Preparing By Oxidation Utilizing Gaseous Oxygen Patents (Class 568/565)
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Patent number: 8575398Abstract: The purpose of the present invention is to provide an advantageous non-barbotage method for oxidation of hydrocarbons, that, when implemented in various embodiments thereof, provides significantly higher selectivity, a greater level of safety, lower capital costs, etc., than conventional oxidation processes utilizing the barbotage technique. The essence of the inventive non-barbotage oxidation process is ensuring that the oxidizing agent delivered to the process reactor undergoes continued contact only with exposed surfaces of the liquid phase of the hydrocarbons being oxidized configured as at least one of: formed liquid phase thin film(s), liquid phase continuous stream(s), and/or liquid phase globule (e.g., droplets, etc.Type: GrantFiled: October 29, 2010Date of Patent: November 5, 2013Assignee: Illa International, LLCInventor: Vladimir Mikhailovitch Zakoshansky
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Patent number: 8128886Abstract: A reactor which comprises a vessel (1) with a vessel bottom (2), a stirrer (3) arranged in the vessel, an emergency discharge valve (4) arranged in the vessel bottom for emptying the reactor in less than 600 seconds and at least one filtration device (5) arranged in the vessel bottom is suitable for the safe preparation of organic peroxides. The process for preparing an organic peroxide comprises the steps of preparing a solid hydroperoxide in the form of a suspension in the reactor, filtering the suspension through the filtration device (5) arranged in the vessel bottom (2) while retaining the solid hydroperoxide in the reactor and reacting the hydroperoxide with an alkylating agent, an acylating agent or a carbonyl compound.Type: GrantFiled: July 18, 2006Date of Patent: March 6, 2012Assignee: United Initiators GmbH & Co. KGInventors: Hans Appel, Joseph Weinmaier
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Publication number: 20110319668Abstract: The purpose of the present invention is to provide an advantageous non-barbotage method for oxidation of hydrocarbons, that, when implemented in various embodiments thereof, provides significantly higher selectivity, a greater level of safety, lower capital costs, etc., than conventional oxidation processes utilizing the barbotage technique. The essence of the inventive non-barbotage oxidation process is ensuring that the oxidizing agent delivered to the process reactor undergoes continued contact only with exposed surfaces of the liquid phase of the hydrocarbons being oxidized configured as at least one of: formed liquid phase thin film(s), liquid phase continuous stream(s), and/or liquid phase globule (e.g., droplets, etc.Type: ApplicationFiled: October 29, 2010Publication date: December 29, 2011Applicant: ILLA INTERNATIONAL, LLC.Inventor: Vladimir Mikhailovitch Zakoshansky
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Patent number: 7446232Abstract: In a process for oxidizing alkylaromatic compounds to the corresponding hydroperoxide, an alkylaromatic compound of general formula (I): in which R1 and R2 each independently represents an alkyl group having from 1 to 4 carbon atoms, provided that R1 and R2 may be joined to form a cyclic group having from 4 to 10 carbon atoms, said cyclic group being optionally substituted, and R3 represents hydrogen, one or more alkyl groups having from 1 to 4 carbon atoms or a cyclohexyl group, with oxygen in the presence of an added catalyst comprising tert-butyl hydroperoxide and in the absence of any other catalyst, to produce a hydroperoxide of general formula (II): in which R1, R2 and R3 have the same meaning as in formula (I). The hydroperoxide may then be converted into a phenol and a ketone of the general formula R1COCH2R2 (III), in which R1 and R2 have the same meaning as in formula (I).Type: GrantFiled: July 13, 2007Date of Patent: November 4, 2008Assignee: ExxonMobil Chemical Patents Inc.Inventors: Jihad Mohammed Dakka, Doron Levin, John Scott Buchanan, Jon Edmond Randolph Stanat
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Patent number: 7038089Abstract: The invention relates to a process for preparing hydroperoxides from their corresponding hydrocarbons which comprises oxidizing said hydrocarbons, particularly ethylbenzene, with an oxygen containing gas in the presence of a catalyst comprising a cyclic imide compound and a compound selected from the group consisting of an alkali metal compound or mixture thereof.Type: GrantFiled: January 22, 2004Date of Patent: May 2, 2006Assignee: Respol Quimica, S.A.Inventors: Pilar De Frutos Escrig, Pedro Pablo Toribio Temprado, Raul Martos Calvente, Jose Miguel Campos Martin, Jose Luis Garcia Fierro
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Patent number: 6888034Abstract: Process for oxidizing cyclohexane in which oxygen is contacted with cyclohexane at a pre-selected feed rate in a first reaction zone and unconsumed oxygen is contacted with cyclohexane in a second reaction zone in which the cyclohexane feed rate is lower than the pre-selected feed rate.Type: GrantFiled: November 5, 2003Date of Patent: May 3, 2005Assignee: Invista North America S.A.R.L.Inventors: David Paul Landray, Ludovic Rick Fodor, Bruce Edwin Murphree, James Marvin Rung
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Patent number: 6028193Abstract: A method for producing aryl alkyl hydroperoxides which comprises selectively oxidizing an aryl alkyl hydrocarbon having the formula: ##STR1## wherein P and Q are hydrogen or an alkyl and may be the same or different from each other; x is an integer of 1-3; and Ar is an aromatic hydrocarbon group having a valence of x, with an oxygen-containing gas in the presence of a transition metal complex which contains, as a ligand, a cyclic polyfunctional amine compound having at least three nitrogen atoms in the ring forming molecular chain or an open chain polyfunctional amine compound having at least three nitrogen atoms in the main chain of the molecule.Type: GrantFiled: April 15, 1999Date of Patent: February 22, 2000Assignee: Mitsui Chemicals, Inc.Inventors: Terunori Fujita, Shigekazu Matsui, Toshihiro Takai, Hideto Matsuoka, Akifumi Kagayama, Hiroshi Kuroda, Masayasu Ishibashi, Hiroshi Iwasaki, Nobuya Hirokane
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Patent number: 5744651Abstract: Tetrafluoroethylene oxidation process at temperatures comprised between -100.degree. C. and -40.degree. C., in absence of Uv radiations, and by operating in the presence of a chemical initiator containing at least one F--X bond, wherein X is oxygen or halogen, in the presence of a solvent comprising an amount of COF.sub.2 higher than 8% by moles.Type: GrantFiled: February 13, 1997Date of Patent: April 28, 1998Assignee: Ausimont S.p.A.Inventors: Giuseppe Marchionni, Pier Antonio Guarda
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Patent number: 5196598Abstract: A process for producing a polyhydroperoxy aromatic compound by oxidation of an aromatic hydrocarbon, e.g., 4,4'-diisopropylbiphenyl and 4,4'-diisopropylnaphthalene, with molecular oxygen is disclosed, in which the oxidation is carried out in the presence of a metal ion selected from cobalt, nickel, zinc and lead ions. Even in using a reaction apparatus made of an iron-containing metal generally employed in industry, a high conversion of secondary alkyl groups can be reached, and the desired polyhydroperoxy aromatic compound can be obtained in a high yield.Type: GrantFiled: October 18, 1991Date of Patent: March 23, 1993Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Hiroshi Iwane, Takahiro Sugawara, Naoki Suzuki, Kimiko Kaneko
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Patent number: 5196597Abstract: The present invention relates to a process for the oxidation of isobutane in the liquid phase to produce TBA and TBHP wherein at least a portion of the oxidation product mixture is obtained from the condensate of vapors from the oxidation zone.Type: GrantFiled: April 22, 1992Date of Patent: March 23, 1993Assignee: Arco Chemical Technology, L.P.Inventors: Robert N. Cochran, Shaw-Chan Lin
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Patent number: 5017729Abstract: Phenol is produced in a recycle manner by (a) reacting benzene with propylene to synthesize cumene, (b) oxidizing the cumene of step (a) into cumene hydroperoxide, (c) acid cleaving cumene hydroperoxide into phenol and acetone, (d) hydrogenating the acetone of step (c) into isopropanol, (e) dehydrating the isopropanol of step (d) into propylene, and (f) recycling the propylene of step (e) to step (a). It is also possible to take propylene from step (e). The acetone by-product produced upon preparation of phenol is converted into propylene which is useful by itself for any other uses or recycled to the phenol producing process.Type: GrantFiled: September 5, 1989Date of Patent: May 21, 1991Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Hiroshi Fukuhara, Fujihisa Matsunaga
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Patent number: 4996372Abstract: In a process for producing 2,6-dihydroxynaphthalene from 2,6-diisopropylnaphthalene, 2,6-diisopropylnaphthalene is oxidized in the presence of a specific proportion of a basic compound to hydroxylate or hydroperoxylate 2,6-diisopropylnaphthalene in a high conversion, and the resulting intermediate is then subjected to acid cleavage in the presence of hydrogen peroxide to produce 2,6-dihydroxynaphthalene in a high yield. The yield of 2,6-dihydroxynaphthalene increases by subjecting the reaction mixture containing the above intermediate to a purifying operation or dehydrating operation or adding acetone to it before it is submitted to the acid cleavage. 2,6-Dihydroxynaphthalene may be reacted with acetic anhydride to obtain 2,6-diacetoxynaphthalene.Type: GrantFiled: February 2, 1990Date of Patent: February 26, 1991Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Kenji Saeki, Hiroshi Fukuhara, Tokinori Agoo, Toru Taguchi, Hisaya Miki, Yutaka Haneda, Sadao Yoshimoto
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Patent number: 4935551Abstract: m-Diisopropylbenzene dihydroperoxide is produced in good yield in a continuous process by the oxidation of diisopropylbenzene, comprised of major amounts of the m-isomer and less than 6% of the o-isomer, under anhydrous, non-alkaline conditions with oxygen or air at about 85.degree. C.-95.degree. C.Type: GrantFiled: December 22, 1987Date of Patent: June 19, 1990Assignee: Indspec Chemical CorporationInventor: Ching-Yong Wu
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Patent number: 4906790Abstract: A method of oxidizing secondary alkyl substituted naphthalenes with molecular oxygen in a liquid phase to hydroperoxides, carbinols or mixtures of these, which comprises: oxidizing the secondary alkyl substituted naphthalenes in the presence of an aromatic hydrocarbon having a fused ring which contains at least one methylene group therein in amounts of not more than about 1000 ppm based on the secondary alkyl substituted napththalene used.A process of producing isopropylnaphthols is also disclosed, which comprises: oxidizing diisopropylnaphthalenes with molecular oxygen in a liquid phase to diisopropylnaphthalene monohydroperoxides in the presence of (a) either an aromatic hydrocarbon having a fused ring which contains at least one methylene group therein, or a paladium catalyst soluble in the reaction mixture, and (b) an organic polar compound such as acetonitrile; and then acid-decomposing the diisopropylnaphthalene monohydroperoxide to the isopropylnaphthol.Type: GrantFiled: September 9, 1988Date of Patent: March 6, 1990Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Masaharu Ishiguro, Hisaya Miki, Nobuya Hirokane
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Patent number: 4709088Abstract: A process for producing 2,6-naphthalenedicarboxylic acid which comprises oxidizing 2,6-diisopropylnaphthalene or its oxidation product as a starting material with molecular oxygen in a reaction medium containing at least 50% by weight of an aliphatic monocarboxylic acid having not more than 3 carbon atoms in the presence of an oxidation catalyst comprising (A) at least one heavy metal element selected from the group consisting of cobalt and manganese, and (B) bromine element, the 2,6-diisopropylnaphthalene and/or its oxidation product being used in a proportion of 0.1 to 5 moles per gram-atom of the heavy metal element of the oxidation catalyst.Type: GrantFiled: July 15, 1986Date of Patent: November 24, 1987Assignee: Teijin Petrochemical Industries, Ltd.Inventors: Isao Hirose, Tamio Amemiya, Tokuji Sakai
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Patent number: 4579978Abstract: Substantially quantitative yields of bibenzyl hydroperoxide and bibenzyl dihydroperoxide can be obtained when oxygen is reacted with bibenzyl (1,2-diphenylethane) in the presence of a minor amount of sodium bicarbonate at a temperature within the range of about 100.degree. to about 160.degree. C. to provide an oxidation product wherein the bibenzyl is substantially selectively converted to the bibenzyl hydroperoxides. The bibenzyl hydroperoxides can be used as raw materials for the production of propylene oxide by reacting the bibenzyl hydroperoxides with propylene.Type: GrantFiled: November 13, 1984Date of Patent: April 1, 1986Assignee: Texaco Inc.Inventors: Jiang-Jen Lin, John R. Sanderson
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Patent number: 4455440Abstract: In a method for producing 1,3,5-triisopropylbenzene trihydroperoxides by bringing 1,3,5-triisopropylbenzene or its homologs into contact reaction with oxygen or an oxygen-containing gas in the co-existence of an aqueous alkali solution, a method for producing 1,3,5-triisopropylbenzene trihydroperoxides wherein said contact reaction is carried out under a condition that the reaction temperature be 60.degree. to 120.degree. C., the pH of the reaction solution phase be 8 to 11 and the amount of said aqueous alkali solution be 0.Type: GrantFiled: November 15, 1982Date of Patent: June 19, 1984Assignee: Sumitomo Chemical Company, LimitedInventors: Tsutomu Chiyoda, Makoto Nakamura, Shinichi Hasegawa
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Patent number: 4408082Abstract: In the direct oxidation of isobutane with molecular oxygen at moderate isobutane conversion levels (up to about 20%) in a reaction mixture maintained at a pressure greater than its critical pressure and at a temperature in the range from about 140.degree. C. to 170.degree. C., the selectivity of the isobutane conversion to tertiary-butyl hydroperoxide is enhanced with only minimal impact on the reaction rate by controlling the oxygen concentration in the reaction mixture at a level below about 0.1%M.Type: GrantFiled: October 5, 1981Date of Patent: October 4, 1983Assignee: Shell Oil CompanyInventor: Herman J. Baumgartner
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Patent number: 4408081Abstract: In continuous preparation of tertiary-butyl hydroperoxide by the direct oxidation of isobutane in dense-phase reaction mixture at a pressure in excess of the critical pressure of the mixture, and under conditions relating to temperature and to oxygen and isobutane content of the mixture, improvement in selectivity to TBHP is realized by a process which comprises conducting a plurality of such oxidation reactions each in one of a series of dense-phase reaction mixtures by continuously introducing isobutane reactant into the first reaction mixture in the series, continuously introducing oxygen reactant into each reaction mixture of the series, and withdrawing a continuous flow from each mixture of the series and introducing this flow into the next mixture of the series, with the provision that the continuous flow withdrawn from the last mixture of the series is taken from the process as a TBHP-containing product mixture characterized by a conversion of the isobutane reactant of between about 3 and 25 percent.Type: GrantFiled: October 5, 1981Date of Patent: October 4, 1983Assignee: Shell Oil CompanyInventor: Elton G. Foster
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Patent number: 4404406Abstract: In the preparation of tertiary-butyl hydroperoxide by the direct oxidation of isobutane, the production of tertiary-butyl hydroperoxide, expressed as the quantity of the compound prepared per unit of reactor volume per unit of time, is enhanced by conducting the oxidation in a dense, supercritical phase reaction mixture at a temperature in excess of the critical temperature of the mixture, at a pressure in excess of the critical pressure of the mixture, and under conditions relating to composition of the mixture.Type: GrantFiled: October 5, 1981Date of Patent: September 13, 1983Assignee: Shell Oil CompanyInventors: Eugene F. Lutz, Elton G. Foster
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Patent number: 4329514Abstract: Episodes of accelerated decomposition, or runaway, during the preparation of hydrocarbon hydroperoxides by reaction of hydrocarbons with molecular oxygen at elevated temperature, are brought under control through the addition to the oxidation reaction mixture of a small quantity of base in a substantially instantaneous manner at the onset of the runaway.Type: GrantFiled: January 19, 1981Date of Patent: May 11, 1982Assignee: Shell Oil CompanyInventors: Ludovicus B. J. O. van der Weijst, Enno B. De Vries, Gerard J. Heiszwolf
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Patent number: 4299991Abstract: Hydroperoxidizable hydrocarbons are hydroperoxidized by contacting them at hydroperoxidation conditions in the presence of a catalyst comprising a polymer containing maleimide linkages. For example, cumyl hydroperoxide can be produced by contacting cumene and oxygen with a catalyst comprising polymaleimide.Type: GrantFiled: December 28, 1979Date of Patent: November 10, 1981Assignee: The Standard Oil CompanyInventors: Louis J. Velenyi, Curtie E. Uebele, Serge R. Dolhyj
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Patent number: 4293719Abstract: Hydroperoxides, such as cyclohexylbenzene hydroperoxide, are manufactured by the oxidation of aryl compounds, such as cyclohexylbenzene, in the presence of a catalyst selected from the group consisting of C.sub.6 -C.sub.18 primary amines and polyvinylpyrrolidone.Type: GrantFiled: March 31, 1980Date of Patent: October 6, 1981Assignee: The Standard Oil CompanyInventors: Louis J. Velenyi, Serge R. Dolhyj, Marcia H. Sundeen
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Patent number: 4136123Abstract: Metallo phthalocyanines which have been rendered water soluble by substituting an alkali metal or alkaline earth metal sulfate or carboxylate salt onto the phthalocyanine structure have been found to be effective catalysts for the oxidation of aromatic compounds having benzylic carbon atoms to form the corresponding hydroperoxides.Type: GrantFiled: July 22, 1974Date of Patent: January 23, 1979Assignee: The Goodyear Tire & Rubber CompanyInventor: David A. Hutchings