Preparing Esters By Ester Interchange Patents (Class 560/217)
  • Publication number: 20110046399
    Abstract: 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: Application
    Filed: August 5, 2010
    Publication date: February 24, 2011
    Inventors: Rene Johan Haan, Jean-Paul Lange
  • Publication number: 20100298594
    Abstract: 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: Application
    Filed: May 19, 2009
    Publication date: November 25, 2010
    Inventors: Larry E. Brammer, JR., Barbara E. Fair, Cheng-Sung Huang, Linh Quach, Peter E. Reed, Leonard M. Ver Vers
  • Patent number: 7781610
    Abstract: 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: Grant
    Filed: February 19, 2010
    Date of Patent: August 24, 2010
    Assignee: Chemtura Corporation
    Inventors: Uwe Schneider, Bernard Jousseaume, Karine Darriet, Thierry Toupance
  • Publication number: 20100204509
    Abstract: 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: Application
    Filed: May 8, 2008
    Publication date: August 12, 2010
    Applicant: EVONIK ROEHM GMBH
    Inventors: Guido Protzmann, Harald Trauthwein, Joachim Knebel, Thorben Schuetz, Gerhard Koelbl, Thomas Kehr, Guenther Lauster
  • Publication number: 20100145092
    Abstract: 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: Application
    Filed: November 30, 2007
    Publication date: June 10, 2010
    Applicant: Arkema France
    Inventor: Jean-Michel Paul
  • Patent number: 7696376
    Abstract: 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: Grant
    Filed: June 23, 2004
    Date of Patent: April 13, 2010
    Assignee: Japan Energy Corporation
    Inventor: Satoshi Furuta
  • Patent number: 7544830
    Abstract: 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: Grant
    Filed: September 19, 2007
    Date of Patent: June 9, 2009
    Assignee: The University of Connecticut
    Inventors: Richard Parnas, Clifford Weed, Nicholas Leadbeater, Matthew Boucher
  • Patent number: 7528278
    Abstract: This invention utilizes a mixed salt transesterification catalyst in a transesterification process for the production of esters of alkyl(meth)acrylate monomers.
    Type: Grant
    Filed: June 6, 2007
    Date of Patent: May 5, 2009
    Assignee: Rohm and Haas Company
    Inventors: Abraham Benderly, Michael R. Ryan, Donald R. Weyler
  • Patent number: 7521578
    Abstract: 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: Grant
    Filed: August 16, 2006
    Date of Patent: April 21, 2009
    Assignee: Evonik Roehm GmbH
    Inventors: Bardo Schmitt, Joachim Knebel, Guenther Graeff
  • Patent number: 7414147
    Abstract: 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: Grant
    Filed: August 24, 2004
    Date of Patent: August 19, 2008
    Assignee: Roehm GmbH & Co. KG
    Inventors: Bardo Schmitt, Maik Caspari
  • Publication number: 20080194862
    Abstract: 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 still
    Type: Application
    Filed: May 12, 2006
    Publication date: August 14, 2008
    Applicant: EVONIK ROEHM GMBH
    Inventors: Jochen Ackermann, Alexander May, Udo Gropp, Hermann Siegert, Bernd Vogel, Soenke Broecker
  • Patent number: 7312355
    Abstract: 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: Grant
    Filed: April 12, 2006
    Date of Patent: December 25, 2007
    Assignees: Consejo Superior de Investigaciones Cientificas, Universidad Politecnica de Valencia, Universiti Malaya
    Inventors: Avelino Corma Canòs, Sara Iborra Chornet, Alexandra Isabelle Velty, Sharifah Bee Abd Hamid
  • Publication number: 20070287841
    Abstract: This invention utilizes a mixed salt transesterification catalyst in a transesterification process for the production of esters of alkyl(meth)acrylate monomers.
    Type: Application
    Filed: June 6, 2007
    Publication date: December 13, 2007
    Inventors: Abraham Benderly, Michael R. Ryan, Donald R. Weyler
  • Patent number: 7241916
    Abstract: 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: Grant
    Filed: February 3, 2004
    Date of Patent: July 10, 2007
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Junichi Doi, Yoshihiko Satou, Yoshiyuki Taniguchi, Masanori Tokuda
  • Patent number: 7078560
    Abstract: 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: Grant
    Filed: November 8, 2004
    Date of Patent: July 18, 2006
    Assignee: Stockhausen GmbH & Co. KG
    Inventors: Jochen Houben, Ralph Eickwinkel, Oliver Hoppe, Bernd Kubiak, Erich Kuester
  • Patent number: 7071351
    Abstract: 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: Grant
    Filed: August 16, 2002
    Date of Patent: July 4, 2006
    Assignee: Roehm GmbH & Co. KG
    Inventors: Bardo Schmitt, Joachim Knebel, Maik Caspari
  • Patent number: 7026503
    Abstract: 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: Grant
    Filed: May 28, 2002
    Date of Patent: April 11, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Nestler, Ulrich Rauh, Jürgen Schröder
  • Patent number: 6979748
    Abstract: 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: Grant
    Filed: June 1, 2001
    Date of Patent: December 27, 2005
    Assignee: Stockhausen GmbH & Co. KG
    Inventors: Jochen Houben, Ralph Eickwinkel, Oliver Hoppe, Bernd Kubiak, Erich Kuester
  • Patent number: 6977310
    Abstract: 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: Grant
    Filed: December 6, 2002
    Date of Patent: December 20, 2005
    Assignee: Roehm GmbH & Co. KG
    Inventors: Jochen Ackermann, Udo Gropp, Horst Hiltner, Hans-Rolf Rausch, Ingrid Lunt-Rieg, Hermann Siegert, Ruediger Carloff
  • Patent number: 6881858
    Abstract: 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: Grant
    Filed: January 11, 2002
    Date of Patent: April 19, 2005
    Assignee: ROEHM GmbH & Co. KG
    Inventor: Werner Siol
  • Patent number: 6875888
    Abstract: 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: Grant
    Filed: May 28, 2001
    Date of Patent: April 5, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Nestler, Jürgen Schröder
  • Patent number: 6872848
    Abstract: 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: Grant
    Filed: December 14, 2001
    Date of Patent: March 29, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Kroner, Jürgen Pfister, Dieter Faul, Hans-Jürgen Raubenheimer, Karl-Heinz Büchner
  • Patent number: 6841697
    Abstract: 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: Grant
    Filed: April 26, 2002
    Date of Patent: January 11, 2005
    Assignee: Atofina
    Inventors: Alain Riondel, Fabrice Castellani
  • Patent number: 6838576
    Abstract: 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: Grant
    Filed: October 23, 2003
    Date of Patent: January 4, 2005
    Assignee: 3M Innovative Properties Company
    Inventors: Markus A. Wicki, Kent E. Nielsen
  • Patent number: 6835849
    Abstract: 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: Grant
    Filed: July 11, 2003
    Date of Patent: December 28, 2004
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Leo Ernest Manzer
  • Publication number: 20040171868
    Abstract: 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: Application
    Filed: December 4, 2003
    Publication date: September 2, 2004
    Inventors: Matthias Geisendoerfer, Albrecht Dams, Gerhard Nestler
  • Publication number: 20040158096
    Abstract: 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: Application
    Filed: December 8, 2003
    Publication date: August 12, 2004
    Inventors: Gerhard Nestler, Ulrich Rauh, Jurgen Schroder
  • Publication number: 20040092764
    Abstract: 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) 1
    Type: Application
    Filed: December 18, 2002
    Publication date: May 13, 2004
    Inventors: Jochen Houben, Ralph Eickwinkel, Oliver Hoppe, Bernd Kubiak, Erich Kuester
  • Patent number: 6646155
    Abstract: 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: Grant
    Filed: August 5, 2002
    Date of Patent: November 11, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Reinhard Herzog, Gerhard Nestler, Jürgen Schröder
  • Patent number: 6639099
    Abstract: 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: Grant
    Filed: August 24, 2000
    Date of Patent: October 28, 2003
    Assignee: Roehm GmbH & Co. KG
    Inventors: Joachim Knebel, Joachim Carl, Guenter Graeff, Andrea Wittkowski
  • Patent number: 6541658
    Abstract: 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: Grant
    Filed: January 11, 2002
    Date of Patent: April 1, 2003
    Assignee: Roehm GmbH & Co., KG
    Inventors: Joachim Knebel, Ralf Merbach, Santa Maria Nuccio
  • Publication number: 20020183543
    Abstract: Process for preparing a compound (I) by reacting a compound of formula (II) with the alcohol (III).
    Type: Application
    Filed: April 26, 2002
    Publication date: December 5, 2002
    Applicant: ATOFINA
    Inventors: Alain Riondel, Fabrice Castellani
  • Patent number: 6489258
    Abstract: 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: Grant
    Filed: October 15, 1999
    Date of Patent: December 3, 2002
    Assignee: Massachusetts Institute of Technology
    Inventors: Jackie Y. Ying, Christian P. Mehnert
  • Patent number: 6479696
    Abstract: 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: Grant
    Filed: July 5, 2000
    Date of Patent: November 12, 2002
    Assignee: Roehm GmbH & Co KG
    Inventors: Joachim Knebel, Doris Saal
  • Publication number: 20020123643
    Abstract: 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: Application
    Filed: October 25, 2001
    Publication date: September 5, 2002
    Applicant: ATOFINA
    Inventor: Jean-Micheal Paul
  • Patent number: 6437173
    Abstract: 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: Grant
    Filed: April 21, 1999
    Date of Patent: August 20, 2002
    Assignee: Elf Atochem S.A.
    Inventors: Patrice Hurtel, Charles Hazan, Norbert Richard
  • Publication number: 20020111511
    Abstract: 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: Application
    Filed: January 11, 2002
    Publication date: August 15, 2002
    Applicant: ROEHM GMBH & CO. KG
    Inventors: Joachim Knebel, Ralf Merbach, Santa Maria Nuccio
  • Patent number: 6417392
    Abstract: 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: Grant
    Filed: October 1, 1998
    Date of Patent: July 9, 2002
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Hideaki Nagano, Tadayoshi Kawashima, Tetsuya Kajihara, Kaoru Iwasaki, Sumio Nakashima
  • Patent number: 6355830
    Abstract: 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: Grant
    Filed: April 9, 1999
    Date of Patent: March 12, 2002
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Kunihiko Sakano, Junji Fujii, Tetsuya Ikemoto
  • Patent number: 6342627
    Abstract: 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: Grant
    Filed: December 14, 1999
    Date of Patent: January 29, 2002
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoshiaki Oda, Makoto Yako, Kazunori Iwakura
  • Patent number: 6329543
    Abstract: 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: Grant
    Filed: May 3, 2000
    Date of Patent: December 11, 2001
    Assignee: Roehm GmbH & Co KG
    Inventors: Joachim Knebel, Doris Saal
  • Patent number: 6316664
    Abstract: 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: Grant
    Filed: May 8, 1998
    Date of Patent: November 13, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Detlef Kratz, Christoph Sigwart
  • Patent number: 6268521
    Abstract: 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: Grant
    Filed: November 1, 1999
    Date of Patent: July 31, 2001
    Assignee: Goldschmidt AG
    Inventors: Burghard Gruning, Geoffrey Hills, Wolfgang Josten, Dietmar Schaefer, Stefan Silber, Christian Weitemeyer
  • Patent number: 6215018
    Abstract: 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: Grant
    Filed: October 12, 1999
    Date of Patent: April 10, 2001
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Timothy M. Miller, Narayanan Pondicherry, Louis E. Trapasso, Aaron van de Sande
  • Patent number: 6211422
    Abstract: 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: Grant
    Filed: July 13, 1999
    Date of Patent: April 3, 2001
    Assignees: North Carolina State University, The University of North Carolina at Chapel Hill
    Inventors: Joseph M. DeSimone, Ruben G. Carbonell, Stephanie A. Crette, Jonathan L. Kendall
  • Patent number: 6147252
    Abstract: 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: Grant
    Filed: June 30, 1999
    Date of Patent: November 14, 2000
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Kenichi Nakamura, Futoshi Kawataka
  • Patent number: 6130275
    Abstract: 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: Grant
    Filed: August 12, 1998
    Date of Patent: October 10, 2000
    Assignee: BP Chemicals Limited
    Inventors: Benjamin Patrick Gracey, Christopher Hallett, Robert Paul Klaasen
  • Patent number: 6090974
    Abstract: 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: Grant
    Filed: October 15, 1996
    Date of Patent: July 18, 2000
    Assignee: L'Oreal SA
    Inventors: Michel Philippe, Bernadette Luppi, Didier Semeria, Claude Mahieu
  • Patent number: 6087528
    Abstract: 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: Grant
    Filed: May 26, 1998
    Date of Patent: July 11, 2000
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Toshiharu Yokoyama, Yuuji Kawaragi, Kouya Murai
  • Patent number: 6040473
    Abstract: 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: Grant
    Filed: July 20, 1998
    Date of Patent: March 21, 2000
    Assignee: Roehm GmbH
    Inventors: Joachim Knebel, Werner Spalt