Formation Of Ethylenic Unsaturation Patents (Class 562/599)
  • Patent number: 10562834
    Abstract: A process to prepare a compound of Formula (I) wherein R3, R4 and R5 are each selected independently from hydrogen, halogen, alkyl, alkenyl, alkynyl, alkoxyl, and wherein the alkyl, alkenyl, alkynyl, and alkoxyl may be optionally substituted with one or more halogen, alkyl, alkenyl, alkynyl, and alkoxyl.
    Type: Grant
    Filed: January 4, 2019
    Date of Patent: February 18, 2020
    Assignee: Intervet Inc.
    Inventors: Michael Berger, Stephan Veit, Hans Peter Niedermann, Tobias Kappesser, Alfred Stutz
  • Patent number: 10487035
    Abstract: Methods for making acrylic acid, acrylic acid derivatives, or mixtures thereof by contacting a stream containing hydroxypropionic acid, hydroxypropionic acid derivatives, or mixtures thereof with either an active catalyst containing an amorphous and partially-dehydrated phosphate salt or a precursor catalyst containing a crystalline phosphate salt in a reactor with a low corrosion rate are provided.
    Type: Grant
    Filed: January 4, 2018
    Date of Patent: November 26, 2019
    Assignee: The Procter & Gamble Company
    Inventors: Dimitris Ioannis Collias, Jane Ellen Godlewski, Juan Esteban Velasquez
  • Patent number: 10464875
    Abstract: The present invention relates to a process for the production of an ethylenically unsaturated carboxylic acid or ester, preferably ?,ß ethylenically unsaturated carboxylic acids or esters, by the liquid phase reaction of formaldehyde or a suitable source thereof with a non-cyclic carboxylic acid ester in the presence of a basic metal salt.
    Type: Grant
    Filed: April 12, 2016
    Date of Patent: November 5, 2019
    Assignee: LUCITE INTERNATIONAL UK LIMITED
    Inventors: Graham Ronald Eastham, David William Johnson, Mark Waugh, Jonathan Ainsley Iggo, Michael Beaumont
  • Patent number: 10239819
    Abstract: A method for producing esters of an alpha, beta-unsaturated carboxylic acid are disclosed, the method includes reacting a three or four carbon beta-hydroxyalkanoate composition or mixtures thereof with a mono-alcohol under heating conditions to form a reaction product and distilling the reaction product to recover a composition containing at least fifty percent by weight of the ester of the alpha, beta-unsaturated carboxylic acid.
    Type: Grant
    Filed: October 15, 2015
    Date of Patent: March 26, 2019
    Assignee: CARGILL, INCORPORATED
    Inventors: Timothy Walter Abraham, Ravi R. Gokarn
  • Patent number: 10106481
    Abstract: Hydroxypropionic acid, hydroxypropionic acid derivatives, or mixtures thereof are dehydrated using a catalyst and a method to produce bio-acrylic acid, acrylic acid derivatives, or mixtures thereof. A method to produce the dehydration catalyst is also provided.
    Type: Grant
    Filed: August 29, 2016
    Date of Patent: October 23, 2018
    Assignee: The Procter & Gamble Company
    Inventors: Juan Esteban Velasquez, Dimitris Ioannis Collias, Jane Ellen Godlewski, Fred Christian Wireko
  • Patent number: 9630900
    Abstract: The invention relates to a process for dehydrating aqueous 3-hydroxypropionic acid to acrylic acid in the liquid phase, wherein aqueous acrylic acid is removed continuously from the liquid phase and the liquid phase comprises an inert organic solvent 1.
    Type: Grant
    Filed: September 2, 2014
    Date of Patent: April 25, 2017
    Assignee: BASF SE
    Inventors: Tim Blaschke, Ortmund Lang, Nicolai Tonio Wörz, Christian Raith, Marco Hartmann, Marta Zajaczkowski-Fischer
  • Patent number: 9598345
    Abstract: The present invention relates to a method for producing an unsaturated-acid ester or an unsaturated acid, containing a step of reacting a compound (1) represented by the following formula (1) with a compound represented by the following formula (2) (excluding the compound (1)) in the presence of a Lewis acid catalyst at a temperature of the boiling point of the compound (1) or higher and 350° C. or lower, thereby obtaining products including a compound represented by the following formula (3): (in formula (1) and formula (3), R1, R2 and R4 each independently may be hydrogen atom or an alkyl group, R3 and R5 each independently are hydrogen atom or a deuterium atom, and X is a halogen atom; in formula (2) and formula (3), R6 may be hydrogen atom, an alkyl group or an aryl group, and R7 is hydrogen atom or a deuterium atom).
    Type: Grant
    Filed: January 8, 2016
    Date of Patent: March 21, 2017
    Assignee: ASAHI GLASS COMPANY, LIMITED
    Inventors: Tomoyuki Fujita, Koichi Murata, Naoko Shirota, Yusuke Suzuki, Daisuke Jomuta
  • Patent number: 9561479
    Abstract: An apparatus for producing a mixed solution, comprising a mixing vessel for preparing an aqueous mixed solution containing a dicarboxylic acid and a Nb compound and a filter for the aqueous mixed solution connected to the mixing vessel via a pipe, the mixing vessel being anticorrosive and equipped with a stirring unit, a heating unit and a cooling unit for the aqueous mixed solution, wherein the aqueous mixed solution prepared in the mixing vessel is fed to the filter via the pipe and filtered in the filter under increased pressure.
    Type: Grant
    Filed: January 31, 2012
    Date of Patent: February 7, 2017
    Assignee: ASAHI KASEI CHEMICALS CORPORATION
    Inventors: Yusuke Ishii, Takaaki Kato
  • Patent number: 9546123
    Abstract: The present invention relates to a process for preparing acrylic acid from formaldehyde and acetic acid, comprising reacting formaldehyde and acetic acid via an aldol condensation in a reaction unit comprising n reaction zones arranged in series, each comprising an aldol condensation catalyst, where n is at least 2, and wherein at least one stream leaving a reaction zone, before being fed into the reaction zone immediately downstream, is mixed with a stream comprising formaldehyde and optionally comprising acetic acid. The present invention further relates to an apparatus for preparing acrylic acid from formaldehyde and acetic acid and to the use of this apparatus.
    Type: Grant
    Filed: December 17, 2015
    Date of Patent: January 17, 2017
    Assignee: BASF SE
    Inventors: Till Christian Brueggemann, Nicolai Tonio Woerz, Astrid Ruppel
  • Patent number: 9493390
    Abstract: The invention relates to a catalyst composition comprising a mixed oxide of vanadium, titanium, and phosphorus. The titanium component is derived from a water-soluble, redox-active organo-titanium compound. The catalyst composition is highly effective at facilitating the vapor-phase condensation of formaldehyde with acetic acid to generate acrylic acid, particularly using an industrially relevant aqueous liquid feed. Additionally, the catalyst composition is catalytically active towards the formation of acrylic acid from methylene diacetate and methacrylic acid from methylene dipropionate; both reactions are carried out with high space time yields.
    Type: Grant
    Filed: February 19, 2015
    Date of Patent: November 15, 2016
    Assignee: EASTMAN CHEMICAL COMPANY
    Inventors: Venkata Bharat Ram Boppana, David William Norman, Melissa Page Steffey
  • Patent number: 9487466
    Abstract: In one embodiment, the invention is to process for producing acrylics. The process includes the steps of contacting a crude product stream with an extraction agent mixture at a temperature less than 50° C.
    Type: Grant
    Filed: December 16, 2011
    Date of Patent: November 8, 2016
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventors: Craig J. Peterson, R. Jay Warner, Josefina T. Chapman
  • Patent number: 9120743
    Abstract: The invention relates to a process for producing an acrylate product comprising the step of reacting a reaction gas mixture A comprising methanol and oxygen to form a product gas mixture A. The process may further comprise the step of combining at least a portion of the product gas mixture A and acetic acid to form a reaction gas mixture B. The process may further comprise the step of reacting at least a portion of the acetic acid in the reaction gas input mixture B with at least a portion of the formaldehyde in the reaction gas input mixture B to form a product gas mixture B. The process may further comprise the step of separating at least a portion of the product gas mixture B to form an alkylenating agent stream comprising at least 1 wt % alkylenating agent and an intermediate acrylate product stream comprising acrylate product.
    Type: Grant
    Filed: June 27, 2013
    Date of Patent: September 1, 2015
    Assignee: Celanese International Corporation
    Inventors: Craig J. Peterson, Elizabeth Bowden, Josefina T. Chapman, Sean Mueller, Dick Nagaki, Tianshu Pan, Himanshu Lodha
  • Patent number: 9115070
    Abstract: A process for preparing acrylic acid from ethylene oxide and carbon monoxide, in which ethylene oxide is carbonylated in an aprotic solvent with carbon monoxide in the presence of a cobalt catalyst system to give poly-3-hydroxypropionate, the cobalt content in the poly-3-hydroxypropionate formed is reduced with the aid of water and/or an aqueous solution as a precipitation and/or wash liquid, and the poly-3-hydroxypropionate is subsequently split by thermolysis to give acrylic acid.
    Type: Grant
    Filed: July 16, 2013
    Date of Patent: August 25, 2015
    Assignee: BASF SE
    Inventors: Marek Pazicky, Christian Raith, Rocco Paciello, Raphael Heinrich Brand, Marco Hartmann, Klaus Joachim Mueller-Engel, Peter Zurowski, Wolfgang Fischer
  • Publication number: 20150105584
    Abstract: Lactic acid, lactic acid derivatives, or mixtures thereof are dehydrated using a catalyst and process to produce bio-acrylic acid, acrylic acid derivatives, or mixtures thereof. A method to produce the catalyst is also provided.
    Type: Application
    Filed: October 16, 2014
    Publication date: April 16, 2015
    Inventors: Juan Esteban Velasquez, Dimitris Ioannis Collias, Jane Ellen Godlewski, Janette Villalobos Lingoes
  • Patent number: 8993801
    Abstract: The invention relates to a catalyst composition comprising a mixed oxide of vanadium, titanium, and phosphorus. The titanium component is derived from a water-soluble, redox-active organo-titanium compound. The catalyst composition is highly effective at facilitating the vapor-phase condensation of formaldehyde with acetic acid to generate acrylic acid, particularly using an industrially relevant aqueous liquid feed. Additionally, the catalyst composition is catalytically active towards the formation of acrylic acid from methylene diacetate and methacrylic acid from methylene dipropionate; both reactions are carried out with high space time yields.
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: March 31, 2015
    Assignee: Eastman Chemical Company
    Inventors: Venkata Bharat Ram Boppana, David William Norman, Melissa Dawn Page
  • Publication number: 20150080606
    Abstract: Described herein are methods for preparing methacrylic acid from biobased starting materials.
    Type: Application
    Filed: September 16, 2014
    Publication date: March 19, 2015
    Inventor: JOSHUA LENSBOUER
  • Patent number: 8962515
    Abstract: In one embodiment, the invention is to a process for producing an acrylate product. The process includes the steps of contacting an alkanoic acid and an alkylenating agent over a catalyst composition under conditions effective to produce the acrylate product. The catalyst composition comprises a metal phosphate matrix containing vanadium and bismuth. Preferably, the catalyst comprises, in an active phase, vanadium to bismuth at a molar ratio of at least 0.02:1. Preferably, the catalyst composition is substantially free of titanium.
    Type: Grant
    Filed: October 31, 2012
    Date of Patent: February 24, 2015
    Assignee: Celanese International Corporation
    Inventors: Dick Nagaki, Craig J. Peterson, Heiko Weiner, Elizabeth Bowden, Josefina T. Chapman, Sean Mueller
  • Patent number: 8957250
    Abstract: Disclosed herein is an improved process for the catalytic dehydration of lactic acid to acrylic acid. More particularly, the present invention discloses catalytic dehydration of lactic acid to acrylic acid with high selectivity and yield for acrylic acid using calcium phosphate (CP) catalyst with varying Ca/P ratio optionally modified with 5 wt % sodium.
    Type: Grant
    Filed: May 16, 2012
    Date of Patent: February 17, 2015
    Assignee: Council of Scientific & Industrial Research
    Inventors: Mohan Keraba Dongare, Shubhangi Bhalchandra Umbarker, Samadhan Tanaji Lomate
  • Publication number: 20150038735
    Abstract: An L-type zeolite, a modified L-type zeolite, or any combination thereof may be useful in catalytically preparing ?,?-unsaturated carboxylic acids and/or esters thereof through reaction pathways that include dehydroxylation reactions and optionally esterification reactions. In some reaction pathways, dehydroxylation reactions and esterification reactions may be performed sequentially or concurrently.
    Type: Application
    Filed: September 6, 2013
    Publication date: February 5, 2015
    Inventors: Cenan A. Ozmeral, Joseph P. Glas, Rajesh Dasari, Setrak Tanielyan, Ramesh Deoram Bhagat, Mohan Reddy Kasireddy, Ramnik Singh, Vijay Gnanadesikan, Robert L. Augustine, Santosh More
  • Publication number: 20150031912
    Abstract: Processes for the catalytic dehydration of hydroxypropionic acid, hydroxypropionic acid derivatives, or mixtures thereof to acrylic acid, acrylic acid derivatives, or mixtures thereof with high yield and selectivity and without significant conversion to undesired side products, such as, acetaldehyde, propanoic acid, and acetic acid, are provided.
    Type: Application
    Filed: October 10, 2014
    Publication date: January 29, 2015
    Inventors: Jane Ellen Godlewski, Janette Villalobos, Dimitris Ioannis Collias, Juan Estaban Velasquez
  • Publication number: 20150031913
    Abstract: Processes for the catalytic dehydration of hydroxypropionic acid, hydroxypropionic acid derivatives, or mixtures thereof to acrylic acid, acrylic acid derivatives, or mixtures thereof with high yield and selectivity and without significant conversion to undesired side products, such as, acetaldehyde, propanoic acid, and acetic acid, are provided.
    Type: Application
    Filed: October 10, 2014
    Publication date: January 29, 2015
    Inventors: Jane Ellen Godlewski, Janette Villalobos, Dimitris Ioannis Collias, Juan Estaban Velasquez
  • Patent number: 8940924
    Abstract: The invention relates to a catalyst for the reaction of formaldehyde with a carboxylic acid or ester to produce an ethylenically unsaturated carboxylic acid or ester, preferably ?, ? ethylenically unsaturated carboxylic acids or ester. The catalyst includes a metal oxide having at least two types of metal cations, M1 and M2, wherein M1 is at least one metal selected from group 3 or 4 in the 4th to 6th periods of the periodic table, group 13 in the 3rd to 5th periods of the periodic table, or the remaining elements in the lanthanide series and M2 is at least one metal selected from group 5 in the 5th or 6th periods of the periodic table or group 15 in the 4th or 5th periods of the periodic table. The production includes reacting formaldehyde with a carboxylic acid or esterin the presence of the catalyst effective to catalyze the reaction.
    Type: Grant
    Filed: June 24, 2011
    Date of Patent: January 27, 2015
    Assignee: Lucite International UK Limited
    Inventors: David William Johnson, Sabina Ziemian
  • Publication number: 20150025272
    Abstract: The invention relates to a catalyst composition comprising a mixed oxide of vanadium, titanium, and phosphorus modified with alkali metal. The titanium component is derived from a water-soluble, redox-active organo-titanium compound. The catalyst composition is highly effective at facilitating the vapor-phase condensation of formaldehyde with acetic acid to generate acrylic acid, particularly using an industrially relevant aqueous liquid feed.
    Type: Application
    Filed: October 8, 2014
    Publication date: January 22, 2015
    Applicant: Eastman Chemical Company
    Inventors: David William Norman, Greg Alan King
  • Patent number: 8933179
    Abstract: A method of producing a compound of formula (i): wherein R=H or CH3 the method comprising exposing a source of a compound of formula (ii) to reaction conditions of temperature and pressure: formula (ii) wherein R is defined as above wherein, when R=CH3, the source of a compound of formula (ii) is exposed to reaction conditions of temperature and pressure while being in a liquid phase.
    Type: Grant
    Filed: December 21, 2010
    Date of Patent: January 13, 2015
    Assignee: Lucite International UK Limited
    Inventors: David William Johnson, Graham Ronald Eastham, Martyn Poliakoff, Thomas Andrew Huddle
  • Publication number: 20140364644
    Abstract: A process for producing a crude product stream including an acrylate product and an alkylenating agent and separating at least a portion of the crude product stream to form alkylenating agent and intermediate product streams. The alkylenating agent stream comprises at least 1 wt % alkylenating agent and the intermediate product stream comprises acrylate products in high concentration. The crude product stream is formed by contacting acetic acid and formaldehyde in the presence of at least one aldol condensation catalyst under conditions effective to form the stream. Catalysts which are particularly useful are multielement oxide active materials of the general formula V1PbFecX1dX2eOn.
    Type: Application
    Filed: June 5, 2013
    Publication date: December 11, 2014
    Inventors: Dick Nagaki, Craig J. Peterson, Josefina T. Chapman, Sean Mueller
  • Publication number: 20140364645
    Abstract: A method of producing an ethylenically unsaturated, typically, an ?, ? ethylenically unsaturated carboxylic acid or ester is described. The method comprises the steps of contacting formaldehyde, or a source of formaldehyde, with a carboxylic acid or ester in the presence of a catalyst and optionally in the presence of an alcohol. The catalyst comprises barium phosphate leaf or plate shaped/like crystals, or a source thereof. A catalyst system is also described. The catalyst system comprises a crystalline barium phosphate catalyst and optionally a catalyst support.
    Type: Application
    Filed: January 14, 2013
    Publication date: December 11, 2014
    Applicant: Lucite International UK Limited
    Inventors: Ian Andrew York, Sabina Ziemian
  • Patent number: 8895683
    Abstract: In one aspect, a process for the preparation of a superabsorbent polymer is described herein. In some embodiments, the process comprises (I) preparing acrylic acid, wherein the process comprises (a1) provision of a fluid F1 having a composition comprising from about 5 to about 20 wt. % of hydroxypropionic acid, salts thereof, or mixtures thereof; from about 0.1 to about 5 wt. % of inorganic salts; from about 0.1 to about 30 wt. % of organic compounds which differ from hydroxypropionic acid; from 0 to about 50 wt. % of solids; and from about 20 to about 90 wt. % of water; (a2) dehydration of said hydroxypropionic acid to give a fluid F2 containing acrylic acid; and (a3) purification of said fluid F2 to give a purified acrylic acid phase comprising acrylic acid having a purity of at least 70 wt. %; and (II) polymerizing the acrylic acid of (I) to form a superabsorbent polymer.
    Type: Grant
    Filed: May 17, 2013
    Date of Patent: November 25, 2014
    Assignee: Evonik Degussa GmbH
    Inventors: Franz-Felix Kuppinger, Axel Hengstermann, Guido Stochniol, Gunther Bub, Jurgen Mosler, Andreas Sabbagh
  • Publication number: 20140343319
    Abstract: In a process for preparing acrylic acid, a reaction gas which comprises a gaseous formaldehyde source and gaseous acetic acid and in which the partial pressure of the formaldehyde source, calculated as formaldehyde equivalents, is at least 85 mbar and in which the molar ratio of the acetic acid to the formaldehyde source, calculated as formaldehyde equivalents, is at least 1 is contacted with a solid condensation catalyst. The space-time yield can be enhanced significantly by increasing the partial pressure of the reactants. The space-time yield remains high even after prolonged process duration.
    Type: Application
    Filed: May 14, 2014
    Publication date: November 20, 2014
    Applicant: BASF SE
    Inventors: Michael GOEBEL, Christian Walsdorff, Marco Hartmann, Nicolai Tonio Woerz, Tim Blaschke, Philipp Gruene
  • Publication number: 20140343318
    Abstract: Process for preparing a vinylidenecarboxylic acid or ester thereof, wherein a reaction gas comprising gaseous formaldehyde, molecular oxygen and an alkycarboxylic acid or ester thereof is brought into contact with a solid catalyst whose active composition comprises a vanadium-phosphorus oxide having an average oxidation state of vanadium of from +4.40 to +5.0 to give a product gas comprising the vinylidenecarboxylic acid or ester thereof.
    Type: Application
    Filed: May 14, 2014
    Publication date: November 20, 2014
    Applicant: BASF SE
    Inventors: Philipp GRUENE, Cornelia Katharina DOBNER, Marco HARTMANN
  • Patent number: 8889586
    Abstract: In one embodiment, the invention is to a catalyst composition, comprising vanadium and titanium. Preferably, the molar ratio of vanadium to titanium in an active phase of the catalyst composition is greater than 0.5:1.
    Type: Grant
    Filed: January 8, 2014
    Date of Patent: November 18, 2014
    Assignee: Celanese International Corporation
    Inventors: Dick Nagaki, Heiko Weiner, Josefina T. Chapman, Mark O. Scates, Alexandra S. Locke, Craig J. Peterson
  • Patent number: 8884050
    Abstract: Processes for the catalytic dehydration of hydroxypropionic acid, hydroxypropionic acid derivatives, or mixtures thereof to acrylic acid, acrylic acid derivatives, or mixtures thereof with high yield and selectivity and without significant conversion to undesired side products, such as, acetaldehyde, propanoic acid, and acetic acid, are provided.
    Type: Grant
    Filed: February 6, 2013
    Date of Patent: November 11, 2014
    Assignee: The Procter & Gamble Company
    Inventors: Jane Ellen Godlewski, Janette Villalobos, Dimitris Ioannis Collias, Juan Estaban Velasquez
  • Patent number: 8877966
    Abstract: A process for preparing acrylic acid from methanol and acetic acid, in which, in a reaction zone A, the methanol is partially oxidized to formaldehyde in a heterogeneously catalyzed gas phase reaction, the product gas mixture A obtained and an acetic acid source are used to obtain a reaction gas input mixture B which comprises acetic acid and formaldehyde and has the acetic acid in excess over the formaldehyde, and the formaldehyde present in reaction gas input mixture B is aldol-condensed to acrylic acid under heterogeneous catalysis in a reaction zone B with acetic acid present in reaction gas input mixture B, and unconverted acetic acid still present alongside the acrylic acid target product in the product gas mixture B obtained is removed therefrom, and the acetic acid removed is recycled into the production of reaction gas input mixture B.
    Type: Grant
    Filed: September 15, 2011
    Date of Patent: November 4, 2014
    Assignee: BASF SE
    Inventors: Stefanie Herzog, Stefan Altwasser, Klaus Joachim Mueller-Engel
  • Patent number: 8864950
    Abstract: A process for producing an acrylate product. The process comprises the step of providing a crude product stream comprising the acrylate product and an alkylenating agent. The process further comprises the step of separating at least a portion of the crude product stream to form an alkylenating agent stream and an intermediate product stream. The alkylenating agent stream comprises at least 1 wt % alkylenating agent and the intermediate product stream comprises acrylate product. The separating is performed in at least one column at an operating pressure ranging from 40 kPa to 80 kPa.
    Type: Grant
    Filed: January 6, 2012
    Date of Patent: October 21, 2014
    Assignee: Celanese International Corporation
    Inventors: Craig Peterson, Josefina Chapman, Jonathan Gallacher
  • Publication number: 20140275575
    Abstract: The present application provides a method for producing an beta-lactone product. The method includes the steps of: reacting an epoxide, a solvent with a carbonylation catalyst and carbon monoxide to produce a reaction stream comprising a beta-lactone then separating a portion of the beta-lactone in the reaction stream from the solvent and carbonylation catalyst to produce: i) a beta-lactone stream with the beta-lactone, and ii) a catalyst recycling stream including the carbonylation catalyst and the high boiling solvent; and adding the catalyst recycling stream to the feed stream.
    Type: Application
    Filed: May 12, 2014
    Publication date: September 18, 2014
    Applicant: Novomer, Inc.
    Inventors: Scott D. Allen, Ronald R. Valente, Han Lee, Anna E. Cherian, Donald L. Bunning, Nye A. Clinton, Olan Stanley Fruchey, Bernard Duane Dombek
  • Publication number: 20140271488
    Abstract: Synthesis of compounds having varying degrees of conformational rigidity is obtained via a low cost, high yield and efficient synthetic reactions. The library of compounds is structurally diverse having at least one or more chiral centers and providing large numbers of compounds having building block diversity and substantial scaffold diversity. The compounds further provide a novel method for obtaining candidate therapeutic agents for prevention, treatment or diagnosis of diseases.
    Type: Application
    Filed: September 7, 2012
    Publication date: September 18, 2014
    Applicant: The Scripps Research Institute
    Inventors: Glenn C. Micalizio, Thomas Kodadek, Mohosin Sarkar
  • Patent number: 8835518
    Abstract: A process for the reactivation of an acidic ion exchange resin is described. The invention relates to the treatment of an at least partially deactivated resin which has been deactivated by contact with an impure ethylenically unsaturated acid or ester containing target impurities. The reactivation includes the step of contacting the at least partially deactivated resin with an alcohol to thereby increase the activity thereof. The invention extends to reactivating a resin deactivated by contact with an impure ethylenically unsaturated acid, ester or nitrile containing target impurities by contacting the at least partially deactivated resin with an alcohol and a carboxylic acid to thereby increase the activity thereof. A reactivated resin and a process for preparing and purifying an ethylenically unsaturated acid or ester of the following formula: —R1—C(?(CH2)m)—COOR2 are also described.
    Type: Grant
    Filed: March 25, 2010
    Date of Patent: September 16, 2014
    Assignee: Lucite International UK Limited
    Inventor: Trevor Huw Morris
  • Patent number: 8829238
    Abstract: A method for synthesizing a deuterated acrylate of the Formula (1), the method comprising: (i) deuterating a propiolate compound of Formula (2) to a methyne-deuterated propiolate compound of Formula (3) in the presence of a base and D2O: and (ii) reductively deuterating the methyne-deuterated propiolate compound of Formula (3) in a reaction solvent in the presence of deuterium gas and a palladium-containing catalyst to afford the deuterated acrylate of the Formula (1). The resulting deuterated acrylate compounds, derivatives thereof, and polymers derived therefrom are also described.
    Type: Grant
    Filed: September 12, 2012
    Date of Patent: September 9, 2014
    Assignee: UT-Battelle, LLC
    Inventors: Jun Yang, Peter V. Bonnesen, Kunlun Hong
  • Patent number: 8821804
    Abstract: The invention relates to the use of monoliths as particle filters for limiting the deactivation of catalysts during catalytic reactions in multi-tubular reactors. The invention is particularly well-suited for catalytic oxidation reactions in the gaseous phase. The invention also relates to multi-tubular reactors including monoliths as particle filters.
    Type: Grant
    Filed: July 23, 2008
    Date of Patent: September 2, 2014
    Assignee: Arkema France
    Inventor: Jean-Luc Dubois
  • Patent number: 8802585
    Abstract: In one embodiment, the invention is to a catalyst composition comprising vanadium and titanium. The catalyst composition has a surface area of at least 22.6 m2/g and a plurality of pores, and the plurality of pores have a pore diameter of less than 11.9 nm.
    Type: Grant
    Filed: September 22, 2011
    Date of Patent: August 12, 2014
    Assignee: Celanese International Corporation
    Inventors: Heiko Weiner, Josefina T. Chapman, Alexandra S. Locke, Craig T. Peterson, Mark O. Scates, Dick Nagaki
  • Patent number: 8796475
    Abstract: The present application provides a method for producing an beta-lactone product. The method includes the steps of: reacting an epoxide, a solvent with a carbonylation catalyst and carbon monoxide to produce a reaction stream comprising a beta-lactone then separating a portion of the beta-lactone in the reaction stream from the solvent and carbonylation catalyst to produce: i) a beta-lactone stream with the beta-lactone, and ii) a catalyst recycling stream including the carbonylation catalyst and the high boiling solvent; and adding the catalyst recycling stream to the feed stream.
    Type: Grant
    Filed: April 10, 2013
    Date of Patent: August 5, 2014
    Assignee: Novomer, Inc.
    Inventors: Scott D. Allen, Ronald R. Valente, Han Lee, Anna E. Cherian, Donald L. Bunning, Nye A. Clinton, Olan Stanley Fruchey, Bernard Duane Dombek
  • Publication number: 20140213811
    Abstract: The present invention relates to the production of acrolein, acrylic acid or methacrylic acid by dehydration reaction of renewable raw material such as glycerin or hydroxycarboxylic acids, in the presence of a novel catalyst system supported on a carrier having a bimodal structure and a high pore volume and distribution. The dehydration reactions can be carried out for longer operation duration, so that acrolein, acrylic acid or methacrylic acid can be produced at higher productivity and for longer running time.
    Type: Application
    Filed: July 27, 2012
    Publication date: July 31, 2014
    Inventors: Jean-Luc Dubois, Kimito Okumura, Yasushi Kobayashi, Ryota Hiraoka
  • Patent number: 8772539
    Abstract: An appropriate catalyst is found for synthesis of an unsaturated carboxylic acid and/or a derivative thereof using as a raw material compound a hydroxycarboxylic acid and/or a derivative thereof that can easily be synthesized from a polysaccharide such as biomass-derived cellulose, and an efficient method for synthesizing the unsaturated carboxylic acid and/or the derivative thereof is provided. This method is a method for synthesizing an unsaturated carboxylic acid and/or a derivative thereof, wherein an apatite compound is used as a catalyst to synthesize the unsaturated carboxylic acid and/or the derivative thereof from a biomass-derived hydroxycarboxylic acid and/or a derivative thereof by a dehydration reaction.
    Type: Grant
    Filed: October 25, 2010
    Date of Patent: July 8, 2014
    Assignees: Kabushiki Kaisha Sangi, Kochi University
    Inventors: Ayumu Onda, Yumiko Matsuura, Kazumichi Yanagisawa
  • Patent number: 8765629
    Abstract: The invention relates to a catalyst composition comprising a mixed oxide of vanadium, titanium, and phosphorus. The titanium component is derived from a water-soluble, redox-active organo-titanium compound. The catalyst composition is highly effective at facilitating the vapor-phase condensation of formaldehyde with acetic acid to generate acrylic acid, particularly using an industrially relevant aqueous liquid feed.
    Type: Grant
    Filed: September 16, 2011
    Date of Patent: July 1, 2014
    Assignee: Eastman Chemical Company
    Inventors: David William Norman, Gerald Charles Tustin, Michael James Nash, Liu Deng, Theresa Sims Barnette
  • Publication number: 20140171681
    Abstract: A method for preparing an unsaturated carboxylic acid comprising (a) preparing an aqueous solution comprising an ammonium salt of hydroxycarboxylic acid and a salt of inorganic acid; (b) contacting the aqueous solution with a cation exchange resin to prepare a conversion aqueous solution comprising a hydroxycarboxylic acid and an inorganic acid; and (c) dehydrating the hydroxycarboxylic acid using the inorganic acid as a catalyst is provided.
    Type: Application
    Filed: December 5, 2013
    Publication date: June 19, 2014
    Applicant: Samsung Electronics Co. Ltd.
    Inventors: Jun CHWAE, Nam Soo Park, Moo Ho Lee, Jong Won Kim
  • Publication number: 20140171685
    Abstract: A catalytic reactor including a chamber (1) and separation means (2) arranged inside the chamber (1), said separation means defining at least one reaction area (3) and at least one regeneration area (4), the reaction area (3) being supplied with a reaction flow (15, 16) and connected, at the outlet thereof, to a first gas tapping device (13), the regeneration area (4) being supplied with a regeneration flow (17) and connected, at the outlet thereof, to a second gas tapping device (10), the reactor being suitable for including a fluidized bed of catalyst particles (5) in the reaction area (3), the separation means (2) enabling the catalyst particles to pass from the reaction area (3) to the regeneration area (4), and the reactor making it possible to move catalyst particles into the regeneration area (4) so as to enable the return thereof to the reaction area (3).
    Type: Application
    Filed: July 9, 2012
    Publication date: June 19, 2014
    Applicant: ARKEMA FRANCE
    Inventors: Jean-Luc Dubois, Grégory Patience
  • Publication number: 20140171684
    Abstract: In one embodiment, the invention is directed to a process for producing an acrylate product. The process comprises the step of reacting in a reactor a reaction mixture comprising an alkanoic acid and a liquid alkylenating agent source comprising methanol in an amount less than 0.5 wt. % over a catalyst and under conditions effective to form a crude acrylate product comprising acrylate product and alkylenating agent. The process further comprises the step of separating at least a portion of the crude acrylate product to form at least one alkylenating agent stream and at least one purified acrylate product stream comprising acrylate product.
    Type: Application
    Filed: December 19, 2012
    Publication date: June 19, 2014
    Applicant: CELANESE INTERNATIONAL CORPORATION
    Inventors: Sean Mueller, Dick Nagaki, Craig J. Peterson, Josefina T. Chapman
  • Publication number: 20140155653
    Abstract: Disclosed herein is an improved process for the catalytic dehydration of lactic acid to acrylic acid. More particularly, the present invention discloses catalytic dehydration of lactic acid to acrylic acid with high selectivity and yield for acrylic acid using calcium phosphate (CP) catalyst with varying Ca/P ratio optionally modified with 5 wt % sodium.
    Type: Application
    Filed: May 16, 2012
    Publication date: June 5, 2014
    Inventors: Mohan Keraba Dongare, Shubhangi Bhalchandra Umbarker, Samadhan Tanaji Lomate
  • Patent number: 8735314
    Abstract: In one embodiment, the invention is to a catalyst composition comprising vanadium and titanium. The catalyst composition further comprises ethylene glycol and citric acid. Preferably, the catalyst composition is substantially free of oxalic acid and lactic acid.
    Type: Grant
    Filed: September 29, 2011
    Date of Patent: May 27, 2014
    Assignee: Celanese International Corporation
    Inventors: Dick Nagaki, Craig Peterson, Mark Scates, Heiko Weiner, Josefina T. Chapman, Alexandra S. Locke
  • Publication number: 20140135527
    Abstract: In one embodiment, the invention is to a catalyst composition, comprising vanadium and titanium. Preferably, the molar ratio of vanadium to titanium in an active phase of the catalyst composition is greater than 0.5:1.
    Type: Application
    Filed: January 8, 2014
    Publication date: May 15, 2014
    Applicant: Celanese International Corporation
    Inventors: Dick Nagaki, Heiko Weiner, Josefina T. Chapman, Mark O. Scates, Alexandra S. Locke, Craig J. Peterson
  • Publication number: 20140128636
    Abstract: In one embodiment, the invention is to a process for producing an acrylate product. The process comprises the step of providing a crude product stream comprising the acrylate product and an alkylenating agent. The process further comprises the step of separating at least a portion of the crude product stream to form an alkylenating agent stream and an intermediate product stream. The alkylenating agent stream comprises at least 1 wt % alkylenating agent and the intermediate product stream comprises acrylate product.
    Type: Application
    Filed: January 9, 2014
    Publication date: May 8, 2014
    Applicant: Celanese International Corporation
    Inventors: Craig J. Peterson, Josefina T. Chapman, Ilias S. Kotsianis, Sean Mueller, Dick Nagaki, Tianshu Pan