Preparing Esters By Carbonylation Patents (Class 560/232)
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Publication number: 20130261328Abstract: Disclosed is a process for the production and purification of glycolic acid or glycolic acid derivatives by the carbonylation of formaldehyde in the presence of a homogeneous acid catalyst and a carboxylic acid. This invention discloses hydrocarboxylations and corresponding homogeneous acid catalyst and glycolic acid separations. The homogeneous acid catalyst is readily separated from the hydrocarboxylation reaction effluent and recycled and the carboxylic acid is readily removed from the glycolic acid and the carboxylic acid is recycled.Type: ApplicationFiled: March 27, 2012Publication date: October 3, 2013Applicant: EASTMAN CHEMICAL COMPANYInventors: Scott Donald Barnicki, Robert Thomas Hembre, Stephen Neal Falling, Andrew James Vetter
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Publication number: 20130261329Abstract: Disclosed is a process for the production and purification of glycolic acid or glycolic acid derivatives by the carbonylation of methylene dipropionate in the presence of a homogeneous acid catalyst and propionic acid. This invention discloses hydrocarboxylations and corresponding homogeneous acid catalyst and glycolic acid separations.Type: ApplicationFiled: March 27, 2012Publication date: October 3, 2013Applicant: EASTMAN CHEMICAL COMPANYInventors: Scott Donald Barnicki, Robert Thomas Hembre, Stephen Neal Falling
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Patent number: 8536369Abstract: Process for producing methyl acetate by carbonylating a dimethyl ether feed with carbon monoxide under substantially anhydrous conditions in the presence of a mordenite catalyst which has been ion-exchanged or otherwise loaded with at least one of silver and copper. The mordenite is also ion-exchanged or otherwise loaded with platinum in an amount in the range 0.05 to 10 mol % relative to aluminum.Type: GrantFiled: April 23, 2008Date of Patent: September 17, 2013Assignee: BP Chemicals LimitedInventors: Evert Jan Ditzel, Andre Harmen Sijpkes, John Glenn Sunley
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Publication number: 20130172601Abstract: 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: ApplicationFiled: December 17, 2012Publication date: July 4, 2013Applicant: Eastman Chemical CompanyInventor: Eastman Chemical Company
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Patent number: 8471058Abstract: Process for the carbonylation of a carbonylatable reactant selected from at least one of dimethyl ether and methanol, by carbonylating the carbonylatable reactant with carbon monoxide in the presence of a catalyst to produce a carbonylation product selected from at least one of methyl acetate and acetic acid. The catalyst is formed by compositing a mordenite loaded with at least one of silver and copper, with an inorganic oxide binder.Type: GrantFiled: November 16, 2009Date of Patent: June 25, 2013Assignee: BP Chemicals LimitedInventors: Evert Jan Ditzel, David John Law, John Glenn Sunley
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Publication number: 20130150618Abstract: A mixing apparatus 100 for mixing at least two fluids, the mixing apparatus 100 comprising a shaft 120 rotatable about its longitudinal axis 121, a first 122 and a second 124 radially extending impeller mounted on the shaft 120 and respectively axially spaced apart, characterised in that the first impeller 122 comprises a plurality of curved blades 125 operable to move said fluids in an axial direction towards the second impeller 124, and the second impeller 124 comprises a plurality of curved blades 125 operable to move said fluids in an axial direction towards the first impeller 122.Type: ApplicationFiled: February 8, 2013Publication date: June 13, 2013Applicant: Lucite International UK LimitedInventor: Lucite International UK Limited
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Patent number: 8450521Abstract: Process for preparing methyl acetate and/or acetic acid by contacting a carbonylatable reactant selected from dimethyl ether and methanol with carbon monoxide in the presence of a catalyst. The catalyst is a H-mordenite bound with a mesoporous binder selected from silicas, aluminas, silica-aluminas, magnesium silicates and magnesium aluminum silicates.Type: GrantFiled: October 8, 2009Date of Patent: May 28, 2013Assignee: BP Chemicals LimitedInventors: Evert Jan Ditzel, David John Law, John Glenn Sunley
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Publication number: 20130123533Abstract: 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: ApplicationFiled: November 6, 2012Publication date: May 16, 2013Inventors: Stephane MARIE-ROSE, Esteban CHORNET
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Patent number: 8431732Abstract: Process for the manufacture of methyl acetate by carbonylating a carbonylatable reactant selected from dimethyl ether and dimethyl carbonate containing less than 2.5 wt % water with carbon monoxide in the presence of a mordenite catalyst. The mordenite has been ion-exchanged with at least one Group IB metal, and the molar ratio of the Group IB metal to total aluminum present in the mordenite is in the range 5 to 50 mol %.Type: GrantFiled: December 16, 2008Date of Patent: April 30, 2013Assignee: BP Chemicals LimitedInventors: Gareth Gerald Armitage, Evert Jan Ditzel, David John Law, John Glenn Sunley
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Publication number: 20130102807Abstract: A process for preparing carboxylic acid derivatives of the formula H—(C?O)—R, R is OR1 or NR2R3, R1 is optionally substituted C1-C15-alkyl, C5-C10-cycloalkyl, C5-C10-heterocyclyl, C5-C10-aryl or C5-C10-heteroaryl, substituents are C1-C15-alkyl, C1-C6-alkoxy, C5-C10-cycloalkyl or C5-C10-aryl; R2 and R3 are independently hydrogen or optionally substituted C1-C15-alkyl, C5-C10 cycloalkyl, C5-C10-heterocyclyl, C5-C10-aryl or C5-C10-heteroaryl, substituents are selected from the group consisting of C1-C15-alkyl, C5-C10-cycloalkyl and C5-C10-aryl or R2 and R3 together with the nitrogen atom form a five- or six-membered ring which optionally comprises one or more heteroatoms selected from O, S and N and bearing the substituent R4, R4 is hydrogen or C1-C6-alkyl; by reacting a reaction mixture comprising carbon dioxide, hydrogen and an alcohol of the formula R1—OH or an amine of the formula NHR2R3 in the presence of a catalyst comprising gold at a pressure from 0.2 to 30 MPa and a temperature from 20 to 200° C.Type: ApplicationFiled: July 26, 2012Publication date: April 25, 2013Applicant: BASF SEInventors: Thomas Schaub, Rocco Paciello, Marek Pazicky, Giuseppe Fachinetti, Debora Preti
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Patent number: 8426633Abstract: Process for the manufacture of at least one of acetic acid and methyl acetate by carbonylating at least one carbonylatable reactant selected from methanol, dimethyl ether and dimethyl carbonate with carbon monoxide in the presence of a zeolite of structure type MOR. The zeolite has greater than 50% of its crystals in the size range to 3 microns.Type: GrantFiled: December 16, 2008Date of Patent: April 23, 2013Assignee: BP Chemicals LimitedInventors: Avelino Corma Canos, Gordon John Haining, David John Law
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Patent number: 8394983Abstract: Process for the production of methyl acetate by the carbonylation of 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 greater than 250° C. to 350° C. and at a pressure in the range of greater than 10 barg to 100 barg.Type: GrantFiled: April 23, 2008Date of Patent: March 12, 2013Assignee: BP Chemicals LimitedInventors: Evert Jan Ditzel, David John Law, Mark Stephen Roberts
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Patent number: 8283490Abstract: Process for the production of methyl acetate by carbonylating a dimethyl ether feed with carbon monoxide in the presence of hydrogen under substantially anhydrous conditions, at a temperature in the range of greater than 250° C. to 350° C. and in the presence of a zeolite catalyst effective for said carbonylation. The concentration of dimethyl ether is at least 1 mol % based on the total feed.Type: GrantFiled: April 23, 2008Date of Patent: October 9, 2012Assignee: BP Chemicals LimitedInventors: Evert Jan Ditzel, David John Law
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Patent number: 8158815Abstract: A process for the carbonylation of dimethyl ether, dimethyl carbonate and/or methanol with carbon monoxide and hydrogen in the presence of a mordenite catalyst to produce at least one of acetic acid and methyl acetate in which process the mordenite catalyst is regenerated in-situ by contacting the catalyst with a regenerating gas comprising a molecular oxygen-containing gas and an inert diluent at a total pressure in the range 1 to 100 bar and wherein the partial pressure of the molecular oxygen-containing gas is such that the temperature of the catalyst is maintained within the range 225 to 325° C.Type: GrantFiled: December 16, 2008Date of Patent: April 17, 2012Assignee: BP Chemicals LimitedInventors: Evert Jan Ditzel, David John Law, George Ernest Morris, Mark Stephen Roberts, Stephan Andreas Schunk, Martin Smit, John Glenn Sunley
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Publication number: 20120078005Abstract: 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: ApplicationFiled: May 6, 2010Publication date: March 29, 2012Applicant: BP CHEMICALS LIMITEDInventors: Gareth Gerald Armitage, Bogdan Costin Gagea, David John Law, John Glenn Sunley
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Publication number: 20120053360Abstract: A 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 which 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.Type: ApplicationFiled: May 6, 2010Publication date: March 1, 2012Inventors: Evert Jan Ditzel, Bogdan Costin` Gagea
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Patent number: 8110711Abstract: Disclosed is a process for producing 2-bromo-2,2-difluoroethanol, which comprises reducing a bromodifluoroacetic acid derivative represented by the formula [1] by using an ate hydride complex as a reducing agent. 2-Bromo-2,2-difluoroethanol thus produced can be used as the starting material to carry out the esterification step, the sulfination step and the oxidation step in this order, thereby producing a 2-alkylcarbonyloxy-1,1-difluoroethanesulfonic acid salt, wherein A represents a substituted or unsubstituted linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 15 carbon atoms, a heteroaryloxy group having 4 to 15 carbon atoms, or a halogen atom.Type: GrantFiled: September 5, 2008Date of Patent: February 7, 2012Assignee: Central Glass Company, LimitedInventors: Jonathan Joachim Jodry, Masashi Nagamori, Yuji Hagiwara, Masaki Fujiwara, Satoru Narizuka
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Patent number: 8088832Abstract: 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: April 5, 2007Date of Patent: January 3, 2012Assignee: Woodland Biofuels Inc.Inventors: Larry Jack Melnichuk, Karen Venita Kelly, Robert S. Davis
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Publication number: 20110319654Abstract: 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: ApplicationFiled: November 19, 2009Publication date: December 29, 2011Inventors: Nicholas John Hazel, Lesley Ann Key, Mark Stephen Roberts, John Glenn Sunley
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Publication number: 20110306785Abstract: Preparation of selectively dealuminated zeolites of structure type MOR by loading the zeolite with a univalent metal followed by treatment with steam. The dealuminated zeolites subsequently converted to the hydrogen form and/or loaded with metals are suitable for use as catalysts in carbonylation processes to produce acetic acid and/or methyl acetate.Type: ApplicationFiled: September 29, 2009Publication date: December 15, 2011Inventors: Gareth Gerald Armitage, John Glenn Sunley
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Publication number: 20110269988Abstract: The present invention relates to a separation process for removing acetone from a mixture comprising acetone, methyl acetate and methyl iodide, said process comprising the steps of: (a) introducing said stream comprising acetone, methyl acetate and methyl iodide into a first distillation zone; (b) introducing acetic acid into said first distillation zone, either by addition of acetic acid to said stream comprising acetone, methyl acetate and methyl iodide or by introduction of acetic acid directly to the first distillation zone at one or more points at or above the point of introduction of said stream comprising acetone, methyl acetate and methyl iodide into the first distillation zone in step (a), or a combination of both; (c) removing from the first distillation zone an overhead stream comprising methyl iodide and a bottoms stream comprising acetone, methyl acetate, acetic acid, and a reduced amount of methyl iodide; (d) introducing into a second distillation zone the bottoms stream from step (c); (e) removType: ApplicationFiled: December 23, 2009Publication date: November 3, 2011Inventors: Sean Anthony Hennigan, David Edward George Jeffers, Martin John Sellers, Stephen James Smith, Peter John Wilson
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Publication number: 20110218356Abstract: A process for the preparation of methyl acetate and/or acetic acid by carbonylating dimethyl ether and/or methanol with carbon monoxide in the presence of a catalyst, which catalyst is a H-mordenite bound with a mesoporous binder selected from silicas, aluminas, silica-aluminas, magnesium silicates and magnesium aluminum silicates.Type: ApplicationFiled: October 8, 2009Publication date: September 8, 2011Inventors: Evert Jan Ditzel, David John Law, John Glenn Sunley
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Publication number: 20110105782Abstract: A process is described for the preparation of carbamates of primary and/or secondary polyamines, which process comprises the steps of vaporising a primary and/or secondary polyamine and reacting said vaporised primary and/or secondary polyamine with gaseous carbon dioxide. In particular, the process relates to the production of the carbamates of hexamethylenediamine, 1,4-diaminocyclohexane and 3-aminomethyl-3,5,5-trimethylcyclohexylamine.Type: ApplicationFiled: April 18, 2005Publication date: May 5, 2011Inventor: Maurizio Masi
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Publication number: 20110015431Abstract: Disclosed is a process for producing 2-bromo-2,2-difluoroethanol, which comprises reducing a bromodifluoroacetic acid derivative represented by the formula [1] by using an ate hydride complex as a reducing agent. 2-Bromo-2,2-difluoroethanol thus produced can be used as the starting material to carry out the esterification step, the sulfination step and the oxidation step in this order, thereby producing a 2-alkylcarbonyloxy-1,1-difluoroethanesulfonic acid salt, wherein A represents a substituted or unsubstituted linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 15 carbon atoms, a heteroaryloxy group having 4 to 15 carbon atoms, or a halogen atom.Type: ApplicationFiled: September 5, 2008Publication date: January 20, 2011Applicant: CENTRAL GLASS COMPANY, LIMITEDInventors: Jonathan Joachim Jodry, Masashi Nagamori, Yuji Hagiwara, Masaki Fujiwara, Satoru Narizuka
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Publication number: 20100317888Abstract: A process for the carbonylation of dimethyl ether, dimethyl carbonate and/or methanol with carbon monoxide and hydrogen in the presence of a mordenite catalyst to produce at least one of acetic acid and methyl acetate in which process the mordenite catalyst is regenerated in-situ by contacting the catalyst with a regenerating gas comprising a molecular oxygen-containing gas and an inert diluent at a total pressure in the range 1 to 100 bar and wherein the partial pressure of the molecular oxygen-containing gas is such that the temperature of the catalyst is maintained within the range 225 to 325° C.Type: ApplicationFiled: December 16, 2008Publication date: December 16, 2010Applicant: BP Chemicals LimitedInventors: Evert Jan Ditzel, David John Law, George Ernest Morris, Mark Stephen Roberts, Stephan Andreas Schunk, Martin Smit, John Glenn Sunley
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Patent number: 7842833Abstract: A carbonylation process for the production of a carbonylation product such as a carboxylic acid and a carboxylic acid ester by contacting carbon monoxide with a feed comprising an alcohol such as methanol and/or a reactive derivative thereof such as methyl acetate in the vapor phase using a heterogeneous heteropolyacid catalyst which has been ion-exchanged or loaded with at least one metal selected from rhodium, iridium, copper and palladium and a Group IA metal selected from lithium, sodium, potassium and rubidium.Type: GrantFiled: November 17, 2005Date of Patent: November 30, 2010Assignee: BP Chemicals LimitedInventor: Brian Ellis
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Publication number: 20100274045Abstract: A process for the manufacture of methyl acetate by the carbonylation of dimethyl ether or dimethyl carbonate with carbon monoxide under substantially anhydrous conditions in the presence of a Group TB metal loaded mordenite catalyst prepared by ion-exchanging mordenite with at least one Group IB metal, the ion-exchanged mordenite having a molar ratio of the Group IB metal to total aluminium present in the mordenite in the range 5 to 50 mol %.Type: ApplicationFiled: December 16, 2008Publication date: October 28, 2010Applicant: BP CHEMICALS LIMITEDInventors: Gareth Gerald Armitage, Evert Jan Ditzel, David John Law, John Glenn Sunley
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Publication number: 20100267985Abstract: A process for the manufacture of at least one of acetic acid and methyl acetate by the carbonylation of methanol, dimethyl ether and/or dimethyl carbonate with carbon monoxide in the presence of a zeolite catalyst of structure type MOR having a crystal size of no greater than about 3 microns.Type: ApplicationFiled: December 16, 2008Publication date: October 21, 2010Inventors: Avelino Corma Canos, Gordon John Haining, David John Law
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Patent number: 7772422Abstract: The present invention is directed to using methyl acetate from a vinyl acetate-based or a vinyl-or ethylene-alcohol based polymer or copolymer process directly for use in a methanol carbonylation production process to produce acetic acid, acetic anhydride, or a coproduction of each. Methyl acetate is a by-product of commercial polyvinyl-alcohol or alkene vinyl alcohol copolymer-based processes. Generally, this material is processed to recover methanol and acetic acid. Discussed herein is a cost-saving scheme to by-pass the methyl acetate processing at production or plant facilities and utilize the methyl acetate in an integrated methanol carbonylation unit. The scheme discussed eliminates an expensive hydrolysis step often associated with the polymer process.Type: GrantFiled: August 23, 2006Date of Patent: August 10, 2010Assignee: Celanese International CorporationInventors: Mark O. Scates, Stephen Charles Webb
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Patent number: 7772423Abstract: A process for the production of lower alkyl alkoxyacetates, preferably methyl methoxyacetate, by reaction of a di-(lower alkoxy)methane, preferably dimethoxymethane, with the acid form of a medium-pore or large-pore zeolite catalyst, preferably the acid form of faujasite, ZSM-5, mordenite, or beta, in the gas phase at atmospheric or near-atmospheric pressures.Type: GrantFiled: October 23, 2008Date of Patent: August 10, 2010Assignee: The Regents of the University of CaliforniaInventors: Fuat E. Celik, Tae-Jin Kim, Alexis T. Bell
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Patent number: 7741512Abstract: Process for preparing an aliphatic carboxylic acid having (n+1) carbon atoms, where n is an integer up to 6, and/or the ester derivative thereof by contacting an aliphatic alcohol having n carbon atoms and/or a reactive derivative thereof selected from dialkyl ether, ester of the alcohol and an alkyl halide with carbon monoxide in the presence of a catalyst. The catalyst consists of mordenite which has been ion- exchanged or otherwise loaded with silver.Type: GrantFiled: March 27, 2007Date of Patent: June 22, 2010Assignee: BP Chemicals LimitedInventors: Harry Kaiser, David John Law, Stephan Andreas Schunk, John Glenn Sunley
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Publication number: 20100130771Abstract: Production of methyl acetate by carbonylating a dimethyl ether feed with carbon monoxide under substantially anhydrous conditions, in the presence of a zeolite catalyst at a temperature in the range of greater than 250° C. to 350° C. and at a pressure in the range greater than 10 barg to 100 barg.Type: ApplicationFiled: April 23, 2008Publication date: May 27, 2010Applicant: BP Chemicals LimitedInventors: Evert Jan Ditzel, David John Law, Mark Stephen Roberts
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Publication number: 20100121099Abstract: Production of methyl acetate by carbonylating a dimethyl ether feed with carbon monoxide under substantially anhydrous conditions, in the presence of a zeolite catalyst at a temperature in the range 240° C. to 350° C. and in the presence of hydrogen.Type: ApplicationFiled: April 23, 2008Publication date: May 13, 2010Inventors: Jon Michael Stewart Deeley, Evert Jan Ditzel, David John Law, Mark Stephen Roberts, John Glenn Sunley
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Publication number: 20100121098Abstract: Production of methyl acetate by carbonylating a dimethyl ether feed with carbon monoxide under substantially anhydrous conditions, in the presence of a mordenite catalyst which contains copper and/or silver and 0.05 to 10 mol % platinum relative to aluminium.Type: ApplicationFiled: April 23, 2008Publication date: May 13, 2010Applicant: BP CHEMICALS LIMITEDInventors: Evert Jan Ditzel, Andre Harmen Sijpkes, John Glenn Sunley
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Publication number: 20100105947Abstract: A process for the production of lower alkyl alkoxyacetates, preferably methyl methoxyacetate, by reaction of a di-(lower alkoxy)methane, preferably dimethoxymethane, with the acid form of a medium-pore or large-pore zeolite catalyst, preferably the acid form of faujasite, ZSM-5, mordenite, or beta, in the gas phase at atmospheric or near-atmospheric pressures.Type: ApplicationFiled: October 23, 2008Publication date: April 29, 2010Inventors: Fuat E. Celik, Tae-Jin Kim, Alexis T. Bell
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Publication number: 20100063315Abstract: Production of methyl acetate by carbonylating a dimethyl ether feed with carbon monoxide in the presence of hydrogen under substantially anhydrous conditions, in the presence of a zeolite catalyst at a temperature in the range of greater than 250° C. to 350° C. and a dimethyl ether concentration of at least 1 mol %.Type: ApplicationFiled: April 23, 2008Publication date: March 11, 2010Inventors: Evert Jan Ditzel, David John Law
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Patent number: 7671233Abstract: A process for preparing a carboxylic acid by the carbonylation of an alcohol in a reaction medium is provided. The reaction medium includes a catalyst promoter having a metal species selected form the group consisting of group IIIA-IVA metals, group IB-VIIIB metals and lanthanides, together with a hydrohalic acid to prevent catalyst precipitation and to maintain high reaction rates in case of low water content.Type: GrantFiled: September 20, 2007Date of Patent: March 2, 2010Assignee: China Petrochemical Development CorporationInventors: Chi-He Chen, Chin-Yi Lee, Chia-Jung Tsai
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Patent number: 7642372Abstract: Preparation of an aliphatic carboxylic acid having (n+1) carbon atoms, where n is an integer up to 6, and/or an ester or anhydride thereof may be achieved by contacting an aliphatic alcohol having n carbon atoms and/or a reactive derivative thereof with carbon monoxide substantially in the absence of the halogens or derivatives thereof at a temperature in the range 250-600° C. and at a pressure in the range 10 to 200 bars, in the presence of a catalyst consisting essentially of a mordenite which has, as framework elements, silicon, aluminum and one or more of gallium, boron and iron, and which has been ion-exchanged or otherwise loaded with copper, nickel, iridium, rhodium or cobalt.Type: GrantFiled: March 24, 2005Date of Patent: January 5, 2010Assignee: BP Chemicals LimitedInventor: Warren John Smith
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Publication number: 20090275774Abstract: Preparation Of C1-C6 aliphatic carboxylic acids and/or esters or anhydrides thereof by reacting an alcohol and/or reactive derivative thereof with carbon monoxide under hydrous conditions in the presence of a ferrierite catalyst.Type: ApplicationFiled: March 27, 2007Publication date: November 5, 2009Inventor: David John Law
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Publication number: 20090247783Abstract: Disclosed is an improved carbonylation process for the production of carboxylic acids, carboxylic acid esters, and/or carboxylic acid anhydrides wherein a carbonylation feedstock compound selected from one or more organic oxygenates such as alcohols, ethers, and esters is contacted with carbon monoxide in the presence of a carbonylation catalyst and one or more onium compounds. The carbonylation process differs from known carbonylation processes in that a halide compound, other than the onium salt, such as a hydrogen halide (typically, hydrogen iodide) and/or an alkyl halide (typically, methyl iodide), extraneous or exogenous to the carbonylation process is not fed or supplied to the process. The process can be improved by using a bidentate ligand comprising two functional groups selected from tertiary amines and tertiary phosphines, such as 2,2?-bipyridine and diphosphine derivatives.Type: ApplicationFiled: April 1, 2008Publication date: October 1, 2009Applicant: EASTMAN CHEMICAL COMPANYInventors: Joseph Robert Zoeller, Mary Kathleen Moore
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Patent number: 7582792Abstract: Disclosed is a carbonylation process for the production of carboxylic acids, carboxylic acid esters and/or carboxylic acid anhydrides wherein a carbonylation feedstock compound selected from one or more organic oxygenates such as alcohols, ethers, and esters is contacted with carbon monoxide in the presence of a carbonylation catalyst and one or more onium compounds. The carbonylation process differs from known carbonylation processes in that a halide compound such as a hydrogen halide, typically hydrogen iodide, and/or alkyl halide, typically methyl iodide, extraneous or exogenous to the carbonylation process is not fed or supplied separately to the process.Type: GrantFiled: June 15, 2006Date of Patent: September 1, 2009Assignee: Eastman Chemical CompanyInventors: Joseph Robert Zoeller, Mary Kathleen Moore, Andrew James Vetter
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Patent number: 7566801Abstract: A polyfluoroalkyl alcohol, or a (meth)acrylic acid derivative thereof, represented by the following general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cOR (R:H or (meth)acrylic acid group; n: 1-6; a: 1-4; b: 1-3; and c: 1-3). Polyfluoroalkyl alcohol (R: hydrogen atom) can be produced by reaction of fluoroalkyl iodide represented by the following general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cI with N-methyl formamide, followed by hydrolysis in the presence of an acid catalyst, whereas polyfluoroalkyl alcohol (meth)acrylic acid derivative (R: (meth)acrylic acid group) can be produced by reaction of the polyfluoroalkyl alcohol with (meth)acrylic acid.Type: GrantFiled: March 9, 2007Date of Patent: July 28, 2009Assignee: Unimatec Co., LtdInventors: Seiichiro Murata, Masayosi Horiuti, Katsuyuki Sato, Hideki Abe, Haruyoshi Tatsu
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Publication number: 20090134546Abstract: The invention relates to the use of isobutene-containing olefin feedstock in oligomerization reactions, particularly in the production of octenes as feedstock for the manufacture of plasticizer alcohols, the process comprising contacting a feed comprising isobutene with a molecular sieve at a temperature in excess of 240° C. to produce a product low in triple-branched octenes.Type: ApplicationFiled: January 28, 2009Publication date: May 28, 2009Inventors: Stephen Harold Brown, Georges Marie Mathys
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Publication number: 20090105500Abstract: A carbonylation process for the production of a carbonylation product such as a carboxylic acid and a carboxylic acid ester by contacting carbon monoxide with a feed comprising an alcohol such as methanol and/or a reactive derivative thereof such as methyl acetate in the vapour phase using a heterogeneous heteropolyacid catalyst which has been ion-exchanged or loaded with at least one metal selected from rhodium, iridium, copper and palladium and a Group IA metal selected from lithium, sodium, potassium and rubidium.Type: ApplicationFiled: November 17, 2005Publication date: April 23, 2009Inventor: Brian Ellis
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Patent number: 7507855Abstract: A product comprising a C1-C3 aliphatic carboxylic acid or corresponding ester is produced by a process comprising carbonylating a C1-C3 aliphatic alcohol or a corresponding ester with carbon monoxide in the presence of a.zeolite catalyst having an 8-member ring channel which is interconnected with a channel defined by a ring with greater than or equal to 8 members, the 8-member ring having a window size of at least 2.5 Angstroms×at least 3.6 Angstroms and at least one Brønsted acid site and the zeolite having a silica:X2O3 ratio of at least 5, wherein X is selected from aluminium, boron, iron, gallium and mixtures thereof with the proviso that the zeolite is not mordenite or ferrierite.Type: GrantFiled: December 15, 2006Date of Patent: March 24, 2009Assignees: The Regents of the University of California, BP Chemicals Ltd.Inventors: Enrique Iglesia, John Glenn Sunley, David John Law, Aditya Bhan
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Patent number: 7491842Abstract: A carbonylation process for producing a carbonylation product by contacting carbon monoxide with a feed comprising an alcohol and/or a reactive derivative thereof in the vapour phase using an heterogeneous heteropolyacid catalyst comprising one or more metal cations selected from Cu, Fe, Ru, Os, Co, Rh, Ir, Ni, Pd and Pt and wherein there is at least 0.5 wt % water present in the feed.Type: GrantFiled: February 9, 2005Date of Patent: February 17, 2009Assignee: BP Chemicals LimitedInventor: Warren John Smith
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Publication number: 20090005588Abstract: Methods and systems for the production of ethyl acetate are described herein. The methods and systems incorporate the novel use of a high shear device to promote dispersion and mixing of a carbonyl co-reactant (e.g. acetic acid, acetaldehyde) with ethanol. The high shear device may allow for lower reaction temperatures and pressures and may also reduce reaction time with existing catalysts.Type: ApplicationFiled: June 19, 2008Publication date: January 1, 2009Applicant: H R D CORPORATIONInventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Patent number: 7465822Abstract: A product comprising a lower alkyl ester of a lower aliphatic carboxylic acid is produced by a process comprising reacting under substantially anhydrous conditions a lower alkyl ether with carbon monoxide in the presence of a zeolite catalyst having an 8-member ring channel which is interconnected with a channel defined by a ring with greater than or equal to 8 members, the 8-member ring having a window size of at least 2.5 Angstroms×at least 3.6 Angstroms and at least one Brønsted acid site and the zeolite having a silica:X2O3 ratio of at least 5, wherein X is selected from aluminum, boron, iron, gallium and mixtures thereof.Type: GrantFiled: December 15, 2006Date of Patent: December 16, 2008Assignees: BP Chemicals Ltd., The Regents of the University of CaliforniaInventors: Patricia Cheung, Enrique Iglesia, John Glenn Sunley, David John Law, Aditya Bhan
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Publication number: 20080234512Abstract: The present invention is directed to using methyl acetate from a vinyl acetate-based or a vinyl-or ethylene-alcohol based polymer or copolymer process directly for use in a methanol carbonylation production process to produce acetic acid, acetic anhydride, or a coproduction of each. Methyl acetate is a by-product of commercial polyvinyl-alcohol or alkene vinyl alcohol copolymer-based processes. Generally, this material is processed to recover methanol and acetic acid. Discussed herein is a cost-saving scheme to by-pass the methyl acetate processing at production or plant facilities and utilize the methyl acetate in an integrated methanol carbonylation unit. The scheme discussed eliminates an expensive hydrolysis step often associated with the polymer process.Type: ApplicationFiled: August 23, 2006Publication date: September 25, 2008Inventors: Wayne David Picard, Mark O. Scates, Stephen Charles Webb, Duane Lyle Usrey
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Publication number: 20080221352Abstract: The present invention is directed to using methyl acetate from a vinyl acetate-based or a vinyl- or ethylene-alcohol based polymer or copolymer process directly for use in a methanol carbonylation production process to produce acetic acid, acetic anhydride, or a coproduction of each. Methyl acetate is a by-product of commercial polyvinyl-alcohol or alkene vinyl alcohol copolymer-based processes. Generally, this material is processed to recover methanol and acetic acid. Discussed herein is a cost-saving scheme to by-pass the methyl acetate processing at production or plant facilities and utilize the methyl acetate in an integrated methanol carbonylation unit. The scheme discussed eliminates an expensive hydrolysis step often associated with the polymer process.Type: ApplicationFiled: August 23, 2006Publication date: September 11, 2008Inventors: Mark O. Scates, Stephen Charles Webb