Preparation By Carbonylation Patents (Class 562/517)
  • Patent number: 6465680
    Abstract: 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: Grant
    Filed: June 20, 2001
    Date of Patent: October 15, 2002
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Byeong No Lee, In-Sun Jung, Eun Joo Jang
  • Publication number: 20020137660
    Abstract: The present invention relates to a process for the preparation of alkylcarboxylic allyl esters by reacting allyl alcohol and alkylcarboxylic acids.
    Type: Application
    Filed: March 18, 2002
    Publication date: September 26, 2002
    Inventors: Walter Kuhn, Gerhard Senft
  • Patent number: 6452043
    Abstract: 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: Grant
    Filed: April 5, 2000
    Date of Patent: September 17, 2002
    Assignee: Eastman Chemical Company
    Inventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
  • Patent number: 6420304
    Abstract: 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: Grant
    Filed: April 20, 2000
    Date of Patent: July 16, 2002
    Assignee: China Petrochemical Development Corporation
    Inventors: Chia-Jung Tsai, Yao-Lung Liu, Hsi-Chin Tsai
  • Patent number: 6395927
    Abstract: 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: Grant
    Filed: September 23, 1998
    Date of Patent: May 28, 2002
    Assignee: Acetex Chimie
    Inventors: Carl Patois, Robert Perron, Daniel Thiebaut
  • Publication number: 20020058834
    Abstract: 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: Application
    Filed: June 1, 2001
    Publication date: May 16, 2002
    Inventor: Thaddeus S. Franczyk
  • Patent number: 6362366
    Abstract: 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: Grant
    Filed: July 6, 2000
    Date of Patent: March 26, 2002
    Assignee: Millennium Petrochemicals Inc
    Inventors: Noel Hallinan, James A. Hinnenkamp
  • Patent number: 6355595
    Abstract: 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: Grant
    Filed: August 25, 1999
    Date of Patent: March 12, 2002
    Assignee: Eastman Chemical Company
    Inventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
  • Patent number: 6355837
    Abstract: 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: Grant
    Filed: August 25, 1999
    Date of Patent: March 12, 2002
    Assignee: Eastman Chemical Company
    Inventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
  • Patent number: 6353132
    Abstract: 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: Grant
    Filed: August 25, 1999
    Date of Patent: March 5, 2002
    Assignee: Eastman Chemical Company
    Inventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
  • Patent number: 6323364
    Abstract: 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: Grant
    Filed: August 31, 1999
    Date of Patent: November 27, 2001
    Assignee: Celanese International Corporation
    Inventors: Pramod Agrawal, Hung-Cheun Cheung, Darrell A. Fisher, Valerie Santillan, Mark O. Scates, Elaine C. Sibrel, G. Paul Torrence
  • Publication number: 20010043895
    Abstract: 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: Application
    Filed: May 11, 2001
    Publication date: November 22, 2001
    Applicant: Haldor Topsoe A/S
    Inventor: Niels C. Schiodt
  • Patent number: 6303813
    Abstract: 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: Grant
    Filed: August 31, 1999
    Date of Patent: October 16, 2001
    Assignee: Celanese International Corporation
    Inventors: Mark O. Scates, Valerie Santillan, Pramod Agrawal, G. Paull Torrence, R. Jay Warner
  • Patent number: 6268530
    Abstract: 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: Grant
    Filed: January 5, 1998
    Date of Patent: July 31, 2001
    Assignees: DSM N.V., E. I. DuPont de Nemours and Company
    Inventors: Imre Toth, Onko Gelling, Rudolf P. M. Guit, Antonius J. F. Simons, Simon Hans H. Niemann
  • Publication number: 20010007912
    Abstract: 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: Application
    Filed: December 26, 2000
    Publication date: July 12, 2001
    Inventors: Robert Edward Allan, Derrick John Watson
  • Patent number: 6160163
    Abstract: 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: Grant
    Filed: February 16, 1999
    Date of Patent: December 12, 2000
    Assignee: Eastman Chemical Company
    Inventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
  • Patent number: 6153792
    Abstract: 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: Grant
    Filed: December 18, 1998
    Date of Patent: November 28, 2000
    Assignee: UOP LLC
    Inventors: William A. Leet, Santi Kulprathipanja
  • Patent number: 6130355
    Abstract: 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: Grant
    Filed: December 24, 1998
    Date of Patent: October 10, 2000
    Assignee: BP Chemicals Limited
    Inventor: Michael David Jones
  • Patent number: 6114576
    Abstract: 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: Grant
    Filed: December 18, 1998
    Date of Patent: September 5, 2000
    Assignee: UOP LLC
    Inventors: William A. Leet, Santi Kulprathipanja, Bruce A. Briggs
  • Patent number: 6103934
    Abstract: 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: Grant
    Filed: December 18, 1998
    Date of Patent: August 15, 2000
    Assignee: Millennium Petrochemicals, Inc.
    Inventors: Noel Hallinan, James A. Hinnenkamp
  • Patent number: 6090986
    Abstract: 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: Grant
    Filed: October 27, 1997
    Date of Patent: July 18, 2000
    Assignee: 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
  • Patent number: 6084124
    Abstract: 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: Grant
    Filed: February 4, 1999
    Date of Patent: July 4, 2000
    Assignee: Shell Oil Company
    Inventors: Lynn Henry Slaugh, Thomas Clayton Forschner
  • Patent number: 6066762
    Abstract: 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: Grant
    Filed: December 23, 1997
    Date of Patent: May 23, 2000
    Assignee: Chiyoda Corporation
    Inventors: Noriyuki Yoneda, Takeshi Minami, Yoshihiro Nakagawa, Ikuo Ohta, Akihisa Yamaguchi, Hideki Sugiyama, Fumihiko Uemura
  • Patent number: 6013816
    Abstract: 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: Grant
    Filed: July 5, 1996
    Date of Patent: January 11, 2000
    Assignee: DSM NV
    Inventors: Onko J. Gelling, Imre Toth
  • Patent number: 6008408
    Abstract: 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: Grant
    Filed: July 11, 1995
    Date of Patent: December 28, 1999
    Assignee: Rhone-Poulenc Chimie
    Inventors: Philippe Denis, Francois Klinger, Jean-Claude Laurent, Robert Perron, Joel Schwartz, Francois Vachet
  • Patent number: 5990347
    Abstract: 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: Grant
    Filed: April 28, 1995
    Date of Patent: November 23, 1999
    Assignee: BP Chemicals Limited
    Inventor: Kirsten Everald Clode
  • Patent number: 5981796
    Abstract: 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: Grant
    Filed: February 25, 1998
    Date of Patent: November 9, 1999
    Assignee: Shell Oil Company
    Inventors: Anthonius Johannes Maria Breed, Rene Johan Haan, Jean-Paul Lange, Leonardus Petrus
  • Patent number: 5900504
    Abstract: 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: Grant
    Filed: February 20, 1996
    Date of Patent: May 4, 1999
    Assignee: Eastman Chemical Company
    Inventors: Jeffrey Scott Kanel, Stanley John Okrasinski
  • Patent number: 5900505
    Abstract: 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: Grant
    Filed: January 22, 1998
    Date of Patent: May 4, 1999
    Assignee: Eastman Chemical Company
    Inventors: Gerald Charles Tustin, Joseph Robert Zoeller, Horace Lawrence Browning, Jr., Andy Hugh Singleton
  • Patent number: 5883289
    Abstract: 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: Grant
    Filed: May 14, 1997
    Date of Patent: March 16, 1999
    Assignee: Acetex Chimie
    Inventors: Philippe Denis, Dominique Nobel, Robert Perron, Joel Andre Schwartz
  • Patent number: 5880311
    Abstract: 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: Grant
    Filed: March 30, 1995
    Date of Patent: March 9, 1999
    Assignee: Tonen Corporation
    Inventors: Fumihiko Uemura, Hideki Sugiyama, Chieko Nagasawa, Takeshi Minami, Kazuhiko Hamato, Noriyuki Yoneda, Akihisa Yamaguchi
  • Patent number: 5874610
    Abstract: 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: Grant
    Filed: October 23, 1997
    Date of Patent: February 23, 1999
    Assignee: BP Chemicals Limited
    Inventors: Kirsten Everald Clode, Derrick John Watson, Carl Jozef Elsa Vercauteren
  • Patent number: 5847204
    Abstract: 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: Grant
    Filed: September 27, 1996
    Date of Patent: December 8, 1998
    Assignee: Acetex Chimie
    Inventor: Dominique Nobel
  • Patent number: 5834622
    Abstract: 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: Grant
    Filed: July 5, 1996
    Date of Patent: November 10, 1998
    Assignee: BP Chemicals Limited
    Inventor: John Glenn Sunley
  • Patent number: 5817869
    Abstract: 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: Grant
    Filed: October 3, 1996
    Date of Patent: October 6, 1998
    Assignee: Quantum Chemical Corporation
    Inventors: James A. Hinnenkamp, Noel Hallinan
  • Patent number: 5814193
    Abstract: 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: Grant
    Filed: August 9, 1996
    Date of Patent: September 29, 1998
    Assignee: BP Chemicals Limited
    Inventor: Barry Crowe
  • Patent number: 5773642
    Abstract: 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: Grant
    Filed: May 14, 1997
    Date of Patent: June 30, 1998
    Assignee: Acetex Chimie
    Inventors: Philippe Denis, Dominique Nobel, Robert Perron, Philippe Perrona, Joel Schwartz
  • Patent number: 5763654
    Abstract: 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: Grant
    Filed: October 15, 1996
    Date of Patent: June 9, 1998
    Assignee: BP Chemicals Limited
    Inventors: Michael David Jones, Andrew David Poole
  • Patent number: 5760279
    Abstract: 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: Grant
    Filed: June 12, 1996
    Date of Patent: June 2, 1998
    Assignee: BP Chemicals Limited
    Inventor: Andrew David Poole
  • Patent number: 5723660
    Abstract: 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: Grant
    Filed: December 13, 1996
    Date of Patent: March 3, 1998
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yoshiaki Morimoto, Hiroyuki Nakayama, Takashi Ueno
  • Patent number: 5710325
    Abstract: 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: Grant
    Filed: November 1, 1996
    Date of Patent: January 20, 1998
    Assignees: E. I. Du Pont de Nemours and Company, DSM, N.V.
    Inventors: Harold Stanley Bruner, Jr., Samuel Livingston Lane, Bruce Edwin Murphree
  • Patent number: 5650537
    Abstract: 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: Grant
    Filed: May 2, 1995
    Date of Patent: July 22, 1997
    Assignee: Hoechst AG
    Inventors: Matthias Beller, Hartmut Fischer, Thomas Gerdau, Peter Gross
  • Patent number: 5648531
    Abstract: 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: Grant
    Filed: March 22, 1995
    Date of Patent: July 15, 1997
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yoshiaki Morimoto, Hiroto Tanigawa, Kazuyuki Akita
  • Patent number: 5648527
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: July 15, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunter Prossel, Wolfgang Knaup, Frank Wehowsky
  • Patent number: 5625094
    Abstract: 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: Grant
    Filed: May 26, 1995
    Date of Patent: April 29, 1997
    Assignee: Rhone-Poulenc Chimie
    Inventors: Dominique Nobel, Robert Perron, Philippe Denis
  • Patent number: 5504246
    Abstract: 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: Grant
    Filed: June 30, 1994
    Date of Patent: April 2, 1996
    Assignee: Sandoz Ltd.
    Inventors: Parfait J. Likibi, Robert V. Casciani, Gregory L. McCraw
  • Patent number: 5486528
    Abstract: 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: Grant
    Filed: April 11, 1994
    Date of Patent: January 23, 1996
    Assignee: 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
  • Patent number: 5463137
    Abstract: 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: Grant
    Filed: April 22, 1994
    Date of Patent: October 31, 1995
    Assignee: The BOC Group, Inc.
    Inventors: Ramakrishnan Ramachandran, Loc H. Dao
  • Patent number: 5436356
    Abstract: 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: Grant
    Filed: January 14, 1994
    Date of Patent: July 25, 1995
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Dennis H. L. Pello, Melis Hasselaar
  • Patent number: 5420345
    Abstract: 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: Grant
    Filed: October 26, 1993
    Date of Patent: May 30, 1995
    Assignee: BP Chemicals Limited
    Inventor: Warren J. Smith