Preparing From A Peroxide Or Preparing By Oxidation Patents (Class 568/815)
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Patent number: 4551553Abstract: The process of decomposing a hydroperoxide by contacting the hydroperoxide with a catalytic quantity of a catalyst system comprised of chromium and ruthenium. The catalyst system is characterized by its high stability while exhibiting improved activity for hydroperoxide decomposition and selectivity to desired alcohol and ketone products.Type: GrantFiled: February 22, 1983Date of Patent: November 5, 1985Assignee: Atlantic Richfield CompanyInventors: Paul D. Taylor, Michael T. Mocella
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Patent number: 4493801Abstract: Tertiary alcohols are prepared by oxidizing tertiary aldehydes with oxygen at elevated temperatures.The tertiary alcohols prepared in this way are valuable and versatile intermediates for dyes, drugs and crop protection agents and are used, for example, in the preparation of agrochemicals.Type: GrantFiled: November 2, 1981Date of Patent: January 15, 1985Assignee: BASF AktiengesellschaftInventors: Franz Merger, Gerhard Nestler
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Patent number: 4408077Abstract: A process and intermediates for preparing 6-(lower alkoxy)-5-(trifluoromethyl)-1-naphthalenecarboxylic acid derivatives are disclosed. The derivatives are useful for preparing aldose reductase inhibitors. With reference to the process, 1,1,1-trifluoro-5-(2-methylphenyl)-2,3-pentadione 3-oxime is cyclized to give a key intermediate 3,4-dihydro-1-hydroxy-5-methyl-1-(trifluoromethyl)-2(1H)-naphthalenone oxime; and 3,4-dihydro-1-hydroxy-5-methyl-1-(trifluoromethyl)-2(1H)-naphthalenone is aromatized to 5-methyl-1-(trifluoromethyl)-2-naphthalenol with a dehydrating agent.Type: GrantFiled: November 13, 1981Date of Patent: October 4, 1983Assignee: Ayerst, McKeena & Harrison, Inc.Inventors: Kazimir Sestanj, Steven Fung, Nedumparambil A. Abraham, Francesco Bellini
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Patent number: 4400558Abstract: The present invention provides a novel method for recovering 2-phenylethanol which is produced as a by-product of non-catalytic air oxidation of ethylbenzene, and as a by-product, in the ethylbenzene hydroperoxide epoxidation of an olefinically unsaturated compound, e.g., propylene, to the corresponding alkylene oxide, e.g., propylene oxide. In such processes, 2-phenylethanol accumulates in a process stream typically comprising major proportions of methylbenzyl alcohol, ethylbenzene, alkylene oxide and acetophenone. Conventional distillation-separation procedures may remove most of the alkylene oxide and ethylbenzene, leaving a process stream which is eventually used for styrene monomer production which contains minor amounts, i.e., less than about 20 weight percent, of 2-phenylethanol.Type: GrantFiled: April 17, 1981Date of Patent: August 23, 1983Assignee: Atlantic Richfield CompanyInventors: Margaret I. Nemet-Mavrodin, John F. White
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Patent number: 4322567Abstract: In a process for producing an aromatic alcohol by catalytic hydrogenation of at least one tertiary peroxide selected from the group consisting of tertiary aromatic hydroperoxides and tertiary aromatic peroxides in the presence of a palladium catalyst in a lower aliphatic alcohol solvent to form the corresponding alcohol; the improvement wherein said catalyst has a palladium metal surface area, determined by the CO chemisorption method, of up to about 200 m.sup.2 /g.multidot.Pd.Type: GrantFiled: May 22, 1980Date of Patent: March 30, 1982Assignee: Mitsui Petrochemical Industries Ltd.Inventors: Fujihisa Matsunaga, Norio Ohno, Hirohiko Nambu
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Patent number: 4308408Abstract: Styrene or styrene substituted in the aromatic nucleus or on the vinyl group with a methyl group or styrene having the vinyl group substituted by hydroxymethyl is reacted with less than 2 moles of formic acid and less than 2 moles of hydrogen peroxide per mole of styrene or substituted styrene to hydroxylate the double bond. The formic acid is employed at a concentration between 20 and 100 weight percent and the hydrogen peroxide is employed at a concentration of less than 50 weight %. The concentration of the hydrogen peroxide in the aqueous phase of the reaction mixture is held below 15 weight percent during the entire reaction.The corresponding diols or triols are formed directly from the olefins employed within reasonable reaction times in high yields.Type: GrantFiled: September 16, 1980Date of Patent: December 29, 1981Assignee: Degussa AktiengesellschaftInventors: Gerhard Kabisch, Horst Malitius, Siegfried Raupach, Rudolf Trube, Hans Wittmann
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Patent number: 4308409Abstract: Propylene is converted to propylene glycol at high selectivity in a process in which ethylbenzene hydroperoxide and water are reacted with propylene in the presence of osmium tetroxide catalyst and a base at a pH of about 14.Type: GrantFiled: July 28, 1980Date of Patent: December 29, 1981Assignee: Gulf Research & Development CompanyInventors: Ching-Yong Wu, Thaddeus P. Kobylinski, John E. Bozik
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Patent number: 4271091Abstract: Cyclohexanone and/or cyclohexanol can be oxidized in the vapor phase to phenol by contacting the cyclohexanone and/or cyclohexanol with a suitable oxidation catalyst in the presence of molecular oxygen. Suitable catalysts are solids comprising Mo, W, Sb and/or V oxides or complexes thereof. The catalysts may be promoted with additional elements.Type: GrantFiled: June 17, 1978Date of Patent: June 2, 1981Assignee: Standard Oil CompanyInventors: Robert K. Grasselli, Dev D. Suresh
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Patent number: 4255596Abstract: Ethylene is converted to ethylene glycol at high selectivity in a process in which ethylbenzene hydroperoxide and water are reacted with ethylene in the presence of osmium tetroxide catalyst and a base at a pH of about 14.Type: GrantFiled: February 25, 1980Date of Patent: March 10, 1981Assignee: Gulf Research & Development CompanyInventors: Ching-Yong Wu, Thaddeus P. Kobylinski, John E. Bozik
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Patent number: 4246203Abstract: The invention relates to a process in which an aromatic hydroperoxide of formula: ##STR1## wherein independently R.sub.1 is methyl or ethyl, R.sub.2 is hydrogen, methyl or ethyl, or where R.sub.1 and R.sub.2 together form an alicyclic ring of 5 or 6 carbon atoms, R.sub.3 is hydrogen or alkyl and R.sub.4 and R.sub.5 are hydrogen, alkyl or together form an automatic ring, n is 0, 1 or 2 and n.sup.1 is 1 or 2, is converted to a phenol and a carbonyl compound in a catalyzed cleavage decomposition reaction. In particular cumene hydroperoxide is converted to phenol and acetone. Instead of removing the decomposition products from the reactor in the liquid phase and dissipating the reaction heat as in prior art processes the heat is used to remove the phenol and the carbonyl compound in the vapor phase leaving a liquid residue of higher-boiling compounds and catalyst in the case where a liquid cleavage catalyst is employed.Type: GrantFiled: August 9, 1979Date of Patent: January 20, 1981Assignee: BP Chemicals LimitedInventor: Max M. Wirth
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Patent number: 4208352Abstract: A process is provided for oxygenating alkyl-substituted aromatic compounds. Alkyl-substituted aromatic compounds in the liquid phase are contacted with molecular oxygen at a temperature below 200.degree. C. in the presence of a catalyst system which is substantially insoluble in the reaction mixture at reaction conditions. The catalyst components are a suspended copper compound and a suspended bromine compound which preferably are associated with a major quantity of a suitable catalyst support material. Optionally, the reaction can be carried out in the presence of minor amounts of acetic acid, acetic anhydride or suitable inorganic nitrate compounds.Type: GrantFiled: December 15, 1975Date of Patent: June 17, 1980Assignee: Phillips Petroleum CompanyInventor: Lloyd E. Gardner
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Patent number: 4203926Abstract: Ethylbenzene hydroperoxide and ethylene or propylene are converted to acetophenone, 1-phenylethanol and the corresponding glycol at high selectivity in a process in which ethylbenzene hydroperoxide is reacted with the olefin in a two-phase liquid, organic-aqueous reaction system in the presence of osmium tetroxide and cesium, rubidium or potassium hydroxide.Type: GrantFiled: December 18, 1978Date of Patent: May 20, 1980Assignee: Gulf Research & Development CompanyInventors: Ching-Yong Wu, Thaddeus P. Kobylinski
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Patent number: 4191839Abstract: A highly selective, one-step conversion of toluene to benzylidene diacetate is provided by the reaction of toluene with O.sub.2 and acetic anhydride in the presence of an acid catalyst. No metal catalysts are required.Type: GrantFiled: March 27, 1978Date of Patent: March 4, 1980Assignee: Suntech, Inc.Inventors: James E. Lyons, Robert W. Shinn, George Suld
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Patent number: 4151213Abstract: This invention relates to a new catalyst and to a novel oxidation process. In this novel process, aromatic compounds with an alkyl group having at least one alpha hydrogen, including aromatic compounds wherein the alkyl groups are unsubstituted and substituted, are contacted in the liquid phase at reaction conditions with an oxygen-containing gas in the presence of a novel catalyst which is prepared by milling an anhydrous transition metal halide with silver nitrite, the transition metal being selected from the Groups IVb to VIII and IIb of the Periodic Table, wherein the mole ratios of metal halide to silver nitrite are in the ratio of 1:1 to 1:5.Type: GrantFiled: January 21, 1977Date of Patent: April 24, 1979Assignee: Standard Oil Company (Indiana)Inventor: Ellis K. Fields
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Patent number: 4088823Abstract: A process is provided for oxygenating alkyl-substituted aromatic compounds. In the process alkyl-substituted aromatic compounds are contacted with molecular oxygen in the presence of a suitable monocarboxylic acid, a soluble copper, cobalt, or iron compound, and an inorganic bromine compound. Optionally present are inorganic nitrates, acetic anhydride, or water. In an embodiment of the invention the process is carried out in two distinct steps with contact of the alkyl-substituted aromatic compounds and oxygen in the presence of the essential components produce an ester comprising both an aromatic alcohol and the carboxylic acid with subsequent hydrolyzing of this ester to produce an aromatic alcohol with regeneration of the carboxylic acid.Type: GrantFiled: October 7, 1975Date of Patent: May 9, 1978Assignee: Phillips Petroleum CompanyInventors: Hans D. Holtz, Lloyd E. Gardner