Oxidation Of Organic Compound Utilizing Gaseous Oxygen Patents (Class 568/431)
  • Patent number: 6252121
    Abstract: This invention relates to a process for separating one or more cyclic products from a reaction product fluid comprising one or more cyclic reactants, a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, a non-polar solvent and said one or more cyclic products, wherein said process comprises: (1) reacting said one or more cyclic reactants in the presence of said metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand and non-polar solvent to form a multiphase reaction product fluid; and (2) separating said multiphase reaction product fluid to obtain a non-polar phase comprising said one or more cyclic reactants, metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand and non-polar solvent and a polar phase comprising said one or more cyclic products.
    Type: Grant
    Filed: July 27, 1999
    Date of Patent: June 26, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John Nicholas Argyropoulos, David Robert Bryant, Michael Leo Tulchinsky, Jeffrey Scott Kanel, Paul Foley, Barry Brent Fish
  • Patent number: 6242643
    Abstract: An aromatic carboxylic acid, aromatic aldehyde, and aromatic alcohol are simultaneously and efficiently prepared by liquid phase oxidizing an aromatic compound represented by formula (I) with a gas containing molecular oxygen, in a presence of a catalyst comprising transition metal compound, tertiary amine and bromide compound:
    Type: Grant
    Filed: May 13, 1997
    Date of Patent: June 5, 2001
    Assignee: Toray Industries, Inc.
    Inventors: Shotaro Matsuoka, Masaaki Suematsu, Akira Kitamura
  • Patent number: 6169213
    Abstract: Process for the preparation of heteroaryl aldehydes or heteroaryl ketones by reaction with heteroarylmethanols with the aid of a mediator and an oxidant, wherein the mediator is selected from the group of the aliphatic, cycloaliphatic, heterocyclic or aromatic NO, and NOH containing compounds.
    Type: Grant
    Filed: January 5, 2000
    Date of Patent: January 2, 2001
    Assignee: Consortium f{umlaut over (u)}r elektrochemische Industrie GmbH
    Inventors: Elke Fritz-Langhals, Johannes Freudenreich, Norbert Hampp, Anton Candussio
  • Patent number: 6160162
    Abstract: A mixed metal oxide Mo--V--Ga--Pd--Nb--X (where X=La, Te, Ge, Zn, Si, In or W) catalytic system providing a higher selectivity to acrylic acid in the low temperature partial oxidation of propane with a molecular oxygen-containing gas.
    Type: Grant
    Filed: October 21, 1999
    Date of Patent: December 12, 2000
    Assignee: Saudi Basic Industries Corporation
    Inventors: Khalid Karim, Yajnavalkya Subrai Bhat, Syed Irshad Zaheer, Abdullah Bin Nafisah
  • Patent number: 6153779
    Abstract: Quadridentate Cu.sup.II and Zn.sup.II phenoxyl complexes and phenoxyl radical complexes thereof, in which one ligand L is bonded to each metal atom and H.sub.2 L stands for the general formula ##STR1## in which the bridge-unit Q stands for --S--, --O--, --N(R.sup.3)--, --P(R.sup.4)--, or ortho-NH--C.sub.6 H.sub.4 --NH-- and R.sup.1 and R.sup.2 stand for radical-stabilizing residues.Preferred radical complexes include ##STR2## The radical complexes are oxidation catalysts for oxidizing organic substrates with O.sub.2 in the course of which H.sub.2 O.sub.2 is also formed.
    Type: Grant
    Filed: June 28, 1999
    Date of Patent: November 28, 2000
    Assignee: Degussa-Huls Aktiengesellschaft
    Inventors: Martina Hess, Phalguni Chaudhuri, Karl Wieghardt
  • Patent number: 6069282
    Abstract: A process for the preparation of vinyl, alkynyl or aryl aldehydes or vinyl, alkynyl or aryl ketones by reaction of vinyl-, alkynyl- or aryl- methanols with the aid of a mediator and an oxidant, wherein the mediator is selected from the group of the aliphatic, cycloaliphatic, heterocyclic or aromatic NO or NOH containing compounds.
    Type: Grant
    Filed: May 21, 1998
    Date of Patent: May 30, 2000
    Assignee: Consortium fur elektrochemische Industrie GmbH
    Inventors: Elke Fritz-Langhals, Johannes Freudenreich, Norbert Hampp, Anton Candussio
  • Patent number: 6023000
    Abstract: A process for the preparation of vinyl, alkynyl or aryl aldehydes or vinyl, alkynyl or aryl ketones includes reacting vinyl-, alkynyl- and aryl- and -methylene compounds with the aid of a mediator and an oxidant, wherein the mediator is selected from the group of the aliphatic, heterocyclic or aromatic NO or NOH containing compounds.
    Type: Grant
    Filed: May 21, 1998
    Date of Patent: February 8, 2000
    Assignee: Consortium fur elektrochemisch Industrie GmbH
    Inventors: Elke Fritz-Langhals, Johannes Freudenreich
  • Patent number: 5981420
    Abstract: A substrate (e.g., a cycloalkane, a polycyclic hydrocarbon, an aromatic compound having a methyl group) is oxidized with oxygen in the presence of an oxidation catalytic system comprising an imide compound of the following formula (1) (e.g., N-hydroxyphthalimide) and a co-catalyst containing a element selected from Group 3 to 12 elements (in particular, Group 4 to 11 elements) of the Periodic Table of Elements. The co-catalyst comprises a compound containing plural elements (except heteropolyacid and a combination of Group 7 and 8 elements of the Periodic Table of Elements), and is useful for the formation of an oxide (e.g., a ketone, an alcohol, a carboxylic acid): ##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 nonaromatic 5- to 12-membered ring, X is O or OH, and n is 1 to 3.
    Type: Grant
    Filed: February 17, 1998
    Date of Patent: November 9, 1999
    Assignees: Daicel Chemical Industries, Ltd., Yasutaka Ishii
    Inventors: Tatsuya Nakano, Yasutaka Ishii
  • Patent number: 5912388
    Abstract: A process for preparing an aldehyde or ketone comprising reacting a primary or secondary alcohol with oxygen in the presence of a base, a catalytic amount of a copper salt and a suitable lignad under anhydrous conditions.
    Type: Grant
    Filed: November 12, 1997
    Date of Patent: June 15, 1999
    Assignee: Zeneca Limited
    Inventors: Christopher John Urch, Istvan Ettienne Marko, Masao Tuskazaki, Paul Richard Giles, Stephen Martin Brown
  • Patent number: 5888787
    Abstract: A method for oxidation of a pendant methyl moiety on an aromatic ring to the pendant aldehyde moiety is presented. The reaction employs laccase and the diammonium salt of 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid), and is carried out in the presence of oxygen.
    Type: Grant
    Filed: July 2, 1996
    Date of Patent: March 30, 1999
    Assignee: North Carolina State University
    Inventors: Chen-Loung Chen, Josef S. Gratzl, Adrianna G. Kirkman, Antje Potthast, Thomas Rosenau
  • Patent number: 5861286
    Abstract: The present invention relates to a process for the preparation of aromatic substances having formula (I), characterized in that a substrate having formula (II) is subjected to an oxydation in the presence of at least one protein and at least one metal ion, formula wherein R.sub.1 may be a radical --H, --CH.sub.3, --CH.sub.2 OH, --CHO, --COOH, --OCH.sub.3, or --COO--CH(COOH)--CH.sub.2 --C.sub.6 H.sub.3 (OH).sub.2 ; R.sub.2 may be a radical --H, --OH, or --OCH.sub.3 ; R.sub.3 may be a radical --H, --OH, --OCH.sub.3, or O-glucosid; R.sub.4 may be a radical --H, --OH, or --OCH.sub.3.
    Type: Grant
    Filed: September 25, 1997
    Date of Patent: January 19, 1999
    Assignee: V. Mane Fils
    Inventors: Jean Mane, Joseph Zucca
  • Patent number: 5831116
    Abstract: A process for partially oxidizing alcohols such as methanol, comprising the steps of a) introducing into a reactor unit containing a solid acid catalyst amounts of alcohol and oxygen; and a supercritical fluid (such as SCF CO.sub.2) mobile phase; and b) partially oxidizing the alcohol to its corresponding ether, aldehyde, ester or acid. In an advantageous embodiment, methanol is oxidized using an aerogel acid catalyst to produce methyl ether.
    Type: Grant
    Filed: April 18, 1997
    Date of Patent: November 3, 1998
    Assignee: Northeastern University
    Inventors: Chien-Tsung Wang, Ronald J. Willey
  • Patent number: 5648551
    Abstract: The invention relates to a process for the preparation of halobenzaldehydes of the formula (I): ##STR1## in which Hal is fluorine, chlorine, bromine or iodine and z=1, 2, 3 or 4, by catalytic gas-phase oxidation of a substituted toluene of the formula (II), ##STR2## by oxygen, which comprises carrying out the oxidation in the presence of a catalyst of the formula (III)Me.sup.1.sub.a Me.sup.2.sub.b Me.sup.3.sub.c O.sub.x (III),in which Me.sup.1 is bismuth or vanadium, Me.sup.2 is at least one of the elements selected from the group consisting of lithium, sodium, potassium, rubidium and cesium, Me.sup.3 is at least one element selected from the group consisting of iron, cobalt, nickel, niobium, molybdenum, arsenic, tin, antimony, tungsten, tantalum, phosphorus, chromium, manganese, palladium, copper, zinc, cerium, silver, boron, samarium, barium, calcium, magnesium and rhenium, and the letters a, b and c represent an atomic ratio of the respective elements such that when a=1, b has a value in the range from 0.
    Type: Grant
    Filed: January 26, 1996
    Date of Patent: July 15, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Holger Borchert, Thomas Gerdau, Jens Weiguny
  • Patent number: 5576463
    Abstract: The new process for the preparation of 2-nitrobenzaldehydes of the general formula ##STR1## in which X.sub.1 and X.sub.2 either independently of one another represent hydrogen or halogen or one of the substituents represents nitro and the other substituent then represents hydrogen,by oxidation of 2-nitrotoluenes of the general formula ##STR2## in which X.sub.1 and X.sub.2 have the meaning indicated above is characterized in that the oxidation with oxygen or an oxygen-containing gas is carried out in the presence of at least one alkoxyalkylamine as a solvent and in the presence of strong bases.
    Type: Grant
    Filed: March 3, 1995
    Date of Patent: November 19, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albert Schnatterer, Helmut Fiege
  • Patent number: 5489714
    Abstract: Described is a method of preparing dinitrobis(hydroxymethyl)benzene, useful as a photoreactive monomer, from a derivative of stilbene. Also disclosed is a novel dinitrocarbomethoxybenzaldehyde compound useful as an intermediate.
    Type: Grant
    Filed: May 22, 1995
    Date of Patent: February 6, 1996
    Assignee: PPG Industries, Inc.
    Inventors: Charles F. Kahle, II, Raphael O. Kollah, Gregory J. McCollum
  • Patent number: 5475156
    Abstract: A method is provided for converting a 2,4,6-trialkylphenol, such as mesitol, to a dialkylphenol, for example 2,6-dimethylphenol, by effecting the selective oxidation of the 2,4,6-trialkylphenol, followed by the deformylation of the resulting 3, 5-dialkyl-4-hydroxybenzaldehyde.
    Type: Grant
    Filed: June 6, 1994
    Date of Patent: December 12, 1995
    Assignee: General Electric Company
    Inventors: Andrew J. Caruso, Julia L. Lee
  • Patent number: 5360603
    Abstract: The present invention relates to processes and apparatus for mixing oxidizable reactants with oxidant and/or oxidizing oxidizable reactants. Through using particular mixing and/or oxidizing arrangements, the risk of flammable or explosive reactions can be significantly reduced or prevented. When ammonia is used as the reactant, nitric acid can be obtained.
    Type: Grant
    Filed: August 23, 1993
    Date of Patent: November 1, 1994
    Assignee: Praxair Technology, Inc.
    Inventors: Raymond F. Drnevich, Douglas R. Dreisinger
  • Patent number: 5354919
    Abstract: Aromatic compounds bearing oxidizable alkyl substituents, e.g., alkoxylated and/or hydroxylated such substrates, notably the phenolics/cresols, are selectively oxidized, e.g., into hydroxybenzaldehydes, by reacting same with appropriate oxidizing agents, in an aqueous reaction medium, in the presence of a catalytically effective amount of a solid, palladium-containing oxidation catalyst (optionally containing a cocatalytically effective amount of tin, germanium, tellurium and/or copper).
    Type: Grant
    Filed: June 29, 1993
    Date of Patent: October 11, 1994
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Costantini, Dominique Laucher, Eric Fache
  • Patent number: 5336779
    Abstract: In producing formylimidazoles by catalytically oxidizing the corresponding 4- or 5-hydroxymethylimidazoles, the catalytic oxidation is carried out in the presence of a noble metal catalyst while oxygen or air is blown into the reaction system. In this case, it is particularly desirable that the catalytic oxidation in the presence of a noble metal catalyst be carried out in a solvent comprising an aqueous alkali or in a mixed solvent composed of an aqueous alkali and an organic solvent immiscible with water.
    Type: Grant
    Filed: September 23, 1993
    Date of Patent: August 9, 1994
    Assignee: Nippon Gohsei Kagaku Kogyo Kabushiki Kaisha
    Inventors: Toshio Yamamoto, Kazumasa Hirata, Shigenori Wakabayashi, Akio Katsuura
  • Patent number: 5266291
    Abstract: The present invention relates to processes and apparatus for mixing oxidizable reactants with oxidant and oxidizing oxidizable reactants. When ammonia is used as the reactant, nitric acid can be obtained. Through using particular mixing and oxidizing arrangements, the volume of reactant oxidized can be significantly increased.
    Type: Grant
    Filed: May 5, 1992
    Date of Patent: November 30, 1993
    Assignee: Praxair Technology, Inc.
    Inventors: Raymond F. Drnevich, Douglas R. Dreisinger
  • Patent number: 5232915
    Abstract: 9.alpha.-Hydroxy-19,11.beta.-bridged steroids of general formula I ##STR1## are described. The more detailed meaning of A, B, R.sup.1, R.sup.2, G, Z, R.sup.4 --Y and R.sup.4' --Y' follows from the description. The steroids of general formula I have antigestagen and/or antiglucocorticoidal action and can be used for the production of pharmaceutical agents.
    Type: Grant
    Filed: January 14, 1992
    Date of Patent: August 3, 1993
    Assignee: Schering Aktiengesellschaft
    Inventors: Eckhard Ottow, Gunter Neef, Rudolf Wiechert, Walter Elger, Sybille Beier, Karl-Heinrich Fritzemeier
  • Patent number: 5183931
    Abstract: Oxidation of alkylaromatics having a benzylic hydrogen atom is catalyzed by a catalyst comprising a palladium salt, a metal persulfate, a third metal salt, and a tin salt in a carboxylic acid for a period of time sufficient to convert the alkylaromatics to their corresponding oxidized derivatives. The catalyst is prepared by preheating the palladium salt and the metal persulfate at a temperature sufficient to provide the desired catalytic activity followed by additon of the third metal salt and the tin salt.
    Type: Grant
    Filed: February 10, 1992
    Date of Patent: February 2, 1993
    Assignee: Phillips Petroleum Company
    Inventors: Chung C. Tso, Robert L. Wynn
  • Patent number: 5149880
    Abstract: Nitrogen-containing aromatic heterocyclic ligand-metal complexes and their use for the activation of hydrogen peroxide and dioxgen are disclosed. Processes whereby activated hydrogen peroxide or dioxygen are used to transform various organic substrates are also disclosed. In particular, processes for the conversion of methylenic carbons to carbonyls, for the dioxygenation of aryl olefins, acetylenes and aryl-.alpha.-diols, for the oxidation of alcohols and aldehydes and for the removal of mercaptans from gaseous streams and for the removal of hydrogen sulfide and/or mercaptans from liquid streams are disclosed.
    Type: Grant
    Filed: August 24, 1990
    Date of Patent: September 22, 1992
    Assignee: The Texas A & M University System
    Inventors: Donald T. Sawyer, Ceshing Sheu, Andrzej Sobkowiak, Hui-Chan Tung
  • Patent number: 5149884
    Abstract: In a tube bundle reactor for carrying out catalytic organic reactions in the gas phase, comprising reaction tubes (A) arranged between tubesheets (B), the reaction tubes have an inside diameter ranging from 0.5 to 3 cm, the ratio of reaction tube length to inside diameter ranges from 2 to 10, and the reaction tubes (A) are surrounded by a fluid heat transport medium flowing in the crosswise direction; said tube bundle reactor is useful in particular in exothermic organic reactions.
    Type: Grant
    Filed: April 1, 1991
    Date of Patent: September 22, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Karl Brenner, Wilhelm Ruppel, Otto Woerz, Klaus Halbritter, Hans-Juergen Scheiper, Werner Aquila, Hartwig Fuchs
  • Patent number: 5136104
    Abstract: From a methoxy-, tertiary butyl-, or phenoxy-substituted toluene, a corresponding substituted benzaldehyde is obtained by the catalytic gas-phase oxidation of the substituted toluene with a molecular oxygen-containing gas in the presence of a catalyst composition represented by the formula, V.sub.a X.sub.b Y.sub.c O.sub.d, wherein X stands for at least one element from among Na, K, Rb, Cs, and Tl (with the exception of a case wherein K is used alone), Y for at least one element from among Mg, Ca, Sr, Ba, Nb, Ta, P, Sb, Bi, Cu, Ag, Ti, Fe, Co, Ni, Sn, Ce, and Zn, and a, b, c, and d jointly represent an atomic ratio of the relevant elements.
    Type: Grant
    Filed: January 12, 1987
    Date of Patent: August 4, 1992
    Assignee: Nippon Shokubai Kagaku Kogyo Co. Ltd.
    Inventors: Noboru Saito, Isao Nakamura, Michio Ueshima, Kazuhiro Takatsu, Isao Nagai
  • Patent number: 5130493
    Abstract: o-Hydroxy-benzaldehydes can be obtained by oxidation of the o-cresols, on which they are based, with oxygen in the presence of substances having a base reaction in a solvent if chelate complexes of iron, manganese or a mixuture of both with polyaza-macrocycles as chelating agents are employed as catalysts. Copper or a copper compound is advantageously added as a co-catalyst.
    Type: Grant
    Filed: April 5, 1991
    Date of Patent: July 14, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albert Schnatterer, Helmut Fiege, Karl-Heinz Neumann
  • Patent number: 5126490
    Abstract: A process is disclosed for the catalytic oxydation of olefins to carbonyl compounds with molecular oxygen at elevated temperatures in the presence of rhodium oxide on a support. The process is applicable to a broad variety of olefins and is not limited to special olefins and forms especially ketones in a high selectivity.
    Type: Grant
    Filed: November 28, 1990
    Date of Patent: June 30, 1992
    Assignee: Princeton University
    Inventors: Jeffrey Schwartz, H. Eric Fischer, Jeffrey W. McMillan
  • Patent number: 5082976
    Abstract: Benzaldehydes of the formula ##STR1## can be obtained by reaction of substituted .beta.-amino-styrenes of the formula ##STR2## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.8, R.sup.9, R.sup.10, m, n and o have the scope of meaning indicated in the description, with oxygen in the presence of a Cu compound in the solution of an aprotic polar solvent at 0.degree.-120.degree. C.
    Type: Grant
    Filed: October 25, 1990
    Date of Patent: January 21, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz U. Blank, Helmut Kraus
  • Patent number: 4978802
    Abstract: Aromatic aldehydes are produced by oxidation with oxygen of a para-cresol derivative in a solvent, in the presence of a base and a catalytic amount of a cobalt compound. The catalyst is a chelated complex of cobalt with a rigid structure that is slightly oxidizable selected from the group consisting of bis-(4-methylpyridine isoindolinato)cobalt(II) acetate, phthalocyaninatocobalt(II), and sulfophthalocyaninanatocobalt(II). The process is particularly suited to the production of p-hydroxy benzaldehydes.
    Type: Grant
    Filed: December 20, 1988
    Date of Patent: December 18, 1990
    Assignee: L'Air Liquide, Societe Anonyme pour l'Etude et l'Exploitation des Procedes Georges Claude
    Inventors: Philippe Campo, Panayotis Cocolios, Paul Dognin, Henry Ledon
  • Patent number: 4943644
    Abstract: A method of oxidizing olefins or alkanes by contacting with oxygen and a catalyst composition of the formula:Ru.sub.3 O[OCO(CF.sub.2).sub.y CF.sub.3 ].sub.6 LWherein: Ru are reuthenium atoms having a formal oxidation state of +2 or +3,L is a neutral or anionic ligand,Y is an integer from 0 to 6, andx is an integer from 1 to 3; and an anion.
    Type: Grant
    Filed: November 23, 1988
    Date of Patent: July 24, 1990
    Assignee: The University of Florida
    Inventors: Russell S. Drago, Shannon Davis
  • Patent number: 4929766
    Abstract: p-Hydroxy-benzaldehydes can be obtained by oxidation of the corresponding p-cresols with oxygen in the presence of basic substances in a solvent, the reaction being carried out in the additional presence of a chelate complex of iron and/or manganese. If desired, the reaction can be carried out in the presence of further metal salts.
    Type: Grant
    Filed: February 16, 1989
    Date of Patent: May 29, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albert Schnatterer, Helmut Fiege
  • Patent number: 4863888
    Abstract: The preparation, structure, and properties of solid inorganic materials containing cobalt, boron, oxygen and, optionally, aluminum, is described. Also described is the use of such materials in catalytic compositions for the conversion of organic compounds. In particular, the new material Co(BO.sub.2)OH is described as well as the use of such material in various catalyzed processes including oxidation of organic compound processes. A particularly useful process is a heterogeneous catalyzed partial oxidation of an alkylaromatic followed by complete oxidation to an aromatic polycarboxlic acid in a water phase.
    Type: Grant
    Filed: April 29, 1988
    Date of Patent: September 5, 1989
    Assignee: Amoco Corporation
    Inventors: Judith B. Melville, L. Charles Hardy, David A. Young
  • Patent number: 4816606
    Abstract: Aldehydes and ketones of the general formula I ##STR1## where R.sup.1 is hydrogen or an organic radical of 1 to n carbon atoms and R.sup.2 is a non-aromatic organic radical of 1 to m carbon atoms, (m+n) ranging from 2 to 24 and R.sup.1 and R.sup.2 being combinable to form a 4- to 12-membered ring, are prepared in a continuous manner by oxidizing an alcohol of the general formula II ##STR2## with oxygen or an oxygen-containing gas at elevated temperatures in the gas phase in the presence of a catalyst, by effecting the oxidation by means of a supported catalyst composed of an inert carrier having a smooth surface and from 0.1 to 20% by weight, based on the amount of carrier, of an active layer of copper, silver and/or gold in a tubular reactor or tube bundle reactor where the internal diameter D of the tube or tubes ranges from 10 to 50 mm and the largest diameter d of the coated supported catalysts is subject to the relationship d=from 0.1 to 0.2 D.
    Type: Grant
    Filed: September 30, 1987
    Date of Patent: March 28, 1989
    Assignee: Basf Aktiengesellschaft
    Inventors: Karl Brenner, Manfred Eggersdorfer, Wilhelm Ruppel, Harald Schultheiss, Hans-Ulrich Scholz
  • Patent number: 4700009
    Abstract: The present disclosure is concerned with a novel process for the manufacture of substituted benzaldehydes, namely of benzaldehydes of the formula ##STR1## wherein R represents a methoxy or tert.butyl group. The compounds of formula I are known substances, useful as, e.g. intermediates.
    Type: Grant
    Filed: January 28, 1986
    Date of Patent: October 13, 1987
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Nosberger, Paul
  • Patent number: 4487962
    Abstract: An oxidation catalyst wherein the catalytically active component has the general formulaMo.sub.12 P.sub.a Rh.sub.b Cu.sub.c V.sub.d Cs.sub.e X.sub.f Y.sub.g Z.sub.h O.sub.x,where X is Cr and/or Fe, Y is Nb, Z is Na, Li, K and/or Rb, a is 0.1-4, b is 0.001-1, c is 0.05-2, d is 0.05-4, e is 0.1-5, f is 0-2, g is 0-3 and h is 0-2, and x is the number of oxygen atoms required to saturate the valencies of the other constituents, is very suitable for the preparation of methacrylic acid by gas phase oxidation of methacrolein with an oxygen-containing and steam-containing gas mixture.
    Type: Grant
    Filed: September 27, 1982
    Date of Patent: December 11, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Richard Krabetz, Franz Merger, Matthias Schwarzmann
  • Patent number: 4390728
    Abstract: Benzaldehyde is prepared by the oxidation of toluene in the presence of a catalyst composed of the oxides of copper, iron, uranium, lead, tellurium, molybdenum, and phosphorous which can also include some other promoter elements.
    Type: Grant
    Filed: December 7, 1981
    Date of Patent: June 28, 1983
    Assignee: Ashland Oil, Inc.
    Inventor: Chelliah Daniel
  • Patent number: 4331608
    Abstract: Unsaturated compounds having at least 4 carbon atoms, including unsaturated alicyclic compounds having at least 4 carbon atoms, unsaturated aliphatic compounds having at least one carbon-carbon unsaturated bond and having at least 4 carbon atoms and unsaturated aromatic compounds having at least one carbon-carbon unsaturated bond in the branched chain thereof and (ii) aldehydes or ketones having at least 4 carbon atoms are catalytically co-oxidized with an oxygen-containing gas in a liquid phase to form a cleaveged product or products of unsaturated bond of the unsaturated compounds at a high yield. This co-oxidation reaction is carried out in the presence of a heavy metal containing iron, cobalt, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum, copper, silver, chromium, molybdenum, tungsten, manganese and rhenium and the compounds thereof.
    Type: Grant
    Filed: June 2, 1980
    Date of Patent: May 25, 1982
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Keiji Kawamoto, Toshihiro Yoshioka
  • Patent number: 4322562
    Abstract: An oxidation process in which a metal nitro complex transfers an oxygen atom from the nitro ligand to a substrate; especially such process conducted cyclically or catalytically using molecular oxygen as the oxygen source. Metal nitrosyl complex is formed as a coproduct together with an oxidation product of the substrate. In a cyclic process, nitrosyl ligand of the metal nitrosyl coproduct is reoxidized by molecular oxygen in presence of a monodentate base such as pyridine to nitro ligand; and the nitro complex, thus regenerated, can be used again to oxidize the substrate. In a catalytic process, using an activator such as a Lewis acid with alcohols or divalent palladium with olefins, elemental oxygen maintains a concentration of nitro ligand in the reaction mixture. In particular the metal is a Group VIII metal, especially cobalt and the ligand is saloph or tetraphenylporphyrin.
    Type: Grant
    Filed: December 19, 1980
    Date of Patent: March 30, 1982
    Assignee: Allied Corporation
    Inventors: Benjamin S. Tovrog, S. Elliot Diamond, Frank Mares
  • Patent number: 4306083
    Abstract: In a two-phase liquid medium comprising an aqueous alkaline solution and an organic solvent, molecular oxygen and a noble metal-containing catalyst can be used to oxidize aryl-substituted alcohols of the formula AR(--CH.dbd.CH--).sub.n CH.sub.2 OH wherein n is 0, 1 or 2, to the corresponding aldehydes. More specifically, the oxidation of an aromatic alcohol, such as p-methoxybenzyl alcohol, can be efficiently carried out in a multiphase system comprising a 5 percent palladium-on-charcoal catalyst, an organic solvent such as methylene chloride, in contact with an aqueous sodium hydroxide solution, in the presence of air or oxygen with good agitation followed by separation of the two phases, recovery of the aldehyde product from the organic solvent and recycle of the aqueous phase without neutralization.
    Type: Grant
    Filed: May 15, 1980
    Date of Patent: December 15, 1981
    Assignee: The Dow Chemical Company
    Inventor: King W. Ma
  • Patent number: 4271320
    Abstract: An industrially suitable process for producing a higher carbonyl compound by the oxidation of an olefinic compound having at least six carbon atoms is provided. Said improved process comprises oxidizing the olefinic compound in aqueous medium containing palladium or salt thereof and a copper salt in the presence of a specific water-soluble polyoxyalkylene compound in an amount of from about 1/4 to about 3 parts by weight per 1 part by weight of water contained in the reaction mixture. The improvement is demonstrated in terms of yield, selectivity, separation of the product, and recycle of the catalyst.
    Type: Grant
    Filed: August 31, 1979
    Date of Patent: June 2, 1981
    Assignee: Kuraray Co., Ltd.
    Inventors: Yasuo Tokitoh, Noriaki Yoshimura, Masuhiko Tamura
  • Patent number: 4250121
    Abstract: Carbonyl compounds are manufactured by oxidizing alcohols or polyalcohols with molecular oxygen in the presence of a catalyst which comprises ruthenium salts or complexes associated with copper or iron salts or complexes.
    Type: Grant
    Filed: May 24, 1979
    Date of Patent: February 10, 1981
    Assignee: Institut Francais du Petrole
    Inventor: Hubert Mimoun
  • Patent number: 4243612
    Abstract: A vapor phase process for the direct oxidation of a methyl benzene to the corresponding aldehyde derivative; e.g., conversion of toluene to benzaldehyde, wherein said oxidation is effected in the presence of a catalyst system consisting essentially of uranium and molybdenum oxides in combination with an oxide of lead, tin, zirconium, cadmium, antimony or nickel.
    Type: Grant
    Filed: August 13, 1979
    Date of Patent: January 6, 1981
    Assignee: Ashland Oil, Inc.
    Inventors: Peter E. Throckmorton, Gary E. Sitz, Robert A. Grimm
  • Patent number: 4239703
    Abstract: A process for the preparation of a terephthalic, isophthalic or phthalic dialdehyde is described by dehydrogenation of the corresponding xylylene glycol in the vapor phase at 250.degree. to 500.degree. C. The process is carried out in the presence of oxygen, water vapor and a dehydrogenation catalyst, suitably a silver dehydrogenation catalyst.
    Type: Grant
    Filed: August 1, 1979
    Date of Patent: December 16, 1980
    Assignee: Dynamit Nobel Aktiengesellschaft
    Inventors: Gunther Bernhardt, Gerhard Daum
  • Patent number: 4224254
    Abstract: Aromatic and araliphatic aldehydes are prepared by oxidizing corresponding alcohols with oxygen in the presence of a silver catalyst of a defined particle size, and under defined temperature conditions. The products are starting materials for the preparation of dyes, pesticides, plastics and scents.
    Type: Grant
    Filed: March 28, 1979
    Date of Patent: September 23, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Sauer, Werner Fliege, Christian Dudeck, Norbert Petri
  • Patent number: 4218401
    Abstract: Primary and secondary alcohols are oxidized to aldehydes and ketones, respectively, by passing a gaseous mixture of the alcohol and oxygen (air) over a supported catalyst of Ru, Rh, Pd, Pt, Ir or Os. The catalyst is improved by admixture with a tin compound. The support for the catalyst is preferably alumina, silicon carbide or other inert material having a low surface to weight ratio. Preferred conditions are atmospheric pressure, about 250.degree.-500.degree. C. and a space velocity of 1000-4000/hr. Preferred alcohols are isopropanol, 1-methoxy-2-propanol and ethanol.
    Type: Grant
    Filed: January 11, 1974
    Date of Patent: August 19, 1980
    Assignee: The Dow Chemical Company
    Inventor: C. Elmer Wymore
  • Patent number: 4208352
    Abstract: A process is provided for oxygenating alkyl-substituted aromatic compounds. Alkyl-substituted aromatic compounds in the liquid phase are contacted with molecular oxygen at a temperature below 200.degree. C. in the presence of a catalyst system which is substantially insoluble in the reaction mixture at reaction conditions. The catalyst components are a suspended copper compound and a suspended bromine compound which preferably are associated with a major quantity of a suitable catalyst support material. Optionally, the reaction can be carried out in the presence of minor amounts of acetic acid, acetic anhydride or suitable inorganic nitrate compounds.
    Type: Grant
    Filed: December 15, 1975
    Date of Patent: June 17, 1980
    Assignee: Phillips Petroleum Company
    Inventor: Lloyd E. Gardner