Of Alcohol Patents (Class 562/538)
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Patent number: 5179218Abstract: A process for the preparation of an alkanoic acid which comprises reacting the corresponding alkanol with a solubilized stable free radical nitroxide having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R.sub.5 and R.sub.6 is alkyl, hydrogen, aryl or a substituted heteroatom, nitric acid, and a bromide ion-containing compound in the presence of an oxidant at a temperature in the range of from about 25.degree. C. to about 60.degree. C., and thereafter separating out the alkanoic acid.Type: GrantFiled: September 30, 1991Date of Patent: January 12, 1993Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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Patent number: 5175359Abstract: A process for the preparation of an alkoxyalkanoic acid of the formulaRO(CH.sub.2 CHR'O).sub.n CH.sub.2 CO.sub.2 Hwherein R is an alkyl group of from 1 to about 22 carbon atoms, R' is hydrogen or methyl or mixtures thereof (on the individual molecule) and n is an integer of from 1 to about 20, which comprises reacting the corresponding alkoxyalkanol with a solubilized stable free radical nitroxide having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R.sub.5 and R.sub.6 is alkyl, hydrogen, aryl or a substituted heteroatom, a NO.sub.x -generating compound selected from the group consisting of an alkali metal nitrosodisulfonate, nitric acid, nitrous acid and mixtures thereof, and a chloride ion-containing compound in the presence of an oxidant at a temperature in the range of from about 0.degree. C. to about 100.degree. C. and thereafter separating out the alkoxyalkanoic acid.Type: GrantFiled: August 30, 1991Date of Patent: December 29, 1992Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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Patent number: 5175360Abstract: This invention relates to a process for the preparation of an alkoxyalkanoic acid of the formulaRO(CH.sub.2 CHR'O).sub.n CH.sub.2 CO.sub.2wherein R is an alkyl group of from 1 to about 22 carbon atoms, R' is hydrogen or methyl or mixtures thereof (on the individual molecule) and n is an integer of from 1 to about 12 which comprises reacting the corresponding alkoxyalkanol with a solubilized stable free radical nitroxide having the formula: ##STR1## wherein (1) (a) each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms, and (b) R.sub.5 and R.sub.6 (i) each is an alkyl group having 1 to about 15 carbon atoms provided that when R.sub.1 -R.sub.6 are not all alkyl groups, or a substituted alkyl group having 1 to about 15 carbon atoms wherein the substituent is halogen, cyano, --CONH.sub.2, --OCOCH, OCOC.sub.2 H.sub.Type: GrantFiled: November 26, 1990Date of Patent: December 29, 1992Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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Patent number: 5166423Abstract: A process for the preparation of an alkanoic acid which comprises reacting the corresponding alkanol with a solubilized stable free radical nitroxide having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R.sub.5 and R.sub.6 is alkyl, hydrogen, aryl or a substituted heteroatom, and nitric acid in the presence of an oxidant at a temperature in the range of from about 25.degree. C. to about 65.degree. C. and thereafter separating out the alkanoic acid.Type: GrantFiled: August 30, 1991Date of Patent: November 24, 1992Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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Patent number: 5166424Abstract: A process is disclosed for the preparation of aliphatic monocarboxylic acids from primary aliphatic alcohols having 2 to 6 carbon atoms wherein the reaction is in semi-continuous or continuous mode. Acetic acid is prepared from ethanol in high conversion, selectivity and yield. Acetic acid is useful as a solvent for the manufacture of terephthalic acid and other organic compounds.Type: GrantFiled: December 18, 1991Date of Patent: November 24, 1992Assignee: Amoco CorporationInventors: Kristi A. Fjare, Calvin T. Chew
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Patent number: 5166422Abstract: A process for the preparation of an alkanoic acid which comprises reacting the corresponding alkanol with a solubilized stable free radical nitroxide having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R.sub.5 and R.sub.6 is alkyl, hydrogen, aryl or a substituted heteroatom, and an alkali metal nitrosodisulfonate in the presence of an oxidant at a temperature in the range of from about -10.degree. C. to about 60.degree. C. and thereafter separating out the alkanoic acid.Type: GrantFiled: August 30, 1991Date of Patent: November 24, 1992Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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Patent number: 5162579Abstract: A process for the preparation of an alkoxyalkanoic acid of the formulaRO(CH.sub.2 CHR'O).sub.n CH.sub.2 CO.sub.2 Hwherein R is an alkyl group of from 1 to about 22 carbon atoms, R' is hydrogen or methyl or mixtures thereof (on the individual molecule) and n is an integer of from 1 to about 12, which comprises reacting the corresponding alkoxyalkanol with a stable free radical nitroxide having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R.sub.5 and R.sub.6 is alkyl, hydrogen, aryl or a substituted heteroatom, and nitric acid in the presence of an oxidant at a temperature in the range of from about 0.degree. C. to about 100.degree. C. and thereafter separating out the alkoxyalkanoic acid.Type: GrantFiled: August 30, 1991Date of Patent: November 10, 1992Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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Patent number: 5155263Abstract: A process for preparing .alpha.-ketobutyric acid comprising contacting 1,2-butanediol with molecular oxygen in the presence of a platinum catalyst is disclosed. The process produces .alpha.-ketobutyric acid in high yield at low cost.Type: GrantFiled: September 30, 1991Date of Patent: October 13, 1992Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Makoto Imanari, Hiroshi Iwane, Masashi Suzuki, Naoki Suzuki
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Patent number: 5122307Abstract: The instant invention relates to a process for the oxidation of primary alcohols to the corresponding acids, which comprises contacting and thereby reacting an alcohol with oxygen and a tertiary amine oxide compound at elevated temperatures in the presence of a heterogeneous catalyst comprising a Group VIII metal supported on an inert porous support and a promoter comprising a quaternary ammonium bromide, and subsequently separating out acids from the reaction mixture product.Type: GrantFiled: July 13, 1990Date of Patent: June 16, 1992Assignee: Shell Oil CompanyInventors: Tamal K. Dutta, Lynn H. Slaugh
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Patent number: 5122308Abstract: The instant invention relates to a process for the oxidation of primary alcohols to the corresponding acids, which comprises contacting and thereby reacting an alcohol with a tertiary amine oxide compound at elevated temperatures in the presence of a homogeneous oxidation catalyst comprising a Group VIII metal and a promoter comprising a quaternary ammonium bromide, and subsequently separating out acids from the reaction mixture product.Type: GrantFiled: July 13, 1990Date of Patent: June 16, 1992Assignee: Shell Oil CompanyInventors: Tamal K. Dutta, Lynn H. Slaugh
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Patent number: 5095143Abstract: A method to oxidize an oxidizable component in a liquid phase with an oxygen-containing gas is disclosed. The method comprises mixing the liquid phase and gas phase in a reactor with a rotating agitator element operated at constant power.Type: GrantFiled: June 13, 1990Date of Patent: March 10, 1992Assignee: Amoco CorporationInventors: Daniel L. Heberer, Paul R. Schiller, Virginia R. Seemann, Michael J. Yerkes
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Patent number: 5068408Abstract: A process for oxidizing an organic compound selected from an aliphatic, aromatic, aliphatic/aromatic, cycloaliphatic and heterocyclic alcohol, thiol, sulfide, aldehyde, amine, amide, ketone, acid, ether, ester, and organic compounds containing an activated carbon-carbon double bond, which process comprises contacting said organic compound dissolved in an organic solvent with a hypochlorous acid solution.Type: GrantFiled: January 31, 1990Date of Patent: November 26, 1991Assignee: Olin CorporationInventors: Robert J. Raynor, Budd L. Duncan
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Patent number: 4996007Abstract: The instant invention relates to a process for the oxidation of primary alcohols to aldehydes, acids and esters, particularly to aldehydes. In this process and alcohol and oxygen are contacted and reacted with a dihydrodihydroxynaphthalene or a dihydrodihydroxyanthracene in the presence of a Group VIII metal oxidation catalyst and optionally in the presence of a quaternary ammonium halide cocatalyst, and subsequently product aldehyde/acid/ester and the corresponding napthoquinone or anthraquinone are separated from the reaction mixture. The by-product naphthoquinone or anthraquinone is suitably recycled to the alcohol oxidation step by hydrogenating the naphthoquinone or anthraquinone to the corresponding dihydrodihydroxynaphthalene or dihydrodihydroxyanthracene by contacting it with hydrogen in the presence of a hydrogenation catalyst.Type: GrantFiled: January 19, 1990Date of Patent: February 26, 1991Assignee: Shell Oil CompanyInventors: Kuo-Hua Chao, Tamal K. Dutta, Lynn H. Slaugh
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Patent number: 4987252Abstract: In order to recover methacrolein and/or methacrylic acid by quenching a reaction product gas obtained by catalytic oxidation of isobutylene or the like, the reaction product gas is charged into a quench column through a double-wall pipe and is then brought into contact with a condensate as a cooling medium. Deposition of terephthalic acid and the like inside the column is prevented by controlling the temperature of a bottom in the quench column and that of an overhead gas of a quench column unit. An aromatic carboxylic acid, aromatic aldehyde, metal powder is added to an aqueous solution of methacrylic acid, which contains terephthalic acid and the like, so that the terephthalic acid and the like are caused to precipitate for their removal.Type: GrantFiled: June 27, 1988Date of Patent: January 22, 1991Assignees: Mitsui Toatsu Chemicals, Incorporated, Kyowa Gas Chemical Industry Co., Ltd.Inventors: Morimasa Kuragano, Kozo Iwasaki, Takeshi Isobe, Isao Fukada, Minoru Koshibe, Yoshihiro Sezaki, Hirozo Segawa, Katsuji Yoguchi
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Patent number: 4976893Abstract: The invention relates to a process for preparing carboxylic acids by platinum-catalyzed oxidation of primary alcohols of limited water solubility with oxygen in a mixture of water and a solubilizer. The solubilizer used is an ether of the general formula R.sub.1 O(CH.sub.2 CH.sub.2 O).sub.n R.sub.2, where n is 1-4 and R.sub.1 and R.sub.2 are alkyl radicals having 1-4 carbon atoms.Type: GrantFiled: June 18, 1986Date of Patent: December 11, 1990Assignee: Hoechst AktiengesellschaftInventor: Ernst I. Leupold
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Patent number: 4959494Abstract: A method for oxidizing organic compounds by contacting organic compounds with molecular oxygen in the presence of a noble metal pyrochlore having the formula:A.sub.2+x B.sub.2-x O.sub.7-ywherein A is a pyrochlore structure metal cation, and B is one or more of Ru, Rh, Ir, Os, and Pt; x and y are greater than or equal to 0 and less than or equal to 1.0, at a temperature up to about 200.degree. C.Type: GrantFiled: July 6, 1987Date of Patent: September 25, 1990Assignee: Monsanto CompanyInventor: Timothy R. Felthouse
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Patent number: 4925981Abstract: A method of isolating and recovering methacrylic acid from a methacrylic acid-containing reaction product gas resulting from the vapor-phase catalytic oxidation of isobutylene, tertiary butanol or isobutyraldehyde, which comprises introducing the reaction product gas comprising methacrylic acid and various by-products including high boiling substances at a high temperature of 250.degree. to 300.degree. C. into a cooling zone, rapidly cooling the gas therein to a temperature of not more than 100.degree. C. to condense methacrylic acid and thus isolate methacrylic acid, while also converting the high boiling substances to fumes, thereafter introducing the cooled gas containing said fumes into a venturi scrubber, contacting it therein with an aqueous medium to remove said fumes, finally introducing the treated gas into a methacrylic acid-absorbing zone and absorbing methacrylic acid by absorption into an aqueous medium.Type: GrantFiled: January 16, 1987Date of Patent: May 15, 1990Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.Inventors: Noboru Shimizu, Hiroshi Yoshida, Hiromiki Daigo, Shoichi Matsumoto
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Patent number: 4906772Abstract: A process is disclosed for the co-production of aliphatic monocarboxylic acids and polycarboxylic aromatic acids in high selectivity, conversion and yield. The aliphatic monocarboxylic acid can serve as a component of the solvent for the process.Type: GrantFiled: December 2, 1988Date of Patent: March 6, 1990Assignee: Amoco CorporationInventors: Calvin T. Chew, Rosemary F. McMahon, Kristi A. Fjare, Wayne P. Schammel
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Patent number: 4902827Abstract: Disclosed is an improved process for the preparation of adipic acid by the air oxidation of cyclohexane in the presence of acetic acid and a catalyst system comprising cobalt and zirconium and/or hafnium.Type: GrantFiled: May 3, 1988Date of Patent: February 20, 1990Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Norma L. Lafferty, Charles E. Sumner, Jr.
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Patent number: 4883910Abstract: An organic compound having a cyclic aliphatic moiety is oxidized with a vanadium containing heteropolyanion compound having the formulaA.sub.m XY.sub.12-n V.sub.n.sup.+5 O.sub.40whereinA is H, Li, K or Na:X is P.sup.+5, Si.sup.+4, Ge.sup.+4 or B.sup.+3 ;Y is Mo or W;n is an integer from 1 to 10; andm is 3+n where X is P.sup.+5 or As.sup.+5, 4+n where X is Si.sup.+4 or Ge.sup.+4, and 5+n where X is B+3.No metal catalyst is required. Exemplary is the oxidation of cyclohexanone, cyclohexanol, or any combination thereof to obtain adipic acid.Type: GrantFiled: March 20, 1985Date of Patent: November 28, 1989Assignee: E. I. Du Pont De Nemours and CompanyInventor: William C. Seidel
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Patent number: 4879412Abstract: Disclosed herein is a process for bringing methacrylic acid, which has been obtained by the catalytic oxidation of compound having 4 carbon atoms, into contact with a basic anion-exchange resin so as to remove byproduced dibasic acids and the like from the methacrylic acid and to purify the same.Type: GrantFiled: March 3, 1986Date of Patent: November 7, 1989Assignees: Mitsui Toatsu Chemicals, Inc., Kyowa Gas Chemical Industry Co., Ltd.Inventors: Kozo Iwasaki, Morimasa Kuragano, Minoru Koshibe, Yoshihiro Sezaki, Katsuji Yoguchi, Yoshio Koyama
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Patent number: 4851569Abstract: Methyl formate is produced continuously by reacting methanol in the liquid phase with molecular oxygen in the presence as catalyst of a soluble chromium compound which can be deliberately added or can result from corrosion of a reaction vessel fabricated in stainless steel or other chromium-containing metal alloy. Initiation of the oxidation can be accomplished by feeding a material more susceptible to oxidation than methanol, either with or without methanol, and optionally in the presence of a soluble chromium compound.Type: GrantFiled: June 4, 1985Date of Patent: July 25, 1989Assignee: BP Chemicals LimitedInventors: David J. Drury, John Pennington
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Patent number: 4816603Abstract: The present invention provides a process for the production of methacrolein and methacrylic acid by the gas phase catalytic oxidation of isobutylene or t-butanol at high temperature using molecular oxygen in the presence of catalyst consisting of molybdenum, tungsten, bismuth, iron, nickel, antimony, and an alkali metal, to which zinc or lead is added, and further phosphorus sulfur, silicon, selenium, germanium or boron, and magnesium, cobalt, manganese or tin are added.Type: GrantFiled: November 26, 1985Date of Patent: March 28, 1989Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Motomu Oh-Kita, Yoshiyuki Taniguchi, Masaaki Kato, Masao Kobayashi
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Patent number: 4789502Abstract: Carboxylic acids are produced in high yield by contacting alcohols, water and hydrogen with a Cu-Zn-Cr-base promoter/alumina catalyst.Type: GrantFiled: November 24, 1986Date of Patent: December 6, 1988Assignee: Shell Oil CompanyInventor: Lynn H. Slaugh
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Patent number: 4766208Abstract: A method of performing an oxidation reaction in which an alkali hypohalite is used as an oxidizing agent which comprises: carrying out the oxidation reaction in an aqueous medium with concurrently distilling off a solvent used in the reaction as the reaction proceeds under a reduced pressure.The method is in particular useful for the oxidation of diacetone-L-sorbose to diacetone-2-keto-L-gulonic acid in water. The reaction temperature is so accurately controlled that the same optimum yield of diacetone-2-keto-L-gulonic acid is obtained by the use of a reduced amount of sodium hypochlorite as compared with the conventional manner of reaction under atmospheric pressure.Type: GrantFiled: July 8, 1986Date of Patent: August 23, 1988Assignee: Takeda Chemical Industries, Ltd.Inventors: Kiyomitsu Kunugiza, Kozo Kamiya
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Patent number: 4720575Abstract: The molybdovanadophosphoric acid H.sub.8 PMo.sub.10 VO.sub.39, its PMo.sub.10 VO.sub.35 anhydride, methods for their preparation, and methods for making methacrylic acid and its esters by oxidation/dehydrogenation wherein the above acid and/or its anhydride is employed as a catalyst.Type: GrantFiled: March 7, 1986Date of Patent: January 19, 1988Assignee: Rohm GmbHInventor: Wilhelm Gruber
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Patent number: 4658056Abstract: A process for the catalytic oxidation of liquid cycloparaffins to oxidation products thereof is disclosed. In the process, partial oxidation products are formed by oxidizing the cycloparaffin with molecular oxygen-containing gas in the presence of an oxidation catalyst comprising two heavy metal compounds. The first heavy metal compound is a cobalt compound having ligands selected from dialkyl phosphate, dicycloalkylphosphate and alkylcycloalkylphosphate, optionally additionally combined with pyridine. The second heavy metal compound is a chromium alkanoate. A preferred catalyst is cobalt bis[di(2-ethylhexyl)phosphate] combined with chromium naphthenate.Type: GrantFiled: April 22, 1982Date of Patent: April 14, 1987Assignee: Du Pont Canada Inc.Inventor: Peter A. Sipos
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Patent number: 4618709Abstract: A process for separation of methacrylic acid from a methacrylic acid-containing, gaseous reaction mixture obtained by subjecting methacrolein or a compound which can afford methacrolein under reaction conditions and molecular oxygen to gas phase reaction in the presence of a catalyst for oxidation under the coexistence of an inert gas for dilution which comprises (a) cooling the gaseous reaction mixture from a reactor wherein the gas phase reaction has been effected to separate into condensable components including methacrylic acid, acetic acid and water vapor as a condensed liquor and non-condensable components including methacrolein as a non-condensed gaseous mixture, (b) eliminating contaminating methacrolein from the condensed liquor and (c) contacting the resulting condensed liquor with an organic solvent to extract methacrylic acid, followed by separation into an organic solvent solution including methacrylic acid and an aqueous solution as waste water, characterized in that (1) the inert gas for dilutiType: GrantFiled: January 30, 1981Date of Patent: October 21, 1986Assignee: Sumitomo Chemical Company, LimitedInventors: Masao Sada, Michio Kato, Masami Ayano, Tadashi Abe, Masanori Moriwaki
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Patent number: 4617153Abstract: This invention deals with the use of a perfluorocarbon polymer oxidation catalyst consisting of a perfluorocarbon main chain and a side chain constructed from structural units of chromium (III) difluoromethylene sulfonate or cerium (IV) difluoromethylene sulfonate in a method of preparing a carbonyl compound through an oxidation of an alcohol.Type: GrantFiled: September 17, 1985Date of Patent: October 14, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventors: Hitosi Nozaki, Koichiro Oshima
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Patent number: 4606863Abstract: This invention provides a process for preparing carboxylic acid, the process comprising subjecting an oxidation product produced by reacting a peroxide with (a) unsaturated aliphatic monocarboxylic acid having at least one unsaturated bond in the carbon chain and containing 6 to 24 carbon atoms or its ester or (b) cyclic and/or acyclic aliphatic olefin having at least one unsaturated bond in the carbon chain to oxidation by oxygen or oxygen-containing gas in the presence of a catalyst comprising (i) at least one heavy metal compound and (ii) at least one member selected from the group consisting of a bromine compound and a chlorine compound.Type: GrantFiled: June 1, 1984Date of Patent: August 19, 1986Assignee: New Japan Chemical Co., Ltd.Inventors: Mikio Nakazawa, Kango Fujitani, Hiroshi Manami
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Patent number: 4550196Abstract: This invention relates to a process for preparing monocarboxylic or dicarboxylic acids by means of an oxidative scission of vicinal diols with H.sub.2 O.sub.2. One starts from vicinal, either terminal or internal, diols soluble in water and, if desired, carrying functional groups that are inert under the reaction conditions. The vicinal diols are reacted in an aqueous solution with H.sub.2 O.sub.2 at a temperature between 0.degree. and 120.degree. C., and at a pH value between 0.5 and 4, in the presence of a catalytic system consisting of tungstic acid or an alkali metal tungstate, and possibly of phosphoric or arsenic acid or an alkali metal salt thereof.Type: GrantFiled: April 12, 1984Date of Patent: October 29, 1985Assignee: Montedison S.p.A.Inventors: Carlo Venturello, Marco Ricci
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Patent number: 4546203Abstract: .beta.-Hydroxy-.beta.-methylglutaric acid is prepared by treating 3-methyl-1,3,5-pentanetriol in aqueous media with a permanganate salt.Type: GrantFiled: March 12, 1984Date of Patent: October 8, 1985Assignee: American Hoechst CorporationInventor: Ernest K. Metzner
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Patent number: 4533750Abstract: A process for isolating methacrylic acid by solvent extraction from an aqueous methacrylic acid solution obtained from a gas phase catalytic oxidation reaction, characterized in that the aqueous methacrylic acid solution is previously first contacted with an extraction solvent, polymers precipitated out from the aqueous methacrylic acid solution are removed and the remainder is fed into an extraction column.Type: GrantFiled: July 17, 1980Date of Patent: August 6, 1985Assignee: Mitsubishi Rayon Co. Ltd.Inventors: Hiroshi Matsumura, Masato Otani, Fumiki Murakami
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Patent number: 4532079Abstract: Process for the preparation of a monocarboxylic or dicarboxylic acid by oxidative scission of an olefine or its corresponding vicinal dihydroxy compound.An olefine of the formula R.sub.1 --CH.dbd.CH--R.sub.2 or R.sub.1 --CH.dbd.CH.sub.2 or a vicinal dihydroxy compound of formula R.sub.1 --CHOH--CHOH--R.sub.2 or R.sub.1 --CHOH--CH.sub.2 OH (wherein R.sub.1 and R.sub.2 are either equal to or different from each other, and possibly substituted with groups inert under the reaction conditions, represent hydrocarbon groups such as the alkyls having up to 30 carbon atoms; the cycloalkyls, possibly branched or substituted and having from 3 to 12 carbon atoms; the aryls and alkylaryls having from 6 to 12 carbon atoms; moreover, R.sub.1 and R.sub.2 may be bound to each other so as to form a cyclic alkenyl or cycloalkyl having up to 12 carbon atoms) are reacted, with vigorous stirring, with H.sub.2 O.sub.2, at a temperature between 0.degree. and 120.degree. C.Type: GrantFiled: April 12, 1984Date of Patent: July 30, 1985Assignee: Montedison S.p.A.Inventors: Carlo Venturello, Marco Ricci
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Patent number: 4421611Abstract: A new acetylenic composition, 3-(2-propynoxy)-2-propenoic acid, and its methods of preparation are described. Also, acetylenic compositions are described which are prepared by the process which comprises the steps of(a) reacting propargyl alcohol with an alkali metal permanganate in an aqueous alkaline solution,(b) filtering the reaction mixture, and(c) acidifying the filtrate with acid.The acetylenic compositions prepared in this manner are useful in aqueous acidic plating baths for the electrodeposition of a bright nickel or nickel-iron alloy on a substrate. Methods for the electrodeposition of nickel and nickel-iron alloys from such baths as well as additive compositions for forming the baths are described.Type: GrantFiled: September 30, 1982Date of Patent: December 20, 1983Assignee: McGean-Rohco, Inc.Inventor: James C. Cameron
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Patent number: 4404397Abstract: A stabilized heteropoly molybdate catalyst precursor in calcined form and containing anionic molybdenum in defect state is surface impregnated with certain metal cations. The stabilized precursor is one obtained by incorporating into the reaction product of a molybdate and a soluble phosphate, silicate or arsenate, an aqueous chloride ion and a compound of phosphotungstate, silicotungstate, vanadium arsenate, silico-arsenate, phosphovanadate, or silicovanadate, followed by drying and calcining. During the chloride ion stabilization step other metals may be optionally incorporated in forming the stabilized precursor.The obtained precursor is catalytically active in the conversion of the unsaturated aldehydes to the corresponding unsaturated carboxylic acids with or without incorporation of the metal cation during the chloride ion stabilization step.Type: GrantFiled: December 29, 1980Date of Patent: September 13, 1983Assignee: Air Products and Chemicals, Inc.Inventor: Chelliah Daniel
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Patent number: 4380664Abstract: At least one olefinic hydrocarbon of 3 to 4 carbon atoms is oxidized catalytically in the gas phase in the presence of molecular oxygen at 200.degree.-450.degree. C. to produce the corresponding aldehyde and acid over a calcined catalyst of the formula Mo.sub.a Sb.sub.b Bi.sub.c Fe.sub.d Ni.sub.e Sn.sub.f X.sub.g Y.sub.h O.sub.i wherein X is at least one alkali metal selected from the group consisting of potassium, rubidium and cesium; Y is at least one metal selected from the group consisting of cobalt, uranium, germanium, tungsten and titanium; a to h are atomic ratios wherein a=12, b=0.2 to 20, c=0.2 to 12, d=0.2 to 12, e=0.2 to 12, f=0 to 20, g=0.01 to 4 and h=0 to 6; and i is determined according to the oxidation states of the metal atoms in the catalyst.Type: GrantFiled: March 29, 1978Date of Patent: April 19, 1983Assignee: Mitsubishi Rayon Company, Ltd.Inventors: Hiromichi Ishii, Hideo Matsuzawa, Masao Kobayashi, Kantaro Yamada
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Patent number: 4348509Abstract: Alkoxyalkanols are oxidized to the corresponding alkoxyalkanoic acids by contacting the alkanols with oxygen in the presence of a catalyst comprising platinum supported on a macroreticular cross-linked polystyrene/divinylbenzene resin. Enhanced rates are obtained.Type: GrantFiled: July 6, 1981Date of Patent: September 7, 1982Assignee: Shell Oil CompanyInventors: Andrea Sanders, Leo Kim
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Patent number: 4339394Abstract: Certain multiply promoted Sn-Sb oxides are superior catalysts for the ammoxidation of olefins to the corresponding unsaturated nitriles, the selective oxidation of olefins to unsaturated aldehydes and acids, and the oxydehydrogenation of olefins to diolefins.Type: GrantFiled: October 1, 1980Date of Patent: July 13, 1982Assignee: The Standard Oil Co.Inventors: Robert K. Grasselli, Dev D. Suresh, James F. Brazdil, Frances I. Ratka
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Patent number: 4323520Abstract: The present invention relates to a process for the conversion of tertiary-butyl-containing compounds to methacrylic derivatives, and more particularly to a process for the conversion of tertiary-butyl-containing compounds selected from the group consisting of alkyl tertiary-butyl ethers, tertiary-butyl alcohol, isobutylene dimer (2,2,4-trimethylpentene) and isobutylene trimer, to methacrolein, methacrylic acid or methacrylonitrile.Type: GrantFiled: May 9, 1977Date of Patent: April 6, 1982Assignee: The Standard Oil Co.Inventors: Harley F. Hardman, James L. Callahan, Robert K. Grasselli
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Patent number: 4321407Abstract: Process for reducing the color forming tendency of alkanedioic acid esters by contact with an alkali metal borohydride in the presence of water.Type: GrantFiled: July 17, 1980Date of Patent: March 23, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventor: Robert A. Smiley
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Patent number: 4319043Abstract: The invention relates to the production of oxygenated organic compounds comprising alcohols, aldehydes, ethers and salts of carboxylic acids. Prior art processes for the production of ethanol in particular involve the use of elevated temperatures and pressures. Milder conditions can be used in the process of the invention in which either a mercury compound of formula (R.sup.1 OCHR.sup.2 CHR.sup.3 Hg).sub.n X (I), wherein X is an organic or inorganic anion, n is an integer equal to the valency of the anion, R.sup.2 and R.sup.3 are independently a hydrogen atom or an alkyl group and R.sup.1 is a hydrogen atom, an alkyl group or the group --(--CHR.sup.2 CHR.sup.3 Hg).sub.n X, or the precursors of the compound (I), with a catalyst comprising a complex containing a metal of Group VIII, particularly rhodium, in the presence of a liquid reagent containing an active acidic hydrogen atom. A particularly suitable rhodium complex is one having the formula:[Rh(C.sub.5 Me.sub.5).sub.2 (OH).sub.3 ]Cl.xH.sub.Type: GrantFiled: March 26, 1980Date of Patent: March 9, 1982Assignees: University of Sheffield, BP Chemicals LimitedInventors: John Cook, Peter M. Maitlis
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Patent number: 4256916Abstract: Polyethylene glycols of the typeHOCH.sub.2 CH.sub.2 O(CH.sub.2 CH.sub.2 O).sub.n CH.sub.2 CH.sub.2 OHwherein n is an integer of from 0 to 5, can be converted to the corresponding dicarboxylic acids of the formulaHOOCCH.sub.2 O(CH.sub.2 CH.sub.2 O).sub.n CH.sub.2 COOHwherein n is as previously defined, by oxidation in an aqueous solution over a fixed bed catalyst consisting of platinum on a granular carbon support.Type: GrantFiled: August 15, 1979Date of Patent: March 17, 1981Assignee: Eastman Kodak CompanyInventors: Don L. Morris, William J. Gammans, Jerry D. Holmes
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Patent number: 4250339Abstract: Methacrolein is produced by a vapor phase oxidation of isobutylene or tertiary butanol in the presence of a complex oxide catalyst having the formulaMo.sub.a Co.sub.b Fe.sub.c Bi.sub.d Tl.sub.e X.sub.f Y.sub.g Z.sub.h O.sub.iwherein X represents V and/or Nb; Y represents La and/or Ce; and Z represents Cs and/or Te and a, b, c, d, e, f, g, h and i represent atomic ratios wherein a=12; b=3 to 15; c=0.4 to 5; d=0.4 to 5; e=0.01 to 2; f=0.01 to 2; g=0 to 2; h=0 to 2; and i is determined by the valences of the non-oxygen components of the catalyst and is usually in a range of 40 to 79.Type: GrantFiled: November 30, 1979Date of Patent: February 10, 1981Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Teruhisa Sakamoto, Kazuhiko Sekizawa, Keiichi Kihara
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Patent number: 4230887Abstract: C.sub.2 -C.sub.6 monocarboxylic and dicarboxylic acids are scrubbed from gas phase mixtures of such acids and water by gas absorption techniques utilizing a liquid solvent comprising a polyoxyalkylene glycol or a monoalkyl or dialkyl ether thereof. The solvent enriched with the acid is subjected to distillation to recover a substantially anhydrous acid product.Type: GrantFiled: February 16, 1978Date of Patent: October 28, 1980Assignee: Celanese CorporationInventors: William T. Mitchell, Phillip S. Snyder
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Patent number: 4225694Abstract: Primary and secondary unsaturated alcohols are converted to their corresponding aldehydes and/or carboxylic acids and ketones respectively with alkali metal (per) halate, preferably sodium periodate, in the presence of ruthenium catalyst. The process is particularly useful in the oxidation of chrysanthemyl alcohol. Any unconverted intermediate aldehyde formed may be converted to the acid by recycling or by a separate oxidation step.Type: GrantFiled: September 6, 1977Date of Patent: September 30, 1980Assignee: Air Products and Chemicals, Inc.Inventors: Augustine I. Dalton, Jr., Henry J. Doran, Robert D. H. Murray
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Patent number: 4220803Abstract: A process for producing acetic acid and acetaldehyde from ethanol which comprises contacting a mixture of ethanol and oxygen with a supported copper oxide catalyst essentially free of barium, the mole ratio of oxygen to ethanol being from about 0.1 to about 0.5.Type: GrantFiled: June 27, 1978Date of Patent: September 2, 1980Assignee: Union Carbide CorporationInventors: Arthur E. Marcinkowsky, Joseph P. Henry
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Patent number: 4214101Abstract: A process for preparing ether carboxylates which comprises contacting an ethoxylated alcohol or alkylphenol or an ethylene oxide/propylene oxide block copolymer, with oxygen, in the presence of a palladium catalyst, at a pH of from 8 to 13 and at a temperature of 50.degree. to 95.degree. C.Type: GrantFiled: April 13, 1978Date of Patent: July 22, 1980Assignee: Kao Soap Co., Ltd.Inventors: Bunji Miya, Akio Kimura
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Patent number: 4126748Abstract: In an improved process for the production of carboxylic acid esters by catalytic oxidation of alcohols in the liquid phase, primary alcohols of 1-4 carbon atoms are oxidized with molecular oxygen at temperatures of about 100.degree.-250.degree. C. in the presence of catalytic amounts of a compound of Co, Mn, Cr, or Fe, and an acid having a first dissociation constant K.sub.1 greater than 10.sup.-3, dissolved in the reaction mixture.Type: GrantFiled: March 25, 1977Date of Patent: November 21, 1978Assignee: Chemische Werke Huels, A.G.Inventors: Bernhard Scholz, Fritz Obenaus, Gerhard Franz, Hans-Jurgen Erberich, Heinz-Otto Reitemeyer
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Patent number: 4111984Abstract: At least one compound from the group of unsaturated hydrocarbons of three to four carbon atoms and t-butyl alcohol is oxidized catalytically in the gas phase in the presence of molecular oxygen at 200.degree.-450.degree. C to produce the corresponding aldehyde or acid over a calcined catalyst of the formula Mo.sub.a Sb.sub.b Bi.sub.c Fe.sub.d Ni.sub.e Sn.sub.f X.sub.g Y.sub.h O.sub.i wherein X is at least one of potassium, rubidium or cesium, Y is at least one of cobalt, uranium, germanium, tungsten or titanium, a to h are atomic ratios wherein a=12, b=0.2 to 20, c=0.2 to 12, d=0.2 to 12, e=0.2 to 12, f=0 to 20, g=0.01 to 4 and h=0 to 6 and i is a value determined by the oxidation state of the metal atoms in the catalyst.An embodiment of the calcined catalyst of the invention has the formula Mo.sub.a Sb.sub.b Bi.sub.c Fe.sub.d Ni.sub.e Sn.sub.f X.sub.g Y.sub.h Z.sub.j O.sub.i wherein X and y are as defined above and Z is palladium and a to j are atomic ratios wherein a=12, b=0.2 to 20, c=0.2 to 12, d=0.Type: GrantFiled: March 16, 1976Date of Patent: September 5, 1978Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Hiromichi Ishii, Hideo Matsuzawa, Masao Kobayashi, Kantaro Yamada