Preparing By Oxidation Patents (Class 568/910)
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Patent number: 6555715Abstract: A process has been developed for oxygenating linear C2 to C6 alkanes to ketones or aldehydes. The process involves reacting the alkanes with oxygen in the presence of a catalyst comprising an imide promoter and a metal co-catalyst. An example of the imide is N-hydroxyphthalimide and an example of the co-catalyst is Co (acetylacetonate). The process is preferably carried out using an inert solvent, an example of which is acetic acid. Optionally, the oxygenated product can be hydrogenated to give the corresponding alcohol which can optionally in turn be dehydrated to provide the corresponding olefin.Type: GrantFiled: October 11, 2001Date of Patent: April 29, 2003Assignee: UOP LLCInventors: Joseph A. Kocal, Robert R. Frame, Jeffery C. Bricker
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Patent number: 6548718Abstract: A process for hydroxylating aliphatic compounds under catalytic distillation conditions to provide alcohols is provided. The aliphatic compound is contacted, in a distillation column reactor, with an oxidation catalyst and an oxidant under conditions effective to hydroxylate the aliphatic compound while maintaining at least a portion of the aliphatic compound in a liquid phase and separating the hydroxylated product from the un-reacted aliphatic compound in the distillation column reactor.Type: GrantFiled: April 24, 2001Date of Patent: April 15, 2003Assignee: Shell Oil CompanyInventors: Brendan Dermot Murray, David Morris Hamilton, Jr.
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Publication number: 20030069452Abstract: A reactant selected from the group consisting of alkanes, alkenes, and aromatics is reacted with a metal halide to form the halide of the reactant and reduced metal. The reduced metal is oxidized to form metal oxide. The metal oxide is reacted with the halide of the reactant to produce the alcohol and/or the ether corresponding to the reactant and the original metal halide which is recycled.Type: ApplicationFiled: November 19, 2002Publication date: April 10, 2003Inventors: Jeffrey H. Sherman, Eric McFarland
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Publication number: 20030065042Abstract: A process for the production of methanol comprises feeding an amount of a hydrocarbon feedstock and an amount of an oxygen feedstock and an optional carbon dioxide feedstock to a partial oxidation reactor and an optional reformer to produce a partial oxidation reactor effluent comprising hydrogen, carbon monoxide and carbon dioxide; electrolyzing water to produce hydrogen and oxygen and recovering at least a portion of the hydrogen to produce a hydrogen stream; adding an amount of a hydrogen feedstock, at least a portion of which is obtained from the hydrogen stream, to the partial oxidation reactor effluent to produce a synthesis gas stream having a predetermined ratio of hydrogen to carbon monoxide and optionally to carbon dioxide; subjecting the synthesis gas to methanol synthesis to produce a methanol product stream and a tail gas stream; separating the tail gas stream into at least two streams comprising a purge stream and a recycle stream, the recycle stream comprising a substantial portion of the tailType: ApplicationFiled: November 2, 2001Publication date: April 3, 2003Inventor: John M. Shaw
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Publication number: 20030055298Abstract: Disclosed is a novel class of modified ruthenium catalysts useful in the one step synthesis of 1,3-PDO comprising (a) a cobalt component comprising one or more non-ligated cobalt compounds; and (b) a ruthenium component comprising in major part a ruthenium carbonyl compound ligated with a phospholanoalkane ligand, solubilized in an ether solvent, that provides potential improvements in cost and performance in one step hydroformylation/hydrogenation. For example, cobalt-ruthenium-bidentate, bis(phospholano)alkane catalyst precursors in ether solvents provide good yields of 1,3-PDO in a one step synthesis.Type: ApplicationFiled: May 30, 2002Publication date: March 20, 2003Inventors: John Frederick Knifton, Talmadge Gail James, Kevin Dale Allen, Paul Richard Weider, Joseph Broun Powell, Lynn Henry Slaugh
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Patent number: 6525230Abstract: In a method of converting alkanes to their corresponding alcohols and ethers a vessel comprises a hollow, unsegregated interior defined first, second, and third zones. In a first embodiment of the invention oxygen reacts with metal bromide in the first zone to provide bromine; bromine reacts with the alkane in the second zone to form alkyl bromide; and the alkyl bromide reacts with metal oxide in the third zone to form the corresponding alcohol and/or ether. Metal bromide from the third zone is transported through the vessel to the first zone and metal oxide from the first zone is recycled to the third zone. A second embodiment of the invention differs from the first embodiment in that metal oxide is transported through the vessel from the first zone to the third zone and metal bromide is recycled from the third zone to the first zone.Type: GrantFiled: April 2, 2002Date of Patent: February 25, 2003Assignee: GRT, Inc.Inventor: Philip Grosso
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Patent number: 6512144Abstract: Processes for oxidizing hydrocarbons using a new family of crystalline manganese phosphate compositions have been developed. These compositions have an extended network which network can be a one-, two-, or three-dimensional network. The composition has an empirical formula of: (Aa+)v(Mnb+)(Mc+)xPyOz where A is a structure directing agent such as an alkali metal, M is a metal such as Al, Fe3+ and “b” is the average manganese oxidation state and varies from greater than 2.0 to a maximum of 3.0. Specific oxidation processes are oxidative dehydrodimerization and oxidative dehydrogenation.Type: GrantFiled: December 1, 2000Date of Patent: January 28, 2003Assignee: UOP LLCInventors: Gregory J. Lewis, Paula L. Bogdan, Feng Xu, Joseph A. Kocal
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Publication number: 20030004379Abstract: Hydrothermally synthesized catalysts comprising a mixed metal oxide are utilized to produce unsaturated carboxylic acids by the vapor phase oxidation of an alkane, or a mixture of an alkane and an alkene, in the presence thereof, or to produce unsaturated nitrites by the vapor phase oxidation of an alkane, or a mixture of an alkane and an alkene, and ammonia in the presence thereof.Type: ApplicationFiled: June 10, 2002Publication date: January 2, 2003Inventors: Anne Mae Gaffney, Ruozhi Song
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Publication number: 20020198416Abstract: Alcohols, ethers, and olefins are manufactured from alkanes by mixing an alkane and bromine in a reactor to form alkyl bromide and hydrogen bromide. The alkyl bromide only or the alkyl bromide and the hydrogen bromide are directed into contact with metal oxide to form an alcohol and/or an ether, or an olefin and metal bromide. The metal bromide is oxidized to form original metal oxide and bromine, both of which are recycled.Type: ApplicationFiled: January 24, 2002Publication date: December 26, 2002Inventors: Xiao Ping Zhou, Ivan Marc Lorkovic, Jeffrey H. Sherman
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Patent number: 6486368Abstract: Alcohols, ethers, and olefins are manufactured from alkanes by mixing an alkane and bromine in a reactor to form alkyl bromide and hydrogen bromide. The alkyl bromide only or the alkyl bromide and the hydrogen bromide are directed into contact with metal oxide to form an alcohol and/or an ether, or an olefin and metal bromide. The metal bromide is oxidized to form original metal oxide and bromine, both of which are recycled.Type: GrantFiled: January 24, 2002Date of Patent: November 26, 2002Assignees: GRT, Inc., The Regents of the University of CaliforniaInventors: Xiao Ping Zhou, Ivan Marc Lorkovic, Jeffrey H. Sherman
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Patent number: 6482989Abstract: A method for oxidizing an alkane, comprising the step of oxidizing said alkane with oxygen in the presence of an aldehyde, a copper-based catalyst and a nitrogen-containing compound. This method may be used to convert alkanes to corresponding alcohols and ketone having pharmaceutical activities, etc.Type: GrantFiled: July 18, 2001Date of Patent: November 19, 2002Assignee: Osaka UniversityInventors: Shun-ichi Murahashi, Naruyoshi Komiya, Yukiko Hayashi
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Patent number: 6479707Abstract: The present invention provides a process for producing 2-butanone and 2-butanol under comparatively mild conditions with a decreased number of steps by direct oxidization of a hydrocarbon, which is cheaper than butenes, as a raw material using molecular oxygen such as air. The process for producing 2-butanone and 2-butanol comprises directly oxidizing n-butane using molecular oxygen in the presence of aluminum phosphate containing transition metal atoms and a selectivity-improving agent, as required.Type: GrantFiled: December 12, 2001Date of Patent: November 12, 2002Assignee: Maruzen Petrochemical Co., Ltd.Inventors: Hideki Omori, Kazuhiko Haba
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Patent number: 6472572Abstract: Methanol and/or dimethyl ether are manufactured from methane by mixing methane and bromine in a reactor to form methyl bromide and hydrogen bromide. The methyl bromide only or the methyl bromide and the hydrogen bromide are directed into contact with metal oxide to form methanol and/or dimethyl ether and a metal bromide. The metal bromide is oxidized to form original metal oxide catalyst and bromine, both of which are recycled.Type: GrantFiled: June 20, 2001Date of Patent: October 29, 2002Assignees: GRT, Inc., The Regents of the University of CaliforniaInventors: Xiao Ping Zhou, Ivan Marc Lorkovic, Galen D. Stucky, Peter C. Ford, Jeffrey H. Sherman, Philip Grosso
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Patent number: 6465696Abstract: Alcohols, ethers, and olefins are manufactured from alkanes by mixing an alkane and bromine in a reactor to form alkyl bromide and hydrogen bromide. The alkyl bromide only or the alkyl bromide and the hydrogen bromide are directed into contact with metal oxide to form an alcohol and/or an ether, or an olefin and metal bromide. The metal bromide is oxidized to form original metal oxide and bromine, both of which are recycled.Type: GrantFiled: September 11, 2001Date of Patent: October 15, 2002Assignees: GRT, Inc., The Regents of the University of CaliforniaInventors: Xiao Ping Zhou, Galen D. Stucky, Jeffrey H. Sherman
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Patent number: 6465699Abstract: Alcohols, ethers, and olefins are manufactured from alkanes by mixing an alkane and bromine in a reactor to form alkyl bromide and hydrogen bromide. The alkyl bromide is directed into contact with metal oxide to form an alcohol and/or an ether, or an olefin and metal bromide. The metal bromide from the alkyl bromide metal oxide reaction is oxidized to form original metal oxide and bromine, both of which are recycled. The hydrogen bromide is separately directed into contact with metal oxide to form water and metal bromide. The metal bromide from the hydrogen bromide metal oxide is oxidized to form the original metal oxide which is recycled.Type: GrantFiled: March 11, 2002Date of Patent: October 15, 2002Assignees: GRI, Inc., The Regents of the University of CaliforniaInventor: Phil Grosso
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Patent number: 6462243Abstract: Alcohols and/or ethers are synthesized from alkanes by mixing an alkane and bromine in a reactor to form alkyl bromide and hydrogen bromide. The alkyl bromide is directed into contact with metal oxide to form alcohol and/or ether and a metal bromide. The metal bromide is oxidized to metal oxide and bromine, both of which are recycled.Type: GrantFiled: September 11, 2001Date of Patent: October 8, 2002Assignees: GRT, Inc., The Regents of the University of CaliforniaInventors: Xiao Ping Zhou, Ivan Marc Lorkovic, Galen D. Stucky, Peter C. Ford, Jeffrey H. Sherman, Philip Grosso
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Publication number: 20020123654Abstract: The present invention provides a process for producing 2-butanone and 2-butanol under comparatively mild conditions with a decreased number of steps by direct oxidization of a hydrocarbon, which is cheaper than butenes, as a raw material using molecular oxygen such as air. The process for producing 2-butanone and 2-butanol comprises directly oxidizing n-butane using molecular oxygen in the presence of aluminum phosphate containing transition metal atoms and a selectivity-improving agent, as required.Type: ApplicationFiled: December 12, 2001Publication date: September 5, 2002Applicant: MARUZEN PETROCHEMICAL CO., LTD.Inventors: Hideki Omori, Kazuhiko Haba
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Patent number: 6380444Abstract: A process for producing an alcohol from a gaseous hydrocarbon, e.g. a lower alkane such as methane, via oxidative reaction of the hydrocarbon in a concentrated sulfuric acid medium in the presence of a catalyst employs an added catalyst comprising a substance selected from iodine, iodine compounds, titanium, titanium compounds, chromiun and chromium compounds.Type: GrantFiled: June 8, 2000Date of Patent: April 30, 2002Assignees: Statoil Research CentreInventors: Niels J. Bjerrum, Gang Xiao, Hans Aage Hjuler
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Publication number: 20020045778Abstract: A method for oxidizing an alkane, comprising the step of oxidizing said alkane with oxygen in the presence of an aldehyde, a copper-based catalyst and a nitrogen-containing compound. This method may be used to convert alkanes to corresponding alcohols and ketone having pharmaceutical activities, etc.Type: ApplicationFiled: July 18, 2001Publication date: April 18, 2002Inventors: Shun-Ichi Murahashi, Naruyoshi Komiya, Yukiko Hayashi
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Publication number: 20020007097Abstract: Catalysts for heterogeneously catalyzed reactions which comprise active components and a catalyst support comprising amounts of &dgr;-Al2O3 which can be detected by X-ray diffractometry, in particular for the oxychlorination of ethylene to 1,2-dichloroethane.Type: ApplicationFiled: May 3, 2001Publication date: January 17, 2002Inventors: Christian Walsdorff, Ruprecht MeiBner, Klaus Harth
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Patent number: 6306364Abstract: A new family of stannosilicate molecular sieves which have the zeolite beta structure are disclosed. These molecular sieves have a three dimensional framework structure composed of SnO2 and SiO2 tetrahedral oxide units and at least one of TiO2 or GeO2 tetrahedral oxide units and have an empirical formula of: (SnxTiySi1-x-y-zGez)2 where “x”, “y” and “z” are the mole fractions of tin, titanium and germanium respectively (“y” and “z” are not simultaneously zero). Processes for the selective oxidation of organic compounds with peroxides using the molecular sieves as catalysts is also presented.Type: GrantFiled: September 28, 1999Date of Patent: October 23, 2001Assignee: UOP LLCInventors: Susana Valencia Valencia, Avelino Corma Canós
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Publication number: 20010006615Abstract: A process for the production of synthesis gas for obtaining compounds such as ammonia or methanol, in which hydrocarbons and steam are reacted first in a primary reforming section (11) and then—together with oxygen—in a secondary reforming section (12), thus obtaining CO, CO2, H2 and possibly N2 which are then fed to a carbon monoxide conversion section (13, 14), is distinguished by the fact of reacting hydrocarbons, steam and oxygen in an autothermal reforming section (20) provided in parallel with respect to other reforming sections (11, 12), and feeding the so produced CO, CO2, H2 and possibly N2 to the carbon monoxide conversion section (13, 14).Type: ApplicationFiled: February 20, 2001Publication date: July 5, 2001Inventor: Marco Badano
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Patent number: 6156931Abstract: A new family of crystalline manganese phosphate compositions has been prepared. These compositions have an extended network which network can be a one-, two-, or three-dimensional network. The composition has an empirical formula of:(A.sup.3+).sub.v (Mn.sup.b+)(M.sup.c+).sub.x P.sub.y O.sub.zwhere A is a structure directing agent such as an alkali metal, M is a metal such as Al, Fe.sup.3+ and "b" is the average manganese oxidation state and varies from greater than 2.0 to a maximum of 3.0. These compositions can be used as adsorbents and as catalysts in the oxidation of hydrocarbons.Type: GrantFiled: March 24, 1999Date of Patent: December 5, 2000Assignee: UOP LLCInventor: Gregory J. Lewis
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Patent number: 6150145Abstract: Fatty acid degradation products are over-produced by oxidative biochemical degradation of a plant biomass containing unsaturated fatty acids and enzymes for the degradation in the presence of additional unsaturated fatty acids. These degradation products are natural flavour and fragrance ingredients.Type: GrantFiled: October 23, 1998Date of Patent: November 21, 2000Assignee: Givaudan Roure (International) SAInventors: Alex Hausler, Charles Ehret, Eva Binggeli
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Patent number: 6100392Abstract: Electron-deficient porphyrins are provided, as well as processes and intermediates for their preparation. In preferred embodiments, the electron-deficient porphyrins are prepared by condensing pyrrole derivatives and removing water thus formed from the resulting reaction mixture.Type: GrantFiled: August 5, 1998Date of Patent: August 8, 2000Assignee: The Trustees of the University of PennsylavaniaInventors: Michael J. Therien, Stephen DiMagno
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Patent number: 6037507Abstract: A non-cyclic branched aliphatic hydrocarbon (e.g., isobutane) is oxidized with oxygen in the presence of an oxidation catalyst comprising an imide compound of the following formula (1) (e.g., N-hydroxyphthalimide) or an oxidation catalyst comprising the imide compound and a co-catalyst (e.g., a transition metal compound of selected from Group 3A, 4A, 5A, 6A, 7A, 8 and 1B elements of the Periodic Table of elements), for the formation of an oxide (e.g., t-butanol, acetone): ##STR1## wherein R.sup.1 and R.sup.2 represent a substituent such as a hydrogen atom or a halogen atom, or R.sup.1 and R.sup.2 may together form a double bond or an aromatic or non-aromatic 5- to 12-membered ring, X is O or OH, and n is 1 to 3.Type: GrantFiled: March 10, 1998Date of Patent: March 14, 2000Assignees: Daicel Chemical Industries, Ltd., Yasutaka IshiiInventors: Tatsuya Nakano, Yasutaka Ishii
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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: 5990363Abstract: The invention comprises a method for the oxidation of alkanes to alcohols and for decomposition of hydroperoxides to alcohols utilizing new compositions of matter, which are metal complexes of porphyrins. Preferred complexes have hydrogen, haloalkyl or haloaryl groups in meso positions, two of the opposed meso atoms or groups being hydrogen or haloaryl, and two of the opposed meso atoms or groups being hydrogen or haloalkyl, but not all four of the meso atoms or groups being hydrogen. Other preferred complexes are ones in which all four of the meso positions are substituted with haloalkyl groups and the beta positions are substituted with halogen atoms. A new method of synthesizing porphyrinogens is also disclosed.Type: GrantFiled: December 29, 1993Date of Patent: November 23, 1999Assignee: Sun Company, Inc.Inventors: Tilak Wijesekera, James E. Lyons, Paul E. Ellis, Jr.
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Patent number: 5955603Abstract: Strapped porphyrins and electron-deficient porphyrins are provided, as well as processes and intermediates for their preparation. In certain embodiments, such compounds are prepared by nucleophilic displacement of leaving groups from methylpyrroles. In other embodiments, such compounds are prepared by condensing pyrrole derivatives and removing water thus formed from the resulting reaction mixture.Type: GrantFiled: October 6, 1998Date of Patent: September 21, 1999Assignees: Trustees of the University of Pennsylvania, Board of Regents of University of NebraskaInventors: Michael J. Therien, Stephen DiMagno
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Patent number: 5945572Abstract: A method for producing aryl alkyl hydroperoxides which comprises selectively oxidizing an aryl alkyl hydrocarbon having the formula: ##STR1## wherein P and Q are hydrogen or an alkyl and may be the same or different from each other; x is an integer of 1-3; and Ar is an aromatic hydrocarbon group having a valence of x, with an oxygen-containing gas in the presence of a transition metal complex which contains, as a ligand, a cyclic polyfunctional amine compound having at least three nitrogen atoms in the ring forming molecular chain or an open chain polyfunctional amine compound having at least three nitrogen atoms in the main chain of the molecule.Type: GrantFiled: October 15, 1998Date of Patent: August 31, 1999Assignee: Mitsui Chemicals, Inc.Inventors: Terunori Fujita, Shigekazu Matsui, Toshihiro Takai, Hideto Matsuoka, Akifumi Kagayama, Hiroshi Kuroda, Masayasu Ishibashi, Hiroshi Iwasaki, Nobuya Hirokane
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Patent number: 5847227Abstract: A method for producing aryl alkyl hydroperoxides which comprises selectively oxidizing an aryl alkyl hydrocarbon having the formula: ##STR1## wherein P and Q are hydrogen or an alkyl and may be the same or different from each other; x is an integer of 1-3; and Ar is an aromatic hydrocarbon group having a valence of x, with an oxygen-containing gas in the presence of a transition metal complex which contains, as a ligand, a cyclic polyfunctional amine compound having at least three nitrogen atoms in the ring forming molecular chain or an open chain polyfunctional amine compound having at least three nitrogen atoms in the main chain of the molecule.Type: GrantFiled: February 27, 1996Date of Patent: December 8, 1998Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Terunori Fujita, Shigekazu Matsui, Toshihiro Takai, Hideto Matsuoka, Akifumi Kagayama, Hiroshi Kuroda, Masayasu Ishibashi, Hiroshi Iwasaki, Nobuya Hirokane
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Patent number: 5817881Abstract: Alkanes are catalytically oxidized in air or oxygen using iron-substituted polyoxoanions (POAs) of the formula:H.sub.e-z ?(n-C.sub.4 H.sub.9).sub.4 N!.sub.z (XM.sub.11 M'O.sub.39).sup.-eThe M' (e.g., iron(III)/iron(II)) reduction potential of the POAs is affected by selection of the central atom X and the framework metal M, and by the number of tetrabutyl-ammonium groups. Decreased Fe(III)/Fe(II) reduction potential has been found to correlate to increased oxidation activity.Type: GrantFiled: July 30, 1997Date of Patent: October 6, 1998Assignee: Sun Company, Inc. (R&M)Inventors: Paul E. Ellis, James E. Lyons, Harry K. Myers, Jr., Shahid N. Shaikh
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Patent number: 5792890Abstract: A tertiary butyl alcohol charge stock contaminated with from about 0.5 to about 2 wt. % of corrosive oxygen-containing impurities, including peroxides and formates, is passed through an oxygenates decomposition reactor containing a bed of a basic zeolite catalyst to decompose the peroxides and oxygen-containing impurities, including peroxides and formates, and to dehydrate a portion of the tertiary butyl alcohol to form isobutylene and water to form a substantially less-corrosive tertiary butyl alcohol feedstock that is substantially free from oxygen-containing impurities, including formates that is suitable for reaction with methanol in a methyl tertiary butyl ether etherification reactor to form a methyl tertiary butyl ether etherification reaction product from which methyl tertiary butyl ether can be recovered.Type: GrantFiled: February 3, 1997Date of Patent: August 11, 1998Assignee: Huntsman Specialty Chemicals Corp.Inventors: Pei-Shing Eugene Dai, Laurence Darrel Neff, Kyle Lee Preston, Rei-Yu Judy Hwan, John Frederick Knifton
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Patent number: 5789627Abstract: Methyl tertiary butyl ether is prepared from contaminated tertiary butyl alcohol and methanol by decomposing peroxides in a peroxides decomposition reactor, by dehydrating the tertiary butyl alcohol to form isobutylene and also decomposing acidic contaminants in a tertiary butyl alcohol dehydration reactor to form a feedstock that is distilled to provide a first lower boiling fraction comprising isobutylene and water; from which isobutylene is recovered for reaction with methanol in an etherification reactor containing a bed of an etherification catalyst to form methyl tertiary butyl ether.Type: GrantFiled: February 20, 1997Date of Patent: August 4, 1998Assignee: Huntsman Specialty Chemicals Corp.Inventors: Rei-Yu Judy Hwan, Kyle Lee Preston
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Patent number: 5786505Abstract: A method of selectively oxidizing an organic compound in a single vessel comprises: a) combining an organic compound, an acid solution in which the organic compound is soluble, a compound containing two oxygen atoms bonded to one another, and a metal ion reducing agent capable of reducing one of such oxygen atoms, and thereby forming a mixture; b) reducing the compound containing the two oxygen atoms by reducing one of such oxygen atoms with the metal ion reducing agent to, 1) oxidize the metal ion reducing agent to a higher valence state, and 2) produce an oxygen containing intermediate capable of oxidizing the organic compound; c) reacting the oxygen containing intermediate with the organic compound to oxidize the organic compound into an oxidized organic intermediate, the oxidized organic intermediate having an oxidized carbon atom; d) reacting the oxidized organic intermediate with the acid counter ion and higher valence state metal ion to bond the acid counter ion to the oxidized carbon atom and therebyType: GrantFiled: July 3, 1996Date of Patent: July 28, 1998Assignee: Battelle Memorial InstituteInventors: Donald M. Camaioni, Michael A. Lilga
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Patent number: 5773634Abstract: The liquid and gaseous products formed by reacting oxygen with isobutane in an oxidation reactor are separately processed; the liquid reaction product being charged to a distillation zone and separated into a lower boiling isobutane fraction and a higher boiling fraction comprising tertiary butyl alcohol and tertiary butyl hydroperoxide; the gaseous reaction product comprising inert gases and vaporized and/or entrained isobutane being cooled by an amount sufficient to condense isobutane contained therein for recycle to the oxidation reactor; the remaining gases, including isobutane being charged to a tertiary butyl alcohol absorber to obtain a solution of isobutane in tertiary butyl alcohol that is recycled to the distillation zone.Type: GrantFiled: November 14, 1996Date of Patent: June 30, 1998Assignee: Huntsman Specialty Chemicals CorporationInventors: David Durham Chess, David George Pottratz, Eileen Tovan Nguyen, William Kemp Culbreth, III
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Patent number: 5723697Abstract: The presence of a base in the reaction mixture in a metal-ligand catalyzed partial oxidation of alkanes results in sustained catalyst activity, and in greater percent conversion as compared with oxidation in the absence of base, while maintaining satisfactory selectivity for the desired oxidation, for example the oxidation of isobutane to isobutanol.Type: GrantFiled: December 29, 1995Date of Patent: March 3, 1998Assignee: Sun Company, Inc. (R&M)Inventors: Manoj V. Bhinde, Thomas W. Bierl
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Patent number: 5723677Abstract: The invention comprises a method for the oxidation of alkanes to alcohols and for decomposition of hydroperoxides to alcohols utilizing new compositions of matter, which are metal complexes of porphyrins. Preferred complexes have hydrogen, haloalkyl or haloaryl groups in meso positions, two of the opposed meso atoms or groups being hydrogen or haloaryl, and two of the opposed meso atoms or groups being hydrogen or haloalkyl, but not all four of the meso atoms or groups being hydrogen. Other preferred complexes are ones in which all four of the meso positions are substituted with haloalkyl groups and the beta positions are substituted with halogen atoms. A new method of synthesizing porphyrinogens is also disclosed.Type: GrantFiled: June 27, 1996Date of Patent: March 3, 1998Assignee: Sun Company, Inc. (R&M)Inventors: Tilak Wijesekera, James E. Lyons, Paul E. Ellis, Jr.
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Patent number: 5710292Abstract: The invention relates to the use of compounds of the formulaRe.sub.a O.sub.b X.sub.c L.sub.d, (I)in whichX=F, Cl, Br, I or OH,L=Lewis base,a=an integer 1, 2 or 3b=zero or an integer from 2 to 9,c=zero or an integer from 1 to 9,d=zero or an integer from 1 to 6,and the sum of a, b and c is such that it is appropriate to the zerovalency or trivalency to heptovalency of the rhenium with the proviso that if b is not equal to zero, b.gtoreq.2.multidot.a, as catalysts for the oxidation of electron-rich aromatic compounds and derivatives thereof and a process for the oxidation of electron-rich aromatic compounds, in which electron-rich C.sub.6 -C.sub.22 aryl compounds and derivatives thereof are oxidized in an organic solvent in the presence of a catalyst of the formula (I) and of a peroxide-containing compound.Type: GrantFiled: June 2, 1995Date of Patent: January 20, 1998Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Anton Herrmann, Joao Domingos Galamba Correia, Richard Walter Fischer
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Patent number: 5663328Abstract: The invention provides novel catalyst compositions, useful in the oxidation of hydrocarbons with air or oxygen to form hydroxy-group containing compounds and in the decomposition of hydroperoxides to form hydroxy-group containing compounds. The catalysts comprise transition metal complexes of a porphyrin ring having 1 to 12 halogen substituents on the porphyrin ring, at least one of said halogens being in a meso position and/or the catalyst containing no aryl group in a meso position. The compositions are prepared by halogenating a transition metal complex of a porphyrin.Type: GrantFiled: June 27, 1996Date of Patent: September 2, 1997Assignee: Sun Company, Inc. (R&M)Inventors: Paul E. Ellis, Jr., James E. Lyons
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Patent number: 5585515Abstract: A method of selectively oxidizing an organic compound in a single vessel comprises: a) combining an organic compound, an acid solution in which the organic compound is soluble, a compound containing two oxygen atoms bonded to one another, and a metal ion reducing agent capable of reducing one of such oxygen atoms, and thereby forming a mixture; b) reducing the compound containing the two oxygen atoms by reducing one of such oxygen atoms with the metal ion reducing agent to, 1) oxidize the metal ion reducing agent to a higher valence state, and 2) produce an oxygen containing intermediate capable of oxidizing the organic compound; c) reacting the oxygen containing intermediate with the organic compound to oxidize the organic compound into an oxidized organic intermediate, the oxidized organic intermediate having an oxidized carbon atom; d) reacting the oxidized organic intermediate with the acid counter ion and higher valence state metal ion to bond the acid counter ion to the oxidized carbon atom and therebyType: GrantFiled: April 30, 1993Date of Patent: December 17, 1996Assignee: Battelle Memorial InstituteInventors: Donald M. Camaioni, Michael A. Lilga
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Patent number: 5574196Abstract: A process for preparing tertiary alkanols which comprises the step of oxidizing with ozone a saturated hydrocarbon having a tertiary carbon center in the presence of a carboxylic acid and for a sufficient period of time and at suitable temperature and pressure to form said alkanols.Type: GrantFiled: February 28, 1995Date of Patent: November 12, 1996Assignee: Hoechst Celanese CorporationInventors: Charles E. Tucker, Diane E. Allen, Charles C. Hobbs
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Patent number: 5563263Abstract: The present invention provides novel D.sub.4 -symmetric chiral porphyrins derived from 1R-(+)-nopinone. The simplicity and flexibility of this synthetic protocol provides an attractive route to this novel class of porphyrins starting from cyclic ketones. For example, the chloromanganese (III) derivatives of the new macrocycles have utility as catalysts for the asymmetric epoxidation of aromatic alkenes.Type: GrantFiled: September 14, 1994Date of Patent: October 8, 1996Assignee: Hoechst Celanese CorporationInventors: Thomas J. Kodadek, John F. Barry
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Patent number: 5491265Abstract: A process for preparing 6-chloro-2-hexanone which comprises the steps of (a) oxidizing methylcyclopentane with ozone in the presence of a carboxylic acid and for a sufficient period of time to form 1-methylcyclopentanol; (b) reacting said 1-methylcyclopentanol with a suitable amount of an alkali metal hypochlorite in the presence of a carboxylic acid to form 1-methylcyclopentyl hypochlorite; and (c) heating said 1-methylcyclopentyl hypochlorite for a sufficient period of time to form 6-chloro-2-hexanone.Type: GrantFiled: February 28, 1995Date of Patent: February 13, 1996Assignee: Hoechst Celanese CorporationInventors: Diane E. Allen, Charles E. Tucker, Charles C. Hobbs, Ramakrishnan Chidambaram
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Patent number: 5489716Abstract: The invention provides novel methods for the oxidation of hydrocarbons with oxygen-containing gas to form hydroxy-group containing compounds and for the decomposition of hydroperoxides to form hydroxygroup containing compounds. The catalysts used in the methods of the invention comprise transition metal complexes of a porphyrin ring having 1 to 12 halogen substituents on the porphyrin ring, at least one of said halogens being in a meso position and/or the catalyst containing no aryl group in a meso position. The catalyst compositions are prepared by halogenating a transition metal complex of a porphyrin.Type: GrantFiled: September 7, 1994Date of Patent: February 6, 1996Assignee: Sun Company, Inc. (R&M)Inventors: Paul E. Ellis, Jr., James E. Lyons
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Patent number: 5480986Abstract: Transition metal complexes of Gable porphyrins having two porphyrin rings connected through a linking group, and having on the porphyrin rings electron-withdrawing groups, such as halogen, nitro or cyano. These complexes are useful as catalysts for the oxidation of organic compounds, e.g. alkanes.Type: GrantFiled: July 30, 1993Date of Patent: January 2, 1996Assignee: Sun Company, Inc. (R&M)Inventors: James E. Lyons, Paul E. Ellis, Jr., Richard W. Wagner
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Patent number: 5478962Abstract: Process for the preparation of dimethylcarbonate which consists in feeding oxygen and a mixture of methanol and carbon monoxide to the reactor, with a molar ratio methanol/carbon monoxide of between 1 and 2, this mixture coming directly from the non catalytic direct oxidation of methane with oxygen characterized in that the above molar ratio between methanol and carbon monoxide, with fixed temperature and pressure values, is obtained by maintaining the ratio between methane and oxygen between 1 and 100, by injections of fresh oxygen into a tubular reactor, during the above oxidation reaction.Type: GrantFiled: February 21, 1995Date of Patent: December 26, 1995Assignee: Enichem S.p.A.Inventors: Laura De Nardo, Maurizio Ghirardini, Gianni Donati
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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: 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: 5436376Abstract: A plural stage process for the production of tertiary butyl alcohol from isobutane wherein isobutane is reacted with oxygen in a first reactor to prepare a primary liquid reaction mixture comprising unreacted isobutane, tertiary butyl alcohol, tertiary butyl hydroperoxide and small amounts of oxygen-containing by-products, distilling the primary reaction product to provide a first lighter isobutane recycle distillation fraction and a first heavier liquid distillation fraction comprising the debutanized mixture of tertiary butyl hydroperoxide with tertiary butyl alcohol, diluting the first heavier liquid distillation fraction with an amount of tertiary butyl alcohol sufficient to provide a feed mixture comprising about 15 to 25 wt. % of tertiary butyl hydroperoxide, about 75 to 85 wt.Type: GrantFiled: August 11, 1994Date of Patent: July 25, 1995Assignee: Texaco Chemical Inc.Inventors: Yu-Hwa E. Sheu, John R. Sanderson, Mark A. Mueller, William A. Smith