Preparing Esters By Ester Interchange Patents (Class 560/217)
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Patent number: 6011176Abstract: The use of organic, polymeric, anionic water-soluble flocculants for the phase separation of an organic-aqueous system which essentially comprises monomeric acrylates, diacrylates, (poly)ester acrylates or (poly)ether acrylates and unreacted residues of the carboxylic anhydrides, carboxylic acids or alcohols used for preparing the acrylates.Type: GrantFiled: January 29, 1999Date of Patent: January 4, 2000Assignee: BASF AktiengesellschaftInventors: Wolfgang Paulus, Matthias Geisendorfer
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Patent number: 6008404Abstract: The present invention relates to a process to prepare alkyl (meth)acrylate esters from corresponding alkyl/methacrylate esters using an alkali metal alkoxide as an ester interchange catalyst to produce an alkyl (meth)acrylate ester monomer product C ##STR1## The present invention further relates to the use of bromide and iodide salts as free radical polymerization inhibitors. The present invention further relates to the use of a noninterfering alcohol or polyol that prevents anionic polymerization reactions of reactant ester B and/or alkyl (meth)acrylate product C. The present invention further relates to a process for inhibiting polymerization of (meth)acrylates being synthesized in a transesterification or ester-ester interchange reaction system.Type: GrantFiled: August 11, 1998Date of Patent: December 28, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Timothy M. Miller, Narayanan Pondicherry, Louis E. Trapasso, Aaron van de Sande
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Patent number: 5827939Abstract: Use of at least one heteropolyacid H.sub.n A.sub.a D.sub.c O.sub.y.xH.sub.2 O where A is phosphorus, boron, silicon, germanium, tin, arsenic, antimony, copper, nickel, cobalt, iron, cerium, thorium, chromium and mixtures thereof; D is molybdenum, tungsten, vanadium and combinations thereof; a is 0.1-10; c is 6-18; n is the number of acidic hydrogens in the heteropolyacid and is a number above 1; y is the number of oxygens in the heteropolyacid and is a number of 10-70; and x is the number of moles of water of crystal-lisation and is a number of 0-40, as catalyst in the preparation of esters of unsaturated carboxylic acids by direct esterification of acids with alcohols or by transesterification, these reactions being carried out in the liquid phase.Type: GrantFiled: December 22, 1993Date of Patent: October 27, 1998Assignee: AtochemInventor: Eric Paumard
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Patent number: 5763644Abstract: An improved method for transesterification of acrylate and alkyl acrylate esters. The improved method comprises the use of at least one aromatic amine compound having no acidic or ionic groups. The improved inhibitor system enhances the reaction rate of the transesterification reaction while simultaneously maintaining adequate polymerization suppression. The reaction is catalyzed by a basic catalyst, and can be driven by the removal of alcohol as an alcohol/saturated hydrocarbon azeotrope.Type: GrantFiled: April 8, 1996Date of Patent: June 9, 1998Assignee: Aristech Chemical CorporationInventors: Jeffrey S. Salek, Joseph Pugach
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Patent number: 5606103Abstract: Methyl or ethyl esters of mono- and polycarboxylic acids are transesterified with alcohols and polyols by reaction in the presence of a catalytically effective amount of organotin catalyst, so that an alcohol or polyol carboxylic acid ester is formed, which is then washed with aqueous alkali having a pH bigger than about 13.2 so as to remove essentially all of the organotin catalyst, thereby permitting the recovery of the alcohol or polyol carboxylic acid ester essentially free of the organotin catalyst.Type: GrantFiled: December 28, 1995Date of Patent: February 25, 1997Assignee: CPS Chemical Company, Inc.Inventors: Louis E. Trapasso, Philip L. Meisel, Lee B. Meisel, Willy K. Chwang
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Patent number: 5583237Abstract: Described are 3,5-dimethyl-pentenyl-dihydro-2(3H)-furanone isomer mixtures defined according to the structure: ##STR1## wherein structure represents mixtures wherein in the mixture in each of the compounds, one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond, processes for preparing same and uses thereof in augmenting or enhancing the aroma of consumable materials including perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, hair preparations, fabric softeners, fabric softener articles, cosmetic powders and perfumed polymers). Also described is a process for preparing such 3,5-dimethyl-pentenyl-dihydro-2(3H)-furanone isomer mixtures using as a starting material 2,7-octadienol having the structure: ##STR2## as well as the process intermediates having the structures: ##STR3## wherein R represents C.sub.1 -C.sub.4 alkyl; R.sub.1 and R.sub.Type: GrantFiled: February 26, 1996Date of Patent: December 10, 1996Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, William J. Fylak, Marie R. Hanna, Futoshi Fujioka
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Patent number: 5578740Abstract: Epoxy-containing compounds which are essentially free of organic halides are prepared by (I) reacting an allyl derivative of an active hydrogen-containing compound with (II) a peroxygen-containing compound. The epoxy-containing compounds are useful in coatings, castings, laminates etc.Type: GrantFiled: December 23, 1994Date of Patent: November 26, 1996Assignee: The Dow Chemical CompanyInventors: Andrew T. Au, J. Lowell Nafziger
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Patent number: 5557007Abstract: Novel unsaturated polylactone acrylates are produced by the reaction of an unsaturated polylactone, such as that produced in the reaction of a lactone with tetrahydrobenzyl alcohol, and a lower-alkyl acrylate under transesterification conditions. The unsaturated polylactone acrylate product may be subsequently epoxidized to form novel 3,4-epoxy polylactone acrylates.Type: GrantFiled: September 28, 1990Date of Patent: September 17, 1996Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: James P. Stanley
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Patent number: 5498751Abstract: Esters of monocarboxylic acids are transesterified with 1,2- and 1,3-polyols by reaction in the presence of a catalytically effective amount of a dialkyltin oxide blended with an excess of dialkyltin dichloride, so that a polyol ester of the monocarboxylic acid is formed. A transesterification reaction of alcohols and polyols with methyl or ethyl mono- or polycarboxylic acid esters utilizing a dimethyltin catalyst is also disclosed, in which the alcohol or polyol carboxylic acid ester formed is essentially free of the organotin catalyst. Carboxylic acid esters produced by the described methods, as well as carboxylic acid esters that are free of organotin catalysts are also disclosed.Type: GrantFiled: September 3, 1993Date of Patent: March 12, 1996Assignee: CPS Chemical Company, Inc.Inventors: Louis E. Trapasso, Stanley J. Padegimas, Peter F. Epstein, Paul L. K. Hung, Purnendu Mukhopadhyay, Philip L. Meisel
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Patent number: 5362904Abstract: This invention relates to a process for the preparation of esters of acrylic or methacrylic acid with alcohols. The process comprises reacting the preformed ester of a C.sub.1 -C.sub.4 monohydric alcohol having only one oxygen function under transesterification conditions with a second alcohol having at least two carbon atoms and at least two oxygen functions in the presence of a catalyst comprising (a) an oxide, hydroxide or nitrate of calcium or barium and (b) a lithium compound LiX wherein X is nitrate, sulphite or carboxylate having more than six carbon atoms such that both (a) and (b) are not nitrate in the same catalyst.Type: GrantFiled: September 24, 1992Date of Patent: November 8, 1994Assignee: International Speciality Chemicals LimitedInventor: Mark A. Kearns
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Patent number: 5223621Abstract: Transvinylation process between vinyl acetate or vinyl propionate and a carboxylic acid of general formula (I),RCOOH (I)in which R represents a substituted or non-substituted alkyl, cycloalkyl, aralkyl or aromatic radical, in the presence of a palladium catalyst, in which the catalyst is obtained in situ, by reacting, in the reaction medium, a derivative of palladium chosen from the group constituted by palladium II acetate, nitrate or hydroxide and palladium deposited on charcoal, with a tertiary amine chosen from the group constituted by 2,2'-bipyridyl, orthophenanthroline or tetramethylethylenediamine, that the quantity of palladium used, expressed in gram-atom of palladium II per 100 moles of carboxylic acid of general formula (I) is between 0.005 and 1 and that the quantity of amine is greater than 1 and less than 10 moles per gram-atom of palladium II used and use for the preparation of certain products.Type: GrantFiled: January 6, 1992Date of Patent: June 29, 1993Assignee: Societe Francaise HoechstInventors: Jean-Claude Vallejos, Yani Christidis
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Patent number: 5210207Abstract: The invention provides an improved process for the preparation of a vinyl derivative of a Bronsted acid, wherein a vinyl derivative of a first Bronsted acid is subjected to transvinylation by reactive distillation with a second Bronsted acid.Type: GrantFiled: January 31, 1991Date of Patent: May 11, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Morteza Mokhtarzadeh, Rex E. Murray
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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: 5157090Abstract: Glycerol derivatives of general formula (I) ##STR1## in which R=allyl, methylallyl, acryloyl or methacryloyl, R.sub.1 =R.sub.2 =glyoxyloyl, R.sub.1, R.sub.2 =H, glyoxyloyl; their preparation process, their use as cross-linking agnets and cross-linking or cross-linkable compositions containing them. These compounds are useful as crosslinking agents for woven and non-woven fibrous mats and textiles.Type: GrantFiled: October 21, 1991Date of Patent: October 20, 1992Assignee: Societe Francaise HoechstInventors: Didier Wilhelm, Fernand Cuirassier, Alain Blanc
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Patent number: 5145989Abstract: Black acid or the sulfuric acid residue obtained in the manufacture of ethyl acrylate by reaction of ethylene and acrylic acid in the presence of sulfuric acid is heated and distilled in the presence of a solvent for recovery of acrylic acid and ethyl acrylate.Type: GrantFiled: July 14, 1987Date of Patent: September 8, 1992Assignee: Hoechst Celanese CorporationInventors: Edward F. Dougherty, Paul James L.
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Patent number: 5093490Abstract: The invention relates to a process for the production of (+)-bicyclo[3.3.0]octan-3-one-2 carboxylic acid steroid esters of formula I ##STR1## in which X means oxygen or the radicals --O--(CH.sub.2).sub.n --O-- or --O--CH.sub.2 --C(CH.sub.3).sub.2 --CH.sub.2 --O--,n means 2 or 3R.sub.2 means hydrogen or methyl,Y means the radicals X or X.sub.1,X.sub.1 means the radicals OCH.sub.3 or OCOR.sub.3,R.sub.3 means methyl, ethyl, phenyl, benzyl or pivalyl and the radical ##STR2## the radicals ##STR3## and X and X.sub.1 have the meanings indicated above, characterized in that D,L-bicyclo[3.3.0]octan-3-one-2 carboxylic acid esters of formula II ##STR4## in which X has the meaning indicated above and R is an alkyl group with 1-4 carbon atoms, with optically active steroids with a free 17'beta hydroxy group of formula III ##STR5## in which R.sub.Type: GrantFiled: November 13, 1989Date of Patent: March 3, 1992Assignee: Schering AktiengesellschaftInventor: Helmut Vorbrueggen
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Patent number: 5072027Abstract: In a process for producing a methacrylic acid ester by subjecting methyl methacrylate and an alcohol to a transesterification reaction in the presence of a catalyst and a polymerization inhibitor, the filtration time of catalyst and the like can be shortened by making a total water content in the catalyst, alcohol and methyl methacrylate 1000 ppm or less, or the generation of large bubbles during the reaction can be prevented by adding the starting alcohol to the reaction system at the alcohol conversion of 40% or more, or high catalytic activity is obtained even if a secondary or tertiary alcohol is used as a starting material by using as a catalyst that obtained by drying lithium hydroxide monohydrate with heating, these effects being also obtained by combining individual conditions.Type: GrantFiled: October 4, 1989Date of Patent: December 10, 1991Assignee: Hitachi Chemical Company, Ltd.Inventors: Akihiro Kobayashi, Toshio Akima, Takayuki Saito, Toshiyuki Fujita
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Patent number: 5066829Abstract: A process for the preparation of higher alkyl acrylic acid esters which comprises the addition reaction of olefins to alkyl acrylic acid esters catalyzed by tantalum pentachloride.Type: GrantFiled: April 17, 1990Date of Patent: November 19, 1991Assignee: Shell Oil CompanyInventors: Herbert E. Fried, Thomas H. Johnson
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Patent number: 5037978Abstract: An ester of a carboxylic acid is prepared via a transesterification reaction which comprises reacting a lower alkyl ester of carboxylic acid with a higher alkyl alcohol in the presence of a catalyst consisting of a hafnium chelate derived from hafnium tetrachloride, bis(alkoxide)hafnium dichlorides, or hafnium tetraalkoxides in the presence of 1,3-dicarbonyl compounds.Type: GrantFiled: March 12, 1990Date of Patent: August 6, 1991Assignee: Rohm and Haas CompanyInventor: Mario G. L. Mirabelli
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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: 4983761Abstract: A method of preparing high-boiling acrylates and methacrylates with low color indices by means of the transesterification of methyl acrylate and methacrylate with polyvalent alcohols is known ways which is characterized in that the product is subjected, after the separation of the catalyst, to a short-path evaporation at a bottom temperature of 110.degree. to 170.degree. C. and a pressure of 0.01 to 10 mbar.Type: GrantFiled: October 5, 1989Date of Patent: January 8, 1991Assignee: Degussa AktiengesellschaftInventors: Siegfried Breuer, Heinz Delle, Udo Ruldolph
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Patent number: 4981973Abstract: A process for the transvinylation of a vinyl derivative of a Bronsted acid with a different Bronsted acid which comprises providing a liquid phase mixture containing said vinyl derivative and said Bronsted acid in the presence of a ruthenium compound at a temperature at which transvinylation occurs and recovering as a product of transvinylation the vinyl derivative of the different Bronsted acid. The process is most favorably employed using carboxylic acids to make vinyl esters of carboxylic acids.Type: GrantFiled: June 30, 1988Date of Patent: January 1, 1991Assignee: Union Carbide Chemicals and Plastics Company, Inc.Inventor: Rex E. Murray
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Patent number: 4916255Abstract: Methacrylate esters of alcohols having an ether linkage and/or an alicyclic ring can be obtained with no trouble of coloration or polymer formation during the production and for the product. An alcohol having an ether linkage and/or an alicyclic ring is treated with an alkaline substance, and the treated alcohol is caused to react with methyl methacrylate for a transesterification reaction in the presence of an alkaline substance.Type: GrantFiled: May 16, 1988Date of Patent: April 10, 1990Assignee: Hitachi, Ltd.Inventors: Akihiro Kobayashi, Toshiyuki Fujita, Takayuki Saito, Toshio Akima
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Patent number: 4895976Abstract: Isomerization of 3-pentenoate esters to 4-pentenoate esters using homogeneous or heterogeneous catalysts of zero valent nickel complexes with an acid promoter.Type: GrantFiled: May 23, 1988Date of Patent: January 23, 1990Assignee: E. I. Du Pont de Nemours and CompanyInventors: Patrick M. Burke, Norman Herron, Stephan J. McLain
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Patent number: 4894430Abstract: The present invention is directed to polyester polyols in the hydroxyl number range of about 80 to 250 which are based on reaction products of(a) about 52 to 60 mole % of a polyol component with(b) about 40 to 48 mole % of dicarboxylic acid component, characterized in that(a) the polyol component is based on (i) about 2 to 30 mole % of at least one dihydric aliphatic alcohol which has at least two carbon atoms and is different from neopentyl glycol, (ii) about 5 to 40 mole % of at least one aliphatic alcohol which is at least trihydric and has at least 3 carbon atoms, (iii) about 20 to 60 mole % of bis-(hydroxymethyl)-cyclohexane and (iv) about 10 to 50 mole % of neopentyl glycol, and(b) the dicarboxylic acid component is based on (v) about 50 to 99 mole % of at least one aliphatic, saturated dicarboxylic acid or an anhydride of such an acid containing at least 2 carbon atoms and (vi) about 0.Type: GrantFiled: November 30, 1988Date of Patent: January 16, 1990Assignee: Bayer AktiengesellschaftInventors: Peter Hohlein, Hans-Joachim Hofer, Josef Pedain, Manfred Schonfelder
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Patent number: 4851568Abstract: Process for the manufacture of dialkylaminoalkyl (meth)acrylates (I) of formula:H.sub.2 C.dbd.C(R.sub.1)-C(O)-O-A-N(R.sub.2)(R.sub.3)R.sub.1 being a hydrogen atom or a methyl radical, A being a linear or branched alkyl radical containing 1 to 5 carbon atoms, and R.sub.2 and R.sub.3, which are identical or different from each other, are an alkyl radical containing 1 to 5 carbon atoms, or an aryl group, or R.sub.2 and R.sub.3 form a cyclic alkyl radical, in which ethyl (meth)acrylate is reacted with an aminoalcohol (II) of formula (R.sub.3)(R.sub.2)N-A-OH, A being a linear or branched alkyl radical containing 1 to 5 carbon atoms, in the presence of a polymerization inhibitor, at a temperature of between 20.degree. and 120.degree. C. and at a pressure equal to or lower than atmospheric pressure, in a molar ratio of ethyl (meth)acrylate to aminoalcohol (II) of between 1.Type: GrantFiled: July 8, 1988Date of Patent: July 25, 1989Assignee: NorsolorInventors: Patrice Hurtel, Charles Hazan, Francois de Champs, Jean-Michel Pau
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Patent number: 4814493Abstract: This invention describes an improved process for the production of C.sub.1 -C.sub.8 alkyl acrylate by the reaction of a C.sub.1 -C.sub.8 alkyl alcohol with acrylic acid in the presence of esterification catalysts and soluble manganese or cerium ions.Type: GrantFiled: July 5, 1983Date of Patent: March 21, 1989Assignee: Hoechst Celanese CorporationInventors: Edward F. Dougherty, Mark O. Scates, James L. Paul
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Patent number: 4791221Abstract: Methyl methacrylate is efficiently transesterified with a heavy alcohol in the presence of (i) defined amounts of a lithium catalyst incrementally added to the reaction medium, and (ii) an azeotrope-forming compound which forms, together with the methanol produced, an azeotrope distilling at a temperature of less than about 60.degree. C.Type: GrantFiled: July 11, 1986Date of Patent: December 13, 1988Assignee: Francaise d'Organo SyntheseInventor: Philippe Gabillet
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Patent number: 4745213Abstract: A method of preparing an ester of (meth)acrylic acid by transesterification with an alcohol, comprising, reacting a (meth)acrylic acid ester formed from an alcohol of 1 to 4 carbon atoms with a transesterifying alcohol, which is not a polybasic alcohol and which is different from the alcohol portion of said (meth)acrylic acid ester, in the presence of a catalyst system comprised of compounds A+B, wherein compound A is Li.sub.n Y, wherein Y is a halide, chlorate, carbonate, carboxylate of 1 to 6 carbon atoms, an alkoxide of 1 to 4 carbon atoms, hydroxide or oxide, and n is 1 or 2, depending on the valence of Y; and compound B is CaX.sub.q, wherein X is oxide or chloride and q is 1 or 2, depending on the valence of X, with the provision that at least one of the two anionic components Y and X is oxygen-containing.Type: GrantFiled: June 17, 1985Date of Patent: May 17, 1988Assignee: Rohm GmbH Chemische FabrikInventors: Fritz Schlosser, Peter J. Arndt, Manfred Mueller, Lothar Janssen
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Patent number: 4740613Abstract: 4-Pentenoates of the formula ##STR1## where R is alkyl of from 1 to 6 carbon atoms, are prepared by a process in which 5-methylbutyrolactone of the formula ##STR2## is reacted with an alcohol of the formulaR--O--H III,where R has the above meaning, at from 150.degree. to 400.degree. C. in the presence of an acidic catalyst.Type: GrantFiled: March 11, 1987Date of Patent: April 26, 1988Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Uwe Vagi
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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: 4672105Abstract: A method for preparing an ester of (meth)acrylic acid with a polyhydric alcohol comprising, transesterifying a (meth)acrylic acid ester derived from an alcohol of 1-4 carbon atoms with a transesterifying polyhydric alcohol in the presence of at least one metal compound catalyst system, said catalyst system being comprised of compounds A or a combination of compounds A+B, wherein A represents at least one compound of the formula: Li.sub.n Y, wherein Y is halide, chlorate, carbonate, carboxylate of 1 to 6 carbon atoms, an alkoxide of 1 to 4 carbon atom, hydroxide or oxide and n is 1 or 2, and wherein B is the compound: CaX.sub.q, wherein X is oxide or chloride, and q is 1 or 2; with the provision that at least one of the two anionic components Y and X is oxygen-containing.Type: GrantFiled: June 17, 1985Date of Patent: June 9, 1987Assignee: Rohm GmbH Chemische FabrikInventors: Fritz Schlosser, Peter J. Arndt, Manfred Mueller, Lothar Janssen
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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: 4613680Abstract: Angelic acid or esters thereof which are useful as perfume materials are prepared by isomerizing tiglic acid or an ester thereof with an organic sulfinic acid as the catalyst, and novel esters of angelic acid represented by the formula ##STR1## wherein R represents 3-hexenyl, 3-methyl-2-butenyl, 3-methyl-3-butenyl, 3-methyl-2-pentenyl, 3-methyl-4-pentenyl, CH.sub.3 (CH.sub.2).sub.l - (in which l is an integer from 5 to 9), cyclopentyl, cyclohexyl, 2-methylpentyl, .alpha.-methylbenzyl, neryl or furfuryl are provided as part of said esters of angelic acid.Type: GrantFiled: February 24, 1984Date of Patent: September 23, 1986Assignee: Toray Industries, Inc.Inventors: Masanobu Naruto, Hisao Kondo, Go Hata
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Patent number: 4609755Abstract: An ester interchange process, preferably for the formation of vinyl higher esters from methyl acrylate or methacrylate, is conducted in the presence of a novel alcoholate of the formula[M.sup.1 (OR.sup.4).sub.2-a R.sub.a.sup.6 ].sub.x [M.sup.2 (OR.sup.4).sub.n-b R.sub.b.sup.6 ].sub.y IwhereinM.sup.1 is selected from Mg, Ca and BaM.sup.2 is selected from Ti, Zr and Aln is 3 or 4 and is the valency of M.sup.2a is a number from 0 to 1.5b is a number from 0 to 0.75nx+Y=1 and each is a number from 0.005 to 0.995 and is such that the compound is liquid at 30.degree.0 C.R.sup.4 is selected from alkyl having at least 4 carbon atoms, cycloalkyl having at least 4 carbon atoms and aminoalkyl, andeach group R.sup.6 is individually selected from C.sub.1-3 alkoxy and blocking groups that are substantially less reactive in the ester interchange reaction than the groups OR.sup.4.Type: GrantFiled: April 15, 1985Date of Patent: September 2, 1986Assignee: Allied Colloids LimitedInventor: David Farrar
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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: 4556728Abstract: A substantially anhydrous mixture of methanol with an organic compound with which it forms an azeotrope can be separated by dissolving into the mixture lithium chloride or other suitable salt that forms a complex with methanol so as to form a homogeneous mixture, adding an organic solvent that is miscible with the organic compound but immiscible with the complex and thereby forming a heterogeneous mixture, and separating the phases. The methanol can be recovered from one phase and the organic compound from the other. The organic compound may typically be methyl acrylate or methacrylate, the blend being, for instance, obtainable during the transesterification of methyl (meth)acrylate with an alcohol to form a higher boiling ester such as dimethylaminoethyl (meth)acrylate or 2-ethylhexyl acrylate.Type: GrantFiled: November 28, 1984Date of Patent: December 3, 1985Assignee: Allied Colloids LimitedInventors: David Farrar, Gerald P. Benn
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Patent number: 4543422Abstract: A vinyl ester of the formula R.sup.3 COOR.sup.4 where R.sup.3 is CH.sub.2 .dbd.CH-- or CH.sub.2 .dbd.C.CH.sub.3 -- and R.sup.4 contains at least four carbon atoms and is selected from alkyl, cycloalkyl and aminoalkyl is conducted by reaction of an ester R.sup.3 COOR.sup.1, where R.sup.1 is C.sub.1-3 alkyl, with metal alcoholate formed from an alcohol R.sup.4 OH and titanium, aluminum, zirconium, calcium or magnesium in the absence of water or reactive alcohol.Type: GrantFiled: October 20, 1983Date of Patent: September 24, 1985Assignee: Allied Colloids LimitedInventor: David Farrar
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Patent number: 4500727Abstract: A process for producing methyl lactate by (I) hydroformylating vinyl acetate or vinyl propionate with a gaseous mixture of hydrogen and carbon monoxide in an organic solvent in the presence of a substantially water-insoluble rhodium complex and a tri-substituted phosphine to form .alpha.-acetoxy- or propionyloxy-propionaldehyde, (II) subjecting at least part of the reaction mixture obtained in step (I) to extraction with an aqueous medium to obtain an aqueous layer containing .alpha.-acetoxy- or propionyloxy-propionaldehyde and an extraction residue containing the catalyst components, and recycling the extraction residue to the hydroformylation step (I), (III) separating .alpha.-acetoxy- or propionyloxy-propionaldehyde from the aqueous layer containing the same as obtained in step (II), (IV) oxidizing .alpha.-acetoxy- or propionyloxy-propionaldehyde obtained in step (III) in the liquid phase with oxygen gas or an oxygen-containing gas in the presence of an oxidation catalyst to form .alpha.Type: GrantFiled: March 18, 1982Date of Patent: February 19, 1985Assignee: Kuraray Co., Ltd.Inventors: Takanori Kitamura, Mitsuo Matsumoto, Masuhiko Tamura
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Patent number: 4468521Abstract: Novel .gamma.-lactone derivatives are provided. These lactone derivatives, when reacted with hydrogen halide in alcohol, yield .gamma.-halogeno-.delta.-unsaturated carboxylic acid esters. This ring-opening process is useful for the purpose of increasing the yield of pyrethrin analogs which are of value as insecticides and agricultural chemicals. Thus, the .gamma.-lactone derivatives by-produced in the production process for dihalogenovinyl chrysanthemumates are caused to undergo ring-opening reaction to yield the corresponding .gamma.-halogeno-.delta.-unsaturated carboxylic acid esters which are important intermediates for said pyrethrin analogs.Type: GrantFiled: February 22, 1982Date of Patent: August 28, 1984Assignee: Kuraray Co., Ltd.Inventors: Mori Fumio, Omura Toshiaki, Nishida Takashi, Itoi Kazuo
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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: 4458090Abstract: Novel .gamma.-lactone derivatives are provided. These lactone derivatives, when reacted with hydrogen halide in alcohol, yield .gamma.-halogeno-.delta.-unsaturated carboxylic acid esters. This ring-opening process is useful for the purpose of increasing the yield of pyrethrin analogs which are of value as insecticides and agricultural chemicals. Thus, the .gamma.-lactone derivatives by-produced in the production process for dihalogenovinyl chrysanthemumates are caused to undergo ring-opening reaction to yield the corresponding .gamma.-halogeno-.delta.-unsaturated carboxylic acid esters which are important intermediates for said pyrethrin analogs.Type: GrantFiled: October 15, 1981Date of Patent: July 3, 1984Assignee: Kuraray Co., Ltd.Inventors: Mori Fumio, Omura Yoshiaki, Nishida Takashi, Itoi Kazuo
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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: 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: 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: 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: 4301297Abstract: Dimethylaminoethyl methacrylate, which is a useful monomer for the production of polymers useful as flocculants, antistatic agents, soil improving agents, etc., having a high purity can be prepared in a high yield by subjecting methyl methacrylate and dimethylaminoethanol to transesterification in the presence of di-n-octyltin oxide as a catalyst.Type: GrantFiled: November 4, 1977Date of Patent: November 17, 1981Assignee: Nitto Chemical Industry Co., Ltd.Inventors: Yoshiya Kametani, Yasuo Iino
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Patent number: 4293674Abstract: Compound of the formula CH.sub.2 .dbd.C(CH.sub.3)CO.sub.2 R wherein R is an alkadienyl or cycloalkadienyl group which contains the 1,3- or 1,4-diene carbon skeleton, homopolymers and copolymers of the compound, and curable finishes containing the homopolymer and/or copolymer.Type: GrantFiled: June 3, 1980Date of Patent: October 6, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventor: Gerald D. Andrews
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Patent number: 4281175Abstract: Methyl methacrylate is transesterified with dimethylaminoethanol using alkyltin compounds as catalysts. Typical alkyltin compounds used are tetrabutyltin, trioctyltin ethoxide, dibutyltin dimethoxide, dibutyltin dihydride, dibutyltin dilaurate, dibutyltin maleate, bis(tributyltin) oxide and bis(dibutylmethoxytin) oxide.Type: GrantFiled: June 17, 1980Date of Patent: July 28, 1981Assignee: Nitto Chemical Industry Co., Ltd.Inventors: Yoshiya Kametani, Yasuo Iino