From Olefins Utilizing Group Viii Noble Metal Catalyst Patents (Class 560/243)
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Patent number: 6180821Abstract: Acetic acid and/or vinyl acetate are produced by an integrated process in which a gaseous feedstock comprising ethylene and/or ethane and optionally steam is contacted in a first reaction zone (step (a)) with a molecular oxygen-containing gas in the presence of a catalyst active for the oxidation of ethylene to acetic acid and/or ethane to acetic acid and ethylene to produce a first product stream comprising acetic acid, water and ethylene (either as unreacted ethylene and/or as co-produced ethylene) and optionally also ethane, carbon monoxide, carbon dioxide and/or nitrogen.Type: GrantFiled: December 14, 1999Date of Patent: January 30, 2001Assignee: BP Chemicals LimitedInventors: Simon Jobson, Derrick John Watson
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Patent number: 6118021Abstract: A process and apparatus for vinyl acetate production. A membrane unit containing a membrane selectively permeable to ethylene over argon is used to recover ethylene from the argon purge stream.Type: GrantFiled: October 5, 1998Date of Patent: September 12, 2000Assignee: Membrane Technology and Research, Inc.Inventors: Douglas Gottschlich, Richard W. Baker
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Patent number: 6040474Abstract: 1.Type: GrantFiled: April 6, 1998Date of Patent: March 21, 2000Assignee: BP Chemicals LimitedInventors: Simon Jobson, Derrick John Watson
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Patent number: 5808136Abstract: A catalyst and method of its production for use in making vinyl acetate monomer. The carrier is impregnated with a basic solution and a solution containing gold salts and palladium salts and finally impregnated with alkali acetate. The activity and selectivity of the catalyst, its mechanical strength, the noble-metal adhesion and the dispersion of noble metal on the carrier can be improved if the carrier is impregnated in a pretreatment with salts containing as cation elements of groups IA, IIA, IIIA and IVB of the periodic table and as anions elements of group VIIA or complex anions such as nitrate, sulfate or anions of organic acids such as acetate and lactate and is subsequently dried and calcined at temperatures of at least 160.degree. C.Type: GrantFiled: January 23, 1996Date of Patent: September 15, 1998Assignee: Degussa AktiengesellschaftInventors: Thomas Tacke, Herbert Mueller, Uwe Ohlrogge, Francis P. Daly, Hans Lansink Rotgerink, Helmfried Krause
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Patent number: 5789609Abstract: Disclosed are an optically active diphosphine represented by formula: ##STR1## wherein R represents a lower alkyl group having 1 to 4 carbon atoms; Ar represents a phenyl group which may be substituted with a lower alkyl group having 1 to 4 carbon atoms and/or a lower alkoxy group having 1 to 4 carbon atoms, a transition metal complex containing the diphosphine as a ligand, and a process for producing an optically active .delta.-oxo-.alpha.-cyano ester using the transition metal complex as a catalyst.Type: GrantFiled: October 22, 1997Date of Patent: August 4, 1998Assignee: Takasago International CorporationInventors: Kyoko Tamao, Koji Inagaki, Noboru Sayo
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Patent number: 5559071Abstract: Surface impregnated catalyst, process for the production thereof, and use thereof for the preparation of vinyl acetate. The invention relates to Pd/K/Au, Pd/K/Ba or Pd/K/Cd supported catalysts built up in the form of an outer layer, the production thereof and also the use thereof for preparing vinyl acetate from ethylene, acetic acid and oxygen in the gas phase. The catalysts specified are produced by impregnating the support particles, while mixing intimately, with a solution of salts of the corresponding elements and then drying the support particles immediately, with the dynamic viscosity of the solution being at least 0.003 Pa.multidot.s and the solution volume in impregnation being from 5 to 80% of the pore volume of the support particles.Type: GrantFiled: July 18, 1994Date of Patent: September 24, 1996Assignee: Hoechst AktiengesellschaftInventors: Roland Abel, Karl-Fred Worner
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Patent number: 5559267Abstract: Chiral 1,4-diol cyclic sulfates and their use as precursors in the preparation of chiral phospholane ligands, and chiral complexes useful as catalysts for carrying out enantioselective reactions.Type: GrantFiled: May 24, 1995Date of Patent: September 24, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventor: Mark J. Burk
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Patent number: 5554786Abstract: A process which comprises reacting an aliphatic or cycloaliphatic olefin, having 4 to 16 carbon atoms in its main chain and a non-terminal double bond, with a carboxylic acid, in the presence of hydrogen peroxide and a catalyst consisting of a palladium salt or complex.Type: GrantFiled: May 5, 1995Date of Patent: September 10, 1996Assignee: Firmenich S.A.Inventors: Hubert Mimoun, Chengguo Jia
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Patent number: 5466837Abstract: An ethylene stream which contains ethane as an impurity or a propylene stream which contains propane as an impurity is subjected to adsorption at a temperature of 50.degree. to 200.degree. C. in a bed of adsorbent which selectively adsorbs ethylene or propylene, thereby adsorbing substantially all of the ethylene or propylene. The purified ethylene or propylene stream is then subjected to partial oxidation in the presence of oxygen and, optionally ammonia to produce various partial oxidation products. The process is operated on a low per pass conversion with recycle of unreacted ethylene or propylene. In the system of the invention the adsorption unit may be upstream or downstream of the partial oxidation reactor.Type: GrantFiled: April 22, 1994Date of Patent: November 14, 1995Assignee: The BOC Group, Inc.Inventors: Ramakrishnan Ramachandran, Loc H. Dao
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Patent number: 5322633Abstract: Branched chain carboxylic esters are prepared by reacting an unsaturated PAO such as 1-decene dimer with CO and an aliphatic alcohol solvent in the presence of an acid and a noble metal catalyst complex such as RuCl.sub.3 /Ph.sub.3 P or PdCl.sub.3 /Ph.sub.3 P.Type: GrantFiled: November 16, 1992Date of Patent: June 21, 1994Assignee: Albemarle CorporationInventors: K. Pushpananda A. Senaratne, Kenneth C. Lilje
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Patent number: 5008445Abstract: The present invention relates to a process for producing glycol monoesters by reacting carboxylic acid, olefin and oxygen in the presence of a catalyst containing (A) a palladium component, (B) an oxygen-containing nitrogen compound, and (C) a metal halide in the specified ratio of (A), (B), (C).According to the present invention, the regeneration of the catalyst through reduction is easy and the catalyst of high activity can be used repeatedly.Type: GrantFiled: June 5, 1987Date of Patent: April 16, 1991Assignee: Idemitsu Kosan Company LimitedInventors: Nobuaki Shimizu, Hiroaki Kezuka
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Patent number: 4900462Abstract: A polar lubricating fluid comprising aliphatic molecules having hydroxy or ester functional groups. The alcohol lubricant molecules have at least 20 carbon atoms and the ester molecule comprises between 26 and 100 carbon atoms. The oxygenate content of both molecules is at least 0.2 mmoles per gram of lubricant. The alcohol lubricating fluid is produced by a process comprising hydroformylating olefins having at least 20 carbon atoms in the presence of a hydroformylating catalyst and synthesis gas comprising H.sub.2 and CO. The ester lubricating fluid is produced by a subsequent acylation. The reaction is carried out between 150.degree. C. and 300.degree. C.Type: GrantFiled: January 13, 1988Date of Patent: February 13, 1990Assignee: Mobil Oil Corp.Inventors: Werner O. Haag, Robert E. Palermo
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Patent number: 4749808Abstract: The invention relates to the use of metal cation-exchangeable layered clays in organic reactions which are catalysed by protons in which intercalated water is not a stoichiometric reactant. Such organic reactions include the production of esters by the reaction of an olefin or an olefin oxide with a carboxylic acid, the production of ethers by reaction of an alcohol with an olefin or an olefin oxide, the production of ethers by the reaction of a primary or secondary aliphatic alcohol or an olefin oxide, the production of bis-sec-alkyl ethers from alkenes, the production of alkyl aromatic compounds by the reaction of an aromatic hydrocarbon with an olefin or alcohol and the production of alcohols by the hydration of olefins.Type: GrantFiled: June 18, 1986Date of Patent: June 7, 1988Assignee: British Petroleum Company p.l.c.Inventors: James A. Ballantine, John H. Purnell, John M. Thomas
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Patent number: 4658053Abstract: A process for the production of an ester comprises reacting an olefin with carbon monoxide, hydrogen and another ester at elevated temperature and pressure in the presence of a catalyst comprising (1) a rhodium source, (2) a ruthenium source, and (3) cobalt or zinc iodide. The product ester comprises the acid group of the ester used as reactant esterified with a hydrocarbyl group derived from the olefin, hydrogen and carbon monoxide.Type: GrantFiled: February 25, 1985Date of Patent: April 14, 1987Assignee: BP Chemicals LimitedInventor: Michael J. Green
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Patent number: 4647690Abstract: A process and catalyst for the acetoxylation of propylene, said catalyst consisting essentially of palladium, bismuth, potassium, and rubidium.Type: GrantFiled: September 24, 1985Date of Patent: March 3, 1987Assignee: Phillips Petroleum CompanyInventor: Charles A. Drake
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Patent number: 4634794Abstract: A process and catalyst for the acetoxylation of propylene, said catalyst consisting essentially of palladium, bismuth, and rubidium on a support.Type: GrantFiled: January 24, 1986Date of Patent: January 6, 1987Assignee: Phillips Petroleum Co.Inventors: Charles A. Drake, Stephen E. Reiter
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Patent number: 4634793Abstract: A process for the dimerization in the liquid phase of an aliphatic mono-olefin having 2 to about 12 carbon atoms with a catalytic system formed by combining, in the presence of water, an alcohol or a carboxylic acid,a. a palladium compound,b. a chelate ligand having as coordinating atoms at least two Group Va atoms which are connected through a chain comprising 2 to about 6 carbon atoms, andc. a compound containing an anion of an acid, except hydrohalogenic acids.Type: GrantFiled: October 3, 1985Date of Patent: January 6, 1987Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4614816Abstract: A carboxylic acid or an ester thereof having at least two carbon atoms more than formic acid is prepared by reacting at elevated temperature e.g. 100.degree. to 250.degree. C. formic acid or a formate ester with an olefin e.g. ethylene in the presence of, as catalyst, a Group VIII noble metal e.g. iridium, preferably promoted by iodide, to cause addition of the formic acid or ester to the olefin and form the a higher acid e.g. propionic acid or ester thereof.A strong acid such as a sulphonic acid may be used as a copromoter. The catalyst is employed in solution.Type: GrantFiled: October 13, 1983Date of Patent: September 30, 1986Assignee: BP Chemicals LimitedInventors: David J. Drury, Peter S. Williams
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Patent number: 4602103Abstract: C.sub.4 olefins comprising cis- and trans-butane-2 and butene-1 may be oxidized to their corresponding mono- and diacetates in the presence of acetic acid and an olefin-activated palladium catalyst under mild conditions. With this catalyst, and depending in part upon the solvent employed, as well as other operating conditions, the formation of linear allylic 1-acetates over the corresponding branched compounds can be favored in order to increase the yield of the corresponding linear 1,4-diacetates. The latter, in turn, may then be converted, for example, to butanediol by known hydrogenation methods.In a similar manner, isobutylene may be converted to a dialcohol.Type: GrantFiled: April 10, 1985Date of Patent: July 22, 1986Assignee: Sun Refining and Marketing CompanyInventor: James E. Lyons
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Patent number: 4602104Abstract: Propylene is oxidized directly to allyl acetate in the presence of acetic acid with air or oxygen in the liquid phase under moderate reaction conditions employing a palladium-on-carbon catalyst which has been pre-treated by activating it with propylene at temperatures of greater than about 50.degree. C., preferably from 60.degree. to 150.degree. C., for a period of time sufficient to form a small but perceptible quantity of said activated catalyst, preferably for at least 10 minutes in the substantial absence of oxygen.Type: GrantFiled: April 10, 1985Date of Patent: July 22, 1986Assignee: Sun Refining and Marketing CompanyInventors: James E. Lyons, George Suld
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Patent number: 4571431Abstract: A process for providing high space time yields in the acetoxylation of propylene involving the use of a catalyst consisting esssentially of palladium, potassium, bismuth, and a promoting amount of magnesium or a combination of magnesium and barium.Type: GrantFiled: May 24, 1985Date of Patent: February 18, 1986Assignee: Phillips Petroleum CompanyInventor: Charles A. Drake
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Patent number: 4550097Abstract: A process for providing high space time yields in the acetoxylation of propylene involving the use of a catalyst consisting essentially of palladium, potassium, bismuth, and a promoting amount of magnesium or a combination of magnesium and barium.Type: GrantFiled: August 20, 1984Date of Patent: October 29, 1985Assignee: Phillips Petroleum CompanyInventor: Charles A. Drake
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Patent number: 4508653Abstract: The oxidation process for the manufacture of acyloxy styrenes comprises contacting a compound such as styrene or ethyl benzene, a carboxylic acid and molecular oxygen in the liquid phase at an elevated temperature with a catalyst composed of palladium or a compound of palladium, and a compound of at least one member selected from the group consisting of antimony, lead, cobalt, nickel, iron, copper, zinc, chromium, tin and optionally also an alkali metal compound is described.Type: GrantFiled: March 14, 1983Date of Patent: April 2, 1985Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4436928Abstract: A process for the production of alkane acetates from olefins in the presence of an oxide/borate catalyst system, oxygen and a carboxylate ion source via oxidative esterification is described. The reaction is conducted at a temperature in the range of 100.degree. to 250.degree. C. and a pressure of 1 atmosphere or greater. Alkane diacetates and hydroxy acetates are produced which may be used as precursors to alkylene oxides, alkylene glycols and other useful compounds.Type: GrantFiled: July 28, 1982Date of Patent: March 13, 1984Assignee: Texaco Inc.Inventors: John R. Sanderson, Terry L. Renken, Lewis W. Watts, Jr.
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Patent number: 4365082Abstract: Olefins are oxidized to unsaturated esters by means of molecular oxygen in the presence of a carboxylic acid and an organometallic palladium complex containing two identical or different hydroxamate anions or one hydroxamate anion and a carboxylate anion, said complex acting as catalyst.Type: GrantFiled: June 26, 1981Date of Patent: December 21, 1982Assignee: Institut Francais du PetroleInventors: Jean P. Laloz, Hubert Mimoun, Jean J. Rouxel, Lucien Saussine
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Patent number: 4348537Abstract: Olefin is oxidized in the absence of oxygen with a carboxylic acid in the presence of Mn(IV) oxide promoted with a noble metal to produce an effluent which includes mono and/or diester corresponding to the olefin and acid.Type: GrantFiled: June 8, 1981Date of Patent: September 7, 1982Assignee: The Lummus CompanyInventors: Joon T. Kwon, Abraham P. Gelbein
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Patent number: 4331608Abstract: Unsaturated compounds having at least 4 carbon atoms, including unsaturated alicyclic compounds having at least 4 carbon atoms, unsaturated aliphatic compounds having at least one carbon-carbon unsaturated bond and having at least 4 carbon atoms and unsaturated aromatic compounds having at least one carbon-carbon unsaturated bond in the branched chain thereof and (ii) aldehydes or ketones having at least 4 carbon atoms are catalytically co-oxidized with an oxygen-containing gas in a liquid phase to form a cleaveged product or products of unsaturated bond of the unsaturated compounds at a high yield. This co-oxidation reaction is carried out in the presence of a heavy metal containing iron, cobalt, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum, copper, silver, chromium, molybdenum, tungsten, manganese and rhenium and the compounds thereof.Type: GrantFiled: June 2, 1980Date of Patent: May 25, 1982Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Keiji Kawamoto, Toshihiro Yoshioka
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Patent number: 4323698Abstract: This specification discloses an insoluble resin-metal compound complex, the method for its preparation, and its use in carrying out a catalyzed reaction. The complex is a weak base anion exchange resin which has been contacted with a solution of a coordination compound having at least two ligands connected to at least one central metal atom to bond chemically the resin to the metal atom by replacement of at least one of the ligands of the coordination compound by a functional group of the weak base anion exchange resin. The complex can be used as a catalyst for hydrogenation, carbon monoxide insertion, polymerization, isomerization, vinyl ester exchange, and ethylene oxidation reactions, among others.Type: GrantFiled: January 21, 1980Date of Patent: April 6, 1982Assignee: Mobil Oil CorporationInventors: Werner O. Haag, Darrell D. Whitehurst
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Patent number: 4313893Abstract: Oxygenated organic compounds, e.g. esters, aldehydes, and amides, are prepared by reacting an olefinically unsaturated compound with carbon monoxide and a compound containing a replaceable hydrogen atom in the presence of a catalyst comprising cobalt or ruthenium carbonyl and a promoter ligand. The promoter ligand is selected from the group consisting of heterocyclic nitrogen compounds and phosphorus or sulfur oxides. These reactions are carried out under relatively mild conditions of temperature and pressure.Type: GrantFiled: October 31, 1979Date of Patent: February 2, 1982Assignee: Standard Oil CompanyInventors: Frederick A. Pesa, Thomas A. Haase
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Patent number: 4260750Abstract: A process for the telomerization of dienes with a telomerizing compound containing a mobile hydrogen atom is disclosed wherein the reaction between the diene and the telomerizing agent is effected in the presence of a catalytic system comprising a water-soluble sulfonated triaryl phosphine compound, preferably a water-soluble salt of a mono-, di-, or trisulfonated triphenyl phosphine and a transition metal compound, preferably palladium or a palladium-containing compound. Water is added either before or after the reaction is completed and the reaction products can easily be separated from the aqueous catalyst solution.Type: GrantFiled: March 13, 1980Date of Patent: April 7, 1981Assignee: Rhone-Poulenc IndustriesInventor: Emile Kuntz
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Patent number: 4221916Abstract: Saturated vicinal esters produced by reacting olefins with carboxylic acid and anhydrides thereof in the presence of oxygen and a vanadium- or ruthenium-containing catalyst.Type: GrantFiled: August 25, 1978Date of Patent: September 9, 1980Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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Patent number: 4211880Abstract: This specification discloses an insoluble resin-metal compound complex, the method for its preparation, and its use in carrying out a catalyzed reaction. The complex is a weak base anion exchange resin which has been contacted with a solution of a coordination compound having at least two ligands connected to at least one central metal atom to bond chemically the resin to the metal atom by replacement of at least one of the ligands of the coordination compound by a functional group of the weak base anion exchange resin. The complex can be used as a catalyst for hydrogenation, carbon monoxide insertion, polymerization, isomerization, vinyl ester exchange, and ethylene oxidation reactions, among others.Type: GrantFiled: December 4, 1978Date of Patent: July 8, 1980Assignee: Mobil Oil CorporationInventors: Werner O. Haag, Darrell D. Whitehurst
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Patent number: 4161610Abstract: This invention involves a method of producing vinyl esters by the reaction of olefins with carboxylic acids in the presence of alkali and alkaline earth metal salts of carboxylic acids, a noble metal compound, and a regenerative oxidant capable of maintaining the noble metal in oxidized form.Type: GrantFiled: September 29, 1961Date of Patent: July 17, 1979Assignee: Union Oil Company of CaliforniaInventor: Donald L. Klass
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Patent number: 4062872Abstract: An improved catalyst structure for use in catalytic processes, consisting of a powdered catalyst, carrier, and metal fiber thoroughly mixed to assure a permanent uniform distribution of the metal fiber, the catalyst-metal fiber mixture then pressed into any desired shape for its intended use. The permanent uniform dispersion of metal fibers results in a catalyst structure having increased thermal conductivity and more uniform porosity, the improved heat transfer characteristics increasing selectivity and minimizing temperature gradients in the catalytic structure thereby assuring constant reactor temperature and imparting stability, improved yield and temperature control in highly exothermic and endothermic catalytic reactions.Type: GrantFiled: May 24, 1976Date of Patent: December 13, 1977Assignee: Brunswick CorporationInventors: Sandy Y. Lew, Edward F. Conley
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Patent number: 4057575Abstract: The invention comprises the oxidation of olefins to unsaturated esters of organic acids or acetals and/or unsaturated ethers of alcohols by contacting the olefin with an organic acid or alcohol reactant in the presence of a catalyst comprising a compound of a Group VIII noble metal and a redox agent. The catalyst is maintained active by contacting it with oxygen introduced simultaneously or intermittently with the olefin or by circulating the catalyst between separate oxygen and olefin contacting zones. The oxidation can be performed under liquid phase conditions by initiating the contacting with a dissolved catalyst or can be performed under vapor phase conditions by initiating the contacting with the catalyst distended on a solid support.Type: GrantFiled: June 23, 1976Date of Patent: November 8, 1977Assignee: Union Oil Company of CaliforniaInventor: Donald L. Klass
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Patent number: 4052442Abstract: A process for preparing glycol esters such as ethylene glycol diacetate which comprises contacting a monoolefin such as ethylene with an organic monocarboxylic acid such as acetic acid containing a palladous salt and either a nitrate or a nitrite.Type: GrantFiled: January 12, 1967Date of Patent: October 4, 1977Assignee: Kuraray Co., Ltd.Inventors: Masuhiko Tamura, Teruo Yasui
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Patent number: 4051181Abstract: A three-step process for the production of acrolein and/or acrylic acid from propylene involves oxidizing the propylene in the presence of a palladium catalyst and acetic acid to produce allyl acetate, hydrolyzing the resulting allyl acetate to produce allyl alcohol and acetic acid, recycling the acetic acid produced to the propylene oxidation step, and oxidizing the allyl alcohol in the presence of a supported palladium-copper or palladium-silver metal catalyst. The acrolein and/or acrylic acid is produced in good yield at low temperatures.Type: GrantFiled: August 11, 1975Date of Patent: September 27, 1977Assignee: National Distillers and Chemical CorporationInventor: Jawad H. Murib