Preparing Esters By Esterification Or Carbonylation Patents (Class 560/204)
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Patent number: 4902821Abstract: This invention relates to a linear, low-molecular-weight polyester-based polyol having terminal primary hydroxyl groups, low viscosity, high solids content and having the structural formula: ##STR1## where n is 1 or 2 and at least 70% by weight is n=1, and m=2-10, said polyol being substantially free of cyclohexane dimethanol.Type: GrantFiled: December 27, 1982Date of Patent: February 20, 1990Assignee: King Industries, Inc.Inventors: Leonard J. Calbo, Jr., Lawrence V. Gallacher
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Patent number: 4888441Abstract: This invention relates to certain linear, low-molecular-weight polyester-based polyols having at least two hydroxyl groups, low viscosity, high solids content and having the structural formula: ##STR1## wherein R is a moiety derived from a saturated aliphatic polyhydric alcohol; n is 1 or 2, and at least about 50% by weight, of n is n=1; p is 0 to 4 inclusive and m is 2 to 10 inclusive; said polyol being substantially free of any unreacted polyhydric alcohol.Type: GrantFiled: December 21, 1984Date of Patent: December 19, 1989Assignee: King Industries, Inc.Inventors: Leonard J. Calbo, Jr., Lawrence V. Gallacher
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Patent number: 4886613Abstract: A traction fluid comprising a diester or its derivative represented by the formula: ##STR1## wherein A' is an ester linkage, n is an integer of 1 to 10, R.sub.1 is independently selected from hydrogen and C.sub.1 to C.sub.8 alkyl groups, and R.sub.2 is the same or different and is selected from hydrogen and C.sub.1 to C.sub.3 alkyl groups.Type: GrantFiled: July 23, 1987Date of Patent: December 12, 1989Assignee: TOA Nenryo Kogyo, K.K.Inventors: Narihiko Yoshimura, Yasuji Komatsu, Hirotaka Tomizawa
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Patent number: 4886614Abstract: A traction fluid comprising a diester or its derivative represented by the formula ##STR1## wherein: A40 is an ester linkage of --COO-- or --OOC--;n is an integer of 1 to 6;R.sub.1 is independently selected from hydrogen and alkyl groups containing 1 to 8 carbon atoms; andR.sub.2 is independently selected from alkyl groups containing from 1 to 3 carbon atoms.Type: GrantFiled: June 23, 1987Date of Patent: December 12, 1989Assignee: Toa Nenryo Kogyo, K.K.Inventors: Narihiko Yoshimura, Hirotaka Tomizawa, Yasuji Komatsu
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Patent number: 4885383Abstract: A process for the preparation of methyl carboxylates by the reaction of mono or dicarboxylic acids having more than 5 carbon atoms and methanol in the presence of acidic catalysts at temperatures from 100.degree. to 150.degree. C. and below the boiling point of the carboxylates being produced.Type: GrantFiled: September 23, 1988Date of Patent: December 5, 1989Assignee: Hoeschst AktiengesellschaftInventors: Jurgen Weber, Helmut Springer, Peter Lappe
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Patent number: 4883495Abstract: Amino-containing alkenylsuccinic esters of the formulae ##STR1## where R denotes linear or branched C.sub.1 -C.sub.20 -alkyl, R.sub.1 denotes hydroxy-C.sub.2 -C.sub.6 -alkyl or C.sub.1 -C.sub.4 -alkyl, R.sub.2 denotes methyl or ethyl, R.sub.3 denotes C.sub.6 -C.sub.20 -alkyl, preferably C.sub.12 -C.sub.18 -alkyl, or C.sub.6 -C.sub.20 -alkenyl, preferably C.sub.12 -C.sub.18 -alkenyl, A denotes --C.sub.2 H.sub.4 -- or C.sub.3 H.sub.7 -- and n denotes a number from 1 to 10, preferably from 3 to 8, the preparation thereof and the use thereof as thermostable lubricants in spin finishes.Type: GrantFiled: September 21, 1988Date of Patent: November 28, 1989Assignee: Hoechst AktiengesellschaftInventors: Lothar Jaeckel, Rolf Kleber, Bernhard Mees
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Patent number: 4883899Abstract: An end carboxyl bearing reactive vinyl monomer represented by the formula: ##STR1## wherein R.sub.1 is hydrogen or methyl group; R.sub.2 is a bivalent aliphatic hydrocarbon having 2 to 10 carbon atoms, a bivalent alicyclic hydrocarbon having 6 to 7 carbon atoms, phenylene substituted with halogen, sulfo or carboxyl group; A is a repeating unit of the formula: ##STR2## R.sub.3 is ethylene or propylene; R.sub.4 is an alkylene having 2 to 7 carbon atoms; R.sub.5 is an alkylene having 2 to 5 carbon atoms; m is an integer of 1 to 10 and n is an integer of 2 to 50. The present reactive vinyl monomer is very useful as a constituting unit of vinyl resin.Type: GrantFiled: April 28, 1989Date of Patent: November 28, 1989Assignee: Nippon Paint Co., Ltd.Inventors: Hisaichi Muramoto, Keizou Ishii, Tadafumi Miyazono
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Patent number: 4874888Abstract: In a process for preparing a diester of oxalic acid by the vapor phase catlytic reaction of carbon monoxide with an ester of nitrous acid in the presence of a catalyst composed of a solid carrier and a catalyst component supported on the carrier, the improvement wherein said catalyst component is composed of(a) a platinum-group metal or a salt thereof, and(b) at least one member selected from the group consisting of iron and an iron (II or III) compound,the atomic ratio of the component (a) to the component (b) as metal being from 10,000:1 to 1:4.Type: GrantFiled: October 28, 1983Date of Patent: October 17, 1989Assignee: UBE Industries, Ltd.Inventors: Yasushi Shiomi, Tokuo Matsuzaki, Katsuro Masunaga
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Patent number: 4873023Abstract: Compounds of the general formulae ##STR1## where R is versatyl and R' is unsubstituted or alkyl-substituted straight-chain alkylene of 4 or 5 carbon atoms can be prepared by reacting the versatic ester of 1,3-dihydroxy-propyl-2 acrylate and/or of 2,3-dihydroxy-propyl-1 acrylate with equimolar amounts of saturated or monoolefinically unsaturated cyclic dicarboxylic anhydrides having 4 or 5 carbon atoms and an oxygen atom in the ring at from 50.degree. to 150.degree. C. in the presence of customary esterification catalysts and can be used as reactive diluents in radiation-curable contact adhesives.Type: GrantFiled: November 21, 1988Date of Patent: October 10, 1989Assignee: BASF AktiengesellschaftInventors: Guenther Schulz, Wolfgang Druschke, Helmut Jaeger
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Patent number: 4868328Abstract: Process for the selective oxidative carbonylation of a conjugated diene with carbon monoxide and an alcohol in a quantity of at least 2 mol equivalents per mol diene, in the presence of a catalyst system which comprises the following components:(a) a compound of a metal, selected from one or more platinum group metals,(b) an oxidizing agent in the form of quinone and/or derivatives thereof, and(c) a compound of a metal, selected from manganese or vanadium.Type: GrantFiled: November 20, 1987Date of Patent: September 19, 1989Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4861912Abstract: Process for preparing adipic acid or esters thereof by:(1) reacting 1,3-butadiene with CO and water or an alcohol with formation of pentenoic acid or esters thereof in the presence of a first carbonylation catalyst comprising a Pd compound and a polydentate ligand containing P, As or Sb,(2) isolating pentenoic acid or esters thereof from the reaction mixture, and(3) reacting the isolated pentenoic acid or esters with CO and water or an alcohol in the presence of a second carbonylation catalyst.Type: GrantFiled: March 18, 1988Date of Patent: August 29, 1989Assignee: Shell Oil CompanyInventors: Eit Drent, Johan Van Gogh
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Patent number: 4861895Abstract: Aqueous solutions which are obtained in the carbalkoxylation of olefinically unsaturated compounds and contain heterocyclic aromatic nitrogen bases, their transformation products and lower fatty acids and/or their salts are treated by a process in which (a) the aqueous solution is heated to 150.degree.-300.degree. C. under from 10 to 300 bar and (b) heterocyclic aromatic nitrogen bases which are formed again from the transformation products are then separated off.Type: GrantFiled: July 24, 1987Date of Patent: August 29, 1989Assignee: BASF AktiengesellschaftInventors: Werner Bertleff, Robert Maerkl, Peter Magnussen, Gebhard Kuehn, Peter Stops
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Patent number: 4859792Abstract: The instant invention involves a process for preparing acrylic acid esters which comprises coreacting an acrylic acid and an aliphatic mono or polyol by maintaining one of the reactants in a reactor at elevated temperatures and adding the other reactant to the reactor over a period of time. By employing this process esterification times are reduced significantly.Type: GrantFiled: March 7, 1988Date of Patent: August 22, 1989Assignee: Hoechst Celanese Corp.Inventors: Thomas M. Powanda, Robert H. Imes, George L. Collins
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Patent number: 4857657Abstract: Hexene-1,6-dioates, readily hydrogenated into adipates (which in turn are conveniently hydrolyzed into adipic acid), are prepared by reacting carbon monoxide, an alcohol and at least one dichlorobutene, in the presence of a catalytically effective amount of palladium or a palladium compound and no more than two equivalents (relative to the dichlorobutene) of a tertiary amine reaction promoter; in an alternate embodiment, the tertiary amine and the dichlorobutene are first converted into a quaternary ammonium chloride intermediate.Type: GrantFiled: November 16, 1987Date of Patent: August 15, 1989Assignee: Rhone-Poulenc ChimieInventors: Philippe Denis, Jean-Marc Frances
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Patent number: 4845270Abstract: The present invention discloses the use of propanone 1,3-disulfonic acid as an esterification catalyst. This catalyst has a significantly higher reaction rate when compared to conventional esterification catalysts, such as methanesulfonic acid and sulfuric acid.Type: GrantFiled: March 25, 1988Date of Patent: July 4, 1989Assignee: Pennwalt CorporationInventor: Stanley R. Sandler
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Patent number: 4827022Abstract: An improved process for the preparation of dimethylmaleate by the esterification of maleic acid anhydride, maleic acid monomethylester, maleic acid or mixtures thereof with methanol in the presence of catalytic quantities of sulphuric acid, which comprises carrying out the esterification reaction within 20 to 120 minutes in a multistage bubble cap column reactor at temperatures of from 90.degree. to 140.degree. C. and with methanol excesses of from 0.4 to 2.0 mole per mole of the dimethylmaleate to be produced.Type: GrantFiled: March 21, 1988Date of Patent: May 2, 1989Assignee: Bayer AktiengesellschaftInventors: Bernd Makowka, Hans-Dieter Block
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Patent number: 4827023Abstract: The invention discloses an improvement to the selective production of dialkyl succinates by the known process of oxidative carbonylation of an olefin with carbon monoxide, oxygen, and an alkyl alochol in the presence of a catalyst wherein the improvement comprises using a sulfone as the reaction solvent. The use of a sulfone, of which sulfolane is a preferred example, results in fast reaction rates and high selectivity to dialkyl succinates even in the absence of a dehydrating agent.Type: GrantFiled: November 27, 1987Date of Patent: May 2, 1989Assignee: Sun Refining and Marketing CompanyInventor: Chao-Yang Hsu
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Patent number: 4795824Abstract: A process is described for the production of a dialkyl maleate by reaction of maleic anhydride with an alkyl alcohol in a monoesterification zone to form the corresponding monoalkyl maleate, followed by reaction of resulting monoalkyl maleate with further alkyl alcohol to form the corresponding dialkyl maleate, which includes the steps of supplying a first liquid feed comprising said monoalkyl maleate to a secondary esterification zone containing a charge of a solid esterification catalyst, supplying a second feed stream comprising said alkyl alcohol to said secondary esterification zone, maintaining said secondary esterification zone at an elevated temperature sufficient to form or to maintain therein a vaporous stream containing said alkyl alcohol, intimately contacting said first liquid feed in said secondary esterification zone in the presence of said catalyst with said vaporous feed stream, recovering from said secondary esterification zone a vaporous effluent stream containing, in addition to alkyl alcoType: GrantFiled: July 31, 1987Date of Patent: January 3, 1989Assignee: Davy McKee (London) LimitedInventors: John W. Kippax, Colin Rathmell
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Patent number: 4790963Abstract: A process for producing an ester is disclosed comprising contacting a gaseous reactant containing at least one organic hydroxy compound and a mixture of carbon monoxide and hydrogen with an ester synthesis catalyst of the formulaM.sub.a A.sub.b RuCu.sub.c N.sub.z O.sub.xwhereinM is selected from the group consisting of Ce, Cr, Fe, Mn and mixtures thereof,A is an alkali metal, alkaline earth metal or mixture thereof,a is from 0 to about 1,b is from 0.002 to about 10,c is from 0.2 to about 20,z is from 0 to about 196 by weight,x is the number of oxygens needed to fulfill the valence requirements of the other elements.The organic hydroxy compound can be provided separately or formed by contacting a mixture of carbon monoxide and hydrogen with an alcohol synthesis catalyst at an elevated temperature and pressure. The alcohol synthesis catalyst and ester synthesis catalyst can be in tandem or mixed.Type: GrantFiled: August 20, 1984Date of Patent: December 13, 1988Assignee: The Standard Oil CompanyInventors: Thomas G. Attig, Anne M. Graham, Frederick A. Pesa
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Patent number: 4788334Abstract: A process for the production of carboxylic acids by the hydrocarboxylation of olefinically unsaturated alkenes or esters using a rhodium catalyst, an iodide promoter, a solvent selected from the class consisting of methylene chloride, 1,2-dichloroethane, and C.sub.6 to C.sub.9 aromatic solvents, and an accelerator which is an acid having a pKa in the range of 4.2 to 5.2.Type: GrantFiled: December 10, 1986Date of Patent: November 29, 1988Assignee: E. I. Du Pont de Nemours and CompanyInventor: Patrick M. Burke
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Patent number: 4781868Abstract: Method for making alpha, beta-unsaturated carboxylic acid anhydrides by carbonylation of esters of acrylic acid or methacrylic acid in the presence of a catalyst system containing at least one noble metal from group VIII of the periodic table, for example rhodium, the reaction being carried out at 70.degree. C. to 350.degree. C. and at pressures from 1 to 500 bar in the presence of a halogen or of a halogen compound, and in particular of iodine or an iodine compound, as a promoter.Type: GrantFiled: December 2, 1986Date of Patent: November 1, 1988Assignee: Rohm GmbHInventor: Klaus Langerbeins
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Patent number: 4780542Abstract: The invention relates to the preparation of an ester or an amide from an anhydride with an alcohol or an amine, wherein the anhydride is first prepared by reacting an acid and an alkyl chloroformate in a 100% aqueous medium, that is, 100% water.Type: GrantFiled: September 26, 1983Date of Patent: October 25, 1988Assignee: Montefiore Medical CenterInventor: Iraj Lalezari
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Patent number: 4777284Abstract: Carbalkoxy-containing aliphatic compounds are prepared continuously by reacting an olefinically unsaturated aliphatic compound with carbon monoxide and an alkanol in the presence of a cobalt carbonyl catalyst and a tertiary nitrogen base at from 80.degree. to 200.degree. C. and under from 100 to 1,200 bar by an improved process in which carbon monoxide is circulated, and a carbon dioxide content of from 0.1 to 2% by volume is maintained in the carbon monoxide fed to the reaction.Type: GrantFiled: November 5, 1987Date of Patent: October 11, 1988Assignee: BASF AktengesellschaftInventors: Robert Maerkl, Werner Bertleff, Gebhard Kuehn, Paul Panitz, Peter Stops, Rudolf Kummer, Guenter Schuch
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Patent number: 4772743Abstract: Reaction products of 1 mole 2,2-bis-(4-hydroxycyclohexyl)-propanes with 2 moles carboxylic acid anhydrides and their use as emulsifiers for emulsion polymerization.Type: GrantFiled: November 9, 1987Date of Patent: September 20, 1988Assignee: Bayer AktiengesellschaftInventors: Adolf Schmidt, Herbert Eichenauer, Alfred Pischtschan
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Patent number: 4769388Abstract: A new series of oligomeric or polymeric compounds having a poly(ester) structure, wherein the monomeric starting materials are 1,10-bis(2-hydroxyethylthio)decane, poly(oxyethyleneglycol)s or poly(oxypropyleneglycol)s and carboxylic acids, the process for the preparation thereof and the therapeutic use thereof.Type: GrantFiled: August 7, 1986Date of Patent: September 6, 1988Assignee: Nuovo Consorzio Sanitario NazionaleInventors: Paolo Ferruti, Giancarlo Scapini
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Patent number: 4740272Abstract: A method of producing substantially pure dialkyl maleate by separating monoalkyl maleate from dialkyl maleate in a short residence time distillation zone while minimizing reversion of the monoalkyl maleate to alkanol and maleic anhydride and without having to neutralize the monoalkyl maleate.Type: GrantFiled: March 31, 1987Date of Patent: April 26, 1988Assignee: Davy McKee (London) LimitedInventors: Ernesto Vera-Castaneda, Diane A. Montevideo, David J. Miller, John E. Logsdon, David R. Bryant
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Patent number: 4739107Abstract: Process for the preparation of dicarboxylate esters by reacting an optionally substituted ethylenically unsaturated hydrocarbon having two carbon atoms less than said dicarboxylic acid, CO and an alcohol in the presence of a Group VIII noble metal or a compound thereof, a quinone and optionally, a redox agent and molecular oxygen.Type: GrantFiled: January 12, 1987Date of Patent: April 19, 1988Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4733006Abstract: The present invention provides for an improved process wherein an olefin, an alcohol, or an ester, halide or ether derivative of said alcohol is reacted with carbon monoxide in a liquid phase in the presence of a catalyst system that contains (a) a rhodium component, and (b) and iodine or bromine component. By passing at least a portion of the liquid reaction mass from the reaction zone to a separation zone of substantially lower CO partial pressure, at least a portion of the carbonylation products, as well as unreacted carbon monoxide, inert gases and unreacted olefin, alcohol or alcohol derivatives are vaporized and can be withdrawn from the separation zone. Precipitation of the rhodium catalyst under carbon monoxide deficient conditions is prevented or retarded by addition to the carbon monoxide deficient zones of the system of a catalyst stabilizer which is a germanium (IV) compound, an alkali metal compound, and mixtures thereof.Type: GrantFiled: August 18, 1983Date of Patent: March 22, 1988Assignee: Monsanto CompanyInventors: Thomas C. Singleton, Frank E. Paulik
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Patent number: 4731467Abstract: Process for the preparation of diesters of 2-butenedioic acids by reacting an optionally substituted acetylenically unsaturated hydrocarbon having two carbon atoms less than said 2-butenedioic acid, carbon monoxide, a quinone in the presence of a of Group VIII noble metal or a compound thereof, and optionally, a redox agent.Type: GrantFiled: January 12, 1987Date of Patent: March 15, 1988Assignee: Shell Oil CompanyInventors: Eit Drent, Antonius J. M. Breed
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Patent number: 4730080Abstract: Preparation of diesters of alkanedioic acids by reacting a dihydrocarbyl peroxide with carbon monoxide and optionally with an alpha-ethylenically unsaturated compound in the presence of a solvent, a Group VIII noble metal or a compound thereof and of a cupric salt.Type: GrantFiled: June 27, 1986Date of Patent: March 8, 1988Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4714775Abstract: The invention relates to novel phenylcyclohexyl dicarboxylates usable as liquid crystals or for improving the elastic properties of nematic liquid crystals.These compounds are in accordance with formula (I) ##STR1## in which R.sup.1 and R.sup.2, which can be the same or different, represent a hydrogen atom or an alkyl radical having 1 to 12 carbon atoms and n is an integer between 2 and 16.They can be prepared by reacting the diacid of formula HOOC(CH.sub.2).sub.n --COOH with corresponding substituted phenylcyclohexanols.Type: GrantFiled: October 1, 1986Date of Patent: December 22, 1987Assignee: Commissariat a l'Energie AtomiqueInventor: Anne-Marie Giroud
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Patent number: 4713483Abstract: A process for the production of diesters of oxalic acid by oxidative carbonylation of alcohols with carbon monoxide and oxygen as oxidizer at pressures of 1 to 700 atmospheres and in a temperature range between 20.degree. and 250.degree. C. in a reaction phase containing the alcohol and, as catalyst, palladium and at least one metal halide in catalytically effective amounts, whereby a catalyst system is used which consists of palladium, at least one metal halide, and an activated carbon which has been pretreated before use by heating to 200.degree.-1,500.degree. C. in a gas atmosphere G, differing from air.The gas atmosphere G, differing from air, consists, preferably, of at least one of the gases (a) nitrogen; (b) nitrogen compounds, except those with nitrogen-oxygen bonds; or (c) carbon monoxide; and may optionally contain an accompanying gas.Type: GrantFiled: April 9, 1986Date of Patent: December 15, 1987Assignee: Rohm GmbH Chemische FabrikInventors: Klaus Langerbeins, Gunther Schroder, Hans-Peter Boehm
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Patent number: 4711922Abstract: Citrate esters are formed utilizing organic titanates as a catalyst allowing excess alcohol to be removed. Four citrate esters have been found which provide advantageous plasticizing properties to PVC compositions which include superior toxicity test results and superior soapy water extraction test results. The four citrate esters are: acetyltri-n-hexyl citrate, n-butyryltri-n-hexyl citrate, acetyltri-n-(hexyl/octyl/decyl) citrate, and acetyltri-n-(octyl/decyl) citrate. Articles formed from the PVC plasticized mixtures are extremely useful in the medical or health care field as they demonstrate a low order of toxicity.Type: GrantFiled: May 21, 1986Date of Patent: December 8, 1987Assignee: Morflex Chemical Company, Inc.Inventors: Ezekiel H. Hull, Edward P. Frappier
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Patent number: 4698186Abstract: A process for reducing the free fatty acid content of fats and oils by esterifying the free fatty acids with a lower monoalcohol in the presence of an acidic cation exchange resin as a solid esterification catalyst.Type: GrantFiled: January 21, 1986Date of Patent: October 6, 1987Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Lutz Jeromin, Eberhard Peukert, Gerhard Wollmann
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Patent number: 4692549Abstract: Production of dialkyl adipate by reaction of butadiene, carbon dioxide, and a lower alkyl alcohol in the presence of a cobalt catalyst and a tertiary nitrogen base cocatalyst to form a liquid mixture containing alkyl 3-pentenoate, adding alkanoic acid to the mixture in an amount sufficient to keep the cobalt catalyst active, and then reacting the mixture to form dialkyl adipate. The acid addition increases the rate of reaction relative to catalyst deactivation rate and reduces the consumption of the tertiary nitrogen base cocatalyst.Type: GrantFiled: June 27, 1986Date of Patent: September 8, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventor: Harold S. Bruner, Jr.
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Patent number: 4691046Abstract: A novel compound, viz, butanedioic acid mono [(2-dimethylamino)ethyl ester] succinate has the following formula: ##STR1## The compound of this invention exhibits adaprogenic and stressoprotective effects.Type: GrantFiled: January 2, 1987Date of Patent: September 1, 1987Assignees: Institut Organicheskoi Khimii Ordena Lenina I Ordena Druzhby Narodov Akademii Nauk Ukrainskoi SSR, Instiut Farmakologii Akademii Meditsinskikh Nauk SSSRInventors: Miron O. Lozinsky, Jury G. Bobkov, Alla F. Shinanjuk, Jury I. Gevaza, Leonid N. Markovsky, Galina A. Kuznetsova, Valentin A. Markin, Natalya N. Kleimenova, Antonina I. Tentsova, Alexandr N. Motalov, Sergei B. Seredinin, Vladimir F. Katkov, Vasily M. Vinogradov, Vladimir I. Kulinsky
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Patent number: 4691047Abstract: A process for the carbonylation of a conjugated diene with CO and an alcohol or water in the presence of an aprotic solvent is carried out in the presence of a dissolved catalytic system prepared by combining a Pd(II) compound, at least 5 mol of a triarylphosphine per gram atom of Pd and at least 1 mol of HC1 per gram atom of trivalent P.Type: GrantFiled: March 26, 1986Date of Patent: September 1, 1987Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4689429Abstract: Liquid copolyesters useful as plasticizers for vinyl resins are provided. The copolyesters are obtained by the esterification of specific aliphatic dicarboxylic acid ester mixtures with 1,4-butanediol and an aliphatic saturated monofunctional alcohol. The copolyesters have acceptably low solidification points; they are resistant to hydrocarbon extraction; and they impart good low-temperature flexibility to PVC compositions plasticized therewith.Type: GrantFiled: August 7, 1986Date of Patent: August 25, 1987Assignee: National Distillers and Chemical CorporationInventors: William J. Mertz, William L. O'Brien
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Patent number: 4689430Abstract: A process for the production of a dialkyl carbonate, e.g. dimethyl carbonate, or a dialkyl oxalate, e.g. dimethyl oxalate, from butane, oxygen carbon monoxide and an alcohol is provided in a series of integrated process steps. In the case of a dialkyl oxalate, the product can be hydrogenated further to produce an ether of ethylene glycol.Type: GrantFiled: November 17, 1986Date of Patent: August 25, 1987Assignee: The British Petroleum Company p.l.c.Inventors: George E. Morris, Gillian Wainhouse
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Patent number: 4681975Abstract: A polyester being liquid at 25.degree. C. comprises a polybasic acid and a polyhydric alcohol as its monomer constituents, wherein the polyhydric alcohol is composed at least partially of 1,2-butanediol.Type: GrantFiled: March 13, 1986Date of Patent: July 21, 1987Assignee: Mitsubishi Monsanto Chemical CompanyInventors: Ryuichi Hasegawa, Kohji Hayashi
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Patent number: 4681707Abstract: Carboxylic acid esters are produced by reacting an unsaturated hydrocarbon, for example an olefin or an alkyne, with carbon monoxide and an alcohol in the presence of a protonic acid and as catalyst (a) at least one of the metals palladium, rhodium, ruthenium, iridium and cobalt, and (b) copper. In a modification of the invention carboxylic acids are produced by omitting the alcohol reactant and replacing it with water in an amount up to 8 mole equivalents based on the unsaturated hydrocarbon and a solvent other than an alochol, for example tetrahydrofuran.Type: GrantFiled: April 23, 1984Date of Patent: July 21, 1987Assignee: The British Petroleum Company p.l.c.Inventors: Howard Alper, Bertrand Despeyroux, David J. H. Smith, James B. Woell
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Patent number: 4670580Abstract: The invention provides a process for the preparation of a polyester oligomer capable of being further polymerized to a high polymer wherein a glycol-dicarboxylic acid ester feed is treated in a secondary esterification zone under conditions such that the partial vapor pressures of water and glycol are maintained at a cumulative level of less than 740 Torr, with water and glycol vapors being continuously removed from the secondary esterification zone, and free glycol being added to the secondary esterification zone in an amount sufficient to maintain a stable amount of liquid glycol in the secondary esterification zone.Type: GrantFiled: March 31, 1986Date of Patent: June 2, 1987Assignee: Celanese CorporationInventor: Charles J. Maurer
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Patent number: 4667053Abstract: This invention relates to the carbonylation of olefins. More particularly it involves the carbonylation of an .alpha.-olefins such as ethylene to form diesters, such as, for example, dimethyl succinate, 3-methoxypropionate and dimethylcarbonate by a process comprising reacting said olefin with carbon monoxide, oxygen and an alkanol in the presence of a heterogeneous palladium/copper catalyst, on a polymer support.Type: GrantFiled: June 30, 1986Date of Patent: May 19, 1987Assignee: Texaco Inc.Inventor: Jiang-Jen Lin
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Patent number: 4665213Abstract: Carboxylic acid esters are produced by reacting an olefinic hydrocarbon with an ester of formic acid in the presence of both carbon monoxide and oxygen at a temperature of up to 200.degree. and a pressure of up to 300 bar in the presence of water, typically in an amount of from 0.01 to 5% w/w, a source of protons, which is preferably a mineral acid or a tectometallosilicate in the hydrogen form, and as catalyst (a) a source of palladium, and (b) a source of copper.Type: GrantFiled: August 25, 1986Date of Patent: May 12, 1987Assignee: The British Petroleum Company p.l.c.Inventors: Howard Alper, David J. H. Smith
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Patent number: 4663477Abstract: A process is provided for the utilization of dialkyl carbonates formed as by-products in a continuous process for the synthesis of oxalic acid esters from nitrous acid esters and carbon monoxide and wherein the esters are subsequently used as intermediates in the production of commercially useful products, such as ethylene glycol. The process comprises contacting a mixture containing the by-product comprised of a dialkyl carbonate with an aqueous solution of a metal carbonate under hydrolyzing conditions whereby the dialkyl carbonate is converted to the corresponding alkanol and the metal carbonate is converted to metal bicarbonate. Upon distillation of the alkanol from the mixture the bicarbonate is converted back to the metal carbonate which can then be recycled from the bottoms to the hydrolyzing zone for use in further hydrolysis of by-product. The alkanol is recycled for use in the continuous process.Type: GrantFiled: March 27, 1986Date of Patent: May 5, 1987Assignee: Union Carbide CorporationInventors: John W. Crandall, James E. Deitzler, Louis A. Kapicak, Fedor Poppelsdorf
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Patent number: 4661622Abstract: A novel method for producing a composite ester from dibasic acid, diol and monovalent alcohol through a dehydrating esterification reaction in the first step and then alcohol removing ester interchange reaction in the second step.Type: GrantFiled: January 31, 1986Date of Patent: April 28, 1987Inventor: Satoshi Matsumoto
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Patent number: 4658053Abstract: A process for the production of an ester comprises reacting an olefin with carbon monoxide, hydrogen and another ester at elevated temperature and pressure in the presence of a catalyst comprising (1) a rhodium source, (2) a ruthenium source, and (3) cobalt or zinc iodide. The product ester comprises the acid group of the ester used as reactant esterified with a hydrocarbyl group derived from the olefin, hydrogen and carbon monoxide.Type: GrantFiled: February 25, 1985Date of Patent: April 14, 1987Assignee: BP Chemicals LimitedInventor: Michael J. Green
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Patent number: 4645855Abstract: A process for the preparation of succinic acid diesters by carbonylation of acrylic acid esters in the presence of alcohols, using a cobalt carbonyl complex as the catalyst and a heterocyclic nitrogen base as the promoter, at 80.degree.-200.degree. C. and under a carbon monoxide pressure of 60-300 bar, wherein the reaction is carried out in the presence of not less than 20% by weight, based on the amount of all the liquid constituents of the reaction mixture, of an inert liquid and the concentration of the acrylic acid ester is kept, for the predominant part of the reaction time, at below 15% by weight, again based on the amount of all liquid constituents.Type: GrantFiled: August 24, 1984Date of Patent: February 24, 1987Assignee: BASF AktiengesellschaftInventors: Johannes G. Reuvers, Wolfgang Richter, Rudolf Kummer
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Patent number: 4642371Abstract: Preparation of a diester of a dicarboxylic acid by reacting an unsaturated hydrocarbon having two carbon atoms less than the dicarboxylic acid, carbon monoxide and a nitrite ester with a solvent in the presence of a catalyst system formed by combining (1) a Group VIII noble metal compound and (2) a vanadium salt and/or a titanium salt.Type: GrantFiled: May 14, 1986Date of Patent: February 10, 1987Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4642374Abstract: A process for the preparation of an ester of dicarboxylic acid from an alkene, carbon monoxide. The process is catalyzed by a catalyst which comprises a platinum group metal, for example palladium, and a copper compound. To avoid catalyst deactivation the process is carried out in the presence of a dihydrocarbyl peroxide which is reduced to a hydrocarbyl alcohol under the process conditions. The process can be used, for example, to prepare succinate esters from ethylene, carbon monoxide, an alcohol and a dihydrocarbyl peroxide such as di-tertiary butyl peroxide.Type: GrantFiled: December 17, 1985Date of Patent: February 10, 1987Assignee: The British Petroleum Company p.l.c.Inventors: Andrew R. Lucy, George E. Morris