Acyclic Hydroperoxide Produced Patents (Class 568/571)
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Patent number: 9211483Abstract: Disclosed is a method for the production of 1233xf comprising the continuous low temperature liquid phase reaction of 1,1,1,2,3-pentachloropropane and anhydrous HF, without the use of a catalyst, wherein the reaction takes place in one or more reaction vessels, each one in succession converting a portion of the original reactants fed to the lead reaction vessel and wherein the reactions are run in a continuous fashion.Type: GrantFiled: January 30, 2014Date of Patent: December 15, 2015Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski, Haiyou Wang, Selma Bektesevic
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Patent number: 8975444Abstract: A process for oxidizing cumene to cumene hydroperoxide using an oxygen containing gas, which process composes—conducting a cumene feed and an oxygen containing gas feed to at least the first oxidation reactor in a series of 3-8 reactors, thereby forming an oxidation mixture, and—conducting the oxidation mixture from one oxidation reactor to at least one subsequent reactor, wherein—the reactors are operated with reducing liquid levels; —the oxidation is operated as a dry oxidation, whereby the only gaseous feeds conducted to the oxidation reactors are the cumene feed and the oxygen containing gas feed; —the oxygen containing gas feed is washed with caustic and then with water to remove all acidic or caustic traces before conducting it into an oxidation reactor; —the pressure within each oxidation reactor is in the range of 0-10 barg; —the off-gases from the top section of each oxidation reactor are separated and cooled, whereby a condensate containing unreacted cumene is formed, and—washing the condensate andType: GrantFiled: December 17, 2009Date of Patent: March 10, 2015Assignee: Borealis AGInventors: Veli-Matti Purola, Anja Mannerla
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Patent number: 8952202Abstract: The present invention concerns a process for oxidizing cumene to cumene hydroperoxide using an oxygen containing gas, preferably air, which process comprises —conducting a cumene feed and an oxygen containing gas feed to at least the first oxidation reactor in a series of 3-8 reactors, thereby forming an oxidation mixture, and conducting the formed oxidation mixture from one reactor to the next, preferably after an oxidation reaction has taken place, wherein —the reactors comprise at least one lower pressure oxidizer (1) as the first reactor in the series and at least one higher pressure oxidizer (2) as the last reactor in the series; —any lower pressure oxidizer is operated at a pressure of at least atmospheric pressure and any higher pressure oxidizer is operated at a pressure of at least 0.5 bar higher than said at least one lower pressure oxidizer.Type: GrantFiled: December 17, 2009Date of Patent: February 10, 2015Assignee: Borealis AGInventor: Veli-Matti Purola
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Publication number: 20140303400Abstract: A process for the complete or partial oxygenation of hydrocarbons comprises contacting a C1-C8 hydrocarbon, molecular oxygen, and hydrogen peroxide, in the presence of water and a heterogeneous catalyst, under conditions suitable to convert the C1-C8 hydrocarbon to at least one corresponding C1-C8 oxygenate product, wherein the heterogeneous catalyst provides confinement and contains both Brønsted-Lowry acid centers and Lewis acid centers. The reaction may be carried out at a temperature ranging from 2° C. to 90° C. The use of molecular oxygen increases the economic attractiveness of the process while also improving yield.Type: ApplicationFiled: October 3, 2012Publication date: October 9, 2014Applicant: UNIVERSITY COLLEGE CARDIFF CONSULTANTS LIMITEDInventors: Graham J. Hutchings, Michael M. Forde, Jose A. Lopez - Sanchez, Nikolaos Dimitratos
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Patent number: 8710100Abstract: The present invention relates to compounds comprising the general formula (I), in which R1 and R2, which may be identical or different, are selected from the group comprising —H or a linear or branched alkyl group having from 1 to 6 carbon atoms or together form an aromatic or aliphatic ring with 5 or 6 atoms; Y and Z, which may be identical or different, are selected from the group comprising —H, —OH, —COOH, —OR3, —CH(OR3)COOH, in which R3 is selected from H, phenyl, benzyl, —CF3 or —CF2CF3, vinyl, allyl and a linear or branched alkyl group having from 1 to 6 carbon atoms.Type: GrantFiled: February 29, 2012Date of Patent: April 29, 2014Assignee: Nogra Pharma LimitedInventors: Giancarlo Naccari, Sergio Baroni
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Publication number: 20120157647Abstract: A rubber-modified polymeric composition having predominately core-shell morphology is disclosed. The rubber-modified polymeric composition can be a polystyrene comprising styrene, polybutadiene, and a high-grafting initiator formed by contacting singlet oxygen with an olefin containing an allylic hydrogen or a diene to form a hydroperoxide or peroxide. The singlet oxygen can be formed by contacting ground state oxygen with a photo catalyst, such a photosensitive dye exposed to light.Type: ApplicationFiled: February 15, 2012Publication date: June 21, 2012Applicant: Fina Technology, Inc.Inventor: Olga Khabashesku
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Patent number: 8017812Abstract: The invention relates to a process for the liquid phase oxidation of ethylbenzene into ethylbenzene hydroperoxide, wherein the ethylbenzene hydroperoxide concentration is kept below 20 wt. % on the basis of the total weight of the reaction mixture, and wherein styrene and/or a styrene derivative is fed to the ethylbenzene. The concentration of said styrene and/or a styrene derivative may be from 0.01 to 5.0 wt. %.Type: GrantFiled: November 12, 2007Date of Patent: September 13, 2011Assignee: Shell Oil CompanyInventors: Anthonius Johannes Maria Breed, Andrew David Horton, Peter Anton August Klusener
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Patent number: 7763755Abstract: To provide a method for producing dialkylhydroperoxybenzene by liquid-phase oxidation of dialkylbenzene, wherein the method comprises the following steps, Oxidation step: a step of obtaining a oxidation reaction liquid having pH of 9 to 12, which contains dialkylhydroperoxybenzene, unreacted dialkylbenzene, and by-produced hydroperoxybenzenes by subjecting an oxidation raw material solution containing dialkylbenzene to oxidation reaction, Aqueous solution extracting step: a step of extracting the oxidation reaction liquid with an alkaline aqueous solution to obtain a water layer mainly containing dialkylhydroperoxybenzene and by-produced hydroperoxybenzenes, and an oil layer mainly containing dialkylbenzene, and Recycle step: a step of recycling and feeding at least a part of the oil layer obtained in the aqueous solution extracting step to the oxidation step, wherein the oxidation step comprises two or more reaction sections of a first section and subsequent sections arranged in series, and the temperatureType: GrantFiled: February 14, 2007Date of Patent: July 27, 2010Assignee: Sumitomo Chemical Company, LimitedInventor: Mitsuru Onuma
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Publication number: 20080221367Abstract: Horizontal reactor vessel (1) having a lower part (3) and two opposite ends (9, 10), which reactor vessel comprises a liquid inlet (13) at one end (9), a fluid outlet (14) at the opposite end (10) and a gas inlet device (17) arranged in the lower part (3), which reactor vessel contains at least one substantially vertical baffle-plate (23) arranged in the direction of liquid flow through the reactor vessel (1) during normal operation.Type: ApplicationFiled: September 1, 2005Publication date: September 11, 2008Inventors: Elco Dick Hollander, Peter Anton August Klusener, Ingmar Hubertus Josephina Ploemen, Cornelius Johannes Schellekens
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Patent number: 7053161Abstract: A process for producing organic peroxide initiators useful in the polymerization of ethylenically unsaturated monomers. The process for making the organic peroxides includes forming an aqueous emulsion of the organic peroxide. The organic peroxide is dispersed as small droplets of from 1 to 10 microns in size in the aqueous emulsion. The organic peroxide may be added to a polymerization reactor containing an ethylenically unsaturated monomer. The organic peroxide functions as a free radical initiator to polymerize the monomer. The organic peroxide may be substantially free of organic solvents and plasticizers. The resulting polymers are of high quality.Type: GrantFiled: January 12, 2005Date of Patent: May 30, 2006Assignee: Oxy Vinyls, L.P.Inventors: Ross J. Cozens, Qi Wang, M. Fredrick V. Glock, Jr., Daniel A. Zust
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Patent number: 7038090Abstract: A process and catalyst for preparing organic hydroperoxides by oxidizing hydrocarbon compounds in the presence of an oxygen-containing gas and a catalyst containing a transition metal on a solid support.Type: GrantFiled: April 1, 2004Date of Patent: May 2, 2006Assignee: UOP LLCInventors: Timothy A. Brandvold, Gregory J. Lewis, Lisa M. King, Lawrence E. Brewer
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Patent number: 6774249Abstract: Improved polymer-immobilized photosensitizer are disclosed as well as methods of preparing and using them. The polymer-immobilized photosensitizers comprise a cross-linked polymer backbone, a plurality of cationic ammonium or phosphonium groups covalently bound to the polymer backbone and an immobilized photosensitizer. The average total number of carbon atoms in the ammonium or phosphonium group is at least four and preferably at least 12. The photosensitizer can be either covalently or ionically bound to the polymer. Polymer-supported photosensitizers of the invention are unexpectedly superior in catalyzing the photosensitized oxidation of compounds containing carbon-carbon double bonds.Type: GrantFiled: September 27, 2001Date of Patent: August 10, 2004Assignee: Lumigen, Inc.Inventors: Hashem Akhavan-Tafti, Richard S. Handley, Mark D. Sandison, Randall K. Larkin
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Patent number: 6703528Abstract: There are disclosed are a method for producing at least one compound selected from a carbonyl compound and a hydroxy adduct compound by an oxidative cleavage or addition reaction of an olefinic double bond of an olefin compound, which contains reacting an olefin compound with hydrogen peroxide, utilizing as a catalyst, at least one member selected from (a) tungsten, (b) molybdenum, or (c) a tungsten or molybdenum metal compound containing (ia) tungsten or (ib) molybdenum and (ii) an element of Group IIIb, IVb, Vb or VIb excluding oxygen, and a catalyst composition.Type: GrantFiled: August 10, 2001Date of Patent: March 9, 2004Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Hagiya, Naoyuki Takano, Akio Kurihara
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Patent number: 6700024Abstract: A process for preparing organic hydroperoxides, which process comprises: (a) oxidation of an organic compound to obtain reaction product containing organic hydroperoxide, (b) contacting at least part of the organic hydroperoxide containing reaction product with a basic aqueous solution, (c) separating hydrocarbonaceous phase containing organic hydroperoxide from aqueous phase, (d) contacting at least part of the separated hydrocarbonaceous phase containing organic hydroperoxide with an aqueous solution comprising wastewater, and (e) separating the hydrocarbonaceous phase containing organic hydroperoxide from the aqueous phase. The invention further relates to a process for preparing an oxirane compounds with the help of this process, and a to a process for preparing an alkenyl aryl with the help of this process.Type: GrantFiled: September 19, 2002Date of Patent: March 2, 2004Assignee: Shell Oil CompanyInventors: Gerard Du Cauze de Nazelle, Wan Shi Foong, Tjeerd Willem Garritsen, Raymond Lawrence June, Mohammad Azmi Bin Othman, Eduardus Petrus Simon Schouten
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Patent number: 6620974Abstract: A method for manufacturing cumene hydroperoxide comprises reacting cumene and oxygen in the presence of a water phase comprising aqueous ammonia, and in the absence of an additive comprising an alkali or alkaline earth metal, to form cumene hydroperoxide. A system for producing cumene hydroperoxide comprises a cumene feed in fluid communication with a reactor having a cumene hydroperoxide oxidate outlet; an oxygen feed in fluid communication with the reactor; and an ammonia feed in fluid communication with the cumene feed and/or the reactor, wherein the cumene feed, the oxygen feed, the ammonia feed, and the reactor are free of an additive comprising an alkali or alkaline earth metal.Type: GrantFiled: August 21, 2002Date of Patent: September 16, 2003Assignee: General Electric CompanyInventors: John William Fulmer, Eugene Edward Scott, William Dale Kight
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Patent number: 6476276Abstract: A process for preparing hydroperoxides which comprises oxidizing hydrocarbon by a gas containing oxygen in the presence of a specific compound and converting them selectively to corresponding hydroperoxides. The specific compound is the compound that can capture radicals. The preferable example may be a compound selected from radicals of oxygen, nitrogen, phosphorus, sulfur, carbon or silicon or a compound that forms radicals of these in the reaction system. The present invention can be applied to oxidation of hydrocarbons including arylalkylhydrocarbons such as cumene, m-diisopropylbenzene, p-diisopropylbenzene, 1,3,5-triisopropylbenzene, isopropylnaphthalene, diisopropylnaphthalene, isopropylbiphenyl, diisopropylbiphenyl, etc.Type: GrantFiled: July 19, 2001Date of Patent: November 5, 2002Assignee: Mitsui Chemicals, Inc.Inventors: Shigekazu Matsui, Hiroshi Kuroda, Nobuya Hirokane, Haruyuki Makio, Toshihiro Takai, Koji Kato, Terunori Fujita, Makoto Kamimura
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Patent number: 6465695Abstract: A method for manufacturing cumene hydroperoxide comprises reacting cumene and oxygen in the presence of a water phase comprising aqueous ammonia, and in the absence of an additive comprising an alkali or alkaline earth metal, to form cumene hydroperoxide. A system for producing cumene hydroperoxide comprises a cumene feed in fluid communication with a reactor having a cumene hydroperoxide oxidate outlet; an oxygen feed in fluid communication with the reactor; and an ammonia feed in fluid communication with the cumene feed and/or the reactor, wherein the cumene feed, the oxygen feed, the ammonia feed, and the reactor are free of an additive comprising an alkali or alkaline earth metal.Type: GrantFiled: July 27, 2001Date of Patent: October 15, 2002Assignee: General Electric CompanyInventors: John William Fulmer, Eugene Edward Scott, William Dale Kight
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Patent number: 6372927Abstract: The process for preparing an alkylene oxide adduct, including the steps of feeding an organic compound having active hydrogen and an alkylene oxide to a reaction column packed with a solid catalyst, and carrying out addition reaction of the organic compound having active hydrogen with an alkylene oxide in a gas-liquid fixed bed reaction, wherein the alkylene oxide is in a state of gas and the organic compound having active hydrogen is in a state of liquid.Type: GrantFiled: August 10, 1998Date of Patent: April 16, 2002Assignee: Kao CorporationInventors: Nobuhiro Tatsumi, Yoshikazu Ogura, Takanobu Katayama, Osamu Tabata
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Patent number: 6369278Abstract: There are provided: (I) a process for preparing an extract containing at least one hydroperoxide, which comprises the steps of: (1) oxidizing an aromatic hydrocarbon substituted with an alkyl group to obtain a liquid reaction mixture, and (2) extracting at least one hydroperoxide in the liquid reaction mixture to obtain an extract having a concentration of acetone of not more than 1% by weight: and (II) a process for preparing an extract containing at least one hydroperoxide, which comprises the steps of, (1) oxidizing an aromatic hydrocarbon substituted with an alkyl group to obtain a liquid reaction mixture, and (2) extracting at least one hydroperoxide with an aqueous alkali solution having an A value of not more than 10 to obtain an extract.Type: GrantFiled: December 7, 2000Date of Patent: April 9, 2002Assignee: Sumitomo Chemical Company, LimitedInventors: Tomoyuki Noritake, Shigeru Goto, Kenji Itoh
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Patent number: 6291718Abstract: A process for preparing hydroperoxides which comprises oxidizing hydrocarbon by a gas containing oxygen in the presence of a specific compound and converting them selectively to corresponding hydroperoxides. The specific compound is the compound that can capture radicals. The preferable example may be a compound selected from radicals of oxygen, nitrogen, phosphorus, sulfur, carbon or silicon or a compound that forms radicals of these in the reaction system. The present invention can be applied to oxidation of hydrocarbons including arylalkylhydrocarbons such as cumene, m-diisopropylbenzene, p-diisopropylbenzene, 1,3,5-triisopropylbenzene, isopropylnaphthalene, diisopropylnaphthalene, isopropylbiphenyl, diisopropylbiphenyl, etc.Type: GrantFiled: March 2, 1999Date of Patent: September 18, 2001Assignee: Mitsui Chemicals, Inc.Inventors: Shigekazu Matsui, Hiroshi Kuroda, Nobuya Hirokane, Haruyuki Makio, Toshihiro Takai, Koji Kato, Terunori Fujita, Makoto Kamimura
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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: 6077977Abstract: Aryldialkylmethanes such as cumene are converted to the corresponding hydroperoxides by reaction with oxygen in the presence of a promoter which may be an alkali metal borate such as borax, an alkali metal salt of a polymer such as an acrylic polymer, or an alkaline reagent in combination with a specific proportion of added water or water of hydration, also exemplified by borax. High yields of the hydroperoxide are obtained, particularly when the promoter includes water.Type: GrantFiled: June 1, 1998Date of Patent: June 20, 2000Assignee: General Electric CompanyInventors: Sarada Gopinathan, John William Fulmer, Changaramponnath Gopinathan, John Christopher Schmidhauser
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Patent number: 6023001Abstract: Peroxides are prepared from organic compounds and oxygen in a reaction vessel by introducing organic compound and oxygen to the reaction vessel and by simultaneously withdrawing a first liquid product stream from adjacent the top of the reactor and a second liquid product stream from adjacent the bottom of the reaction vessel. Suitable organic compounds include, but are not limited to, alkanes and all aryl compounds.Type: GrantFiled: March 18, 1998Date of Patent: February 8, 2000Assignee: Huntsman ICI Chemicals LLCInventors: William K. Culbreth, III, Mark E. Taylor, Kyle L. Preston, Mark A. Mueller
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Patent number: 6011183Abstract: The invention relates to a process for preparing organic hydroperoxides by oxidation of a hydrocarbon feed with molecular oxygen at supercritical conditions, which process is carried out in the presence of a separate liquid water phase that is present in an amount of 0.5 to 20% weight on the weight of the feed as a water film on the inner walls of the reactor vessel.Type: GrantFiled: November 13, 1998Date of Patent: January 4, 2000Assignee: Shell Oil CompanyInventors: Stephen William Bourne, Pieter Oldenhove
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Patent number: 5908962Abstract: Greater efficiency in a water-alkaline emulsion cumene oxidation process using a cascade of reactors is obtained by splitting the reactor cascade into 2 stages with the first stage utilizing NH.sub.4 NaCO.sub.3 as the active carbonate in the stage containing less than 18% by weight cumene hydroperoxide and using Na.sub.2 CO.sub.3 as the active carbonate in the stage containing more than 18% by weight cumene hydroperoxide. By directly injecting ammonia into a recycle stream organic acids are efficiently neutralized. A counter current water wash of the second stage also increases process efficiency by scrubbing out unwanted impurities. Control of pH in the process improves efficiency and reduces impurity levels.Type: GrantFiled: February 9, 1998Date of Patent: June 1, 1999Assignee: General Electric Company and Illa InternationalInventors: Vladimir Mikhailovich Zakoshansky, Andrei Konstantinovich Griaznov, Irina I. Vasilieva, John W. Fulmer, William D. Kight
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Patent number: 5856586Abstract: Disclosed is a process for the preparation of 2,5-dimethyl-2,5-dihydroperoxyhexene by reaction of 2,5-dimethyl-1,5-hexadiene with hydrogen peroxide in an acidic medium. According to this process, the 2,5-dimethyl-2,5-dihydroperoxyhexane can be prepared with good yield and in a technically simple way.Type: GrantFiled: January 24, 1997Date of Patent: January 5, 1999Assignee: Peroxid-Chemie GmbHInventors: Eberhard Hagel, Werner Zeiss
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Patent number: 5767322Abstract: Greater efficiency in a water-alkaline emulsion cumene oxidation process using a cascade of reactors is obtained by splitting the reactor cascade into 2 stages with the first stage utilizing NH.sub.4 NaCO.sub.3 as the active carbonate in the stage containing less than 18% by weight cumene hydroperoxide and using Na.sub.2 CO.sub.3 as the active carbonate in the stage containing more than 18% by weight cumene hydroperoxide. By directly injecting ammonia into a recycle stream organic acids are efficiently neutralized. A counter current water wash of the second stage also increases process efficiency by scrubbing out unwanted impurities. Control of pH in the process improves efficiency and reduces impurity levels.Type: GrantFiled: June 27, 1996Date of Patent: June 16, 1998Assignee: General Electric CompanyInventors: Vladimir Mikhailovich Zakoshansky, Andrei Konstantinovich Griaznov, Irina I. Vasilieva, John W. Fulmer, William D. Kight
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Patent number: 5539131Abstract: In the Oxirane process for epoxide production, at least part of the alcohol formed during isobutane or isopentane peroxidation is replaced by an inert solvent such as decane.Type: GrantFiled: July 13, 1995Date of Patent: July 23, 1996Assignee: ARCO Chemical Technology, L.P.Inventor: Shaw-Chan Lin
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Patent number: 5475147Abstract: Isobutane containing a significant amount of isobutylene is treated at conditions effective to oligomerize a predominance of the isobutylene, isobutane substantially free of isobutylene is separated from the oligomer products, and the isobutane substantially free of isobutylene is oxidized to tertiary butyl hydroperoxide.Type: GrantFiled: October 19, 1994Date of Patent: December 12, 1995Assignee: ARCO Chemical Technology, L.P.Inventor: Thomas S. Zak
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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: 5436375Abstract: Tertiary butyl hydroperoxide and tertiary butyl alcohol are prepared from isobutane and oxygen in a vertical reactor by sparging a mixture of isobutane with oxygen to the bottom of the reactor, by charging a reaction mixture recycle stream to the reactor above the sparge point, by centrally charging a downwardly flowing stream of cooled fresh isobutane to the top of the reactor to induce central downflow of the fresh isobutane annular and upflow of the sparged mixture and the recycle stream, by withdrawing a liquid product stream adjacent the top of the reactor, by withdrawing a vapor product stream from the top of the reactor, by condensing entrained liquids in the vapor product, by recycling the condensed liquids and by recovering the liquid product stream.Type: GrantFiled: August 26, 1994Date of Patent: July 25, 1995Assignee: Texaco Chemical Inc.Inventors: Karen A. Thomas, Kyle L. Preston
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Patent number: 5399777Abstract: In the non-catalytic liquid phase oxidation of isobutane, it has been found that the reaction is initiated with 0.05 wt % to 0.08 wt % tertiary butyl hydroperoxide.Type: GrantFiled: March 21, 1994Date of Patent: March 21, 1995Assignee: Texaco Chemical Inc.Inventor: Mark A. Mueller
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Patent number: 5395980Abstract: In the non-catalytic liquid phase oxidation of isobutane, it has been found that the reaction is initiated with 0.05 wt % to 0.08 wt % ditertiary butyl peroxide.Type: GrantFiled: March 21, 1994Date of Patent: March 7, 1995Assignee: Texaco Chemical Inc.Inventors: Mark A. Mueller, John R. Sanderson
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Patent number: 5334771Abstract: A secondary carbon atom in an alkane, including alkyl groups attached to aromatic rings, or cycloalkane is peroxidized by molecular oxygen to the corresponding hydroperoxide in the absence of a catalyst. The peroxidation is carried out in the presence of a tertiary hydroperoxide initiator which provides the free radicals needed to maintain the reaction. The amount of tertiary alcohol in the initiator is limited. The initial product of the peroxidation contains the secondary hydroperoxide as well as unreacted hydrocarbon, unreacted tertiary hydroperoxide and tertiary alcohol. The tertiary alcohol is removed as an azeotrope with part of the unreacted hydrocarbon which may be then separated from the alcohol and recycled. A second azeotropic distillation follows where the unreacted tertiary hydroperoxide is removed as an azeotrope with the rest of the unreacted hydrocarbon. This azeotrope is directly recycled to the peroxidation reaction.Type: GrantFiled: July 14, 1993Date of Patent: August 2, 1994Assignees: ABB Lummus Crest Inc., Nitrocarbono S.A.Inventors: George Ember, Edilberto A. De Castro Netro, Rogerio F. De Lacerda
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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: 5243084Abstract: 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 as distillate from fractional distillation of vapors from the oxidation zone.Type: GrantFiled: December 17, 1992Date of Patent: September 7, 1993Assignee: ARCO Chemical Technology, L.P.Inventors: Robert N. Cochran, Shaw-Chan Lin
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Patent number: 5220075Abstract: A secondary carbon atom in an alkane, including alkyl groups attached to aromatic rings, or cycloalkane is oxidized by molecular oxygen to the corresponding hydroperoxide in the absence of a catalyst. The oxidation is carried out in the presence of a tertiary hydroperoxide initiator which provides the free radicals needed to maintain the reaction. The amount of tertiary alcohol in the initiator is limited.Type: GrantFiled: July 17, 1992Date of Patent: June 15, 1993Assignee: ABB Lummus Crest Inc.Inventor: George Ember
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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: 5154912Abstract: The peroxides which include the O.sup.17 isotope, especially the hydrogen peroxides and peroxides and hydroperoxides prepared therefrom, are well adapted as nonradioactive labeled compounds for use in the medicinal and biological arts.Type: GrantFiled: September 20, 1990Date of Patent: October 13, 1992Assignee: AtochemInventors: Jean-Pierre Schirmann, Jean-Jacques Barieux
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Patent number: 5151530Abstract: The distillation product fraction obtained from an isobutane oxidation reaction product after the removal of unreacted isobutane will contain tertiary butyl hydroperoxide, tertiary butyl alcohol and carboxylic acid contaminants such as formic acid, acetic acid and isobutyric acid. It has been discovered that when the distillation product fraction is treated with about 1/2 to 1 equivalents of calcium oxide and/or calcium hydroxide based on the carboxylic acid content of the distillate product fraction, a portion of the carboxylic acid contaminants will precipitate thus partially purifying the distillation product fraction so that, thereafter, molybdenum precipitation will be substantially inhibited when the thus-treated distillation product fraction is used as a feedstock for an epoxidation reaction wherein tertiary butyl hydroperoxide is reacted with an olefin in the presence of a soluble molybdenum catalyst to provide an olefin epoxide and additional tertiary butyl hydroperoxide.Type: GrantFiled: September 25, 1991Date of Patent: September 29, 1992Assignee: Texaco Chemical CompanyInventors: Edward T. Marquis, John R. Sanderson, Robert A. Meyer
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Patent number: 5149885Abstract: The present invention relates to the oxidation of isobutane to TBHP wherein the oxidation exothermic heat of reaction is removed by circulating a portion of the liquid reaction mixture through an indirect heat exchanger and comprises the further feature that the molecular oxygen necessary for the oxidation is introduced by means of sparging into the cooled, circulating liquid reaction mixture.Type: GrantFiled: February 20, 1992Date of Patent: September 22, 1992Assignee: Arco Chemical Technology, L.P.Inventor: John C. Jubin, Jr.
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Patent number: 5104493Abstract: The invention relates to a process for concentrating TBHP while avoiding flammability and explosion hazards by distilling a mixture of TBHP and TBA under reduced pressure of up to 300 mm Hg and separating a liquid TBHP concentrate containing at least 65 wt. % TBHP.Type: GrantFiled: January 24, 1991Date of Patent: April 14, 1992Assignee: Arco Chemical Technology, L.P.Inventor: Victor M. Chong
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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: 5093506Abstract: The distillation product fraction obtained from an isobutane oxidation reaction product after the removal of unreacted isobutane will contain tertiary butyl hydroperoxide, tertiary butyl alcohol and carboxylic acid contaminants such as formic acid, acetic acid and isobutyric acid. It has been discovered that when the distillation product fraction is treated with about 1/2 to 1 equivalents of calcium oxide and/or calcium hydroxide based on the carboxylic acid content of the distillate product fraction, a portion of the carboxylic acid contaminants will precipitate thus partially purifying the distillation product fraction so that, thereafter, molybdenum precipitation will be substantially inhibited when the thus-treated distillation product fraction is used as a feedstock for an epoxidation reaction wherein tertiary butyl hydroperoxide is reacted with an olefin in the presence of a soluble molybdenum catalyst to provide an olefin epoxide and additional tertiary butyl hydroperoxide.Type: GrantFiled: August 30, 1989Date of Patent: March 3, 1992Assignee: Texaco Chemical CompanyInventors: Edward T. Marquis, John R. Sanderson, Robert A. Meyer
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Patent number: 5030739Abstract: The invention is directed to a process for the catalytic oxidation of an isoprenoid containing at least one allylic hydrogen atom, which process comprises reacting the isoprenoid with oxygen or an oxygen-containing gas in an inert solvent in the presence of a N-hydroxydicarboxylic acid imide of the formula ##STR1## wherein A-B stands for CH.sub.2 -CH.sub.2, CH.dbd.CH, an aromatic hydrocarbon residue or a group derived from one of these groups in which one or more hydrogen atoms is/are replaced by alkyl or halogen,to produce a primary of secondary hydroperoxide.The process of the invention is suitable for the manufacture of steroids, vitamins, odorant substances, carotinoids and the like.Type: GrantFiled: August 31, 1990Date of Patent: July 9, 1991Assignee: Hoffman-La Roche Inc.Inventors: Joseph Foricher, Claude Furbringer, Karlheinz Pfoertner
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Patent number: 4962040Abstract: 2-Hydrazono-4,6-dinitrobenzthiazolones of the formula ##STR1## in which X.sub.1 represents hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -hydroxyalkyl, C.sub.1 -C.sub.4 -sulphoalkyl or C.sub.1 -C.sub.4 -sulphatoalkyl, andX.sub.2 represents hydrogen or --SO.sub.2 X.sub.3, whereX.sub.3 may represent hydrogen, C.sub.1 -C.sub.8 -alkyl or optionally substituted aryl andX.sub.1 also represents a double bond between the cyclic nitrogen atom and the carbon atom 2 according to the formula II below: ##STR2## where X.sub.2 has the meaning specified under the above formula. These hydrazones may be employed in the preparation of azo dyestuffs and as color formers for detecting of biological substances, and in the determination of H.sub.2 O.sub.2.Type: GrantFiled: August 10, 1989Date of Patent: October 9, 1990Assignee: Bayer AktiengesellschaftInventors: Herbert Hugl, Aloysius Engel, Klaus Wehling
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Patent number: 4922035Abstract: Tertiary butyl alcohol is prepared by the catalytic decomposition of tertiary butyl hydroperoxide, preferably in solution in tertiary butyl alcohol, in the presence of a metal phthalocyanine catalyst promoted with a C.sub.1 to C.sub.18 thiol and a free radical inhibitor, such as a phthalocyanine of a metal of Group IB, Group VIIB or Group VIIIB of the Periodic Table (e.g., chloroferric phthalocyanine, dodecane thiol and 2,3-dihydroxynaphthalene).Type: GrantFiled: September 8, 1987Date of Patent: May 1, 1990Assignee: Texaco Inc.Inventors: John R. Sanderson, Edward T. Marquis
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Patent number: 4922034Abstract: Tertiary butyl alcohol is prepared by the catalytic decomposition of tertiary butyl hydroperoxide, preferably in solution in tertiary butyl alcohol, in the presence of a metal porphine catalyst, optionally promoted with a C.sub.1 to C.sub.18 alkyl thiol and an amine, such as an iron (III) or manganese (III) porphine and, optionally, a thiol such as dodecane thiol and an amine, such as a heterocyclic amine (e.g., pyridine, quinoline, isoquinoline, imidazole or a 1-alkyl or 2-alkyl imidazole).Type: GrantFiled: September 8, 1987Date of Patent: May 1, 1990Assignee: Texaco Inc.Inventors: John R. Sanderson, Edward T. Marquis, Mark A. Mueller
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Preparation of tertiary butyl alcohol by the catalytic decomposition of tertiary butyl hydroperoxide
Patent number: 4922033Abstract: A tertiary butyl hydroperoxide feedstock, such as one prepared by the reaction of isobutane with molecular oxygen comprising tertiary butyl hydroperoxide dissolved in tertiary butyl alcohol, is charged to a catalytic decomposition zone where the tertiary butyl hydroperoxide is catalytically decomposed in the presence of a soluble ruthenium catalyst compound promoted with a bidentate ligand to provide a decomposition reaction product characterized by a high conversion rate and a high selectivity of tertiary butyl hydroperoxide to tertiary butyl alcohol.Type: GrantFiled: September 8, 1987Date of Patent: May 1, 1990Assignee: Texaco Inc.Inventors: John R. Sanderson, John F. Knifton, Edward T. Marquis -
Patent number: 4922036Abstract: Tertiary butyl alcohol is prepared by the catalytic decomposition of tertiary butyl hydroperoxide, preferably in solution in tertiary butyl alcohol, in the presence of a borate-promoted metal phthalocyanine catalyst such as a Group IB, VIIB or VIIIB metal phthalocyanine and a Group IA, IIA or IIB metal borate, for example, chloroferric phthalocyanine and lithium borate, barium borate, zinc borate or sodium metaborate.Type: GrantFiled: September 8, 1987Date of Patent: May 1, 1990Assignee: Texaco Inc.Inventors: John R. Sanderson, Edward T. Marquis, John F. Knifton