Preparing Esters By Ester Interchange Patents (Class 560/217)
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Publication number: 20110046399Abstract: A process for preparing a hydroxyacid or hydroxyester from a reactant selected from (a) a carboxylic acid having an aldehyde or keto group; and (b) an ester of a carboxylic acid having an aldehyde or keto group; by contacting the reactant with a metal catalyst in the presence of hydrogen, wherein the metal catalyst is supported on a titanium dioxide or zirconium dioxide support.Type: ApplicationFiled: August 5, 2010Publication date: February 24, 2011Inventors: Rene Johan Haan, Jean-Paul Lange
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Publication number: 20100298594Abstract: A method and apparatus for preparing a N,N-dialkylaminoalkyl acrytate in a continuous transesterification reaction. The reaction involves adding alkyl acrylates such as methacrylate or ethacrylate to a reboiler mechanism and efficiently removing alcohol co-products. Because the reaction is continuous, the alkyl acrylates can be added as needed to increase output, decrease output, or fine-tune the reaction dynamics. An entrainer is used to form a volatile azeotrope which contains both alcohol and entrainer and which is easily removed from the reboiler mechanism. This method reduces the amount of entrainer needed per unit of alkyl acrylate used and eliminates any need to purify the end product from entrainer contamination of the resulting N,N-dialkylaminoalkyl acrylate product.Type: ApplicationFiled: May 19, 2009Publication date: November 25, 2010Inventors: Larry E. Brammer, JR., Barbara E. Fair, Cheng-Sung Huang, Linh Quach, Peter E. Reed, Leonard M. Ver Vers
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Patent number: 7781610Abstract: Supported heterogeneous organotin catalysts of the formula X1, X2, or X3: wherein Z is a spacer group; Y is an insoluble phenyl-group containing copolymer; R1, R2, R3, R5, and R6 are independently selected from halogen, alkyl, alkylene, phenyl, vinyl, allyl, naphthyl, aralkyl, and Z; and R4 is alkyl, alkylene, phenyl, vinyl, allyl, naphthyl, or aralkyl.Type: GrantFiled: February 19, 2010Date of Patent: August 24, 2010Assignee: Chemtura CorporationInventors: Uwe Schneider, Bernard Jousseaume, Karine Darriet, Thierry Toupance
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Publication number: 20100204509Abstract: The present invention relates to a process for preparing (meth)acrylates, which comprises the transesterification of an alcohol with a low-boiling ester of (meth)acrylic acid in the presence of catalysts, with the alcohol liberated from the low-boiling ester of (meth)acrylic acid being separated off by distillation, characterized in that the molar ratio of low-boiling ester of (meth)acrylic acid to starting alcohol present in the reaction mixture is increased during the reaction by addition of low-boiling ester of (meth)acrylic acid. The process of the invention makes a particularly inexpensive preparation of (meth)acrylates having a very high purity possible.Type: ApplicationFiled: May 8, 2008Publication date: August 12, 2010Applicant: EVONIK ROEHM GMBHInventors: Guido Protzmann, Harald Trauthwein, Joachim Knebel, Thorben Schuetz, Gerhard Koelbl, Thomas Kehr, Guenther Lauster
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Publication number: 20100145092Abstract: The subject of the invention is a method for the synthesis of (meth)acrylic esters by transesterification in the presence of a catalyst corresponding to the formula [(R?O)3TiO]xR? in which R? is a linear or branched alkyl radical having from 2 to 8 carbon atoms which may contain heteroatoms or R? is a phenyl radical, R? is a polyfunctional radical, originating from a polyol R?(OH)x comprising x alcohol functional groups and x is an integer ranging from 2 to 6. The method according to the invention is particularly well suited to the synthesis of dialkylaminoalkyl (meth)acrylates from methyl (meth)acrylate and a dialkylaminoalcohol.Type: ApplicationFiled: November 30, 2007Publication date: June 10, 2010Applicant: Arkema FranceInventor: Jean-Michel Paul
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Patent number: 7696376Abstract: A method for the manufacture of an ester by transesterification allows the transesterification reaction to proceed within a short reaction time and under a pressure of the order of normal pressure. It was found that transesterification proceeds when a starting material ester and an alcohol are brought into contact with a catalyst comprising (A) an amorphous zirconium oxide and (B) an oxide of a Group II element, an oxide of a Group V element, and/or an oxide of a Group IV element other than zirconium and hafnium. In this method, it is preferred that the starting material ester in a liquid-phase state and the alcohol in a vapor-phase state be brought into contact with a solid acid catalyst comprising the above components (A) and (B), the starting material ester be an oil or fat, and the alcohol be methanol or ethanol. An oxide of titanium, silicon, germanium, or tin is the preferred oxide of the Group IV element other than zirconium and hafnium.Type: GrantFiled: June 23, 2004Date of Patent: April 13, 2010Assignee: Japan Energy CorporationInventor: Satoshi Furuta
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Patent number: 7544830Abstract: In one embodiment, the method comprises: combining liquid biomass with an alcohol to form a combined liquid stream, introducing the combined liquid stream to a first transesterification reactor between a liquid glycerol outlet and a liquid alkyl ester outlet, reacting the liquid biomass and the alcohol to form liquid glycerol and liquid alkyl ester, and removing a liquid alkyl ester stream from an upper portion of the first transesterification reactor. The combined liquid stream flows upward through the reactor at a rate that is less than a settling velocity of the liquid glycerol.Type: GrantFiled: September 19, 2007Date of Patent: June 9, 2009Assignee: The University of ConnecticutInventors: Richard Parnas, Clifford Weed, Nicholas Leadbeater, Matthew Boucher
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Patent number: 7528278Abstract: This invention utilizes a mixed salt transesterification catalyst in a transesterification process for the production of esters of alkyl(meth)acrylate monomers.Type: GrantFiled: June 6, 2007Date of Patent: May 5, 2009Assignee: Rohm and Haas CompanyInventors: Abraham Benderly, Michael R. Ryan, Donald R. Weyler
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Patent number: 7521578Abstract: Process for the preparation of acrylic and methacrylic acid esters by transesterification of (meth)acrylic acid esters of the formula I: where R1 is H or CH3 and R2 is an alkyl radical having 1 to 40 carbon atoms, with alkanols which have four or more esterifiable hydroxyl groups, characterized in that 0.01 to 10% by weight, based on the total reaction mixture, of lithium amide catalysts are used as transesterification catalyst.Type: GrantFiled: August 16, 2006Date of Patent: April 21, 2009Assignee: Evonik Roehm GmbHInventors: Bardo Schmitt, Joachim Knebel, Guenther Graeff
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Patent number: 7414147Abstract: The invention relates to a method for producing glycerol carbonate methacrylate in the presence of metal-chelate catalysts of the metal ion-1,3-diketonate type.Type: GrantFiled: August 24, 2004Date of Patent: August 19, 2008Assignee: Roehm GmbH & Co. KGInventors: Bardo Schmitt, Maik Caspari
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Publication number: 20080194862Abstract: The present invention relates to processes for transesterification, comprising the steps of A) mixing an organic acid a) with an ester b) and B) transferring the alcohol radical of the ester b) to the acid a) to obtain the ester of the acid a) and the acid of the ester b), step B) being carried out in a stillType: ApplicationFiled: May 12, 2006Publication date: August 14, 2008Applicant: EVONIK ROEHM GMBHInventors: Jochen Ackermann, Alexander May, Udo Gropp, Hermann Siegert, Bernd Vogel, Soenke Broecker
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Patent number: 7312355Abstract: The invention relates to a method of producing fatty acid monoesters and polyhydroxylic alcohols by means of transesterification between a polyhydroxylic alcohol and a compound that is selected from a fat of animal origin, a fat of vegetable origin, and a fatty acid methyl ester. The invention is characterised in that the transesterification reaction is performed in the presence of basic solid catalysts, said basic solids being oxides that are selected from mixed oxides of one or more monovalent metals and one or more trivalent metals, mixed oxides of one or more divalent metals and one or more trivalent metals, and mixtures of same.Type: GrantFiled: April 12, 2006Date of Patent: December 25, 2007Assignees: Consejo Superior de Investigaciones Cientificas, Universidad Politecnica de Valencia, Universiti MalayaInventors: Avelino Corma Canòs, Sara Iborra Chornet, Alexandra Isabelle Velty, Sharifah Bee Abd Hamid
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Publication number: 20070287841Abstract: This invention utilizes a mixed salt transesterification catalyst in a transesterification process for the production of esters of alkyl(meth)acrylate monomers.Type: ApplicationFiled: June 6, 2007Publication date: December 13, 2007Inventors: Abraham Benderly, Michael R. Ryan, Donald R. Weyler
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Patent number: 7241916Abstract: A method of producing a methacrylic acid ester which comprises carrying out an ester-exchange reaction between methyl methacrylate and an alcohol or a phenol while removing by-product methanol as an azeotropic mixture with methyl methacrylate from the reaction system under reflux conditions, by the use of a reaction apparatus equipped with a distillation column. A methacrylic acid ester is produced with a good productivity by controlling the reflux ratio.Type: GrantFiled: February 3, 2004Date of Patent: July 10, 2007Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Junichi Doi, Yoshihiko Satou, Yoshiyuki Taniguchi, Masanori Tokuda
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Patent number: 7078560Abstract: A process for the preparation of aminoalkyl (meth)acrylates by transesterification from C1–C4-alkyl (meth)acrylates and aminoalcohols is described, in which process the transesterification is carried out in the presence of at least one distannoxane of the general formula (1) wherein R=linear, cyclic or branched alkyl radical having from 1 to 6 carbon atoms, phenyl radical, and the radicals R may be identical or different from one another, Y=halogen, preferably Cl, Br; pseudo-halogen, preferably SCN; OH, OAc or OR, the radicals Y being identical or different from one another, as catalyst, and the use of the aminoalkyl (meth)acrylates prepared according to the process in the preparation of cationic monomers.Type: GrantFiled: November 8, 2004Date of Patent: July 18, 2006Assignee: Stockhausen GmbH & Co. KGInventors: Jochen Houben, Ralph Eickwinkel, Oliver Hoppe, Bernd Kubiak, Erich Kuester
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Patent number: 7071351Abstract: The invention relates to a method for transesterifying methyl methacrylate involving catalysis, particularly zirconium acetylacetonate catalysis. The obtained esters of formula (I) are characterized by having an extremely low content of cross-linking agents.Type: GrantFiled: August 16, 2002Date of Patent: July 4, 2006Assignee: Roehm GmbH & Co. KGInventors: Bardo Schmitt, Joachim Knebel, Maik Caspari
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Patent number: 7026503Abstract: Higher (meth)acrylates IV are prepared by transesterification of a lower (meth)acrylate I with a higher alcohol R2OH in the presence of a stabilizer or stabilizer mixture and of a catalyst or catalyst mixture, by a process in which the liberated lower alkanol R1OH is separated off and is fed at least partly to the preparation of the lower (meth)acrylate I.Type: GrantFiled: May 28, 2002Date of Patent: April 11, 2006Assignee: BASF AktiengesellschaftInventors: Gerhard Nestler, Ulrich Rauh, Jürgen Schröder
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Patent number: 6979748Abstract: A process for the preparation of aminoalkyl (meth)acrylates by transesterification from C1-C4-alkyl (meth)acrylates and aminoalcohols is described, in which process the transesterification is carried out in the presence of at least one distannoxane of the general formula (1) wherein R=linear, cyclic or branched alkyl radical having from 1 to 6 carbon atoms, phenyl radical, and the radicals R may be identical or different from one another, Y=halogen, preferably Cl, Br; pseudo-halogen, preferably SCN; OH, OAc or OR, the radicals Y being identical or different from one another, as catalyst, and the use of the aminoalkyl(meth)acrylates prepared according to the process in the preparation of cationic monomers.Type: GrantFiled: June 1, 2001Date of Patent: December 27, 2005Assignee: Stockhausen GmbH & Co. KGInventors: Jochen Houben, Ralph Eickwinkel, Oliver Hoppe, Bernd Kubiak, Erich Kuester
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Patent number: 6977310Abstract: The invention relates to a process for continuous preparation of alkyl (meth)acrylates by transesterification of methyl (meth)acrylate using alcohols which are high-boiling relative to methanol. A particular workup technique achieves product qualities which have hitherto not been attained. Very high space-time and overall yields can also be achieved.Type: GrantFiled: December 6, 2002Date of Patent: December 20, 2005Assignee: Roehm GmbH & Co. KGInventors: Jochen Ackermann, Udo Gropp, Horst Hiltner, Hans-Rolf Rausch, Ingrid Lunt-Rieg, Hermann Siegert, Ruediger Carloff
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Patent number: 6881858Abstract: Asymmetric (meth)acrylate crosslinking agents may be prepared by reacting a hydroxyacrylate with methacrylic anhydride to give a crosslinking agent with acrylic and methacrylic groups. Asymmetric (meth)acrylate crosslinking agents can be employed in the production of superabsorbers and thickening agents.Type: GrantFiled: January 11, 2002Date of Patent: April 19, 2005Assignee: ROEHM GmbH & Co. KGInventor: Werner Siol
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Patent number: 6875888Abstract: In a process for preparing an ester of an unsaturated carboxylic acid by reacting an ester of the unsaturated carboxylic acid and a C1-C4-alkanol with an alcohol R3OH, where R3 is a C4-C20-alkyl radical, a C5-C7-cycloalkyl radical, a phenyl-C1-C4-alkyl radical or a C2-C12-alkyl radical substituted by at least one NR5R5 group or by from 1 to 3 hydroxyl groups or C1-C4-alkoxyl groups or interrupted by one or more oxygen atoms, where the radicals R5 are, independently of one another, C1-C6-alkyl or together with the nitrogen atom form a 5- to 7-membered heterocyclic ring which may contain a further nitrogen or oxygen atom, in the presence of a transesterification catalyst, the transesterification catalyst used is at least one metal alkanolate containing at least one OR1 group, where R1 is a 2,2,6,6-tetraalkyl-1-oxylpiperidin-4-yl radical.Type: GrantFiled: May 28, 2001Date of Patent: April 5, 2005Assignee: BASF AktiengesellschaftInventors: Gerhard Nestler, Jürgen Schröder
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Patent number: 6872848Abstract: Alkylpolyalkylene glycol esters of monoethylenically unsaturated carboxylic acids are prepared by esterifying (a) monoethylenically unsaturated carboxylic acids with (b) polyalkylene glycols which are endcapped at one end, in the absence of a solvent and in the presence of polymerization inhibitors and esterification catalysts at not more than 160° C. by a process in which the esterification is first carried out under atmospheric pressure or at up to 50 bar, the water formed in the esterification is then distilled from the reaction mixture at from 10 to 500 mbar and the esterification is then continued under atmospheric pressure or at up to 50 bar.Type: GrantFiled: December 14, 2001Date of Patent: March 29, 2005Assignee: BASF AktiengesellschaftInventors: Matthias Kroner, Jürgen Pfister, Dieter Faul, Hans-Jürgen Raubenheimer, Karl-Heinz Büchner
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Patent number: 6841697Abstract: Process for preparing a compound (I) by reacting a compound of formula (II) with the alcohol (III). The reaction is carried out using dibutyltin oxide as transesterification catalyst. R1=H or CH3 R2=linear C1-C4 alkyl radical.Type: GrantFiled: April 26, 2002Date of Patent: January 11, 2005Assignee: AtofinaInventors: Alain Riondel, Fabrice Castellani
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Patent number: 6838576Abstract: A process for preparing functional group-containing olefinic compounds comprises the steps of (a) reacting at least one alkylidene phosphorane with at least one carbonyl-containing compound that comprises at least one group that is a leaving group, or that is capable of subsequent conversion to a leaving group, to form an olefinic compound that comprises at least one leaving group, the carbonyl-containing compound being selected from the group consisting of ketones and aldehydes; and (b) reacting the olefinic compound with at least one functional group-containing nucleophile to form a functional group-containing olefinic compound.Type: GrantFiled: October 23, 2003Date of Patent: January 4, 2005Assignee: 3M Innovative Properties CompanyInventors: Markus A. Wicki, Kent E. Nielsen
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Patent number: 6835849Abstract: The invention relates to the synthesis of alkenoate esters from a corresponding lactone and an alcohol in the presence of a basic catalyst. More specifically, this invention relates to the synthesis of methyl-4-pentenoate ester from 5-methyl butyrolactone and methanol.Type: GrantFiled: July 11, 2003Date of Patent: December 28, 2004Assignee: E. I. du Pont de Nemours and CompanyInventor: Leo Ernest Manzer
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Publication number: 20040171868Abstract: The invention relates to a method for producing (meth)acrylic acid esters IV by means of transesterification of a (meth)acrylic acid ester I with an alcohol R2OH comprising at least one more carbon atom than the alcohol constituents (R1O—) in the (meth)acrylic acid ester I to be subjected to transesterification, in the presence of a catalyst or a catalyst mixture. Either essentially the (meth)acrylic acid ester I is separated and then the catalyst used is separated by distillation (catalyst separation), or the catalyst used is separated by distillation first (catalyst separation), and then essentially the (meth)acrylic acid ester I is separated, from the reaction product of the transesterification. Constituents from the mixture obtained, which have a lower boiling point than the (meth)acrylic acid ester IV, are essentially separated by distillation (separation of constituents at low boiling point), and the (meth)acrylic acid ester IV is then purified by distillation (purification by distillation).Type: ApplicationFiled: December 4, 2003Publication date: September 2, 2004Inventors: Matthias Geisendoerfer, Albrecht Dams, Gerhard Nestler
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Publication number: 20040158096Abstract: Higher (meth)acrylates IV are prepared by transesterification of a lower (meth)acrylate I with a higher alcohol R2OH in the presence of a stabilizer or stabilizer mixture and of a catalyst or catalyst mixture, by a process in which the liberated lower alkanol R1OH is separated off and is fed at least partly to the preparation of the lower (meth)acrylate I.Type: ApplicationFiled: December 8, 2003Publication date: August 12, 2004Inventors: Gerhard Nestler, Ulrich Rauh, Jurgen Schroder
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Publication number: 20040092764Abstract: A process for the preparation of aminoalkyl (meth)acrylates by transesterification from C1-C4-alkyl (meth)acrylates and aminoalcohols is described, in which process the transesterification is carried out in the presence of at least one distannoxane of the general formula (1) 1Type: ApplicationFiled: December 18, 2002Publication date: May 13, 2004Inventors: Jochen Houben, Ralph Eickwinkel, Oliver Hoppe, Bernd Kubiak, Erich Kuester
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Patent number: 6646155Abstract: An ester of an &agr;,&bgr;-unsaturated carboxylic acid is prepared by reacting the carboxylic acid with a C6-C12-alkanol, cyclopentanol or cyclohexanol in the presence of an acidic esterification catalyst and of an entraining agent for removing the water of reaction formed in the esterification, by a process in which the entraining agent used is the olefin on which the alkanol is based.Type: GrantFiled: August 5, 2002Date of Patent: November 11, 2003Assignee: BASF AktiengesellschaftInventors: Reinhard Herzog, Gerhard Nestler, Jürgen Schröder
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Patent number: 6639099Abstract: A process for the synthesis and recovery of di(meth)acrylic acid esters at a high degree of purity. Di(meth)acrylic acid esters are produced by transesterfication of (meth)acrylic acid esters of C1 to C4 alcohols with 1,n-diols (where n≧3) in the presence of a zirconium catalyst that comprises a chelate of zirconium with a 1,3-dicarbonyl compound. These catalysts can be readily separated or removed from the reaction mixture by precipitation with phosphoric acid, thus providing a convenient and inexpensive method of producing a di(meth)acrylic acid ester with a reduced level of zirconium.Type: GrantFiled: August 24, 2000Date of Patent: October 28, 2003Assignee: Roehm GmbH & Co. KGInventors: Joachim Knebel, Joachim Carl, Guenter Graeff, Andrea Wittkowski
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Patent number: 6541658Abstract: Acrylic or methacrylic acid esters may be efficiently prepared by the transesterification of a C1 to C4 alcohol ester of acrylic or methacrylic acid and a different alcohol in the presence of a mixture of a) an alkali metal cyanate or alkali metal thiocyanate, and b) an alkaline earth metal oxide, an alkaline earth metal hydroxide or an alkali metal halide.Type: GrantFiled: January 11, 2002Date of Patent: April 1, 2003Assignee: Roehm GmbH & Co., KGInventors: Joachim Knebel, Ralf Merbach, Santa Maria Nuccio
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Publication number: 20020183543Abstract: Process for preparing a compound (I) by reacting a compound of formula (II) with the alcohol (III).Type: ApplicationFiled: April 26, 2002Publication date: December 5, 2002Applicant: ATOFINAInventors: Alain Riondel, Fabrice Castellani
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Patent number: 6489258Abstract: This invention provides an article, compositions, methods of making and uses of vapor-deposited metal compounds immobilized on porous substrates. The substrate is a porous substrate having an average pore size of at least about 8 Å and a surface area of at least about 10 m2/g. The methods describe the vapor-deposition of an inorganic compound onto the substrate where the deposition is accomplished with a relatively small amount of ligand loss. The substrate can be pre-treated to achieve a uniformly dispersed metal compound deposited on the substrate. The inorganic compound can decompose into a metal compound. The article can also function as a catalyst for carbon-heteroatom coupling reactions such as carbon-carbon coupling reactions, most notably, the Heck reaction.Type: GrantFiled: October 15, 1999Date of Patent: December 3, 2002Assignee: Massachusetts Institute of TechnologyInventors: Jackie Y. Ying, Christian P. Mehnert
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Patent number: 6479696Abstract: Isobornyl (meth)acrylate is synthesized by a two-stage one-pot process, wherein isobornyl acetate is converted to isoborneol followed by transesterification with (meth)acrylic acid methyl ester, without isolation of the intermediates or purification of the product.Type: GrantFiled: July 5, 2000Date of Patent: November 12, 2002Assignee: Roehm GmbH & Co KGInventors: Joachim Knebel, Doris Saal
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Publication number: 20020123643Abstract: A methylcyclohexyl (meth)acrylate with formula (I) is prepared by reacting a lower (meth)acrylate (II) with an alcohol (III) in the presence of a transesterification catalyst selected from titanium, tin, zirconium, magnesium, calcium, lithium, potassium or sodium alcoholates; chelates of zirconium, calcium, magnesium or lithium with 1,3-dicarbonyl compounds; dialkyltin oxides, dialkyltin dialkoxides, dialkyltin diesters and distannoxanes and magnesium, calcium or lithium hydroxides.Type: ApplicationFiled: October 25, 2001Publication date: September 5, 2002Applicant: ATOFINAInventor: Jean-Micheal Paul
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Patent number: 6437173Abstract: The present invention relates to the manufacture of a dialkylaminoalkyl (meth)acrylate by transesterification of methyl or ethyl (meth)acrylate with an amino alcohol. The transesterification catalyst is chosen from tetrabutyl, tetraethyl and tetra(2-ethylhexyl) titanates. The reaction is carried out in a stirred reactor at 90-120° C., after which the crude reaction mixture is sent to a tailing column (C1), the flow from the top of this column is sent to a topping column (C2) and the flow from the bottom of this column si then sent to a final rectification column (C3). A dialkylaminoalkyl (meth)acrylate of high purity is obtained in this way.Type: GrantFiled: April 21, 1999Date of Patent: August 20, 2002Assignee: Elf Atochem S.A.Inventors: Patrice Hurtel, Charles Hazan, Norbert Richard
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Publication number: 20020111511Abstract: Acrylic or methacrylic acid esters may be efficiently prepared by the transesterification of a C1 to C4 alcohol ester of acrylic or methacrylic acid and a different alcohol in the presence of a mixture of a) an alkali metal cyanate or alkali metal thiocyanate, and b) an alkaline earth metal oxide, an alkaline earth metal hydroxide or an alkali metal halide.Type: ApplicationFiled: January 11, 2002Publication date: August 15, 2002Applicant: ROEHM GMBH & CO. KGInventors: Joachim Knebel, Ralf Merbach, Santa Maria Nuccio
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Patent number: 6417392Abstract: In the operation of producing an alkylamino(meth)acrylate by the reaction of transesterification of an alkyl(meth)acrylate with an alkylamino alcohol, the alkyl alcohol by-produced during the transesterification is distilled in the form of an azeotropic mixture with the alkyl(meth)acrylate, the resultant distillate is purified with an ion-exchange resin and handled, on the other hand, the reaction solution is distilled to allow separation of the catalyst wherein is provided a method and apparatus for effecting, in the production of the alkylamino(meth)acrylate, the distillation under such a condition as represses the amount of in crease of the Michael adduct below 2%.Type: GrantFiled: October 1, 1998Date of Patent: July 9, 2002Assignee: Nippon Shokubai Co., Ltd.Inventors: Hideaki Nagano, Tadayoshi Kawashima, Tetsuya Kajihara, Kaoru Iwasaki, Sumio Nakashima
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Patent number: 6355830Abstract: A process for producing a dicarboxylic acid monoester which comprises subjecting a dicarboxylic acid monoester or an alkali metal salt of a dicarboxylic acid monoester and a metal alkoxide to transesterification in the presence of an organic solvent, or a process for producing a dicarboxylic acid monoester which comprises subjecting a dicarboxylic acid monoester or an alkali metal salt of a dicarboxylic acid monoester and an alcohol to transesterification in the presence of a metal alkoxide.Type: GrantFiled: April 9, 1999Date of Patent: March 12, 2002Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Kunihiko Sakano, Junji Fujii, Tetsuya Ikemoto
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Patent number: 6342627Abstract: There is disclosed a process for producing an unsaturated ester of the formula (3): wherein R1, R2 and R3 independently represent hydrogen, halogen, alkyl, alkenyl and the like and R5 represents alkyl which may be substituted and the like, which process is characterized by subjecting an unsaturated ester of the formula (1): wherein R1, R2 and R3 have the same meaning as previously defined and R4 represents alkyl or phenyl and the like, to a transesterification reaction with a hydroxy compound of the formula (2): R5OH (2) wherein R5 has the same meaning as previously defined, in the presence of a lanthanoide metal alkoxide.Type: GrantFiled: December 14, 1999Date of Patent: January 29, 2002Assignee: Sumitomo Chemical Company, LimitedInventors: Yoshiaki Oda, Makoto Yako, Kazunori Iwakura
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Patent number: 6329543Abstract: The present invention relates to processes for synthesis of isobornyl (meth)acrylate by reacting camphene with (meth)acrylic acid in the presence of sulfuric acid and at least one compound having inhibiting action. Aqueous sulfuric acid with an acid concentration in the range of 65 to 85 wt % is used. Isobornyl (meth)acrylate can advantageously be distilled from a mixture containing sulfuric acid in the presence of 2,6-di-tert-butyl-&agr;-(dialkylamino)-p-cresol.Type: GrantFiled: May 3, 2000Date of Patent: December 11, 2001Assignee: Roehm GmbH & Co KGInventors: Joachim Knebel, Doris Saal
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Patent number: 6316664Abstract: Formic ester is transesterified with a hydroxyl-containing compound in the presence of a tertiary amine as transesterification catalyst to form a formic ester which differs from the formic ester used as reactant, and of a hydroxyl-containing compound which is different from the hydroxyl-containing compound used as reactant.Type: GrantFiled: May 8, 1998Date of Patent: November 13, 2001Assignee: BASF AktiengesellschaftInventors: Detlef Kratz, Christoph Sigwart
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Patent number: 6268521Abstract: The present invention provides a process for enzymatic preparation of acrylic esters and/or methacrylic esters of polyoxyalkylenes, and to the use thereof. The acryloyl and/or methacryloyl compounds of polyoxyalkylenes are obtainable by a process for esterifying or transesterifying acrylic and/or methacrylic acid or acrylic and/or methacrylic esters with a polyoxyalkylene of the general formula (I) wherein R1, R2, R3 and a-e are as defined in claim 1 and wherein at least one OH group is present per molecule and the sequence of the polyoxyalkylene segments (C2H4-aR2aO)b and (CcH2cO)d is arbitrary, in the presence of an enzyme which catalyzes the esterification or transesterification.Type: GrantFiled: November 1, 1999Date of Patent: July 31, 2001Assignee: Goldschmidt AGInventors: Burghard Gruning, Geoffrey Hills, Wolfgang Josten, Dietmar Schaefer, Stefan Silber, Christian Weitemeyer
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Patent number: 6215018Abstract: 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 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.Type: GrantFiled: October 12, 1999Date of Patent: April 10, 2001Assignee: Ciba Specialty Chemicals CorporationInventors: Timothy M. Miller, Narayanan Pondicherry, Louis E. Trapasso, Aaron van de Sande
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Patent number: 6211422Abstract: A method for the enzymatic production of a desired product in a liquid or supercritical carbon dioxide fluid. The method comprises: (a) providing a reaction mixture comprising at least one reaction substrate and a crosslinked enzyme crystal catalyst in a liquid or supercritical carbon dioxide fluid; and (b) reacting said substrate with said crosslinked enzyme crystal catalyst in said carbon dioxide fluid to produce said product. The reacting step is typically followed by the step of (c) separating the product from said reaction mixture.Type: GrantFiled: July 13, 1999Date of Patent: April 3, 2001Assignees: North Carolina State University, The University of North Carolina at Chapel HillInventors: Joseph M. DeSimone, Ruben G. Carbonell, Stephanie A. Crette, Jonathan L. Kendall
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Patent number: 6147252Abstract: A process for continuously producing an alkyl ester of acrylic or methacrylic acid by ester interchange reaction represented by the following reaction scheme: ##STR1## wherein R.sup.1 is hydrogen or methyl, R.sup.2 is an alkyl having 1 to 6 carbon atoms, R.sup.3 is an alkyl having 2 to 20 carbon atoms or a mono- or polyhydroxyalkyl having 2 to 20 carbon atoms such that R.sup.2 OH has a boiling point lower than that of R.sup.3 OH. The reaction is continuously carried out in a continuous multi-stage distillation column while simultaneously removing the low-boiling R.sup.2 OH from the reaction zone by distillation, thereby shifting the equilibrium toward the product side to enhance the production of the target alkyl ester.Type: GrantFiled: June 30, 1999Date of Patent: November 14, 2000Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Kenichi Nakamura, Futoshi Kawataka
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Patent number: 6130275Abstract: This invention relates to a composition comprising a mixture of a fumarate, maleate and 2-allyloxy-succinate esters falling within the area defined by points A, B, C, and D of a triangular chemical composition diagram (hereafter "TCCD") said points representing respectively the ranges of concentration of said maleate, fumarate and succinate in said composition, a process for preparing the same and the use thereof as a reactive diluent in a paint or coating formulation.Type: GrantFiled: August 12, 1998Date of Patent: October 10, 2000Assignee: BP Chemicals LimitedInventors: Benjamin Patrick Gracey, Christopher Hallett, Robert Paul Klaasen
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Patent number: 6090974Abstract: This invention includes an alkyl 3-oxoalkanoate, and processes for its preparation and use for the synthesis of fatty hydroxylated amino acids, fatty amino alcohols and ceramides.Type: GrantFiled: October 15, 1996Date of Patent: July 18, 2000Assignee: L'Oreal SAInventors: Michel Philippe, Bernadette Luppi, Didier Semeria, Claude Mahieu
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Patent number: 6087528Abstract: A process for producing hydroxyalkyl monoacrylate of the present invention, comprises the steps of: reacting acrylic acid or an acrylic acid derivative with alkane diol for esterification and/or transesterification therebetween in the presence of a reaction catalyst comprising a stannoxane compound; recovering said reaction catalyst from a liquid reaction product by extraction; and recycling the recovered reaction catalyst to a reaction system for said esterification and/or transesterification. The process of the present invention is an industrially useful process for producing hydroxyalkyl monoacrylate, which is excellent in reactivity, selectivity for an aimed product, stability of a reaction catalyst used and stability of a reaction substrate and product, and is improved so as to effectively recover and reuse the reaction catalyst.Type: GrantFiled: May 26, 1998Date of Patent: July 11, 2000Assignee: Mitsubishi Chemical CorporationInventors: Toshiharu Yokoyama, Yuuji Kawaragi, Kouya Murai
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Patent number: 6040473Abstract: A transesterification process for the preparation of (meth)acrylates wherein a (meth)acrylic acid ester is re-esterified in the presence of a re-esterification catalyst comprised of calcium hydroxide or calcium hydroxide in combination with lithium chloride.Type: GrantFiled: July 20, 1998Date of Patent: March 21, 2000Assignee: Roehm GmbHInventors: Joachim Knebel, Werner Spalt