Preparing From A Peroxide Or Preparing By Oxidation Patents (Class 568/815)
  • Patent number: 8957255
    Abstract: 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: Grant
    Filed: October 4, 2013
    Date of Patent: February 17, 2015
    Assignee: Jawaharlal Nehru Centre for Advanced Scientific Research
    Inventors: Chintamani Nagesa Ramachandra Rao, Ujjal Kam Gautam, Srinivasa Rao Lingampalli
  • Publication number: 20140171689
    Abstract: 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: Application
    Filed: October 4, 2013
    Publication date: June 19, 2014
    Applicant: Jawaharlal Nehru Centre for Advanced Scientific Research
    Inventors: Chintamani Nagesa Ramachandra Rao, Ujjal Kam Gautam, Srinivasa Rao Lingampalli
  • Publication number: 20130172610
    Abstract: 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: Application
    Filed: December 29, 2011
    Publication date: July 4, 2013
    Applicant: UOP LLC
    Inventors: Alakananda Bhattacharyya, Raymond C. Shih
  • Publication number: 20130041175
    Abstract: 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: Application
    Filed: October 12, 2012
    Publication date: February 14, 2013
    Applicant: UOP LLC
    Inventors: Alakananda Bhattacharyya, Raymond Shih
  • Patent number: 8106242
    Abstract: 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: Grant
    Filed: May 23, 2007
    Date of Patent: January 31, 2012
    Assignee: DSM IP Assets B.V.
    Inventors: Rafael Wilhelmus Elisabeth Ghislain Reintjens, Quirinus Bernardus Broxterman, Martina Kotthaus, Peter Poechlauer
  • Patent number: 7888537
    Abstract: 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: Grant
    Filed: December 19, 2007
    Date of Patent: February 15, 2011
    Assignee: UOP LLC
    Inventors: Robert J. Schmidt, Deng-Yang Jan, Raelynn M. Miller, James A. Johnson
  • Patent number: 7868201
    Abstract: 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: Grant
    Filed: July 1, 2005
    Date of Patent: January 11, 2011
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Bi-Zeng Zhan, Bjorn Moden, Jihad Dakka, Jose Santiesteban, Sebastian C. Reyes, Enrique Iglesia
  • Publication number: 20090192337
    Abstract: 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: Application
    Filed: October 30, 2008
    Publication date: July 30, 2009
    Applicant: COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH
    Inventors: Suman Lata JAIN, Jomy K. JOSEPH, Sweety SINGHAL, Bir SAIN, Ragunathan SIVAKUMARAN, Basant KUMAR
  • Patent number: 7166754
    Abstract: 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: Grant
    Filed: March 4, 2002
    Date of Patent: January 23, 2007
    Assignee: California Institute of Technology
    Inventors: Eric M. Ferreira, Brian M. Stoltz
  • Patent number: 7148386
    Abstract: 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: Grant
    Filed: July 30, 2004
    Date of Patent: December 12, 2006
    Assignee: General Electric Company
    Inventors: Jegadeesh Thampi, Sunil Ashtekar, Pramod Kumbhar, Rathinam Jothi Mahalingam
  • Patent number: 7094925
    Abstract: 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: Grant
    Filed: October 5, 2001
    Date of Patent: August 22, 2006
    Assignee: The Queen's University of Belfast
    Inventors: Martyn John Earle, Suhas Prabhakar Katdare
  • Patent number: 7038068
    Abstract: 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: Grant
    Filed: March 16, 2004
    Date of Patent: May 2, 2006
    Assignee: Hitachi Global Storage Technologies Netherlands B.V.
    Inventor: John M. Burns
  • Patent number: 6974888
    Abstract: 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: Grant
    Filed: January 14, 2004
    Date of Patent: December 13, 2005
    Assignee: Shell Oil Company
    Inventors: Antoon Paul Michael Kremers, Eduardus Petrus Simon Schouten, Cornelis Willem Adriaan Schram
  • Patent number: 6849771
    Abstract: 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: Grant
    Filed: August 6, 2003
    Date of Patent: February 1, 2005
    Assignee: Shell Oil Company
    Inventors: Timothy Michael Nisbet, Eduardus Petrus Simon Schouten, Cornelis Willem Adriaan Schram
  • Patent number: 6743952
    Abstract: 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: Grant
    Filed: March 28, 2002
    Date of Patent: June 1, 2004
    Assignee: Council of Scientific and Industrial Research
    Inventors: Mannepalli Lakshmi Kantham, Pentlavalli Sreekanth, Kottapalli Koteshwara Rao, Thella Prathap Kumar, Bhavnari Purna C. Rao, Boyapati Manoranjan Choudary
  • Patent number: 6700005
    Abstract: 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: Grant
    Filed: February 6, 2003
    Date of Patent: March 2, 2004
    Assignee: Shell Oil Company
    Inventors: Antoon Paul Michael Kremers, Eduardus Petrus Simon Schouten, Cornelis Willem Adriaan Schram
  • Patent number: 6590129
    Abstract: An aromatic carboxylic acid, aromatic aldehyde, and aromatic alcohol are simultaneously and efficiently prepared by liquid phase oxidizing an aromatic compound represented by formula (I) with a gas containing molecular oxygen, in a presence of a catalyst comprising transition metal compound, tertiary amine and bromide compound:
    Type: Grant
    Filed: March 19, 2001
    Date of Patent: July 8, 2003
    Assignee: Toray Industries, Inc.
    Inventors: Shotaro Matsuoka, Masaaki Suematsu, Akira Kitamura
  • Publication number: 20030055297
    Abstract: A process for the preparation of neuraminidase inhibitors having structural formula (28) 1
    Type: Application
    Filed: April 3, 2002
    Publication date: March 20, 2003
    Inventors: 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
  • Patent number: 6437176
    Abstract: An aromatic carboxylic acid, aromatic aldehyde, and aromatic alcohol are simultaneously and efficiently prepared by liquid phase oxidizing an aromatic compound represented by formula (I) with a gas containing molecular oxygen, in a presence of a catalyst comprising transition metal compound, tertiary amine and bromide compound:
    Type: Grant
    Filed: March 19, 2001
    Date of Patent: August 20, 2002
    Assignee: Toray Industries, Inc.
    Inventors: Shotaro Matsuoka, Masaaki Suematsu, Akira Kitamura
  • Publication number: 20020045781
    Abstract: 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: Application
    Filed: October 18, 2001
    Publication date: April 18, 2002
    Applicant: PHENOLCHEMIE GMBH & CO. KG
    Inventors: Uwe Tanger, Manfred Weber
  • Publication number: 20010018543
    Abstract: An aromatic carboxylic acid, aromatic aldehyde, and aromatic alcohol are simultaneously and efficiently prepared by liquid phase oxidizing an aromatic compound represented by formula (I) with a gas containing molecular oxygen, in a presence of a catalyst comprising transition metal compound, tertiary amine and bromide compound: 1
    Type: Application
    Filed: March 19, 2001
    Publication date: August 30, 2001
    Applicant: Toray Industries, Inc.
    Inventors: Shotaro Matsuoka, Masaaki Suematsu, Akira Kitamura
  • Patent number: 6281382
    Abstract: 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: Grant
    Filed: June 1, 2000
    Date of Patent: August 28, 2001
    Assignee: Georgia Tech Research Corp.
    Inventors: Mark G. White, Alexei V. Iretski
  • Patent number: 6271425
    Abstract: 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: Grant
    Filed: September 7, 1999
    Date of Patent: August 7, 2001
    Assignees: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Eiichi Nakamura, Masaya Sawamura
  • Patent number: 6242643
    Abstract: An aromatic carboxylic acid, aromatic aldehyde, and aromatic alcohol are simultaneously and efficiently prepared by liquid phase oxidizing an aromatic compound represented by formula (I) with a gas containing molecular oxygen, in a presence of a catalyst comprising transition metal compound, tertiary amine and bromide compound:
    Type: Grant
    Filed: May 13, 1997
    Date of Patent: June 5, 2001
    Assignee: Toray Industries, Inc.
    Inventors: Shotaro Matsuoka, Masaaki Suematsu, Akira Kitamura
  • Patent number: 6218581
    Abstract: 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: Grant
    Filed: August 6, 1999
    Date of Patent: April 17, 2001
    Assignee: Sanyo Shokuhin Co., Ltd.
    Inventor: Hiroyuki Nagaoka
  • Patent number: 6002037
    Abstract: 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: Grant
    Filed: October 14, 1997
    Date of Patent: December 14, 1999
    Assignee: Purdue Research Foundation
    Inventors: Ei-ichi Negishi, Denis Y. Kondakov
  • Patent number: 5723677
    Abstract: 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: Grant
    Filed: June 27, 1996
    Date of Patent: March 3, 1998
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Tilak Wijesekera, James E. Lyons, Paul E. Ellis, Jr.
  • Patent number: 5672778
    Abstract: 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: Grant
    Filed: August 26, 1996
    Date of Patent: September 30, 1997
    Assignee: Sun Company, Inc. (R & M)
    Inventors: James E. Lyons, Paul E. Ellis, Jr., Manoj V. Bhinde
  • Patent number: 5639922
    Abstract: 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: Grant
    Filed: July 14, 1995
    Date of Patent: June 17, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoichi Ikeda, Motoo Hazama, Nobuhiro Kawara, Maki Okumura, Takanori Ito
  • Patent number: 5550301
    Abstract: 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: Grant
    Filed: March 3, 1995
    Date of Patent: August 27, 1996
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Manoj V. Bhinde, James E. Lyons, Paul E. Ellis, Jr.
  • Patent number: 5489716
    Abstract: 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: Grant
    Filed: September 7, 1994
    Date of Patent: February 6, 1996
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Paul E. Ellis, Jr., James E. Lyons
  • Patent number: 5426237
    Abstract: 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: Grant
    Filed: March 24, 1994
    Date of Patent: June 20, 1995
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Shun-Ichi Murahashi, Yoshiaki Oda
  • Patent number: 5395988
    Abstract: 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: Grant
    Filed: April 4, 1994
    Date of Patent: March 7, 1995
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Manoj V. Bhinde, James E. Lyons, Paul E. Ellis, Jr.
  • Patent number: 5345008
    Abstract: 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: Grant
    Filed: June 9, 1993
    Date of Patent: September 6, 1994
    Assignee: Sun Company, Inc. (R&M)
    Inventors: James E. Lyons, Paul E. Ellis, Jr.
  • Patent number: 5233092
    Abstract: 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: Grant
    Filed: January 17, 1992
    Date of Patent: August 3, 1993
    Inventor: Xiao Zaosheng
  • Patent number: 5206424
    Abstract: 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: Grant
    Filed: September 8, 1992
    Date of Patent: April 27, 1993
    Assignee: Texaco Chemical Company
    Inventors: John R. Sanderson, John F. Knifton
  • Patent number: 5171868
    Abstract: 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: Grant
    Filed: April 15, 1992
    Date of Patent: December 15, 1992
    Assignee: ARCO Chemical Technology, L.P.
    Inventors: Rajendra S. Albal, Robert N. Cochran, T. Ben Hsu
  • Patent number: 5160496
    Abstract: 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: Grant
    Filed: July 16, 1990
    Date of Patent: November 3, 1992
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Constantini, Jean-Michel Popa
  • Patent number: 5149880
    Abstract: Nitrogen-containing aromatic heterocyclic ligand-metal complexes and their use for the activation of hydrogen peroxide and dioxgen are disclosed. Processes whereby activated hydrogen peroxide or dioxygen are used to transform various organic substrates are also disclosed. In particular, processes for the conversion of methylenic carbons to carbonyls, for the dioxygenation of aryl olefins, acetylenes and aryl-.alpha.-diols, for the oxidation of alcohols and aldehydes and for the removal of mercaptans from gaseous streams and for the removal of hydrogen sulfide and/or mercaptans from liquid streams are disclosed.
    Type: Grant
    Filed: August 24, 1990
    Date of Patent: September 22, 1992
    Assignee: The Texas A & M University System
    Inventors: Donald T. Sawyer, Ceshing Sheu, Andrzej Sobkowiak, Hui-Chan Tung
  • Patent number: 5126494
    Abstract: 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: Grant
    Filed: April 23, 1990
    Date of Patent: June 30, 1992
    Assignee: Massachusetts Institute of Technology
    Inventors: Declan Gilheany, Byeong M. Kim, Hoi-Lun Kwong, K. Barry Sharpless, Tomoyuki Shibata
  • Patent number: 5120886
    Abstract: 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: Grant
    Filed: July 9, 1991
    Date of Patent: June 9, 1992
    Assignee: Sun Refining and Marketing Company
    Inventors: James E. Lyons, Paul E. Ellis, Jr.
  • Patent number: 5041680
    Abstract: 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: Grant
    Filed: February 19, 1991
    Date of Patent: August 20, 1991
    Assignee: Arco Chemical Technology, Inc.
    Inventors: Rajendra S. Albal, Robert N. Cochran, Alan P. Woinsky
  • Patent number: 5023383
    Abstract: 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: Grant
    Filed: January 3, 1990
    Date of Patent: June 11, 1991
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventors: Masashi Inaba, Ryozo Hamana, Hideyuki Hase, Tatsuro Ashizawa
  • Patent number: 5021607
    Abstract: 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: Grant
    Filed: September 10, 1990
    Date of Patent: June 4, 1991
    Assignee: Exxon Chemical Patents Inc.
    Inventor: Diana R. Huybrechts
  • Patent number: 4994625
    Abstract: 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: Grant
    Filed: December 27, 1989
    Date of Patent: February 19, 1991
    Assignee: Arco Chemical Technology, Inc.
    Inventors: Rajendra S. Albal, Robert N. Cochran
  • Patent number: 4970346
    Abstract: 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: Grant
    Filed: October 30, 1989
    Date of Patent: November 13, 1990
    Assignee: Texaco Chemical Company
    Inventors: John R. Sanderson, Edward T. Marquis
  • Patent number: 4943667
    Abstract: 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: Grant
    Filed: January 13, 1989
    Date of Patent: July 24, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer
  • Patent number: 4879416
    Abstract: 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: Grant
    Filed: November 23, 1987
    Date of Patent: November 7, 1989
    Assignee: Eastman Kodak Company
    Inventors: Thomas A. Puckette, Thomas J. Devon, Gerald W. Phillips, Jerome L. Stavinoha
  • Patent number: 4825007
    Abstract: 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: Grant
    Filed: November 4, 1987
    Date of Patent: April 25, 1989
    Assignee: Kureha Kagaku Kogyo K.K.
    Inventors: Yutaka Konai, Kazuo Yoshida, Masatoshi Hino
  • Patent number: 4746757
    Abstract: 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: Grant
    Filed: July 17, 1986
    Date of Patent: May 24, 1988
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Takashi Terauchi, Tadashi Nakamura, Shoichi Hoshi