Preparation By Carbonylation Patents (Class 562/517)
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Patent number: 6465680Abstract: A process for preparing a malonic acid monoester or &bgr;-ketoester from an epoxide includes the steps of reacting an epoxide with carbon monoxide and an alcohol in the presence of a catalytic amount of a cobalt compound and at least one promoter to produce a &bgr;-hydroxyester, separating the &bgr;-hydroxyester from the cobalt compound and the promoter, and oxidizing the &bgr;-hydroxyester to produce a malonic acid monoester or &bgr;-ketoester.Type: GrantFiled: June 20, 2001Date of Patent: October 15, 2002Assignee: Samsung Electronics Co., Ltd.Inventors: Byeong No Lee, In-Sun Jung, Eun Joo Jang
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Publication number: 20020137660Abstract: The present invention relates to a process for the preparation of alkylcarboxylic allyl esters by reacting allyl alcohol and alkylcarboxylic acids.Type: ApplicationFiled: March 18, 2002Publication date: September 26, 2002Inventors: Walter Kuhn, Gerhard Senft
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Patent number: 6452043Abstract: A method for producing esters, carboxylic acids and mixtures thereof includes contacting, under carbonylation conditions, lower alkyl alcohols, ethers, lower alkyl alcohol derivatives and mixtures thereof and carbon monoxide with a catalyst having a catalytically effective amount a metal selected from iron, cobalt, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum, tin and mixtures thereof associated with a carbonized polysulfonated divinylbenzene-styrene copolymer matrix. In a preferred aspect of the invention the method is called out under vapor-phase conditions.Type: GrantFiled: April 5, 2000Date of Patent: September 17, 2002Assignee: Eastman Chemical CompanyInventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
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Patent number: 6420304Abstract: The invention relates to a polymer-supported carbonylation catalyst and its use in a process for preparing organic carboxylic acid or anhydride having n+1 carbon atoms. The invention relates also to a process for preparing organic carboxylic acid or anhydride having n+1 carbon atoms by carbonylating with monoxide, in the presence of the above-mentioned carbonylation catalyst, on alcohols having n carbon atoms, ethers having 2n carbon atoms or esters formed from said alcohols and acids. In particular, the invention relates to a process for preparing acetic acid by carbonylating methanol with carbon monooxide in the presence of said carbonylation catalyst. By using said carbonylation catalyst, the temperature for carbonylation can be lowered to about 160° C. with a reaction rate better than that of a traditional process, while the tendency of catalyst precipitation in the course of carbonylation can be improved also.Type: GrantFiled: April 20, 2000Date of Patent: July 16, 2002Assignee: China Petrochemical Development CorporationInventors: Chia-Jung Tsai, Yao-Lung Liu, Hsi-Chin Tsai
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Patent number: 6395927Abstract: A method for preparing acetic acid and/or methyl acetate by simultaneous isomerization and carbonylation reactions. A reaction mixture is provided containing at least one reagent which provides formyl radicals and at least one further reagent which provides methyl radicals, together with water in an amount of at most 5% by weight, carbon monoxide at a partial pressure between 0.1·105 Pa and 25·105 Pa, a solvent and a catalytic system which contains at least one halogenated promoter and at least one iridium-based compound. In a typical reaction mixture, methyl formate is isomerized to form acetic acid according to the reaction: HCOOCH3CH3COOH while methanol undergoes carbonylation to form acetic acid according to the reaction: CH3OH+COCH3COOH The reagent which provides the formyl radicals is kept at or below 20% by weight of the reaction mixture, while the molar ratio of methyl radicals to formyl radicals in the mixture is greater than 1.Type: GrantFiled: September 23, 1998Date of Patent: May 28, 2002Assignee: Acetex ChimieInventors: Carl Patois, Robert Perron, Daniel Thiebaut
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Publication number: 20020058834Abstract: A process for the preparation of amino carboxylic acids, N-acyl amino carboxylic acids, or derivatives thereof by carboxymethylation of an amide, amide precursor or amide source compound in the presence of a carboxymethylation catalyst precursor and a promoter is provided. A carboxymethylation reaction mixture is formed by introducing a promoter, an amide, amide precursor or amide source compound, carbon monoxide, hydrogen, an aldehyde or aldehyde source compound, and a carboxymethylation catalyst precursor into a carboxymethylation reaction zone. In a preferred embodiment, the promoter is a supported noble metal promoter. In another preferred embodiment, the amide compound and aldehyde are selected to yield an N-acyl amino carboxylic acid which is readily converted to N-phosphonomethyl)glycine, or a salt or ester thereof.Type: ApplicationFiled: June 1, 2001Publication date: May 16, 2002Inventor: Thaddeus S. Franczyk
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Patent number: 6362366Abstract: There is provided a process control method for the production of acetic acid by the catalyzed carbonylation of methanol and a process for the manufacture of acetic acid using the process control method. The process control method comprises measuring various reactor component concentrations, specifically the active catalyst species, methyl iodide, water and methyl acetate by means of an infrared analyzer, and adjusting in response thereto the concentrations of at least the catalyst species, methyl iodide and water to optimize the acetic acid reaction.Type: GrantFiled: July 6, 2000Date of Patent: March 26, 2002Assignee: Millennium Petrochemicals IncInventors: Noel Hallinan, James A. Hinnenkamp
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Patent number: 6355595Abstract: A solid supported catalyst suitable for the vapor phase carbonylation of lower aliphatic alcohols, ethers, ester, and ester-alcohol mixtures, and desirably, methanol, to produce acetic acid, methyl acetate and mixtures thereof. The solid supported catalyst includes an effective amount of iridium and at least one second metal selected from group metals of the periodic table of elements, their respective salts and mixtures thereof associated with a solid support material. Desirably, the support material is selected from carbon, activated carbon, pumice, alumina, silica, silica-alumina, magnesia, diatomaceous earth, bauxite, titania, zirconia, clay, magnesium silicate, silicon carbide, zeolites, ceramics and combinations thereof.Type: GrantFiled: August 25, 1999Date of Patent: March 12, 2002Assignee: Eastman Chemical CompanyInventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
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Patent number: 6355837Abstract: A method for producing esters and carboxylic acids from lower alkyl alcohols, ethers, esters and ester-alcohol reactant mixtures and includes the step of contacting a vaporous mixture of the reactants, carbon monoxide and a halide with a supported catalyst under vapor-phase carbonylation conditions. The catalyst includes iridium and a second metal selected from group 4 (titanium, zirconium, hafnium) metals of the periodic table of elements. Desirably, the iridium and secondary metal are deposited on activated carbon as a support material. In a preferred aspect of the invention, the vapor phase carbonylation process is useful for preparing acetic acid, methyl acetate or a mixture thereof.Type: GrantFiled: August 25, 1999Date of Patent: March 12, 2002Assignee: Eastman Chemical CompanyInventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
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Patent number: 6353132Abstract: A method for producing esters and carboxylic acids from lower alkyl alcohols, ethers, esters and ester-alcohol reactant mixtures and includes the step of contacting a vaporous mixture of the reactants, carbon monoxide and a halide with a supported catalyst under vapor-phase carbonylation conditions. The catalyst includes iridium and a second metal selected from group 5 (vanadium, niobium, tantalum) metals of the periodic table of elements. Desirably, the iridium and secondary metal are deposited on activated carbon as a support material. In a preferred aspect of the invention, the vapor phase carbonylation process is useful for preparing acetic acid, methyl acetate or a mixture thereof.Type: GrantFiled: August 25, 1999Date of Patent: March 5, 2002Assignee: Eastman Chemical CompanyInventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
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Patent number: 6323364Abstract: The method of the present invention provides an improvement upon prior art methanol carbonylation methods which substantially reduces the production of carbonyl impurities. The production of carbonyl impurities, particularly acetaldehyde, crotonaldehyde, and 2-ethyl crotonaldehyde, in methanol carbonylation reactions has been found to decrease by maintaining less than about 4.5 wt % methyl iodide in the reaction medium during the course of the reaction.Type: GrantFiled: August 31, 1999Date of Patent: November 27, 2001Assignee: Celanese International CorporationInventors: Pramod Agrawal, Hung-Cheun Cheung, Darrell A. Fisher, Valerie Santillan, Mark O. Scates, Elaine C. Sibrel, G. Paul Torrence
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Publication number: 20010043895Abstract: A method for generating a solution containing rhodium at a concentration of at least 0.01 M and preferably at least 0.20 M, comprising treating solid rhodium iodide or other solid source of rhodium with a reducing agent selected from a source of hydrazine, hydrazine hydrate, hydrazinium salts, organic derivatives of hydrazine, hypophosphorous acid and salts of hypophosphorous acid.Type: ApplicationFiled: May 11, 2001Publication date: November 22, 2001Applicant: Haldor Topsoe A/SInventor: Niels C. Schiodt
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Patent number: 6303813Abstract: The method of the present invention provides an improvement upon prior art methanol carbonylation methods which substantially reduces the production of carbonyl impurities. The production of carbonyl impurities, particularly acetaldehyde, crotonaldehyde, and 2-ethyl crotonaldehyde, in methanol carbonylation reactions has been found to decrease by maintaining a partial pressure of hydrogen between about 0.1 and 4 psia at reaction total pressure of from about 15 to about 40 atmospheres total reaction pressure.Type: GrantFiled: August 31, 1999Date of Patent: October 16, 2001Assignee: Celanese International CorporationInventors: Mark O. Scates, Valerie Santillan, Pramod Agrawal, G. Paull Torrence, R. Jay Warner
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Patent number: 6268530Abstract: Process to separate linear 5-formylvaleric acid from a mixture of 5- and 3- and 4-formylvaleric acids, wherein the separation is performed by fractional extraction with two immiscible solvents of which one solvent is an aqueous solvent and the other solvent is an organic solvent, in which the organic solvent has a higher or lower affinity for 5-formylvaleric acid than its affinity for the 3-formylvaleric acids and for the 4-formylvaleric acid. Furthermore the invention relates to an improved process to prepare ∈-caprolactam starting from a mixture of branched and linear formylvaleric acids or starting from pentenoic acid.Type: GrantFiled: January 5, 1998Date of Patent: July 31, 2001Assignees: DSM N.V., E. I. DuPont de Nemours and CompanyInventors: Imre Toth, Onko Gelling, Rudolf P. M. Guit, Antonius J. F. Simons, Simon Hans H. Niemann
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Publication number: 20010007912Abstract: A process for the co-production of acetic anhydride and acetic acid which process comprises introducing a carbonylatable feedstock comprising methyl acetate and/or dimethyl ether and optionally also comprising methanol and/or water, to a carbonylation reactor in which there is maintained a liquid reaction composition comprising acetic anhydride, acetic acid, rhodium carbonylation catalyst, alkyl iodide co-catalyst and an iodide salt promoter consisting essentially of an alkali metal iodide and/or alkaline earth metal iodide, contacting said carbonylatable feedstock with carbon monoxide in said liquid reaction composition to produce acetic anhydride and acetic acid, and introducing to the carbonylation reactor methyl formate and/or formic acid in the range from 0.1 to 20% by weight of the total feed of liquid components to the reactor.Type: ApplicationFiled: December 26, 2000Publication date: July 12, 2001Inventors: Robert Edward Allan, Derrick John Watson
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Patent number: 6160163Abstract: A method for the vapor-phase carbonylation of lower alkyl alcohols to esters and optionally, carboxylic acids using a catalyst having a platinum on a solid support material as a first component and a vaporous halide as a second component. Desirably, the catalyst includes platinum on an activated carbon support and the vaporous halide is selected from hydrogen halides, alkyl halides and aryl halides having up to 12 carbon atoms, and mixtures thereof.Type: GrantFiled: February 16, 1999Date of Patent: December 12, 2000Assignee: Eastman Chemical CompanyInventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
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Patent number: 6153792Abstract: A process for the production of a carboxylic acid in the presence of solid catalyst particles that employs a flash step with a liquid wash is disclosed. This process helps prevent the buildup of deposits of solid catalyst particles, attrited solid catalyst particles, and heavy by-products in the flash zone. This invention is useful for the production of carboxylic acids, especially acetic acid.Type: GrantFiled: December 18, 1998Date of Patent: November 28, 2000Assignee: UOP LLCInventors: William A. Leet, Santi Kulprathipanja
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Patent number: 6130355Abstract: An anhydrous process for the production of acetic acid by the reaction of methanol, and/or dimethyl ether, with a gaseous reactant comprising carbon monoxide and hydrogen, the hydrogen being present in an amount less than 9 mole %, in the presence of a catalyst system comprising at least one noble metal of Group VIII of the Periodic Table as catalyst, a halo-compound as co-catalyst and an iodide salt as catalyst stabiliser which process comprises feeding methanol, and/or dimethyl ether, and gaseous reactant to a carbonylation reactor in which there is maintained a liquid reaction composition comprising: (i) methyl acetate in an amount from 1 to 35% w/w, (ii) acetic anhydride in an amount up to 8% w/w, (iii) halo-compound in an amount from 3 to 20% w/w, (iv) Group VIII noble metal catalyst in an amount from 1 to 2000 ppm, (v) sufficient iodide salt to provide from 0.5 to 20% by weight iodine as I.sup.- and (vi) acetic acid comprising the remainder of the composition.Type: GrantFiled: December 24, 1998Date of Patent: October 10, 2000Assignee: BP Chemicals LimitedInventor: Michael David Jones
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Patent number: 6114576Abstract: A process for the production of a carboxylic acid in the presence of solid catalyst particles that uses the exothermic heat of reaction with high efficiency in recovering the carboxylic acid product is disclosed. This process uses indirect heat exchange to transfer the heat of reaction to another stream, without the need for an additional heat transfer fluid such as steam. This invention is especially applicable to the production of acetic acid.Type: GrantFiled: December 18, 1998Date of Patent: September 5, 2000Assignee: UOP LLCInventors: William A. Leet, Santi Kulprathipanja, Bruce A. Briggs
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Patent number: 6103934Abstract: There is provided a process control method for the production of acetic acid by the catalyzed carbonylation of methanol and a process for the manufacture of acetic acid using the process control method. The process control method comprises measuring various reactor component concentrations, specifically the active catalyst species, methyl iodide, water and methyl acetate by means of an infrared analyzer, and adjusting in response thereto the concentrations of at least the catalyst species, methyl iodide and water to optimize the acetic acid reaction.Type: GrantFiled: December 18, 1998Date of Patent: August 15, 2000Assignee: Millennium Petrochemicals, Inc.Inventors: Noel Hallinan, James A. Hinnenkamp
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Patent number: 6090986Abstract: Esters of branched C.sub.9 alcohols suitable as plasticizers are formed by esterification of a C.sub.9 alcohol produced by the aldol condensation from propanal and a C.sub.6 aldehyde and hydrogenation, the propanal optionally having been made from natural gas streams.Type: GrantFiled: October 27, 1997Date of Patent: July 18, 2000Assignee: Exxon Chemical Patents Inc.Inventors: Allen David Godwin, Richard Henry Schlosberg, Frank Hershkowitz, Michael G. Matturro, Gabor Kiss, Kirk Christian Nadler, Philippe Louis Buess, Richard C. Miller, Paul William Allen, Harry William Deckman, Raf Caers, Edmund John Mozeleski, Robert P Reynolds, Francis Joseph Healy
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Patent number: 6084124Abstract: The present invention is a method to produce an unsaturated carboxylic acid which includes the steps of: providing an epoxy compound; contacting the epoxy compound with carbon monoxide in the presence of a catalytically effective amount of a catalyst system comprising tin and cobalt under conditions effective for carbonylation of the epoxy; and recovering a .alpha.-.beta. unsaturated carboxylic acid product. The preferred epoxy is ethylene oxide which is reacted to acrylic acid by the method of the present invention.Type: GrantFiled: February 4, 1999Date of Patent: July 4, 2000Assignee: Shell Oil CompanyInventors: Lynn Henry Slaugh, Thomas Clayton Forschner
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Patent number: 6066762Abstract: A process for the production of a carbonyl compound such as acetic acid by reacting a carbonylatable compound such as methanol with a carbon monoxide in the presence of a carbonylation catalyst containing a noble metal complex supported on a porous, cross-linked vinylpyridine resin at a temperature of 140-250.degree. C., a carbon monoxide partial pressure of 7-30 kg/cm.sup.2 and a hydrogen partial pressure of 0.1-5 kg/cm.sup.2 to obtain a liquid product containing the carbonyl compound and an unreacted CO-containing gas product. The water content and the carbonylation degree of the liquid product within the reactor are maintained at 0.5-10% by weight and 0.5-0.9, respectively, The carbonyl compound is separated from the liquid product in a flasher and/or a distillation tower formed of titanium or a titanium-palladium alloy. The liquid product is introduced into a pressure reducing valve and then mixed with the CO-containing gas product before being fed to the flasher and/or distillation tower.Type: GrantFiled: December 23, 1997Date of Patent: May 23, 2000Assignee: Chiyoda CorporationInventors: Noriyuki Yoneda, Takeshi Minami, Yoshihiro Nakagawa, Ikuo Ohta, Akihisa Yamaguchi, Hideki Sugiyama, Fumihiko Uemura
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Patent number: 6013816Abstract: Process for the preparation of a linear .omega.-formyl-carboxylic acid or a corresponding linear formylnitrile compound starting from an internally unsaturated C.sub.4 -C.sub.12 carboxylic acid or a corresponding ester or nitrile by means of hydroformylation in the presence of carbon monoxide, hydrogen and a catalyst system, wherein the hydroformylation is carried out in an aqueous medium and in that the catalyst system comprises platinum and a water-soluble organic bidentate ligand.Type: GrantFiled: July 5, 1996Date of Patent: January 11, 2000Assignee: DSM NVInventors: Onko J. Gelling, Imre Toth
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Patent number: 6008408Abstract: The present invention relates to a process for the hydroxycarbonylation of pentenoic acids. By the process, one or a number of pentenoic acids are hydroxycarbonylated to adipic acid, by carbon monoxide and water, in the presence of a catalyst based on iridium and/or rhodium and of at least one iodinated promoter. The reaction mixture obtained is subjected to a refining operation, after having optionally been concentrated, making it possible to separate at least a part of the catalyst. The catalyst thus separated is recycled to an operation for the hydroxycarbonylation of pentenoic acids, of butadiene, or of butadiene derivatives.Type: GrantFiled: July 11, 1995Date of Patent: December 28, 1999Assignee: Rhone-Poulenc ChimieInventors: Philippe Denis, Francois Klinger, Jean-Claude Laurent, Robert Perron, Joel Schwartz, Francois Vachet
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Patent number: 5990347Abstract: A process for preparing a carboxylic acid having n+1 carbon atoms by contacting carbon monoxide with a liquid reaction composition comprising an alcohol of n carbon atoms or an ester derivative thereof; an iridium carbonylation catalyst and a hydrocarbyl halide promoter wherein in the liquid reaction composition the concentration of water is about 2 to 8% by weight, the concentration of ester derivative of said alcohol and product acid is from 1 to 60% by weight (preferably 3-35% by weight), and the concentration of hydrocarbyl halide is from 2 to 10% weight.Type: GrantFiled: April 28, 1995Date of Patent: November 23, 1999Assignee: BP Chemicals LimitedInventor: Kirsten Everald Clode
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Patent number: 5981796Abstract: A process is provided for manufacture of branched carboxylic acids from branched olefins by means of reaction with carbon monoxide and a solid acid catalyst. In this process, a branched olefin, or a precursor thereof, is reacted in continuously backmixed reactor, with continuously supplied carbon monoxide and water, while continuously an effluent is withdrawn comprising branched carboxylic acid, non-converted olefin, carbon monoxide and water, in the presence of an acidic ion exchanger, having sufficient acid groups to provide requisite protons for conversion of the olefin or a precursor of it, and carbon monoxide into branched carboxylic acids.Type: GrantFiled: February 25, 1998Date of Patent: November 9, 1999Assignee: Shell Oil CompanyInventors: Anthonius Johannes Maria Breed, Rene Johan Haan, Jean-Paul Lange, Leonardus Petrus
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Patent number: 5900504Abstract: Disclosed is an improved liquid phase process for the preparation of an acetyl product comprising acetic acid, by the carbonylation of a carbonylatable reactant material comprising methanol, methyl acetate, dimethyl ether or a mixture thereof in the presence of a catalyst system comprising a nickel component and an iodide component. In the separation of the crude acetyl product mixture from a liquid containing the non-volatile catalyst components, precipitation of metals and other catalyst components is avoided or minimized by maintaining a hydrogen pressure of at least 0.34 bar absolute within the flash evaporator zone wherein the separation occurs.Type: GrantFiled: February 20, 1996Date of Patent: May 4, 1999Assignee: Eastman Chemical CompanyInventors: Jeffrey Scott Kanel, Stanley John Okrasinski
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Patent number: 5900505Abstract: Disclosed is a process wherein a mixture of methanol or a methanol source, a halide and carbon monoxide are contacted in the vapor phase with a supported catalyst comprising iridium and at least one second metal selected from ruthenium, molybdenum, tungsten, palladium, platinum and rhenium deposited on a catalyst support material.Type: GrantFiled: January 22, 1998Date of Patent: May 4, 1999Assignee: Eastman Chemical CompanyInventors: Gerald Charles Tustin, Joseph Robert Zoeller, Horace Lawrence Browning, Jr., Andy Hugh Singleton
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Patent number: 5883289Abstract: A method for preparing carboxylic acids including (n+1) carbon atoms, or the related esters, by liquid phase carbonylation of an alcohol including (n) carbon atoms, in the presence of a uniform catalytic system based on at least one iridium compound and at least one halogenated promoter. In particular, the method is characterised in that the content of ester related to said carboxylic acid and alcohol is kept between 15 and 35% in the medium during the reaction, while the halogenated promoter content is kept between 10 and 20%, and the partial carbon monoxide pressure is 40-200 bar. Said method enables both the rate of carbonylation and the acetic acid selectivity to be increased.Type: GrantFiled: May 14, 1997Date of Patent: March 16, 1999Assignee: Acetex ChimieInventors: Philippe Denis, Dominique Nobel, Robert Perron, Joel Andre Schwartz
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Patent number: 5880311Abstract: Catalyst particles are contacted with a liquid and a gas in a vertically extending cylindrical vessel. The particles and liquid are placed in the vessel into which the gas and liquid are continuously fed from the bottom thereof so that an upwardly flowing mixture comprising the particles, liquid and gas is formed. The mixture is introduced into a gas separating zone disposed adjacent to an upper portion of the vessel to separate the mixture by gravity into a gas phase, a supernatant liquid phase and a phase rich in the catalyst particles. The gas and supernatant phases are continuously withdrawn from the separating zone while the catalyst particles-rich phase is continuously recycled to the bottom of the vessel by gravity.Type: GrantFiled: March 30, 1995Date of Patent: March 9, 1999Assignee: Tonen CorporationInventors: Fumihiko Uemura, Hideki Sugiyama, Chieko Nagasawa, Takeshi Minami, Kazuhiko Hamato, Noriyuki Yoneda, Akihisa Yamaguchi
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Patent number: 5874610Abstract: A process for the recovery of a carbonylation product from a liquid reaction composition of an iridium-catalysed carbonylation reaction of a carbonylatable reactant comprises subjecting the composition to a vaporization with or without the addition of heat to produce a vapor-fraction and a liquid fraction, the vapor fraction comprises carbonylation product and the liquid fraction has a water concentration of at least 0.5% by weight to stabilize the iridium catalyst.Type: GrantFiled: October 23, 1997Date of Patent: February 23, 1999Assignee: BP Chemicals LimitedInventors: Kirsten Everald Clode, Derrick John Watson, Carl Jozef Elsa Vercauteren
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Patent number: 5847204Abstract: An iridium-based solution is prepared by contacting components in a liquid phase containing (a) a carbonylated iridium compound, (b) hydriodic acid, a precursor of such an acid, or mixture thereof, and (c) a solvent; under a total pressure of between 1 and 10 bar at a temperature not greater than the boiling temperature of the solvent under conditions in which the components are brought into contact. The iridium-based solution can be used as a catalyst for carrying out carbonylation, hydroformylation or isomerization reactions.Type: GrantFiled: September 27, 1996Date of Patent: December 8, 1998Assignee: Acetex ChimieInventor: Dominique Nobel
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Patent number: 5834622Abstract: A process for the carbonylation of a carbonylatable reactant having a carbonylatable moiety having at least two carbon atoms and/or a reactive derivative thereof which process comprises contacting said carbonylatable reactant and/or a reactive derivative thereof with carbon monoxide in a liquid reaction composition in a carbonylation reactor characterized in that the liquid reaction composition comprises: (a) an iridium catalyst, (b) a halide, (c) at least a finite concentration of water, (d) a carbonylatable reactant having a carbonylatable moiety having at least two carbon atoms and/or a reactive derivative thereof and (e) as promoter, at least one of ruthenium and osmium.Type: GrantFiled: July 5, 1996Date of Patent: November 10, 1998Assignee: BP Chemicals LimitedInventor: John Glenn Sunley
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Patent number: 5817869Abstract: Methanol is converted to acetic acid by reaction with carbon monoxide in the presence of an carbonylation system which comprises a rhodium catalyst component and a liquid reaction medium containing acetic acid, methyl iodide, methyl acetate, and at least one pentavalent Group VA oxide and water in specific concentrations. The present carbonylation system not only increases the yields and reaction rates but also serves to stabilize the rhodium catalyst component in an active form.Type: GrantFiled: October 3, 1996Date of Patent: October 6, 1998Assignee: Quantum Chemical CorporationInventors: James A. Hinnenkamp, Noel Hallinan
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Patent number: 5814193Abstract: A process for the purification of a C.sub.2 to C.sub.4 carboxylic acid and/or an anhydride thereof having halide impurities, which process comprises the steps of (a) exposing the impure acid and/or anhydride to electromagnetic radiation under conditions of intensity, wavelength and temperature, and for a time, sufficient to convert at least a portion of the halide impurities to lower--and/or higher-boiling halide components and (b) separating the lower--and/or higher-boiling halide components formed in step (a) from the C.sub.2 to C.sub.4 carboxylic acid and/or anhydride. Also, a process for the purification of a C.sub.2 to C.sub.Type: GrantFiled: August 9, 1996Date of Patent: September 29, 1998Assignee: BP Chemicals LimitedInventor: Barry Crowe
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Patent number: 5773642Abstract: Preparation of carboxylic acids or corresponding esters by reacting an alcohol with carbon monoxide in the presence of an iridium catalyst and a halogen promoter. The reaction involves a reaction mixture composed of more than 0% to 10% water, more than 0% to 10% halogen promoter, 2% to 40% of an ester corresponding to the reaction of alcohol with the acid, soluble iodides in an amount such that the atomic ratio of iodides to iridium varies between more than 0 and 10, the carboxylic acid being used as the reaction solvent.Type: GrantFiled: May 14, 1997Date of Patent: June 30, 1998Assignee: Acetex ChimieInventors: Philippe Denis, Dominique Nobel, Robert Perron, Philippe Perrona, Joel Schwartz
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Patent number: 5763654Abstract: A process for the production of acetic acid which comprises reacting carbon monoxide with a carbonylatable reactant comprising greater than 10%, typically from 30 to 100%, by weight dimethyl ether introduced to a reactor in which there is maintained at elevated temperature a liquid reaction composition comprising a Group VIII noble metal catalyst, for example rhodium or iridium, methyl iodide promoter, an optional co-promoter and water at a concentration in the liquid reaction composition of from 1.0 to 10% by weight.Type: GrantFiled: October 15, 1996Date of Patent: June 9, 1998Assignee: BP Chemicals LimitedInventors: Michael David Jones, Andrew David Poole
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Patent number: 5760279Abstract: The use of manganese at a molar ratio of manganese:rhodium of (0.2 to 20):1 to stabilize the rhodium catalyst during the rhodium catalyzed carbonylation of alkyl alcohols and/or recovery of carbonylation product therefrom at low partial pressure of carbon monoxide of less than or equal to 7 bar.Type: GrantFiled: June 12, 1996Date of Patent: June 2, 1998Assignee: BP Chemicals LimitedInventor: Andrew David Poole
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Patent number: 5723660Abstract: The present invention provides a process for producing acetic acid by reacting continuously methanol, methyl acetate and the like with carbon monoxide in the presence of an eighth group metal-containing catalyst, methyl iodide and water, which is characterized in that wherein a liquid separation state in a decanter at the top of the first distillation column is maintained by adding water to the first distillation column. High quality acetic acid which has not so far been achieved can be obtained while controlling the purifying energy in a low level.Type: GrantFiled: December 13, 1996Date of Patent: March 3, 1998Assignee: Daicel Chemical Industries, Ltd.Inventors: Yoshiaki Morimoto, Hiroyuki Nakayama, Takashi Ueno
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Patent number: 5710325Abstract: This invention provides a process for the preparation of adipic acid from pentenoic acids or esters of pentenoic acids by hydrocarboxylation of a reaction mixture in which gamma-valerolactone constitutes 30 to 70% by weight of the reaction mixture.Type: GrantFiled: November 1, 1996Date of Patent: January 20, 1998Assignees: E. I. Du Pont de Nemours and Company, DSM, N.V.Inventors: Harold Stanley Bruner, Jr., Samuel Livingston Lane, Bruce Edwin Murphree
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Patent number: 5650537Abstract: A process for the preparation of N-acylglycine derivatives of the formula (I) ##STR1## which comprises reacting a carboxylic acid amide with an aldehyde in the presence of a solvent and an acid to give an acylaminomethylol and then carbonylating the acylaminomethylol in the presence of a cobalt carbonyl catalyst.Type: GrantFiled: May 2, 1995Date of Patent: July 22, 1997Assignee: Hoechst AGInventors: Matthias Beller, Hartmut Fischer, Thomas Gerdau, Peter Gross
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Patent number: 5648531Abstract: A process for continuously producing acetic anhydride alone or acetic anhydride and acetic acid by reacting methyl acetate and/or dimethyl ether and, optionally, water and/or methanol, with carbon monoxide alone or carbon monoxide and hydrogen in the presence of a rhodium compound and methyl iodide as principal catalysts. Trace impurities causative of tar formation are distilled and separated in an evaporator and/or a subsequent refining step to remove the same. The removal of the trace impurities causative of tar formation serves to decrease the amount of tar formed as an impurity.Type: GrantFiled: March 22, 1995Date of Patent: July 15, 1997Assignee: Daicel Chemical Industries, Ltd.Inventors: Yoshiaki Morimoto, Hiroto Tanigawa, Kazuyuki Akita
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Patent number: 5648527Abstract: New saturated fluoroalkylamines and carboxyalkylbetaines and alkylsulfobetaines derived therefrom, and mixtures containing the new fluoroalkylamines and mixtures containing the new fluorobetaines are described. The saturated fluoroalkylamines conform to the formula below ##STR1## in which n is an integer from 3 to 17 and R.sup.1 and R.sup.2 are C.sub.1 to C.sub.4 -alkyl, C.sub.1 to C.sub.4 -hydroxyalkyl or hydrogen, with the proviso that only one of the two substituents R.sup.1 and R.sup.2 is hydrogen. The carboxyalkylbetaines and sulfobetaines and the mixtures thereof are highly effective products for reducing the surface tension of water/air systems and the interfacial tension of water/hydrocarbon systems.Type: GrantFiled: June 7, 1995Date of Patent: July 15, 1997Assignee: Hoechst AktiengesellschaftInventors: Gunter Prossel, Wolfgang Knaup, Frank Wehowsky
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Patent number: 5625094Abstract: Process for the preparation of a carboxylic acid or ester thereof. The process includes reacting at least one alcohol, alkyl or aryl halide, ether or ester, with carbon monoxide, in the presence of a catalytically effective amount of at least one rhodium compound or rhodium metal, at least one iridium compound or iridium metal, or at least one mixed rhodium/iridium compound, and at least one halogen-containing promoter therefor.Type: GrantFiled: May 26, 1995Date of Patent: April 29, 1997Assignee: Rhone-Poulenc ChimieInventors: Dominique Nobel, Robert Perron, Philippe Denis
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Patent number: 5504246Abstract: A process for preparing carboxylates of polyoxyalkylene siloxanes and -amines, alkylpolyoxyalkylenes, polyoxyalkylene block polymers, alkylamidepolyoxyalkylenes and alkylpolyglucosides comprising subjecting a primary hydroxyl group-containing polyoxyalkylene compound or alkylpolyglucoside to mild oxidiation. The invention also relates to the novel polyoxyalkylene amine and alkylamidepolyoxyalkylene carboxylates prepared by the process.Type: GrantFiled: June 30, 1994Date of Patent: April 2, 1996Assignee: Sandoz Ltd.Inventors: Parfait J. Likibi, Robert V. Casciani, Gregory L. McCraw
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Patent number: 5486528Abstract: Novel basic ether of general formula (I), ##STR1## wherein R.sup.1 and R.sup.2 are independently hydrogen, halogen or C.sub.1-4 alkoxy, or together they represent a 3,4-methylenedioxy group,R stands for C.sub.1-8 alkyl,R.sup.3 represents hydrogen, C.sub.1-4 alkyl or hydroxy,A is a valency bond or methylene group,R.sup.4 and R.sup.5 are independently hydrogen, C.sub.1-12 alkyl or C.sub.1-12 alkenyl, orR.sup.4 and R.sup.5 form together with the adjacent nitrogen atom 1-pyrrolidinyl, 1-piperidinyl, morpholino or 1-piperazinyl groups, stereo and optically active isomers and their possible mixtures, acid-addition salts and quaternary ammonium derivatives thereof. The basic ethers have antiulceric and anxiolytic activities.Type: GrantFiled: April 11, 1994Date of Patent: January 23, 1996Assignee: Egis Gyogyszergyar Rt.Inventors: Judit Bajnogel, Gabor Blasko, Zoltan Budai, Eva Schmidt, Andras Egyed, Marton Fekete, Istvan Gacsalyi, Istvan Gyertyan, Tibor Mezei, Kalara Reiter nee Esses, Gyula Simig, Katalin Szemeredi, Enik Szirt nee Kiszelly
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Patent number: 5463137Abstract: A propylene stream which contains propane as an impurity is contacted with carbon monoxide and hydrogen in the presence of a hydroformylation catalyst thereby producing a product stream containing butyraldehyde and/or n-butyl alcohol, unreacted propylene and propane. A gas mixture containing propylene and propane is separated from the product stream and subjected to adsorption at a temperature of 0.degree. to 250.degree. C. in a bed of adsorbent which selectively adsorbs propylene, thereby adsorbing substantially all of the propylene from the gas mixture. The propylene is desorbed from the adsorbent and recycled to the reaction zone. The process is operated on a low per pass conversion with recycle of unreacted propylene. In the system of the invention the propylene adsorption unit may be upstream or downstream of the hydroformylation reactor.Type: GrantFiled: April 22, 1994Date of Patent: October 31, 1995Assignee: The BOC Group, Inc.Inventors: Ramakrishnan Ramachandran, Loc H. Dao
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Patent number: 5436356Abstract: A process for the carbonylation of ethylenically unsaturated compounds by reaction with carbon monoxide and a co-reactant in the presence of a substantially non-acidic catalyst system based on a palladium compound and a bidentate ligand of the formulaR.sub.1 R.sub.2 M.sub.1 RM.sub.2 R.sub.3 R.sub.4in which M.sub.1 and M.sub.2 may be phosphorus, arsenic or antimony atom, R is a bivalent organic bridging group, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently substituted or non-substituted aliphatic groups, with the proviso that R.sub.1 together with R.sub.2, and/or R.sub.3 together with R.sub.4 form a bivalent cyclic group with at least 5 ring atoms whereby the two free valencies are linked to M.sub.1 or M.sub.2, respectively.Catalytic compositions employing the bidentate ligands used in this method in which M.sub.1 and M.sub.2 are phosphorous are also presented.Type: GrantFiled: January 14, 1994Date of Patent: July 25, 1995Assignee: Shell Oil CompanyInventors: Eit Drent, Dennis H. L. Pello, Melis Hasselaar
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Patent number: 5420345Abstract: Preparation of an aliphatic carboxylic acid having (n+1) carbon atoms, where n is an integer up to 6, may be achieved by contacting an aliphatic alcohol having n carbon atoms or a reactive derivative thereof with carbon monoxide, in the presence of a copper, nickel, iridium, rhodium or cobalt loaded mordenite zeolite catalyst, at elevated temperature and at a pressure in the range 15 to 200 bars.Type: GrantFiled: October 26, 1993Date of Patent: May 30, 1995Assignee: BP Chemicals LimitedInventor: Warren J. Smith