Preparing Esters By Ester Interchange Patents (Class 560/217)
  • Patent number: 10774025
    Abstract: The present invention provides a production method of a multifunctional acrylate with a reduced tin content which includes adding an acid to a mixture containing an organotin compound and a multifunctional acrylate and distilling the mixture containing the acid.
    Type: Grant
    Filed: April 26, 2018
    Date of Patent: September 15, 2020
    Assignee: OSAKA ORGANIC CHEMICAL INDUSTRY LTD.
    Inventors: Keisuke Ito, Shigeaki Matsumoto, Keita Shigematsu
  • Patent number: 10647784
    Abstract: Provided is a resin including both a structural unit derived from a monomer having a carbon-carbon double bond at a terminal thereof and a structural unit derived from a polyrotaxane compound, wherein the polyrotaxane compound is a compound substituted with a (meth)acryloyl group or a group containing a (meth)acryloyl group, the polyrotaxane includes optionally substituted cyclodextrin, a linear molecule clathrated in the optionally substituted cyclodextrin in a skewer shape, and a capping group for preventing the optionally substituted cyclodextrin from leaving, the capping group being located at a terminal of the linear molecule clathrated in the optionally substituted cyclodextrin in a skewer shape, and the weight average molecular weight of the linear molecule clathrated in the optionally substituted cyclodextrin in a skewer shape is greater than or equal to 21000 and less than or equal to 500000.
    Type: Grant
    Filed: July 20, 2016
    Date of Patent: May 12, 2020
    Assignee: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Yoshinori Sato, Kenta Ishizuka
  • Patent number: 10479757
    Abstract: The invention relates to the use of 2,6,-di-tert-butyl-4-methylphenol at a moiety of 25 to 200 ppm for stabilizing N,N-dimethylaminoethyl acrylate in respect of discoloring effects. The invention also relates to an N,N-dimethylaminoethyl acrylate stabilized in said manner and to a method for producing the same.
    Type: Grant
    Filed: April 24, 2017
    Date of Patent: November 19, 2019
    Assignee: Arkema France
    Inventors: Fanny Dubut, Benoit Riflade, Sandra Maget
  • Patent number: 10343980
    Abstract: N,N-(di)alkylaminoalkyl(meth)acrylamide or N,N-(di)alkylaminoalkyl (meth)acrylate and/or a quaternary ammonium salt thereof are prepared with a low content of a compound of formula (IV) wherein R5 in each case is a linear, branched or cyclic alkyl radical, an aryl radical which may also be substituted by one or more alkyl groups, the linear, cyclic or branched alkyl radical may have a length of 1-12 carbon atoms and is, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, isooctyl, nonyl, decyl, undecyl, dodecyl.
    Type: Grant
    Filed: June 16, 2017
    Date of Patent: July 9, 2019
    Assignee: Evonik Roehm GmbH
    Inventors: Steffen Krill, Patrik Hartmann
  • Patent number: 10144696
    Abstract: A transesterification catalyst that is heterogeneous and a method for preparing said transesterification catalyst are provided. The catalyst can be used in a variety of transesterification reactor configurations including CSTR (continuous stirred tank reactors), ebullated (or ebullating) beds or any other fluidized bed reactors, and PFR (plug flow, fixed bed reactors). The catalyst can be used for manufacturing commercial grade biodiesel, biolubricants and glycerin.
    Type: Grant
    Filed: April 15, 2016
    Date of Patent: December 4, 2018
    Assignee: CRYSTAPHASE PRODUCTS, INC.
    Inventors: Umakant Pravinchandra Joshi, Peter Gregory Ham
  • Patent number: 10065916
    Abstract: A method for producing a (meth)acrylate comprises transesterification reaction of an alcohol and a monofunctional(meth) acrylate with catalysts in combination being cyclic tertiary amines having an azabicyclo structure and compounds containing zinc, separating a solid that contains the catalysts from a reaction product containing a (meth)acrylate, and producing a (meth)acrylate by transesterification reaction of an alcohol and a monofunctional (meth)acrylate, while using the recovered solid catalyst.
    Type: Grant
    Filed: March 3, 2016
    Date of Patent: September 4, 2018
    Assignee: TOAGOSEI CO., LTD
    Inventor: Naoki Hashimoto
  • Patent number: 10000439
    Abstract: The invention relates to the production of alkyl acrylate according to a continuous transesterification process. In one embodiment the process of the invention uses a simple column to purify a reaction mixture of acryl acrylate in one step yielding alkyl acrylate with a purity of greater than 99.8%.
    Type: Grant
    Filed: December 16, 2013
    Date of Patent: June 19, 2018
    Assignee: Arkema France
    Inventors: Alain F. Riondel, Coralie Graire, Marc Esch, Andre Levray
  • Patent number: 9905769
    Abstract: A process of dissolving [6,6]-phenyl-C60-butyric-N-2-dimethylaminoethyl ester in a solvent to produce a first mixture. A reagent is added to the first mixture to produce a second mixture. The second mixture is then refluxed to produce [6,6]-phenyl-C60-butyric-N-2-trimethylammonium ethyl ester iodide.
    Type: Grant
    Filed: August 24, 2016
    Date of Patent: February 27, 2018
    Assignee: Phillips 66 Company
    Inventors: Joseph Bullock, Brian Worfolk
  • Patent number: 9874811
    Abstract: Provided is a photopolymer composition that may exhibit low volume shrinkage during holographic recording and may prevent a photosensitive dye from remaining unbleached after holographic recording.
    Type: Grant
    Filed: September 9, 2016
    Date of Patent: January 23, 2018
    Assignee: SAMSUNG ELECTRONICS CO., LTD.
    Inventors: Chilsung Choi, Evgeny V. Vasiliev, Vladimir V. Shelkovnikov, Vladimir Loskutov
  • Patent number: 9796650
    Abstract: A process to form a composition comprising an asymmetrical polyene, the asymmetrical polyene comprising an “?,? unsaturated-carbonyl end” and a “C—C double bond end,” the process comprising: reacting an alkene- or polyene-containing alcohol with an alkyl ester of an ?,? unsaturated carboxylic acid in the presence of at least the following components A) through C) to form a solution comprising an asymmetrical polyene: A) a lithium salt; B) a component selected from the group consisting of hydroquinone, an alkyl-substituted phenol, a substituted alkyl-substituted phenol, an alkyl-substituted hydroquinone, a substituted alkyl-substituted hydroquinone, and combinations thereof; and C) an N-oxyl-containing compound; wherein the “?,? unsaturated-carbonyl end” of the asymmetrical polyene is selected from the group consisting of structures a) through c), as described herein, and wherein the “C—C double bond end” of the asymmetrical polyene is selected from the group consisting of structures 1) through 17), as describ
    Type: Grant
    Filed: November 21, 2014
    Date of Patent: October 24, 2017
    Assignees: Dow Global Technologies LLC, Rohn and Haas Company
    Inventors: Robert Wilczynski, Christopher R. Eddy, John O. Osby, Lan T. P. Hoang Nguyen
  • Patent number: 9688601
    Abstract: Process for preparing (meth)acrylates of the formula (I) CH2?C(R1)—CO—O—R2??(I) in which R1 is hydrogen or methyl and R2 is a saturated or unsaturated, linear or branched, aliphatic or cyclic alkyl radical having 6 to 22 carbon atoms, or a (C6-C14)-aryl-(C1-C8)-alkyl radical; by reacting a (meth)acrylate of the formula II CH2?C(R1)—CO—OR3??(II) with an alcohol of the formula (III) HO—R2??(III) in the presence of an amount of a suitable catalyst which catalyzes the reaction and of an amount of a phenolic polymerization inhibitor or a combination of two or more phenolic polymerization inhibitors which is sufficient to inhibit undesired polymerization; the reaction being undertaken with input or introduction into the reaction mixture resulting from the reaction of an amount of oxygen or of an oxygenous gas mixture sufficient to inhibit undesired polymerization, and the process is characterized in that the specific total oxygen input is less than or equal to 1.
    Type: Grant
    Filed: October 27, 2015
    Date of Patent: June 27, 2017
    Assignee: Evonik Roehm GmbH
    Inventors: Joachim Knebel, Ralf Merbach, Guido Protzmann, Klaus Gottmann, John Hirsh, Gerold Schmitt, Dieter Tessmer, Wilhelm Karnbrock, Wolfgang Klesse, Volker Kerscher
  • Patent number: 9670134
    Abstract: Provided is a process for making (2-nitro)alkyl (meth)acrylate compounds of formula I: wherein n, R, R1, R2, R3, R4, R6, R7, and n are as defined herein, by a transesterification reaction between a nitroalcohol compound and a (meth)acrylate compound in the presence of a transesterification catalyst and a free radical inhibitor.
    Type: Grant
    Filed: February 18, 2014
    Date of Patent: June 6, 2017
    Assignee: ANGUS CHEMICAL COMPANY
    Inventors: Muhunthan Sathiosatham, Robert Wilczynski
  • Patent number: 9416092
    Abstract: A transesterification process produces a (meth)acrylate ester product from a mixture comprising an alkyl(meth)acrylate reactant, an alcohol reactant, a catalyst, and a polymerization inhibitor. The mixture is subjected to reaction conditions sufficient to produce a product (meth)acrylate and a product alcohol, which are different than the reactants.
    Type: Grant
    Filed: February 11, 2013
    Date of Patent: August 16, 2016
    Assignee: Rohm and Haas Company
    Inventors: David A. Flosser, Philippe P. Maillot, Nawal K. Sharma, Alejandro Ceron, Mingyu Ye
  • Patent number: 9394224
    Abstract: A transesterification process produces a (meth)acrylate ester product from a mixture comprising an alkyl(meth)acrylate reactant, an alcohol reactant, a catalyst, and a polymerization inhibitor, wherein the water content in the reaction zone at the start of the transesterification step is from 0.2 to 1.1 weight percent, based on the weight of the materials in the reaction zone. The mixture is subjected to reaction conditions sufficient to produce a product (meth)acrylate and a product alcohol, which are different than the reactants.
    Type: Grant
    Filed: February 11, 2013
    Date of Patent: July 19, 2016
    Assignee: Rohm and Haas Company
    Inventors: David A. Flosser, Philippe P. Maillot, Nawal K. Sharma, Alejandro Ceron, Mingyu Ye
  • Patent number: 9353043
    Abstract: In a process for preparing (meth)acrylic esters (E) of polyalkoxy-containing alcohols which comprises reacting polyalkoxy-containing alcohols (P) of formula (I) where R1 is hydrogen, a hydroxyl group or a straight-chain or branched, saturated or unsaturated alcohol of 1 to 30 carbon atoms, R2 and R3 are each independently H or methyl, and m and n are each independently an integer between 0 and 100, with the proviso that m and n cannot both be 0, with a (meth)acrylic anhydride (A) in the presence of at least one basic catalyst (K) having a pKB value of not more than 7.0 and of at least one sterically hindered polymerization inhibitor, the reaction mixture is quenched with a C1-C6 alkanol after the reaction has ended.
    Type: Grant
    Filed: February 12, 2015
    Date of Patent: May 31, 2016
    Assignee: BASF SE
    Inventors: Andrea Misske, Uwe Meisenburg, Jochen Petzoldt, Virginie Bette, Bolette Urtel, Jean-Marc Ballin
  • Patent number: 9296679
    Abstract: The invention relates to the production of 2-octyl acrylate of high purity and in good yield, that includes the recycling of economically upgradable products, such as un-reacted reactants and catalyst. The process uses ethyl titanate in solution in 2-octanol or 2-octyl titanate as a tranesterification catalyst and employs a purification train comprising only two distillation columns.
    Type: Grant
    Filed: January 14, 2013
    Date of Patent: March 29, 2016
    Assignee: Arkema France
    Inventors: Alain Riondel, Coralie Graire, Marc Esch
  • Patent number: 9206270
    Abstract: Process for preparing (meth)acrylates of the formula (I) CH2?C(R1)—CO—O—R2??(I) in which R1 is hydrogen or methyl and R2 is a saturated or unsaturated, linear or branched, aliphatic or cyclic alkyl radical having 6 to 22 carbon atoms, or a (C6-C14)-aryl-(C1-C8)-alkyl radical; by reacting a (meth)acrylate of the formula II CH2?C(R1)—CO—OR3??(II) with an alcohol of the formula (III) HO—R2??(III) in the presence of an amount of a suitable catalyst which catalyzes the reaction and of an amount of a phenolic polymerization inhibitor or a combination of two or more phenolic polymerization inhibitors which is sufficient to inhibit undesired polymerization; the reaction being undertaken with input or introduction into the reaction mixture resulting from the reaction of an amount of oxygen or of an oxygenous gas mixture sufficient to inhibit undesired polymerization, and the process is characterized in that the specific total oxygen input is less than or equal to 1.
    Type: Grant
    Filed: September 29, 2008
    Date of Patent: December 8, 2015
    Assignee: Evonik Roehm GmbH
    Inventors: Joachim Knebel, Ralf Merbach, Guido Protzmann, Klaus Gottmann, John Hirsh, Gerold Schmitt, Dieter Tessmer, Wilhelm Karnbrock, Wolfgang Klesse, Volker Kerscher
  • Patent number: 9018410
    Abstract: The invention relates to the production of 2-octylacrylate of high purity and in good yield using ethyl titanate in solution in 2-octanol or 2-octyl titanate as a transesterification catalyst.
    Type: Grant
    Filed: January 14, 2013
    Date of Patent: April 28, 2015
    Assignee: Arkema France
    Inventors: Alain Riondel, Coralie Graire, Marc Esch, Reinhard Linemann
  • Publication number: 20150045578
    Abstract: A transesterification process produces a (meth)acrylate ester product from a mixture comprising an alkyl(meth)acrylate reactant, an alcohol reactant, a catalyst, and a polymerization inhibitor, wherein the water content in the reaction zone at the start of the transesterification step is from 0.2 to 1.1 weight percent, based on the weight of the materials in the reaction zone. The mixture is subjected to reaction conditions sufficient to produce a product (meth)acrylate and a product alcohol, which are different than the reactants.
    Type: Application
    Filed: February 11, 2013
    Publication date: February 12, 2015
    Applicant: ROHM AND HAAS COMPANY
    Inventors: David A. Flosser, Philippe P. Maillot, Nawal K. Sharma, Alejandro Ceron, Mingyu Ye
  • Patent number: 8940925
    Abstract: The invention relates to a method for producing N,N-dimethylaminoethyl acrylate by the transesterification reaction of an alykl acrylate by N1N-dimethylaminoethanol, and more particularly relates to a method for purifying the azeotropic fraction generated during said reaction, thereby enabling the recycling thereof on the alkyl acrylate production unit. The aim of the method of the invention is in particular to remove the acetaldehyde and the dialkoxyethane contained in the azeotropic fraction, either by the direct distillation of the azeotropic fraction or by the distillation of the aqueous phase resulting from the water scrubbing of the azeotropic fraction.
    Type: Grant
    Filed: January 27, 2010
    Date of Patent: January 27, 2015
    Assignee: Arkema France
    Inventors: Jean-Michel Paul, Coralie Graire, Audrey Riehl
  • Publication number: 20150018573
    Abstract: The present invention describes a method for production of a class of renewable specialty chemicals that may be used for a variety of purposes including as a solvent in the semiconductor industry and as a reagent for commercial chemical production. The precursor compound, PHA, can be produced using various feedstocks such as waste water treatment plant biosolids, distiller's grains and agricultural residual biomass (e.g., corn stover and rice straw). The production of specialty chemicals in tandem with energy production can serve to aid the overall economics of renewable feedstock energy production.
    Type: Application
    Filed: July 13, 2013
    Publication date: January 15, 2015
    Inventors: Zackery Allen McMurry, James Casey Smoot
  • Patent number: 8916724
    Abstract: The present invention relates to a process for preparing (meth)acrylates, comprising the transesterification of a low-boiling ester of (meth)acrylic acid with a reactant alcohol in the presence of catalysts, which is characterized in that the transesterification is catalysed by a basic ion exchanger.
    Type: Grant
    Filed: May 5, 2009
    Date of Patent: December 23, 2014
    Assignee: Evonik Roehm GmbH
    Inventor: Joachim Knebel
  • Publication number: 20140371482
    Abstract: The invention relates to the production of 2-octylacrylate of high purity and in good yield using ethyl titanate in solution in 2-octanol or 2-octyl titanate as a transesterification catalyst.
    Type: Application
    Filed: January 14, 2013
    Publication date: December 18, 2014
    Applicant: Arkema France
    Inventors: Alain Riondel, Coralle Graire, Marc Esch, Reinhard Linemann
  • Patent number: 8889899
    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: Grant
    Filed: May 12, 2006
    Date of Patent: November 18, 2014
    Assignee: Evonik Roehm GmbH
    Inventors: Jochen Ackermann, Alexander May, Udo Gropp, Hermann Siegert, Bernd Vogel, Soenke Broecker
  • Patent number: 8816109
    Abstract: Hexadecyl cis-9-tetradecenoate commonly known as Cetyl myristoleate (CMO) is being used for the treatment of osteoarthritis and other joint inflammatory diseases, cis-9-Tetradecenoic acid (cis-9-myristoleic acid) is the main precursor for the preparation of CMO. As there are limited natural plant sources for cis-9-tetradecenoic acid, the present invention aimed at the synthesis of cis-9-tetradecenoic acid methyl ester from oleic acid methyl ester. As oleic acid is not available in pure form, this has to be isolated from oleic acid-rich oils like olive oil. cis-10-Tetradecenoic acid methyl ester, an isomer of cis-9-tetradecenoic acid was also prepared from undecenoic acid methyl ester, a derivative of castor oil. Undecenoic acid is easily available commercially in pure form.
    Type: Grant
    Filed: January 12, 2010
    Date of Patent: August 26, 2014
    Assignee: Council of Scientific & Industrial Research
    Inventors: Lakshmi Anu Prabhavathi Devi Bethala, Nadpi Gangadhar Katkam, Vijayalakshmi Kunkuma, Ramakrishna Sistla, Madhusudhana Kuncha, Vamanrao Diwan Prakash, Badari Narayana Prasad Rachapudi
  • Patent number: 8692013
    Abstract: A process for making bis(aryloxyalkyl)terephthalates useful as antiplasticizers for thermoplastic polyesters is disclosed. Dimethyl terephthalate is reacted with an excess of an aryloxyalkanol in the presence of a condensation catalyst to produce an intermediate mixture comprising a bis(aryloxyalkyl)terephthalate, a mono(aryloxyalkyl)terephthalate, and unreacted aryloxyalkanol. This mixture continues to react at reduced pressure while unreacted aryloxyalkanol is removed and the mono-ester content is reduced to less than 1 mole % based on the combined amounts of mono- and bis-esters. Both steps are performed substantially in the absence of oxygen. Additional unreacted aryloxyalkanol is then removed to provide a purified bis(aryloxyalkyl)terephthalate having an overall purity of at least 98 mole % and a yellowness index less than 10.
    Type: Grant
    Filed: November 25, 2012
    Date of Patent: April 8, 2014
    Assignee: Stepan Company
    Inventors: Rick Tabor, Brian K. Mirous, Timothy L. Lambert, Michael E. O'Brien, Matthew I. Levinson, Daniel J. Dershowitz
  • Patent number: 8686181
    Abstract: The present invention relates to a process for preparing ethylene glycol dimethacrylate, which comprises transesterification of ethylene glycol with an ester of methacrylic acid in the presence of catalysts, wherein a combination comprising lithium amide (LiNH2) and lithium chloride (LiCl) is used as catalyst. The process of the invention makes it possible to prepare ethylene glycol dimethacrylate particularly inexpensively and in a very high purity.
    Type: Grant
    Filed: May 8, 2008
    Date of Patent: April 1, 2014
    Assignee: Evonik Roehm GmbH
    Inventors: Joachim Knebel, Thorben Schuetz, Guido Protzmann, Harald Trauthwein, Guenther Lauster, Thomas Kehr, Gerhard Koelbl, Guenter Westhaeuser
  • Publication number: 20130338396
    Abstract: This invention provides a method for producing ?,?-unsaturated carboxylic acid esters in high yield from acetone cyanohydrin and sulfuric acid through the separation and concurrent catalytic conversion of reaction side products to additional ?,?-unsaturated carboxylic acid ester product. The catalyst comprises at least one Group IA element and may include a porous support and/or a promoter element selected from at least one of phosphorous, boron, titanium, zinc, zirconium, tin, bismuth, cerium, and alkaline earth metals.
    Type: Application
    Filed: October 4, 2011
    Publication date: December 19, 2013
    Applicant: ROHM AND HAAS COMPANY
    Inventors: Andrew M. Lemonds, Jinsuo Xu
  • Patent number: 8609321
    Abstract: A radiation-sensitive resin composition includes a polymer having a structural unit represented by a formula (I). In the formula (I), R1 represents a hydrogen atom or a methyl group. X represents a bivalent alicyclic hydrocarbon group not having or having a substituent. Y represents a bivalent hydrocarbon group having 1 to 20 carbon atoms. R2 represents a methyl group or a trifluoromethyl group.
    Type: Grant
    Filed: March 8, 2013
    Date of Patent: December 17, 2013
    Assignee: JSP Corporation
    Inventors: Hiromitsu Nakashima, Reiko Kimura, Kazuo Nakahara, Mitsuo Sato
  • Patent number: 8461375
    Abstract: The invention relates to an improved method for the continuous production of alkyl(methyl)acrylates by transesterification of methyl(meth)acrylate with alcohols that are heavy in comparison with methanol. A special processing technique makes it possible to obtain new levels of product quality. Very high space-time-overall yields can also be obtained. The invention is characterized by the multiple use of a homogeneous catalyst which thereby reduces the costs of auxiliary agents significantly.
    Type: Grant
    Filed: November 21, 2003
    Date of Patent: June 11, 2013
    Assignee: Evonik Röhm GmbH
    Inventors: Jochen Ackerman, Horst Hiltner, Hermann Siegert
  • Publication number: 20130090492
    Abstract: This invention is directed to a general catalyst of high activity and selectivity for the production of a variety of esters, particularly acrylate and methacrylate-based esters, by a transesterification reaction. This objective is achieved by reaction of an ester of a carboxylic or a carbonic acid, in particular of a saturated or unsaturated, typically, a 3 to 4 carbon atom carboxylic acid; with an alcohol in the presence of a catalyst comprising the combination of a metal 1,3-dicarbonyl complex (pref. Zn or Fe acetylacetonate) and a salt, in particular an inorganic salt, pref. ZnCl2, LiCI, NaCI, NH4CI or Lil. These catalysts are prepared from readily available starting materials within the reaction medium without the need for isolation (in-situ preparation).
    Type: Application
    Filed: June 10, 2011
    Publication date: April 11, 2013
    Applicant: ECOSYNTH BVBA
    Inventors: Thomas Peter Anne Goossens, Freek Annie Camiel Vrielynck, Noel Gabriel Cornelius Hosten, Koen Jeanne Alfons Van Aken
  • Patent number: 8350081
    Abstract: The invention relates to processes for production of methacrylic acid and to processes for production of methyl methacrylate.
    Type: Grant
    Filed: February 25, 2008
    Date of Patent: January 8, 2013
    Assignee: Evonik Roehm GmbH
    Inventor: Torsten Balduf
  • Patent number: 8344172
    Abstract: A process for making bis(aryloxyalkyl)terephthalates useful as antiplasticizers for thermoplastic polyesters is disclosed. Dimethyl terephthalate is reacted with an excess of an aryloxyalkanol in the presence of a condensation catalyst to produce an intermediate mixture comprising a bis(aryloxyalkyl)terephthalate, a mono(aryloxyalkyl)terephthalate, and unreacted aryloxyalkanol. This mixture continues to react at reduced pressure while unreacted aryloxyalkanol is removed and the mono-ester content is reduced to less than 1 mole % based on the combined amounts of mono- and bis-esters. Both steps are performed substantially in the absence of oxygen. Additional unreacted aryloxyalkanol is then removed to provide a purified bis(aryloxyalkyl)terephthalate having an overall purity of at least 98 mole % and a yellowness index less than 10.
    Type: Grant
    Filed: March 25, 2011
    Date of Patent: January 1, 2013
    Assignee: Stepan Company
    Inventors: Rick Tabor, Brian K. Mirous, Timothy L. Lambert, Michael E. O'Brien, Matthew I. Levinson, Daniel J. Dershowitz
  • Patent number: 8309755
    Abstract: The invention relates to a process in which a compound R1COOR3 (I) is made by a transesterification reaction of an ester compound R1COOR2 (II) with an alcohol R3OH (III) in the presence of a transesterification catalyst, wherein R1 is H or C1-4 alkyl or CH2?CR4—; R2 is C1-4 alkyl; R3 is selected from the group consisting of alkyl having at least 4 carbon atoms, cycloalkyl having at least 5 carbon atoms, aryl, aralkyl, alkaryl and amino alkyl; and R4 is —H or —C1-4 alkyl, wherein alcohol R2OH (IV) is formed as a byproduct and in which said byproduct (IV) is removed by distillation in the presence of an entrainer, in which the entrainer is a compound that suppresses the formation of an azeotrope between compound (II) and byproduct (IV). The process can be useful in the preparation of esters such as dimethyl amino ethyl (meth)acrylate. The invention also provides a method of separating alcohols and esters.
    Type: Grant
    Filed: April 22, 2011
    Date of Patent: November 13, 2012
    Assignee: BASF SE
    Inventors: John Colin Dunn, Dinesh Mistry, Martin Gower, Roger Prétôt, Markus Schmid
  • Patent number: 8288583
    Abstract: The present invention relates to processes for preparing carboxylic acid derivatives, comprising the reaction of at least one carboxylic acid and/or of a carboxylic acid derivative with at least one alcohol and/or an amine in the presence of a metal-containing catalyst, wherein, after the reaction has ended, the metal-containing catalyst is contacted with water and a superabsorbent, the contacting of the catalyst with the water leading to hydrolysis of the catalyst. The present invention further relates to the use of superabsorbents for removing a metal-containing catalyst from a mixture after hydrolysis of the catalyst.
    Type: Grant
    Filed: June 1, 2007
    Date of Patent: October 16, 2012
    Assignee: Evonik Rohmax Additives GmbH
    Inventors: Uwe Boehmke, Klaus Schimossek, Detlef Bloos, Michael Neusius, Stephan Massoth, Guenther Graeff, Alexander Dardin, Matthias Fischer, Volker Stephan
  • Patent number: 8278077
    Abstract: The present invention relates to a process for preparing (meth)acrylic esters of alcohols having C—C triple bonds, to processes for their preparation, and to their use.
    Type: Grant
    Filed: July 31, 2006
    Date of Patent: October 2, 2012
    Assignee: BASF Aktiengesellschaft
    Inventors: Dietmar Haering, Uwe Meisenburg, Bernhard Hauer, Frank Dietsche
  • Patent number: 8247500
    Abstract: A polymeric resin comprising guanidine groups having at least one C4-C22 tertiary alkyl substituent.
    Type: Grant
    Filed: February 3, 2009
    Date of Patent: August 21, 2012
    Assignee: Rohm and Haas Company
    Inventors: Rajiv Manohar Banavali, Alfred Karl Schultz
  • Publication number: 20120123148
    Abstract: The present invention relates to a composition including a dialkyl tin oxide, such as DBTO, which can be used as a transesterification catalyst for the synthesis of (meth)acrylic esters. The invention also relates to a method for the synthesis of (meth)acrylic esters by transesterification in the presence of said composition.
    Type: Application
    Filed: May 18, 2010
    Publication date: May 17, 2012
    Applicant: Arkema France
    Inventors: Jean-Michel Paul, Boris Tonnelier, Francis Augustin
  • Publication number: 20120088707
    Abstract: The invention relates to alkyl(meth)acrylates comprising a long linear chain bearing alkyl ramifications corresponding to general formula (I): in which R1 is a hydrogen atom or a methyl radical and R2 is a long alkyl chain of formula (II): R(CH2—CH2)n(CH2—CH(R3))m— in which R is a methyl or ethyl radical, R3 is an linear- or branched-chain alkyl radical containing from 1 to 6 carbon atoms, n=9 to 20, m=1 to 5, wherein it is possible for the —CH2—CH2— and —CH2—CH(R3)— units to be distributed in block or random form. These compounds can in particular be used for the production of additives intended to lower the settings point of paraffinic oils or fuels (diesel oils or fuel oils), and for the production of additives for lubricants.
    Type: Application
    Filed: October 4, 2007
    Publication date: April 12, 2012
    Applicant: Arkema France
    Inventor: Jean-Michel Paul
  • Publication number: 20120077977
    Abstract: The present invention relates to a process for preparing (meth)acrylic esters (F) of N,N-substituted amino alcohols, by transesterifying N,N-substituted amino alcohols (I) in which Y and Z are each independently C1-C20-alkyl, C3-C15-cycloalkyl, aryl, or Y and Z together with the nitrogen atom connecting them form a 5- to 9-membered saturated heterocyclic radical which optionally has oxygen, sulfur, nitrogen or C1-C4-alkyl-substituted nitrogen as a further heteroatom, and X is C2-C20-alkylene which may be interrupted by 1 to 10 nonadjacent oxy groups and/or unsubstituted or methoxy-substituted C1-C4-alkylimino groups, or a C3-C15-cycloalkylene, with at least one (meth)acrylic ester (D) in the presence of at least one heterogeneous catalyst (K), wherein the heterogeneous catalyst (K) is used without any further solvent and the content of polymerization inhibitors in the reaction mixture is <450 ppm, and to the use of the (meth)acrylic esters (F) of N,N-substituted amino alcohols.
    Type: Application
    Filed: September 20, 2011
    Publication date: March 29, 2012
    Applicant: BASF SE
    Inventors: Virginie Bette, Hermann Bergmann, Jochen Petzoldt, Frank Höfer
  • Patent number: 8129563
    Abstract: The present invention relates to a process for preparing allyl methacrylate, comprising the reaction of allyl alcohol with an ester of methacrylic acid, wherein the reaction is catalyzed by zirconium acetylacetonate. The process according to the invention enables particularly favorable preparation of allyl methacrylate with a very high purity.
    Type: Grant
    Filed: May 8, 2008
    Date of Patent: March 6, 2012
    Assignee: Evonik Roehm GmbH
    Inventors: Bardo Schmitt, Guido Protzmann, Thorben Schuetz, Harald Trauthwein, Reinhold Martin, Joachim Knebel, Ingo Sander, Klaus Gottmann, Thomas Kehr, Dieter Bathen, Christian Maul
  • Patent number: 8119832
    Abstract: In one embodiment, an alkyl ester production system can comprise: a first transesterification reactor comprising a liquid biomass inlet located between a liquid glycerol outlet and a liquid alkyl ester outlet, a water wash vessel comprising an alkyl ester inlet, a water inlet located near a top of the water wash vessel, and a washed alkyl ester outlet located near the top of the water wash vessel, wherein the alkyl ester inlet is located near a bottom of the water wash vessel, and a drier comprising a washed alkyl ester inlet located near a top of the drier, and a gas inlet and a dried alkyl ester outlet located near the bottom of the drier. The first transesterification reactor can be configured for laminar flow and for liquid reactants and products. The alkyl ester inlet can be in fluid communication with the washed alkyl ester outlet.
    Type: Grant
    Filed: April 28, 2009
    Date of Patent: February 21, 2012
    Assignee: The University of Connecticut
    Inventors: Richard Parnas, Clifford Weed, Nicholas Leadbeater
  • Patent number: 8067633
    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)3Ti]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: Grant
    Filed: November 30, 2007
    Date of Patent: November 29, 2011
    Assignee: Arkema France
    Inventor: Jean-Michel Paul
  • Patent number: 8049030
    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: Grant
    Filed: May 8, 2008
    Date of Patent: November 1, 2011
    Assignee: Evonik Röhm GmbH
    Inventors: Guido Protzmann, Harald Trauthwein, Joachim Knebel, Thorben Schuetz, Gerhard Koelbl, Thomas Kehr, Guenther Lauster
  • Patent number: 8039664
    Abstract: The present invention relates to a process for preparing butanediol dimethacrylates, which comprises the transesterification of butanediol with an ester of methacrylic acid in the presence of catalysts, wherein a combination comprising at least one lithium compound and at least one calcium compound is used as catalyst, at least one of the compounds of lithium and/or of calcium is an oxide, a hydroxide, an alkoxide having from 1 to 4 carbon atoms or a carboxylate having from 1 to 4 carbon atoms and at least part of the reaction is carried out in the presence of an effective amount of water. The process of the invention makes a particularly inexpensive preparation of butanediol dimethacrylates having a very high purity possible.
    Type: Grant
    Filed: May 8, 2008
    Date of Patent: October 18, 2011
    Assignee: Evonik Roehm GmbH
    Inventors: Joachim Knebel, Thorben Schuetz, Harald Trauthwein, Thomas Kehr, Guenther Lauster, Guido Protzmann, Gerhard Koelbl, Guenter Westhaeuser
  • Publication number: 20110201839
    Abstract: The invention relates to a process in which a compound R1COOR3 (I) is made by a transesterification reaction of an ester compound R1COOR2 (II) with an alcohol R3OH (III) in the presence of a transesterification catalyst, wherein R1 is H or C1-4 alkyl or CH2?CR4—; R2 is C1-4 alkyl; R3 is selected from the group consisting of alkyl having at least 4 carbon atoms, cycloalkyl having at least 5 carbon atoms, aryl, aralkyl, alkaryl and amino alkyl; and R4 is —H or —C1-4 alkyl, wherein alcohol R2OH (IV) is formed as a byproduct and in which said byproduct (IV) is removed by distillation in the presence of an entrainer, in which the entrainer is a compound that suppresses the formation of an azeotrope between compound (II) and byproduct (IV). The process can be useful in the preparation of esters such as dimethyl amino ethyl (meth)acrylate. The invention also provides a method of separating alcohols and esters.
    Type: Application
    Filed: April 22, 2011
    Publication date: August 18, 2011
    Inventors: John Colin DUNN, Dinesh MISTRY, Martin GOWER, Roger PRÉTÓT, Markus SCHMID
  • Patent number: 7999130
    Abstract: The present invention relates to processes for preparing alkyl (meth)acrylates, comprising the steps of transesterifying an alkyl ?-hydroxycarboxylate with (meth)acrylic acid to obtain alkyl (meth)acrylates and ?-hydroxycarboxylic acid, and dehydrating the ?-hydroxycarboxylic acid to obtain (meth)acrylic acid.
    Type: Grant
    Filed: May 12, 2006
    Date of Patent: August 16, 2011
    Assignee: Evonik Roehm GmbH
    Inventors: Jochen Ackermann, Alexander May, Udo Gropp, Hermann Siegert, Bernd Vogel, Soenke Broecker
  • Patent number: 7999131
    Abstract: The invention relates to a process in which a compound R1COOR3 (I) is made by a transesterification reaction of an ester compound R1COOR2 (II) with an alcohol R3OH (III) in the presence of a transesterification catalyst, wherein R1 is H or C1-4 alkyl or CH2?CR4—; R2 is C1-4 alkyl; R3 is selected from the group consisting of alkyl having at least 4 carbon atoms, cycloalkyl having at least 5 carbon atoms, aryl, aralkyl, alkaryl and amino alkyl; and R4 is —H or —C1-4 alkyl, wherein alcohol R2OH (IV) is formed as a byproduct and in which said byproduct (IV) is removed by distillation in the presence of an entrainer, in which the entrainer is a compound that suppresses the formation of an azeotrope between compound (II) and byproduct (IV). The process can be useful in the preparation of esters such as dimethyl amino ethyl(meth)acrylate. The invention also provides a method of separating alcohols and esters.
    Type: Grant
    Filed: November 9, 2006
    Date of Patent: August 16, 2011
    Assignee: BASF SE
    Inventors: John Colin Dunn, Dinesh Mistry, Martin Gower, Roger Prétôt, Markus Schmid
  • Publication number: 20110130590
    Abstract: The present invention relates to a process for preparing (meth)acrylates, comprising the transesterification of a low-boiling ester of (meth)acrylic acid with a reactant alcohol in the presence of catalysts, which is characterized in that the transesterification is catalysed by a basic ion exchanger.
    Type: Application
    Filed: May 5, 2009
    Publication date: June 2, 2011
    Applicant: Evonik Roehm GmbH
    Inventor: Joachim Knebel
  • Patent number: RE49610
    Abstract: A transesterification catalyst that is heterogeneous and a method for preparing said transesterification catalyst are provided. The catalyst can be used in a variety of transesterification reactor configurations including CSTR (continuous stirred tank reactors), ebullated (or ebullating) beds or any other fluidized bed reactors, and PFR (plug flow, fixed bed reactors). The catalyst can be used for manufacturing commercial grade biodiesel, biolubricants and glycerin.
    Type: Grant
    Filed: September 14, 2020
    Date of Patent: August 15, 2023
    Assignee: CRYSTAPHASE PRODUCTS, INC.
    Inventors: Umakant Pravinchandra Joshi, Peter Gregory Ham