Purification Or Recovery Patents (Class 560/218)
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Patent number: 10723689Abstract: 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: GrantFiled: December 27, 2018Date of Patent: July 28, 2020Assignee: Mitsubishi Chemical CorporationInventor: Yasushi Ogawa
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Patent number: 10597350Abstract: 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: GrantFiled: May 15, 2017Date of Patent: March 24, 2020Assignee: Dow Global Technologies LLCInventor: William G. Worley
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Patent number: 10435335Abstract: 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: GrantFiled: September 25, 2017Date of Patent: October 8, 2019Inventor: Hiroki Emoto
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Patent number: 9796651Abstract: 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: GrantFiled: July 24, 2014Date of Patent: October 24, 2017Assignee: Arkema FranceInventors: Michel Fauconet, Roger L. Roundy, Stephane Denis, Samuel M. Daniel
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Patent number: 9403751Abstract: 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: GrantFiled: September 23, 2014Date of Patent: August 2, 2016Assignee: Arkema FranceInventors: Serge Tretjak, Stephane Denis
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Patent number: 9067880Abstract: 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: GrantFiled: October 13, 2011Date of Patent: June 30, 2015Inventors: Michael A. Curtis, David A. Flosser, Jamie J. Juliette, Philippe P. Maillot, Donna Williams
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Publication number: 20150087857Abstract: 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: ApplicationFiled: September 23, 2014Publication date: March 26, 2015Applicant: Arkema FranceInventors: Serge TRETJAK, Stephane DENIS
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Publication number: 20150045579Abstract: 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: ApplicationFiled: August 9, 2013Publication date: February 12, 2015Inventors: Shiguang LI, Shaojun ZHOU, Miao YU
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Publication number: 20150038736Abstract: 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: ApplicationFiled: February 5, 2013Publication date: February 5, 2015Applicant: Mitsubishi Rayon Co., Ltd.Inventors: Junichi Morioka, Shuhei Otsuka
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Patent number: 8940925Abstract: 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: GrantFiled: January 27, 2010Date of Patent: January 27, 2015Assignee: Arkema FranceInventors: Jean-Michel Paul, Coralie Graire, Audrey Riehl
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Patent number: 8907121Abstract: 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: GrantFiled: December 11, 2009Date of Patent: December 9, 2014Assignee: Lucite International UK LimitedInventors: David William Johnson, Trevor Huw Morris
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Patent number: 8859804Abstract: 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: GrantFiled: February 4, 2010Date of Patent: October 14, 2014Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Ryuichi Ansai, Hiroyuki Nogami, Kuniyoshi Ogura
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Patent number: 8846840Abstract: 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: GrantFiled: March 29, 2011Date of Patent: September 30, 2014Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Kikuo Furukawa, Toshiharu Yamashita, Yoshio Nishimura
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Publication number: 20140275614Abstract: 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: ApplicationFiled: March 14, 2014Publication date: September 18, 2014Applicant: Zwitter Technology, LLCInventors: Yuting Li, Hong Xue, Yingquan Song
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Publication number: 20140275613Abstract: 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: ApplicationFiled: September 12, 2013Publication date: September 18, 2014Applicant: Aurora Algae, Inc.Inventors: Jeffrey Gerard Hippler, Louis Anthony Kapicak, Kristen Potter
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Publication number: 20140243551Abstract: 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: ApplicationFiled: October 2, 2012Publication date: August 28, 2014Inventors: Maria Luz Bellido Cabello De Alba, Giovanni Appendino, Alberto Pagani, Eduardo Munoz Blanco
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Patent number: 8802889Abstract: 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: GrantFiled: September 20, 2011Date of Patent: August 12, 2014Assignee: Showa Denko K.K.Inventor: Wataru Oguchi
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Patent number: 8772534Abstract: 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: GrantFiled: November 19, 2009Date of Patent: July 8, 2014Assignee: LG Chem, Ltd.Inventors: Se-Won Baek, Hyun-Kyu Kim, Jun-Seok Ko, Kyoung-Su Ha, Sung-Koo Park, Dong-Hyun Woo
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Publication number: 20140135523Abstract: 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: ApplicationFiled: September 27, 2013Publication date: May 15, 2014Applicant: BASF SEInventors: Ulrich JAEGER, Volker SCHLIEPHAKE, Ortmund LANG, Jochen PETZOLDT, Tobias Johannes KORN, Virginie BETTE, Claus HECHLER
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Publication number: 20140128465Abstract: 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: ApplicationFiled: January 13, 2014Publication date: May 8, 2014Inventors: Krishna Raman, Jung Lee, Neil Leininger, Chris Luigart
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Patent number: 8609886Abstract: 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: GrantFiled: January 8, 2010Date of Patent: December 17, 2013Assignee: Kuraray Co., Ltd.Inventors: Kei Miyoshi, Goro Asanuma
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Patent number: 8592624Abstract: 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: GrantFiled: May 15, 2009Date of Patent: November 26, 2013Assignee: Lucite International UK LimitedInventors: David William Johnson, Trevor Huw Morris
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Publication number: 20130217914Abstract: 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: ApplicationFiled: October 13, 2011Publication date: August 22, 2013Applicant: ROHM AND HAAS COMPANYInventors: Michael A. Curtis, David A. Flosser, Jamie J. Juliette, Philippe P. Maillot, Donna Williams
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Publication number: 20130158288Abstract: 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: ApplicationFiled: December 16, 2011Publication date: June 20, 2013Applicant: CELANESE INTERNATIONAL CORPORATIONInventors: Craig J. Peterson, R. Jay Warner, Josefina T. Chapman
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Patent number: 8455675Abstract: 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: GrantFiled: April 28, 2010Date of Patent: June 4, 2013Assignees: 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
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Patent number: 8394982Abstract: A process for purifying an unsaturated compound, where purification is performed in a plant with evaporators.Type: GrantFiled: August 29, 2008Date of Patent: March 12, 2013Assignee: Evonik Röhm GmbHInventors: Benedikt Laux, Christian Maul, Volker Schleep, Ingo Sander
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Publication number: 20130006012Abstract: 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: ApplicationFiled: December 22, 2011Publication date: January 3, 2013Inventors: Bruce E. Firth, Sharon E. Kirk
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Patent number: 8324424Abstract: 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: GrantFiled: August 31, 2007Date of Patent: December 4, 2012Assignee: Evonik Röhm GmbHInventors: Udo Gropp, Robert Weber, Thomas Schaefer, Andreas Perl, Rudolf Sing, Thomas Mertz
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Patent number: 8304573Abstract: 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: GrantFiled: March 7, 2008Date of Patent: November 6, 2012Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Akinobu Sasaki, Nobuyuki Kikuya, Takashi Ookubo, Masahiro Hayashida
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Patent number: 8198475Abstract: 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: GrantFiled: December 16, 2009Date of Patent: June 12, 2012Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Kikuo Furukawa, Yoshihisa Arai
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Patent number: 8183406Abstract: 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: GrantFiled: September 13, 2010Date of Patent: May 22, 2012Inventors: Andrew M. Lemonds, Jinsuo Xu
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Patent number: 8173832Abstract: 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: GrantFiled: March 28, 2007Date of Patent: May 8, 2012Assignee: Kuraray Co., Ltd.Inventors: Katsuji Ujita, Keisuke Saeki
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Patent number: 8157969Abstract: 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: GrantFiled: April 26, 2007Date of Patent: April 17, 2012Assignee: Rohm and Haas CompanyInventors: Barnett John O., Michael Stanley DeCourcy, Michael W. Hurley
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Publication number: 20120029229Abstract: 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: ApplicationFiled: January 8, 2010Publication date: February 2, 2012Applicant: KURARAY CO., LTD.Inventors: Kei Miyoshi, Goro Asanuma
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Publication number: 20110306783Abstract: 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: ApplicationFiled: February 25, 2010Publication date: December 15, 2011Applicant: Evonik Roehm GmbHInventors: Dirk Broell, Benedikt Laux, Christian Maul, Thorben Schuetz, Bardo Schmitt, Volker Schleep, Claus Zimmer
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Publication number: 20110282023Abstract: 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: ApplicationFiled: December 11, 2009Publication date: November 17, 2011Applicant: LUCITE INTERNATIONAL UK LIMITEDInventors: David William Johnson, Trevor Huw Morris
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Publication number: 20110230675Abstract: 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: ApplicationFiled: November 19, 2009Publication date: September 22, 2011Applicant: LG CHEM, LTDInventors: Se-Won Baek, Hyun-kyu Kim, Jun-Seok Ko, Kyoung-Su Ha, Sung-Koo Park, Dong-Hyun Woo
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Patent number: 7981255Abstract: 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: GrantFiled: September 26, 2007Date of Patent: July 19, 2011Assignee: Shanghai HuaYi Acrylic Acid Co., Ltd.Inventors: Jingming Shao, Jun Yin, Shuju Liu, Xiaodong Chu, Shengxian Xu
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Publication number: 20110152568Abstract: 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: ApplicationFiled: December 17, 2009Publication date: June 23, 2011Inventors: Stephen H. Harris, Shaw-Chan Lin
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Patent number: 7892403Abstract: 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: GrantFiled: September 7, 2004Date of Patent: February 22, 2011Assignee: Mitsubishi Chemical CorporationInventors: Shuhei Yada, Yasushi Ogawa, Yoshiro Suzuki, Kimikatsu Jinno
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Publication number: 20100317887Abstract: 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: ApplicationFiled: February 26, 2009Publication date: December 16, 2010Applicant: BASF SEInventors: Uwe Meisenburg, Frank Hoefer, Reinhold Schwalm, Nick Gruber, Lothar Karrer
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Publication number: 20100261919Abstract: 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: ApplicationFiled: April 9, 2010Publication date: October 14, 2010Applicant: Martek Biosciences CorporationInventors: Daniel G. Dueppen, Samuel G. Zeller, Sandra I. Diltz, Robert H. Driver
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Patent number: 7750179Abstract: The invention relates to a process for purifying (meth)acrylates.Type: GrantFiled: October 11, 2006Date of Patent: July 6, 2010Assignee: Evonik Roehm GmbHInventors: Bardo Schmitt, Joachim Knebel, Guenther Graeff
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Publication number: 20100004417Abstract: 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: ApplicationFiled: August 31, 2007Publication date: January 7, 2010Applicant: Evonik Roehm GmbHInventors: Udo Gropp, Robert Weber, Thomas Schaefer, Andreas Perl, Rudolf Sing, Thomas Mertz
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Publication number: 20090299090Abstract: 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: ApplicationFiled: June 1, 2009Publication date: December 3, 2009Inventors: Keith F. Briegel, Michael Stanley DeCourcy, James Elder, James Jerrick Juilette, Joy Lydon Mendoza
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Publication number: 20090209783Abstract: 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: ApplicationFiled: February 19, 2008Publication date: August 20, 2009Inventor: Michael A. Curtis
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Patent number: 7569721Abstract: 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: GrantFiled: February 19, 2004Date of Patent: August 4, 2009Assignee: Union Carbide Chemicals and Plastics Technology CorporationInventors: Leah A. Patterson, Fungau Nmn Ho
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Patent number: 7491841Abstract: 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: GrantFiled: July 6, 2007Date of Patent: February 17, 2009Assignee: Nippon Shokubai Co., Ltd.Inventors: Hidefumi Haramaki, Manabu Matsui
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Patent number: 7332092Abstract: 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: GrantFiled: March 7, 2007Date of Patent: February 19, 2008Assignees: Calgon Carbon Corporation, InnovaAroma SAInventors: Chen-Chou Chiang, Elad Shabtai
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Patent number: 7319162Abstract: 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: GrantFiled: June 21, 2004Date of Patent: January 15, 2008Assignee: Mitsubishi Chemical CorporationInventors: Shuhei Yada, Kenji Takasaki, Yasushi Ogawa, Yoshiro Suzuki