Purification Or Recovery Patents (Class 560/218)
  • Patent number: 10723689
    Abstract: Using a vertical multi-tube heat exchanger which includes a tubular body, an upper tube plate and a lower tube plate, a plurality of heat transfer tubes, and lid sections and in which the distillation gas introduced into a receiving chamber is cooled in the course of passing through the heat transfer tube and turns into a condensate, a solution containing polymerization inhibitor is introduced into the receiving chamber. Some of the plurality of heat transfer tubes have an upper end protruding above the upper tube plate, with the remainings being not protruding, and the solution containing polymerization inhibitor coming into contact with the distillation gas in the receiving chamber forms a liquid flow layer with a predetermined liquid depth on the upper tube plate.
    Type: Grant
    Filed: December 27, 2018
    Date of Patent: July 28, 2020
    Assignee: Mitsubishi Chemical Corporation
    Inventor: Yasushi Ogawa
  • Patent number: 10597350
    Abstract: The present invention provides methods comprising distilling a reaction mixture of methacrolein and methanol used to make methyl methacrylate (MMA) in the presence of one or more strong or inorganic acids, the mixture comprising an aqueous organic component mixture of all of water, MMA, methacrolein methanol and acetals or hemiacetals of methacrolein to remove the acetals or hemiacetals of methacrolein to a level of 100 ppm or below, based on the amount of methyl methacrylate. The method reduces the amount of acetals or hemiacetals of methacrolein to well below equilibrium levels and eliminates the need for additional downstream distillation to refine the product of the reaction.
    Type: Grant
    Filed: May 15, 2017
    Date of Patent: March 24, 2020
    Assignee: Dow Global Technologies LLC
    Inventor: William G. Worley
  • Patent number: 10435335
    Abstract: An object of the present invention is to provide a method for suppressing the precipitation of polymers with a high concentration dissolved in a solvent in the operation termination step and suppressing the blockage of the apparatus by the polymers even when the polymers with a high concentration are precipitated, and the invention relates to a method for producing an ?-olefin low polymer comprising a production operation step and an operation termination step, wherein the supply position of a supply liquid to a distillation column in the operation termination step is changed to a position lower than the supply position of a supply liquid to the distillation column in the production operation step.
    Type: Grant
    Filed: September 25, 2017
    Date of Patent: October 8, 2019
    Inventor: Hiroki Emoto
  • Patent number: 9796651
    Abstract: The present invention relates to methods by which the thermal dissociation of Michael adducts present in a stream of crude acrylic acid, called “crude ester grade”, and the esterification reaction of acrylic acid present in the stream of crude acrylic acid, or generated in situ by thermal dissociation, with a light alcohol, are carried out simultaneously.
    Type: Grant
    Filed: July 24, 2014
    Date of Patent: October 24, 2017
    Assignee: Arkema France
    Inventors: Michel Fauconet, Roger L. Roundy, Stephane Denis, Samuel M. Daniel
  • Patent number: 9403751
    Abstract: The invention relates to a liquid-liquid extraction process, comprising: the provision of a main input liquid stream, comprising at least one compound of interest and an excess compound; the provision of a liquid scrubbing stream; the extraction of the excess compound from the main input liquid stream by contact with the liquid scrubbing stream, making it possible to collect a main output liquid stream, depleted in excess compound with respect to the main input liquid stream; in which: the main input liquid stream and the liquid scrubbing stream exhibit a difference in density of less than or equal to 50 kg/m3 and also an interfacial tension of less than or equal to 3 dyn/cm; and the extraction stage is carried out in a packed contactor with a ratio by weight as input liquid scrubbing stream/main liquid stream ranging from 0.3 to 0.5.
    Type: Grant
    Filed: September 23, 2014
    Date of Patent: August 2, 2016
    Assignee: Arkema France
    Inventors: Serge Tretjak, Stephane Denis
  • Patent number: 9067880
    Abstract: This invention provides a process for reducing biacetyl in alpha-, beta-unsaturated carboxylic acid esters, particularly in acrylic or methacrylic (hereinafter “(meth)acrylic”) esters, which comprise low levels of weak acid.
    Type: Grant
    Filed: October 13, 2011
    Date of Patent: June 30, 2015
    Inventors: Michael A. Curtis, David A. Flosser, Jamie J. Juliette, Philippe P. Maillot, Donna Williams
  • Publication number: 20150087857
    Abstract: The invention relates to a liquid-liquid extraction process, comprising: the provision of a main input liquid stream, comprising at least one compound of interest and an excess compound; the provision of a liquid scrubbing stream; the extraction of the excess compound from the main input liquid stream by contact with the liquid scrubbing stream, making it possible to collect a main output liquid stream, depleted in excess compound with respect to the main input liquid stream; in which: the main input liquid stream and the liquid scrubbing stream exhibit a difference in density of less than or equal to 50 kg/m3 and also an interfacial tension of less than or equal to 3 dyn/cm; and the extraction stage is carried out in a packed contactor with a ratio by weight as input liquid scrubbing stream/main liquid stream ranging from 0.3 to 0.5.
    Type: Application
    Filed: September 23, 2014
    Publication date: March 26, 2015
    Applicant: Arkema France
    Inventors: Serge TRETJAK, Stephane DENIS
  • Publication number: 20150045579
    Abstract: A method for separating the components of a mixture containing methyl methacrylate, water, and methanol in which the mixture is dehydrated in a first stage membrane unit, producing a dehydrated mixture. Methanol in the dehydrated mixture is removed in a second stage membrane unit, producing a retentate stream containing methyl methacrylate and substantially no said methanol.
    Type: Application
    Filed: August 9, 2013
    Publication date: February 12, 2015
    Inventors: Shiguang LI, Shaojun ZHOU, Miao YU
  • Publication number: 20150038736
    Abstract: A vertical centrifugal thin film evaporator is equipped with: a cylindrical body in which an central axis of a circle is set in a vertical direction; a rotor that rotates an interior of the cylindrical body in a circumferential direction thereof; a wiper that slides on an inner circumferential surface of the cylindrical body; a fixing support that fixes the wiper and is mounted on the rotor; and a heater that heats a circumferential surface of the cylindrical body. A liquid-withdrawing structure that communicates between a space surrounded by the wiper and the fixing support and a space outside the wiper and the fixing support is formed on at least one of the wiper and the fixing support, thereby preventing a liquid to be processed from being retained between the wiper and the fixing support.
    Type: Application
    Filed: February 5, 2013
    Publication date: February 5, 2015
    Applicant: Mitsubishi Rayon Co., Ltd.
    Inventors: Junichi Morioka, Shuhei Otsuka
  • 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
  • Patent number: 8907121
    Abstract: A process for purifying methyl methacrylate (MMA) is described. The process involves contacting liquid MMA having impurities therein with a sulphonic acid resin, in the presence of formaldehyde or a suitable source of methylene or ethylene of formula I. R5 and R6 are independently selected from C1-C12 hydrocarbons or H; X is either O or S; n is an integer from, 1 to 100; and m is 1 or 2: The compound of formula I may be suitable source of formaldehyde.
    Type: Grant
    Filed: December 11, 2009
    Date of Patent: December 9, 2014
    Assignee: Lucite International UK Limited
    Inventors: David William Johnson, Trevor Huw Morris
  • Patent number: 8859804
    Abstract: Disclosed is a method for producing a (meth)acrylate ester wherein a high purity (meth)acrylate ester is obtained with a high yield, with a reduced loss of (meth)acrylic acid anhydride. In the method, (meth)acrylic acid is recovered with a high yield, and the (meth)acrylate ester is purified easily. Specifically disclosed is a method for producing a (meth)acrylate ester which comprises: (1) a step of producing (meth)acrylic acid anhydride by reacting a specific fatty acid anhydride and (meth)acrylic acid, while removing a by-produced fatty acid; (2) a step of obtaining a (meth)acrylate ester by reacting an alcohol and unpurified (meth)acrylic acid anhydride obtained in step (1) preferably at a temperature not less than 90° C.; and (3) a step of recovering (meth)acrylic acid by distillation preferably at a temperature not less than 90° C. The method may also comprise a step of heating or distilling the reaction liquid obtained in step (2) at a temperature not less than 90° C.
    Type: Grant
    Filed: February 4, 2010
    Date of Patent: October 14, 2014
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Ryuichi Ansai, Hiroyuki Nogami, Kuniyoshi Ogura
  • Patent number: 8846840
    Abstract: Provided according to the present invention are an adamantyl (meth)acrylate represented by formula (1), having a formazin standard turbidity of less than 1.7 NTU (Nephelometric Turbidity Unit) in methylethylketone or tetrahydrofuran, and also a (meth)acrylic copolymer comprising the adamantyl (meth)acrylate as a repeating unit: (in the formula, R1 represents hydrogen or a methyl group; R2 through R4 each independently represent a hydrogen atom, a hydroxyl group, an alkyl group having a carbon number of 1 to 3, an aryl group, an alkoxy group, an aryloxy group, a halogen group, an alkyl halide group, or a hydroxyalkyl group; and n1 represents 0 or 1).
    Type: Grant
    Filed: March 29, 2011
    Date of Patent: September 30, 2014
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Kikuo Furukawa, Toshiharu Yamashita, Yoshio Nishimura
  • Publication number: 20140275614
    Abstract: A method is provided for the production and purification of carboxylic betaine-based zwitterionic vinyl monomers, such as (meth)acrylic or (meth)acrylamide monomer containing a betaine-type group of the formula: wherein A is an ester, amide, benzyl, pyridinyl, or imidazolyl; R is hydrogen or methyl; and n is an integer from 0 to 10. The method involves the reaction of acrylic acid with aminoalkyl (meth)acrylate or N-amino-alkyl (meth)acrylamide having a basic tertiary nitrogen atom in the presence of a free radical inhibitor, this reaction leads to a betaine:acid complex that can be either separated from the reaction media into pure betaine:acid complex powder or further purified into pure monomer powder by passing the reaction mixture through a base resin followed by precipitation in a nonsolvent or direct precipitation in a nonsolvent containing an organic base.
    Type: Application
    Filed: March 14, 2014
    Publication date: September 18, 2014
    Applicant: Zwitter Technology, LLC
    Inventors: Yuting Li, Hong Xue, Yingquan Song
  • Publication number: 20140275613
    Abstract: Various embodiments of the present invention include systems and methods for converting free fatty acids to ethyl esters. An exemplary method may comprise contacting the free fatty acid with a non-polar solvent. A mineral acid and an alcohol may then be added to form a two-phase mixture. An aqueous phase my subsequently be removed from the mixture. The processes and methods may be used in the manufacture of supplements, pharmaceuticals, cosmetic and beauty products, feedstocks, and the like.
    Type: Application
    Filed: September 12, 2013
    Publication date: September 18, 2014
    Applicant: Aurora Algae, Inc.
    Inventors: Jeffrey Gerard Hippler, Louis Anthony Kapicak, Kristen Potter
  • Publication number: 20140243551
    Abstract: The present invention relates to a new method for isolating ingenol (C20H28O5) from mixtures of diterpenoid esters and ingenol esters in a single step. Ingenol isolated by means of this method can be used as a precursor for the synthesis of biologically active ingenol derivatives, such as ingenol-3-angelate and ingenol-3-tigliate.
    Type: Application
    Filed: October 2, 2012
    Publication date: August 28, 2014
    Inventors: Maria Luz Bellido Cabello De Alba, Giovanni Appendino, Alberto Pagani, Eduardo Munoz Blanco
  • Patent number: 8802889
    Abstract: A process for production of allyl acetate includes steps of reacting acetic acid 3, oxygen 1 and propylene 2 in the presence of a catalyst in an oxidation reactor 5 to form allyl acetate and water; separating the unreacted acetic acid by a distillation column 9; and recovering an acetic acid-containing liquid which contains acetic acid and returning the acetic acid-containing liquid to the oxidation reactor 5 via an acetic acid-water evaporator 4, the process further including a heating step of heating a process liquid which contains the acetic acid-containing liquid to a temperature of 80 to 250° C. by a heater.
    Type: Grant
    Filed: September 20, 2011
    Date of Patent: August 12, 2014
    Assignee: Showa Denko K.K.
    Inventor: Wataru Oguchi
  • Patent number: 8772534
    Abstract: The present invention provides a method of recovering a (meth)acrylic acid ester, which comprises the steps of: (a) carrying out an esterification reaction between an alcohol and (meth)acrylic acid in the presence of a catalyst to obtain a (meth)acrylic acid ester, wherein a byproduct is generated together with the (meth)acrylic acid ester; and (b) subjecting the byproduct generated in step (a) to a reaction with a catalyst and water in a reactor, wherein the water is fed into the reactor in order that water content exceeds 0 wt % but is 10 wt % or less in the reactor based on the total weight of reactants comprising the byproduct, the catalyst and the water, and thereby separating the (meth)acrylic acid, the alcohol and the (meth)acrylic acid ester contained in the byproduct from the byproduct to obtain the (meth)acrylic acid, the alcohol and the (meth)acrylic acid ester as a recovered product.
    Type: Grant
    Filed: November 19, 2009
    Date of Patent: July 8, 2014
    Assignee: LG Chem, Ltd.
    Inventors: Se-Won Baek, Hyun-Kyu Kim, Jun-Seok Ko, Kyoung-Su Ha, Sung-Koo Park, Dong-Hyun Woo
  • Publication number: 20140135523
    Abstract: A continuous process for preparing (meth)acrylates of C10-alcohol mixtures by reaction of glacial (meth)acrylic acid with an isomer mixture of C10-alcohols composed of 2-propylheptanol as the main isomer and at least one of the C10-alcohols 2-propyl-4-methylhexanol, 2-propyl-5-methylhexanol, 2-isopropylheptanol, 2-isopropyl-4-methylhexanol, 2-isopropyl-5-methylhexanol and/or 2-propyl-4,4-dimethylpentanol, and the use of a diester of dicarboxylic acids which have been esterified with N-oxyl-containing compounds as polymerization inhibitors in such a process.
    Type: Application
    Filed: September 27, 2013
    Publication date: May 15, 2014
    Applicant: BASF SE
    Inventors: Ulrich JAEGER, Volker SCHLIEPHAKE, Ortmund LANG, Jochen PETZOLDT, Tobias Johannes KORN, Virginie BETTE, Claus HECHLER
  • Publication number: 20140128465
    Abstract: The present invention includes methods for producing and purifying esters of polyunsaturated fatty acids that include reacting a composition having triglycerides with polyunsaturated fatty acid residues in the presence of an alcohol and a base to produce an ester of a polyunsaturated fatty acid from the triglycerides. The composition can be a polyunsaturated fatty acid-containing composition that has not been conventionally processed. The reacted composition can be further processed by distillation.
    Type: Application
    Filed: January 13, 2014
    Publication date: May 8, 2014
    Inventors: Krishna Raman, Jung Lee, Neil Leininger, Chris Luigart
  • Patent number: 8609886
    Abstract: An industrially advantageous method for producing a high purity terminal olefin is disclosed, comprising the steps of (a) contacting a mixture comprising a terminal olefin represented by formula (1): and one or more corresponding internal olefins as impurities, with a brominating agent in the presence of water or an alcohol, to convert the internal olefin(s) to compound(s) having a higher boiling point than the terminal olefin; and (b) purifying the terminal olefin by distillation from the reaction mixture.
    Type: Grant
    Filed: January 8, 2010
    Date of Patent: December 17, 2013
    Assignee: Kuraray Co., Ltd.
    Inventors: Kei Miyoshi, Goro Asanuma
  • Patent number: 8592624
    Abstract: A production process for the manufacture of ethylenically unsaturated acids or esters thereof is described. The process includes the steps of reaction of an alkanoic acid, or ester of an alkanoic acid, of the formula R3—CH2—COOR4 where R3 and R4 are each independently hydrogen or an alkyl group, in the presence of a catalyst system to produce an ethylenically unsaturated acid or ester product. The process is characterised in that the acid or ester product is subsequently contacted with a dienophile to thereby remove discolouration therefrom. An ethylenically unsaturated acid or ester crude product purification process is also described.
    Type: Grant
    Filed: May 15, 2009
    Date of Patent: November 26, 2013
    Assignee: Lucite International UK Limited
    Inventors: David William Johnson, Trevor Huw Morris
  • Publication number: 20130217914
    Abstract: This invention provides a process for reducing biacetyl in alpha-, beta-unsaturated carboxylic acid esters, particularly in acrylic or methacrylic (hereinafter “(meth)acrylic”) esters, which comprise low levels of weak acid.
    Type: Application
    Filed: October 13, 2011
    Publication date: August 22, 2013
    Applicant: ROHM AND HAAS COMPANY
    Inventors: Michael A. Curtis, David A. Flosser, Jamie J. Juliette, Philippe P. Maillot, Donna Williams
  • Publication number: 20130158288
    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: Application
    Filed: December 16, 2011
    Publication date: June 20, 2013
    Applicant: CELANESE INTERNATIONAL CORPORATION
    Inventors: Craig J. Peterson, R. Jay Warner, Josefina T. Chapman
  • Patent number: 8455675
    Abstract: A solution component recovery method, a solution component recovery apparatus, and an impregnation process/impregnation component recovery system for separating a first component from a second component. The separation between the first and second components is accomplished by reducing the pressure on a solution that contains the first component, which results in the solidification of the first component in the solution at a temperature that is equal to or higher than a predetermined solidification temperature. The second component, in which the first component is dissolved, is evaporated at a temperature range that is less than the predetermined solidification temperature. The evaporated second component is then recovered by a cooling step.
    Type: Grant
    Filed: April 28, 2010
    Date of Patent: June 4, 2013
    Assignees: Aisin AW Co., Ltd., Sutai Co., Ltd., Kansai Chemical Engineering Co., Ltd.
    Inventors: Hiroyuki Kawatsu, Naoshi Ito, Yasuhiko Sugino, Mitsuo Yamamoto, Hideo Noda, Goro Nishimura
  • Patent number: 8394982
    Abstract: A process for purifying an unsaturated compound, where purification is performed in a plant with evaporators.
    Type: Grant
    Filed: August 29, 2008
    Date of Patent: March 12, 2013
    Assignee: Evonik Röhm GmbH
    Inventors: Benedikt Laux, Christian Maul, Volker Schleep, Ingo Sander
  • Publication number: 20130006012
    Abstract: A method of refining a natural oil includes: (a) providing a feedstock that includes a natural oil; (b) reacting the feedstock in the presence of a metathesis catalyst to form a metathesized product that includes olefins and esters; (c) passivating residual metathesis catalyst with an agent selected from the group consisting of (i) a salt and/or an ester of a phosphorous oxo acid, (ii) a derivative of the phosphorous oxo acid in which at least one P—H bond has been replaced by a P—C bond, (iii) a salt and/or an ester of the derivative, and (iv) combinations thereof; (d) separating the olefins in the metathesized product from the esters in the metathesized product; and (e) transesterifying the esters in the presence of an alcohol to form a transesterified product and/or hydrogenating the olefins to form a fully or partially saturated hydrogenated product.
    Type: Application
    Filed: December 22, 2011
    Publication date: January 3, 2013
    Inventors: Bruce E. Firth, Sharon E. Kirk
  • Patent number: 8324424
    Abstract: The invention relates in general terms to a process for preparing to a process for purifying an alkyl methacrylate, comprising the steps of: A. providing an alkyl methacrylate with an impurity: B. adsorbing at least some of the impurity onto a purifying solid to obtain an ultrapure alkyl methacrylate, to a process for preparing an ultrapure alkyl methacrylate, to an apparatus for preparing alkyl methacrylates, to a process for preparing a polymer based at least partly on alkyl methacrylates, to the use of an alkyl methacrylate obtained according to the invention in chemical products, and to chemical products comprising an alkyl methacrylate obtained according to the invention.
    Type: Grant
    Filed: August 31, 2007
    Date of Patent: December 4, 2012
    Assignee: Evonik Röhm GmbH
    Inventors: Udo Gropp, Robert Weber, Thomas Schaefer, Andreas Perl, Rudolf Sing, Thomas Mertz
  • Patent number: 8304573
    Abstract: A method of recovering pyrolysis products of resin of the present invention includes cooling gaseous pyrolysis products generated from pyrolysis of the resin in a pyrolysis tank to recover the resin as liquid pyrolysis products. The method includes the following steps (1) to (4): (1) continuously feeding fluidization gas, heated solid particles, and a resin into the pyrolysis tank to fluidize the solid particles and the resin by the fluidization gas; (2) continuously feeding the resin into the pyrolysis tank from a position which is ½ or less of the height of a solid particle layer in the pyrolysis tank in a stationary state; (3) continuously discharging the solid particles from a position lower than the height of a feeding position of the resin; and (4) heating the discharged solid particles in a heating furnace and then feeding the heated solid particles into the pyrolysis tank.
    Type: Grant
    Filed: March 7, 2008
    Date of Patent: November 6, 2012
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Akinobu Sasaki, Nobuyuki Kikuya, Takashi Ookubo, Masahiro Hayashida
  • Patent number: 8198475
    Abstract: The present invention provides an efficient production method suitable to industrial-scale production not requiring column purification for adamantyl (meth)acrylates having an adamantine skeleton having utility in crosslinked resins, optical fibers, optical waveguides, optical disc substrates and other optical materials.
    Type: Grant
    Filed: December 16, 2009
    Date of Patent: June 12, 2012
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Kikuo Furukawa, Yoshihisa Arai
  • Patent number: 8183406
    Abstract: The present invention provides a method for extractive recovery and conversion of selected compounds, such as methacrylic acid (MAA) and 2-methacrylamide (MAM), from a stream derived from purification of methyl methacrylate (MMA) or methacrylic acid (MAA) produced via a conventional ACH route process.
    Type: Grant
    Filed: September 13, 2010
    Date of Patent: May 22, 2012
    Inventors: Andrew M. Lemonds, Jinsuo Xu
  • Patent number: 8173832
    Abstract: Provided is a method capable of solving the problems associated with production of LVSA, which is a pheromone produced by female pest mealybugs, and is useful as an agrochemical pest, at an industrial large scale, and producing LVSA in a high yield. Specifically, the present invention provides a production method of 2-isopropenyl-5-methyl-4-hexen-1-yl 3-methyl-2-butenoate, comprising reacting senecioic acid with a halogenating agent to give senecioic acid halide, reacting the obtained senecioic acid halide with 2-isopropenyl-5-methyl-4-hexen-1-ol in the presence of an organic base compound and heat treating the obtained crude 2-isopropenyl-5-methyl-4-hexen-1-yl 3-methyl-2-butenoate in the presence of a basic substance at 50-250° C.
    Type: Grant
    Filed: March 28, 2007
    Date of Patent: May 8, 2012
    Assignee: Kuraray Co., Ltd.
    Inventors: Katsuji Ujita, Keisuke Saeki
  • Patent number: 8157969
    Abstract: Accumulation of polymer on equipment, which is in contact with polymerizable material during normal process operation, is minimized by the method and apparatus of the present invention. The method involves positioning and affixing the equipment, such as a pressure relief device, to process apparatus, such as a distillation column, proximate to a wetted region comprising liquid phase fluid in the process apparatus, such that the moving liquid phase fluid is at least intermittently in contact with the equipment and one or more of accumulated polymerizable material, condensate comprising same, and polymer, is washed off of the equipment.
    Type: Grant
    Filed: April 26, 2007
    Date of Patent: April 17, 2012
    Assignee: Rohm and Haas Company
    Inventors: Barnett John O., Michael Stanley DeCourcy, Michael W. Hurley
  • Publication number: 20120029229
    Abstract: An industrially advantageous method for producing a high purity terminal olefin is disclosed, comprising the steps of (a) contacting a mixture comprising a terminal olefin represented by formula (1): and one or more corresponding internal olefins as impurities, with a brominating agent in the presence of water or an alcohol, to convert the internal olefin(s) to compound(s) having a higher boiling point than the terminal olefin; and (b) purifying the terminal olefin by distillation from the reaction mixture.
    Type: Application
    Filed: January 8, 2010
    Publication date: February 2, 2012
    Applicant: KURARAY CO., LTD.
    Inventors: Kei Miyoshi, Goro Asanuma
  • Publication number: 20110306783
    Abstract: The present invention relates to a composition which comprises at least one hydroxyalkyl(meth)acrylate and has been stabilized for a purification, which comprises hydroquinone monomethyl ether and 4-hydroxy-2,2,6,6-tetramethylpiperidine N-oxyl. The present invention additionally describes processes for purifying and for preparing hydroxyalkyl(meth)acrylates. A further aspect of the present invention is a composition which is obtainable by the processes mentioned.
    Type: Application
    Filed: February 25, 2010
    Publication date: December 15, 2011
    Applicant: Evonik Roehm GmbH
    Inventors: Dirk Broell, Benedikt Laux, Christian Maul, Thorben Schuetz, Bardo Schmitt, Volker Schleep, Claus Zimmer
  • Publication number: 20110282023
    Abstract: A process for purifying methyl methacrylate (MMA) is described. The process involves contacting liquid MMA having impurities therein with a sulphonic acid resin, in the presence of formaldehyde or a suitable source of methylene or ethylene of formula I. R5 and R6 are independently selected from C1-C12 hydrocarbons or H; X is either O or S; n is an integer from, 1 to 100; and m is 1 or 2: The compound of formula I may be suitable source of formaldehyde.
    Type: Application
    Filed: December 11, 2009
    Publication date: November 17, 2011
    Applicant: LUCITE INTERNATIONAL UK LIMITED
    Inventors: David William Johnson, Trevor Huw Morris
  • Publication number: 20110230675
    Abstract: The present invention provides a method of recovering a (meth)acrylic acid ester, which comprises the steps of: (a) carrying out an esterification reaction between an alcohol and (meth)acrylic acid in the presence of a catalyst to obtain a (meth)acrylic acid ester, wherein a byproduct is generated together with the (meth)acrylic acid ester; and (b) subjecting the byproduct generated in step (a) to a reaction with a catalyst and water in a reactor, wherein the water is fed into the reactor in order that water content exceeds 0 wt % but is 10 wt % or less in the reactor based on the total weight of reactants comprising the byproduct, the catalyst and the water, and thereby separating the (meth)acrylic acid, the alcohol and the (meth)acrylic acid ester contained in the byproduct from the byproduct to obtain the (meth)acrylic acid, the alcohol and the (meth)acrylic acid ester as a recovered product.
    Type: Application
    Filed: November 19, 2009
    Publication date: September 22, 2011
    Applicant: LG CHEM, LTD
    Inventors: Se-Won Baek, Hyun-kyu Kim, Jun-Seok Ko, Kyoung-Su Ha, Sung-Koo Park, Dong-Hyun Woo
  • Patent number: 7981255
    Abstract: There is provided a method for rectifying a vinyl compound liquor. The method includes the steps of a) providing a rectification column operated at a temperature and pressure and b) feeding the vinyl compound liquor to be rectified into the rectification column, wherein the pressure of the rectification column and the temperature of the fed vinyl compound liquor are controlled, such that the temperature of the fed vinyl compound liquor ranges from its bubble point at the pressure of the rectification column to 10° C. lower than the bubble point.
    Type: Grant
    Filed: September 26, 2007
    Date of Patent: July 19, 2011
    Assignee: Shanghai HuaYi Acrylic Acid Co., Ltd.
    Inventors: Jingming Shao, Jun Yin, Shuju Liu, Xiaodong Chu, Shengxian Xu
  • Publication number: 20110152568
    Abstract: A process for purifying allyl acetate is disclosed. An acetoxylation mixture is distilled at elevated pressure to remove propylene and generate a first bottoms mixture comprising allyl acetate, acetic acid, acrolein, allyl diacetate, and 3-acetoxypropionaldehyde. The first bottoms mixture is flash vaporized, and the resulting vapor is contacted with a solid acidic catalyst under conditions effective to decompose allyl diacetate and 3-acetoxypropionaldehyde. The flashed product, which comprises allyl acetate, acetic acid, and acrolein, is then distilled to remove acrolein and generate a second bottoms mixture comprising allyl acetate and acetic acid. The second bottoms mixture can be used to manufacture allyl alcohol.
    Type: Application
    Filed: December 17, 2009
    Publication date: June 23, 2011
    Inventors: Stephen H. Harris, Shaw-Chan Lin
  • Patent number: 7892403
    Abstract: A condenser includes: a top face of a tube plate on which acrylic acid may be condensed inside the condenser; a spray for spreading a polymerization inhibitor on the tube plate; a first polymerization inhibitor supply tube for supplying the polymerization inhibitor to the spray; and a supporter for supporting the spray at a predetermined position. The supporter supports the first polymerization inhibitor supply tube outside the condenser. The condenser allows a stable continuous operation for a long period of time by preventing polymerization of an easily polymerizable compound in the condenser into which a vapor of an easily polymerizable compound is supplied with a simple structure thereof.
    Type: Grant
    Filed: September 7, 2004
    Date of Patent: February 22, 2011
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Shuhei Yada, Yasushi Ogawa, Yoshiro Suzuki, Kimikatsu Jinno
  • Publication number: 20100317887
    Abstract: Process for preparing (meth)acrylates of C10-alcohol mixtures, by reacting (meth)acrylic acid with an isomer mixture of C10-alcohols composed of 2-propylheptanol as the main isomer and at least one of the C10-alcohols 2-propyl-4-methylhexanol, 2-propyl-5-methylhexanol, 2-isopropylheptanol, 2-isopropyl-4-methylhexanol, 2-isopropyl-5-methylhexanol and/or 2-propyl-4,4-dimethylpentanol, in the presence of at least one acidic catalyst and of at least one polymerization inhibitor and in the presence of a solvent which forms an azeotrope with water, the azeotrope is distilled off and condensed, and the condensate splits into an aqueous phase and an organic phase, wherein a) the esterification is performed in a reactor with a circulation evaporator and b) in the presence of a solvent, and c) the crude product is purified by subsequent purifying distillation.
    Type: Application
    Filed: February 26, 2009
    Publication date: December 16, 2010
    Applicant: BASF SE
    Inventors: Uwe Meisenburg, Frank Hoefer, Reinhold Schwalm, Nick Gruber, Lothar Karrer
  • Publication number: 20100261919
    Abstract: A process for purifying a lipid composition having predominantly neutral lipid components having at least one long chain polyunsaturated fatty acid is disclosed. The process employs contacting the lipid composition with a polar solvent, such as acetone, wherein the solvent is selected such that contaminants are less soluble in the solvent than is the long chain polyunsaturated fatty acid. The process is typically conducted at cooler temperatures, including about 0° C. Upon precipitation of the contaminants from the lipid composition, a separation is conducted to remove the precipitated material from the lipid composition. The long chain polyunsaturated fatty acids can include ARA, DPA, EPA, and/or DHA. The process of the present invention effectively winterizes lipid compositions, thereby reducing the tendency of such compositions to become hazy.
    Type: Application
    Filed: April 9, 2010
    Publication date: October 14, 2010
    Applicant: Martek Biosciences Corporation
    Inventors: Daniel G. Dueppen, Samuel G. Zeller, Sandra I. Diltz, Robert H. Driver
  • Patent number: 7750179
    Abstract: The invention relates to a process for purifying (meth)acrylates.
    Type: Grant
    Filed: October 11, 2006
    Date of Patent: July 6, 2010
    Assignee: Evonik Roehm GmbH
    Inventors: Bardo Schmitt, Joachim Knebel, Guenther Graeff
  • Publication number: 20100004417
    Abstract: The invention relates in general terms to a process for preparing to a process for purifying an alkyl methacrylate, comprising the steps of: A. providing an alkyl methacrylate with an impurity: B. adsorbing at least some of the impurity onto a purifying solid to obtain an ultrapure alkyl methacrylate, to a process for preparing an ultrapure alkyl methacrylate, to an apparatus for preparing alkyl methacrylates, to a process for preparing a polymer based at least partly on alkyl methacrylates, to the use of an alkyl methacrylate obtained according to the invention in chemical products, and to chemical products comprising an alkyl methacrylate obtained according to the invention.
    Type: Application
    Filed: August 31, 2007
    Publication date: January 7, 2010
    Applicant: Evonik Roehm GmbH
    Inventors: Udo Gropp, Robert Weber, Thomas Schaefer, Andreas Perl, Rudolf Sing, Thomas Mertz
  • Publication number: 20090299090
    Abstract: The present invention relates to reducing corrosion of distillation equipment during azeotropic distillation of (meth)acrylic acid in the presence of dissolved copper, by providing aqueous (meth)acrylic acid having not more than 0.1% by weight formaldehyde, based on the total weight of the aqueous (meth)acrylic acid. The source of the copper may, for example, be copper-based polymerization inhibitors added to the aqueous (meth)acrylic acid and/or distillation equipment.
    Type: Application
    Filed: June 1, 2009
    Publication date: December 3, 2009
    Inventors: Keith F. Briegel, Michael Stanley DeCourcy, James Elder, James Jerrick Juilette, Joy Lydon Mendoza
  • Publication number: 20090209783
    Abstract: The present invention relates to a process for producing high purity hydroxyalkyl (meth)acrylates. Specifically, the present invention relates to an improved process which can commercially and advantageously yield high purity hydroxyalkyl (meth)acrylates from (meth)acrylic acid and alkylene oxides.
    Type: Application
    Filed: February 19, 2008
    Publication date: August 20, 2009
    Inventor: Michael A. Curtis
  • Patent number: 7569721
    Abstract: This invention relates to a process for conducting equilibrium-limited reactions, such as esterification and alcoholysis reactions, that uses two reaction zones. The first reaction zone operates under reaction conditions that retain at least a portion of the product in a liquid phase, and at least a portion of the liquid from the first reaction zone is introduced into a second reaction zone which operates under conditions sufficient to crack heavies, for example, Michael-addition heavies, formed in or introduced into said second reaction zone and to vaporize at least a portion of the product upon production thereof. Such a process allows for removal of product from the reaction system while catalyst desirably remains in the reaction system.
    Type: Grant
    Filed: February 19, 2004
    Date of Patent: August 4, 2009
    Assignee: Union Carbide Chemicals and Plastics Technology Corporation
    Inventors: Leah A. Patterson, Fungau Nmn Ho
  • Patent number: 7491841
    Abstract: A process for producing an acrylic ester using acrylic acid and an aliphatic or alicyclic alcohol having from 5 to 8 carbon atoms, as raw materials, and using a strongly acidic cation exchange resin as a catalyst. In such a process for producing an acrylic ester, a crude acrylic ester withdrawn from the bottom of a low-boiling separation column is supplied to a rectifying column, a rectified acrylic ester is taken out from the top of the rectifying column, while a high-boiling substance containing an acrylic ester, which is withdrawn from the bottom of the rectifying column, is supplied to a high-boiling separation column and/or a thin-film evaporator to separate it into an acrylic ester component and a high-boiling substance, and the separated acrylic ester component is taken out as a distillate and supplied to the low-boiling separation column for its recovery.
    Type: Grant
    Filed: July 6, 2007
    Date of Patent: February 17, 2009
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Hidefumi Haramaki, Manabu Matsui
  • Patent number: 7332092
    Abstract: E and Z isomers of alkene alcohols and/or alkene alcohol derivatives are separated by substantially continuously contacting an ion exchange medium which is ion exchanged with silver and/or copper ions with the feed stream comprising the E and Z isomers of at least one alkene alcohol and/or at least one alkene alcohol derivative, then removing a product stream having a higher concentration of the E or Z isomer of at least one alkene alcohol or derivative of the alkene alcohol relative to the concentration of the E or Z isomer of the alkene alcohol or derivative of the alkene alcohol in the feed stream.
    Type: Grant
    Filed: March 7, 2007
    Date of Patent: February 19, 2008
    Assignees: Calgon Carbon Corporation, InnovaAroma SA
    Inventors: Chen-Chou Chiang, Elad Shabtai
  • Patent number: 7319162
    Abstract: A method of decomposing a Michael addition reaction product formed as a by-product in the production step of a(meth)acrylic ester and recovering (meth)acrylic acid, a (meth)acrylic ester and an alcohol, in which the formation of an olefin as a by-product can be suppressed. A method of thermally decomposing a by-product at the time of production of a (meth)acrylic ester using an alcohol bearing a branched chain and having 3 or more carbon atoms, wherein the decomposition reaction is carried out in the absence of a catalyst.
    Type: Grant
    Filed: June 21, 2004
    Date of Patent: January 15, 2008
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Shuhei Yada, Kenji Takasaki, Yasushi Ogawa, Yoshiro Suzuki