Molecular Oxygen Utilized Patents (Class 568/802)
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Patent number: 11075318Abstract: 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: GrantFiled: May 22, 2014Date of Patent: July 27, 2021Assignee: TOSHIBA MITSUBISHI-ELECTRIC INDUSTRIAL SYSTEMS CORPORATIONInventors: Takahiro Shirahata, Hiroyuki Orita, Takahiro Hiramatsu, Hiroshi Kobayashi
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Patent number: 8772552Abstract: 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: GrantFiled: September 20, 2012Date of Patent: July 8, 2014Assignee: Council of Scientific & Industrial ResearchInventors: Rajaram Bal, Shubhra Acharyya Shankha, Shilpi Ghosh, Bipul Sarkar, Karan Singh Rawat, Chandrashekar Pendem
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Patent number: 8729315Abstract: 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: GrantFiled: October 29, 2010Date of Patent: May 20, 2014Assignee: Versalis S.p.A.Inventors: Mauro Burattini, Roberto Bagatin
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Publication number: 20130096351Abstract: 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: ApplicationFiled: September 20, 2012Publication date: April 18, 2013Applicant: Council of Scientific & Industrial ResearchInventor: Council of Scientific & Industrial Research
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Publication number: 20120252999Abstract: 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: ApplicationFiled: April 12, 2012Publication date: October 4, 2012Inventor: Bruce H. Peters
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Patent number: 8247622Abstract: 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: GrantFiled: October 20, 2010Date of Patent: August 21, 2012Assignee: Polimeri Europa S.p.A.Inventors: Leonardo Dalloro, Alberto Cesana, Roberto Buzzoni, Fausto Genoni, Guido Spano, Franco Rivetti
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Patent number: 8017822Abstract: 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: GrantFiled: October 5, 2009Date of Patent: September 13, 2011Assignee: Shell Oil CompanyInventors: Howard Lam Ho Fong, Richard Dale Swain
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Publication number: 20110092746Abstract: 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: ApplicationFiled: October 20, 2010Publication date: April 21, 2011Applicant: POLIMERI EUROPA S.p.A.Inventors: Leonardo DALLORO, Alberto Cesana, Roberto Buzzoni, Fausto Genoni, Guido Spano, Franco Rivetti
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Publication number: 20100234637Abstract: 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: ApplicationFiled: March 15, 2010Publication date: September 16, 2010Inventors: Howard Lam Ho FONG, Richard Dale Swain
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Publication number: 20100087686Abstract: 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: ApplicationFiled: October 5, 2009Publication date: April 8, 2010Inventors: Howard Lam Ho FONG, Richard Dale SWAIN
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Publication number: 20090234121Abstract: 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: ApplicationFiled: January 15, 2009Publication date: September 17, 2009Inventors: Roy A. Periana, William A. Goddard, III, Jonas Oxgaard, Kenneth Young
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Patent number: 7091386Abstract: 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: GrantFiled: May 3, 2004Date of Patent: August 15, 2006Assignee: U.S. Department of EnergyInventors: Robert J. Beuhler, Michael G. White, Jan Hrbek
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Patent number: 6936740Abstract: 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: GrantFiled: August 19, 2004Date of Patent: August 30, 2005Assignee: ARCO Chemical Technology, L.P.Inventors: Robert N. Cochran, Jay F. Miller, Eric John Beckman, Sarah Emma Jones
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Patent number: 6911563Abstract: 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: GrantFiled: December 27, 2001Date of Patent: June 28, 2005Assignees: National Institute of Advanced Industrial Science, NOK CorporationInventors: Fujio Mizukami, Shuichi Niwa, Makoto Toba, Naotsugu Itoh, Tomonari Saito, Takemi Nanba, Hiroshi Shoji, Kazuhiko Haba
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Patent number: 6900358Abstract: 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: GrantFiled: April 24, 2001Date of Patent: May 31, 2005Assignee: Shell Oil CompanyInventor: David Morris Hamilton, Jr.
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Patent number: 6768013Abstract: 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: GrantFiled: June 15, 2001Date of Patent: July 27, 2004Assignee: UOP LLCInventor: Peter R. Pujado
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Patent number: 6646167Abstract: 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: GrantFiled: September 25, 2001Date of Patent: November 11, 2003Assignee: President of Kobe UniversityInventor: Shigeru Tsuruya
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Publication number: 20030171625Abstract: 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: ApplicationFiled: March 6, 2003Publication date: September 11, 2003Inventors: Yasutaka Ishii, Tatsuya Nakano
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Publication number: 20030050515Abstract: 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: ApplicationFiled: August 26, 2002Publication date: March 13, 2003Inventor: Gregory Kaplan
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Patent number: 6482989Abstract: A method for oxidizing an alkane, comprising the step of oxidizing said alkane with oxygen in the presence of an aldehyde, a copper-based catalyst and a nitrogen-containing compound. This method may be used to convert alkanes to corresponding alcohols and ketone having pharmaceutical activities, etc.Type: GrantFiled: July 18, 2001Date of Patent: November 19, 2002Assignee: Osaka UniversityInventors: Shun-ichi Murahashi, Naruyoshi Komiya, Yukiko Hayashi
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Patent number: 6479705Abstract: 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: GrantFiled: December 14, 2000Date of Patent: November 12, 2002Assignees: Sumitomo Chemical Company, Limited, Daicel Chemical Industries, Ltd.Inventors: Shuzo Murata, Nobuhiro Tani, Hiroyuki Asano
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Patent number: 6459002Abstract: 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: GrantFiled: November 26, 2001Date of Patent: October 1, 2002Assignees: Sumitomo Chemical Company, Limited, Daicel Chemical Industries, Ltd.Inventors: Shuzo Murata, Nobuhiro Tani
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Patent number: 6437197Abstract: 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: GrantFiled: April 27, 2000Date of Patent: August 20, 2002Assignee: Shell Oil CompanyInventor: David Morris Hamilton, Jr.
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Patent number: 6410805Abstract: 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: GrantFiled: January 16, 2001Date of Patent: June 25, 2002Assignee: General Electric CompanyInventor: Terence Michael Barnhart
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Patent number: 6399838Abstract: 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: GrantFiled: February 2, 2001Date of Patent: June 4, 2002Assignee: National Science CouncilInventors: Kuo-Tseng Li, Pang Yih Liu
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Patent number: 6355847Abstract: 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: GrantFiled: July 29, 1999Date of Patent: March 12, 2002Assignee: President of Kobe UniversityInventor: Shigeru Tsuruya
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Publication number: 20020016515Abstract: 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: ApplicationFiled: September 25, 2001Publication date: February 7, 2002Applicant: PRESIDENT OF KOBE UNIVERSITYInventor: Shigeru Tsuruya
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Patent number: 6323378Abstract: 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: GrantFiled: January 16, 2001Date of Patent: November 27, 2001Assignee: General Electric CompanyInventor: Terence Michael Barnhart
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Patent number: 6265622Abstract: 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: GrantFiled: February 26, 1999Date of Patent: July 24, 2001Assignee: General Electric CompanyInventor: Terence Michael Barnhart
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Publication number: 20010003139Abstract: 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: ApplicationFiled: January 16, 2001Publication date: June 7, 2001Inventor: Terence Michael Barnhart
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Patent number: 6232510Abstract: 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: GrantFiled: February 26, 1999Date of Patent: May 15, 2001Assignee: General Electric CompanyInventor: Terence Michael Barnhart
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Patent number: 6191318Abstract: 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: GrantFiled: June 14, 1999Date of Patent: February 20, 2001Assignee: Korea Research Institute of Chemical TechnologyInventors: Sang Eon Park, Chul Wee Lee, Jong San Chang, Yong Ki Park
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Patent number: 6187964Abstract: 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: GrantFiled: July 14, 1999Date of Patent: February 13, 2001Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Kazuo Tanaka, Yukio Sakai, Yasuhiro Shoji, Takafumi Yoshimura, Masatoshi Yoshimura
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Patent number: 5962752Abstract: 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: GrantFiled: July 31, 1997Date of Patent: October 5, 1999Assignee: Sun Company, Inc.Inventors: Vincent A. Durante, Tilak P. Wijesekera, Swati Karmakar
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Patent number: 5952532Abstract: 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: GrantFiled: July 31, 1997Date of Patent: September 14, 1999Assignee: Sunoco, Inc.Inventors: Vincent A. Durante, Tilak P. Wijesekera, Swati Karmakar
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Patent number: 5912391Abstract: 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: GrantFiled: November 17, 1997Date of Patent: June 15, 1999Assignee: General Electric CompanyInventors: Terence Michael Barnhart, Annah Waswa Hughes
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Patent number: 5504260Abstract: 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: GrantFiled: September 9, 1994Date of Patent: April 2, 1996Assignee: Bayer AktiengesellschaftInventors: Zoltan Kricsfalussy, Helmut Waldmann, Hans-Joachim Traenckner
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Patent number: 5430181Abstract: 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: GrantFiled: February 19, 1993Date of Patent: July 4, 1995Assignee: L'Air Liquide Societe Anonyme Pour L'Etude et L'Exploitation des Procedes Georges ClaudeInventors: Philippe Arpentinier, Jacques Koenig, Yves Torre
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Patent number: 5426245Abstract: 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: GrantFiled: August 5, 1994Date of Patent: June 20, 1995Assignee: Tosoh CorporationInventors: Michiyuki Hamada, Hideyuki Niwa, Motohiro Oguri, Takanori Miyake
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Patent number: 5210331Abstract: 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: GrantFiled: December 31, 1991Date of Patent: May 11, 1993Assignee: DSM NVInventors: Wim Buijs, Leon H. B. Frijns, Matthias R. J. Offermanns
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Patent number: 5099076Abstract: 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: GrantFiled: October 5, 1990Date of Patent: March 24, 1992Assignee: Honshu Chemical Industry Co., Ltd.Inventors: Katsunori Takahashi, Mikio Kawahara, Shunji Yago, Yoshiharu Ayabe
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Patent number: 5095143Abstract: 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: GrantFiled: June 13, 1990Date of Patent: March 10, 1992Assignee: Amoco CorporationInventors: Daniel L. Heberer, Paul R. Schiller, Virginia R. Seemann, Michael J. Yerkes
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Patent number: 4992600Abstract: 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: GrantFiled: September 26, 1989Date of Patent: February 12, 1991Assignee: Shell Oil CompanyInventors: Kuo-Hua Chao, Raymond T. Moy
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Patent number: 4982015Abstract: 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: GrantFiled: September 26, 1989Date of Patent: January 1, 1991Assignee: Shell Oil CompanyInventors: Kuo-Hua Chao, Raymond T. Moy
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Patent number: 4950794Abstract: 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: GrantFiled: May 24, 1989Date of Patent: August 21, 1990Assignee: Arco Chemical Technology, Inc.Inventors: Lawrence M. Candela, Robert N. Cochran, Scott H. Sandler
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Patent number: 4929771Abstract: 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: GrantFiled: December 1, 1988Date of Patent: May 29, 1990Assignee: Ciba-Geigy CorporationInventors: Martin Clausen, Paul Rys, Wang Junkuan
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Patent number: 4691053Abstract: 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: GrantFiled: June 4, 1984Date of Patent: September 1, 1987Assignee: Babcock-Hitachi Kabushiki KaishaInventors: Mutsuo Yamada, Yasuyuki Nishimura, Yoshijiro Arikawa, Takanori Kuwahara, Taiji Kamiguchi, Hirotoshi Tanimoto
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Patent number: 4620043Abstract: 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: GrantFiled: October 17, 1985Date of Patent: October 28, 1986Assignee: The Dow Chemical CompanyInventors: Chiu T. Lam, David M. Shannon
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Patent number: 4584417Abstract: 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: GrantFiled: February 6, 1984Date of Patent: April 22, 1986Assignee: General Electric CompanyInventor: John J. Talley
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Patent number: 4532360Abstract: 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: GrantFiled: January 12, 1984Date of Patent: July 30, 1985Assignee: Phillips Petroleum CompanyInventor: Charles A. Drake