Preparing From A Peroxide Or Preparing By Oxidation Patents (Class 568/815)
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Patent number: 8957255Abstract: The disclosure relates to a method of oxidation of an aliphatic C—H bond in an organic compound using CdO2 or ZnO2 nanoparticles as oxidizing agents. The instant disclosure relates to a method of oxidizing toluene using metal peroxide nanoparticles such as CdO2, ZnO2 as oxidizing agents to obtain oxidized products predominantly comprising benzaldehyde.Type: GrantFiled: October 4, 2013Date of Patent: February 17, 2015Assignee: Jawaharlal Nehru Centre for Advanced Scientific ResearchInventors: Chintamani Nagesa Ramachandra Rao, Ujjal Kam Gautam, Srinivasa Rao Lingampalli
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Publication number: 20140171689Abstract: The disclosure relates to a method of oxidation of an aliphatic C—H bond in an organic compound using CdO2 or ZnO2 nanoparticles as oxidizing agents. The instant disclosure relates to a method of oxidizing toluene using metal peroxide nanoparticles such as CdO2, ZnO2 as oxidizing agents to obtain oxidized products predominantly comprising benzaldehyde.Type: ApplicationFiled: October 4, 2013Publication date: June 19, 2014Applicant: Jawaharlal Nehru Centre for Advanced Scientific ResearchInventors: Chintamani Nagesa Ramachandra Rao, Ujjal Kam Gautam, Srinivasa Rao Lingampalli
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Publication number: 20130172610Abstract: A process for oxidizing an alkyl-aromatic compound is described. The process includes oxidizing the alkyl-aromatic compound to produce a first oxidation product; contacting at least a portion of the first oxidation product, a solvent comprising an ionic liquid, a bromine source, a catalyst, and an oxidizing agent to produce a second product comprising a mother liquor and at least one of an aromatic alcohol, an aromatic aldehyde, an aromatic ketone, and an aromatic carboxylic acid; and adding at least a portion of the mother liquor in the contacting step.Type: ApplicationFiled: December 29, 2011Publication date: July 4, 2013Applicant: UOP LLCInventors: Alakananda Bhattacharyya, Raymond C. Shih
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Publication number: 20130041175Abstract: A process for oxidizing an alkyl-aromatic compound is described. The process includes contacting the alkyl-aromatic compound, a solvent comprising an ionic liquid, a bromine source, a catalyst, and an oxidizing agent in a first reaction zone to produce a first product comprising a first mother liquor and at least one of an aromatic alcohol, an aromatic aldehyde, an aromatic ketone, and an aromatic carboxylic acid.Type: ApplicationFiled: October 12, 2012Publication date: February 14, 2013Applicant: UOP LLCInventors: Alakananda Bhattacharyya, Raymond Shih
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Patent number: 8106242Abstract: Multi-step process for the preparation of compounds via hazardous intermediates comprising the steps of a) preparing in a microreactor a hazardous intermediate and b) optionally performing one or more reaction steps on the hazardous intermediate in one or more additional microreactors and c) further converting the hazardous intermediate with a suitable reaction agent in a subsequent microreactor until a stable end product is formed.Type: GrantFiled: May 23, 2007Date of Patent: January 31, 2012Assignee: DSM IP Assets B.V.Inventors: Rafael Wilhelmus Elisabeth Ghislain Reintjens, Quirinus Bernardus Broxterman, Martina Kotthaus, Peter Poechlauer
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Patent number: 7888537Abstract: The present invention provides a process for decomposing a cumene hydroperoxide to produce phenol and acetone. The process utilizes a solid catalyst that can be non-layered or layered. The process includes: (1) introducing a process stream containing cumene hydroperoxide into a reaction vessel; (2) contacting the process stream with catalyst particles to form a process stream; and (3) withdrawing a portion of the product stream from the reactor and recovering phenol and acetone products.Type: GrantFiled: December 19, 2007Date of Patent: February 15, 2011Assignee: UOP LLCInventors: Robert J. Schmidt, Deng-Yang Jan, Raelynn M. Miller, James A. Johnson
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Patent number: 7868201Abstract: A process for the oxidation of hydrocarbons comprises contacting the hydrocarbon with an oxygen-containing gas in the presence of a catalyst comprising a microporous solid support, preferably a zeolite, having from 8- to 12-ring open windows and comprising non-framework metal cations selected from manganese, iron, cobalt, vanadium, chromium, copper, nickel, and ruthenium, and mixtures thereof, providing that the oxygen-containing gas does not contain significant amounts of added hydrogen. The catalyst is novel and forms part of the invention. The process may be used for oxidation of alkanes, cycloalkanes, benzene and alkylbenzenes, and is suitable for use in regioselective terminal oxidation of straight chain alkanes and for selective oxidation/separation of p-dialkylbenzenes from an alkylbenzene mixture, for example, p-xylene from an isomeric mixture of xylenes.Type: GrantFiled: July 1, 2005Date of Patent: January 11, 2011Assignee: ExxonMobil Research and Engineering CompanyInventors: Bi-Zeng Zhan, Bjorn Moden, Jihad Dakka, Jose Santiesteban, Sebastian C. Reyes, Enrique Iglesia
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Publication number: 20090192337Abstract: The present invention provides a process for direct hydroxylation of aromatic hydrocarbons like benzene to phenol, toluene to cresols and anisole to methoxy phenols by using hydrogen peroxide as environmentally benign oxidant in polar solvent like acetonitrile using vanadium phthalocyanine or its derivative as a catalyst, at a temperature in the range of 25-100° C.Type: ApplicationFiled: October 30, 2008Publication date: July 30, 2009Applicant: COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCHInventors: Suman Lata JAIN, Jomy K. JOSEPH, Sweety SINGHAL, Bir SAIN, Ragunathan SIVAKUMARAN, Basant KUMAR
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Patent number: 7166754Abstract: This invention provides methods and catalyst systems for catalyzing enantioselective oxidation reactions, including cyclization reactions and enantioselective oxidation reactions of secondary alcohols and other similarly reactive organic substrates. Use of the methods and catalyst systems for kinetic resolution of racemic mixtures of secondary alcohols is also described.Type: GrantFiled: March 4, 2002Date of Patent: January 23, 2007Assignee: California Institute of TechnologyInventors: Eric M. Ferreira, Brian M. Stoltz
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Patent number: 7148386Abstract: A process for the preparation of hydroquinone compounds comprising, reacting an aromatic hydroxy compound with an oxidizing agent in a biphasic solvent system. The reaction is carried out in the presence of a transition metal hydroxy phosphate catalyst to produce the corresponding hydroquinone compound.Type: GrantFiled: July 30, 2004Date of Patent: December 12, 2006Assignee: General Electric CompanyInventors: Jegadeesh Thampi, Sunil Ashtekar, Pramod Kumbhar, Rathinam Jothi Mahalingam
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Patent number: 7094925Abstract: A process for the oxidation of an alkyl-aromatic compound, wherein the aromatic compound is admixed with an oxidising agent or sulfur compound in the presence of an ionic liquid is described. In this process, air, dioxygen, peroxide, superoxide, any other form of active oxygen, nitrite, nitrate, nitric acid or other oxides (or oxyhalides) of nitrogen (hydrate or anhydrous) are preferably used as the oxidising agent. The process is usually under Bronsted acidic conditions. The product of the oxidation reaction is preferably a carboxylic acid or ketone or an intermediate compound in the oxidation such as an aldehyde, or alcohol. The oxidation is preferably performed in an ionic liquid containing an acid promoter such as methanesulfonic acid.Type: GrantFiled: October 5, 2001Date of Patent: August 22, 2006Assignee: The Queen's University of BelfastInventors: Martyn John Earle, Suhas Prabhakar Katdare
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Patent number: 7038068Abstract: A liquid/liquid extraction method is used for separating a perfluorinated polyether (PFPE) into two molecular-weight distributions using an alcohol or cyclic ether as one solvent and a fluorinated solvent as the other solvent. The more polar alcohol or cyclic ether solvent extracts the lower molecular weight PFPE and the less polar fluorinated solvent extracts the higher molecular weight PFPE. In addition, when the PFPE is a mixture of PFPEs with different end groups, such as a mixture of predominantly Z-Tetraol but with other PFPEs with Z-Dol end groups, there is an enrichment of the Z-Tetraol in the more polar solvent. The preferred PFPE is a mixture of PFPEs in as-purchased Z-Tetraol and the preferred solvents are methanol or trifluoroethanol as one solvent and a perfluorinated hydrocarbon, such as perfluorohexane, as the other solvent.Type: GrantFiled: March 16, 2004Date of Patent: May 2, 2006Assignee: Hitachi Global Storage Technologies Netherlands B.V.Inventor: John M. Burns
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Patent number: 6974888Abstract: Process for preparing alkylaryl hydroperoxide containing product, which process comprises: (a) oxidation of an alkylaryl compound to obtain reaction product containing alkylaryl hydroperoxide, (b) contacting with water at least part of the alkylaryl hydroperoxide containing reaction product obtained in step (a) which reaction product contains less than 0.05 % wt of sodium, (c) separating the product of step (b) into a hydrocarbonaceous phase containing alkylaryl hydroperoxide and an aqueous phase, (d) optionally repeating process steps (b) and (c) one or more times, (e) contacting at least part of the hydrocarbonaceous phase containing alkylaryl hydroperoxide obtained in step (c) or (d) with olefin and catalyst to obtain alkylaryl hydroxide and oxirane compound, and (f) separating at least part of the oxirane compound from the alkylaryl hydroxide.Type: GrantFiled: January 14, 2004Date of Patent: December 13, 2005Assignee: Shell Oil CompanyInventors: Antoon Paul Michael Kremers, Eduardus Petrus Simon Schouten, Cornelis Willem Adriaan Schram
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Patent number: 6849771Abstract: The invention relates to a process for converting 1-phenylethanol into styrene, which process involves: (1) contacting a feed containing 1-phenylethanol, organic acid and 2-phenylethanol with a catalyst to obtain a product containing styrene, and (2) removing ester compounds based on 2-phenylethanol and organic acid from the product of step (1), in which process the feed of step (1) has a molar ratio of organic acid to 2-phenylethanol of at least 1:10.Type: GrantFiled: August 6, 2003Date of Patent: February 1, 2005Assignee: Shell Oil CompanyInventors: Timothy Michael Nisbet, Eduardus Petrus Simon Schouten, Cornelis Willem Adriaan Schram
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Patent number: 6743952Abstract: The present invention provides an improved process for the production of benzaldehyde with 40-50% selectivity by the catalytic liquid phase air oxidation of toluene using a composite catalytic system comprising salts of iron, cobalt, manganese, molybdenum or nickel as recyclable catalyst, salts of manganese or copper as recyclable co-catalyst and cobalt bromide, sodium bromide, sodium chloride and zinc bromide as promoter.Type: GrantFiled: March 28, 2002Date of Patent: June 1, 2004Assignee: Council of Scientific and Industrial ResearchInventors: Mannepalli Lakshmi Kantham, Pentlavalli Sreekanth, Kottapalli Koteshwara Rao, Thella Prathap Kumar, Bhavnari Purna C. Rao, Boyapati Manoranjan Choudary
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Patent number: 6700005Abstract: Process for preparing alkylaryl hydroperoxide containing product, which process comprises: (a) oxidation of an alkylaryl compound to obtain reaction product containing alkylaryl hydroperoxide, (b) contacting with water at least part of the alkylaryl hydroperoxide containing reaction product obtained in step (a) which reaction product contains less than 0.05% wt of sodium, (c) separating the product of step (b) into a hydrocarbonaceous phase containing alkylaryl hydroperoxide and an aqueous phase, (d) optionally repeating process steps (b) and (c) one or more times, (e) contacting at least part of the hydrocarbonaceous phase containing alkylaryl hydroperoxide obtained in step (c) or (d) with olefin and catalyst to obtain alkylaryl hydroxide and oxirane compound, and (f) separating at least part of the oxirane compound from the alkylaryl hydroxide.Type: GrantFiled: February 6, 2003Date of Patent: March 2, 2004Assignee: Shell Oil CompanyInventors: Antoon Paul Michael Kremers, Eduardus Petrus Simon Schouten, Cornelis Willem Adriaan Schram
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Patent number: 6590129Abstract: 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: March 19, 2001Date of Patent: July 8, 2003Assignee: Toray Industries, Inc.Inventors: Shotaro Matsuoka, Masaaki Suematsu, Akira Kitamura
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Publication number: 20030055297Abstract: A process for the preparation of neuraminidase inhibitors having structural formula (28) 1Type: ApplicationFiled: April 3, 2002Publication date: March 20, 2003Inventors: Steven J. Wittenberger, Lakshmi Bhagavatula, David A. DeGoey, John DeMattei, Ashok K. Gupta, David R. Hill, Sukumar Manna, Maureen Ann McLaughlin, Paul J. Nichols, Premchandran H. Ramiya, Michael W. Rasmussen, Zhenping Tian
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Patent number: 6437176Abstract: 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: March 19, 2001Date of Patent: August 20, 2002Assignee: Toray Industries, Inc.Inventors: Shotaro Matsuoka, Masaaki Suematsu, Akira Kitamura
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Publication number: 20020045781Abstract: A process for the cleavage of alkylaryl hydroperoxides includes steps for producing a mixture of a concentrate that contains at least one alkylaryl hydroperoxide to be cleaved and a cleavage product obtained from the cleavage of an alkylaryl hydroperoxide, dividing this mixture into at least two parts and cleaving the alkylaryl hydroperoxides in parallel at different temperatures. One of the two parts is treated at a temperature sufficiently high for an integrated thermal post-treatment to be achieved. The process consumes less energy since less steam has to be used. Problems which can result from fouling in heat exchangers are largely prevented. No second feed point for alkylaryl hydroperoxide has to be provided. The process can be used in the preparation of phenol and acetone by the Hock method.Type: ApplicationFiled: October 18, 2001Publication date: April 18, 2002Applicant: PHENOLCHEMIE GMBH & CO. KGInventors: Uwe Tanger, Manfred Weber
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Publication number: 20010018543Abstract: 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: 1Type: ApplicationFiled: March 19, 2001Publication date: August 30, 2001Applicant: Toray Industries, Inc.Inventors: Shotaro Matsuoka, Masaaki Suematsu, Akira Kitamura
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Patent number: 6281382Abstract: The method of oxidizing the alkyl groups of alkylbenzenes using palladium phenanthroline acetate or a palladium acetate with modified phenanthroline ligand catalyst. The palladium acetate catalyst with modified phenanthroline has the following formula: wherein R1 is selected from the group consisting of alkyl groups of from 1 to 3 carbon atoms, OH, and NO2 groups and halogen and hydrogen atoms with at least six of the R1 groups being hydrogen atoms in the ligand.Type: GrantFiled: June 1, 2000Date of Patent: August 28, 2001Assignee: Georgia Tech Research Corp.Inventors: Mark G. White, Alexei V. Iretski
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Patent number: 6271425Abstract: A novel process for producing alcohols, characterized by reacting an organic halide represented by the formula R—X (wherein R means an organic residue and X means a halogen atom) with oxygen molecules in the presence of an organotin compound and a reducing agent and optionally in the presence of a free-radical inhibitor in an amount up to 0.3 equivalent based on the organic halide to obtain an alcohol represented by the general formula R—OH (wherein R has the same meaning as the above).Type: GrantFiled: September 7, 1999Date of Patent: August 7, 2001Assignees: Fujisawa Pharmaceutical Co., Ltd.Inventors: Eiichi Nakamura, Masaya Sawamura
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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: 6218581Abstract: The present invention relates to a process of producing optically active alcohol having high optical purity by performing an enzyme conversion reaction on a raw material serving as the substrate, examples of which include racemic alcohol, ketone and the acylated form of a racemic alcohol, followed by hydrolysis as necessary, using as an optical separation catalyst a immobilized water-soluble protein extracted from inexpensive and safe grains or beans in order to solve the problems of the reaction process consisting of low yield due to the occurrence of side reactions, detrimental effects on the ecosystem and their accompanying cost burden, the need for aseptic procedures and the extended amount of time of subculturing, all of which are problems associated with production processes of optically active alcohols of the prior art that use microorganisms, microorganism enzymes, animal tissue enzymes and cultured plant cells.Type: GrantFiled: August 6, 1999Date of Patent: April 17, 2001Assignee: Sanyo Shokuhin Co., Ltd.Inventor: Hiroyuki Nagaoka
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Patent number: 6002037Abstract: The present invention describes the Zr-catalyzed asymmetric carboalumination of alkenes to produce chiral alkylalanes that can be converted to various chiral organic compounds, such as isoalkyl alcohols, in highly enantiomeric excess. More particularly, the asymmetric addition of alkylaluminums to terminal alkenes under the influence of a catalyst such as a chiral zirconocene derivative produces chiral alkylaluminums that can be oxidized to 2-alkyl-substituted products (particularly alcohols) in greater than 60% enantiomeric excess. The ee figures can often exceed 95%. The organoalanes produces by the inventive process can be converted to a wide variety of other organic compounds of interest in the production of vitamins, pharmaceuticals and other medicinally and biologically important compounds, including vitamins and antibiotics.Type: GrantFiled: October 14, 1997Date of Patent: December 14, 1999Assignee: Purdue Research FoundationInventors: Ei-ichi Negishi, Denis Y. Kondakov
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Patent number: 5723677Abstract: The invention comprises a method for the oxidation of alkanes to alcohols and for decomposition of hydroperoxides to alcohols utilizing new compositions of matter, which are metal complexes of porphyrins. Preferred complexes have hydrogen, haloalkyl or haloaryl groups in meso positions, two of the opposed meso atoms or groups being hydrogen or haloaryl, and two of the opposed meso atoms or groups being hydrogen or haloalkyl, but not all four of the meso atoms or groups being hydrogen. Other preferred complexes are ones in which all four of the meso positions are substituted with haloalkyl groups and the beta positions are substituted with halogen atoms. A new method of synthesizing porphyrinogens is also disclosed.Type: GrantFiled: June 27, 1996Date of Patent: March 3, 1998Assignee: Sun Company, Inc. (R&M)Inventors: Tilak Wijesekera, James E. Lyons, Paul E. Ellis, Jr.
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Patent number: 5672778Abstract: The invention comprises a method for the catalytic conversion of alkanes and alkylhydroperoxides to oxygenates, particularly alcohols, comprising the oxidation of alkanes to yield alkylhydroperoxides, alcohols, other reaction products and unreacted alkane, and the decomposition of said alkylhydroperoxides to form alcohols and oxygen. Decomposition of the alkylhydroperoxide in the presence of unreacted alkane increases the yield of alcohol. The process further comprises drying of the reaction mixture comprising alkylhydroperoxide. Suitable catalysts for the process of the invention comprise metal containing catalysts, including metal organic ligand catalysts such as unsubstituted and substituted metal complexes of porphyrins, phthalocyanines and acetylacetonates.Type: GrantFiled: August 26, 1996Date of Patent: September 30, 1997Assignee: Sun Company, Inc. (R & M)Inventors: James E. Lyons, Paul E. Ellis, Jr., Manoj V. Bhinde
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Patent number: 5639922Abstract: A process is described for the selective decomposition of aromatic primary hydroperoxides by contacting a hydroperoxide mixture containing aromatic primary hydroperoxides and aromatic tertiary hydroperoxides obtained by oxidation of alkylaromatic compounds under non-aqueous conditions with an alkali and an organic aromatic carboxylic acid salt.Type: GrantFiled: July 14, 1995Date of Patent: June 17, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Yoichi Ikeda, Motoo Hazama, Nobuhiro Kawara, Maki Okumura, Takanori Ito
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Patent number: 5550301Abstract: Organic hydroperoxides are decomposed by drying a reaction mixture containing the organic hydroperoxide and an organic solvent such that said dried reaction mixture comprises approximately 1 weight percent or less of water and contacting the dried reaction mixture with a metal organic ligand catalyst under hydroperoxide decomposition conditions. An organic co-solvent for the hydroperoxide may also be used. Particularly effective catalysts are cobalt acetylacetonates and ruthenium acetylacetonates and combinations thereof.Type: GrantFiled: March 3, 1995Date of Patent: August 27, 1996Assignee: Sun Company, Inc. (R&M)Inventors: Manoj V. Bhinde, James E. Lyons, Paul E. Ellis, Jr.
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Patent number: 5489716Abstract: The invention provides novel methods for the oxidation of hydrocarbons with oxygen-containing gas to form hydroxy-group containing compounds and for the decomposition of hydroperoxides to form hydroxygroup containing compounds. The catalysts used in the methods of the invention comprise transition metal complexes of a porphyrin ring having 1 to 12 halogen substituents on the porphyrin ring, at least one of said halogens being in a meso position and/or the catalyst containing no aryl group in a meso position. The catalyst compositions are prepared by halogenating a transition metal complex of a porphyrin.Type: GrantFiled: September 7, 1994Date of Patent: February 6, 1996Assignee: Sun Company, Inc. (R&M)Inventors: Paul E. Ellis, Jr., James E. Lyons
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Patent number: 5426237Abstract: The present invention provides a process for the oxidation of straight-chain, branched-chain or cyclic alkanes of 1-20 carbon atoms and benzene derivatives represented by the following formulas (1)-(2). The alcohols and ketones obtained by the oxidation of the alkanes mentioned above and those by the oxidation of the benzene derivatives mentioned above represented by the following formulas (3)-(6) are important as basic starting materials in producing various chemical products including resins, such as nylon and polyester, pharmaceuticals, agricultural chemicals, perfumes, dyes, etc.Type: GrantFiled: March 24, 1994Date of Patent: June 20, 1995Assignee: Sumitomo Chemical Co., Ltd.Inventors: Shun-Ichi Murahashi, Yoshiaki Oda
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Patent number: 5395988Abstract: Organic hydroperoxides are decomposed by drying a reaction mixture containing the organic hydroperoxide and an organic solvent and contacting the dried reaction mixture with a metal organic ligand catalyst under hydroperoxide decomposition conditions. An organic co-solvent for the hydroperoxide may also be used.Type: GrantFiled: April 4, 1994Date of Patent: March 7, 1995Assignee: Sun Company, Inc. (R&M)Inventors: Manoj V. Bhinde, James E. Lyons, Paul E. Ellis, Jr.
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Patent number: 5345008Abstract: Hydroperoxides are decomposed by contact with metalloporphyrin coordination complex catalysts in which hydrogen in the porphyrin molecule has been substituted with at least one nitro group and may be further substituted with other electron-withdrawing elements or groups, for example, halogen or halocarbons, or with hydrocarbon groups. Preferred catalysts are iron tetranitro-.beta.-octaethylporphyrins and iron tetrakispentafluorophenyl-.beta.-nitroporphyrins.Type: GrantFiled: June 9, 1993Date of Patent: September 6, 1994Assignee: Sun Company, Inc. (R&M)Inventors: James E. Lyons, Paul E. Ellis, Jr.
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Patent number: 5233092Abstract: The invention relates to a new compound of the formular (1): ##STR1## wherein m.sub.1 =0, 1 or 2, m.sub.2 =0, 1 or 2, m.sub.1 and m.sub.2 are not to be simultaneously 0 or simultaneously 2; n.sub.1 =2-m.sub.1, n.sub.2 =2-m.sub.2 ; R=either H or alkyl with 1 to 8 carbon atoms, R'=alkyl with 1 through 18 carbon atoms, and X=H or OH.The invention also relates to the preparation thereof, the compositions containing them and the application in catalysis of oxidation of hydrocarbons, particularly in catalysis of oxidation of cyclohexane.Type: GrantFiled: January 17, 1992Date of Patent: August 3, 1993Inventor: Xiao Zaosheng
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Patent number: 5206424Abstract: A method for preparing tertiary butyl alcohol wherein a solution of a tertiary butyl hydroperoxide in tertiary butyl alcohol is charged to a hydroperoxide decomposition reaction zone containing a catalytically effective amount of a soluble iron hydroperoxide decomposition catalyst consisting essentially of a soluble cycloalkenyl iron compound and is brought into contact with the soluble cycloalkenyl iron compound in liquid phase with agitation under hydroperoxide decomposition reaction conditions to convert the tertiary butyl hydroperoxide to decomposition products, principally tertiary butyl alcohol.Type: GrantFiled: September 8, 1992Date of Patent: April 27, 1993Assignee: Texaco Chemical CompanyInventors: John R. Sanderson, John F. Knifton
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Patent number: 5171868Abstract: Caustic requirements are substantially reduced in the treatment of epoxidate from olefin/ethylbenzene hydroperoxide epoxidation by treating the epoxidate products with an aqueous stream comprised of alkali metal carbonate, separating a phenol-containing 1-phenyl ethanol fraction from the treated expodiate, separating phenol from the 1-phenyl ethanol fraction by treatment with basic anion exchange resin, regenerating the resin with aqueous alkali metal hydroxide, and converting alkali metal hydroxide from the resin regeneration to alkali metal carbonate for use in the epoxidate treatment.Type: GrantFiled: April 15, 1992Date of Patent: December 15, 1992Assignee: ARCO Chemical Technology, L.P.Inventors: Rajendra S. Albal, Robert N. Cochran, T. Ben Hsu
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Patent number: 5160496Abstract: The phenols and phenol ethers are economically and efficiently hydroxylated using hydrogen peroxide, in the presence of a catalytically effective amount of a bridged clay, e.g., a zeolite or smectite.Type: GrantFiled: July 16, 1990Date of Patent: November 3, 1992Assignee: Rhone-Poulenc ChimieInventors: Michel Constantini, Jean-Michel Popa
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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: 5126494Abstract: Osmium-catalyzed methods of addition to an olefin are discussed. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, water, an oxidant and an osmium-containing compound are combined. In the method of asymmetric oxyamination of the present invention, an olefin, a chiral ligand, an organic solvent, water, a metallo-chloramine derivative, an osmium-containing compound and, optionally, a tetraalkyl ammonium compound are combined. In the method of asymmetric diamination of the present invention, an olefin, a chiral ligand, an organic solvent, a metallo-chloramine derivative, an amine and an osmium-containing compound are combined. In one embodiment, an olefin, a chiral ligand which is a polymeric dihydroquinidine derivative or a dihydroquinine derivative, acetone, water, a base, an oxidant and osmium tetroxide are combined to effect asymmetric dihydroxylation of the olefin.Type: GrantFiled: April 23, 1990Date of Patent: June 30, 1992Assignee: Massachusetts Institute of TechnologyInventors: Declan Gilheany, Byeong M. Kim, Hoi-Lun Kwong, K. Barry Sharpless, Tomoyuki Shibata
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Patent number: 5120886Abstract: Hydroperoxides are decomposed by contact with metal ligand catalysts of coordination complexes in which hydrogen in the ligand molecule has been substituted with electron-withdrawing elements or groups, for example halogen or nitro or cyano groups. Preferred catalysts are iron perhaloporphyrins.Type: GrantFiled: July 9, 1991Date of Patent: June 9, 1992Assignee: Sun Refining and Marketing CompanyInventors: James E. Lyons, Paul E. Ellis, Jr.
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Patent number: 5041680Abstract: Hydrogen peroxide and organic active oxygen-containing compounds in an organic stream, such as that from a methyl benzyl alcohol oxidate after hydrogen peroxide separation, are selectively decomposed by non-catalytic thermal treatment at 150.degree.-180.degree. C. for 20-60 minutes whereby the organic active oxygen materials selectively decompose to acetophenone and methyl benzyl alcohol.Type: GrantFiled: February 19, 1991Date of Patent: August 20, 1991Assignee: Arco Chemical Technology, Inc.Inventors: Rajendra S. Albal, Robert N. Cochran, Alan P. Woinsky
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Patent number: 5023383Abstract: Aromatic alcohol is produced by reducing aromatic hydroperoxide with hydrogen in a liquid phase, using a Pt catalyst solely or a catalyst containing Pt and at least one element selected from the group consisting Pb, Sn, Cu, As, Sb, In, Se and Bi in a fixed bed reactor.Type: GrantFiled: January 3, 1990Date of Patent: June 11, 1991Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Masashi Inaba, Ryozo Hamana, Hideyuki Hase, Tatsuro Ashizawa
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Patent number: 5021607Abstract: Saturated hydrocarbon chains are oxidized using a titanium containing silicalite catalyst having an infra red absorption band around 950 cm.sup.-1 preferably in solutions, the chains may be alkanes or alkyl groups of alkyl cyclic compounds.Type: GrantFiled: September 10, 1990Date of Patent: June 4, 1991Assignee: Exxon Chemical Patents Inc.Inventor: Diana R. Huybrechts
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Patent number: 4994625Abstract: Hydrogen peroxide and organic active oxygen-containing compounds in an organic stream, such as that from a methyl benzyl alcohol oxidate after hydrogen peroxide separation, are selectively decomposed by contact with an alumina catalyst, the organic active oxygen materials selectively decomposing to acetophenone and methyl benzyl alcohol.Type: GrantFiled: December 27, 1989Date of Patent: February 19, 1991Assignee: Arco Chemical Technology, Inc.Inventors: Rajendra S. Albal, Robert N. Cochran
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Patent number: 4970346Abstract: A process for the production of detergent range alcohols and ketones by reacting an alkane with a hydroperoxide in the presence of dicyano bis-(1,10-phenanthrolene)iron(II) is described. Preferred hydroperoxides include cumene hydroperoxide and tertiary butyl hydroperoxide.Type: GrantFiled: October 30, 1989Date of Patent: November 13, 1990Assignee: Texaco Chemical CompanyInventors: John R. Sanderson, Edward T. Marquis
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Patent number: 4943667Abstract: Phenylethanols of the formula ##STR1## where R is hydrogen, alkyl of from 1 to 4 carbon atoms, alkoxy of from 1 to 4 carbon atoms, fluorine, trifluoromethyl or trifluoromethoxy, are prepared by reacting epoxides of the formula ##STR2## where R is as defined above, in the presence of hydrogen over zeolites and/or phosphates, doped with hydrogenating metal as catalysts, preferably over zeolites of the pentasil type.Type: GrantFiled: January 13, 1989Date of Patent: July 24, 1990Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer
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Patent number: 4879416Abstract: The process for preparing a bidentate ligand comprising the steps,(1) contacting with ozone under ozonolysis conditions a suspension in a hydroxylic reaction medium of phenanthrene or a phenanthrene derivative to form an ozonated intermediate,(2) contacting said ozonated intermediate with a reducing agent under conditions appropriate to form the corresponding diol,(3) contacting said diol with a latent displaceable functional group under conditions appropriate to convert the diol to the corresponding difunctional biaryl compound, and(4) contacting said difunctional biaryl compound, with an anion of N, P, As, Sb or Bi under conditions appropriate to form the desired bidentate ligand.Type: GrantFiled: November 23, 1987Date of Patent: November 7, 1989Assignee: Eastman Kodak CompanyInventors: Thomas A. Puckette, Thomas J. Devon, Gerald W. Phillips, Jerome L. Stavinoha
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Patent number: 4825007Abstract: An aromatic compound selected from benzene and biphenyl compounds containing at least one isopropyl group is oxidized to convert at least one of the at least one isopropyl group into a 2-hydroxy-2-propyl group. The oxidation of the aromatic compound is effected with molecular oxygen in the presence of an aqueous alkali solution in an oxidative reaction vessel made of nickel at parts thereof where the vessel comes into contact with a reaction mixture. In particular, the above process suppresses the formation of by-products and permits long-term oxidation on an industrial scale.Type: GrantFiled: November 4, 1987Date of Patent: April 25, 1989Assignee: Kureha Kagaku Kogyo K.K.Inventors: Yutaka Konai, Kazuo Yoshida, Masatoshi Hino
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Patent number: 4746757Abstract: Disclosed herein is a process for producing (2-hydroxy-2-propyl)naphthalene compounds, comprising oxidizing a naphthalene compound having isopropyl group(s) on the naphthalene ring in the presence of peroxodisulfate in a mixed solvent of water and an organic polar solvent.Type: GrantFiled: July 17, 1986Date of Patent: May 24, 1988Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Takashi Terauchi, Tadashi Nakamura, Shoichi Hoshi