Molecular Oxygen Utilized Patents (Class 568/802)
  • Patent number: 11075318
    Abstract: A method for film-forming a buffer layer to be used for a solar cell, the buffer layer being disposed between a light absorbing layer and a transparent conductive film. Specifically, in this buffer layer film-forming method, a solution is formed into a mist, the solution containing zinc and almuminum as metal raw materials of the buffer layer. Then, a substrate disposed in the atmosphere is heated. Then, the mist of the solution is sprayed to the substrate being heated.
    Type: Grant
    Filed: May 22, 2014
    Date of Patent: July 27, 2021
    Assignee: TOSHIBA MITSUBISHI-ELECTRIC INDUSTRIAL SYSTEMS CORPORATION
    Inventors: Takahiro Shirahata, Hiroyuki Orita, Takahiro Hiramatsu, Hiroshi Kobayashi
  • Patent number: 8772552
    Abstract: The present invention provides an improved process for the selective hydroxylation of benzene. The process provides a direct single step selective vapor phase hydroxylation of benzene to phenol using molecular oxygen (air) over Cu—Cr oxide catalysts. The process provides benzene conversion of 10 to 45% and selectivity for phenol up to 100%.
    Type: Grant
    Filed: September 20, 2012
    Date of Patent: July 8, 2014
    Assignee: Council of Scientific & Industrial Research
    Inventors: Rajaram Bal, Shubhra Acharyya Shankha, Shilpi Ghosh, Bipul Sarkar, Karan Singh Rawat, Chandrashekar Pendem
  • Patent number: 8729315
    Abstract: Process for the production in continuous or semi-continuous of phenol/acetone from cumene, via cumene hydroperoxide (CHP), which comprises: a. producing CHP in an air-lift reactor in which at least the upper and/or lower part of the downcomer has a flaring; b. cleaving the cumene hydroperoxide by means of acid treatment in a loop reactor comprising two heat exchangers connected in series and wherein the feedings of CHP and fresh acetone are in pairs and each pair is positioned up-stream of each exchanger.
    Type: Grant
    Filed: October 29, 2010
    Date of Patent: May 20, 2014
    Assignee: Versalis S.p.A.
    Inventors: Mauro Burattini, Roberto Bagatin
  • Publication number: 20130096351
    Abstract: The present invention provides an improved process for the selective hydroxylation of benzene. The process provides a direct single step selective vapour phase hydroxylation of benzene to phenol using molecular oxygen (air) over Cu—Cr oxide catalysts. The process provides benzene conversion of 10 to 45% and selectivity for phenol up to 100%.
    Type: Application
    Filed: September 20, 2012
    Publication date: April 18, 2013
    Applicant: Council of Scientific & Industrial Research
    Inventor: Council of Scientific & Industrial Research
  • Publication number: 20120252999
    Abstract: Systems and methods of producing chemical compounds are disclosed. An example chemical production system includes a combustion chamber having intake ports for entry of a gas mixture. An igniter ignites the gas mixture in the intake chamber to facilitate a reaction at a high temperature and high pressure. A nozzle restricts exit of the ignited gas mixture from the combustion chamber. An expansion chamber cools the ignited gas. The expansion chamber has an exhaust where the cooled gas exits the expansion chamber. A chemical compound product is formed in the expansion chamber.
    Type: Application
    Filed: April 12, 2012
    Publication date: October 4, 2012
    Inventor: Bruce H. Peters
  • Patent number: 8247622
    Abstract: A process is described for the preparation of phenol by the hydrodeoxygenation of polyhydroxylated benzene derivatives or by the selective hydroxylation of benzene under depletive conditions, characterized in that the above-mentioned reactions are carried out in the presence of a catalyst based on multi component metal oxides comprising at least one metal selected from the groups VB, VIB, VIII, IB, IIB, IVA, VA.
    Type: Grant
    Filed: October 20, 2010
    Date of Patent: August 21, 2012
    Assignee: Polimeri Europa S.p.A.
    Inventors: Leonardo Dalloro, Alberto Cesana, Roberto Buzzoni, Fausto Genoni, Guido Spano, Franco Rivetti
  • Patent number: 8017822
    Abstract: An integrated process for producing aromatic hydrocarbons and ethylene and/or propylene and optionally other lower olefins from low molecular weight hydrocarbons, preferably methane, which comprises: (a) contacting at least one low molecular weight alkane, preferably methane, with a halogen, preferably bromine, under process conditions sufficient to produce a monohaloalkane, preferably monobromomethane, (b) reacting the monohaloalkane in the presence of a coupling catalyst to produce aromatic hydrocarbons and C2+ alkanes, (c) separating the aromatic hydrocarbons from the product mixture of step (b) to produce aromatic hydrocarbons, and (d) cracking at least part of the C2+ alkanes in an alkane cracking system to produce ethylene and/or propylene and optionally other lower olefins.
    Type: Grant
    Filed: October 5, 2009
    Date of Patent: September 13, 2011
    Assignee: Shell Oil Company
    Inventors: Howard Lam Ho Fong, Richard Dale Swain
  • Publication number: 20110092746
    Abstract: A process is described for the preparation of phenol by the hydrodeoxygenation of polyhydroxylated benzene derivatives or by the selective hydroxylation of benzene under depletive conditions, characterized in that the above-mentioned reactions are carried out in the presence of a catalyst based on multi component metal oxides comprising at least one metal selected from the groups VB, VIB, VIII, IB, IIB, IVA, VA.
    Type: Application
    Filed: October 20, 2010
    Publication date: April 21, 2011
    Applicant: POLIMERI EUROPA S.p.A.
    Inventors: Leonardo DALLORO, Alberto Cesana, Roberto Buzzoni, Fausto Genoni, Guido Spano, Franco Rivetti
  • Publication number: 20100234637
    Abstract: An integrated process for producing aromatic hydrocarbons and ethylene and/or propylene and optionally other lower olefins from low molecular weight hydrocarbons, preferably methane, which comprises: (a) contacting one or more low molecular weight alkanes, preferably methane, with a halogen, preferably bromine, under process conditions sufficient to produce a monohaloalkane, preferably monobromomethane, (b) reacting a first portion of the monohaloalkane in the presence of a coupling catalyst under process conditions sufficient to produce aromatic hydrocarbons and C2-5 alkanes, (c) separating the aromatic hydrocarbons from the product mixture of step (b) to produce aromatic hydrocarbons, (d) reacting a second portion of the monohaloalkane in the presence of a coupling catalyst under process conditions sufficient to produce ethylene and/or propylene.
    Type: Application
    Filed: March 15, 2010
    Publication date: September 16, 2010
    Inventors: Howard Lam Ho FONG, Richard Dale Swain
  • Publication number: 20100087686
    Abstract: An integrated process for producing aromatic hydrocarbons and ethylene and/or propylene and optionally other lower olefins from low molecular weight hydrocarbons, preferably methane, which comprises: (a) contacting at least one low molecular weight alkane, preferably methane, with a halogen, preferably bromine. under process conditions sufficient to produce a monohaloalkane, preferably monobromomethane, (b) reacting the monohaloalkane in the presence of a coupling catalyst to produce aromatic hydrocarbons and C2+ alkanes, (c) separating the aromatic hydrocarbons from the product mixture of step (b) to produce aromatic hydrocarbons, and (d) cracking at least part of the C2+ alkanes in an alkane cracking system to produce ethylene and/or propylene and optionally other lower olefins.
    Type: Application
    Filed: October 5, 2009
    Publication date: April 8, 2010
    Inventors: Howard Lam Ho FONG, Richard Dale SWAIN
  • Publication number: 20090234121
    Abstract: The synthesis of discrete, air, protic, and thermally stable transition metal NNC complexes that catalyze the CH activation and functionalization of alkanes and arenes is disclosed. Methods for the selective conversion of methane to methanol or methyl esters in acidic and neutral media are disclosed.
    Type: Application
    Filed: January 15, 2009
    Publication date: September 17, 2009
    Inventors: Roy A. Periana, William A. Goddard, III, Jonas Oxgaard, Kenneth Young
  • Patent number: 7091386
    Abstract: A catalytic process for the oxidation of organic. Oxygen is loaded into a metal foil by heating the foil while in contact with an oxygen-containing fluid. After cooling the oxygen-activated foil to room temperature, oxygen diffuses through the foil and oxidizes reactants exposed to the other side of the foil.
    Type: Grant
    Filed: May 3, 2004
    Date of Patent: August 15, 2006
    Assignee: U.S. Department of Energy
    Inventors: Robert J. Beuhler, Michael G. White, Jan Hrbek
  • Patent number: 6936740
    Abstract: Phenol is formed by reaction of oxidant and benzene over a solid catalyst such as Pd on TS-1, the reaction being carried out in carbon dioxide solvent at conditions effective to provide a dense phase reaction mixture.
    Type: Grant
    Filed: August 19, 2004
    Date of Patent: August 30, 2005
    Assignee: ARCO Chemical Technology, L.P.
    Inventors: Robert N. Cochran, Jay F. Miller, Eric John Beckman, Sarah Emma Jones
  • Patent number: 6911563
    Abstract: A method for carrying out a reaction of one substance capable of being activated by a catalyst with another substance capable of reacting with said one substance activated, characterized in that the substance capable of being activated is activated by passing the substance through a diaphragm type catalyst and the reaction is thus performed in one reaction step; a method for producing an aromatic alcohol utilizing the above method; and a reaction apparatus suitable for these reactions. In the method, one substance is activated by passing through a diaphragm type catalyst and an objective reaction is carried out by using the activated substance, and the reaction can be performed in one reaction step and with safety. Moreover, the contact of the above activated substance with a compound to be reacted therewith can be freely controlled, and therefore, over-reaction can be prevented and an objective product can be produced in high yield.
    Type: Grant
    Filed: December 27, 2001
    Date of Patent: June 28, 2005
    Assignees: National Institute of Advanced Industrial Science, NOK Corporation
    Inventors: Fujio Mizukami, Shuichi Niwa, Makoto Toba, Naotsugu Itoh, Tomonari Saito, Takemi Nanba, Hiroshi Shoji, Kazuhiko Haba
  • Patent number: 6900358
    Abstract: A process for hydroxylating benzene under catalytic distillation conditions to produce hydroxylated products such as phenol is provided. The process provides for direct hydroxylation of liquid phase benzene with an oxidant and a zeolite catalyst under conditions effective to prevent coke formation on the catalyst.
    Type: Grant
    Filed: April 24, 2001
    Date of Patent: May 31, 2005
    Assignee: Shell Oil Company
    Inventor: David Morris Hamilton, Jr.
  • Patent number: 6768013
    Abstract: A novel process for the direct oxidation of hydrogen and hydrocarbons is disclosed, where the explosion risks inherent in gas phase oxidations are substantially eliminated. Gaseous oxidation reactants are soluble in a first reaction solvent phase such as a perfluorocarbon (e.g. C8F18) and the oxidation product is preferentially soluble in a second product solvent phase such as water or a dilute acid. A solid catalyst such as palladium on alumina is then contacted with the dissolved reactants. The oxidation product such as hydrogen peroxide may be separated from the reaction solvent phase by extraction into the immiscible product solvent phase and then separated from it by distillation, thereby allowing re-use of the aqueous phase. The present invention may be carried out using a two-phase reaction system whereby both the reaction solvent and product solvent are contained within a reaction vessel into which the solid catalyst is slurried and mechanically agitated to promote the reaction.
    Type: Grant
    Filed: June 15, 2001
    Date of Patent: July 27, 2004
    Assignee: UOP LLC
    Inventor: Peter R. Pujado
  • Patent number: 6646167
    Abstract: Benzene, ascorbic acid acting as a reducing agent, and a vanadium-supported alumina catalyst are placed in an aqueous solution of acetic acid used as a solvent, and the reaction is carried out under an oxygen gas atmosphere having a pressure of at least 0.3 MPa so as to directly oxidize benzene and, thus, to obtain phenol at a high yield of at least 8%.
    Type: Grant
    Filed: September 25, 2001
    Date of Patent: November 11, 2003
    Assignee: President of Kobe University
    Inventor: Shigeru Tsuruya
  • Publication number: 20030171625
    Abstract: A process produces an aromatic compound by bringing an aromatic compound (B) into contact with molecular oxygen (C) in the presence of a catalyst (A) comprising at least one of (A1) a heteropolyacid and/or a salt thereof, and (A2) a mixture of oxoacids and/or salts thereof containing, as a whole, one of P and Si and at least one selected from V, Mo and W to thereby yield another aromatic compound (G) than the aromatic compound (B). The process can produce, for example, a corresponding aromatic hydroxy compound (G1) by allowing the aromatic compound (B) to react with the molecular oxygen (C) further in the presence of a reducing agent (D).
    Type: Application
    Filed: March 6, 2003
    Publication date: September 11, 2003
    Inventors: Yasutaka Ishii, Tatsuya Nakano
  • Publication number: 20030050515
    Abstract: A method for producing biphenols by oxidative coupling of dialkylphenols which proceeds in two stages using a copper amine complex which is catalytically effective in each stage is disclosed. A novel copper amine complex is also disclosed wherein the complex exhibits high catalytic activity for the oxidative coupling of substituted phenols under mild conditions, has dual (two stage) activity and can be readily recycled and reused.
    Type: Application
    Filed: August 26, 2002
    Publication date: March 13, 2003
    Inventor: Gregory Kaplan
  • 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: 6479705
    Abstract: A process for preparing a ketone, an alcohol and/or a hydroperoxide is provided by reacting a hydrocarbon with molecular oxygen in the presence of a cyclic N-hydroxyimide and a compound of a transition metal, in which an oxygen-containing gas is supplied in a reaction system and at the same time a gas containing 1 to-about 8.59, by volume of oxygen is discharged from the reaction system. This process is excellent in productivity and safety and produces the desired products at a high selectivity.
    Type: Grant
    Filed: December 14, 2000
    Date of Patent: November 12, 2002
    Assignees: Sumitomo Chemical Company, Limited, Daicel Chemical Industries, Ltd.
    Inventors: Shuzo Murata, Nobuhiro Tani, Hiroyuki Asano
  • Patent number: 6459002
    Abstract: Cyclohexanone, cyclohexanol and/or cyclohexyl hydroperoxide are prepared at a high productivity by allowing cyclohexane to be in contact with an oxygen-containing gas using a catalyst comprising a cyclic N-hydroxyimide and a transition metal compound in the presence of cyclohexanone and optional cyclohexanol.
    Type: Grant
    Filed: November 26, 2001
    Date of Patent: October 1, 2002
    Assignees: Sumitomo Chemical Company, Limited, Daicel Chemical Industries, Ltd.
    Inventors: Shuzo Murata, Nobuhiro Tani
  • Patent number: 6437197
    Abstract: A process for increasing catalyst stability during the direct hydroxylation of liquid phase benzene or benzene derivatives with an oxidant and a solid catalyst under conditions effective to prevent coke formation on the catalyst. The process can be used to form phenol or phenol derivatives.
    Type: Grant
    Filed: April 27, 2000
    Date of Patent: August 20, 2002
    Assignee: Shell Oil Company
    Inventor: David Morris Hamilton, Jr.
  • Patent number: 6410805
    Abstract: A method and composition are disclosed for the hydroxylation of aromatic substrates in the presence of oxygen, hydrogen, and a catalyst. In a preferred embodiment, benzene is oxidized to phenol in the presence of oxygen, a vanadium catalyst, and hydrogen. The method is economical, safe, and amenable to commercial scale-up.
    Type: Grant
    Filed: January 16, 2001
    Date of Patent: June 25, 2002
    Assignee: General Electric Company
    Inventor: Terence Michael Barnhart
  • Patent number: 6399838
    Abstract: A process for preparing 2,6-dimethylphenol from 2,4,6-trimethylphenol is provided. The process includes two steps: (1) selective oxidation of 2,4,6-trimethylphenol to 3,5-dimethyl-4-hydroxybenzaldehyde and (2) deformylation of the resulting benzaldehyde to 2,6-dimethylphenol. In step (1), the 2,4,6-trimethylphenol is reacted with oxygen-containing gases at temperatures of 20 to 200° C. in the presence of an iron-containing catalyst, which has higher 3,5-dimethyl-4-hydroxybenzaldehyde selectivity than the known copper-based catalysts. In step (2), a copper-containing catalyst is used to replace the customarily used precious metal catalysts for the effective deformylation of the 3,5-dimethyl-4-hydroxybenzaldehyde to 2,6-dimethylphenol.
    Type: Grant
    Filed: February 2, 2001
    Date of Patent: June 4, 2002
    Assignee: National Science Council
    Inventors: Kuo-Tseng Li, Pang Yih Liu
  • Patent number: 6355847
    Abstract: Benzene, ascorbic acid acting as a reducing agent, and a vanadium-supported alumina catalyst are placed in an aqueous solution of acetic acid used as a solvent, and the reaction is carried out under an oxygen gas atmosphere having a pressure of at least 0.3 MPa so as to directly oxidize benzene and, thus, to obtain phenol at a high yield of at least 8%.
    Type: Grant
    Filed: July 29, 1999
    Date of Patent: March 12, 2002
    Assignee: President of Kobe University
    Inventor: Shigeru Tsuruya
  • Publication number: 20020016515
    Abstract: Benzene, ascorbic acid acting as a reducing agent, and a vanadium-supported alumina catalyst are placed in an aqueous solution of acetic acid used as a solvent, and the reaction is carried out under an oxygen gas atmosphere having a pressure of at least 0.3 MPa so as to directly oxidize benzene and, thus, to obtain phenol at a high yield of at least 8%.
    Type: Application
    Filed: September 25, 2001
    Publication date: February 7, 2002
    Applicant: PRESIDENT OF KOBE UNIVERSITY
    Inventor: Shigeru Tsuruya
  • Patent number: 6323378
    Abstract: A method and composition are disclosed for the oxidation of aromatic substrates in the presence of oxygen, a catalyst, a proton source, and a non-gaseous reductant. In a preferred embodiment, benzene is oxidized to phenol in the presence of oxygen, a vanadyl catalyst, trifluoroacetic acid as a proton source, and ferrocene as a reductant. The method is economical, safe, and amenable to commercial scale-up.
    Type: Grant
    Filed: January 16, 2001
    Date of Patent: November 27, 2001
    Assignee: General Electric Company
    Inventor: Terence Michael Barnhart
  • Patent number: 6265622
    Abstract: A method and composition are disclosed for the hydroxylation of aromatic substrates in the presence of oxygen, hydrogen, and a catalyst. In a preferred embodiment, benzene is oxidized to phenol in the presence of oxygen, a vanadium catalyst, and hydrogen. The method is economical, safe, and amenable to commercial scale-up.
    Type: Grant
    Filed: February 26, 1999
    Date of Patent: July 24, 2001
    Assignee: General Electric Company
    Inventor: Terence Michael Barnhart
  • Publication number: 20010003139
    Abstract: A method and composition are disclosed for the oxidation of aromatic substrates in the presence of oxygen, a catalyst, a proton source, and a non-gaseous reductant. In a preferred embodiment, benzene is oxidized to phenol in the presence of oxygen, a vanadyl catalyst, trifluoroacetic acid as a proton source, and ferrocene as a reductant. The method is economical, safe, and amenable to commercial scale-up.
    Type: Application
    Filed: January 16, 2001
    Publication date: June 7, 2001
    Inventor: Terence Michael Barnhart
  • Patent number: 6232510
    Abstract: A method and composition are disclosed for the oxidation of aromatic substrates in the presence of oxygen, a catalyst, a proton source, and a non-gaseous reductant. In a preferred embodiment, benzene is oxidized to phenol in the presence of oxygen, a vanadyl catalyst, trifluoroacetic acid as a proton source, and ferrocene as a reductant. The method is economical, safe, and amenable to commercial scale-up.
    Type: Grant
    Filed: February 26, 1999
    Date of Patent: May 15, 2001
    Assignee: General Electric Company
    Inventor: Terence Michael Barnhart
  • Patent number: 6191318
    Abstract: The present invention relates to a process for preparing hydroxylated aromatics by using hydrogen and oxygen and more particularly, to a process for preparing hydroxylated aromatics by using hydrogen and oxygen with a two-component heterogeneous catalyst. One component consists of porous catalyst containing one of Group VIII B transition metals such as Pd, Pt, Au and Cu, and hydrogen transfer organic compounds such as anthraquinone. The other component consists of a catalyst containing a transition metal selected from Ti, V, and Sn with tetrahedral coordination geometry. The main advantages of this new catalytic system are to 1) overcome the drawbacks of liquid phase oxidation using conventional homogeneous catalysts, 2) avoid use of expensive hydrogen peroxide as an oxidant, and 3) improve the selectivity of the reaction.
    Type: Grant
    Filed: June 14, 1999
    Date of Patent: February 20, 2001
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Sang Eon Park, Chul Wee Lee, Jong San Chang, Yong Ki Park
  • Patent number: 6187964
    Abstract: A method of producing a phenol compound comprising a step of oxidizing an aromatic aldehyde to an aryl formate and an aromatic carboxylic acid with an oxygen-containing gas, and a step of decomposing the aryl formate to the phenol compound. To facilitate the separation of the aryl formate and the unreacted aromatic aldehyde, a mixture of the aryl formate and the unreacted aromatic aldehyde is recycled to the oxidation process to concentrate the aryl formate in the oxidation mixture. Alternatively, the oxidation process is carried out in an organic solvent having substantially no ability of dissolving water to increase the conversion of the aromatic aldehyde and the selectivity of the aryl formate, thereby producing the aryl formate in a high yield.
    Type: Grant
    Filed: July 14, 1999
    Date of Patent: February 13, 2001
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Kazuo Tanaka, Yukio Sakai, Yasuhiro Shoji, Takafumi Yoshimura, Masatoshi Yoshimura
  • Patent number: 5962752
    Abstract: A process is disclosed for the catalytic hydroxylation of aromatic hydrocarbons which comprises contacting aromatic feedstock with oxidant comprising molecular oxygen, under suitable reaction conditions, in the presence of a catalyst comprising vanadyl (V.sup.IV) on an alumina support, preferably on leached alumina. The process is particularly suited, for example, to the one-step conversion of benzene to phenol.
    Type: Grant
    Filed: July 31, 1997
    Date of Patent: October 5, 1999
    Assignee: Sun Company, Inc.
    Inventors: Vincent A. Durante, Tilak P. Wijesekera, Swati Karmakar
  • Patent number: 5952532
    Abstract: A process is disclosed for the catalytic hydroxylation of aromatic hydrocarbons which comprises contacting aromatic feedstock with oxidant comprising molecular oxygen, under suitable reaction conditions, in the presence of a catalyst comprising three essential components: a support; transition metal selected from the group consisting of vanadium, niobium, copper, palladium, nickel and silver, or combinations thereof, and a promoter comprising a multidentate chelating, binucleating ligand. The catalysts may further comprise additional metal ions. The process is particularly suited, for example, to the one-step conversion of benzene to phenol.
    Type: Grant
    Filed: July 31, 1997
    Date of Patent: September 14, 1999
    Assignee: Sunoco, Inc.
    Inventors: Vincent A. Durante, Tilak P. Wijesekera, Swati Karmakar
  • Patent number: 5912391
    Abstract: Aromatic compounds such as benzene, toluene and xylene are hydroxylated by reaction with oxygen and hydroquinone or a substituted hydroquinone in the presence of a vanadium compound, typically a pentavalent vanadium oxy chelate with picolinic acid or a substituted picolinic acid. The vanadium compound may be produced in situ by reaction of the chelating agent with a tetravalent or pentavalent precursor vanadium compound.
    Type: Grant
    Filed: November 17, 1997
    Date of Patent: June 15, 1999
    Assignee: General Electric Company
    Inventors: Terence Michael Barnhart, Annah Waswa Hughes
  • Patent number: 5504260
    Abstract: Organic compounds are selectively oxidized by means of a particularly advantageous process, using elemental oxygen and a catalyst containing palladium and copper and carrying out the process in the presence of carbon monoxide.
    Type: Grant
    Filed: September 9, 1994
    Date of Patent: April 2, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Zoltan Kricsfalussy, Helmut Waldmann, Hans-Joachim Traenckner
  • Patent number: 5430181
    Abstract: Process for improving a controlled oxidation reaction between at least one reactant and oxygen, in which at least one reactant is reacted with oxygen or an oxygen containing gas, constituting a reaction mixture, in the presence of at least one additional gas which is introduced into said reaction mixture and is selected from methane, ethane and helium, and the resulting reaction product from the oxidation reaction is possibly treated so as to give a final product.
    Type: Grant
    Filed: February 19, 1993
    Date of Patent: July 4, 1995
    Assignee: L'Air Liquide Societe Anonyme Pour L'Etude et L'Exploitation des Procedes Georges Claude
    Inventors: Philippe Arpentinier, Jacques Koenig, Yves Torre
  • Patent number: 5426245
    Abstract: A phenol is produced by reacting an aromatic compound with oxygen and hydrogen in the liquid phase in the presence of a catalyst comprising a noble metal of group VIII of the periodic table, which is supported on a carrier, and in the co-presence of a vanadium compound. The reaction is carried out either (i) by using as the catalyst a catalyst containing 0% to 0.15% by weight, based on the weight of the catalyst, of halogens, or (ii) further in the co-presence of a diketone compound of the following formula (1) or (2): ##STR1## wherein R.sup.1 and R.sup.
    Type: Grant
    Filed: August 5, 1994
    Date of Patent: June 20, 1995
    Assignee: Tosoh Corporation
    Inventors: Michiyuki Hamada, Hideyuki Niwa, Motohiro Oguri, Takanori Miyake
  • Patent number: 5210331
    Abstract: The invention relates to a process for the preparation of a phenol by oxidative decarboxylation of a corresponding arylcarboxylic acid in the presence of a Cu-containing catalyst, the phenol being obtained through a hydrolysis step. The characteristic part of the process is oxidation of a Cu(I)-containing catalyst and reduction and hydrolysis in the absence of oxygen. The process can be carried out under liquid phase or gas phase conditions in a one-step or multi-step process and nucleation agents can be added for crystallization during catalyst oxidation. In a preferred embodiment, at least 0.04 wt.% copper remains present as Cu(I) after oxidation.
    Type: Grant
    Filed: December 31, 1991
    Date of Patent: May 11, 1993
    Assignee: DSM NV
    Inventors: Wim Buijs, Leon H. B. Frijns, Matthias R. J. Offermanns
  • Patent number: 5099076
    Abstract: The present invention is directed to a method for the preparation of p,p'-biphenol by simplified processes achieved by batch or continuous operations which comprises using phenol and isobutylene as starting materials, allowing phenol to react with isobutylene in the presence of aluminum phenoxide, oxidizing the resulting reaction liquid in the presence of an alkaline catalyst, and debutylating the reaction liquid in the presence of a debutylation catalyst.
    Type: Grant
    Filed: October 5, 1990
    Date of Patent: March 24, 1992
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Katsunori Takahashi, Mikio Kawahara, Shunji Yago, Yoshiharu Ayabe
  • Patent number: 5095143
    Abstract: A method to oxidize an oxidizable component in a liquid phase with an oxygen-containing gas is disclosed. The method comprises mixing the liquid phase and gas phase in a reactor with a rotating agitator element operated at constant power.
    Type: Grant
    Filed: June 13, 1990
    Date of Patent: March 10, 1992
    Assignee: Amoco Corporation
    Inventors: Daniel L. Heberer, Paul R. Schiller, Virginia R. Seemann, Michael J. Yerkes
  • Patent number: 4992600
    Abstract: The instant invention relates to a process for the oxidation of benzene to phenol which comprises contacting benzene and molecular oxygen with a dihydrodihydroxyanthracene-sulfonate salt dissolved in water, optionally in the presence of an oxidation catalyst, and subsequently separating from the reaction product phenol and the corresponding anthraquinone-sulfonate. The by-product anthraquinone is suitably recycled to the benzene oxidation step by hydrogenating the anthraquinone salt to the dihydrodihydroxyanthracene salt.
    Type: Grant
    Filed: September 26, 1989
    Date of Patent: February 12, 1991
    Assignee: Shell Oil Company
    Inventors: Kuo-Hua Chao, Raymond T. Moy
  • Patent number: 4982015
    Abstract: The instant invention relates to a process for the oxidation of benzene to phenol which comprises contacting benzene and molecular oxygen with a dihydrodihydroxynaphthoquinone, optionally in the presence of an oxidation catalyst, and subsequently separating from the reaction product phenol and the corresponding naphthoquinone. The by-product napththoquinone is suitably recycled to the benzene oxidation step by hydrogenating the naphthoquinone to the dihydrodihydroxynapththoquinone.
    Type: Grant
    Filed: September 26, 1989
    Date of Patent: January 1, 1991
    Assignee: Shell Oil Company
    Inventors: Kuo-Hua Chao, Raymond T. Moy
  • Patent number: 4950794
    Abstract: The oxidation of ethylbenzene to products comprised of ethylbenzene hydroperoxide and acetophenone is modified in order to enhance acetophenone production by reducing the alkali content of the oxidation mixture below 0.1 ppm and by incorporation of 0.05 to 2 wt. % water in the oxidation mixture.
    Type: Grant
    Filed: May 24, 1989
    Date of Patent: August 21, 1990
    Assignee: Arco Chemical Technology, Inc.
    Inventors: Lawrence M. Candela, Robert N. Cochran, Scott H. Sandler
  • Patent number: 4929771
    Abstract: Process for the preparation of alkyl-substituted phenols or naphthols by oxidizing the corresponding dialkylbenzenes or dialkylnaphthalenes, respectively, at elevated temperatures of, for example, 70.degree. to 130.degree. C. by means of oxygen or oxygen donors, in the absence of solvents and in the presence of an alkali metal salt or alkaline earth metal salt of an organic carboxylic acid having 5 to 14 carbon atoms, to give the corresponding 2,6-dialkylnaphthalene-or 1,4-dialkylphenyl monohydroperoxides and subsequently hydrolysing the latter in a customary manner.The process results in pure, easily isolatable products in a good yield. The products of the process according to the invention are valuable precursors and intermediates for, inter alia, dyes, plastics or pharmaceuticals.
    Type: Grant
    Filed: December 1, 1988
    Date of Patent: May 29, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Martin Clausen, Paul Rys, Wang Junkuan
  • Patent number: 4691053
    Abstract: A novel process for producing oxygen-containing organic compounds with high selectivity and good yield by oxidizing organic compounds under mild conditions is provided, which process comprises using as a catalyst for the oxidation, a complex (M.sub.m X.sub.n.L.sub.l) consisting of a transition metal compound (M.sub.m X.sub.n) and an organic phosphorous compound (L) as a ligand, wherein M represents a transition metal belonging to group I, group IV.about.VII or iron group in group VIII of the periodic table; X represents an anion such as a halogen; ligand L represents an organic phosphorous compound; and m and n mean a number of the atomic valence of said transition metal (ion) M and said anion X, respectively, and l means a number of said ligand.
    Type: Grant
    Filed: June 4, 1984
    Date of Patent: September 1, 1987
    Assignee: Babcock-Hitachi Kabushiki Kaisha
    Inventors: Mutsuo Yamada, Yasuyuki Nishimura, Yoshijiro Arikawa, Takanori Kuwahara, Taiji Kamiguchi, Hirotoshi Tanimoto
  • Patent number: 4620043
    Abstract: Multicomponent catalysts comprising copper, a metal selected from the group consisting of vanadium, chromium, manganese, iron, cobalt, nickel and zinc; and phosphate are employed for oxidizing an aromatic carboxylic acid to the corresponding phenol, e.g., benzoic acid to phenol.
    Type: Grant
    Filed: October 17, 1985
    Date of Patent: October 28, 1986
    Assignee: The Dow Chemical Company
    Inventors: Chiu T. Lam, David M. Shannon
  • Patent number: 4584417
    Abstract: p-Alkylphenols such as p-cresol are prepared by the reaction of p-hydroxyalkylphenols with water and oxygen in the presence of at least one oxide of a Group II metal having an atomic weight less than 70, preferably zinc oxide. At least part of the p-hydroxyalkylphenol contains a p-hydroxymethyl group, and it is preferably entirely p-hydroxybenzyl alcohol. The reaction temperature is about 350.degree.-550.degree. C.
    Type: Grant
    Filed: February 6, 1984
    Date of Patent: April 22, 1986
    Assignee: General Electric Company
    Inventor: John J. Talley
  • Patent number: 4532360
    Abstract: The yield and the selectivity of an oxidation reaction of alkyl substituted benzenes to ketones and phenols in the presence of hydrogen bromide is increased through the use of cerium oxide, triphenylborate, boron phosphate and water.
    Type: Grant
    Filed: January 12, 1984
    Date of Patent: July 30, 1985
    Assignee: Phillips Petroleum Company
    Inventor: Charles A. Drake