Preparation By Carbonylation Patents (Class 562/517)
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Publication number: 20110021816Abstract: A method of making acetic anhydride or a mixture of acetic anhydride and acetic acid comprising: (a) catalytically reacting a feedstock containing methyl acetate and/or dimethyl ether with carbon monoxide in the presence of a homogeneous rhodium catalyst and methyl iodide in a reactor vessel which contains a substantially anhydrous liquid reaction mixture including acetic acid, acetic anhydride, methyl acetate and/or dimethyl ether, methyl iodide and the homogeneous catalyst, the reactor vessel being operated at a reactor pressure; (b) withdrawing reaction mixture from the reaction vessel and feeding the withdrawn reaction mixture along with additional carbon monoxide to a pre-flasher/post reactor vessel operated at a reduced pressure below the reactor vessel pressure; (c) venting light ends in the pre-flasher vessel and concurrently consuming methyl acetate and/or dimethyl ether in the pre-flasher/post reactor vessel to produce a pre-flash mixture which is enriched in acetic anhydride and diminished in methyType: ApplicationFiled: September 27, 2010Publication date: January 27, 2011Inventor: Mark O. Scates
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Publication number: 20100324332Abstract: A process for the production of acetic acid by the liquid phase carbonylation of an alcohol and/or a reactive derivative thereof in which there is employed a catalyst comprising a complex of rhodium or iridium with a pincer ligand.Type: ApplicationFiled: May 23, 2008Publication date: December 23, 2010Inventors: Emma Louise Carrington-Smith, David John Law, Paul Gerard Pringle, John Glenn Sunley
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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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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: 7790920Abstract: A process for producing acetic acid is disclosed. The process comprises carbonylating methanol to form a reaction mixture comprising a catalyst, catalyst stabilizer, acetic acid, methanol, methyl iodide, methyl acetate, water, and carbon monoxide and introducing at least a portion of the reaction mixture to a distillation column to separate into a bottom steam comprising the catalyst and catalyst stabilizer, a sidedraw stream comprising acetic acid and water, and an overhead stream comprising methanol, methyl acetate, methyl iodide, and water. The process of the invention eliminates the use of flash tank.Type: GrantFiled: September 11, 2008Date of Patent: September 7, 2010Assignee: Lyondell Chemical Technology, L.P.Inventors: Wayne J. Brtko, Michael E. Fitzpatrick, Brian A. Salisbury
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Publication number: 20100204512Abstract: A process for reducing the aldehyde concentration in a target stream of a carbonylation process is disclosed. More specifically, a process for reducing the aldehyde concentration in an internal process stream or feed stream of a carbonylation process is disclosed. In particular, a process in which a target stream comprising a carbonylatable reactant and a first aldehyde concentration is subjected to a reaction comprising a supported catalyst that comprises at least one Group 8 to Group 11 metal at conditions sufficient to reduce the first aldehyde concentration to a second aldehyde concentration is disclosed.Type: ApplicationFiled: April 3, 2007Publication date: August 12, 2010Applicant: CELANESE INTERNATIONAL CORPORATIONInventors: Barbara F M Kimmich, Jeremy J. Patt, Mark O. Scates, James H. Zink
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Patent number: 7737298Abstract: Disclosed is a process for the production of acetic acid or mixtures of acetic acid and acetic anhydride in a carbonylation process wherein a mixture comprising methyl acetate and/or dimethyl ether and methyl iodide is contacting in the liquid phase with carbon monoxide in the presence of a carbonylation catalyst at elevated pressures and temperatures. Methanol, water, or a mixture thereof is added to an acetic anhydride-containing stream within a flash evaporation zone to convert some or all of the acetic anhydride to acetic acid and optionally methyl acetate and to provide heat for the evaporation of a portion of the product effluent produced by the carbonylation process.Type: GrantFiled: June 9, 2006Date of Patent: June 15, 2010Assignee: Eastman Chemical CompanyInventors: Robert Sterling Kline, Gregory Abbott Wellman, Jr., Brandon Tyler Earls, Jerry Lee Bewley
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Patent number: 7629491Abstract: Disclosed is a hydrocarboxylation process for the production of carboxylic acid from olefins wherein an olefin, water, a Group VIII metal hydrocarboxylation catalyst, an onium salt compound are combined in a reaction zone and contacted with carbon monoxide under hydrocarboxylation conditions of pressure and temperature The process does not require or utilize the addition of a hydrogen halide or an alkyl halide exogenous or extraneous to the hydrocarboxylation process.Type: GrantFiled: June 26, 2006Date of Patent: December 8, 2009Assignee: Eastman Chemical CompanyInventors: Joseph Robert Zoeller, Mary Kathleen Moore
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Publication number: 20090270650Abstract: A carbonylation process for producing acetic acid including: (a) carbonylating methanol or its reactive derivatives in the presence of a Group VIII metal catalyst and methyl iodide promoter to produce a liquid reaction mixture including acetic acid, water, methyl acetate and methyl iodide; (b) feeding the liquid reaction mixture at a feed temperature to a flash vessel which is maintained at a reduced pressure; (c) heating the flash vessel while concurrently flashing the reaction mixture to produce a crude product vapor stream, wherein the reaction mixture is selected and the flow rate of the reaction mixture fed to the flash vessel as well as the amount of heat supplied to the flash vessel is controlled such that the temperature of the crude product vapor stream is maintained at a temperature less than 90° F.Type: ApplicationFiled: April 29, 2008Publication date: October 29, 2009Inventor: Jeremy J. Patt
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Publication number: 20090209786Abstract: The present invention relates to carbonylation of methanol, methyl acetate, dimethyl ether or mixtures thereof to produce glacial acetic acid, and more specifically to the manufacture of glacial acetic acid by the reaction of methanol, methyl acetate, dimethyl ether or mixtures thereof with carbon monoxide wherein the product glacial acetic acid contains low impurities.Type: ApplicationFiled: May 21, 2007Publication date: August 20, 2009Inventors: Mark O. Scates, G. Paull Torrence
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Patent number: 7576236Abstract: Integrated processes and systems for producing acetic acid and vinyl acetate are provided. In the processes and systems, a portion of the heat produced during the production of the acetic acid is transferred to the vinyl acetate production and/or purification process and system to facilitate production and/or purification of the vinyl acetate product. The process and systems described herein are useful in conjunction with any of the various known processes for the production of acetic acid and vinyl acetate. The heat of the acetic acid production reaction may be transferred to the vinyl acetate production system by any suitable heat transfer processes and systems. The heat may be provided to the purification section at a variety of locations in the vinyl acetate production and purification systems, depending on the specific configuration of the system to which the processes and systems.Type: GrantFiled: November 13, 2008Date of Patent: August 18, 2009Assignee: Celanese International CorporationInventors: Subramanian Bhaskaran, Angadu Krishnamoorthy (A. K.) Sekar
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Publication number: 20090187043Abstract: The present invention relates to carbonylation of methanol, methyl acetate, dimethyl ether or mixtures thereof to produce glacial acetic acid, and more specifically to the manufacture of glacial acetic acid by the reaction of methanol, methyl acetate, dimethyl ether or mixtures thereof with carbon monoxide wherein the product glacial acetic acid contains low impurities.Type: ApplicationFiled: May 21, 2007Publication date: July 23, 2009Inventors: Mark O. Scates, G. Paull Torrence
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Publication number: 20090163724Abstract: A process for the carbonylation of ethylenically unsaturated compounds including vinyl esters and a process for the production of 3-hydroxy propanoate esters or acids. The process comprises reacting said compound with carbon monoxide in the presence of a source of hydroxyl groups and of a catalyst system. The catalyst system is obtainable by combining: (a) a metal of Group 8, 9 or 10 or a compound thereof: and (b) a bidentate ligand of general formula (I): X1(X2)-Q2-A-R—B-Q1-X3(X4).Type: ApplicationFiled: November 8, 2006Publication date: June 25, 2009Applicant: Lucite International Uk LimitedInventors: Graham Ronald Eastham, Mark Waugh, Philip Ian Richards
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Publication number: 20090156859Abstract: The present invention relates to carbonylation of methanol, methyl acetate, dimethyl ether or mixtures thereof to produce glacial acetic acid, and more specifically to the manufacture of glacial acetic acid by the reaction of methanol, methyl acetate, dimethyl ether or mixtures thereof with carbon monoxide wherein the product glacial acetic acid contains low impurities.Type: ApplicationFiled: May 21, 2007Publication date: June 18, 2009Inventors: Mark O. Scates, G. Paull Torrence
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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: 7470811Abstract: An integrated process for making methanol, acetic acid, and a product from an associated process is disclosed. Syngas (120) is produced by combined steam reforming (109) and autothermal reforming (118) of natural gas (102) where a portion (112) of the natural gas bypasses the steam reformer (109) and is blended with the steam reformer effluent for supply to the autothermal reformer (ATR) (118) with CO2 recycle (110). A portion of the syngas is fed to CO2 removal (122) to obtain the recycle CO2 and cold box (130) to obtain a hydrogen stream (131) and a CO stream (135). The remaining syngas, hydrogen stream (131) and CO2 from an associated process are fed to methanol synthesis (140), which produces methanol and a purge stream (124) supplied to the CO2 removal unit. The methanol is supplied to an acetic acid unit (13)6 with the CO (135) to make acetic acid, which in turn is supplied to a VAM synthesis unit (148).Type: GrantFiled: January 22, 2004Date of Patent: December 30, 2008Assignee: Acetex (Cyprus) LimitedInventor: Daniel Marcel Thiebaut
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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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Patent number: 7465823Abstract: Integrated processes and systems for producing acetic acid and vinyl acetate are provided. In the processes and systems, a portion of the heat produced during the production of the acetic acid is transferred to the vinyl acetate production and/or purification process and system to facilitate production and/or purification of the vinyl acetate product. The process and systems described herein are useful in conjunction with any of the various known processes for the production of acetic acid and vinyl acetate. The heat of the acetic acid production reaction may be transferred to the vinyl acetate production system by any suitable heat transfer processes and systems. The heat may be provided to the purification section at a variety of locations in the vinyl acetate production and purification systems, depending on the specific configuration of the system to which the processes and systems.Type: GrantFiled: March 17, 2004Date of Patent: December 16, 2008Assignee: Celanese International CorporationInventors: Subramanian Bhaskaran, Angadu Krishnamoorthy (A. K.) Sekar
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Publication number: 20080293967Abstract: This invention relates to carbonylation of methanol, methyl acetate, dimethyl ether or mixtures thereof to produce glacial acetic acid, and more specifically to the manufacture of glacial acetic acid by the reaction of methanol, methyl acetate dimethyl ether or mixtures thereof with carbon monoxide wherein the product glacial acetic acid contains low formic acid impurities.Type: ApplicationFiled: May 21, 2007Publication date: November 27, 2008Inventors: Mark O. Scates, G. Paull Torrence
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Publication number: 20080293966Abstract: The present invention relates to carbonylation of methanol, methyl acetate, dimethyl ether or mixtures thereof to produce glacial acetic acid, and more specifically to the manufacture of glacial acetic acid by the reaction of methanol, methyl acetate, dimethyl ether or mixtures thereof with carbon monoxide wherein the product glacial acetic acid contains low impurities.Type: ApplicationFiled: May 21, 2007Publication date: November 27, 2008Inventors: Mark O. Scates, G. Paull Torrence
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Publication number: 20080287706Abstract: An improved apparatus and method of producing acetic acid includes condensing overhead vapor to provide reflux to the light ends column as well as condensing vapor from a central portion of the light ends column to increase capacity. Throughput or load on the light ends column is substantially reduced without compromising product quality.Type: ApplicationFiled: May 17, 2007Publication date: November 20, 2008Inventors: Nathan Kirk Powell, Nathan Jeremy Nagel, Fred Ronald Olsson, Wayne David Picard, Ronald David Shaver, Ismael Torres Tejeda
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Patent number: 7381838Abstract: Process for carrying out catalytic multiphase reactions in a tubular reactor, in which at least three reactants are present in three different phases, wherein the process is carried out in at least one tubular reactor, and the catalyst is present in a continuous phase, at least one reactant is present in this continuous phase, and at least two reactants are present dispersed in the continuous phase and the loading factor B of the tubular reactor is equal to or greater than 0.2. In particular, the multiphase reaction is a hydrocarboxylation of at least one olefin to a carboxylic acid.Type: GrantFiled: March 4, 2005Date of Patent: June 3, 2008Assignee: OXENO Olefinchemie GmbHInventors: Klaus-Diether Wiese, Wilfried Bueschken
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Patent number: 7368597Abstract: A process for the liquid phase carbonylation of an alcohol and/or a reactive derivative thereof in the presence of hydrogen in which there is employed a catalyst comprising rhodium of iridium coordinated with a polydentate ligand.Type: GrantFiled: May 5, 2004Date of Patent: May 6, 2008Assignee: BP Chemicals LimitedInventors: Sander Gaemers, John Glenn Sunley
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Publication number: 20080086015Abstract: A process for the alkoxycarbonylation of a vinyl ester comprising reacting a vinyl ester with carbon monoxide in the presence of an alkanol and a catalyst system. The catalyst system used in the said process is obtainable by combining: a) a metal of Group VIII B or a compound thereof, and b) a bidentate ligand of general formula (I) wherein, R is a covalent bridging group; R1 together with Q2 to which it is attached form an optionally substituted 2-Q2-tricyclo[3.3.1.1 {3,7}]decyl group or derivative thereof(2-PA); R2 and R3 independently represent univalent radicals up to 20 atoms or jointly form a bivalent radical of up to 20 atoms; and Q1 and Q2 each independently represent phosphorous, arsenic or antimony. The process is carried out for the production of a 3-hydroxy propanoate ester or acid of formula (II) CH2 (OH)CH2 C(O) OR28.The process may also be carried out for the production of a lactate ester or acid of formula (III).Type: ApplicationFiled: May 18, 2005Publication date: April 10, 2008Inventor: Graham Eastham
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Patent number: 7348454Abstract: A process for the hydrocarboxylation of an ethylenically unsaturated carboxylic acid, by reacting it with carbon monoxide and a co-reactant selected from the group of water and carboxylic acids in the presence of a catalyst system including: (a) a source of palladium; (b) a bidentate diphosphine of formula (I), R1R2>P—R3—R—R4—P<R5R6 (I) wherein P represents a phosphorus atom; R1, R2, R5 and R6 independently represent the same or different optionally substituted organic groups containing a tertiary carbon atom through which the group is linked to the phosphorus atom; R3 and R4 independently represent optionally substituted alkylene groups and R represents an optionally substituted aromatic group; (c) a source of anions derived from an acid having a pKa of less than 3, as measured at 18° C. in an aqueous solution.Type: GrantFiled: May 17, 2004Date of Patent: March 25, 2008Assignee: Shell Oil CompanyInventors: Eit Drent, Roelof Van Ginkel, Willem Wabe Jager
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Patent number: 7335799Abstract: The present invention relates to novel hydroxyl compounds, compositions comprising hydroxyl compounds, and methods useful for treating and preventing a variety of diseases and conditions such as, but not limited to aging, Alzheimer's Disease, cancer, cardiovascular disease, diabetic nephropathy, diabetic retinopathy, a disorder of glucose metabolism, dyslipidemia, dyslipoproteinemia, hypertension, impotence, inflammation, insulin resistance, lipid elimination in bile, obesity, oxysterol elimination in bile, pancreatitis, pancreatitius, Parkinson's disease, a peroxisome proliferator activated receptor-associated disorder, phospholipid elimination in bile, renal disease, septicemia, metabolic syndrome disorders (e.g., Syndrome X), thrombotic disorder. Compounds and methods of the invention can also be used to modulate C reactive protein or enhance bile production in a patient.Type: GrantFiled: December 23, 2003Date of Patent: February 26, 2008Assignee: Esperion Therapeutics, Inc.Inventors: Jean-Louis Henri Dasseux, Carmen Daniela Oniciu
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Patent number: 7276626Abstract: A process for the production of a carboxylic acid and/or the alcohol ester of a carboxylic acid by carbonylating an alcohol and/or a reactive derivative thereof with carbon monoxide employing as the carbonylation catalyst, cobalt, rhodium or iridium coordinated with a tridentate ligand.Type: GrantFiled: May 5, 2004Date of Patent: October 2, 2007Assignee: BP Chemicals LimitedInventors: Sander Gaemers, John Glenn Sunley
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Patent number: 7265242Abstract: A process for the carbonylation of unsaturated compounds by contacting the unsaturated compound with carbon monoxide in the presence of a catalyst system comprising: (a) a source of palladium and/or platinum; and (b) an unsymmetrical bidentate diphosphine ligand of formula I, R1R2>P1?R3?P2<R4R5??(I) wherein P1 and P2 represent phosphorus atoms; R3 represents a divalent organic bridging group; and R1, R2, R4 and R5 each individually, or R1 and R2 jointly, and/or R4 and R5 jointly represent organic groups that are covalently linked to the phosphorus; and wherein R1, R2, R4 and R5 are chosen in such way, that the phosphino group R1R2>P1 differs from the phosphino group P2<R4R5.Type: GrantFiled: November 24, 2004Date of Patent: September 4, 2007Assignee: Shell Oil CompanyInventors: Eit Drent, Willem Wabe Jager, Robert Ian Pugh
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Patent number: 7253304Abstract: Disclosed is a carbonylation process wherein a mixture of a dialkyl carbonate and halide compound is contacted with carbon monoxide in the presence of a metal selected from Group VIII of the Periodic Table to co-produce carbon dioxide and a carbonyl compound selected from a carboxylic acid, an alkyl carboxylate ester, a carboxylic acid anhydride or a mixture of any two or more thereof. The carbon dioxide co-product of the process may be recovered, and sold or further reacted with a suitable substrate to produce useful chemicals such as urea or cyclic carbonates.Type: GrantFiled: June 20, 2006Date of Patent: August 7, 2007Assignee: Eastman Chemical CompanyInventor: Gerald Charles Tustin
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Patent number: 7223883Abstract: An improvement of the methanol carbonylation process for manufacturing acetic acid is disclosed. Specifically disclosed is a method for removing permanganate reducing compounds (“PRC's”) from the condensed light ends overhead stream, including (a) distilling at least a portion of the condensed light ends overhead to yield a PRC enriched second overhead stream; (b) extracting the second overhead stream with water and separating therefrom an aqueous stream containing PRC's; and (c) returning at least a portion of the extracted second overhead to the second distiller.Type: GrantFiled: March 2, 2004Date of Patent: May 29, 2007Assignee: Celanese International CorporationInventors: Wayne D. Picard, Jose J. Arturo Talancon, David A. Trueba, Mark O. Scates, Raymond J. Zinobile
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Patent number: 7115774Abstract: In a process for liquid phase carbonylation of alcohols by carbon monoxide, the carbonylation reaction is carried out in a reaction zone at a temperature of 50° C. to 150° C. at a pressure in the range 0.5 MPa to 20 MPa in the presence of at least one catalyst comprising at least one rhodium and/or iridium complex and a halogenated promoter in at least one non-aqueous ionic liquid comprising at least one salt with general formula Q+A?, in which Q+ represents a quaternary ammonium and/or a quaternary phosphonium cation, said salt having a melting point of less than 90° C.; the non-aqueous ionic liquid containing at least the major portion of the catalyst is separated; and the separated non-aqueous ionic liquid containing at least the major portion of the catalyst is returned to the reaction zone.Type: GrantFiled: May 22, 2003Date of Patent: October 3, 2006Assignee: Institut Francais du PetroleInventors: Lionel Magna, Helene Olivier-Bourbigou, Stephane Harry, Dominique Commereuc
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Patent number: 6916951Abstract: Disclosed is a continuous process wherein carbon monoxide, a carbonylatable reactant, and a halide in the gas phase are contacted with a non-volatile catalyst solution comprising an ionic liquid and a Group VIII metal to produce a carbonylation product in the gas phase. The process is useful for the continuous preparation of acetic acid by the carbonylation of methanol.Type: GrantFiled: May 9, 2003Date of Patent: July 12, 2005Assignee: Eastman Chemical CompanyInventors: Gerald Charles Tustin, Regina Michelle Moncier
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Patent number: 6916954Abstract: The invention relates to a catalyst system for carbonylating olefinically or acetylenically unsaturated compounds with carbon monoxide and a nucleophile compound, containing (a) palladium; (b) a phosphine and (c) a polymer containing nitrogen which is soluble in the reaction mixture, with the exception of polyvinyl polymers with aromatic radicals containing nitrogen on the polymer chain. The invention also relates to a method for carbonylation in the presence of one such catalyst system.Type: GrantFiled: September 25, 2001Date of Patent: July 12, 2005Assignee: BASF AktiengesellschaftInventors: Martin Schäfer, Michael Slany, Edgar Zeller, Michael Röper, Michael Schulz, Günther Grimm
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Patent number: 6858753Abstract: The present invention provides an improved process for the production of carboxylic acids by the carbonylation of alcohol. The process involves contacting an alcohol with carbon monoxide in the presence of a nickel compound, a heterocyclic organic compound and an iodide promoter to produce the corresponding carboxylic acid. The improvement relates to the use of heterocyclic organic compound as a promoter containing at least two heteroatoms of which at least one is selected independently from S or N, which provides an inexpensive and stable catalyst system.Type: GrantFiled: March 14, 2002Date of Patent: February 22, 2005Assignee: Council of Scientific and Industrial ResearchInventors: Raghunath Vitthal Chaudhari, Sunil Shankar Joshi, Ashutosh Anant Kelkar, Sunil Sadashiv Divekar
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Publication number: 20040242924Abstract: Formic acid and a carboxylic acid having at least two carbon atoms and/or derivatives thereof are prepared jointly by a process in whichType: ApplicationFiled: February 3, 2004Publication date: December 2, 2004Inventors: Peter Zehner, Jorg Pastre, Wolfram Stuer
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Patent number: 6784313Abstract: A process for producing a carboxylic acid having (n+1) carbon atoms, which includes carbonylating an alcohol having n carbon atoms, and/or an ester of the alcohol and the carboxylic acid in each alkyl group with carbon monoxide in the presence of a catalytic system containing a rhodium catalyst. The process uses a reaction medium for the carbonylation that includes: (1) a rhodium catalyst, (2) an organic halide corresponding to said alcohol, (3) an ester of the alcohol and the carboxylic acid, (4) the carboxylic acid, optionally (5) water, a haloid acid, an inorganic halogen salt or an acetate, and (6) a cocatalyst selected from arginine, N-acetyl alanine, or nitrogen- and oxygen-containing organic compounds.Type: GrantFiled: October 4, 2002Date of Patent: August 31, 2004Assignee: China Petrochemical Development CorporationInventors: Chia Jung Tsai, Yao Lung Liu, Hsi Chin Tsai
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Patent number: 6706912Abstract: Process for the carbonylation of ethylenically unsaturated compounds having 3 or more carbon atoms by reaction with carbon monoxide and an hydroxyl group containing compound in the presence of a catalyst system. The catalyst system includes (a) a source of palladium cations; (b) a bidentate diphosphine of formula I, R1R2>P—R3—R—R4—P<R5R6 (I) wherein P represents a phosphorus atom; R1, R2, R5 and R6 independently represent the same or different optionally substituted organic groups containing a tertiary carbon atom through which the group is linked to the phosphorus atom; R3 and R4 independently represent optionally substituted alkylene groups and R represents an optionally substituted aromatic group; (c) a source of anions derived from an acid having a pKa less than 3, as measured at 18° C. in an aqueous solution. The process is carried out in the presence of an aprotic solvent.Type: GrantFiled: March 13, 2001Date of Patent: March 16, 2004Assignee: Shell Oil CompanyInventors: Eit Drent, Willem Wabe Jager
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Patent number: 6686500Abstract: A process for the production of acetic acid by reacting carbon monoxide with methanol and/or a reactive derivative thereof in a liquid reaction composition comprising an iridium carbonylation catalyst, methyl iodide, methyl acetate, water and acetic acid characterised in that there is also present in the reaction composition a monodentate phosphine oxide compound in an amount of up to and including 200 mol per gram atom of iridium.Type: GrantFiled: October 31, 2000Date of Patent: February 3, 2004Assignee: BP Chemicals LimitedInventor: Robert John Watt
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Patent number: 6677480Abstract: A process for monitoring and controlling reactor conditions during the production of acetic acid by the catalyzed carbonylation of methanol is provided. The process of the present invention comprises measuring the density of the heavy phase of the light ends distillation column in the purification system of the carbonylation process. The density measurement is used to adjust the feed of methanol and/or to regulate the temperature in the reaction zone to optimize reactor conditions. The density measurement may also be used to adjust other parameters in the reactor system. The invention is also directed to the system for manufacturing acetic acid based on the process control procedure described.Type: GrantFiled: January 28, 2002Date of Patent: January 13, 2004Assignee: Celanese International CorporationInventors: Michael E. Huckman, G. Paull Torrence, Hung-Cheun Cheung
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Patent number: 6646154Abstract: A vapor-phase carbonylation method for producing esters and carboxylic acids from reactants comprising lower alkyl alcohols, lower alkyl alcohol generating compounds, and mixtures thereof. The method includes contacting the reactants and carbon monoxide in a carbonylation zone of a carbonylation reactor under vapor-phase carbonylation conditions with a catalyst having a catalytically effective amount of a Group VIII metal selected from platinum or palladium, and tungsten which are associated with a solid catalyst support material.Type: GrantFiled: June 20, 2001Date of Patent: November 11, 2003Assignee: Eastman Chemical CompanyInventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
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Patent number: 6642413Abstract: A continuous preparative process, including monitoring production, for acetic acid, methyl acetate or a mixture thereof, by carbonylation, in an industrial installation, of methanol or a carbonylatable derivative of methanol with carbon monoxide in a liquid phase in the presence of water and a homogeneous catalyst system. In a reaction zone I, the carbonylation is carried out in the liquid phase at a temperature of 150 to 250° C., under a pressure of 5·105 to 200·105 Pa and with venting of part of a gaseous canopy above a liquid phase level in said reactor. Then, in a vaporization or flash zone II, a liquid originating from the zone I at a pressure below that of zone I is partially vaporized to form a liquid fraction which is recycled into the reactor, and in a purification zone III, a vaporized fraction originating from flash zone II is distilled on a distillation column.Type: GrantFiled: September 13, 2001Date of Patent: November 4, 2003Assignee: Acetex ChimieInventor: Daniel Thiebaut
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Publication number: 20030204110Abstract: A method for production of pivalic acid comprising the steps of: (a) reacting isobutylene, carbon monoxide, and a first catalyst to produce a reaction mixture; (b) contacting the reaction mixture with water, thereby producing a crude acid product having pivalic acid and oligomeric neo-carboxylic acid; (c) separating the pivalic acid and the oligomeric neo-carboxylic acid from the crude acid product; (d) reacting the oligomeric neo-carboxylic acid with a source of carbon monoxide at a temperature of less than 200° C. in the presence of a second catalyst to produce a C5 carbocation product, wherein the first and second catalyst are either the same or different; and (e) reacting the C5 carbocation product with water; thereby producing pivalic acid having an overall yield of at least 80 wt. %.Type: ApplicationFiled: May 9, 2003Publication date: October 30, 2003Inventors: Edmund J. Mozeleski, Richard H. Schlosberg, Dennis J. Davoren, Carl Robert Beck, Linda J. Broadbelt, Ned C. Haubein
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Publication number: 20030204107Abstract: The present invention relates to process for improving the stability and/or preventing the deactivation of the catalyst in processes of manufacture of acetic acid and/or of methyl acetate according to which processes, in a first step, referred to as the reaction step, at least one methyl formate isomerisation reaction is carried out in liquid phase, in the presence of carbon monoxide and of a catalytic system comprising at least one halogenated promoter and at least one iridium-based catalytic compound, and, in a second step, referred to as the flash step, the partial vaporisation of the reaction medium originating from the first step is carried out in a separator referred to as the flash separator, characterised in that it consists in maintaining an overall content of formic acid and of methyl formate at least equal to 1% by weight of said liquid fraction, preferably between 1 and 50%, preferably between 1 and 30%, by weight with respect to said liquid fraction, in the non-vaporised liquid fraction originatiType: ApplicationFiled: May 1, 2003Publication date: October 30, 2003Applicant: ACETEX CHIMIEInventors: Thiebaut Daniel, Patois Carl, Layeillon Lise, Marchand Daniel
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Patent number: 6617471Abstract: A vapor-phase carbonylation method for producing esters and carboxylic acids from reactants comprising lower alkyl alcohols, lower alkyl alcohol generating compounds, and mixtures thereof. The method includes contacting the reactants and carbon monoxide in a carbonylation zone of a carbonylation reactor under vapor-phase conditions with a catalyst having a catalytically effective amount of iridium and tin associated with a solid carrier material.Type: GrantFiled: June 20, 2001Date of Patent: September 9, 2003Assignee: Eastman Chemical CompanyInventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
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Publication number: 20030149298Abstract: A method for production of pivalic acid comprising the steps of: (a) reacting isobutylene, carbon monoxide, and a first catalyst to produce a reaction mixture; (b) contacting the reaction mixture with water, thereby producing a crude acid product having pivalic acid and oligomeric neo-carboxylic acid; (c) separating the pivalic acid and the oligomeric neo-carboxylic acid from the crude acid product; (d) reacting the oligomeric neo-carboxylic acid with a source of carbon monoxide at a temperature of less than 200° C. in the presence of a second catalyst to produce a C5 carbocation product, wherein the first and second catalyst are either the same or different; and (e) reacting the C5 carbocation product with water; thereby producing pivalic acid having an overall yield of at least 80 wt. %.Type: ApplicationFiled: March 31, 2003Publication date: August 7, 2003Inventors: Edmund J. Mozeleski, Richard H. Schlosberg, Dennis J. Davoren, Carl Robert Beck, Linda J. Broadbelt, Ned C. Haubein
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Publication number: 20030105348Abstract: Disclosed in a process for making (1) a compound of the formula NC—CH2—CH2—CH2—CH2—CO2R′, wherein R′ is H or C1 to C12 alkyl, or (2) adipic acid or (3) dimethyl adipate, using as the substrate, 3-pentenenitrile, (2) 3-pentenoic acid or methyl 3-pentenoate, respectively, by contacting the substrate with carbon monoxide and a nucleophile in the presence of a Group VIII metal, a selected ligand, and an acid promoter. The nucleophile, which (a) an alcohol or water, or (b) water or (c) methanol, respectively, in the presence of a Group VIII metal, preferably palladium, a selected phosphine ligand, and an acid promoter.Type: ApplicationFiled: November 19, 2001Publication date: June 5, 2003Inventors: Emilio E. Bunel, David A. Clark
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Patent number: 6552221Abstract: A method of real time process control in a reaction system for the production of acetic acid from the carbonylation of methanol. Reaction system samples are collected from columns and/or transfer lines downstream of a reactor vessel, and the concentration of one or more components in the sample is measured by an infrared analyzer. The concentration measurements are then used to make adjustments in the concentration of components in the reaction system, directly or indirectly, such as by adjusting the temperature profile in a particular column, the flow rate of solution in to or out of a column, the vent gas rate out of the reactor or a column, or the addition or extraction of a component to or from the solution. For optimum process control, the measurements are transmitted to a control unit for real time analysis, and the adjustments are made substantially instantly after the infrared analysis.Type: GrantFiled: September 29, 2000Date of Patent: April 22, 2003Assignee: Millenium Petrochemicals, Inc.Inventors: Noel Hallinan, James A. Hinnenkamp, Javan Shelly
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Patent number: 6521783Abstract: This invention relates in part to a processes for the conversion of a feedstock stream comprising carbon monoxide and hydrogen to a product stream comprising at least one of an ester, acid, acid anhydride and mixtures thereof. This invention also relates in part to processes for converting an alcohol and/or ether feedstock to oxygenated products, e.g., esters, acids, acid anhydrides and mixtures thereof. The processes and catalysts are especially suitable for the production of acetic acid and methyl acetate from a synthesis gas feedstock or from an alcohol and/or ether feedstock.Type: GrantFiled: July 10, 2000Date of Patent: February 18, 2003Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Richard William Wegman, David McNeill Somerville, Barry Brent Fish, Raymond Edwin Rooks, Chinsoo Stephen Lee, Paul Frank Bryan, William J. Bartley, David Michael Anthony Minahan, Fungau Ho
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Publication number: 20030028049Abstract: A method for production of pivalic acid comprising the steps of: (a) reacting isobutylene, carbon monoxide, and a first catalyst to produce a reaction mixture; (b) contacting the reaction mixture with water, thereby producing a crude acid product having pivalic acid and oligomeric neo-carboxylic acid; (c) separating the pivalic acid and the oligomeric neo-carboxylic acid from the crude acid product; (d) reacting the oligomeric neo-carboxylic acid with a source of carbon monoxide at a temperature of less than 200° C. in the presence of a second catalyst to produce a C5 carbocation product, wherein the first and second catalyst are either the same or different; and (e) reacting the C5 carbocation product with water; thereby producing pivalic acid having an overall yield of at least 80 wt. %.Type: ApplicationFiled: July 9, 2001Publication date: February 6, 2003Inventors: Edmund J. Mozeleski, Richard H. Schlosberg, Dennis J. Davoren, Carl Robert Beck, Linda J. Broadbelt, Ned C. Haubein
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Patent number: 6472558Abstract: A process for the production of acetic acid by reacting carbon monoxide with methanol and/or a reactive derivative thereof in a liquid reaction composition comprising an iridium carbonylation catalyst, methyl iodide, methyl acetate, water and acetic acid characterized in that there is also present in the reaction composition a polydentate phosphine oxide compound in an amount of less than 10 mol per gram atom of iridium.Type: GrantFiled: October 31, 2000Date of Patent: October 29, 2002Assignee: BP Chemicals LimitedInventors: Lesley Ann Key, David John Law