Preparing By Oxidation Utilizing Gaseous Oxygen Patents (Class 568/577)
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Patent number: 8420867Abstract: Process for the preparation of hydroperoxides of alkylbenzenes characterized by the fact that the alkylbenzene reacts with oxygen in the presence of a catalytic system consisting of an N-hydroxyimide associated with a peroxide activator having a peracid or dioxyrane structure, possibly generated in situ.Type: GrantFiled: March 13, 2009Date of Patent: April 16, 2013Assignee: Polimeri Europa S.p.A.Inventors: Francesco Minisci, Carlo Punta, Francesco Recupero, Cristian Gambarotti, Raffaele Spaccini, Angelo Clerici, Alberto Clerici
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Patent number: 8334363Abstract: Oxidized and maleated compositions, such as oxidized and maleated tall oil compositions, can be prepared and used in a variety of industrial applications, including as emulsifiers and corrosion inhibitors.Type: GrantFiled: January 31, 2008Date of Patent: December 18, 2012Assignee: Georgia-Pacific Chemicals LLCInventors: Phillip W. Hurd, Gary D. Fultz, Brett A. Neumann, John B. Hines
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Publication number: 20110098509Abstract: The invention relates to a process for the preparation of phenol which comprises the aerobic oxidation of cumene to hydroperoxide with high conversions and selectivities, in the presence of new catalytic systems, extremely mild conditions and the subsequent acid decomposition of the hydroperoxide to phenol and acetone.Type: ApplicationFiled: September 20, 2007Publication date: April 28, 2011Applicant: POLIMERI EUROPA S.p.A.Inventors: Francesco Minisci, Ombretta Porta, Angelo Clerici, Alberto Clerici, Francesco Recupero, Carlo Punta, Cristian Gambarotti, Monica Pierini
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Patent number: 7335798Abstract: The specification provides a method of producing cumene hydroperoxide by continuous aqueous-emulsion oxidation at a high temperature and pressure in a cascade of reactors, wherein the process is conducted in the presence of a mixture of an aqueous solution of an ammonium salt with a concentration of 0.001–0.5 mass % and an aqueous solution of ammonia with a concentration of 0.001–0.5 mass %, which mixture is fed into each oxidation reactor in an ammonia:ammonium salt mass ratio of 1:100 to 100:1.Type: GrantFiled: July 6, 2005Date of Patent: February 26, 2008Assignee: General Electric CompanyInventors: Arkady Samuilovich Dyckman, John William Fulmer, Viktor Vladimirovich Pinson, Andrey Vladimirovich Zinenkov, Boris Issakovich Gorovits
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Patent number: 7141703Abstract: Improved processes for oxidizing alkylbenzene(s) to produce phenol and ketone product(s) using neutralizing base.Type: GrantFiled: January 21, 2004Date of Patent: November 28, 2006Assignee: Shell Oil CompanyInventors: Jiemin Yang, Jesse Raymond Black
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Patent number: 6956136Abstract: The specification provides a method of producing cumene hydroperoxide by continuous aqueous-emulsion oxidation at a high temperature and pressure in a cascade of reactors, wherein the process is conducted in the presence of a mixture of an aqueous solution of an ammonium salt with a concentration of 0.001-0.5 mass % and an aqueous solution of ammonia with a concentration of 0.001-0.5 mass %, which mixture is fed into each oxidation reactor in an ammonia:ammonium salt mass ratio of 1:100 to 100:1.Type: GrantFiled: July 29, 2003Date of Patent: October 18, 2005Assignee: General Electric CompanyInventors: Arkady Samuilovich Dyckman, John William Fulmer, Viktor Vladimirovich Pinson, Andrey Vladimirovich Zinenkov, Boris Issakovich Gorovits
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Patent number: 6956137Abstract: The invention relates to a method for oxidizing organic substrates using 1O2 in which hydrophobic organic substrates that react with 1O2 are added to an organic solvent in the presence of a heterogeneous or homogeneous catalyst with 30–70% being compr Afterwards, H2O2 is catalytically decomposed into water and 1O2, and the oxidation into corresponding oxidation products ensues.Type: GrantFiled: March 23, 2000Date of Patent: October 18, 2005Assignee: DSM Fine Chemicals Austria NFG GmbH & CO KGInventors: Jean-Marie Aubry, Veronique Rataj-Nardello, Paul Alsters
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Publication number: 20040162448Abstract: Improved processes for oxidizing alkylbenzene(s) to produce phenol and ketone product(s) using neutralizing base.Type: ApplicationFiled: January 21, 2004Publication date: August 19, 2004Inventors: Jiemin Yang, Jesse Raymond Black
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Publication number: 20040059162Abstract: The specification provides a method of producing cumene hydroperoxide by continuous aqueous-emulsion oxidation at a high temperature and pressure in a cascade of reactors, wherein the process is conducted in the presence of a mixture of an aqueous solution of an ammonium salt with a concentration of 0.001-0.5 mass % and an aqueous solution of ammonia with a concentration of 0.001-0.5 mass %, which mixture is fed into each oxidation reactor in an ammonia: ammonium salt mass ratio of 1:100 to 100:1.Type: ApplicationFiled: July 29, 2003Publication date: March 25, 2004Inventors: Arkady Samuilovich Dyckman, John William Fulmer, Viktor Vladimirovich Pinson, Andrey Vladimirovich Zinenkov, Boris Issakovich Gorovits
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Patent number: 6486360Abstract: The invention relates to a method for oxidizing organic substrate by using 1O2. According to the inventive method, organic substrates that react with 1O2 are mixed with 30-70% H2O2 in water, in an organic solvent or in a mixture thereof in the presence of a lanthanide as the catalyst. H2O2 is catalytically decomposed to water and 1O2 and is then oxidized to the corresponding oxidation products.Type: GrantFiled: September 28, 2001Date of Patent: November 26, 2002Assignee: DSM Fine Chemicals Austria NFG GmbH & CO KGInventors: Jean-Marie Aubry, Veronique Rataj-Nardello, Paul Alsters
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Patent number: 6426057Abstract: A continuous process for oxidation, in which the substance to be oxidized and the oxidizing gas flow countercurrently and the oxidizing gas is mixed with a split stream containing preoxidized substance before it enters the reactor. A Venturi nozzle is particularly suitable as the mixing organ in the reactor.Type: GrantFiled: November 15, 2001Date of Patent: July 30, 2002Assignee: Degussa AGInventor: Bernhard Maurer
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Patent number: 6150562Abstract: A process for selective thermal oxidation of hydrocarbons adsorbed onto zeolite matrices. A highly selective thermal oxidation of unsubstituted or alkyl substituted alkanes, alkenes, aromatics and cycloalkyls is carried out in solvent free zeolites under dark thermal conditions. The process oxidizes hydrocarbons almost completely selectively without substantial production of byproducts.Type: GrantFiled: June 17, 1999Date of Patent: November 21, 2000Assignee: The Regents of the University of CaliforniaInventors: Heinz Frei, Fritz Blatter, Hai Sun
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Patent number: 5914013Abstract: A process for selective thermal oxidation or photooxidation of hydrocarbons adsorbed onto zeolite matrices. A highly selective thermal oxidation and photooxidation of unsubstituted or alkyl substituted alkanes, alkenes, aromatics and cycloalkyls in solvent free zeolites under dark thermal conditions or under irradiation with visible light. The process oxidizes hydrocarbons almost completely selectively without substantial production of byproducts.Type: GrantFiled: June 13, 1997Date of Patent: June 22, 1999Assignee: The Regents of the University of CaliforniaInventors: Heinz Frei, Fritz Blatter, Hai Sun
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Patent number: 5552131Abstract: A process and apparatus for the molecular oxygen oxidation of a secondary alcohol such as isopropanol to hydrogen peroxide is provided.Type: GrantFiled: June 30, 1994Date of Patent: September 3, 1996Assignee: ARCO Chemical Technology, L.P.Inventor: John C. Jubin, Jr.
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Patent number: 5453548Abstract: A process for the separation of ditertiary butyl peroxide form tertiary butanol is provided which includes the step of dehydrating the tertiary butanol to isobutylene and water.Type: GrantFiled: October 25, 1994Date of Patent: September 26, 1995Assignee: ARCO Chemical Technology, L.P.Inventors: Robert Nedwick, Jeffrey M. McFarland, Leonard A. Fabiano
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Patent number: 5243083Abstract: A method and apparatus for continuously conducting an exothermic chemical reaction between a reactant feedstock such as isobutane and a chemical reactant such as oxygen wherein a circulating stream of the reaction mixture continuously flows up an upstanding draft tube coaxially mounted in a closed upstanding cylindrical reactor and then down the annulus between the cylindrical reactor and the draft tube to establish circulatory motion, and wherein the circulatory motion is thermosyphonically maintained by charging oxygen adjacent the bottom of the draft tube for exothermal reaction with isobutane in the draft tube to thereby heat the upflowing circulating stream, wherein a stream of cold isobutane is continuously introduced adjacent the top of the annulus to cool the circulating stream by direct heat exchange contact, wherein indirect heat exchange cooling coils are provided in the annulus adjacent the top thereof for further cooling the downflowing circulating stream and wherein a discharge line is providedType: GrantFiled: July 24, 1902Date of Patent: September 7, 1993Assignee: Texaco Chemical CompanyInventors: Roderick S. Cowley, Darrell D. Kinzler
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Patent number: 5229425Abstract: A process for producing a stable, bactericidal and fungicidal composition which consists essentially of bubbling air or oxygen into limonene, to produce an oxidized limonene having a rapid bactericidal activity as evidenced by the capability of killing substantially all of the bacteria in a suitable culture medium inoculated with 10.sup.6 colony forming units of Staphylococcus aureus ATCC 25923 per ml. of said broth, containing not more than 0.06 ml of said oxidized limonene per ml. of said broth and incubated at 37.degree. C. in air for 60 minutes.Type: GrantFiled: May 29, 1992Date of Patent: July 20, 1993Assignee: Doyle E. ChastainInventors: Doyle E. Chastain, W. E. Sanders, Jr., Christine C. Sanders
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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: 5183945Abstract: This invention relates to a process for preparing organic hydroperoxides by selectively oxidizing aryl alkyl hydrocarbons to their corresponding organic hydroperoxides using a catalyst certain tetranuclear manganese complexes. The process is carried out without appreciable decomposition by the catalyst of the resulting organic hydroperoxides, and without oxidation by the catalyst of other hydrocarbons present in the starting mixture.The process of the present invention is useful for producing organic hydroperoxides, which themselves are useful as starting materials for a number of commercial reactions, for example, phenol and acetone production.Type: GrantFiled: November 18, 1991Date of Patent: February 2, 1993Assignee: Exxon Research and Engineering CompanyInventors: Robert T. Stibrany, Sergiu M. Gorun
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Patent number: 5175316Abstract: The preparation of cyclohexene oxide, cyclohexanol and cyclohexanone involvesa) oxidizing cyclohexane using a gas containing molecular oxygen to form cyclohexyl hydroperoxide, cyclohexanol and cyclohexanone,b) jointly separating the mixture from a) and c) by distillation, andc) reaction of the cyclohexyl hydroperoxide fraction from b) with cyclohexene in the presence of a transition-metal compound from group 4 to 6, forming cyclohexene oxide, and separating the product mixture in b).Type: GrantFiled: February 10, 1992Date of Patent: December 29, 1992Assignee: BASF AktiengesellschaftInventors: David Agar, Paul-Michael Bever, Hans H. Schuster, Gerald Neubauer
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Patent number: 5153229Abstract: A process for producing a stable, bactericidal and fungicidal composition which consists essentially of bubbling air or oxygen into limonene, to produce an oxidized limonene having a rapid bactericidal activity as evidenced by the capability of killing at least 99.99% of the bacteria in a suitable culture medium inoculated with 10.sup.6 colony forming units of Staphylococcus aureus ATCC 25923 per ml.Type: GrantFiled: June 1, 1990Date of Patent: October 6, 1992Assignee: Doyle E. ChastainInventors: Doyle E. Chastain, W. Eugene Sanders, Jr., Christine C. Sanders
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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: 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: 4900850Abstract: It has been discovered in accordance with the present invention that a tertiary butyl alcohol/ditertiary butyl peroxide azeotrope may be recovered from a product containing tertiary butyl alcohol and ditertiary butyl perioxide by distilling the tertiary butyl alcohol product to obtain an overhead fraction containing substantially all of the ditertiary butyl peroxide as a ditertiary butyl peroxide/tertiary butyl alcohol azeotrope and other contaminants.It has been further discovered in accordance with the present invention that the ditertiary butyl peroxide can be recovered from the distillate fraction by extraction with water (e.g., in a countercurrent water extraction tower) to provide a ditertiary butyl peroxide product of any desired degree of purity.Type: GrantFiled: December 23, 1986Date of Patent: February 13, 1990Assignee: Texaco Inc.Inventors: John R. Sanderson, Robert A. Meyer
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Patent number: 4350829Abstract: There is disclosed a process for the production of isobutyric acid by liquid-phase oxidation of isobutyraldehyde in the presence of an alkali metal-containing compound, the oxidation being effected while maintaining the molar ratio of oxygen to isobutyraldehyde to be fed at 0.5 or above.Type: GrantFiled: June 27, 1979Date of Patent: September 21, 1982Assignee: Mitsubishi Chemical Industries, LimitedInventors: Tatsuo Masuko, Shigeo Fukaya, Nobuyuki Murai, Jun Noma
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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: 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: 4271321Abstract: Process for the preparation of araliphatic dihydroperoxides which comprises oxidizing a hydrocarbon of the formula: ##STR1## with oxygen or an oxygen-containing gas, (2) extracting the resulting dihydroperoxide with an alkali metal hydroxide solution of a concentration of 1-12% thereby producing an aqueous extract and an organic raffinate, (3) neutralizing any alkali metal hydroxide remaining in the organic raffinate with carbon dioxide, thereby producing alkali metal carbonate or bicarbonate in the raffinate, (4) washing the alkali metal carbonate or bicarbonate remaining in the raffinate with wash-water, (5) extracting from the wash-water used in step (4) any dissolved hydroperoxides remaining therein with a hydrocarbon solvent, and (6) optionally recycling the hydroperoxide-containing hydrocarbon solvent into the process. The resulting wash-water effluent is free of polluting and contaminating materials.Type: GrantFiled: October 9, 1979Date of Patent: June 2, 1981Assignee: Chemische Werke Huls AktiengesellschaftInventor: Heinz W. Voges
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Patent number: 4263448Abstract: An oxidizable hydrocarbon is oxidized in a reaction zone at elevated temperature in the presence of a liquid reaction medium by introducing the hydrocarbon and a feed stream containing molecular oxygen to the reaction zone under conditions sufficient to oxidize at least a portion of the hydrocarbon; withdrawing at least a portion of the liquid reaction medium from the reaction zone; passing at least a portion of the withdrawn liquid reaction medium to an oxygen injection zone located external to the reaction zone; contacting the liquid in said oxygen-injection zone with a gas stream containing molecular oxygen under conditions sufficient to form a two-phase gas/liquid mixture; and passing said two-phase gas/liquid mixture to the reaction zone as the feed of molecular oxygen thereto.Type: GrantFiled: March 30, 1979Date of Patent: April 21, 1981Assignee: Halcon Research and Development Corp.Inventor: James Leacock
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Patent number: 4245123Abstract: A method of manufacturing an oxidizing agent comprises the step of oxidizing polyoxyalkylene having an average molecular weight of 1,000 to 30,000 and being represented by the following general formula:--R-O ].sub.nwhere R stands for alkylene group represented by (CH.sub.2)m where m=2 or 3. A solution such as an aqueous solution containing polyoxyalkylene of more than 1% by weight, or a melted polyoxyalkylene is treated by supplying an oxidizing gas thereinto to oxidize and decompose the polyoxyalkylene into the oxidizing agent. A method of oxidation by the use of the oxidizing agent manufactured by the above-described method is applied to, for example, a surface treatment of semiconductor or metal.Type: GrantFiled: October 31, 1978Date of Patent: January 13, 1981Assignee: Sony CorporationInventor: Makoto Inoue