Preparing Esters By Carbonylation Patents (Class 560/232)
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Patent number: 9938226Abstract: 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: GrantFiled: September 11, 2014Date of Patent: April 10, 2018Assignee: Dow Global Technologies LLCInventors: David G. Barton, Gerolamo Budroni, Steven L. F. Corthals
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Patent number: 9873654Abstract: 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: GrantFiled: July 28, 2015Date of Patent: January 23, 2018Assignee: Unimatec Co., Ltd.Inventors: Yuichiro Oda, Ryota Negishi
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Patent number: 9809692Abstract: 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: GrantFiled: April 9, 2015Date of Patent: November 7, 2017Assignee: Rohm and Haas CompanyInventors: Jose Antonio Trejo O'Reilly, Takashi Masudo, Daika Kouzaki
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Patent number: 9809611Abstract: 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: GrantFiled: November 27, 2007Date of Patent: November 7, 2017Assignee: LUCITE INTERNATIONAL UK LIMITEDInventors: Graham Ronald Eastham, Ian Butler
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Patent number: 9809528Abstract: 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: GrantFiled: July 12, 2016Date of Patent: November 7, 2017Assignee: California Institute of TechnologyInventors: Marat Orazov, Mark E. Davis
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Patent number: 9802185Abstract: 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: GrantFiled: April 9, 2015Date of Patent: October 31, 2017Assignee: LUCITE INTERNATIONAL UK LIMITEDInventors: Graham Eastham, Neil Tindale
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Patent number: 9776179Abstract: 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: GrantFiled: November 17, 2016Date of Patent: October 3, 2017Assignee: PROVIVI, INC.Inventors: Keith M Wampler, Peter Meinhold, Pedro Coelho, Vu Bui, Levente Ondi, Hasan Mehdi
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Patent number: 9776947Abstract: 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: GrantFiled: October 13, 2014Date of Patent: October 3, 2017Assignee: JOHNSON MATTHEY DAVY TECHNOLOGIES LIMITEDInventors: Graham Reed, Andrew George Hiles, Rikard Umberto Andersson, Simon Nicholas Tilley, Paul Gordon
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Patent number: 9771315Abstract: 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: GrantFiled: October 24, 2014Date of Patent: September 26, 2017Assignee: Mitsubishi Chemical CorporationInventors: Ryo Aizawa, Takeshi Matsuo, Naoshi Murata, Hiroyuki Mori
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Patent number: 9771312Abstract: 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: GrantFiled: June 12, 2015Date of Patent: September 26, 2017Assignee: BP CHEMICALS LIMITEDInventors: Mareike Beckers, Timothy Crispin Bristow
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Patent number: 9738583Abstract: 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: GrantFiled: November 10, 2016Date of Patent: August 22, 2017Assignee: BASF SEInventors: Marco Hartmann, Lukas Schulz, Nicolai Tonio Woerz, Yong Liu, Till Christian Brueggemann, Michael Lejkowski, Johannes Lieberknecht
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Patent number: 9732027Abstract: 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: GrantFiled: December 26, 2014Date of Patent: August 15, 2017Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Akihiro Gotou, Manaho Miyazaki, Sumi Ishihara, Takashi Namikawa, Tatsuya Ohtsuka, Yosuke Kishikawa
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Patent number: 9701614Abstract: 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: GrantFiled: December 26, 2014Date of Patent: July 11, 2017Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Akihiro Gotou, Manaho Miyazaki, Sumi Ishihara, Takashi Namikawa, Tatsuya Ohtsuka, Yosuke Kishikawa
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Patent number: 9695099Abstract: 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: GrantFiled: December 2, 2015Date of Patent: July 4, 2017Assignee: BASF SEInventors: Yong Liu, Martin Dieterle, Nicolai Tonio Woerz, Andrei-Nicolae Parvulescu, Michael Lejkowski, Johannes Lieberknecht, Christian Walsdorff, Kazuhiko Amakawa
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Patent number: 9695106Abstract: 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: GrantFiled: February 4, 2015Date of Patent: July 4, 2017Assignee: SABIC GLOBAL TECHNOLOGIES B.V.Inventors: Pankaj Singh Gautam, William E. Hollar, Jr., Sergio Ferrer Nadal, John Joseph Anderson
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Patent number: 9656248Abstract: 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: GrantFiled: May 8, 2014Date of Patent: May 23, 2017Assignee: Nippon Kayaku Kabushiki KaishaInventors: Yuuta Nakazawa, Yoshiko Shoya, Masaki Nakahara, Eiji Nishimura, Kazuo Shiraishi, Tatsuhiko Kurakami, Ryota Hiraoka
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Patent number: 9656950Abstract: 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: GrantFiled: March 17, 2014Date of Patent: May 23, 2017Assignee: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Masahiro Hoshino, Yuta Kikuchi
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Patent number: 9546120Abstract: 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: GrantFiled: December 19, 2013Date of Patent: January 17, 2017Assignee: BP CHEMICALS LIMITEDInventor: Timothy Crispin Bristow
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Patent number: 9512061Abstract: 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: GrantFiled: December 19, 2012Date of Patent: December 6, 2016Assignee: BASF SEInventors: Roland Bou Chedid, Alfred Oftring, Wolfgang Staffel, Markus Christian Biel, Johann-Peter Melder, Christian Gruenanger
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Patent number: 9505703Abstract: 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: GrantFiled: March 6, 2014Date of Patent: November 29, 2016Assignee: BP CHEMICALS LIMITEDInventors: Evert Jan Ditzel, Bogdan Costin Gagea, Nicholas John Hazel, John Glenn Sunley, Gordon John Haining
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Patent number: 9505702Abstract: 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: GrantFiled: December 19, 2013Date of Patent: November 29, 2016Assignee: BP CHEMICALS LIMITEDInventors: Edo Johann Becker, Timothy Crispin Bristow
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Patent number: 9493608Abstract: 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: GrantFiled: December 21, 2015Date of Patent: November 15, 2016Assignee: Covestro LLCInventors: Kenneth G. McDaniel, Rick L. Adkins, Don S. Wardius
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Patent number: 9492814Abstract: 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: GrantFiled: April 7, 2014Date of Patent: November 15, 2016Assignee: SAUDI BASIC INDUSTRIES CORPORATIONInventors: Zaheer Irshad, Khalid Karim
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Patent number: 9469591Abstract: 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: GrantFiled: December 19, 2013Date of Patent: October 18, 2016Assignee: BP CHEMICALS LIMITEDInventor: Timothy Crispin Bristow
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Patent number: 9463444Abstract: 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: GrantFiled: June 10, 2014Date of Patent: October 11, 2016Assignee: Fujian Institute of Research on the Structure of Matter, Chinese Academy of SciencesInventors: Zhongning Xu, Guocong Guo, Mingsheng Wang, Yuangen Yao
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Patent number: 9458078Abstract: 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: GrantFiled: October 2, 2015Date of Patent: October 4, 2016Assignee: CELANESE INTERNATIONAL CORPORATIONInventors: Yaw-Hwa Liu, Mark O. Scates
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Patent number: 9447012Abstract: 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: GrantFiled: April 1, 2015Date of Patent: September 20, 2016Assignees: HYUNDAI MOTOR COMPANY, SNU R&DB FOUNDATIONInventors: Chae Hwan Hong, Young Gyu Kim, Nara Shin
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Patent number: 9440226Abstract: 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: GrantFiled: January 28, 2014Date of Patent: September 13, 2016Assignee: DALIAN INSTITUTE OF CHEMICAL PHYSICS, CHINESE ACADEMY OF SCIENCESInventors: Youming Ni, Wenliang Zhu, Hongchao Liu, Yong Liu, Zhongmin Liu, Shuanghe Meng, Lina Li, Shiping Liu, Hui Zhou
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Patent number: 9421522Abstract: 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: GrantFiled: December 17, 2012Date of Patent: August 23, 2016Assignee: Eastman Chemical CompanyInventors: Zhidong George Zhu, Gerald Charles Tustin, Joseph Robert Zoeller, Mary Kathleen Moore, David Alan Jenkins
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Patent number: 9404056Abstract: 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: GrantFiled: July 24, 2013Date of Patent: August 2, 2016Assignee: SIEMENS AKTIENGESELLSCHAFTInventors: Manfred Baldauf, Carsten Graeber, Marc Hanebuth, Gerhard Zimmermann
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Patent number: 9340481Abstract: 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: GrantFiled: October 2, 2015Date of Patent: May 17, 2016Assignee: CELANESE INTERNATIONAL CORPORATIONInventors: Ronald D. Shaver, Yaw-Hwa Liu, Mark O. Scates
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Patent number: 9260369Abstract: 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: GrantFiled: April 23, 2015Date of Patent: February 16, 2016Assignee: CELANESE INTERNATIONAL CORPORATIONInventors: Yaw-Hwa Liu, Mark O. Scates
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Patent number: 9212117Abstract: 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: GrantFiled: August 31, 2010Date of Patent: December 15, 2015Assignee: BP CHEMICALS LIMITEDInventors: Berian John Daniel, David John Law, John Glenn Sunley
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Patent number: 9181168Abstract: 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: GrantFiled: January 24, 2012Date of Patent: November 10, 2015Assignee: BP CHEMICALS LIMITEDInventor: Evert Jan Ditzel
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Publication number: 20150141693Abstract: 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: ApplicationFiled: July 2, 2013Publication date: May 21, 2015Inventors: Scott D. Allen, Geoffrey Coates
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Patent number: 8957244Abstract: 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: GrantFiled: November 25, 2013Date of Patent: February 17, 2015Assignee: BASF SEInventors: Daniel Schneider, Klaus-Dieter Mohl, Martin Schäfer, Jürgen Paschold, Joaquim Henrique Teles, Stefan Rittinger
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Patent number: 8956588Abstract: 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: GrantFiled: September 29, 2009Date of Patent: February 17, 2015Assignee: BP Chemicals LimitedInventors: Gareth Gerald Armitage, John Glenn Sunley
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Patent number: 8927762Abstract: 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: GrantFiled: November 6, 2012Date of Patent: January 6, 2015Assignee: Enerkem, Inc.Inventors: Stephane Marie-Rose, Esteban Chornet
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Patent number: 8877961Abstract: 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: GrantFiled: April 26, 2013Date of Patent: November 4, 2014Assignee: Basilea Pharmaceutica AGInventors: Marc Muller, Xiaoping Wu, Lin Xu
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Patent number: 8809573Abstract: 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: GrantFiled: May 6, 2010Date of Patent: August 19, 2014Assignee: BP Chemicals LimitedInventors: Gareth Gerald Armitage, Bogdan Costin Gagea, David John Law, John Glenn Sunley
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Patent number: 8748672Abstract: 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: GrantFiled: July 5, 2013Date of Patent: June 10, 2014Assignee: Central Glass Company, LimitedInventors: Yuji Hagiwara, Masashi Nagamori, Masaki Fujiwara, Jonathan Joachim Jodry, Satoru Narizuka
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Publication number: 20140148614Abstract: 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: ApplicationFiled: November 25, 2013Publication date: May 29, 2014Applicant: BASF SEInventors: Daniel Schneider, Klaus-Dieter Mohl, Martin Schäfer, Jürgen Paschold, Joaquim Henrique Teles, Stefan Rittinger
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Publication number: 20140121404Abstract: 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: ApplicationFiled: October 31, 2012Publication date: May 1, 2014Applicant: Lyondell Chenmical Technology., L.P.Inventors: Noel C. Hallinan, Brian A. Salisbury
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Patent number: 8710107Abstract: 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: GrantFiled: December 1, 2011Date of Patent: April 29, 2014Assignee: Woodland Biofuels Inc.Inventors: Larry Jack Melnichuk, Karen Venita Kelly, Robert S. Davis
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Patent number: 8692015Abstract: 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: GrantFiled: May 6, 2010Date of Patent: April 8, 2014Assignee: BP Chemicals LimitedInventors: Evert Jan Ditzel, Bogdan Costin Gagea
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Publication number: 20140094622Abstract: 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: ApplicationFiled: October 2, 2012Publication date: April 3, 2014Inventors: Stephane MARIE-ROSE, Esteban CHORNET
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Patent number: 8624054Abstract: 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: GrantFiled: November 19, 2009Date of Patent: January 7, 2014Assignee: BP Chemicals LimitedInventors: Nicholas John Hazel, Lesley Ann Key, Mark Stephen Roberts, John Glenn Sunley
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Publication number: 20130310599Abstract: 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: ApplicationFiled: January 24, 2012Publication date: November 21, 2013Applicant: BP Chemicals LimitedInventor: Evert Jan Ditzel
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Patent number: 8581009Abstract: 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: GrantFiled: September 5, 2008Date of Patent: November 12, 2013Assignee: Central Glass Company, LimitedInventors: Yuji Hagiwara, Masashi Nagamori, Masaki Fujiwara, Jonathan Joachim Jodry, Satoru Narizuka
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Patent number: 8552216Abstract: 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: GrantFiled: April 23, 2008Date of Patent: October 8, 2013Assignee: BP Chemicals LimitedInventors: Jon Michael Stewart Deeley, Evert Jan Ditzel, David John Law, Mark Stephen Roberts, John Glenn Sunley