Of Halogenated Hydrocarbon Patents (Class 562/520)
-
Patent number: 11179712Abstract: The present invention relates to a method for preparing a sulfated metal oxide catalyst for chlorination, and a method for producing a reaction product containing methyl chloride (CH3Cl) by using the sulfated metal oxide catalyst. A sulfated zirconia catalyst and a sulfated tin oxide catalyst are disclosed as the sulfated metal oxide catalyst for chlorination.Type: GrantFiled: August 30, 2018Date of Patent: November 23, 2021Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGYInventors: Ho Jeong Chae, Young Min Kim, Jip Kim, Hyung Ju Kim
-
Publication number: 20150025269Abstract: The invention provides a simple, efficient, environmental friendly catalytic system for the direct carboxylation reaction using CO2 under mild condition. A single step heterogeneous catalytic process for preparation of alkynyl carboxylic acids of formula I is disclosed.Type: ApplicationFiled: January 25, 2013Publication date: January 22, 2015Inventors: Ravindra Dattatray Aher, Madhuri Hanumant Gage, Reddy Santhosh Rekula, Pratibha Uttam Karabal, Gurunath Mallappa Suryavanshi, Arumugam Sudalai
-
Patent number: 8198476Abstract: 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: GrantFiled: May 23, 2008Date of Patent: June 12, 2012Assignee: BP Chemicals LimitedInventors: Emma Louise Carrington-Smith, David John Law, Paul Gerard Pringle, John Glenn Sunley
-
Publication number: 20110201841Abstract: Oxidatively halogenate methane by placing a feedstream that comprises methane, a source of halogen, a source of oxygen and, optionally, a source of diluent gas in contact with a first catalyst (e.g. a solid super acid or a solid super base) that has greater selectivity to methyl halide and carbon monoxide than to methylene halide, trihalomethane or carbon tetrahalide. Improve overall selectivity to methyl halide by using a second catalyst that converts at least part of the feedstream to a mixture of methyl halide, methylene halide, trihalomethane, carbon tetrahalide and unreacted oxygen, and placing that mixture in contact with the first catalyst which converts at least a portion of the methylene halide, trihalomethane and carbon tetrahalide to carbon monoxide, hydrogen halide and water.Type: ApplicationFiled: August 19, 2009Publication date: August 18, 2011Inventors: Robert G. Bowman, Eric E. Stangland, Mark E. Jones, Dean M. Millar, Simon G. Podkolzin, Brien A. Stears, Richard M. Wehmeyer
-
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
-
Patent number: 7741512Abstract: Process for preparing an aliphatic carboxylic acid having (n+1) carbon atoms, where n is an integer up to 6, and/or the ester derivative thereof by contacting an aliphatic alcohol having n carbon atoms and/or a reactive derivative thereof selected from dialkyl ether, ester of the alcohol and an alkyl halide with carbon monoxide in the presence of a catalyst. The catalyst consists of mordenite which has been ion- exchanged or otherwise loaded with silver.Type: GrantFiled: March 27, 2007Date of Patent: June 22, 2010Assignee: BP Chemicals LimitedInventors: Harry Kaiser, David John Law, Stephan Andreas Schunk, John Glenn Sunley
-
Patent number: 7053241Abstract: Processes for the production of acetic acid by carbonylation of methanol, and reactive derivatives thereof, in a reaction mixture using a rhodium-based catalyst system with at least one metal salt catalyst stabilizer selected from the group of ruthenium salts, tin salts, and mixtures thereof are provided. The metal salt stabilizers minimize precipitation of the rhodium metal during recovery of the acetic acid product, particularly in flasher units in an acetic acid recovery scheme. Stability of the rhodium metal is achieved even when the acetic acid is produced in low water content reaction mixtures in the presence of an iodide salt co-promoter at a concentration that generated an iodide ion concentration of greater than about 3 wt. % of the reaction mixture. The stabilizing metal salts may be present in the reaction mixtures for the production of acetic acid at molar concentrations of metal to rhodium of about 0.1:1 to about 20:1.Type: GrantFiled: February 24, 2005Date of Patent: May 30, 2006Assignee: Celanese International CorporationInventor: G. Paull Torrence
-
Patent number: 6849763Abstract: The present invention relates to a new process for the synthesis of racemic and optically active bicalutamide starting from ethyl pyruvate and methyl methacrylate. The present invention discloses processes of preparing bicalutamide intermediates including ethyl-[2-{4-fluorophenyl sulfone)]-2-hydroxy propionate, 1,2-epoxy-2-methyl propionate and 2-hydrox-2-methyl-3-(4-fluorophenylthio) propionic acid. The present invention further discloses micronized rac-bicalutamide and the preparation thereof.Type: GrantFiled: March 8, 2004Date of Patent: February 1, 2005Assignee: Biogal Gyógyszergyár Rt.Inventors: Ben-Zion Dolitzky, Ofer Reany, Jenny Shammai
-
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
-
Patent number: 6613938Abstract: A vapor-phase carbonylation method for producing esters and carboxylic acids from reactants comprising lower alkyl alcohols, lower alkyl alcohol generating compositions 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 platinum and tin associated with a solid carrier material.Type: GrantFiled: June 19, 2001Date of Patent: September 2, 2003Assignee: Eastman Chemical CompanyInventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
-
Patent number: 6515172Abstract: Process for the preparation of perfluorocarboxylic acids of the formula RF—COOH, salts thereof and esters thereof from perfluoroalkyl iodides of the formula RF′—I, in which RF and RF′ are cyclic, branched or linear, saturated or unsaturated perfluoroalkyl radicals, by activating the perfluoroalkyl iodides in the presence of oxygen and in organic solvents.Type: GrantFiled: July 10, 2001Date of Patent: February 4, 2003Assignee: Clariant GmbHInventors: Ralf Grottenmüller, Wolfgang Knaup, Anton Probst, Klaus Dullinger
-
Publication number: 20030018212Abstract: A vapor-phase carbonylation method for producing esters and carboxylic acids from reactants comprising lower alkyl alcohols, lower alkyl alcohol generating compositions 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 platinum and tin associated with a solid carrier material.Type: ApplicationFiled: June 19, 2001Publication date: January 23, 2003Inventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
-
Patent number: 6452058Abstract: An oxidative halogenation process involving contacting a reactant hydrocarbon selected from methane, a halogenated C1 hydrocarbon, or a mixture thereof with a source of halogen and, preferably, a source of oxygen in the presence of a rare earth halide or rare earth oxyhalide catalyst, so as to form a halogenated C1 hydrocarbon having a greater number of halogen substituents as compared with the reactant hydrocarbon. Preferably, the product is a monohalogenated methane, more preferably, methyl chloride. The oxidative halogenation process to form methyl halide can be integrated with downstream processes to produce valuable commodity chemicals, for example, methyl alcohol and/or dimethyl ether; light olefins, including ethylene, propylene, and butenes; higher hydrocarbons, including gasolines; vinyl halide monomer, and acetic acid. Hydrogen halide, which is a co-product of these downstream processes, can be recycled to the oxidative halogenation process.Type: GrantFiled: May 21, 2001Date of Patent: September 17, 2002Assignee: Dow Global Technologies Inc.Inventors: Albert E. Schweizer, Mark E. Jones, Daniel A. Hickman
-
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
-
Patent number: 6140535Abstract: A process as provided for producing an acetic acid process stream having less than 400 ppm propionic acid and less than 1500 ppm water. Methanol or a reactive derivative thereof and carbon monoxide is fed to a carbonylation reactor in which there is maintained during the course of the process a liquid reaction composition containing an iridium carbonylation catalyst, methyl iodide co-catalyst, a promoter, water at a concentration of less than about 8% by weight, methyl acetate, acetic acid, and propionic acid by-product and its precursors. Liquid reaction composition is withdrawn from the carbonylation reactor and introduced to a flash zone to form a vapor fraction comprising water, acetic acid product, propionic acid by-product, methyl acetate, methyl iodide and propionic acid precursors, and a liquid fraction comprising involatile iridium catalyst, involatile optional promoter or promoters, acetic acid and water.Type: GrantFiled: December 17, 1997Date of Patent: October 31, 2000Assignee: BP Chemicals LimitedInventor: Bruce L Williams
-
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
-
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
-
Patent number: 5932764Abstract: A process for the production of a carboxylic acid having n+1 carbon atoms comprises (a) carbonylating with carbon monoxide in a first reaction zone at elevated temperature and pressure an alkyl alcohol having n carbon atoms and/or a reactive derivative thereof to produce a carboxylic acid having n+1 carbon atoms in a liquid reaction composition comprising carboxylic acid product, an iridium catalyst, an alkyl halide co-catalyst, water, an ester of the carboxylic acid product and the alkyl alcohol, and optionally one or more promoters, (b) withdrawing from the first reaction zone at least a portion of the liquid reaction composition together with dissolved and/or entrained carbon monoxide, and passing at least a portion of the withdrawn liquid reaction composition and carbon monoxide to a second reaction zone, ((c)reacting at least 1% of the dissolved and/or entrained carbon monoxide in the withdrawn reaction composition by further carbonylation at elevated temperature and pressure in the second reaction zoneType: GrantFiled: December 4, 1997Date of Patent: August 3, 1999Assignee: BP Chemicals LimitedInventors: George Ernest Morris, John Glenn Sunley
-
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
-
Patent number: 5883295Abstract: A process for the production of acetic acid comprising carbonylating with carbon monoxide methanol and/or a reactive derivative thereof in the substantial absence of a metal promoter and/or ionic iodide co-promoter in a carbonylation reactor containing a liquid reaction composition comprising an iridium carbonylation catalyst, methyl iodide co-catalyst, water, acetic acid and methyl acetate wherein there is maintained (i) in the liquid reaction composition:(a) water at a concentration of less than 5.0% by weight and(b) methyl iodide at a concentration greater than 12% by weight and (ii) in the carbonylation reactor a total pressure of less than 50 barg.Type: GrantFiled: December 17, 1997Date of Patent: March 16, 1999Assignee: BP Chemicals LimitedInventors: John G. Sunley, Robert J Watt
-
Patent number: 5877347Abstract: A process for the production of acetic acid comprises (1) continuously feeding methanol and/or a reactive derivative thereof and carbon monoxide to a carbonylation reactor containing a liquid reaction composition comprising an iridium carbonylation catalyst, methyl iodide co-catalyst, a finite concentration of water, acetic acid, methyl acetate and, optionally at least one promoter, (2) carbonylating the methanol and/or reactive derivative thereof with the carbon monoxide in the liquid reaction composition to produce acetic acid; and (3) recovering acetic acid from the liquid reaction composition, there being continuously maintained (a) in the liquid reaction composition water at a concentration of no greater than 4.5% by weight, and (b) in the reactor a carbon monoxide partial pressure in the range from greater than 0 to 7.5 bar.Type: GrantFiled: December 17, 1997Date of Patent: March 2, 1999Assignee: BP Chemicals LimitedInventors: Evert Jan Ditzel, John Glenn Sunley, Robert John Watt
-
Patent number: 5877348Abstract: A process for the production of acetic acid by carbonylating with carbon monoxide methanol and/or a reactive derivative thereof in a carbonylation reactor containing a liquid reaction composition comprising an iridium carbonylation catalyst, methyl iodide co-catalyst, a finite concentration of water, acetic acid, methyl acetate and at least one promoter wherein the water concentration is at or below that at which the maximum in the graph of carbonylation rate versus water concentration occurs and there is employed in the liquid reaction composition a co-promoter selected from alkali metal iodides, alkaline earth metal iodides, metal complexes capable of generating I.sup.-, salts capable of generating I.sup.-, and mixtures of two or more thereof.Type: GrantFiled: December 17, 1997Date of Patent: March 2, 1999Assignee: BP Chemicals LimitedInventors: Evert Jan Ditzel, John Glenn Sunley, Robert John Watt
-
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
-
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
-
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
-
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
-
Patent number: 5808143Abstract: Catalysts of the formula I?A.sub.a B.sub.b O.sub.x !.sub.p ?C.sub.c D.sub.d Fe.sub.e Co.sub.f E.sub.i F.sub.j O.sub.y !.sub.q I,whereA is bismuth, tellurium, antimony, tin and/or copper,B is molybdenum and/or tungsten,C is an alkali metal, thallium and/or samarium,D is an alkaline earth metal, nickel, copper, cobalt, manganese, zinc, tin, cerium, chromium, cadmium, molybdenum, bismuth and/or mercury,E is phosphorus, arsenic, boron and/or antimony,F is a rare-earth metal, vanadium and/or uranium,a is from 0.01 to 8,b is from 0.1 to 30,c is from 0 to 4,d is from 0 to 20,e is from 0 to 20,f is from 0 to 20,i is from 0 to 6,j is from 0 to 15,x and y are numbers determined by the valency and frequency of the elements other than oxygen in I, and p and q are numbers whose ratio p/q is in the range from 0.001 to 0.Type: GrantFiled: March 22, 1996Date of Patent: September 15, 1998Assignee: BASF AktiengesellschaftInventors: Lothar Karrer, Hans-Peter Neumann, Hans-Dieter Eichhorn, Robin Stuart Jarret
-
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
-
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
-
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
-
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
-
Patent number: 5416237Abstract: In a process for the production of acetic acid by carbonylation of methanol in the presence of a rhodium carbonylation catalyst, methyl iodide and an iodide salt stabiliser the improvement resides in maintaining a finite concentration of water of up to about 10% by weight and a methyl acetate concentration of at least 2% by weight in the liquid reaction composition and recovering the acetic acid product by passing the liquid reaction composition through a flash zone to produce a vapour fraction which is passed to a single distillation column from which an acetic acid product is removed.Type: GrantFiled: July 18, 1994Date of Patent: May 16, 1995Assignee: BP Chemicals LimitedInventors: Simon D. Aubigne, Jeremy B. Cooper, Bruce L. Williams, Derrick J. Watson
-
Patent number: 5312969Abstract: Difunctional butenes are linearly dicarbonylated into 3-hexene-1,6-dioic acid or alkyl diesters thereof, well suited for the ultimate production of, e.g., adipic acid, by reacting such difunctional butene with carbon monoxide and, if appropriate, an alcohol, at an elevated temperature under superatmospheric pressure, in the presence of at least one source of hydrogen chloride and a catalytically effective amount of palladium, at least a portion of which palladium being in the zero oxidation state, as well as a quaternary onium chloride of nitrogen or phosphorus, the nitrogen or phosphorus atom being tetracoordinated to carbon atoms, with the proviso that the nitrogen atom may be coordinated to two pentavalent phosphorus atoms.Type: GrantFiled: May 18, 1992Date of Patent: May 17, 1994Assignee: Rhone-Poulenc ChimieInventors: Marc Huser, Sylvain Mutez, Robert Perron
-
Patent number: 5214203Abstract: Carboxylic acids are produced in the liquid phase carbonylation reaction from an alcohol or its derivative and carbon monoxide in the presence of a catalyst system containing a rhodium component and an alkyl halide and water, adding an iodide salt to the rhodium/alkyl halide catalyst system so as to maintain the iodine ion concentration in the carbonylation reaction solution at 0.3 mol/.lambda. or higher.Type: GrantFiled: April 27, 1992Date of Patent: May 25, 1993Assignee: Daicel Chemical Industries, Ltd.Inventors: Hiroshi Koyama, Hidetaka Kojima
-
Patent number: 5003104Abstract: This invention involves a process for the carbonylation of a carbonylatable reactant, e.g., an alkyl ester, a dialkyl ether or mixtures thereof by reacting the same with carbon monoxide. The process comprises effecting the carbonylation in the presence of a solution of a catalyst system containing a rhodium compound, an iodide and a lithium component at a temperature of from 50.degree. C. to 400.degree. C. at a carbon monoxide partial pressure of 1 psig to 15,000 psig. Hydrogen may also be present. The invention also concerns a carbonylation catalyst system effective for the addition of carbon monoxide to a carbonylatable reactant which comprises a solution containing as essential components a rhodium containing active component, an iodide and a lithium component.Type: GrantFiled: October 31, 1988Date of Patent: March 26, 1991Assignee: BP Chemicals LimitedInventors: Frank E. Paulik, Arnold Hershman, Walter R. Knox, Robert G. Schultz, James F. Roth
-
Patent number: 4981619Abstract: A process for preparing alpha-hydroxycarboxylic acids. An organic halide is reacted with carbon monoxide and a hydrogen donor compound, in the presence of a carbonylation catalyst and an inorganic base, at a temperature of at least 90.degree. C.Type: GrantFiled: November 28, 1986Date of Patent: January 1, 1991Assignee: Rhone Poulenc Specialities ChimiquesInventor: Bernard Besson
-
Patent number: 4855487Abstract: An improved process for preparing a fluorine-containing carboxylic acid ester useful as an intermediate for producing a fluorine-containing carboxylic acid is disclosed. The process comprises reacting a fluorine-containing alkyl halide with carbon monoxide and an alcohol in the presence of a transition metal catalyst of the Group VIII of the Periodic Table and a base, and provides the desired carbonylated compound in high yield.Type: GrantFiled: July 10, 1987Date of Patent: August 8, 1989Assignee: Sagami Chemical Research CenterInventors: Takamasa Fuchikami, Hisao Urata, Yoshimitsu Ishii, Yoshiko Obata
-
Patent number: 4820823Abstract: In accordance with a process of the present invention, .alpha.-keto acids of the general formula RCOCOOH wherein R is aryl, alkenyl or heterocyclic group, can be obtained through one-step carbonylation reaction of an organic halogenide of the general formula RX wherein R is the same as above and X is a halogen atom, with carbon monoxide and water in the presence of a basic compound and a palladium containing catalyst.Type: GrantFiled: February 21, 1986Date of Patent: April 11, 1989Assignee: Director-General of Agency of Industrial Science and TechnologyInventors: Masato Tanaka, Toshiaki Kobayashi, Toshiyasu Sakakura
-
Patent number: 4761499Abstract: High yields of olefinic esters and amides, and the like are derived from a process wherein vinyl dihalides are carbonylated in the presence of a palladium catalyst and a primary or secondary amine base or tertiary amine, depending on the desired product, and a solvent.Type: GrantFiled: June 2, 1987Date of Patent: August 2, 1988Assignee: Akzo America Inc.Inventor: Ronald A. Epstein
-
Patent number: 4738802Abstract: A process for the production of an alkyl .alpha.-keto-carboxylic acid of the general formula: ##STR1## wherein: R is a linear or branched alkyl radical having from 1 to about 20 carbon atoms which comprises reacting an alkyl halide of the formula:RXwhere R is as defined above and X represents halogen, in a liquid solvent medium, with carbon monoxide at elevated temperature and pressure in the presence of a catalytic amount of a metal carbonyl compound and an alkali metal inorganic base or an alkaline earth metal inorganic base. Optionally, small amounts of LiI and/or bis(1,2-diphenylphosphino)ethane may be present in the reaction as co-catalysts.Type: GrantFiled: November 16, 1983Date of Patent: April 19, 1988Assignee: Ethyl CorporationInventor: John Y. Lee
-
Patent number: 4733006Abstract: The present invention provides for an improved process wherein an olefin, an alcohol, or an ester, halide or ether derivative of said alcohol is reacted with carbon monoxide in a liquid phase in the presence of a catalyst system that contains (a) a rhodium component, and (b) and iodine or bromine component. By passing at least a portion of the liquid reaction mass from the reaction zone to a separation zone of substantially lower CO partial pressure, at least a portion of the carbonylation products, as well as unreacted carbon monoxide, inert gases and unreacted olefin, alcohol or alcohol derivatives are vaporized and can be withdrawn from the separation zone. Precipitation of the rhodium catalyst under carbon monoxide deficient conditions is prevented or retarded by addition to the carbon monoxide deficient zones of the system of a catalyst stabilizer which is a germanium (IV) compound, an alkali metal compound, and mixtures thereof.Type: GrantFiled: August 18, 1983Date of Patent: March 22, 1988Assignee: Monsanto CompanyInventors: Thomas C. Singleton, Frank E. Paulik
-
Patent number: 4713484Abstract: A process for preparing carboxylic acid salts by the reaction of carbon monoxide with substituted or unsubstituted aromatic halides or an aliphatic organic halide. The process comprises the catalytic single phase carbonylation of the halide utilizing in addition to carbon monoxide, a palladium catalyst, an excess of tertiary phosphine, optionally an amine compound, with an alkali metal or alkaline earth metal base added during the reaction to form the salt.Type: GrantFiled: December 22, 1986Date of Patent: December 15, 1987Assignee: Stauffer Chemical CompanyInventor: Ronald A. Epstein
-
Patent number: 4642370Abstract: Carboxylic acid esters are produced by reacting (i) carbon monoxide, (ii) a compound of the formula M(OR).sub.x wherein M is either boron, silicon, aluminum, titanium or zirconium, x is the valency of M and R is a hydrocarbyl group and (iii) a hydrocarbyl halide, wherein the halide moiety is bromide, chloride or iodide, in the presence of a catalyst comprising one or more of the metals rhodium, iridium and cobalt in either elemental or compound form. When M is boron, silicon or aluminum and the halide moiety is chloride, there is preferably added a source of iodide.Type: GrantFiled: March 14, 1985Date of Patent: February 10, 1987Assignee: The British Petroleum Company p.l.c.Inventors: Howard Alper, David J. H. Smith, James B. Woell
-
Patent number: 4582929Abstract: This invention is a process for the carbonylation of an organic halide to prepare a carbonyl-containing compound, and recovery of halogen values in a useful form which comprises(a) contacting an organic halide with carbon monoxide and an esterifying agent, a primary or secondary amine, or hydrogen gas, in an inert organic solvent in the presence of a water-insoluble tertiary amine or pyridine ring-containing compound, and a catalytic amount of a Group VIII metal catalyst, under conditions such that an organic ester, amide or aldehyde is prepared and the halide generated in the process forms a salt with tertiary amine or pyridine compound wherein the halide is bromine or iodine;(b) separating the organic ester, amide or aldehyde from the reaction mixture which contains the tertiary amine or pyridine compound-halide salt;(c) contacting the reaction mixture containing the tertiary amine or pyridine compound-halide salt mixture with a concentrated aqueous solution of an alkali metal base or alkaline earth metal bType: GrantFiled: December 24, 1984Date of Patent: April 15, 1986Assignee: The Dow Chemical CompanyInventor: Robert A. DeVries
-
Patent number: 4544505Abstract: Halo-.alpha.-keto-carboxylic acids are prepared by reacting a dihaloalkane in a liquid solvent medium with carbon monoxide at elevated temperature and pressure in the presence of a catalytic amount of a metal carbonyl compound and an alkali metal inorganic base or an alkaline earth metal inorganic base.Type: GrantFiled: October 21, 1983Date of Patent: October 1, 1985Assignee: Ethyl CorporationInventor: Joachim W. Wolfram
-
Patent number: 4473706Abstract: Cyclic-keto-acids of the general formula: ##STR1## wherein R is hydrogen or a monovalent alkyl radical which can be either straight chain or branched having from 1 to about 20 carbon atoms and X=1, 3, or 4, are prepared by reacting a functionalized 1-bromoalkane of the formula: ##STR2## wherein R and X are as defined above and Y is a leaving group, preferably the halogens, in a liquid solvent medium with carbon monoxide at elevated temperature and pressure in the presence of a catalytic amount of a metal carbonyl compound and an alkali or an alkaline earth metal inorganic base.Type: GrantFiled: August 6, 1982Date of Patent: September 25, 1984Assignee: Ethyl CorporationInventors: John Y. Lee, Thomas J. Walter
-
Patent number: 4451670Abstract: A process for the production of isobutyryl fluoride by reacting isopropyl fluoride and carbon monoxide in the presence of anhydrous hydrofluoric acid is described.Type: GrantFiled: November 2, 1982Date of Patent: May 29, 1984Assignee: Ashland Oil, Inc.Inventors: Dace Grote, Robert A. Grimm, Richard V. Norton
-
Patent number: 4435575Abstract: A process is herein described for preparing carboxylated organic compounds (acids, esters, alkaline salts) of formula ##STR1## wherein R is a hydrocarbyl group having up to 11 carbon atoms (an aliphatic, alicyclic, aryl- or heteroarylalkyl group), also substituted, in its turn, by groups inert under the reaction conditions (alkyl, aryl, etheric, thioetheric, halogen, nitrile, ester, amide, ketonic groups), and R' is a hydrogen atom or an alkyl C.sub.1 -C.sub.8 group, by reaction of carbon monoxide with the corresponding hydrocarbyl halides, having the halogen bound to a non-tertiary carbon atom, in the presence of catalysts which are salts of cobalt hydrocarbonyl, or precursors thereof, in a hydro-alcoholic or alcoholic solvent and in the presence of bases.The process is characterized in that the catalytic system composed by the salt of cobalt hydrocarbonyl is supported on an anion exchange resin.Type: GrantFiled: June 30, 1981Date of Patent: March 6, 1984Assignee: Montedison S.p.A.Inventors: Gianfranco Cainelli, Marco Foa', Achille U. Ronchi, Andrea Gardano
-
Patent number: 4433166Abstract: The present invention provides for an improved process wherein an olefin, an alcohol, or an ester, halide or ether derivative of said alcohol is reacted with carbon monoxide in a liquid phase in the presence of a catalyst system containing a rhodium component and an iodine or bromine component. By passing at least a portion of the liquid reaction mass from the reaction zone to a separation zone of substantially lower CO partial pressure, at least a portion of the carbonylation products, as well as unreacted carbon monoxide, inert gases, and unreacted olefin, alcohol, or alcohol derivatives are vaporized and can be withdrawn from the separation zone. Precipitation of the rhodium catalyst under carbon monoxide deficient conditions is prevented or retarded by addition to the system of a stabilizer which is a tin component which may be tin or a tin compound.Type: GrantFiled: December 29, 1980Date of Patent: February 21, 1984Assignee: Monsanto CompanyInventors: Thomas C. Singleton, Frank E. Paulik
-
Patent number: H53Abstract: Processes for producing 4,4-dimethyl-3-isoxazolidinone and intermediates for it from known and inexpensive starting materials are described and exemplified.Type: GrantFiled: February 21, 1984Date of Patent: April 1, 1986Assignee: FMC CorporationInventors: Borivoj R. Franko-Filipasic, Sol A. Mednick, James Snyder