Oxidation Of Organic Compound Utilizing Gaseous Oxygen Patents (Class 568/431)
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Patent number: 6252121Abstract: 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: GrantFiled: July 27, 1999Date of Patent: June 26, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: John Nicholas Argyropoulos, David Robert Bryant, Michael Leo Tulchinsky, Jeffrey Scott Kanel, Paul Foley, Barry Brent Fish
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Patent number: 6242643Abstract: 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: GrantFiled: May 13, 1997Date of Patent: June 5, 2001Assignee: Toray Industries, Inc.Inventors: Shotaro Matsuoka, Masaaki Suematsu, Akira Kitamura
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Patent number: 6169213Abstract: 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: GrantFiled: January 5, 2000Date of Patent: January 2, 2001Assignee: Consortium f{umlaut over (u)}r elektrochemische Industrie GmbHInventors: Elke Fritz-Langhals, Johannes Freudenreich, Norbert Hampp, Anton Candussio
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Patent number: 6160162Abstract: 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: GrantFiled: October 21, 1999Date of Patent: December 12, 2000Assignee: Saudi Basic Industries CorporationInventors: Khalid Karim, Yajnavalkya Subrai Bhat, Syed Irshad Zaheer, Abdullah Bin Nafisah
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Patent number: 6153779Abstract: 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: GrantFiled: June 28, 1999Date of Patent: November 28, 2000Assignee: Degussa-Huls AktiengesellschaftInventors: Martina Hess, Phalguni Chaudhuri, Karl Wieghardt
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Patent number: 6069282Abstract: 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: GrantFiled: May 21, 1998Date of Patent: May 30, 2000Assignee: Consortium fur elektrochemische Industrie GmbHInventors: Elke Fritz-Langhals, Johannes Freudenreich, Norbert Hampp, Anton Candussio
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Patent number: 6023000Abstract: 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: GrantFiled: May 21, 1998Date of Patent: February 8, 2000Assignee: Consortium fur elektrochemisch Industrie GmbHInventors: Elke Fritz-Langhals, Johannes Freudenreich
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Patent number: 5981420Abstract: 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: GrantFiled: February 17, 1998Date of Patent: November 9, 1999Assignees: Daicel Chemical Industries, Ltd., Yasutaka IshiiInventors: Tatsuya Nakano, Yasutaka Ishii
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Patent number: 5912388Abstract: 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: GrantFiled: November 12, 1997Date of Patent: June 15, 1999Assignee: Zeneca LimitedInventors: Christopher John Urch, Istvan Ettienne Marko, Masao Tuskazaki, Paul Richard Giles, Stephen Martin Brown
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Patent number: 5888787Abstract: 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: GrantFiled: July 2, 1996Date of Patent: March 30, 1999Assignee: North Carolina State UniversityInventors: Chen-Loung Chen, Josef S. Gratzl, Adrianna G. Kirkman, Antje Potthast, Thomas Rosenau
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Patent number: 5861286Abstract: 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: GrantFiled: September 25, 1997Date of Patent: January 19, 1999Assignee: V. Mane FilsInventors: Jean Mane, Joseph Zucca
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Patent number: 5831116Abstract: 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: GrantFiled: April 18, 1997Date of Patent: November 3, 1998Assignee: Northeastern UniversityInventors: Chien-Tsung Wang, Ronald J. Willey
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Patent number: 5648551Abstract: 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: GrantFiled: January 26, 1996Date of Patent: July 15, 1997Assignee: Hoechst AktiengesellschaftInventors: Holger Borchert, Thomas Gerdau, Jens Weiguny
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Patent number: 5576463Abstract: 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: GrantFiled: March 3, 1995Date of Patent: November 19, 1996Assignee: Bayer AktiengesellschaftInventors: Albert Schnatterer, Helmut Fiege
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Patent number: 5489714Abstract: 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: GrantFiled: May 22, 1995Date of Patent: February 6, 1996Assignee: PPG Industries, Inc.Inventors: Charles F. Kahle, II, Raphael O. Kollah, Gregory J. McCollum
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Patent number: 5475156Abstract: 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: GrantFiled: June 6, 1994Date of Patent: December 12, 1995Assignee: General Electric CompanyInventors: Andrew J. Caruso, Julia L. Lee
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Patent number: 5360603Abstract: 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: GrantFiled: August 23, 1993Date of Patent: November 1, 1994Assignee: Praxair Technology, Inc.Inventors: Raymond F. Drnevich, Douglas R. Dreisinger
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Patent number: 5354919Abstract: 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: GrantFiled: June 29, 1993Date of Patent: October 11, 1994Assignee: Rhone-Poulenc ChimieInventors: Michel Costantini, Dominique Laucher, Eric Fache
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Patent number: 5336779Abstract: 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: GrantFiled: September 23, 1993Date of Patent: August 9, 1994Assignee: Nippon Gohsei Kagaku Kogyo Kabushiki KaishaInventors: Toshio Yamamoto, Kazumasa Hirata, Shigenori Wakabayashi, Akio Katsuura
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Patent number: 5266291Abstract: 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: GrantFiled: May 5, 1992Date of Patent: November 30, 1993Assignee: Praxair Technology, Inc.Inventors: Raymond F. Drnevich, Douglas R. Dreisinger
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Patent number: 5232915Abstract: 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: GrantFiled: January 14, 1992Date of Patent: August 3, 1993Assignee: Schering AktiengesellschaftInventors: Eckhard Ottow, Gunter Neef, Rudolf Wiechert, Walter Elger, Sybille Beier, Karl-Heinrich Fritzemeier
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Patent number: 5183931Abstract: 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: GrantFiled: February 10, 1992Date of Patent: February 2, 1993Assignee: Phillips Petroleum CompanyInventors: Chung C. Tso, Robert L. Wynn
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Patent number: 5149880Abstract: 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: GrantFiled: August 24, 1990Date of Patent: September 22, 1992Assignee: The Texas A & M University SystemInventors: Donald T. Sawyer, Ceshing Sheu, Andrzej Sobkowiak, Hui-Chan Tung
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Patent number: 5149884Abstract: 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: GrantFiled: April 1, 1991Date of Patent: September 22, 1992Assignee: BASF AktiengesellschaftInventors: Karl Brenner, Wilhelm Ruppel, Otto Woerz, Klaus Halbritter, Hans-Juergen Scheiper, Werner Aquila, Hartwig Fuchs
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Patent number: 5136104Abstract: 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: GrantFiled: January 12, 1987Date of Patent: August 4, 1992Assignee: Nippon Shokubai Kagaku Kogyo Co. Ltd.Inventors: Noboru Saito, Isao Nakamura, Michio Ueshima, Kazuhiro Takatsu, Isao Nagai
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Patent number: 5130493Abstract: 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: GrantFiled: April 5, 1991Date of Patent: July 14, 1992Assignee: Bayer AktiengesellschaftInventors: Albert Schnatterer, Helmut Fiege, Karl-Heinz Neumann
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Patent number: 5126490Abstract: 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: GrantFiled: November 28, 1990Date of Patent: June 30, 1992Assignee: Princeton UniversityInventors: Jeffrey Schwartz, H. Eric Fischer, Jeffrey W. McMillan
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Patent number: 5082976Abstract: 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: GrantFiled: October 25, 1990Date of Patent: January 21, 1992Assignee: Bayer AktiengesellschaftInventors: Heinz U. Blank, Helmut Kraus
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Patent number: 4978802Abstract: 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: GrantFiled: December 20, 1988Date of Patent: December 18, 1990Assignee: L'Air Liquide, Societe Anonyme pour l'Etude et l'Exploitation des Procedes Georges ClaudeInventors: Philippe Campo, Panayotis Cocolios, Paul Dognin, Henry Ledon
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Patent number: 4943644Abstract: 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: GrantFiled: November 23, 1988Date of Patent: July 24, 1990Assignee: The University of FloridaInventors: Russell S. Drago, Shannon Davis
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Patent number: 4929766Abstract: 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: GrantFiled: February 16, 1989Date of Patent: May 29, 1990Assignee: Bayer AktiengesellschaftInventors: Albert Schnatterer, Helmut Fiege
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Patent number: 4863888Abstract: 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: GrantFiled: April 29, 1988Date of Patent: September 5, 1989Assignee: Amoco CorporationInventors: Judith B. Melville, L. Charles Hardy, David A. Young
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Patent number: 4816606Abstract: 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: GrantFiled: September 30, 1987Date of Patent: March 28, 1989Assignee: Basf AktiengesellschaftInventors: Karl Brenner, Manfred Eggersdorfer, Wilhelm Ruppel, Harald Schultheiss, Hans-Ulrich Scholz
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Patent number: 4700009Abstract: 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: GrantFiled: January 28, 1986Date of Patent: October 13, 1987Assignee: Hoffmann-La Roche Inc.Inventor: Nosberger, Paul
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Patent number: 4487962Abstract: 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: GrantFiled: September 27, 1982Date of Patent: December 11, 1984Assignee: BASF AktiengesellschaftInventors: Richard Krabetz, Franz Merger, Matthias Schwarzmann
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Patent number: 4390728Abstract: 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: GrantFiled: December 7, 1981Date of Patent: June 28, 1983Assignee: Ashland Oil, Inc.Inventor: Chelliah Daniel
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Patent number: 4331608Abstract: 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: GrantFiled: June 2, 1980Date of Patent: May 25, 1982Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Keiji Kawamoto, Toshihiro Yoshioka
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Patent number: 4322562Abstract: 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: GrantFiled: December 19, 1980Date of Patent: March 30, 1982Assignee: Allied CorporationInventors: Benjamin S. Tovrog, S. Elliot Diamond, Frank Mares
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Patent number: 4306083Abstract: 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: GrantFiled: May 15, 1980Date of Patent: December 15, 1981Assignee: The Dow Chemical CompanyInventor: King W. Ma
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Patent number: 4271320Abstract: 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: GrantFiled: August 31, 1979Date of Patent: June 2, 1981Assignee: Kuraray Co., Ltd.Inventors: Yasuo Tokitoh, Noriaki Yoshimura, Masuhiko Tamura
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Patent number: 4250121Abstract: 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: GrantFiled: May 24, 1979Date of Patent: February 10, 1981Assignee: Institut Francais du PetroleInventor: Hubert Mimoun
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Patent number: 4243612Abstract: 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: GrantFiled: August 13, 1979Date of Patent: January 6, 1981Assignee: Ashland Oil, Inc.Inventors: Peter E. Throckmorton, Gary E. Sitz, Robert A. Grimm
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Patent number: 4239703Abstract: 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: GrantFiled: August 1, 1979Date of Patent: December 16, 1980Assignee: Dynamit Nobel AktiengesellschaftInventors: Gunther Bernhardt, Gerhard Daum
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Patent number: 4224254Abstract: 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: GrantFiled: March 28, 1979Date of Patent: September 23, 1980Assignee: BASF AktiengesellschaftInventors: Wolfgang Sauer, Werner Fliege, Christian Dudeck, Norbert Petri
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Patent number: 4218401Abstract: 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: GrantFiled: January 11, 1974Date of Patent: August 19, 1980Assignee: The Dow Chemical CompanyInventor: C. Elmer Wymore
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Patent number: 4208352Abstract: 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: GrantFiled: December 15, 1975Date of Patent: June 17, 1980Assignee: Phillips Petroleum CompanyInventor: Lloyd E. Gardner