Of Hydrocarbon Patents (Class 562/542)
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Publication number: 20040014985Abstract: A method separates a reaction product from an imide compound catalyst represented by Formula (1) or an altered derivative thereof in a reaction mixture obtained as a result of a reaction in the presence of the imide compound catalyst by performing an extraction process using two organic solvents separable from each other to thereby separate the reaction product into one organic solvent layer and the imide compound catalyst or an altered derivative thereof into the other organic solvent layer, respectively: 1Type: ApplicationFiled: May 1, 2003Publication date: January 22, 2004Inventor: Michihiro Sugahara
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Patent number: 6677482Abstract: A method of manufacturing (meth)acrylic acid includes: a reaction step of carrying out a catalytic gas-phase oxidation reaction; an absorbing step of absorbing (meth)acrylic acid from a (meth)acrylic-acid-containing mixed gas prepared in the reaction step; a refinement step of separating, refining, and recovering (meth)acrylic acid from a (meth)acrylic-acid-containing liquid prepared in the absorbing step; and a recirculation step of recirculating (meth)acrylic acid contained in a vent gas produced in the refinement step to the absorbing step and/or the refinement step.Type: GrantFiled: December 20, 2002Date of Patent: January 13, 2004Assignee: Nippon Shokubai Co, Ltd.Inventors: Takeshi Nishimura, Yukihiro Matsumoto
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Publication number: 20030236432Abstract: This invention concerns catalysts comprising a molybdenum compound of formula I, II, III, IV or VType: ApplicationFiled: December 3, 2002Publication date: December 25, 2003Inventors: Kostantinos Kourtakis, John Donal Sullivan
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Patent number: 6664416Abstract: The present invention produces (meth)acrylic acid in a high yield in a process for producing (meth)acrylic acid by subjecting at least one member selected from the group consisting of (meth)acrolein, propane, and isobutane to catalytic gas phase oxidation with molecular oxygen or a molecular-oxygen-containing gas. In addition, the present invention makes it possible to produce (meth)acrylic acid in a high yield and stably for a long time. The present invention provides a process for producing (meth)acrylic acid by catalytic gas phase oxidation reaction, which is characterized by allowing a reaction gas to contain a reducible compound.Type: GrantFiled: April 6, 2002Date of Patent: December 16, 2003Assignee: Nippon Shokubai Co., Ltd.Inventors: Michio Tanimoto, Hiroto Kasuga
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Patent number: 6613940Abstract: In the reaction of catalytic gas phase oxidation by means of a shell-and-tube type reactor adapted to circulate a heating medium to the shell of the reactor through the medium of a circulation device connecting an annular conduit connected thereto, a method for the catalytic gas phase oxidation characterized by subjecting a part of the heating medium extracted from the shell of the reactor to heat exchange, introducing the heating medium resulting from the heat exchange into the proximity of a heating medium circulation inlet on the inlet side of the circulation device or the annular conduit on the outlet side of the reactor. The flow rate of the heating medium after the heat exchange is preferred to be in the range of 2-40 vol. % based on the flow rate of the heating medium within the shell of the reactor and the temperature difference of the heating medium at the inlet and the outlet to be in the range of 15-150° C.Type: GrantFiled: August 25, 2000Date of Patent: September 2, 2003Assignee: Nippon Shokubai Co., Ltd.Inventors: Takeshi Nishimura, Masakatsu Mori, Masatsugu Kitaura, Osamu Dodo, Daisuke Nakamura
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Publication number: 20030109746Abstract: A process for reacting in a fluid bed reactor at least one oxidisable reactant with molecular oxygen in the presence of a catalytically active fluidised bed of solid particles. In the process a molecular oxygen-containing gas having an oxygen concentration greater than that of air is introduced into the fluidised bed whilst the fluidised bed is maintained in a turbulent regime. The process is suitable for oxidation, ammoxidation and carboxylation processes, including the production of maleic anhydride, acrylonitrile, ethylene, acetic acid and vinyl acetate.Type: ApplicationFiled: November 26, 2002Publication date: June 12, 2003Applicant: BP Chemicals LimitedInventors: Michele Fiorentino, David Newton, George Fredrick Salem, Bruce Leo Williams
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Patent number: 6566551Abstract: For use in a process for the production of (meth)acrylic acid comprising at least a step for the reaction of (meth)acrylic acid by catalytic gas phase oxidation and a step for the absorption thereof, a method for preventing an effluent gas pipe from blocking is disclosed, which method is characterized by causing part or the whole of the gas discharged from the step for absorption, while being circulated via the effluent gas pipe to the step for the reaction or being discarded, to be subjected to temperature elevation and application of pressure and/or mist separation. Particularly by setting the temperature of the waste gas from the absorption column at a level in the range of 30-70° C.Type: GrantFiled: November 29, 2000Date of Patent: May 20, 2003Assignee: Nippon Shokubai Co., Ltd.Inventors: Takeshi Nishimura, Yukihiro Matsumoto, Sei Nakahara, Misao Inada, Harunori Hirao, Mamoru Takamura
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Patent number: 6541664Abstract: In a process for heterogeneously catalyzed gas-phase oxidation, a reaction gas starting mixture comprising propane, molecular oxygen and, if desired, inert gas is passed at from 300 to 500° C. over a fixed-bed catalyst.Type: GrantFiled: April 13, 2000Date of Patent: April 1, 2003Assignee: BASF AktiengesellschaftInventors: Harald Jachow, Andreas Tenten, Signe Unverricht, Heiko Arnold
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Patent number: 6528683Abstract: The invention relates to a method for producing shell catalysts for the catalytic vapor-phase oxidation of aromatic carboxylic acids and/or carboxylic acid anhydrides comprised of a supporting core and of catalytically active metal oxides which are deposited in a shell-shaped manner on said supporting core. The inventive catalysts are obtained by spraying an aqueous active mass suspension, said suspension containing the active metal oxides, at higher temperatures onto the hot supporting material which has a temperature ranging from 50 to 450° C. The aqueous active mass suspension contains 1 to 10 wt. %, with regard to the solid content of the active mass suspension, a binding agent comprised of A) a polymerizate obtained by radical polymerization, containing 5 to 100 wt. % of monomers (a) in the form of ethylenically unsaturated acid anhydrides or ethylenically unsaturated dicarboxylic acids whose carboxyl groups can form an anhydride and containing 0 to 95 wt.Type: GrantFiled: November 30, 2000Date of Patent: March 4, 2003Assignee: BASF AktiengesellschaftInventors: Thomas Heidemann, Frank Rosowski, Gerd Linden, Michael Seufert, Gerhard Hefele, Peter Michael Lorz
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Patent number: 6525216Abstract: A method of manufacturing (meth)acrylic acid includes: a reaction step of carrying out a catalytic gas-phase oxidation reaction; an absorbing step of absorbing (meth)acrylic acid from a (meth)acrylic-acid-containing mixed gas prepared in the reaction step; a refinement step of separating, refining, and recovering (meth)acrylic acid from a (meth)acrylic-acid-containing liquid prepared in the absorbing step; and a recirculation step of recirculating (meth)acrylic acid contained in a vent gas produced in the refinement step to the absorbing step and/or the refinement step.Type: GrantFiled: June 7, 2000Date of Patent: February 25, 2003Assignee: Nippon Shokubai Co., Ltd.Inventors: Takeshi Nishimura, Yukihiro Matsumoto
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Patent number: 6521789Abstract: The present invention relates to an improved process for the preparation of adipic acid. More particularly, the present invention relates to an environmental-friendly, clean process for the preparation of adipic acid through oxidation of cyclohexanol, cyclohexanone or a mixture thereof with oxygen or oxygen-containing gas, in the presence of an oxidation initiator, a polar solvent and an organometallic &mgr;3-oxo-bridged Co/Mn cluster complex catalyst.Type: GrantFiled: December 21, 2001Date of Patent: February 18, 2003Assignee: Council of Scientific and Industrial ResearchInventors: Darbha Srinivas, Suhas Arunkumar Chavan, Paul Ratnasamy
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Patent number: 6515172Abstract: Process for the preparation of perfluorocarboxylic acids of the formula RF—COOH, salts thereof and esters thereof from perfluoroalkyl iodides of the formula RF′—I, in which RF and RF′ are cyclic, branched or linear, saturated or unsaturated perfluoroalkyl radicals, by activating the perfluoroalkyl iodides in the presence of oxygen and in organic solvents.Type: GrantFiled: July 10, 2001Date of Patent: February 4, 2003Assignee: Clariant GmbHInventors: Ralf Grottenmüller, Wolfgang Knaup, Anton Probst, Klaus Dullinger
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Publication number: 20020193632Abstract: The present invention produces (meth)acrylic acid in a high yield in a process for producing (meth)acrylic acid by subjecting at least one member selected from the group consisting of (meth)acrolein, propane, and isobutane to catalytic gas phase oxidation with molecular oxygen or a molecular-oxygen-containing gas. In addition, the present invention makes it possible to produce (meth)acrylic acid in a high yield and stably for a long time. The present invention provides a process for producing (meth)acrylic acid by catalytic gas phase oxidation reaction, which is characterized by allowing a reaction gas to contain a reducible compound.Type: ApplicationFiled: April 6, 2002Publication date: December 19, 2002Applicant: Nippon Shakubai Co., Ltd.Inventors: Michio Tanimoto, Hiroto Kasuga
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Publication number: 20020161259Abstract: This invention is directed to a process for dehydrogenating primary alcohols to make salts of carboxylic acids. The process comprises contacting a catalyst, preferably a metal support coated with copper or silver, with an alkaline mixture comprising a primary alcohol. The invention further provides for novel copper-containing and silver-containing catalysts which may be used, for example, in the above process as well as processes for making such catalysts.Type: ApplicationFiled: February 28, 2002Publication date: October 31, 2002Applicant: Monsanto CompanyInventors: David A. Morgenstern, Juan P. Arhancet, Howard C. Berk, William L. Moench, James C. Peterson
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Publication number: 20020143208Abstract: A catalyst comprising a promoted mixed metal oxide is useful for the vapor phase oxidation of an alkane or a mixture of an alkane and an alkene to an unsaturated carboxylic acid and for the vapor phase ammoxidation of an alkane or a mixture of an alkane and an alkene to an unsaturated nitrile.Type: ApplicationFiled: March 12, 2002Publication date: October 3, 2002Inventors: Sanjay Chaturvedi, Anne Mae Gaffney, Scott Han, Michele Doreen Heffner, Ruozhi Song
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Patent number: 6441228Abstract: The present invention provides an apparatus for producing (meth)acrylic acid and a process for producing (meth)acrylic acid with this apparatus wherein the apparatus enables to produce (meth)acrylic acid stably for a long period of time by effectively inhibiting the polymerization of (meth)acrylic acid in its production process (for example, in a reboiler). At least a part of the apparatus is made of a nickel-chromium-iron alloy with a molybdenum content of 3 to 20 mass %, but not including 3 mass %, or with a molybdenum content of 1 to 4 mass % and a copper content of 0.5 to 7 mass %.Type: GrantFiled: December 12, 2000Date of Patent: August 27, 2002Assignee: Nippon Shokubai Co., Ltd.Inventors: Sei Nakahara, Kazuhiko Sakamoto, Yukihiro Matsumoto, Kenji Sanada, Masatoshi Ueoka
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Patent number: 6437180Abstract: A process for preparing aliphatic C4-18 &agr;,&ohgr;-dicarboxylic acids by oxidation of C6-20 &agr;,&ohgr;-dienes with hydrogen peroxide or compounds which release hydrogen peroxide under the reaction conditions as is characterized in that the reaction is carried out in the presence of a transition metal catalyst of group VI and of a mixture containing at least one organic acid and one aprotic organic solvent. A specific temperature profile is maintained at different phases of the reaction, which increases yield and selectivity.Type: GrantFiled: May 11, 2000Date of Patent: August 20, 2002Assignee: Bayer AktiengesellschaftInventors: Michael Schelhaas, Helmut Greiving, Manfred Jautelat
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Publication number: 20020082445Abstract: A process for the oxidation of a C2 to C4 alkane to produce the corresponding alkene and carboxylic acid which process comprises contacting in an oxidation reaction zone, said alkane, molecular oxygen-containing gas, and the corresponding alkene and optionally, water, in the presence of at least one catalyst active for the oxidation of the alkane to the corresponding alkene and carboxylic acid, to produce a product stream comprising alkene, carboxylic acid and water, wherein in said process the molar ratio of alkene to carboxylic acid produced in said oxidation reaction zone is adjusted or maintained at a pre-determined value by controlling the concentrations of the alkene and optional water in said oxidation reaction zone and optionally by also controlling one or more of the pressure, temperature and residence time of the oxidation reaction zone. Such an oxidation process may be used in an integrated process, such as for the manufacture of vinyl acetate or ethyl acetate.Type: ApplicationFiled: September 28, 2001Publication date: June 27, 2002Inventors: Brian Ellis, Andrew Richard Lucy, Mark Stephen Roberts
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Patent number: 6407287Abstract: In a method for producing acrylic acid by the steps of a reaction of catalytic gas phase oxidation, absorbing the acrylic acid with an absorbent, and dehydrating the acrylic acid-containing aqueous solution, the method is characterized that the step of dehydration comprises adding and an azeotropic solvent, distilling the resultant mixture, and adjusting the acrylic acid concentration at the top of the column in the range of 0.06-0.80 wt. %, thereby preventing the bottoms of the azeotropic dehydration column from substantially containing the azeotropic solvent and water. As results, the acrylic acid is kept from forming a polymer in any of the distillation columns involved in the production, and effective utilization of acrylic acid.Type: GrantFiled: March 7, 2001Date of Patent: June 18, 2002Assignee: Nippon Shokubai Co., Ltd.Inventors: Yukihiro Matsumoto, Takeshi Nishimura, Kazuhiko Sakamoto, Hidefumi Haramaki
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Publication number: 20020062038Abstract: A catalyst comprising a promoted mixed metal oxide is useful for the vapor phase oxidation of an alkane or a mixture of an alkane and an alkene to an unsaturated carboxylic acid and for the vapor phase ammoxidation of an alkane or a mixture of an alkane and an alkene to an unsaturated nitrile.Type: ApplicationFiled: August 10, 2001Publication date: May 23, 2002Inventors: Sanjay Chaturvedi, Anne Mae Gaffney, Scott Han, Michele Doreen Heffner, Ruozhi Song
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Patent number: 6384274Abstract: This invention relates to an improved process for preparing acrylic acid from propylene using a single reactor utilizing an increased amount of propylene reactant thereby providing increased capacity and throughput.Type: GrantFiled: February 4, 1999Date of Patent: May 7, 2002Assignee: Rohm and Haas CompanyInventors: James Edward Elder, Charles Michael Lonzetta, Timothy Allen Hale, John Dempster Sornson, Peter David Klugherz, Thomas Albert Kaminski, Donald Alan Ebert
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Publication number: 20020038052Abstract: A process for preparing a catalyst is disclosed. The catalyst is useful for the gas phase oxidation of alkanes to unsaturated aldehydes or carboxylic acids or for the ammoxidation of alkanes to unsaturated nitrites.Type: ApplicationFiled: September 11, 2001Publication date: March 28, 2002Inventors: Leonard Edward Bogan,, Michele Doreen Heffner, Bradley Anson Jacobs, Richard David Link, III, Elsie Mae Vickery
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Patent number: 6359173Abstract: Methods and devices for controlling the reaction of a hydrocarbon to an acid by making phase-related adjustments are disclosed. In order to improve reaction rate and reactivity of the oxidation, a single phase at the operating temperature is attained and maintained by adjusting one or more of gaseous oxidant flow rate, pressure in the reaction zone, temperature in the reaction zone, feed rate of hydrocarbon, feed rate of solvent, feed rate of water if water is being fed, feed rate of the catalyst and other parameters. Methods and devices are also disclosed, wherein a hydrocarbon is reacted at a steady state with a gaseous oxidant to form an acid in a liquid mixture. The amount of water is maintained between a maximum level of water, over which maximum level the substantially single liquid phase is transformed to two liquid phases, and a minimum level under which catalyst precipitates.Type: GrantFiled: December 12, 1997Date of Patent: March 19, 2002Assignee: RPC Inc.Inventors: Sharon M. Aldrich, David C. DeCoster, Eustathios Vassiliou, Mark W. Dassel, Ader M. Rostami
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Publication number: 20020010364Abstract: This invention relates to a process for producing one or more organic acids in high purity which process comprises (i) oxidizing in a liquid oxidation reactor one or more organic liquids with essentially pure oxygen or oxygen-enriched air containing at least about 50% oxygen, at a temperature sufficiently stable to prevent cycling of reaction rate, to produce a crude reaction product fluid, and (ii) refining said crude reaction product fluid to give said one or more organic acids in high purity. The oxidation temperature is preferably controlled to within about ±3° C. of a target temperature. The organic acids described herein is useful in a variety of applications, such as intermediates in the manufacture of chemical compounds, pharmaceutical manufacture and the like.Type: ApplicationFiled: April 21, 1998Publication date: January 24, 2002Inventors: JOHN BRAITHWAITE, DAVID ROBERT BRYANT, DAVID JAMES MILLER, JOHN EARL LOGSDON
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Publication number: 20010053864Abstract: Methods and devices for controlling the reaction rate and/or reactivity of a hydrocarbon to an intermediate oxidation product, such as an acid, within predetermined limits, are disclosed. Control of the reaction rate and/or reactivity within predetermined limits is achieved by monitoring and controlling the oxidant consumption rate. According to the present invention, examples of ways to determine the oxidant consumption rate include, but are not limited to, monitoring the flow rates of incoming and outgoing oxidant, monitoring pressure differentials after temporarily ceasing entry and exit of gases, and monitoring the flow rates of incoming and outgoing gases, and monitoring the rates of incoming and outgoing hydrocarbon.Type: ApplicationFiled: April 30, 2001Publication date: December 20, 2001Inventors: David C. DeCoster, Eustathios Vassiliou, Mark W. Dassel, Sharon M. Aldrich, Ader M. Rostami
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Patent number: 6288273Abstract: The invention relates to a method for producing gas-phase catalysts gas-phase oxidation of aromatic hydrocarbons into carboxylic acids and/or carboxylic acid anhydrides upon whose carrier material a coating containing catalytically active metal oxide is applied in the form of a shell, wherein a powder is initially produced from a solution and/or suspension of catalytically active metal oxides and the precursor compounds thereof or simply the precursor compounds in the presence or absence of auxiliary agents in order to produce the catalyst. Said powder is then applied, in the form of a shell, to the carrier in the presence or absence of auxiliary agents after or without previous conditioning and without previous thermal treatment to produce the catalyst. The carrier which is thus coated undergoes thermal treatment in order to produce catalytically active metal oxides.Type: GrantFiled: August 26, 1999Date of Patent: September 11, 2001Assignee: BASF AktiengesellschaftInventors: Thomas Heidemann, Thomas Cimniak, Bernhard Ulrich
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Patent number: 6288274Abstract: Methods and devices for controlling the reaction rate and/or reactivity of a hydrocarbon to an intermediate oxidation product, such as an acid, within predetermined limits, are disclosed. Control of the reaction rate and/or reactivity within predetermined limits is achieved by monitoring and controlling the oxidant consumption rate. According to the present invention, examples of ways to determine the oxidant consumption rate include, but are not limited to, monitoring the flow rates of incoming and outgoing oxidant, monitoring pressure differentials after temporarily ceasing entry and exit of gases, and monitoring the flow rates of incoming and outgoing gases, and monitoring the rates of incoming and outgoing hydrocarbon.Type: GrantFiled: February 19, 1999Date of Patent: September 11, 2001Assignee: RPC Inc.Inventors: David C. DeCoster, Eustathios Vassiliou, Mark W. Dassel, Sharon M. Aldrich, Ader M. Rostami
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Publication number: 20010005763Abstract: The present invention provides an apparatus for producing (meth)acrylic acid and a process for producing (meth)acrylic acid with this apparatus wherein the apparatus enables to produce (meth)acrylic acid stably for a long period of time by effectively inhibiting the polymerization of (meth)acrylic acid in its production process (for example, in a reboiler). At least a part of the apparatus is made of a nickel-chromium-iron alloy with a molybdenum content of 3 to 20 mass %, but not including 3 mass %, or with a molybdenum content of 1 to 4 mass % and a copper content of 0.5 to 7 mass %.Type: ApplicationFiled: December 12, 2000Publication date: June 28, 2001Applicant: Nippon Shokubai Co., Ltd.Inventors: Sei Nakahara, Kazuhiko Sakamoto, Yukihiro Matsumoto, Kenji Sanada, Masatoshi Ueoka
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Patent number: 6147256Abstract: Carboxylic acids, e.g., adipic acid, are more selectively prepared by oxidizing cyclohexane with oxygen or an oxygen-containing gas, in liquid phase, in a solvent reaction medium which comprises a polar protic or aprotic solvent, and also in the presence of a catalytically effective amount of catalyst values dissolved in said solvent reaction medium, the catalyst values comprising at least one solvent-soluble cobalt compound and at least one solvent-soluble chromium compound.Type: GrantFiled: April 10, 1998Date of Patent: November 14, 2000Assignee: Rhodia Fiber and Resin IntermediatesInventors: Michel Costantini, Eric Fache
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Patent number: 6090977Abstract: In a process for the continuous heterogeneously catalyzed gas-phase partial oxidation of an organic compound in an oxidation reactor, whose feed gas mixture comprises, apart from the organic compound to be partially oxidized and molecular oxygen as oxidant, at least one diluent gas which is essentially inert under the conditions of the heterogeneously catalyzed gas-phase partial oxidation, where the essentially inert diluent gas consists partly of combustible gases, after passage through the oxidation reactor, the combustible constituents of the inert diluent gas present in the product gas stream leaving the oxidation reactor are not recirculated to the heterogeneously catalyzed gas-phase partial oxidation, but are put to further use for the purposes of another chemical reaction.Type: GrantFiled: March 5, 1996Date of Patent: July 18, 2000Assignee: BASF AktiengesellschaftInventors: Werner Hefner, Otto Machhammer, Hans-Peter Neumann, Andreas Tenten, Wilhelm Ruppel, Herbert Vogel
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Patent number: 5998572Abstract: Methods and devices for controlling the oxidation of a hydrocarbon to an acid by regulating the temperature hold-up time, and conversion in consecutive reaction zones. The temperature in the consecutive reaction zones progressively decreases, while the hold-up time increases. Preferably, the conversion also increases. One of the major advantages of the methods and devices of the present invention is that an outstanding balance between productivity and selectivity/yield of the desired acid may be achieved. In this respect high yields and selectivities may be obtained without sacrificing productivity.Type: GrantFiled: May 12, 1998Date of Patent: December 7, 1999Assignee: RPC Inc.Inventors: Ader M. Rostami, Mark W. Dassel, Eustathios Vassiliou, David C. DeCoster
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Patent number: 5939582Abstract: Methods and apparatuses for controlling exothermic reactions involving a first reactant contained in a liquid and a second reactant in a gas to form a reaction product by atomizing the liquid in an environment of a gas and removing heat of reaction by condensing vapors of the liquid in a reaction chamber. Preferably, the condensation takes place on a simultaneously atomized second liquid of lower temperature than the atomized liquid containing the first reactant. The compositions of the two liquids are preferably similar. This invention provides waste minimization and considerable environmental improvement.Type: GrantFiled: July 17, 1998Date of Patent: August 17, 1999Assignee: Twenty-First Century Research CorporationInventors: Mark William Dassel, Eustathios Vassiliou
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Patent number: 5922908Abstract: This invention relates to methods of preparing dibasic acids, such as adipic acid for example, by oxidizing a hydrocarbon with a gas containing an oxidant, preferably oxygen. A respective hydrocarbon is reacted with a gaseous oxidant to form dibasic acid in a mixture which preferably contains a solvent, a catalyst, and an initiator. The temperature of the mixture is then lowered to a point at which solid dibasic acid is precipitated, while maintaining a single liquid phase. At least part of the formed acid is then removed.Type: GrantFiled: March 27, 1997Date of Patent: July 13, 1999Assignee: Twenty-First Century Research CorporationInventors: Mark William Dassel, David Cole DeCoster, Ader Meherban Rostami, Sharon Marie Aldrich, Eustathios Vassiliou
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Patent number: 5883292Abstract: Methods and apparatuses for controlling exothermic reactions involving a first reactant contained in a liquid and a second reactant in a gas to form a reaction product by atomizing the liquid in an environment of a gas and removing heat of reaction by condensing vapors of the liquid in a reaction chamber. Preferably, the condensation takes place on a simultaneously atomized second liquid of lower temperature than the atomized liquid containing the first reactant. The compositions of the two liquids are preferably similar. This invention provides waste minimization and considerable environmental improvement.Type: GrantFiled: January 17, 1996Date of Patent: March 16, 1999Assignee: Twenty-First Century Research CorporationInventors: Mark William Dassel, Eustathios Vassiliou
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Patent number: 5736012Abstract: A process for the preparation of a fluorinated acid such as trifluoroacetic acid, including admixing an hydrofluorocarbon, such as 1,1,1-trifluoroethane, with chlorine, an oxidizing agent and an additive to prevent or minimize decomposition; and irradiating the reaction mixture with a light source having a wavelength ranging from 2000 .ANG. to 14000 .ANG..Type: GrantFiled: September 10, 1996Date of Patent: April 7, 1998Assignee: AlliedSignal Inc.Inventors: Alagappan Thenappan, Michael Van Der Puy
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Patent number: 5541037Abstract: The invention provides an anti-reflective material comprising a salt of a carboxyl-terminated fluorinated alkyl polyether compound with a water-soluble amino compound. A resist pattern is defined by forming anti-reflective layer of the anti-reflective material on a photoresist layer, exposing the photoresist layer to a desired pattern of light, removing the anti-reflective layer, and developing the photoresist layer. A fine resist pattern having improved dimensional and alignment accuracies can be defined in a simple, efficient, reproducible manner without substantial environmental pollution. The invention is advantageously utilized in photo-lithography using photoresists.Type: GrantFiled: December 20, 1994Date of Patent: July 30, 1996Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Mitsuo Umemura, Hirohumi Kishita
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Patent number: 5510525Abstract: A process for direct oxidative carbonylation of lower alkanes to acids having one greater carbon atom. The process uses a metal salt catalyst promoted by halide ions and/or a metal with oxygen as the oxidant in an aqueous medium. The process is especially effective for conversion of methane to acetic acid.Type: GrantFiled: December 16, 1994Date of Patent: April 23, 1996Assignee: Gas Research InstituteInventors: Ayusman Sen, Minren Lin
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Patent number: 5393922Abstract: A process for catalytic direct oxidation of hydrocarbons, particularly lower alkanes and single ring aromatics, to acids by dioxygen under mild temperature conditions using specified metal or metal salt catalysts. Turnovers in excess of 1000 for acetic acid formation from ethane and in excess of 100 for formic acid formation from methane have been obtained at reaction temperatures below about 100.degree. C. using palladium catalyst. A coreductant of carbon monoxide in an aqueous system is preferred.Type: GrantFiled: July 22, 1993Date of Patent: February 28, 1995Assignee: Gas Research InstituteInventors: Ayusman Sen, Minren Lin
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Patent number: 5386055Abstract: A process for depolymerizing polymers by selective, partial oxidation at supercritical or near supercritical conditions for water and wherein supercritical water or water near supercritical conditions is used as a solvent and reforming agent, is used to produce relatively high yields of the monomers originally used to produce the polymers. The invention provides an environmentally friendly process for recycling polymeric waste materials to generate valuable polymer feedstock in a closed oxidation process which is free of hazardous stack emissions. The polymers which can be recycled in accordance with the process can include typical amounts of conventional additive and other impurities without significantly affecting the overall conversion.Type: GrantFiled: August 11, 1993Date of Patent: January 31, 1995Assignee: The University of AkronInventors: Sunggyu Lee, Mehmet A. Gencer, Kathy L. Fullerton, Fouad O. Azzam
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Patent number: 5380931Abstract: A method of oxidatively cleaving polyethylenically unsaturated compound having a pair of carbon atoms ethylenically bonded to other carbon atoms but singly bonded to each other or a pair of carbon atoms ethylenically bonded to other carbon atoms but separated from each other by a saturated carbon atom to produce a carboxylic acid is disclosed. A hydroperoxide such as hydrogen peroxide is used as the oxidant and a salt of vanadic acid such as sodium metavanadate is used as a catalyst to oxidatively cleave such an unsaturated compound in a polar organic solvent. Ethylenically unsaturated compounds that do not contain carbon-carbon double bonds separated by one or two carbon-carbon single bonds, such as a monoethylenically unsaturated carboxylic acid present in a mixture with the polyethylenically unsaturated compound, are not oxidized or only minimally oxidized.Type: GrantFiled: October 27, 1993Date of Patent: January 10, 1995Assignee: NDSU Research FoundationInventors: Devendra K. Srivastava, Mashupye M. Kgaphola
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Patent number: 5198580Abstract: Disclosed is a process for the partial oxidation of propane to yield acrylic acid, propylene, acrolein and acetic acid by contacting propane in admixture with a molecular oxygen-containing gas in a reaction zone with an oxidic solid catalyst that1) contains the components and proportions represented by the empirical formulaBi.sub.b Mo.sub.c V.sub.v A.sub.a D.sub.d E.sub.e O.sub.xwhereinA is one or more of K, Na, Li, Cs and Tl,D is one or more of Fe, Ni, Co, Zn, Ce and La,E is one or more of W, Nb, Sb, Sn, P, Cu, Pb, B, Mg, Ca and Sr,a, d and e are each zero-10b is 0.1-10c is 0.1-20v is 0.1-10c:b is from 2:1 to 30:1v:b is from 1.5:1 to 8:1and2) is made by performing a bismuth molybdate containing composition having at least 0.67 atoms of Mo per atom of Bi, before combining with any vanadium compound.Type: GrantFiled: November 18, 1991Date of Patent: March 30, 1993Assignee: The Standard Oil CompanyInventors: Joseph P. Bartek, Ann M. Ebner, James R. Brazdil
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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: 4804779Abstract: The invention provides a two-step process where polychlorinated biphenyls CBs), i.e. biphenyl having 2 to 10 chlorine atoms, are first reduced to unsubstituted biphenyl, then oxidized to a biodegradable dicarboxylic acid having the formula: (CH.sub.2).sub.n (CO.sub.2 H).sub.2, where n=0 to 10 possible --CH.sub.2 --units for application in aqueous systems including water, mud and wet soil.Type: GrantFiled: November 4, 1985Date of Patent: February 14, 1989Assignee: The United States of America as represented by the Secretary of the NavyInventor: Thomas Novinson
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Patent number: 4260808Abstract: Equimolar amounts of phenol and formaldehyde may be prepared from oxygen and toluene. The catalytic oxidation of toluene, when carried out in the presence of acetic anhydride, forms phenyl acetate and methylene diacetate. Pyrolysis of these two intermediates yields phenol and formaldehyde.Significant improvements in this process are achieved when the first stage of the reaction is carried out in the presence of MoO.sub.3.In a further embodiment of this invention it has been found that Group VIII dithiosemibenzil compounds, particularly nickel dithiosemibenzil, serves as a superior promoter for the toluene oxidation reaction.In still a further embodiment of this invention it has been found that persulfate promoters such as potassium persulfate, persulfuric acid, or Caro's dry acid are particularly effective promoters for the toluene oxidation reaction.In a like manner, hydroquinone or resorcinol may be obtained from cresyl acetates.Type: GrantFiled: November 3, 1978Date of Patent: April 7, 1981Assignee: Suntech, Inc.Inventors: James E. Lyons, George Suld, Robert W. Shinn
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Patent number: 4225728Abstract: Equimolar amounts of vinyl acetate and phenol may be prepared by oxidation of ethyl benzene. The catalytic oxidation, of ethyl benzene, when carried out in the presence of acetic anhydride, forms phenyl acetate and ethylidene diacetate. Pyrolysis of these two intermediates yields vinyl acetate and phenol.In a further embodiment of this invention it has been found that persulfate promoters such as potassium persulfate, persulfuric acid, or Caro's dry acid are particularly effective promoters for this oxidation reaction.Type: GrantFiled: November 3, 1978Date of Patent: September 30, 1980Assignee: Suntech, Inc.Inventors: James E. Lyons, George Suld, Robert W. Shinn
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Patent number: 4200764Abstract: The present invention provides an unsupported catalyst with superior crush strength for use in a vapor phase reaction for the high yield conversion of lower aliphatic hydrocarbons such as n-butane to corresponding monocarboxylic acids used as acetic acid. The catalyst is prepared by the reduction of a vanadium oxide containing chromium catalyst.Type: GrantFiled: December 12, 1977Date of Patent: April 29, 1980Assignee: Celanese CorporationInventors: William E. Slinkard, Anthony B. Baylis, Michael P. Hughes
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Patent number: 4195188Abstract: The present invention provides a highly efficient process for use in the high pressure catalytic vapor phase reaction for the high yield conversion of lower aliphatic hydrocarbons such as n-butane to corresponding monocarboxylic acids such as acetic acid. The oxidation reaction takes place under hydrocarbon rich conditions. The increased efficiency in this process is realized by the judicious use of steam and the catalyst systems set forth in the instant invention.Type: GrantFiled: December 12, 1977Date of Patent: March 25, 1980Assignee: Celanese CorporationInventors: William E. Slinkard, Anthony B. Baylis, Peter B. DeGroot, Michael P. Hughes
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Patent number: 4140864Abstract: New substituted acyl derivatives of amino acids which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.Type: GrantFiled: March 24, 1978Date of Patent: February 20, 1979Assignee: E. R. Squibb & Sons, Inc.Inventors: Miguel A. Ondetti, Frank L. Weisenborn
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Patent number: 4111832Abstract: A process for regenerating a deactivated oxidation catalyst, especially one containing vanadium oxide, wherein the deactivated catalyst is treated with an aqueous solution of ammonia and/or an amine at an elevated temperature so as to dissolve at least a portion of the catalyst and the resultant solution or suspension is treated in a known manner to obtain the reactivated catalyst.Type: GrantFiled: November 22, 1976Date of Patent: September 5, 1978Assignee: Bayer AktiengesellschaftInventors: Klaus Rohbock, Rudolf Wiemers, Peter Woditsch, Reinhard Thiel