Preparing By Oxidation Patents (Class 568/910)
  • Patent number: 6555715
    Abstract: 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: Grant
    Filed: October 11, 2001
    Date of Patent: April 29, 2003
    Assignee: UOP LLC
    Inventors: Joseph A. Kocal, Robert R. Frame, Jeffery C. Bricker
  • Patent number: 6548718
    Abstract: 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: Grant
    Filed: April 24, 2001
    Date of Patent: April 15, 2003
    Assignee: Shell Oil Company
    Inventors: Brendan Dermot Murray, David Morris Hamilton, Jr.
  • Publication number: 20030069452
    Abstract: 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: Application
    Filed: November 19, 2002
    Publication date: April 10, 2003
    Inventors: Jeffrey H. Sherman, Eric McFarland
  • Publication number: 20030065042
    Abstract: 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 tail
    Type: Application
    Filed: November 2, 2001
    Publication date: April 3, 2003
    Inventor: John M. Shaw
  • Publication number: 20030055298
    Abstract: 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: Application
    Filed: May 30, 2002
    Publication date: March 20, 2003
    Inventors: John Frederick Knifton, Talmadge Gail James, Kevin Dale Allen, Paul Richard Weider, Joseph Broun Powell, Lynn Henry Slaugh
  • Patent number: 6525230
    Abstract: 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: Grant
    Filed: April 2, 2002
    Date of Patent: February 25, 2003
    Assignee: GRT, Inc.
    Inventor: Philip Grosso
  • Patent number: 6512144
    Abstract: 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: Grant
    Filed: December 1, 2000
    Date of Patent: January 28, 2003
    Assignee: UOP LLC
    Inventors: Gregory J. Lewis, Paula L. Bogdan, Feng Xu, Joseph A. Kocal
  • Publication number: 20030004379
    Abstract: 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: Application
    Filed: June 10, 2002
    Publication date: January 2, 2003
    Inventors: Anne Mae Gaffney, Ruozhi Song
  • Publication number: 20020198416
    Abstract: 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: Application
    Filed: January 24, 2002
    Publication date: December 26, 2002
    Inventors: Xiao Ping Zhou, Ivan Marc Lorkovic, Jeffrey H. Sherman
  • Patent number: 6486368
    Abstract: 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: Grant
    Filed: January 24, 2002
    Date of Patent: November 26, 2002
    Assignees: GRT, Inc., The Regents of the University of California
    Inventors: Xiao Ping Zhou, Ivan Marc Lorkovic, Jeffrey H. Sherman
  • Patent number: 6482989
    Abstract: 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: Grant
    Filed: July 18, 2001
    Date of Patent: November 19, 2002
    Assignee: Osaka University
    Inventors: Shun-ichi Murahashi, Naruyoshi Komiya, Yukiko Hayashi
  • Patent number: 6479707
    Abstract: 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: Grant
    Filed: December 12, 2001
    Date of Patent: November 12, 2002
    Assignee: Maruzen Petrochemical Co., Ltd.
    Inventors: Hideki Omori, Kazuhiko Haba
  • Patent number: 6472572
    Abstract: 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: Grant
    Filed: June 20, 2001
    Date of Patent: October 29, 2002
    Assignees: GRT, Inc., The Regents of the University of California
    Inventors: Xiao Ping Zhou, Ivan Marc Lorkovic, Galen D. Stucky, Peter C. Ford, Jeffrey H. Sherman, Philip Grosso
  • Patent number: 6465696
    Abstract: 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: Grant
    Filed: September 11, 2001
    Date of Patent: October 15, 2002
    Assignees: GRT, Inc., The Regents of the University of California
    Inventors: Xiao Ping Zhou, Galen D. Stucky, Jeffrey H. Sherman
  • Patent number: 6465699
    Abstract: 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: Grant
    Filed: March 11, 2002
    Date of Patent: October 15, 2002
    Assignees: GRI, Inc., The Regents of the University of California
    Inventor: Phil Grosso
  • Patent number: 6462243
    Abstract: 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: Grant
    Filed: September 11, 2001
    Date of Patent: October 8, 2002
    Assignees: GRT, Inc., The Regents of the University of California
    Inventors: Xiao Ping Zhou, Ivan Marc Lorkovic, Galen D. Stucky, Peter C. Ford, Jeffrey H. Sherman, Philip Grosso
  • Publication number: 20020123654
    Abstract: 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: Application
    Filed: December 12, 2001
    Publication date: September 5, 2002
    Applicant: MARUZEN PETROCHEMICAL CO., LTD.
    Inventors: Hideki Omori, Kazuhiko Haba
  • Patent number: 6380444
    Abstract: 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: Grant
    Filed: June 8, 2000
    Date of Patent: April 30, 2002
    Assignees: Statoil Research Centre
    Inventors: Niels J. Bjerrum, Gang Xiao, Hans Aage Hjuler
  • Publication number: 20020045778
    Abstract: 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: Application
    Filed: July 18, 2001
    Publication date: April 18, 2002
    Inventors: Shun-Ichi Murahashi, Naruyoshi Komiya, Yukiko Hayashi
  • Publication number: 20020007097
    Abstract: 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: Application
    Filed: May 3, 2001
    Publication date: January 17, 2002
    Inventors: Christian Walsdorff, Ruprecht MeiBner, Klaus Harth
  • Patent number: 6306364
    Abstract: 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: Grant
    Filed: September 28, 1999
    Date of Patent: October 23, 2001
    Assignee: UOP LLC
    Inventors: Susana Valencia Valencia, Avelino Corma Canós
  • Publication number: 20010006615
    Abstract: 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: Application
    Filed: February 20, 2001
    Publication date: July 5, 2001
    Inventor: Marco Badano
  • Patent number: 6156931
    Abstract: 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: Grant
    Filed: March 24, 1999
    Date of Patent: December 5, 2000
    Assignee: UOP LLC
    Inventor: Gregory J. Lewis
  • Patent number: 6150145
    Abstract: 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: Grant
    Filed: October 23, 1998
    Date of Patent: November 21, 2000
    Assignee: Givaudan Roure (International) SA
    Inventors: Alex Hausler, Charles Ehret, Eva Binggeli
  • Patent number: 6100392
    Abstract: 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: Grant
    Filed: August 5, 1998
    Date of Patent: August 8, 2000
    Assignee: The Trustees of the University of Pennsylavania
    Inventors: Michael J. Therien, Stephen DiMagno
  • Patent number: 6037507
    Abstract: 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: Grant
    Filed: March 10, 1998
    Date of Patent: March 14, 2000
    Assignees: Daicel Chemical Industries, Ltd., Yasutaka Ishii
    Inventors: Tatsuya Nakano, Yasutaka Ishii
  • Patent number: 6023001
    Abstract: 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: Grant
    Filed: March 18, 1998
    Date of Patent: February 8, 2000
    Assignee: Huntsman ICI Chemicals LLC
    Inventors: William K. Culbreth, III, Mark E. Taylor, Kyle L. Preston, Mark A. Mueller
  • Patent number: 5990363
    Abstract: 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: Grant
    Filed: December 29, 1993
    Date of Patent: November 23, 1999
    Assignee: Sun Company, Inc.
    Inventors: Tilak Wijesekera, James E. Lyons, Paul E. Ellis, Jr.
  • Patent number: 5955603
    Abstract: 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: Grant
    Filed: October 6, 1998
    Date of Patent: September 21, 1999
    Assignees: Trustees of the University of Pennsylvania, Board of Regents of University of Nebraska
    Inventors: Michael J. Therien, Stephen DiMagno
  • Patent number: 5945572
    Abstract: 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: Grant
    Filed: October 15, 1998
    Date of Patent: August 31, 1999
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Terunori Fujita, Shigekazu Matsui, Toshihiro Takai, Hideto Matsuoka, Akifumi Kagayama, Hiroshi Kuroda, Masayasu Ishibashi, Hiroshi Iwasaki, Nobuya Hirokane
  • Patent number: 5847227
    Abstract: 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: Grant
    Filed: February 27, 1996
    Date of Patent: December 8, 1998
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Terunori Fujita, Shigekazu Matsui, Toshihiro Takai, Hideto Matsuoka, Akifumi Kagayama, Hiroshi Kuroda, Masayasu Ishibashi, Hiroshi Iwasaki, Nobuya Hirokane
  • Patent number: 5817881
    Abstract: 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: Grant
    Filed: July 30, 1997
    Date of Patent: October 6, 1998
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Paul E. Ellis, James E. Lyons, Harry K. Myers, Jr., Shahid N. Shaikh
  • Patent number: 5792890
    Abstract: 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: Grant
    Filed: February 3, 1997
    Date of Patent: August 11, 1998
    Assignee: Huntsman Specialty Chemicals Corp.
    Inventors: Pei-Shing Eugene Dai, Laurence Darrel Neff, Kyle Lee Preston, Rei-Yu Judy Hwan, John Frederick Knifton
  • Patent number: 5789627
    Abstract: 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: Grant
    Filed: February 20, 1997
    Date of Patent: August 4, 1998
    Assignee: Huntsman Specialty Chemicals Corp.
    Inventors: Rei-Yu Judy Hwan, Kyle Lee Preston
  • Patent number: 5786505
    Abstract: 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 thereby
    Type: Grant
    Filed: July 3, 1996
    Date of Patent: July 28, 1998
    Assignee: Battelle Memorial Institute
    Inventors: Donald M. Camaioni, Michael A. Lilga
  • Patent number: 5773634
    Abstract: 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: Grant
    Filed: November 14, 1996
    Date of Patent: June 30, 1998
    Assignee: Huntsman Specialty Chemicals Corporation
    Inventors: David Durham Chess, David George Pottratz, Eileen Tovan Nguyen, William Kemp Culbreth, III
  • Patent number: 5723697
    Abstract: 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: Grant
    Filed: December 29, 1995
    Date of Patent: March 3, 1998
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Manoj V. Bhinde, Thomas W. Bierl
  • Patent number: 5723677
    Abstract: 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: Grant
    Filed: June 27, 1996
    Date of Patent: March 3, 1998
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Tilak Wijesekera, James E. Lyons, Paul E. Ellis, Jr.
  • Patent number: 5710292
    Abstract: 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: Grant
    Filed: June 2, 1995
    Date of Patent: January 20, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Anton Herrmann, Joao Domingos Galamba Correia, Richard Walter Fischer
  • Patent number: 5663328
    Abstract: 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: Grant
    Filed: June 27, 1996
    Date of Patent: September 2, 1997
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Paul E. Ellis, Jr., James E. Lyons
  • Patent number: 5585515
    Abstract: 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 thereby
    Type: Grant
    Filed: April 30, 1993
    Date of Patent: December 17, 1996
    Assignee: Battelle Memorial Institute
    Inventors: Donald M. Camaioni, Michael A. Lilga
  • Patent number: 5574196
    Abstract: 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: Grant
    Filed: February 28, 1995
    Date of Patent: November 12, 1996
    Assignee: Hoechst Celanese Corporation
    Inventors: Charles E. Tucker, Diane E. Allen, Charles C. Hobbs
  • Patent number: 5563263
    Abstract: 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: Grant
    Filed: September 14, 1994
    Date of Patent: October 8, 1996
    Assignee: Hoechst Celanese Corporation
    Inventors: Thomas J. Kodadek, John F. Barry
  • Patent number: 5491265
    Abstract: 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: Grant
    Filed: February 28, 1995
    Date of Patent: February 13, 1996
    Assignee: Hoechst Celanese Corporation
    Inventors: Diane E. Allen, Charles E. Tucker, Charles C. Hobbs, Ramakrishnan Chidambaram
  • Patent number: 5489716
    Abstract: 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: Grant
    Filed: September 7, 1994
    Date of Patent: February 6, 1996
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Paul E. Ellis, Jr., James E. Lyons
  • Patent number: 5480986
    Abstract: 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: Grant
    Filed: July 30, 1993
    Date of Patent: January 2, 1996
    Assignee: Sun Company, Inc. (R&M)
    Inventors: James E. Lyons, Paul E. Ellis, Jr., Richard W. Wagner
  • Patent number: 5478962
    Abstract: 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: Grant
    Filed: February 21, 1995
    Date of Patent: December 26, 1995
    Assignee: Enichem S.p.A.
    Inventors: Laura De Nardo, Maurizio Ghirardini, Gianni Donati
  • Patent number: 5475147
    Abstract: 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: Grant
    Filed: October 19, 1994
    Date of Patent: December 12, 1995
    Assignee: ARCO Chemical Technology, L.P.
    Inventor: Thomas S. Zak
  • Patent number: 5436375
    Abstract: 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: Grant
    Filed: August 26, 1994
    Date of Patent: July 25, 1995
    Assignee: Texaco Chemical Inc.
    Inventors: Karen A. Thomas, Kyle L. Preston
  • Patent number: 5436376
    Abstract: 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: Grant
    Filed: August 11, 1994
    Date of Patent: July 25, 1995
    Assignee: Texaco Chemical Inc.
    Inventors: Yu-Hwa E. Sheu, John R. Sanderson, Mark A. Mueller, William A. Smith