Preparing Esters By Ester Interchange Patents (Class 560/234)
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Patent number: 5516776Abstract: A process and intermediates for the enantioselective synthesis of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid are disclosed.Type: GrantFiled: September 12, 1994Date of Patent: May 14, 1996Assignee: Eli Lilly and CompanyInventors: Charles J. Barnett, Thomas M. Wilson
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Patent number: 5481029Abstract: A process for preparing ketones, for example CF.sub.3 C(O)CH.sub.3, CF.sub.3 C(O)CH.sub.2 C(O)CF.sub.3 and CF.sub.3 C(O)CF.sub.2 H, in which .beta.-ketoesters are transesterified and decarboxylated using a carboxylic acid, for example trifluoroacetic acid, in the presence of a catalyst, particularly an "onium" salt of a carboxylic acid or an effective amount of a proton-donating acid, preferably a sulfonic acid such as alkyl- or arylsulfonic acids, or a mineral acid. The process is advantageously carried out in the absence of water, so that no formation of acetals or hydrates occurs, and no dehydrating step is needed. The process is simple to carry out, and if transesterification is carried out with a sufficiently active carboxylic acid, for example with trifluoroacetic acid, the presence of an additional catalyst is unnecessary.Type: GrantFiled: April 26, 1994Date of Patent: January 2, 1996Assignee: Solvay Fluor und Derivate GmbHInventors: Max Braun, Johannes Eicher, Werner Rudolph, Kerstin Eichholz
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Patent number: 5430178Abstract: Acetic ester is produced economically by a gas phase carbonylation of methanol with carbon monoxide followed by a transesterification. Specifically, the inventive process comprises (a) carbonylating methanol in a gas phase with carbon monoxide to produce a mixture of acetic acid and methyl acetate; (b) separating from the production mixture the acetic acid, and a mixture of the methyl acetate and the co-catalyst; (c) further separating said methyl acetate and the co-catalyst and recycling the separated co-catalyst to the carbonylation reactor; (d) introducing the separated methyl acetate into a lower region of a transesterification reactor at a temperature of above its boiling point; (e) introducing an C.sub.Type: GrantFiled: July 27, 1994Date of Patent: July 4, 1995Assignee: Korea Institute of Science and TechnologyInventors: Sung J. Uhm, Sung H. Han, Jun W. Oh, Oh S. Joo, Kwang D. Jung, Moon S. Lee
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Patent number: 5405992Abstract: A process for the continuous esterification of at least one alcohol and at least one carboxylic acid to form at least one ester and water, and the concurrent separation of the esterification products has been developed. The process uses a solid bed which as a catalyst for esterification and as an adsorbent for at least one of the products. The process preferably operates in the simulated moving bed mode. A specific embodiment of the invention is one where the simulated moving bed is a homogeneous mixture of at least one solid effective as an esterification catalyst and at least one solid effective as an ester or water adsorbent. Another specific embodiment is one where the simulated moving bed is a strongly acidic macroreticular polymeric resin effective both as an esterification catalyst and as an adsorbent for at least one esterification product.Type: GrantFiled: April 28, 1994Date of Patent: April 11, 1995Assignee: UOPInventors: Gregory A. Funk, James R. Lansbarkis, Ajay K. Chandhok
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Patent number: 5350879Abstract: Base-catalyzed transesterification may be effected in the presence of certain metal oxide solid solutions and layered double hydroxides as the basic catalyst. Use of the latter materials as the base catalyst readily permits one to conduct transesterification in a continuous manner. Such a continuous process is applicable to esters generally and is not limited to any particular structural types of esters or alcohols. Transesterification of detergent range alkyl acetates by this method leads to the formation of the corresponding detergent range alcohols in excellent yield and with quite high selectivity.Type: GrantFiled: November 17, 1993Date of Patent: September 27, 1994Assignee: UOPInventors: Dusan J. Engel, Thomas P. Malloy, Peter K. Nickl
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Patent number: 5254722Abstract: A process for the production of triglycerides of C.sub.1 -C.sub.4 alkyl esters of C.sub.6 -C.sub.22 fatty acids:a) where dry sodium carbonate catalyst is dissolved in glycerol and mixed with a molar excess of preferably the methyl ester of C.sub.6 -C.sub.22 fatty acid at a temperature between about 150.degree. C. and 250.degree. C. at less than atmospheric pressure and under substantially anhydrous conditions to produce an initial reaction mixture containing the corresponding triglycerides of said fatty acids, and partially reacted glycerol with unreacted hydroxyl groups (OH values 10-40),b) thereafter, a portion of the initial reaction mixture is reacted with additional C.sub.1 -C.sub.4 alkyl ester of C.sub.6 -C.sub.22 fatty acid under conditions to achieve substantially full conversion of said unreacted hydroxyl groups (OH values of 5 or less), andc) a product containing the corresponding triglycerides of said fatty acids is separated from unreacted alkyl ester and from the sodium carbonate catalyst.Type: GrantFiled: May 19, 1988Date of Patent: October 19, 1993Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Eberhard Peukert, Horst Rutzen, Gerhard Wollmann
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Patent number: 5225590Abstract: Intermediates and methods for producing intermediates for use in preparing 9-(1,3-dihydroxy-2-propoxymethyl)-guanine and esters and ethers thereof.Type: GrantFiled: April 26, 1988Date of Patent: July 6, 1993Assignee: Syntex (U.S.A.) Inc.Inventors: David J. Morgans, Jr., Harlan H. Chapman
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Patent number: 5183930Abstract: A process is described for preparing carboxylic acid esters via transestierification using a new heterogeneous, transition-metal transesterification catalyst of enhanced activity. The catalyst is prepared by an improved method of reacting a metal alkoxide to form an active species and absorbing the metal containing species onto a support. The method requires the controlled hydrolysis of a transition metal alkoxide to prepare an oligomer, which is then absorbed onto a hydroxylic support.Type: GrantFiled: June 17, 1992Date of Patent: February 2, 1993Assignee: Rohm and Haas CompanyInventors: Jeremia J. Venter, Christine McDade
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Patent number: 5149861Abstract: Trialkylamines and methyl formate are recovered from reaction mixtures obtained in the preparation of trimethylolalkanes by reaction of n-alkanals with from 2.2 to 4.5 moles of formaldehyde in aqueous solution in the presence of from 0.6 to 3 mole of trialkylamine, each quantity based on 1 mole of alkanal, and subsequent hydrogenation in a process wherein the crude reaction mixturea) is heated to from 100.degree. to 200.degree. C.Type: GrantFiled: March 1, 1991Date of Patent: September 22, 1992Assignee: BASF AktiengesellschaftInventors: Franz Merger, Peter Hettinger, Leopold Hupfer, Juergen Paetsch, Heribert Deck, Heinz Auer, Erwin Brunner
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Patent number: 5116546Abstract: The invention pertains to the production of high-purity fatty-acid lower-alkyl mono-esters which comprises a first transesterification step between glycerol fatty-acid esters and a lower alcohol, a separation step wherein the reaction product of the esterification step is separated into glycerol-rich and fatty-acid lower-alkyl mono-ester rich fractions, a second esterification step in which all glycerol and fatty-acid glycerolesters of the fatty-acid lower-alkyl mono-ester rich fraction are esterified to the corresponding fatty-acid triglycerolesters, and a recovery step wherein said fatty-acid lower-alkyl mono-esters are recovered.Type: GrantFiled: April 3, 1990Date of Patent: May 26, 1992Assignee: Van den Bergh Foods Co., Division of Conopco, Inc.Inventors: Robbert Klok, Herbert H. Verveer
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Patent number: 5093517Abstract: There is disclosed a method for making compounds such as 3,6,9-trioxaundecane-1,11-bis (3-n-dodecylthiopropionate) which comprises reacting an alkyl thiopropionate with a glycol at temperatures between 50.degree. C. and 180.degree. C. in the presence of a catalytic amount of a dialkyl tin oxide.Type: GrantFiled: March 9, 1987Date of Patent: March 3, 1992Assignee: The Goodyear Tire & Rubber CompanyInventors: Kirkwood S. Cottman, Joseph A. Kuczkowski
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Patent number: 5047583Abstract: A carboxylic acid of formula RCO.sub.2 H, for example acetic acid, is prepared from a formate ester of formula HCO.sub.2 R, for example methyl formate, by heating the ester at elevated temperature with an iridium catalyst, a halide promoter and a strong acid. The strong acid is one having a pKa of not greater than 0 in aqueous media for example a sulphonic acid. Addition of the strong acid to the reaction mixture causes an increase in the rate of conversion of formate ester to carboxylic acid.Type: GrantFiled: July 13, 1984Date of Patent: September 10, 1991Assignee: BP Chemicals LimitedInventor: Peter S. Williams
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Patent number: 4996357Abstract: Acetic acid is advantageously prepared from a starting material having a formic acid moiety and a methyl ester moiety by heating said starting material in the presence of (1) carbon monoxide, (2) at least one of (2-a) a metal accelerator selected from beryllium, a metal belonging to the group IIIA, IVB, VB, VIB or IIA of the Periodic Table, a lanthanide metal and an actinide metal and (2-b) an onium compound or a precursor for the onium compound, (3) a rhodium catalyst and (4) an iodine compound.Type: GrantFiled: March 29, 1985Date of Patent: February 26, 1991Assignee: Daicel Chemical Industries, Ltd.Inventors: Hidetaka Kojima, Takaaki Fujiwa
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Patent number: 4983757Abstract: Carboxylic acid esters and formamide are efficiently obtained for reacting carboxylic acid amides and formic acid esters, or carboxylic acid amides, alcohols and carbon monoxide in the presence of an alkaline earth metal oxide catalyst.Type: GrantFiled: March 28, 1990Date of Patent: January 8, 1991Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Jiro Ishikawa, Hirofumi Higuchi, Shuji Ebata, Koichi Kida
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Patent number: 4976892Abstract: A process for the continuous transesterification of C.sub.6 -C.sub.22 fatty acid lower alkyl esters, particularly methyl esters, with polyhydric C.sub.2 -C.sub.5 alcohols, particularly glycerol, in a reaction column comprising a rectifying and reaction section, alkaline catalysts and polyhydric alcohol are introduced into the upper part of the reaction column and boiling fatty acid methyl ester is introduced into the middle part of the reaction column. The product collected in the sump of the column is removed, heated and returned to the lower part of the reaction column. Product is removed from the sump. Lower alkanols passing from the reaction column section to the rectifying section are rectified. The reaction column is operated in boiling equilibrium in its lower part and predominantly in an absorption/desorption equilibrium in its upper part.Type: GrantFiled: March 14, 1989Date of Patent: December 11, 1990Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Lutz Jeromin, Eberhard Peukert, Bernhard Gutsche, Gerhard Wollmann, Bernard Schleper
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Patent number: 4960927Abstract: The invention relates to a process for the continuous preparation of acetates by a transesterification reaction in the homogeneous liquid phase in the presence of a catalyst selected from metallic alcoholates. The process comprises more particularly the introduction of the catalyst into a reactor (R) and the introduction of the reagents, comprised of an acetate (I) and an alcohol (II), into a distillation column (D1) surmounting the reactor (R) and operating at a pressure (P1) identical with that in (R). The acetate (III) formed is withdrawn from (R) mixed with the catalyst, which is separated and recycled in (R). An azeotropic mixture (M1), comprising the acetate (I) and the alcohol (IV) formed, emergences at the head of (D1) and feeds a distillation column (D2) at a pressure (P2) lower than (P1), so as to produce at the head of the column an azeotropic mixture (M2) depleted in alcohol (IV), the mixture being recycled in (D1).Type: GrantFiled: December 5, 1989Date of Patent: October 2, 1990Assignee: BP Chemicals LimitedInventors: Michel Canonge, Jean C. Joly
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Patent number: 4942254Abstract: Compositions containing sulfuric acid and one or more of certain chalcogen-containing compounds in which the chalcogen compound/H.sub.2 SO.sub.4 molar ratio is below 2 contain the mono-adduct of sulfuric acid which is catalytically active for promoting organic chemical reactions. Suitable chalcogen-containing compounds have the empirical formula. ##STR1## wherein X is a chalcogen, each of R.sub.1 and R.sub.2 is independently selected from hydrogen, NR.sub.3 R.sub.4, and NR.sub.5, at least one of R.sub.1 and R.sub.2 is other than hydrogen, each of R.sub.3 and R.sub.4 is hydrogen or a monovalent organic radical, and R.sub.5 is a divalent organic radical. Such compositions are useful for catalyzing organic reactions such as oxidation, oxidative addition, reduction, reductive addition, esterification, transesterification, hydrogenation, isomerication (including racemization of optical isomers), alkylation, polymerization, demetallization of organometallics, nitration, Friedel-Crafts reactions, and hydrolysis.Type: GrantFiled: January 29, 1988Date of Patent: July 17, 1990Assignee: Union Oil Company of CaliforniaInventor: Donald C. Young
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Patent number: 4942228Abstract: Polyol polyesters having reduced color content are prepared by base-catalyzed transesterification of pretreated lower (i.e., C.sub.1 -C.sub.3) alkyl fatty esters with polyols. The pretreatment comprises the steps of contacting the alkyl fatty esters (in a liquid state) with an alkoxide base, separating undissolved solids from the esters, and then distilling the esters.Type: GrantFiled: May 6, 1986Date of Patent: July 17, 1990Assignee: The Procter & Gamble CompanyInventor: Michael S. Gibson
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Patent number: 4927954Abstract: A continuous process for efficiently co-producing secondary alcohols of long-chain olefins and lower carboxylic acid esters, comprising (I) performing an acid/olefin reaction in the presence of a heterogeneous catalyst such as Amberlyst 15, and (II) performing an ester-exchange reaction in the presence of, e.g., titanium alcoholate. A desirable feature of the process is the ability to produce co-products of choice.Type: GrantFiled: April 19, 1989Date of Patent: May 22, 1990Assignee: Union Carbide Chemicals and Plastics Company, Inc.Inventors: Robert J. Knopf, Louis F. Theiling Jr., Leroy P. Berti
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Patent number: 4918226Abstract: A process for converting formic acid esters or transesterification products thereof to carboxylic acids comprising contacting a formic acid ester of the formula (HCOO).sub.n --R where R is aliphatic, cycloaliphatic or aralkyl and n is 1 or 2 with a catalytically effective amount of a soluble iridium salt and an iodide promoter at a temperature of from about 100.degree. C. to about 300.degree. C. in the presence of an organic solvent containing at least one carboxylic acid.Type: GrantFiled: June 22, 1981Date of Patent: April 17, 1990Assignee: Exxon Research and Engineering CompanyInventor: Roy L. Pruett
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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: 4681967Abstract: A process for the transesterification of a carboxylic or carbonic acid ester comprises reacting the carboxylic or carbonic acid ester under transesterification conditions with an alcohol in the presence, as catalyst, of either (i) a Group V element-containing Lewis base and an epoxide or (ii) a cyclic amidine.The Lewis base can be an organic compound containing trivalent phosphorus or nitrogen and can be an amine, for example an amidine.The process can be operated in the liquid phase at a temperature of from 15.degree. to 150.degree. C., and the catalyst is employed in solution.Preferred catalysts are those where the cyclic amidine forms part of a fused ring system containing six and five membered rings, six and seven membered rings or two six membered rings.Type: GrantFiled: August 23, 1985Date of Patent: July 21, 1987Assignee: BP Chemicals LimitedInventor: Michael J. Green
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Patent number: 4664851Abstract: Process for the co-production of carboxylic acids of the general formula R.sup.1 --COOH and R.sup.2 --COOH and carboxylic acid esters of the general formula R.sup.1 --COOCH.sub.2 R.sup.2 and R.sup.2 --COOCH.sub.2 R.sup.1 from carboxylic acid esters of the general formula R.sup.1 --COOR.sup.2 and/or ethers of the general formula R.sup.3 OR.sup.4 (R.sup.1, R.sup.2, R.sup.3, R.sup.4 representing (substituted) alkyl or (substituted) aryl, alkaryl or aralkyl, R.sup.1 also representing H), carbon monoxide and hydrogen at elevated temperature and pressure in the presence of a ruthenium compound, a further Group VIII metal compound, and a compound R.sup.5 Hal or R.sup.5 COHal where R.sup.5 has one of the meanings given for R.sup.2 and Hal is iodine or bromine, the reaction mixture being substantially free from other transistion metal or Group II metal iodides or bromides, and containing a trivalent nitrogen compound containing a group ##STR1## (X=O or S), such as an amide, a carbamate, a urea or a derivative thereof.Type: GrantFiled: July 19, 1982Date of Patent: May 12, 1987Assignee: Shell Oil CompanyInventor: Eit Drent
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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: 4665223Abstract: A process for the production of 1-alkoxyalkyl esters comprises reacting an unsaturated ester with an alcohol in the presence of a Lewis base containing catalyst. The Lewis base containing catalyst is preferably (i) an amidine, or (ii) a Lewis base and an epoxide or (iii) a trivalent organophosphorus compound in the presence of an activated alkene or alkyne. The process can be used to prepare, for example, 1-methoxyethyl acetate from vinyl acetate and methanol under mild conditions.Type: GrantFiled: January 15, 1985Date of Patent: May 12, 1987Assignee: BP Chemicals LimitedInventor: Michael J. Green
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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: 4652667Abstract: A process is provided for the transesterification of carbonate esters and carboxylic acid esters at elevated temperatures and in the presence of an effective amount of an amidine compound.Type: GrantFiled: January 18, 1985Date of Patent: March 24, 1987Assignee: BP Chemicals LimitedInventor: Michael J. Green
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Patent number: 4650896Abstract: 2-Alkyl-4,4-diacyloxybut-2-enals of the formula ##STR1## where R.sup.1 is alkyl and R.sup.2 is hydrogen or an aliphatic, cycloaliphatic or aromatic radical, are prepared by a process in which a 2-alkyl-1,4-diacyloxy-1,3-butadiene of the formula ##STR2## is reacted with oxygen or an oxygen donor in the presence of an acidic ion exchanger.Type: GrantFiled: May 3, 1985Date of Patent: March 17, 1987Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Joachim Paust
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Patent number: 4640802Abstract: Process for the co-production of carboxylic acids of the general formula R.sup.1 --COOH and R.sup.2 --COOH and carboxylic acid esters of the general formula R.sup.1 --COOCH.sub.2 R.sup.2 and R.sup.2 --COOCH.sub.2 R.sup.1 from carboxylic acid esters of the general formula R.sup.1 --COOR.sup.2 and/or ethers of the general formula R.sup.3 OR.sup.4 (R.sup.1, R.sup.2, R.sup.3, R.sup.4 representing (substituted) alkyl or (substituted) aryl, alkaryl or aralkyl, R.sup.1 also representing H), carbon monoxide and hydrogen at elevated temperature and pressure in the presence of a ruthenium compound, a further Group VIII metal compound, a phosphine oxide and a compound R.sup.5 Hal or R.sup.5 COHal where R.sup.5 has one of the meanings given for R.sup.2 and Hal is iodine or bromine, the reaction mixture being substantially free from other transition metal or Group II metal iodides or bromides, and containing a tertiary phosphine oxide.Type: GrantFiled: July 7, 1982Date of Patent: February 3, 1987Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4617281Abstract: A catalyst suitable for use in reactions catalyzed by strong base is provided. The catalyst comprises an organic compound containing a Group VA element for example an amine or phosphine supported on a solid which is insoluble in the reaction mixture. The catalyst may be activated by treatment with an epoxide. Catalysts in which the amine is an amidine or a guanidine are particularly effective.Type: GrantFiled: June 4, 1985Date of Patent: October 14, 1986Assignee: BP Chemicals LimitedInventor: Michael J. Green
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Patent number: 4608202Abstract: For the production of fatty acid esters of short-chain, aliphatic alcohols by the catalytic transesterification of natural fats and/or oils containing free fatty acids (oil phase) with the corresponding monoalcohols, the oil phase is subjected to preliminary esterification with the monoalcohols in the presence of acidic esterification catalysts at temperatures no higher than 120.degree. C. and under pressures no higher than 5 bars and in the presence of a liquid entraining agent substantially immiscible with the oil phase, after which the reaction product is separated into an entraining agent phase containing the acidic catalyst and water of reaction and the treated oil phase, the oil phase is then subjected to transesterification while the acidic catalyst-containing entraining agent phase is returned, after at least partial drying, to the preliminary esterification stage.Type: GrantFiled: April 11, 1984Date of Patent: August 26, 1986Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Herbert Lepper, Lothar Friesenhagen
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Patent number: 4559180Abstract: A process for the transesterification of a carboxylic or carbonic acid ester comprises reacting the carboxylic or carbonic acid ester under transesterification conditions with an alcohol in the presence, as catalyst, of either (i) a Group V element-containing Lewis base and an epoxide or (ii) a cyclic amidine.The Lewis base can be an organic compound containing trivalent phosphorus or nitrogen and can be an amine, for example an amidine.The process can be operated in the liquid phase at a temperature of from 15.degree. to 150.degree. C., and the catalyst is employed in solution.Preferred catalysts are those where the cyclic amidine forms part of a fused ring system containing six and five membered rings, six and seven membered rings or two six membered rings.Type: GrantFiled: November 15, 1983Date of Patent: December 17, 1985Assignee: BP Chemicals LimitedInventor: Michael J. Green
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Patent number: 4521342Abstract: 2-alkyl-4,4-diacyloxybut-2-enals of the formula ##STR1## where R.sup.1 is alkyl and R.sup.2 and R.sup.3 are each hydrogen or an aliphatic, cycloaliphatic or aromatic radical, are prepared by a process wherein a 2-alkyl-2,4-diacyloxybut-3-enal of the formula ##STR2## is treated with an aliphatic carboxylic acid.Type: GrantFiled: March 7, 1983Date of Patent: June 4, 1985Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Hans-Martin Weitz, Joachim Paust
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Patent number: 4512928Abstract: Adducts of tetrasubstituted pyrophosphato titanates and/or amines, having the formulaX.sub.c Ti[OP(O)(OR.sup.1)OP(O)(OR.sup.2)OR.sup.3)].sub.4-c(NR.sup.4 R.sup.5 R.sup.6)d[P(OR.sup.7)(OR.sup.8)(OR.sup.9)]e,are useful in improving the physical and chemical properties of many filled resins.Type: GrantFiled: June 21, 1983Date of Patent: April 23, 1985Assignee: Kenrich Petrochemicals, Inc.Inventors: Gerald Sugerman, Salvatore J. Monte
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Patent number: 4506105Abstract: A process for preparing cyclooctene-4-ol-1 with a content in excess of 70% by reacting cyclooctadiene-1,5 with formic acid and then saponifying or transesterifying the cyclooctenyl formate with an alcohol of low boiling point.In the absence of a catalyst, formic acid is reacted with cyclooctadiene-1,5 at 50.degree. to 200.degree. C., preferably 95.degree. to 105.degree. C. The reaction product without further processing is directly distilled, and the formic acid ester so obtained is transesterified with an alcohol of low boiling point into the formate of that alcohol and into cyclooctene-4-ol-1.Type: GrantFiled: August 4, 1983Date of Patent: March 19, 1985Assignee: Chemische Werke Huls AGInventor: Manfred Kaufhold
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Patent number: 4457868Abstract: A method for conducting transesterification reactions employing a catalyst system comprising metallic sodium and aluminum isopropoxide which provides a facile, high yield, means for producing compounds such as esters of alkyl- and alkyloxy-substituted arylamines.Type: GrantFiled: September 2, 1981Date of Patent: July 3, 1984Assignee: Mobil Oil CorporationInventor: Milton Braid
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Patent number: 4458088Abstract: A continuous process for the production of alkyl esters from carboxylic acids wherein an aqueous stream containing a first carboxylic acid, RCO.sub.2 H, is contacted with an organic stream comprising a carboxylic acid ester, R"CO.sub.2 R', so that the organic stream is enriched with RCO.sub.2 H. The RCO.sub.2 H enriched organic stream is separated from the aqueous stream and is contacted with a catalyst to obtain a second carboxylic acid, R"CO.sub.2 H, and a product carboxylic acid ester, RCO.sub.2 R'. The product ester, RCO.sub.2 R', is separated from the second acid, R"CO.sub.2 H, the reactant ester, R"CO.sub.2 R', and the first acid, RCO.sub.2 H, and the second acid, R"CO.sub.2 H, is esterified to obtain the reactant ester, R"CO.sub.2 R', which is recycled to the initial part of the process. In this process R is aliphatic or aromatic, R' is alkyl and R" is aliphatic with at least about 4 carbon atoms.Type: GrantFiled: April 1, 1982Date of Patent: July 3, 1984Assignee: The Standard Oil Company (Sohio)Inventors: Harley F. Hardman, John G. Frye, Jr., Terry J. Mazanec
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Patent number: 4442303Abstract: In one of its embodiments this invention provides a process for recovering C.sub.4 -C.sub.6 dicarboxylic acid components contained in a waste byproduct stream derived from a reaction system in which adipic acid is produced by nitric acid oxidation of cyclohexanone/cyclohexanol.An important aspect of the process is the esterification and extraction of the C.sub.4 -C.sub.6 dicarboxylic acids in the aqueous byproduct stream with a mixture of C.sub.1 -C.sub.3 alkanol and C.sub.6 -C.sub.20 alkanol, and the subsequent recovery of di(C.sub.6 -C.sub.20 alkyl) esters of succinic acid, glutaric acid and adipic acid.In a broader aspect this invention provides a process for recovery of water miscible organic acid components contained in an aqueous solution as C.sub.6 -C.sub.20 alkyl esters of the organic acids.Type: GrantFiled: December 9, 1980Date of Patent: April 10, 1984Assignee: El Paso Products CompanyInventor: Samuel S. Mims
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Patent number: 4435595Abstract: The present invention provides a process for the production of high purity methyl acetate from methanol and glacial acetic acid wherein the acetic acid functions both as a reactant and as an extractive agent. The process comprises countercurrently flowing approximately stoichiometric quantities of acetic acid and methanol through a single reactive distillation column in the presence of an acidic catalyst which is preferably sulfuric acid. The column provides intimate contact between the acetic acid and the methanol and between the acetic acid and the azeotropes (methyl acetate/water and methyl acetate/methanol) which are formed in the column. At preferred catalyst concentrations, the residence time in the column is at least about two hours. The process further comprises continuously removing high purity methyl acetate from the top of the column and continuously removing water from the bottom of the column.Type: GrantFiled: April 26, 1982Date of Patent: March 6, 1984Assignee: Eastman Kodak CompanyInventors: Victor H. Agreda, Lee R. Partin
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Patent number: 4431838Abstract: A C.sub.1 -C.sub.4 alkanol and its corresponding acetate or a C.sub.1 -C.sub.2 alkanol and its corresponding propionate are separated by extractive distillation utilizing an aromatic hydrocarbon as the extractive solvent. Transesterification of lower alkanols and lower alkyl acetates or propionates is effected by means of extractive distillation and the preparation of an intermediate ester of a higher boiling alcohol.Type: GrantFiled: February 8, 1982Date of Patent: February 14, 1984Assignee: National Distillers and Chemical CorporationInventors: Julian Feldman, John M. Hoyt
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Patent number: 4425277Abstract: A novel and effective catalyst system is provided for application in the preparation of alkenyl esters of carboxylic acids by transesterification reaction. The catalyst system consists of a palladium compound as the main ingredient and a cocatalyst formed of an alkali metal compound and a copper compound, at least one of which is a halide. The catalyst ingredients are adsorbed on a solid catalyst carrier, so that repeated use of the combined catalyst or a continuous operation of the reaction can easily be facilitated.Type: GrantFiled: July 30, 1979Date of Patent: January 10, 1984Assignee: Shin-Etsu Vinyl Acetate Co., Ltd.Inventors: Fumiaki Kawamoto, Shozo Tanaka, Yoshihiro Honma
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Patent number: 4415499Abstract: The invention relates to supported catalysts based on a palladium(II) salt and activated carbon, there being used, as the support material, activated carbon having an analytical SiO.sub.2 content of from 0.5 to 8% by weight. The catalysts according to the invention are used for reacting carboxylic acids with alkenyl esters of lower carboxylic acids.Type: GrantFiled: October 6, 1981Date of Patent: November 15, 1983Assignee: Wacker-Chemie GmbHInventors: Klaus Blum, Rudolf Strasser
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Patent number: 4410719Abstract: 2-Alkyl-4,4-diacyloxybut-2-enals of the formula ##STR1## where R.sup.1 is alkyl and R.sup.2 and R.sup.3 are each hydrogen or an aliphatic, cycloaliphatic or aromatic radical, are prepared by a process in which a 2-alkyl-1,4-diacyloxybuta-1,3-diene of the formula ##STR2## is reacted with oxygen or an oxygen donor, in the presence of a carboxylic acid of the formulaR.sup.3 -COOH III.Type: GrantFiled: June 29, 1982Date of Patent: October 18, 1983Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Hans-Martin Weitz, Joachim Paust
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Patent number: 4410718Abstract: Carboxylic acid-containing compounds are esterified by reacting at elevated temperatures with organic esters of trichloroacetic acid in the presence of an initiator.Type: GrantFiled: June 11, 1982Date of Patent: October 18, 1983Assignee: The Dow Chemical CompanyInventors: James M. Renga, Pen-Chung Wang
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Patent number: 4386036Abstract: Process for the preparation of vinylphosphonic acid, by heating a 2-acetoxyethanephosphonic acid dialkyl ester of the general formula ##STR1## wherein R denotes an alkyl group having 1-4 carbon atoms, in the presence of acid or basic catalysts at 150.degree. to 270.degree. C. with elimination of an alkyl acetate, and thereafter hydrolyzing the remaining reaction mixture with water at temperatures between 150.degree. and 230.degree. C. while simultaneously distilling off the alcohol formed.Type: GrantFiled: March 18, 1982Date of Patent: May 31, 1983Assignee: Hoechst AktiengesellschaftInventor: Hans-Jerg Kleiner
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Patent number: 4380636Abstract: Carboxylic acid-containing compounds are esterified by reacting at elevated temperatures with an organic ester of trichloroacetic acid and an electrophilic halide in the presence of an initiator.Type: GrantFiled: June 11, 1982Date of Patent: April 19, 1983Assignee: The Dow Chemical CompanyInventors: James M. Renga, Pen-Chung Wang
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Patent number: 4370491Abstract: A process for the preparation of acetic acid esters CH.sub.3 --CO--O--R.sup.1 (I, R.sup.1 =an organic radical other than methyl and ethyl) by alkali-catalyzed trans-esterification of an acetic acid ester CH.sub.3 --CO--O--R.sup.2 (II, R.sup.2 =methyl or ethyl) with an alcohol R.sup.1 --OH (III), accompanied by elimination of the alcohol R.sup.2 --OH (IV), wherein(a) the trans-esterification reaction is carried out in the middle section K.sub.M of a distillation column K, the alcohol III being fed as liquid into the upper zone and the ester II into the lower zone of K.sub.M,(b) the alkaline catalyst is introduced into the upper part K.sub.U of K,(c) the alcohol IV, or a mixture of IV and the ester II, is taken off the top of the column,(d) the mixture obtained from (c) (unless the alcohol IV alone is obtained) is separated in the column section K.sub.U or in a stripper column K.sub.S into IV and the azeotrope of II and IV, and the latter is recycled to the lower zone of K.sub.Type: GrantFiled: May 14, 1981Date of Patent: January 25, 1983Assignee: BASF AktiengesellschaftInventors: Kaspar Bott, Gerd Kaibel, Herwig Hoffmann, Rudolf Irnich, Eberhard Schaefer
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Patent number: 4346240Abstract: A novel class of heterogeneous catalysts, containing Group VIII transition metals in combination with alkali organic compounds is prepared, such as potassium naphthalene on ruthenium on carbon. The catalysts are useful as heterogeneous catalysts in the hydrogenation of carboxylic acid esters. A process for producing the materials is described. The catalysts permit the process of the hydrogenation of carboxylic acid esters to primary alcohols to be conducted with the ester in the liquid phase at a temperature not exceeding about 150.degree. C. with high selectivity. Catalysts of Group VIII transition metals and alkali metal on carbon are also useful in such processes.Type: GrantFiled: September 29, 1981Date of Patent: August 24, 1982Assignee: Allied CorporationInventors: Roger A. Grey, Guido P. Pez
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Patent number: 4338220Abstract: Adducts of tetrasubstituted pyrophosphato titanates and/or amines, having the formulaX.sub.c Ti[OP(O)(OR.sup.1)OP(O)(OR.sup.2)OR.sup.3)].sub.4-c(NR.sup.4 R.sup.5 R.sup.6)d[P(OR.sup.7)(OR.sup.8)(OR.sup.9)]e,are useful in improving the physical and chemical properties of many filled resins.Type: GrantFiled: January 12, 1981Date of Patent: July 6, 1982Assignee: Kenrich Petrochemicals, Inc.Inventors: Gerald Sugerman, Salvatore J. Monte
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Patent number: 4334061Abstract: A process for recovering polyol fatty acid polyesters from the crude reaction product in which it is produced by contacting with an aqueous washing medium in the presence of an emulsion decreasing organic solvent so that the alkali metal fatty acid soaps and the color-forming bodies are taken into the aqueous phase, and upon settling the phases are separated from each other.Type: GrantFiled: October 29, 1979Date of Patent: June 8, 1982Assignee: Ethyl CorporationInventor: Joseph A. Bossier, III