Preparing Esters By Carbonylation Patents (Class 560/232)
  • Patent number: 9938226
    Abstract: Alkyl alkanoates, e.g., methyl propionate, are made by a gas phase process comprising the step of contacting under carbonylation conditions an alkene (e.g., ethylene), carbon monoxide, an alkanol (e.g., methanol), and a solid sulfide-based metal catalyst (e.g., iron sulfide). The alkyl alkanoate can be converted in a second step to an alkyl ester of an aliphatic carboxylic acid, e.g., methyl methacrylate, through condensation with an aldehyde, e.g., formaldehyde.
    Type: Grant
    Filed: September 11, 2014
    Date of Patent: April 10, 2018
    Assignee: Dow Global Technologies LLC
    Inventors: David G. Barton, Gerolamo Budroni, Steven L. F. Corthals
  • Patent number: 9873654
    Abstract: A mixture of polyfluoroalkene carboxylic acids or salts thereof represented by the general formulas: CnF2n+1CH?CF(CF2CF2)mCF2COOM and Cn?1F2n?1CF?CHCF2(CF2CF2)mCF2COOM wherein M is a hydrogen atom, an ammonium salt, an organic amine salt or an alkali metal, n is an integer of 1 to 6 and m is an integer of 0 to 2. The mixture of polyfluoroalkene carboxylic acids or salts thereof is produced by subjecting a polyfluoroalkane carboxylic acids represented by the general formula: CnF2n+1(CH2CF2)(CF2CF2)mCF2COOH to a dehydrofluorination reaction in the presence of a nitrogen-containing heterocyclic compound catalyst, and has a lower critical micelle concentration and less surface tension at that time, therefore, the mixture of polyfluoroalkene carboxylic acids or salts thereof can be effectively used as a surfactant in the polymerization of fluorine-containing monomers.
    Type: Grant
    Filed: July 28, 2015
    Date of Patent: January 23, 2018
    Assignee: Unimatec Co., Ltd.
    Inventors: Yuichiro Oda, Ryota Negishi
  • Patent number: 9809692
    Abstract: Provided is a plurality of resin beads, wherein the resin beads comprise polymerized units of monovinyl aromatic monomer and polymerized units of multivinyl aromatic monomer, and wherein the resin beads have BET surface area of 15 to 38 m2/g and volume capacity of 0.7 or higher. Also provided is a method of making a product of the chemical reaction of one or more reactants, where the method comprises reacting the reactants with each other in the presence of such resin beads.
    Type: Grant
    Filed: April 9, 2015
    Date of Patent: November 7, 2017
    Assignee: Rohm and Haas Company
    Inventors: Jose Antonio Trejo O'Reilly, Takashi Masudo, Daika Kouzaki
  • Patent number: 9809611
    Abstract: Novel bidentate ligands of general formula (I) are described. In formula (I), A and B each independently represent a linking group; and R represents a hydrocarbyl aromatic structure. The substituent(s) Yi on the aromatic structure together have a total number ?ti of atoms other than hydrogen such that ?ti is greater than or equal to 4, wherein ti represents the number of atoms other than hydrogen on a particular substituent Yi. i ranges from 1 to n; and n is the total number of substituent(s) Yi. The groups X1, X2, X3 and X4 are joined via tertiary carbon atoms to the respective atom Q2 or Q1. Q1 and Q2 each independently represent phosphorus, arsenic, or antimony. A catalyst system and a process for the carbonylation of ethylenically unsaturated compounds utilizing the catalyst system are also described.
    Type: Grant
    Filed: November 27, 2007
    Date of Patent: November 7, 2017
    Assignee: LUCITE INTERNATIONAL UK LIMITED
    Inventors: Graham Ronald Eastham, Ian Butler
  • Patent number: 9809528
    Abstract: The present disclosure is directed to methods and composition used in the preparation of alpha-hydroxy carboxylic acids and esters from higher sugars using a tandem catalyst system comprising retro-aldol catalysts and Lewis acid catalysts. In some embodiments, these alpha-hydroxy carboxylic acids may be prepared from pentoses and hexoses. The retro-aldol and Lewis catalysts may be characterized by their respective ability to catalyze a 1,2-carbon shift reaction and a 1,2-hydride shift reaction on an aldose or ketose substrate.
    Type: Grant
    Filed: July 12, 2016
    Date of Patent: November 7, 2017
    Assignee: California Institute of Technology
    Inventors: Marat Orazov, Mark E. Davis
  • Patent number: 9802185
    Abstract: The present invention provides a catalyst system capable of catalyzing the carbonylation of an ethylenically unsaturated compound, which system is obtainable by combining: a) a metal of Group VIB or Group VIIIB or a compound thereof, b) a bidentate phosphine, arsine or stibine ligand, and c) an acid, wherein the ligand is present in at least a 2:1 molar excess compared to the metal or the metal in the metal compound, and that the acid is present in at least a 2:1 molar excess compared to the ligand, a process for the carbonylation of an ethylenically unsaturated compound, a reaction medium, and use of the system.
    Type: Grant
    Filed: April 9, 2015
    Date of Patent: October 31, 2017
    Assignee: LUCITE INTERNATIONAL UK LIMITED
    Inventors: Graham Eastham, Neil Tindale
  • Patent number: 9776179
    Abstract: In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I with a metathesis reaction partner according to Formula IIb in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product according to Formula IIIb: and b) converting the metathesis product to the fatty olefin derivative. Each R1 is independently selected from H, C1-18 alkyl, and C2-18 alkenyl; R2b is C1-8 alkyl; subscript y is an integer ranging from 0 to 17; and subscript z is an integer ranging from 0 to 17. In certain embodiments, the metathesis catalyst is a tungsten catalyst or a molybdenum catalyst. In various embodiments, the fatty olefin derivative is a pheromone. Pheromone compositions and methods of using them are also described.
    Type: Grant
    Filed: November 17, 2016
    Date of Patent: October 3, 2017
    Assignee: PROVIVI, INC.
    Inventors: Keith M Wampler, Peter Meinhold, Pedro Coelho, Vu Bui, Levente Ondi, Hasan Mehdi
  • Patent number: 9776947
    Abstract: In a process for the production of dialkyl succinate from a feedstock comprising maleic anhydride, feed in the liquid phase is provided to a reactor operated at a temperature of at least about 150° C. The feed is contacted with hydrogen at a pressure of at least about 300 psig in the presence of an acid tolerant catalyst and an alkanol wherein at least some of the carbon carbon double bonds of the maleic anhydride are hydrogenated to form succinic acid and that the heat generated promotes esterification to dialkyl succinate in situ. A stream of dialkyl succinate is recovered from the reactor.
    Type: Grant
    Filed: October 13, 2014
    Date of Patent: October 3, 2017
    Assignee: JOHNSON MATTHEY DAVY TECHNOLOGIES LIMITED
    Inventors: Graham Reed, Andrew George Hiles, Rikard Umberto Andersson, Simon Nicholas Tilley, Paul Gordon
  • Patent number: 9771315
    Abstract: Provided is a method that can produce phenyl(meth)acrylate inexpensively and at high yields. The phenyl(meth)acrylate production method of the present invention reacts (meth)acrylic acid with carbonic acid diphenyl. Further, the phenyl(meth)acyrlate composition of the present invention contains 90-99.999 wt % phenyl(meth)acrylate and 0.001-10% carbonic acid diphenyl. Or, the phenyl(meth)acrylate composition of the present invention contains 90-99.999 wt % phenyl(meth)acrylate and 0.001-10 wt % of a specified compound.
    Type: Grant
    Filed: October 24, 2014
    Date of Patent: September 26, 2017
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Ryo Aizawa, Takeshi Matsuo, Naoshi Murata, Hiroyuki Mori
  • Patent number: 9771312
    Abstract: Process for the co-production of acetic acid and dimethyl ether with reduced formic acid content by distilling a mixture containing dimethyl ether, methanol and methyl formate, separating methyl formate from the mixture to recover dimethyl ether and methanol, and catalytically reacting the methanol and methyl acetate to produce a reaction product of acetic acid an dimethyl ether.
    Type: Grant
    Filed: June 12, 2015
    Date of Patent: September 26, 2017
    Assignee: BP CHEMICALS LIMITED
    Inventors: Mareike Beckers, Timothy Crispin Bristow
  • Patent number: 9738583
    Abstract: A process for preparing acrylic acid from formaldehyde and acetic acid, is performed by (i) providing a gaseous stream S1 comprising formaldehyde, acetic acid, oxygen and water, where the formaldehyde content of stream S1 is in the range from 8% to 18% by volume, based on the total volume of stream S1, the ratio of the volumes of acetic acid to formaldehyde is in the range from 0.6:1 to 1.1:1, and the molar ratio of oxygen to the total amount of organic carbon is in the range from 0.02:1 to 0.15:1; and (ii) contacting stream S1 with an aldol condensation catalyst in a reaction zone to obtain a gaseous stream S2 containing acrylic acid.
    Type: Grant
    Filed: November 10, 2016
    Date of Patent: August 22, 2017
    Assignee: BASF SE
    Inventors: Marco Hartmann, Lukas Schulz, Nicolai Tonio Woerz, Yong Liu, Till Christian Brueggemann, Michael Lejkowski, Johannes Lieberknecht
  • Patent number: 9732027
    Abstract: An object of the present invention is to provide a process for producing ?-fluoroacrylic acid esters at a high starting material conversion and a high yield. The present invention provides, as a means to achieve the object, a process for producing a compound represented by formula (1): wherein R1 and R2 are the same or different and each represent alkyl, fluoroalkyl, aryl optionally substituted with at least one substituent, halogen, or hydrogen; and R3 represents alkyl, fluoroalkyl, or aryl optionally substituted with at least one substituent, the process comprising step A of reacting a compound represented by formula (2): wherein the symbols are as defined above, with carbon monoxide and an alcohol represented by formula (3): R3—OH??(3) wherein the symbol is as defined above, in the presence of a transition metal complex catalyst containing at least one bidentate phosphine ligand and a base to thereby obtain the compound represented by formula (1).
    Type: Grant
    Filed: December 26, 2014
    Date of Patent: August 15, 2017
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Akihiro Gotou, Manaho Miyazaki, Sumi Ishihara, Takashi Namikawa, Tatsuya Ohtsuka, Yosuke Kishikawa
  • Patent number: 9701614
    Abstract: An object of the present invention is to provide a process for producing ?-fluoroacrylic acid esters at a high starting material conversion and a high yield. The present invention provides, as a means to achieve the object, a process for producing a compound represented by formula (1): wherein R1 and R2 are the same or different and each represent alkyl, fluoroalkyl, aryl optionally substituted with at least one substituent, halogen, or hydrogen; and R3 represents alkyl, fluoroalkyl, or aryl optionally substituted with at least one substituent, the process comprising step A of reacting a compound represented by formula (2): wherein the symbols are as defined above, with carbon monoxide and an alcohol represented by formula (3): R3—OH??(3) wherein the symbol is as defined above, in the presence of a transition metal complex catalyst containing at least one bidentate phosphine ligand and a base to thereby obtain the compound represented by formula (1).
    Type: Grant
    Filed: December 26, 2014
    Date of Patent: July 11, 2017
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Akihiro Gotou, Manaho Miyazaki, Sumi Ishihara, Takashi Namikawa, Tatsuya Ohtsuka, Yosuke Kishikawa
  • Patent number: 9695099
    Abstract: The present invention relates to a process for preparing acrylic acid from acetic acid and formaldehyde, which comprises (a) provision of a stream S1 comprising acetic acid and formaldehyde, where the molar ratio of acetic acid to formaldehyde in the stream S1 is in the range from 0.5:1 to 2:1; (b) contacting of the stream S1 with an aldol condensation catalyst comprising vanadium, phosphorus and oxygen to give a stream S2 comprising acrylic acid, where, in (b), the space velocity WHSV is in the range from 0.35 to 7.0 kg/kg/h.
    Type: Grant
    Filed: December 2, 2015
    Date of Patent: July 4, 2017
    Assignee: BASF SE
    Inventors: Yong Liu, Martin Dieterle, Nicolai Tonio Woerz, Andrei-Nicolae Parvulescu, Michael Lejkowski, Johannes Lieberknecht, Christian Walsdorff, Kazuhiko Amakawa
  • Patent number: 9695106
    Abstract: In an embodiment, a method of producing a carbonate comprises reacting carbon monoxide and chlorine in a phosgene reactor in the presence of a catalyst to produce a first product comprising phosgene; wherein carbon tetrachloride is present in the first product in an amount of 0 to 10 ppm by volume based on the total volume of phosgene; and reacting a monohydroxy compound with the phosgene to produce the carbonate; wherein the phosgene reactor comprises a tube, a shell, and a space located between the tube and the shell; wherein the tube comprises one or more of a mini-tube section and a second tube section; a first concentric tube concentrically located in the shell; a twisted tube; an internal scaffold; and an external scaffold.
    Type: Grant
    Filed: February 4, 2015
    Date of Patent: July 4, 2017
    Assignee: SABIC GLOBAL TECHNOLOGIES B.V.
    Inventors: Pankaj Singh Gautam, William E. Hollar, Jr., Sergio Ferrer Nadal, John Joseph Anderson
  • Patent number: 9656248
    Abstract: Provided is a catalyst having high activity and yield of a target product for producing an unsaturated aldehyde and/or an unsaturated carboxylic acid and further having high mechanical strength. The catalyst is a catalyst prepared by a method in which a catalyst formulation satisfies specified atomic ratios; and in the preparation thereof, a molybdenum component raw material is an ammonium molybdate, a solvent for dissolving the ammonium molybdate is water, a bismuth component raw material is bismuth nitrate, and a solvent for dissolving bismuth nitrate is a nitric acid aqueous solution, and the weight of water for dissolving the ammonium molybdate, the weight of the nitric acid aqueous solution for dissolving the bismuth nitrate, and the acid concentration of the nitric acid aqueous solution are satisfied with specified ranges, respectively.
    Type: Grant
    Filed: May 8, 2014
    Date of Patent: May 23, 2017
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Yuuta Nakazawa, Yoshiko Shoya, Masaki Nakahara, Eiji Nishimura, Kazuo Shiraishi, Tatsuhiko Kurakami, Ryota Hiraoka
  • Patent number: 9656950
    Abstract: Provided is a method for efficiently producing an oxime, which is a method for producing an oxime by oxidizing, an amine, the method comprising a first contact step and a second contact step, wherein the second contact step is performed by bringing an additional amine into contact with oxygen in the presence of at least a part of an oxidation product obtained in the first contact step.
    Type: Grant
    Filed: March 17, 2014
    Date of Patent: May 23, 2017
    Assignee: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Masahiro Hoshino, Yuta Kikuchi
  • Patent number: 9546120
    Abstract: Integrated process for the production of methyl acetate and methanol by carbonylating dimethyl ether with synthesis gas, recovering a methyl acetate stream and an unreached synthesis gas stream containing methyl acetate, and scrubbing the synthesis gas to remove methyl acetate. The scrubbed synthesis gas is passed for methanol synthesis.
    Type: Grant
    Filed: December 19, 2013
    Date of Patent: January 17, 2017
    Assignee: BP CHEMICALS LIMITED
    Inventor: Timothy Crispin Bristow
  • Patent number: 9512061
    Abstract: Process for the preparation of racemic ?-amino acids or of glycine, wherein the corresponding ?-hydroxycarboxylic acid, selected from hydroxyacetic acid, lactic acid, malic acid, ?-hydroxyglutamic acid, isocitric acid, tartronic acid and tartaric acid, or at least one salt of the corresponding ?-hydroxycarboxylic acid is reacted in the presence of at least one heterogeneous catalyst which comprises at least one transition metal, in the presence of hydrogen with at least one nitrogen compound (c), where the nitrogen compound (c) is selected from primary and secondary amines and ammonia.
    Type: Grant
    Filed: December 19, 2012
    Date of Patent: December 6, 2016
    Assignee: BASF SE
    Inventors: Roland Bou Chedid, Alfred Oftring, Wolfgang Staffel, Markus Christian Biel, Johann-Peter Melder, Christian Gruenanger
  • Patent number: 9505703
    Abstract: Process for the production of methyl acetate by carbonylating dimethyl ether with carbon monoxide in the presence of hydrogen and a zeolite catalyst. The process is carried out with a molar ratio of hydrogen to carbon monoxide of at least 1 and the catalyst has been calcined at a temperature of from about 375° C. to about 475° C.
    Type: Grant
    Filed: March 6, 2014
    Date of Patent: November 29, 2016
    Assignee: BP CHEMICALS LIMITED
    Inventors: Evert Jan Ditzel, Bogdan Costin Gagea, Nicholas John Hazel, John Glenn Sunley, Gordon John Haining
  • Patent number: 9505702
    Abstract: Integrated process for the production of methyl acetate and methanol. The process is carried out by carbonylating dimethyl ether with synthesis gas and recovering methanol and unreacted synthesis gas. The recovered synthesis gas is utilized as the sole fresh synthesis gas for methanol synthesis.
    Type: Grant
    Filed: December 19, 2013
    Date of Patent: November 29, 2016
    Assignee: BP CHEMICALS LIMITED
    Inventors: Edo Johann Becker, Timothy Crispin Bristow
  • Patent number: 9493608
    Abstract: This invention relates to a novel process for preparing an aliphatic hybrid ester/ether polyol. This process simultaneously transesterifies and alkoxylates a mixture of at least one ester group containing compound which is free of ether groups, and at least one or more hydroxyl group containing compound which is free of ester groups; with the proviso that the mixture has an overall hydroxyl number of less than or equal to 350; with at least one alkylene oxide; in the presence of a mixture of catalysts. The catalyst mixture comprises at least one DMC catalyst, and at least one non-alkaline transesterification catalyst.
    Type: Grant
    Filed: December 21, 2015
    Date of Patent: November 15, 2016
    Assignee: Covestro LLC
    Inventors: Kenneth G. McDaniel, Rick L. Adkins, Don S. Wardius
  • Patent number: 9492814
    Abstract: In accordance with the invention, there is provided a novel catalyst composition comprising MoVGaPdNbXY, wherein X comprises La, Te, Ge, Zn, In, or W; and Y comprises Al or Si; wherein Mo, V, Ga, Pd, Nb, La, Te, Ge, Zn, In, W, Al, or Si are optionally present in combination with oxygen; wherein the catalyst does not comprise an additional element that acts as a catalyst in the conversion of a propylene to the product. Also, disclosed is a method for the conversion of a propylene to a carboxylic acid moiety by contacting the propylene with the disclosed catalyst.
    Type: Grant
    Filed: April 7, 2014
    Date of Patent: November 15, 2016
    Assignee: SAUDI BASIC INDUSTRIES CORPORATION
    Inventors: Zaheer Irshad, Khalid Karim
  • Patent number: 9469591
    Abstract: Integrated process for the production of methyl acetate and methanol. The process is carried out by carbonylating dimethyl ether with synthesis gas, recovering methyl acetate and unreacted synthesis gas and supplying unreacted synthesis gas and fresh synthesis gas for methanol synthesis.
    Type: Grant
    Filed: December 19, 2013
    Date of Patent: October 18, 2016
    Assignee: BP CHEMICALS LIMITED
    Inventor: Timothy Crispin Bristow
  • Patent number: 9463444
    Abstract: The invention belongs to the technical field of preparing oxalate in coal to ethylene glycol, aiming at providing a preparation process for nanocatalysts with (111) crystal facet exposed and a process for vapor-phase CO oxidative coupling to oxalate. The nanocatalysts with (111) crystal facet exposed comprise carrier, active component and promoter on the carrier, wherein, in term of the weight of the carrier, the active component accounts for 0.05-2% of the weight of the carrier, the weight percentage of metal elements in the promoter is 20% or less. The nanocatalysts with (111) crystal facet exposed are prepared by the nanometals in situ supporting process. The preparation process is simple in procedure, has low energy consumption and can precisely control the size and exposed crystal facet of the active component nanoparticles. The obtained nanocatalysts with (111) crystal facet exposed are highly active for vapor-phase CO oxidative coupling to oxalate at a lower loading of noble metal.
    Type: Grant
    Filed: June 10, 2014
    Date of Patent: October 11, 2016
    Assignee: Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
    Inventors: Zhongning Xu, Guocong Guo, Mingsheng Wang, Yuangen Yao
  • Patent number: 9458078
    Abstract: A process for producing high purity acetic acid from a carbonylation reaction, wherein the carbonylation reaction is carried out while maintaining a low ethyl iodide content in the reaction medium. The ethyl iodide concentration may be maintained by removing acetaldehyde from the reaction medium and/or by adjusting at least one A) hydrogen partial pressure in the reactor, B) methyl acetate concentration of the reaction medium; and/or C) methyl iodide concentration of the reaction medium.
    Type: Grant
    Filed: October 2, 2015
    Date of Patent: October 4, 2016
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventors: Yaw-Hwa Liu, Mark O. Scates
  • Patent number: 9447012
    Abstract: A process for synthesizing adipic acid comprising the steps of using glucaric acid or galactaric acid as a starting material, using rhenium catalyst and acid catalyst, using one or more reaction solvents selected from a group consisting of heptanol and butanol; and b) subjecting glucaric acid ester or galactaric acid ester obtained from the step a) to hydrogenation reaction with precious metal catalyst, and then hydrolyzing the ester obtained from this reaction to obtain adipic acid.
    Type: Grant
    Filed: April 1, 2015
    Date of Patent: September 20, 2016
    Assignees: HYUNDAI MOTOR COMPANY, SNU R&DB FOUNDATION
    Inventors: Chae Hwan Hong, Young Gyu Kim, Nara Shin
  • Patent number: 9440226
    Abstract: The present invention provides a method for preparing methyl acetate, in which a feed gas containing an organic amine, dimethyl ether, carbon monoxide and optional hydrogen gas goes through a reactor loaded with a H-type mordenite catalyst, to produce methyl acetate; wherein said H-type mordenite catalyst is a H-type mordenite catalyst with adsorption of an organic amine. The method in the present invention improves the catalyst stability and prolongs the catalyst life, by using the H-type mordenite catalyst with adsorption of an organic amine as the catalyst and adding the organic amine in the feed gas to replenish the organic amine desorbed from the catalyst during the reaction.
    Type: Grant
    Filed: January 28, 2014
    Date of Patent: September 13, 2016
    Assignee: DALIAN INSTITUTE OF CHEMICAL PHYSICS, CHINESE ACADEMY OF SCIENCES
    Inventors: Youming Ni, Wenliang Zhu, Hongchao Liu, Yong Liu, Zhongmin Liu, Shuanghe Meng, Lina Li, Shiping Liu, Hui Zhou
  • Patent number: 9421522
    Abstract: A solid catalyst comprising an effective amount of iridium and at least one second metal selected from gallium, zinc, indium and germanium associated with a solid support material is useful for vapor phase carbonylation to produce carboxylic acids and esters from alkyl alcohols, esters, ethers or ester-alcohol mixtures. The iridium and at least one second metal are deposited on a support material. In some embodiments of the invention, the catalyst is useful for vapor phase carbonylation.
    Type: Grant
    Filed: December 17, 2012
    Date of Patent: August 23, 2016
    Assignee: Eastman Chemical Company
    Inventors: Zhidong George Zhu, Gerald Charles Tustin, Joseph Robert Zoeller, Mary Kathleen Moore, David Alan Jenkins
  • Patent number: 9404056
    Abstract: An apparatus for carrying out a carbon monoxide shift reaction, which includes converting carbon monoxide and water into carbon dioxide and hydrogen, the converting proceeding in a liquid phase with removal of a product gas including carbon dioxide and hydrogen, is provided. The apparatus includes dry methanol, as a first solvent in a first region for an absorption of carbon monoxide with simultaneous formation of methyl formate, and water, as a second solvent in a second region for a liberation of the product gas in order to avoid losses of hydrogen in a carbon dioxide region.
    Type: Grant
    Filed: July 24, 2013
    Date of Patent: August 2, 2016
    Assignee: SIEMENS AKTIENGESELLSCHAFT
    Inventors: Manfred Baldauf, Carsten Graeber, Marc Hanebuth, Gerhard Zimmermann
  • Patent number: 9340481
    Abstract: A process for producing acetic acid is disclosed, in which the methyl iodide concentration is maintained in the vapor product stream formed in a flashing step. The process includes introducing a lithium compound into the reactor and maintaining a concentration of lithium acetate in the reaction medium is in an amount from 0.3 to 0.7 wt. %. The reaction medium is fed forward to the flashing step. The methyl iodide concentration in the vapor product stream ranges from 24 to less than 36 wt. %, based on the weight of the vapor product stream. The vapor product stream is distilled in a first column to obtain an acetic acid product stream comprising acetic acid and hydrogen iodide in an amount of less than or equal to 300 wppm and/or methyl iodide in an amount from 0.1 to 6 wt. %.
    Type: Grant
    Filed: October 2, 2015
    Date of Patent: May 17, 2016
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventors: Ronald D. Shaver, Yaw-Hwa Liu, Mark O. Scates
  • Patent number: 9260369
    Abstract: A process for producing an acetic acid product having low butyl acetate content via a carbonylation reaction. The carbonylation reaction is carried out at a temperature from 100 to 300° C., a hydrogen partial pressure from 0.3 to 2 atm, and a metal catalyst concentration from 100 to 3000 wppm, based on the weight of the reaction medium. The butyl acetate concentration in the acetic acid product may be controlled by removing acetaldehyde from a stream derived from the reaction medium and/or by adjusting at least one of reaction temperature, hydrogen partial pressure, and metal catalyst concentration.
    Type: Grant
    Filed: April 23, 2015
    Date of Patent: February 16, 2016
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventors: Yaw-Hwa Liu, Mark O. Scates
  • Patent number: 9212117
    Abstract: Process for the production of acetic acid and dimethyl ether by contacting methanol and methyl acetate with a catalyst composition at a temperature in the range 140 to 250 ° C. The catalyst composition contains a zeolite having a 2-dimensional channel system comprising at least one channel which has a 10-membered ring.
    Type: Grant
    Filed: August 31, 2010
    Date of Patent: December 15, 2015
    Assignee: BP CHEMICALS LIMITED
    Inventors: Berian John Daniel, David John Law, John Glenn Sunley
  • Patent number: 9181168
    Abstract: Process for the production of methyl acetate and/or acetic acid by contacting a carbon monoxide-containing gas and methanol and/or reactive derivatives thereof with a mordenite loaded with copper and silver loaded by ion-exchange and subsequently regenerating the catalyst.
    Type: Grant
    Filed: January 24, 2012
    Date of Patent: November 10, 2015
    Assignee: BP CHEMICALS LIMITED
    Inventor: Evert Jan Ditzel
  • Publication number: 20150141693
    Abstract: Disclosed are methods for the continuous flow production of acrylic acid and derivatives thereof from an epoxide feedstock. In one embodiment, the method includes the steps of: contacting a process stream comprising ethylene oxide and an organic solvent with a carbonylation catalyst and carbon monoxide to provide a reaction stream containing beta propiolactone; applying the reaction stream containing the beta propiolactone to a nanofiltration membrane to produce a permeate stream containing beta lactone and a retentate stream containing carbonylation catalyst; and treating the permeate stream under conditions to convert the beta propiolactone into an acrylate ester. In some embodiments, the retentate stream is returned to the first step of the process where it is recharged with additional epoxide and passed through the sequence again.
    Type: Application
    Filed: July 2, 2013
    Publication date: May 21, 2015
    Inventors: Scott D. Allen, Geoffrey Coates
  • Patent number: 8957244
    Abstract: Process for preparing methyl formate by carbonylation of methanol by means of carbon monoxide in a carbonylation reactor in the presence of a catalyst system comprising alkali metal formate and alkali metal alkoxide to give a reaction mixture (RM) which comprises methyl formate, alkali metal formate, alkali metal alkoxide and possibly unreacted methanol and unreacted carbon monoxide and is taken from the carbonylation reactor, wherein the reaction mixture (RM) comprises at least 0.5% by weight of alkali metal alkoxide based on the total weight of the reaction mixture (RM) and the molar ratio of alkali metal formate to alkali metal alkoxide in the reaction mixture (RM) is greater than 1.
    Type: Grant
    Filed: November 25, 2013
    Date of Patent: February 17, 2015
    Assignee: BASF SE
    Inventors: Daniel Schneider, Klaus-Dieter Mohl, Martin Schäfer, Jürgen Paschold, Joaquim Henrique Teles, Stefan Rittinger
  • Patent number: 8956588
    Abstract: Method for the selective dealumination of the aluminum within the 12-membered ring channels of a zeolite of structure type MOR. The method includes the steps of (i) loading a MOR zeolite in the hydrogen or ammonium form with a univalent metal to obtain a metal loaded zeolite; and (ii) treating the metal loaded zeolite with steam at a temperature of at least 400° C. to obtain a metal loaded dealuminated zeolite.
    Type: Grant
    Filed: September 29, 2009
    Date of Patent: February 17, 2015
    Assignee: BP Chemicals Limited
    Inventors: Gareth Gerald Armitage, John Glenn Sunley
  • Patent number: 8927762
    Abstract: A method of producing at least one oxygenated compound, such as methyl acetate, dimethyl ether, and formaldehyde, by reacting dimethyl carbonate and carbon monoxide in the presence of a faujasite zeolite, zeolite Beta, Linde Type L (LTL) zeolite, or MCM-41 zeolite.
    Type: Grant
    Filed: November 6, 2012
    Date of Patent: January 6, 2015
    Assignee: Enerkem, Inc.
    Inventors: Stephane Marie-Rose, Esteban Chornet
  • Patent number: 8877961
    Abstract: C1-C6Alkyloxy- or benzyloxy-carbonyl esters of -{3-[(E)-(1-phenyl or naphthyl C1-C4alkyl)-imino]-propyl}-amino)-acetic acid, which are intermediates for producing known bridged monobactam compounds useful in the treatment of bacterial infections.
    Type: Grant
    Filed: April 26, 2013
    Date of Patent: November 4, 2014
    Assignee: Basilea Pharmaceutica AG
    Inventors: Marc Muller, Xiaoping Wu, Lin Xu
  • Patent number: 8809573
    Abstract: A process for the production of acetic acid and/or methyl acetate by the carbonylation of methanol, methyl acetate and/or dimethyl ether with carbon monoxide in the presence of a desilicated mordenite catalyst.
    Type: Grant
    Filed: May 6, 2010
    Date of Patent: August 19, 2014
    Assignee: BP Chemicals Limited
    Inventors: Gareth Gerald Armitage, Bogdan Costin Gagea, David John Law, John Glenn Sunley
  • Patent number: 8748672
    Abstract: By using an organic base when a carboxylic acid bromodifluoroethyl ester is sulfinated by using a sulfinating agent, there is obtained 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfinic acid ammonium salt. By oxidizing the 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfinic acid ammonium salt, there is obtained 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfonic acid ammonium salt. By using the 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfonic acid ammonium salt as a raw material and exchanging it into an onium salt directly or through saponification/esterification, there can be obtained a 2-alkylcarbonyloxy-1,1-difluoroethanesulfonic acid onium salt.
    Type: Grant
    Filed: July 5, 2013
    Date of Patent: June 10, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Yuji Hagiwara, Masashi Nagamori, Masaki Fujiwara, Jonathan Joachim Jodry, Satoru Narizuka
  • Publication number: 20140148614
    Abstract: Process for preparing methyl formate by carbonylation of methanol by means of carbon monoxide in a carbonylation reactor in the presence of a catalyst system comprising alkali metal formate and alkali metal alkoxide to give a reaction mixture (RM) which comprises methyl formate, alkali metal formate, alkali metal alkoxide and possibly unreacted methanol and unreacted carbon monoxide and is taken from the carbonylation reactor, wherein the reaction mixture (RM) comprises at least 0.5% by weight of alkali metal alkoxide based on the total weight of the reaction mixture (RM) and the molar ratio of alkali metal formate to alkali metal alkoxide in the reaction mixture (RM) is greater than 1.
    Type: Application
    Filed: November 25, 2013
    Publication date: May 29, 2014
    Applicant: BASF SE
    Inventors: Daniel Schneider, Klaus-Dieter Mohl, Martin Schäfer, Jürgen Paschold, Joaquim Henrique Teles, Stefan Rittinger
  • Publication number: 20140121404
    Abstract: A system and method for removing acetaldehyde from an acetic acid system, including providing a solution from the acetic acid system, the stream having methyl iodide and acetaldehyde, and contacting the solution with an ion-exchange resin and/or liquid catalyst.
    Type: Application
    Filed: October 31, 2012
    Publication date: May 1, 2014
    Applicant: Lyondell Chenmical Technology., L.P.
    Inventors: Noel C. Hallinan, Brian A. Salisbury
  • Patent number: 8710107
    Abstract: A method and apparatus for synthesizing ethanol using synthetic routes via synthesis gas are disclosed. A method and apparatus for gasifying biomass, such as biomass, in a steam gasifier that employs a fluidized bed and heating using hot flue gases from the combustion of synthesis gas is described. Methods and apparatus for converting synthesis gas into ethanol are also disclosed, using stepwise catalytic reactions to convert the carbon monoxide and hydrogen into ethanol using catalysts including iridium acetate.
    Type: Grant
    Filed: December 1, 2011
    Date of Patent: April 29, 2014
    Assignee: Woodland Biofuels Inc.
    Inventors: Larry Jack Melnichuk, Karen Venita Kelly, Robert S. Davis
  • Patent number: 8692015
    Abstract: Process for the production of at least one carbonylation product selected from acetic acid and methyl acetate, by carbonylating at least one carbonylatable reactant selected from methanol and reactive derivatives thereof with carbon monoxide in the presence of a catalyst. The catalyst is a mordenite which has been treated with an aqueous ammonium hydroxide solution and has a silica:alumina molar ratio of at least 10:1, and the reactive derivatives are selected from methyl acetate and dimethyl ether.
    Type: Grant
    Filed: May 6, 2010
    Date of Patent: April 8, 2014
    Assignee: BP Chemicals Limited
    Inventors: Evert Jan Ditzel, Bogdan Costin Gagea
  • Publication number: 20140094622
    Abstract: A method of producing methyl acetate from methanol in which methanol and carbon monoxide are reacted in a first reaction zone to provide a reaction product including methyl acetate, acetic acid, and unreacted methanol. The reaction product then is passed to a second reaction zone, wherein the acetic acid is reacted with the unreacted methanol to provide additional methyl acetate. The method is a more efficient method for producing methyl acetate from methanol in that acetic acid is not separated from the reaction product.
    Type: Application
    Filed: October 2, 2012
    Publication date: April 3, 2014
    Inventors: Stephane MARIE-ROSE, Esteban CHORNET
  • Patent number: 8624054
    Abstract: A process for the production of methyl acetate by reacting dimethyl ether with carbon monoxide into a carbonylation reactor containing a mordenite catalyst in the presence of added methyl acetate and/or acetic acid.
    Type: Grant
    Filed: November 19, 2009
    Date of Patent: January 7, 2014
    Assignee: BP Chemicals Limited
    Inventors: Nicholas John Hazel, Lesley Ann Key, Mark Stephen Roberts, John Glenn Sunley
  • Publication number: 20130310599
    Abstract: A process for the production of methyl acetate and/or acetic acid by contacting a carbon monoxide-containing gas and methanol and/or reactive derivatives thereof with a mordenite loaded with copper and silver loaded by ion-exchange and subsequently regenerating the catalyst.
    Type: Application
    Filed: January 24, 2012
    Publication date: November 21, 2013
    Applicant: BP Chemicals Limited
    Inventor: Evert Jan Ditzel
  • Patent number: 8581009
    Abstract: By using an organic base when a carboxylic acid bromodifluoroethyl ester is sulfinated by using a sulfinating agent, there is obtained 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfinic acid ammonium salt. By oxidizing the 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfinic acid ammonium salt, there is obtained 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfonic acid ammonium salt. By using the 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfonic acid ammonium salt as a raw material and exchanging it into an onium salt directly or through saponification/esterification, there can be obtained a 2-alkylcarbonyloxy-1,1-difluoroethanesulfonic acid onium salt.
    Type: Grant
    Filed: September 5, 2008
    Date of Patent: November 12, 2013
    Assignee: Central Glass Company, Limited
    Inventors: Yuji Hagiwara, Masashi Nagamori, Masaki Fujiwara, Jonathan Joachim Jodry, Satoru Narizuka
  • Patent number: 8552216
    Abstract: Process for the production of methyl acetate by carbonylating a dimethyl ether feed with carbon monoxide under substantially anhydrous conditions, in the presence of a zeolite catalyst effective for the carbonylation. The carbonylation is carried out at a temperature in the range of 275 to 350° C. and in the presence of hydrogen.
    Type: Grant
    Filed: April 23, 2008
    Date of Patent: October 8, 2013
    Assignee: BP Chemicals Limited
    Inventors: Jon Michael Stewart Deeley, Evert Jan Ditzel, David John Law, Mark Stephen Roberts, John Glenn Sunley