Oxidation Utilizing Gaseous Oxygen Patents (Class 568/344)
  • Patent number: 11428681
    Abstract: A sensor can include a conductive region in electrical communication with at least two electrodes, the conductive region including a conductive material and an alkene-interacting metal complex.
    Type: Grant
    Filed: November 4, 2019
    Date of Patent: August 30, 2022
    Assignee: Massachusetts Institute of Technology
    Inventors: Timothy M. Swager, Sophie Liu, Graham Sazama, Alexander R. Petty, Jan M. Schnorr
  • Patent number: 9035102
    Abstract: A process for preparing isophorone (3,5,5-trimethyl-2-cyclohexen-1-one) is provided wherein distillation vapors from the work-up of product fractions are recycled to earlier stages of operation of the process.
    Type: Grant
    Filed: August 8, 2014
    Date of Patent: May 19, 2015
    Assignee: Evonik Industries AG
    Inventors: Joerg-Joachim Nitz, Stephan Kohlstruk, Robert Jansen, Matthias Orschel, Andreas Merkel, Michael Demming, Matthias Mendorf, Jens Doering, Axel Hengstermann, Andreas Hoff, Anja Mueller
  • Publication number: 20150132811
    Abstract: The invention herein disclosed provides for compositions, methods for synthesizing said compositions, and methods for using said compositions, wherein the compositions and methods may be used to bind to and/or deactivate a poison oak oil, such as urushiol. The compositions and methods can be used to treat and/or reduce an inflammatory reaction and/or hypersensitivity to natural compounds found in poison oak, poison ivy, poison sumac, mango, lac tree, cashew nut, and Asian lacquer.
    Type: Application
    Filed: May 1, 2013
    Publication date: May 14, 2015
    Inventor: Rebecca Braslau
  • Patent number: 8981157
    Abstract: A catalyst, its method of preparation and its use for producing aliphatic ketones by subjecting alkanes C3 to C9 to a gas phase catalytic oxidation in the presence of air or oxygen, and, optionally, steam and/or one or more diluting gases. The catalyst comprises a catalytically active mixed metal oxide phase and a suitable support material onto and/or into which the active catalytic phase id dispersed.
    Type: Grant
    Filed: May 9, 2012
    Date of Patent: March 17, 2015
    Assignee: Ever Nu Technology, LLC
    Inventors: Manhua Lin, Xiang Wang, Younghoon Yeom
  • Publication number: 20130172625
    Abstract: Methods for using ailylic oxidation catalysts to perform oxidation reactions. In an exemplary method for catalyzing an ailylic oxidation reaction of the present disclosure, the method comprises the step of catalyzing an oxidation of an ailylic compound using an ailylic oxidation catalyst. In at least one embodiment, the ailylic oxidation catalyst comprises palladium, gold, and titanium, In an exemplary embodiment, the ailylic oxidation catalyst comprises 2.5% A?÷2.5% Pd/TiO2.
    Type: Application
    Filed: February 10, 2011
    Publication date: July 4, 2013
    Inventors: Brian Tarbit, Graham J. Hutchings, Jennifer K. Edwards, Peter Miedziak
  • Publication number: 20120197036
    Abstract: A method for manufacturing a ketone, includes oxidizing an internal olefin or a cyclic olefin having a functional group containing a hetero atom and one carbon-carbon double bond or more at a position other than terminals of a molecule thereof in an amide-based solvent in the presence of water, a palladium catalyst, and molecular oxygen, without oxidizing the functional group, thereby bonding an oxo group to at least one of the carbon atoms constituting the carbon-carbon double bond. The amide-based solvent is represented by formula (1): wherein R1 represents an alkyl group having 1 to 4 carbon atoms; R2 and R3 each independently represent an alkyl group having 1 to 4 carbon atoms or an aryl group; and when R1 and R2 are alkyl groups, R1 and R2 may be bonded to each other to form a ring structure.
    Type: Application
    Filed: October 8, 2010
    Publication date: August 2, 2012
    Applicants: Osaka University, JX NIPPON OIL & ENERGY CORPORATION
    Inventors: Kiyotomi Kaneda, Hisashi Sone
  • Patent number: 7858828
    Abstract: (3R,3?R,6?R)-Lutein and (3R,3?R)-zeaxanthin are two dietary carotenoids that are present in most fruits and vegetables commonly consumed in the US. These carotenoids accumulate in the human plasma, major organs, and ocular tissues. In the past decade, numerous epidemiological and experimental studies have shown that lutein and zeaxanthin play an important role in the prevention of age-related macular degeneration (AMD) that is the leading cause of blindness in the U.S. and Western World. The invention provides a process for the synthesis of (3R,3?R,6?R)-lutein and its stereoisomers from commercially available (rac)-?-ionone by a C15+C10+C15 coupling strategy. In addition, the present invention also provides access to the precursors of optically active carotenoids with 3-hydroxy-?-end group that are otherwise difficult to synthesize. The process developed for the synthesis of lutein and its stereoisomers is straightforward and has potential for commercialization.
    Type: Grant
    Filed: March 25, 2009
    Date of Patent: December 28, 2010
    Assignee: University of Maryland, College Park
    Inventors: Frederick Khachik, An-Ni Chang
  • Patent number: 7285684
    Abstract: A reaction mixture obtained by reacting a substrate in the presence of an imide compound having an imide unit represented by the formula (1) can be efficiently separated through crystallization and/or extraction with a specific solvent into the imide compound and a reaction product. (In the formula, X represents oxygen, hydroxyl, or acyloxy.) Furthermore, a mixture comprising the imide compound and a metal catalyst can be efficiently separated through crystallization, adsorption, and/or extraction into the imide compound and the metal catalyst.
    Type: Grant
    Filed: March 30, 2001
    Date of Patent: October 23, 2007
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Hiroyuki Miura, Hitoshi Watanabe, Akihiro Kuwana, Mami Shimamura, Naruhisa Hirai
  • Patent number: 7282611
    Abstract: The present invention provides a process for the preparation of a mixture of alcohols and ketones by the liquid phase oxidation of isoalkanes to alkyl hydroperoxides with simultaneous transfer of oxygen to alkanes (C8-C20) in presence of oxides alkaline earth metals like magnesium, calcium, barium and strontium and oxides of rare earth metals such as lanthanum, cerium, samarium, neodymium and europium, at a temperature ranging between 110°-160° C. and air pressure ranging between 10-1500 psig for a period of 0.5-20 h, cooling the reaction mixture to 5° C., separating the products by conventional methods such as distillation. The catalyst reused for several times without affecting its catalytic performance.
    Type: Grant
    Filed: September 25, 2006
    Date of Patent: October 16, 2007
    Assignee: Council of Scientific and Industrial Research
    Inventors: Deshpande Raj Madhukar, Rane Vilas Hari, Chaudhari Raghunath Vithal
  • Patent number: 7166751
    Abstract: The object of the present invention is to provide a method for manufacturing cycloalkanol and/or cycloalkanone with favorable selectivity coefficient by oxidizing cycloalkane with favorable degree of conversion. In the present invention, cycloalkane is oxidized with oxygen in the presence of a catalyst such that gold is supported on ceric oxide. Said oxidation is preferably performed in the presence of a free-radical initiator and the free-radical initiator is preferably 2,2?-azobis(isobutyronitrile).
    Type: Grant
    Filed: March 28, 2006
    Date of Patent: January 23, 2007
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Avelino Corma, Jose Manuel Lopez Nieto
  • Patent number: 7145041
    Abstract: The invention relates to a method for catalytically oxidizing unsaturated hydrocarbons to form oxidation products, and to the production of saturated alcohols, ketones, aldehydes or carboxylic acids by subsequently hydrogenating the oxidation product. A compound of formula (I) is used as a catalyst during oxidizing in which: R1, R2=H, an aliphatic or aromatic alkoxy radical, carboxyl radical, alkoxycarbonyl radical or hydrocarbon radical, each having 1 to 20 carbon atoms, SO3H, NH2, OH, F, Cl, Br, I and/or NO2, whereby R1 and R2 signify identical or different radicals or R1 and R2 can be coupled to one another via a covalent bond, with Q1, Q2=the same or different, C, CH, N; X, Z=C, S or CH2; Y=O or OH; k=0, 1 or 2; 1=0, 1 or 2; m=1 to 100 in the presence of a radical initiator. Peroxy compounds or azo compounds can be used as radical initiators. Preferred substrates are cyclic aliphatic or aromatic compounds.
    Type: Grant
    Filed: June 12, 2002
    Date of Patent: December 5, 2006
    Assignee: Degussa AG
    Inventors: Adolf Kuehnle, Carsten Jost, Roger Arthur Sheldon, Sandrine M. M. Chatel, Isabella W. C. E. Arends
  • Patent number: 7087793
    Abstract: The present invention provides a process for producing cycloalkanol and/or cycloalkanone by oxidizing cycloalkane with molecular oxygen in the presence of a heteropolyacid compound comprising a cobalt atom as a central element and a cobalt atom as a frame element.
    Type: Grant
    Filed: August 26, 2005
    Date of Patent: August 8, 2006
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Avelino Corma, Jose Manuel Lopez Nieto
  • Patent number: 6806390
    Abstract: An improved catalytic process for decomposing alkyl or aromatic hydroperoxides is disclosed which utilizes a caalytic amount of a heterogeneous Au catalyst that has been treated with an organosilicon reagent.
    Type: Grant
    Filed: February 11, 2003
    Date of Patent: October 19, 2004
    Assignee: Inuista North America S.àr.l.
    Inventors: Norman Herron, Stephan Schwarz, Joe Douglas Druliner
  • Patent number: 6703529
    Abstract: Disclosed herein is a process for the production of a mixture of cyclohexanone and cyclohexanol by oxidation of cyclohexane and decomposition of cyclohexyl hydroperoxide.
    Type: Grant
    Filed: September 12, 2002
    Date of Patent: March 9, 2004
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Ludovic Fodor, Bhagya Chandra Sutradhar
  • Patent number: 6677490
    Abstract: The invention relates to a method for producing a mixture of alcohols/ketones by decomposing an alkyl hydroperoxide, particularly to a method for producing a cyclohexanol/cyclohexanone by decomposing cyclohexyl hydroperoxide in the presence of a heterogeneous catalyst. According to the invention, the reaction is carried out in the presence of a heterogeneous catalyst containing an organometallic segment fixed on the surface of a porous solid compound such as silicon. The organometallic segment can be formula (I).
    Type: Grant
    Filed: October 15, 2002
    Date of Patent: January 13, 2004
    Assignee: Rhodia Polyamide Intermediates
    Inventors: James Clark, Eric Fache, Ducan Macquarrie, Peter Price, John Rafelt
  • Publication number: 20030171622
    Abstract: The invention relates to a method for producing &agr;-dicarbonyl compounds of formula (I), wherein R1 and R2, independently of each other, mean C1-6-alkyl. Said method is characterised in that an &agr;,&bgr;-unsaturated ketone of formula (II), wherein R1 and R2 have the meaning above and R3 and R4, independently of each other, mean hydrogen, C1-6-alkyl or di-C1-6-alkylamino, is reacted with ozone and the resulting ozonide is treated reductively.
    Type: Application
    Filed: November 19, 2002
    Publication date: September 11, 2003
    Inventors: Uta Glufke, Paul Hanselmann
  • Patent number: 6482989
    Abstract: A method for oxidizing an alkane, comprising the step of oxidizing said alkane with oxygen in the presence of an aldehyde, a copper-based catalyst and a nitrogen-containing compound. This method may be used to convert alkanes to corresponding alcohols and ketone having pharmaceutical activities, etc.
    Type: Grant
    Filed: July 18, 2001
    Date of Patent: November 19, 2002
    Assignee: Osaka University
    Inventors: Shun-ichi Murahashi, Naruyoshi Komiya, Yukiko Hayashi
  • Patent number: 6468487
    Abstract: In the presence of an imide compound (e.g., N-hydroxyphthalimide) shown by the following formula (1): wherein R1 and R2 represent a hydrogen atom, a halogen atom, an alkyl group, an aryl group and a cycloalkyl group, and R1 and R2 may bond together to form a double bond, or an aromatic or non-aromatic ring, and Y is an O or OH, and n denotes 1 to 3; a substrate is allowed to contact with at least one reactant selected from (i) a nitrogen oxide and (ii) a mixture of carbon monoxide and oxygen to be introduced with at least one functional group selected from a nitro group and a carboxyl group. The nitrogen oxide includes, for example, a compound represented by the formula NxOy (e.g., N2O3, NO2). The substrate includes, for example, a compound having a methine carbon atom (e.g., adamantane), a compound having a methyl group or a methylene group at an adjacent moiety of an aromatic ring.
    Type: Grant
    Filed: February 19, 1999
    Date of Patent: October 22, 2002
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yasutaka Ishii, Tatsuya Nakano, Satoshi Sakaguchi
  • Patent number: 6462239
    Abstract: In the presence of (1) an oxidation catalyst comprising a crystalline complex of manganese with an N,N′-disalicylidenediamine (e.g. N,N′-disalicylidene C2-8 alkylenediamines and N,N′-disalicylidene C6-12 arylenediamines), or (2) an oxidation catalyst comprising the above complex and a basic nitrogen-containing compound, a substrate (e.g., &bgr;-isophorone or a derivative thereof) is oxidized with molecular oxygen to produce a corresponding oxide (e.g., ketoisophorone). Ketoisophorone can be obtained from &bgr;-isophorone with high conversion and high selectivity.
    Type: Grant
    Filed: April 11, 2001
    Date of Patent: October 8, 2002
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Ikuo Takahashi, Hikaru Shibata
  • Patent number: 6433229
    Abstract: Preparation of cyclic, &agr;,&bgr;-unsaturated ketones of formula II by dehydrogenation of cyclic ketones which conform to formula I in which n denotes an integer from 1 to 10, and which may be substituted, at elevated temperature in the presence of catalysts in the vapor phase, wherein the reaction is carried out in the absence of oxygen or in the presence of less than 0.5 mol of oxygen per mol of compound I at temperatures ranging from 250° to 600° C. and using catalysts having a surface area (BET) of more than 0.5 m2/g.
    Type: Grant
    Filed: September 5, 2001
    Date of Patent: August 13, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fischer, Rolf Pinkos
  • Patent number: 6410797
    Abstract: In the presence of an oxidizing catalyst, a &bgr;-isophorone derivative of the following formula (1) is oxidized in a solvent substantially from acid components (organic carboxylic acids) to form a ketoisophorone derivative of the following formula (2). The amount of the acid component in the solvent is 0 to 4,000 ppm (weight basis). The oxidizing catalyst is a complex salt of a transition metal and an N,N′-disalicylidenediamine. In the reaction, a cyclic base may further be employed as a co-catalyst. The solvent separated from the reaction mixture may be recycled to the oxidation reaction after removal of the acid component contained therein.
    Type: Grant
    Filed: August 28, 2000
    Date of Patent: June 25, 2002
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Tomohide Ina, Hiroyuki Miura, Ikuo Takahashi
  • Publication number: 20020055657
    Abstract: &bgr;-isophorone is formed by isomerizing &agr;-isophorone in the presence of an isomerizing catalyst (an aliphatic C5-20 polycarboxylic acid) in an isomerizing-reaction unit 1. The &bgr;-isophorone thus formed is oxidized with oxygen in an inert solvent in the presence of an oxidizing catalyst (a complex salt of a transition metal and an N,N′-disalicylidenediamine) in an oxidizing-reaction unit 2, thereby forming ketoisophorone. After removing a low-boiling point component, which is an impurity (non-conjugated cyclic ketone), from the reaction mixture using a distilling unit 3, a high-boiling component (oxidizing catalyst) is separated in a distilling unit 4, and then ketoisophorone is separated from the solvent in the separation unit 5. Thereafter, the solvent containing 0 to 5,000 ppm (weight basis) of the impurities and substantially free from ketoisophorone is recycled to the oxidizing reaction through a recycling line 6.
    Type: Application
    Filed: December 28, 2001
    Publication date: May 9, 2002
    Applicant: Daicel Chemical Industries,Ltd.
    Inventors: Tomohide Ina, Noboru Kamei, Hiroyuki Miura
  • Patent number: 6346651
    Abstract: &bgr;-isophorone is formed by isomerizing &agr;-isophorone in the presence of an isomerizing catalyst (an aliphatic C5-20 polycarboxylic acid) in an isomerizing-reaction unit 1. The &bgr;-isophorone thus formed is oxidized with oxygen in an inert solvent in the presence of an oxidizing catalyst (a complex salt of a transition metal and an N,N′-disalicylidenediamine) in an oxidizing-reaction unit 2, thereby forming ketoisophorone. After removing a low-boiling point component, which is an impurity (non-conjugated cyclic ketone), from the reaction mixture using a distilling unit 3, a high-boiling component (oxidizing catalyst) is separated in a distilling unit 4, and then ketoisophorone is separated from the solvent in the separation unit 5. Thereafter, the solvent containing 0 to 5,000 ppm (weight basis) of the impurities and substantially free from ketoisophorone is recycled to the oxidizing reaction through a recycling line 6.
    Type: Grant
    Filed: January 14, 2000
    Date of Patent: February 12, 2002
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Tomohide Ina, Noboru Kamei, Hiroyuki Miura
  • Patent number: 6316676
    Abstract: The process for the preparation of carbonyl compounds of the formula I where R1 and R2 are a hydrocarbon radical, or R1 and R2 together are an unsubstituted or substituted alkylene group, and X is ═O or two alkoxy groups, comprises oxidizing alcohols of the formula II  where R1 to R2 and X are as defined above, with oxygen in the gaseous phase a) at temperatures of from 270 to 600° C. on silver coated catalysts which comprise an abrasion-resistant coating of metallic silver on a core of inert support material, or b) at temperatures of from 450 to 750° C. on silver crystals and/or copper crystals having a particle size of from 0.1 to 2.5 mm for a residence time of at most 0.1 second. Also claimed is an advantageous overall process for the preparation of &agr;-diketones, preferably diacetal, from the corresponding ketone, in particular methyl ethyl ketone, via the carbonyl compounds of the formula I where X is two alkoxy groups.
    Type: Grant
    Filed: February 28, 2001
    Date of Patent: November 13, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Werner Aquila, Jörg Botzem, Melanie Brunner, Hartwig Fuchs, Wolfgang Krause, Klaus Pandl, Ulrich Schäfer-Lüderssen
  • Patent number: 6300521
    Abstract: The present invention relates to a process for preparing 3,5, 5-trimethylcyclohex -2-ene-1,4-dione (oxoisophorone; OIP) by oxidation of 3,5,5-trimethylcyclohex-3-en-1-one (&bgr;-isophorone, &bgr;-IP) with molecular oxygen in the presence of a solvent, of a base and of a manganese salen derivative as catalyst.
    Type: Grant
    Filed: June 21, 2000
    Date of Patent: October 9, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Martin Jochen Klatt, Thomas Müller, Bernhard Bockstiegel
  • Patent number: 6297404
    Abstract: The present invention relates to a process for preparing 3,5,5-trimethylcyclohex-2-ene-1,4-dione (oxoisophorone; OIP) by oxidation of 3,5,5-trimethylcyclohex-3-en-1-one (&bgr;-isophorone, &bgr;-IP) with molecular oxygen in the presence of a solvent, of a base and of a transition metal salen derivative as catalyst and of an additive.
    Type: Grant
    Filed: June 21, 2000
    Date of Patent: October 2, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Martin Jochen Klatt, Thomas Müller, Bernhard Bockstiegel
  • Patent number: 6255509
    Abstract: In the presence of (1) an oxidation catalyst comprising a crystalline complex of manganese with an N,N′-disalicylidenediamine (e.g., N,N′-disalicylidene C2-8 alkylenediamines and N,N′-disalicylidene C6-12 arylenediamines), or (2) an oxidation catalyst comprising the above complex and a basic nitrogen-containing compound, a substrate (e.g., &bgr;-isophorone or a derivative thereof) is oxidized with molecular oxygen to produce a corresponding oxide (e.g., ketoisophorone). Ketoisophorone can be obtained from &bgr;-isophorone with high conversion and high selectivity.
    Type: Grant
    Filed: June 1, 1999
    Date of Patent: July 3, 2001
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Ikuo Takahashi, Hikaru Shibata
  • Patent number: 6242653
    Abstract: The process for the preparation of carbonyl compounds of the formula I where R1 and R2 are a hydrocarbon radical, or R1 and R2 together are an unsubstituted or substituted alkylene group, and X is=O or two alkoxy groups, comprises oxidizing alcohols of the formula II where R1 to R2 and X are as defined above, with oxygen in the gaseous phase a) at temperatures of from 270 to 600° C. on silver coated catalysts which comprise an abrasion-resistant coating of metallic silver on a core of inert support material, or b) at temperatures of from 450 to 750° C. on silver crystals and/or copper crystals having a particle size of from 0.1 to 2.5 mm for a residence time of at most 0.1 second. Also claimed is an advantageous overall process for the preparation of &agr;-diketones, preferably diacetal, from the corresponding ketone, in particular methyl ethyl ketone, via the carbonyl compounds of the formula I where X is two alkoxy groups.
    Type: Grant
    Filed: August 19, 1999
    Date of Patent: June 5, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Werner Aquila, Jörg Botzem, Melanie Brunner, Hartwig Fuchs, Wolfgang Krause, Klaus Pandl, Ulrich Schäfer-Lüderssen
  • Patent number: 6229050
    Abstract: The invented process produces a corresponding 5-hydroxy-2-adamantanone derivative by allowing a 2-adamantanone derivative of the following formula (1): wherein each of Ra, Rb, and Rc is, identical to or different from one another, a hydrogen atom, a halogen atom, an alkyl group, a hydroxyl group which may be protected by a protective group, a hydroxymethyl group which may be protected by a protective group, an amino group which may be protected by a protective group, a carboxyl group which may be protected by a protective group, or a nitro group, and of carbon atoms constituting an adamantane skeleton, the other carbon atoms than carbon atoms at bridgehead positions and at a bonding position of an oxo group may have a substituent, to react with oxygen in the presence of N-hydroxyphthalimide or another imide compound, a vanadium compound, and a manganese compound.
    Type: Grant
    Filed: September 29, 2000
    Date of Patent: May 8, 2001
    Assignee: Daicel Chemical Industries, Ltd.
    Inventor: Tatsuya Nakano
  • Patent number: 6166261
    Abstract: In the presence of a catalytic system comprising a cyclic base and a complex of a transition metal with an N,N'-disalicylidenediamine, ketoisophorone or a derivative thereof is produced by oxidizing .beta.-isophorone or a derivative thereof with molecular oxygen with controlling the water content of a reaction system to 1% by weight or less at the initial stage of the reaction. Moreover, the above catalytic system further comprises a basic nitrogen-containing compound. The complex may be an N,N'-disalicylidene C.sub.2-5 alkylenediamine complex with manganese, iron, cobalt, copper, or vanadium. The cyclic base may be an alicyclic or aromtaic compound having at least two nitrogen atoms. As the basic nitrogen-containing compound, a Schiff base such as an imino compound and an anil compound can be used. The proportion of the nitrogen-containing compound to the complex is about 0.1/1 to 20/1 (molar ratio).
    Type: Grant
    Filed: May 21, 1999
    Date of Patent: December 26, 2000
    Assignee: Daicel Chemical Industries, Ltd.
    Inventor: Ikuo Takahashi
  • Patent number: 5892123
    Abstract: A method is disclosed for catalytically decomposing cyclododecyl hydroperoxide into cyclododecanone and cyclododecanol using a chromium catalyst.
    Type: Grant
    Filed: February 3, 1998
    Date of Patent: April 6, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Howard Wayne Anderson, James Bernard Sieja
  • Patent number: 5874632
    Abstract: An improved method of producing 3,5,5-trimethylcyclohex-2-ene-1,4-dione (KIP) by the oxidation of 3,5,5-trimethylcyclohex-3-ene-1-one (.beta.-IP) in the presence of managansalene-like catalysts and certain catalytic additives. ##STR1## KIP is an important intermediary product in the synthesis of trimethylhydroquinone, an initial substance in the synthesis of vitamin E. Furthermore, KIP is an initial compound for the synthesis of various carotinoids.
    Type: Grant
    Filed: May 15, 1997
    Date of Patent: February 23, 1999
    Assignee: Degussa Aktiengesellschaft
    Inventors: Rainer Hahn, Ulrich Gora, Klaus Huthmacher, Frank Hubner, Steffen Krill
  • Patent number: 5847226
    Abstract: A method for preparing nootkatone, nootkatol or mixtures thereof by oxidizing valencene, wherein the valencene is exposed to an oxygenated atmosphere in a suitable reaction medium and in the presence of an unsaturated fatty acid hydroperoxide, and the nootkatone and/or nootkatol is (are) optionally separated from the reaction medium. The method enables nootkatone yields of around 60 g per kg of reaction medium to be achieved.
    Type: Grant
    Filed: August 6, 1997
    Date of Patent: December 8, 1998
    Assignee: Firmenich SA
    Inventors: Bernard Muller, Christopher Dean, Christian Schmidt, Jean-Charles Kuhn
  • Patent number: 5773635
    Abstract: A process for preparing polyenecarbonyl compounds having a high all-E content and their acetals or ketals by aldol condensation or Horner-Emmons reaction comprises carrying out the reaction, for the purposes of the preferred formation of a double bond of E configuration and in order to maintain the E configuration of the double bonds in the stating compounds as completely as possible, in the presence of oxygen or an oxygen-inert gas mixture or nitric oxide or a nitric oxide-inert gas mixture and/or in the presence of specific stable radicals and/or in the presence of quinones or quinone derivatives.
    Type: Grant
    Filed: July 6, 1995
    Date of Patent: June 30, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter Dobler, Wolfgang Krause, Joachim Paust, Otto Worz, Udo Rheude, Wolfram Burst, Gunter Dauwel, Armin Bertram, Bernhard Schulz, Gunter Wegner, Peter Munster, Hansgeorg Ernst, Arno Kochner, Heinz Etzrodt
  • Patent number: 5030739
    Abstract: The invention is directed to a process for the catalytic oxidation of an isoprenoid containing at least one allylic hydrogen atom, which process comprises reacting the isoprenoid with oxygen or an oxygen-containing gas in an inert solvent in the presence of a N-hydroxydicarboxylic acid imide of the formula ##STR1## wherein A-B stands for CH.sub.2 -CH.sub.2, CH.dbd.CH, an aromatic hydrocarbon residue or a group derived from one of these groups in which one or more hydrogen atoms is/are replaced by alkyl or halogen,to produce a primary of secondary hydroperoxide.The process of the invention is suitable for the manufacture of steroids, vitamins, odorant substances, carotinoids and the like.
    Type: Grant
    Filed: August 31, 1990
    Date of Patent: July 9, 1991
    Assignee: Hoffman-La Roche Inc.
    Inventors: Joseph Foricher, Claude Furbringer, Karlheinz Pfoertner
  • Patent number: 4970347
    Abstract: A method of producing 2,6,6-trimethyl-2-cyclohexene-1,4-dione. Cu(II)acetylacetonate is used as a catalyst, with a suitable amount of pyridine, in the absence of solvents. The product may be used as an intermediate product for producing flavors and fragrances, or for producing vitamin E and vitamin A.
    Type: Grant
    Filed: November 13, 1989
    Date of Patent: November 13, 1990
    Assignee: Huels Aktiengesellschaft
    Inventor: Hans Bellut
  • Patent number: 4898985
    Abstract: 3,5,5-Trimethylcyclohexa-2-en-1,4-diones is prepared by oxidizing 3,5,5-trimethylcyclohexa-3-en-one with molecular oxygen or a molecular oxygen-containing gas in the presence of an organic base and an organometallic complex catalyst comprising manganese, iron, cobalt or copper atom and at least four nitrogen atoms coordination-bonded thereto.
    Type: Grant
    Filed: October 6, 1988
    Date of Patent: February 6, 1990
    Assignee: Soda Aromatic Company, Limited
    Inventors: Nobuhiko Ito, Kimio Kinoshita, Kiyonori Suzuki, Takeaki Eto
  • Patent number: 4644084
    Abstract: Tetrahydroisohumulones are prepared from beta-acids without using objectionable organic solvents by treating the beta-acids to form desoxytetrahydrohumulones which are dissolved in an aqueous alcoholic caustic solution and then oxidized and isomerized with an oxygen-containing gas in the presence of metallic ion to form the desired tetrahydroisohumulones.
    Type: Grant
    Filed: February 3, 1986
    Date of Patent: February 17, 1987
    Assignee: Miller Brewing Company
    Inventors: John M. Cowles, Henry Goldstein, Etzer Chicoye, Patrick L. Ting
  • Patent number: 4590296
    Abstract: Beta-acids are separated from alpha-acids in a hop extract without using organic solvents by bubbling CO.sub.2 through an aqueous hop extract having a pH of about 9.6 to about 13 to lower the pH to about 8.5 to about 9.5 to precipitate the beta-acids and leave the alpha-acids in the extract.
    Type: Grant
    Filed: January 25, 1984
    Date of Patent: May 20, 1986
    Assignee: Miller Brewing Company
    Inventors: John M. Cowles, Henry Goldstein, Etzer Chicoye, Patrick L. Ting
  • Patent number: 4510321
    Abstract: Processes for the autoxidative cleavage of selected ketones such as C.sub.4 -C.sub.10 cycloalkanones having at least one hydrogen or at least one R group on a carbon alpha to the carbonyl carbon or aryl alkyl ketones having the formula III ##STR1## comprising contacting a liquid phase comprising said ketone with elemental oxygen gas, preferably air, in the presence of a pulverized alkali metal hydroxide at a temperature of no more than 50.degree. C. for a time sufficient to produce an oxidized product are disclosed. Preferred cycloalkanones, 2-alkyl- and 2-arylcyclohexanone are autoxidized in pulverized sodium hydroxide/dimethoxyethane to produce 6-alkyl- or 6-aryl-6-oxohexanoic acids, respectively.
    Type: Grant
    Filed: January 31, 1983
    Date of Patent: April 9, 1985
    Assignee: Allied Corporation
    Inventors: Divakaran Masilamani, Edward H. Manahan
  • Patent number: 4393243
    Abstract: A process for synthesizing 3,5,5-trimethyl-4-[(E)-3-oxo-1-butenyl]-2-cyclohexen-1-one which is a known intermediate in a process for preparing a carotenoid.
    Type: Grant
    Filed: March 17, 1981
    Date of Patent: July 12, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Bruno Lohri
  • Patent number: 4340763
    Abstract: The process for producing hulupones by oxidation of lupulones, using an oxygen-containing gas, in a substantially aqueous, alkaline reaction medium is improved by carrying out the reaction using conditions under which the hulupones precipitate from the reaction medium as a salt, and are then recovered from the reaction medium as a salt. Hulupones are known substances which can be used as bittering agents, particularly in the brewing industry.
    Type: Grant
    Filed: April 3, 1981
    Date of Patent: July 20, 1982
    Assignee: Pfizer Inc.
    Inventor: Michael T. Wuesthoff
  • Patent number: 4267376
    Abstract: A compound having the general formula ##STR1## wherein R.sup.1 is a lower alkyl group, R.sup.2 is hydrogen or a lower alkyl group and Y is a protected hydroxyl group, for example, (.+-.)-3.beta.-tert.butoxy-2,3,3a,4,5,7,8,9,9a.beta.,9b.alpha.-decahydro-3 a.beta.-methyl-6-(3-butenyl)-1H-benz(e)inden-7-one, which is an intermediate for steroids, is prepared by dehydrative cyclization of a compound of the general formula ##STR2## wherein the symbols of R.sup.1, Y and R.sup.2 are same as defined above.
    Type: Grant
    Filed: August 30, 1979
    Date of Patent: May 12, 1981
    Assignee: Takeda Chemical Industries, Ltd.
    Inventor: Jiro Tsuji