity agents) and copper alloy corrosion inhibitors.
    Type: Grant
    Filed: March 23, 1979
    Date of Patent: June 24, 1980
    Assignee: Exxon Research & Engineering Co.
    Inventors: Esther D. Winans, Jack Ryer, Antonio Gutierrez, Harold Shaub
  • Patent number: 4198522
    Abstract: This disclosure describes 4-monoalkylaminophenyl carbinols (primary, secondary, and tertiary alcohols) and with derivatives and salts thereof useful as hypolipidemic and anti-atherosclerotic agents.
    Type: Grant
    Filed: September 27, 1977
    Date of Patent: April 15, 1980
    Assignee: American Cyanamid Company
    Inventor: Robert G. Shepherd
  • Patent number: 4194052
    Abstract: A sulfonic acid salt of an acyloxyalkylamine is prepared by reaction of an organic acid or amino-acid with a sulfonic acid salt of an alkanolamine. Isocyanates are prepared therefrom by reaction with phosgene.
    Type: Grant
    Filed: May 1, 1969
    Date of Patent: March 18, 1980
    Assignee: Rohm and Haas Company
    Inventors: Sheldon N. Lewis, Jerome F. Levy
  • Patent number: 4180676
    Abstract: A catalyst comprising a uranium compound, an alkali metal ion, and a halide, is effective to convert conjugated dienes in carboxylic acid media to diacyloxy olefins.
    Type: Grant
    Filed: August 25, 1977
    Date of Patent: December 25, 1979
    Assignee: Phillips Petroleum Company
    Inventor: Paul R. Stapp
  • Patent number: 4176232
    Abstract: A sulfonic acid salt of an acyloxyalkylamine is prepared by reaction of an organic acid or amino-acid with a sulfonic acid salt of an alkanolamine. Isocyanates are prepared therefrom by reaction with phosgene.
    Type: Grant
    Filed: June 27, 1968
    Date of Patent: November 27, 1979
    Assignee: Rohm and Haas Company
    Inventors: Sheldon N. Lewis, Jerome F. Levy
  • Patent number: 4171450
    Abstract: A process for the preparation of an unsaturated diester having the formula ##STR1## wherein R is an alkyl group of from 1 to 8 carbon atoms or an aralkyl group containing 6 carbon atoms in the ring and from 1 to 4 carbon atoms in the alkyl substituent, and R.sub.1 to R.sub.4 is hydrogen, a halogen, an alkyl group of from 1 to 4 carbon atoms or an aryl group containing 6 carbon atoms in the ring, by reacting carbon monoxide and oxygen with a diolefin having the formula ##STR2## wherein R.sub.1 to R.sub.4 which may be the same or different is as hereinabove described, in the presence of a catalytic amount of a platinum group metal compound, a copper for iron oxidant salt compound and a stoichiometric amount of a dehydrating agent.Alternatively, a ligand or coordination complex compound of the metal salt compound, and catalytic quantities of an alcohol may be employed.
    Type: Grant
    Filed: June 22, 1977
    Date of Patent: October 16, 1979
    Assignee: Atlantic Richfield Company
    Inventors: Haven S. Kesling, Jr., Lee R. Zehner
  • Patent number: 4166913
    Abstract: A process for the preparation of an unsaturated diester having the formula ##STR1## wherein R is an alkyl group of from 1 to 8 carbon atoms or an aralkyl group containing 6 carbon atoms in the ring and from 1 to 4 carbon atoms in the alkyl substituent and R.sub.1 to R.sub.4 is hydrogen, a halogen, an alkyl group of from 1 to 4 carbon atoms or an aryl group containing 6 carbon atoms in the ring, by reacting carbon monoxide, oxygen, at least a stoichiometric amount of an enol ether or alkoxycycloalkene and at least an equal molar quantity of an alcohol based on the enol ether or alkoxycycloalkene, with a diolefin having the formula ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 which may be the same or different is as hereinabove described, in the presence of a catalytic amount of a platinum group metal compound and a copper or iron oxidant salt compound.Alternatively, a ligand or coordination complex compound of the metal salt compound may be employed as a co-catalyst.
    Type: Grant
    Filed: July 8, 1977
    Date of Patent: September 4, 1979
    Assignee: Atlantic Richfield Company
    Inventors: Haven S. Kesling, Jr., Lee R. Zehner
  • Patent number: 4165432
    Abstract: Compounds containing peroxy linkages connecting similar polyol ester constituents are described. These peroxy di-ester polyols are prepared by the direct esterification of peroxy diacids with polyols, in the presence of a strong mineral acid catalyst. The peroxy di-ester polyol products function as free radical initiators and grafting bases in the graft copolymerization of unsaturated monomers with polyols. These graft copolymers are useful in the formulation of polyurethanes.
    Type: Grant
    Filed: October 18, 1977
    Date of Patent: August 21, 1979
    Assignee: Olin Corporation
    Inventors: Frank J. Preston, Theodore C. Kraus, Kiran B. Chandalia
  • Patent number: 4164615
    Abstract: A catalyst comprising a titanium compound, an alkali metal ion, and a halide, is effective for the conversion of conjugated diolefins to diacyloxy olefins.
    Type: Grant
    Filed: August 25, 1977
    Date of Patent: August 14, 1979
    Assignee: Phillips Petroleum Company
    Inventor: Paul R. Stapp
  • Patent number: 4163758
    Abstract: 2-Nitroethylcyclopentane compounds represented by the formula (I) ##STR1## wherein X represents a ##STR2## R and R.sup.1 each represents a hydrogen atom or a protective group for a hydroxy group, R.sup.2 represents an unsubstituted or substituted alkyl group having 1 to 8 carbon atoms and R.sup.5 represents a hydrogen atom or an alkyl group havng 1 to 4 carbon atoms, which are useful as intermediates for the synthesis of prostaglandin compounds, and a process for preparing the 2-nitroethylcyclopentane compounds of the formula (I).
    Type: Grant
    Filed: September 6, 1978
    Date of Patent: August 7, 1979
    Assignee: Sagami Chemical Research Center
    Inventors: Kiyosi Kondo, Daiei Tunemoto, Teruo Umemoto
  • Patent number: 4162363
    Abstract: Conjugated dienes or monoolefins are converted to diesters in a process utilizing a catalyst system comprising an alkali metal compound and a sulfur source comprising elemental sulfur or a sulfur halide, optionally with a halide source, in carboxylic acid media.
    Type: Grant
    Filed: August 25, 1977
    Date of Patent: July 24, 1979
    Assignee: Phillips Petroleum Company
    Inventor: Paul R. Stapp
  • Patent number: 4154958
    Abstract: A new class of thermally labile compounds having rust inhibiting properties is disclosed and claimed. The compounds (or formulations thereof) are especially useful as rust inhibitors when used either alone in distillate hydrocarbon fuels or in multi-purpose additive mixtures for distillate hydrocarbon fuels having a major proportion of hydrocarbon fuel distilling within the gasoline distillation range or other oil compositions to provide rust protection in fuel distribution systems which operate at ambient temperature (e.g., pipelines, tank trucks, and storage tanks). Preferred embodiments of the invention are alkylammonium carboxylate salt-ethoxylated alkyl phenol esters of a dicarboxylic acid.
    Type: Grant
    Filed: October 22, 1976
    Date of Patent: May 15, 1979
    Assignee: Rohm and Haas Company
    Inventors: Joseph M. Bollinger, Richard H. Hanauer, Warren H. Machleder
  • Patent number: 4150237
    Abstract: Compounds of the structure R(SCH.sub.2 CHOHCH.sub.2 X).sub.n when n=1 to 4 and R is a hydrocarbon, ether, ester, acetal, hydroxy aliphatic, hydroxy aromatic, imide or amide group or halogenated derivatives thereof are prepared by reacting 1-halo-3-mercapto-2-propanol with an aliphatically unsaturated compound using free radical initiators as catalysts. The compounds in which R is an unsaturated or polyunsaturated aliphatic hydrocarbon group of 2 to 24 carbon atoms, or an unsaturated or polyunsaturated cycloaliphatic group, and those in which the aliphatic or cycloaliphatic group is connected through two or more of the polyunsaturated to two or more --S--CH.sub.2 CHOHCHCl groups, and compounds where R is an alkylene or polyalkylene substituted aromatic group and the hydroxy, thioalkyl, alkoxy, aryloxy, ester, carbamidoalkyl and sulfamidoalkyl, halogenated derivatives of said groups are new compounds. The thioether halohydrins can be converted to epoxides.
    Type: Grant
    Filed: January 16, 1976
    Date of Patent: April 17, 1979
    Assignee: The Dow Chemical Company
    Inventors: Richard A. Hickner, Corwin J. Bredeweg
  • Patent number: 4145559
    Abstract: Esters of 4-substituted 2-methyleneglutaric acids are prepared by reacting an ester of acrylic acid with an ester of an .alpha.-substituted acrylic acid, such as an ester of methacrylic acid, in the presence of a tertiary organic phosphine, an organic phosphorus triamide, an organic phosphonous diamide, or an organic phosphinous amide.
    Type: Grant
    Filed: November 6, 1974
    Date of Patent: March 20, 1979
    Assignee: Rohm and Haas Company
    Inventors: Joseph W. Nemec, Richard B. Wuchter
  • Patent number: 4145556
    Abstract: Novel N,N'-bis?(alkylhydroxyphenyl)alkanoyloxyhydrocarbyl!oxamides which can be prepared by reacting an alkylhydroxyphenylalkanoic acid, an ester or anhydride thereof or a corresponding acid halide with an N,N'-bis(hydroxyhydrocarbyl)oxamide, are useful as stabilizers of organic materials normally subject to oxidative deterioration, e.g. polymers such as polyolefins.
    Type: Grant
    Filed: December 21, 1977
    Date of Patent: March 20, 1979
    Assignee: Monsanto Company
    Inventors: Richard H. Hirsch, William H. Selcer
  • Patent number: 4138580
    Abstract: A process for preparing a diester of a dicarboxylic acid having two more carbon atoms than the unsaturated hydrocarbon used as a starting material, which comprises subjecting an unsaturated hydrocarbon, carbon monoxide and an alcohol to reaction in the presence of a platinum group metal in combination with one or more compounds selected from the group consisting of nitric acid, a nitrogen oxide and an ester of nitrous acid.
    Type: Grant
    Filed: September 29, 1977
    Date of Patent: February 6, 1979
    Assignee: Ube Industries, Ltd.
    Inventors: Sumio Umemura, Kanenobu Matsui, Yoshinari Ikeda, Katsuro Masunaga
  • Patent number: 4132702
    Abstract: Compounds of the formula I ##STR1## in which R.sub.1 and R.sub.2 independently of one another denote alkyl, cycloalkyl or aralkyl, R.sub.3 denotes hydrogen or, conjointly with R.sub.1, denotes tetramethylene, R.sub.4 denotes hydrogen or lower alkyl or, conjointly with R.sub.2, denotes tetramethylene, R.sub.5 denotes hydrogen, alkyl, aralkyl, acyloxyalkyl, oxaalkyl or phenyl, R.sub.6 denotes hydrogen, alkhyl, phenyl or the group or, conjointly with R.sub.5, denotes alkylene, R.sub.7 denotes hydrogen, alkyl, phenyl, benzyl or alkylphenyl or, conjointly with R.sub.5 or R.sub.6, denotes alkylene or, conjointly with R.sub.5 and R.sub.6, denotes alkanetriyl, R.sub.5, R.sub.6 and R.sub.7 together containing at least one carbon atom, Y denotes --O-- or --NH--, P denotes 1, 2, 3 or 4 and A denotes hydrogen or a group which is derived from an organic or inorganic oxygen acid A-(OH).sub.p, are suitable for stabilizing organic material against thermo-oxidative degradation.
    Type: Grant
    Filed: July 27, 1976
    Date of Patent: January 2, 1979
    Assignee: Ciba-Geigy Corporation
    Inventors: Andreas Schmidt, Kurt Schwarzenbach
  • Patent number: 4128532
    Abstract: The instant invention is broadly directed to novel polyether esters and the use thereof in manufacturing polyurethane resins. The novel products are produced by esterifying an alkoxylated, halogenated bisphenol, a polycarboxylic acid and a dihydric alcohol.
    Type: Grant
    Filed: November 21, 1977
    Date of Patent: December 5, 1978
    Assignee: Bayer Aktiengesellschaft
    Inventors: Erich Eimers, Rolf Dhein, Rolf Wiedermann
  • Patent number: 4127736
    Abstract: An asymmetric synthesis of optically active prostaglandin F.sub.2.alpha. from cyclopentadiene including intermediates in this synthesis.
    Type: Grant
    Filed: September 19, 1977
    Date of Patent: November 28, 1978
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Naresh K. Chadha, John J. Partridge, Jr., Milan R. Uskokovic
  • Patent number: 4112235
    Abstract: Carboxylic acids may be esterified by reaction with esters in the presence of a catalytic amount of a tin halide catalyst, the reaction being effected at temperatures ranging from about 0.degree. to about 150.degree. C.
    Type: Grant
    Filed: October 28, 1976
    Date of Patent: September 5, 1978
    Assignee: UOP Inc.
    Inventor: Louis Schmerling
  • Patent number: 4105792
    Abstract: Prostan-1-ol esters and intermediates for their preparation are described; the former compounds exhibit improved organ specificity and a longer duration of activity at lower dosages than the corresponding non-esterified prostaglandins and are useful, inter alia, in triggering abortion, inducing labor and regulating the menstrual cycle.
    Type: Grant
    Filed: May 25, 1976
    Date of Patent: August 8, 1978
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Olaf Loge, Eckehard Schillinger
  • Patent number: 4103091
    Abstract: This invention provides intermediates which are essential for a new chemical method which converts terrein, a fungal metabolite, to an intermediate which is known to be useful for the preparation of prostaglandins of the C series and analogs of other prostaglandins.
    Type: Grant
    Filed: July 22, 1976
    Date of Patent: July 25, 1978
    Assignee: The Ohio State University Research Foundation
    Inventors: Lester Allen Mitscher, George Winfred Clark, III, Gordon Herman Bokelman
  • Patent number: 4083990
    Abstract: The present invention relates to novel not naturally occurring 10,11-dihydro-derivatives of prostaglandins of the A-series as well as a process for their preparation. The compounds of the invention have an antiprostaglandin effect and may be used as medicaments for the inhibition or suppression of pharmacological properties of the prostaglandins.
    Type: Grant
    Filed: June 23, 1976
    Date of Patent: April 11, 1978
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Milos Babej, Wilhelm Bartmann, Gerhard Beck, Ulrich Lerch
  • Patent number: 4076949
    Abstract: A process for the preparation of oxalate esters by reacting an alcohol with a mixture of carbon monoxide and oxygen in the presence of a catalytic mixture of:(a) a palladium, rhodium, platinum, copper, or cadmium metal salt compound or mixture thereof,(b) an aliphatic, cycloaliphatic, aromatic or heterocyclic amine or ammonia,(c) a copper (I), copper (II), iron (II) or iron (III) oxidant salt compound, and(d) an ammonium or substituted ammonium salt compound or acid with a counterion other than a halide.Alternatively a ligand or coordination complex compound of the metal salt compound may be employed.
    Type: Grant
    Filed: May 9, 1977
    Date of Patent: February 28, 1978
    Assignee: Atlantic Richfield Company
    Inventor: Lee R. Zehner
  • Patent number: 4074061
    Abstract: Disclosed is an unsaturated polyester containing formal linkages. The polyester is comprised of the following repeating unit ##STR1## wherein X is a positive integer from 2 to 10, R is the divalent radical remaining after removal of the terminal carboxyl group from an .alpha.,.beta.-ethylenically unsaturated dicarboxylic acid, and R' is the divalent radical remaining after removal of the terminal hydroxyl groups from an aliphatic or cycloaliphatic glycol. The polyesters of this invention exhibit a combination of a desirable hardness and a desirable impact strength upon curing.
    Type: Grant
    Filed: October 26, 1976
    Date of Patent: February 14, 1978
    Assignee: Eastman Kodak Company
    Inventor: Harry R. Musser