Oxidation Of Organic Compound Utilizing Gaseous Oxygen Patents (Class 568/320)
  • Patent number: 8981159
    Abstract: The invention relates to a method for the oxidation of a primary or secondary alcohol, preferably to form an aldehyde or ketone, comprising the following steps: a) providing a catalyst composition comprising at least one compound containing a nitroxyl radical, at least one NO source, at least one carbon or mineral acid or an anhydride of a carbon or mineral acid; b) producing a reaction mixture by adding at least one primary or secondary alcohol and a gas comprising oxygen and optionally one or more than one solvent to the catalyst composition from step a) or step e); c) incubating the reaction mixture from step b) at a temperature of between 0 and 100° C. or at the boiling point of the solvent; d) simultaneously with or subsequent to step c): crystallizing the reaction product; and e) recovering the catalyst composition by removing the crystallized reaction product from the reaction mixture obtained in step d).
    Type: Grant
    Filed: December 6, 2011
    Date of Patent: March 17, 2015
    Assignee: Evonik Degussa GmbH
    Inventors: Florian Klasovsky, Thomas Haas, Thomas Tacke, Jan Christoph Pfeffer, Michael Rimbach, Michael Volland, Michiel Janssen, Roger Sheldon, Juergen Haberland
  • Patent number: 8969534
    Abstract: Described is a method to oxidize lignin or lignin sub-units. The method includes oxidation of secondary benzylic alcohol in the lignin or lignin sub-unit to a corresponding ketone in the presence of unprotected primarily aliphatic alcohol in the lignin or lignin sub-unit. The optimal catalyst system consists of HNO3 in combination with another Brønsted acid, in the absence of a metal-containing catalyst, thereby yielding a selectively oxidized lignin or lignin sub-unit. The method may be carried out in the presence or absence of additional reagents including TEMPO and TEMPO derivatives.
    Type: Grant
    Filed: February 20, 2013
    Date of Patent: March 3, 2015
    Assignee: Wisconsin Alumni Research Foundataion
    Inventors: Shannon S. Stahl, Alireza Rahimi
  • Patent number: 8748669
    Abstract: Provided is a process for producing aldehydes or ketones by oxidizing alcohols with oxygen, which comprises oxidizing alcohols to aldehydes or ketones in an organic solvent at room temperature with oxygen or air as an oxidant, wherein ferric nitrate (Fe(NO3)3.9H2O), 2,2,6,6-tetramethylpiperidine N-oxyl (TEMPO) and an inorganic chloride are used as catalysts, the reaction time is 1-24 hours, and the molar ratio of said alcohols, 2,2,6,6-tetramethylpiperidine N-oxyl and the inorganic chloride is 100:1˜10:1˜10:1˜10. The present process has the advantages of high yield, mild reaction conditions, simple operation, convenient separation and purification, recoverable solvents, substrates used therefor being various and no pollution, and therefore it is adaptable to industrialization.
    Type: Grant
    Filed: July 30, 2010
    Date of Patent: June 10, 2014
    Assignees: East China Normal University, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
    Inventors: Shengming Ma, Jinxian Liu, Jinqiang Kuang, Yu Liu, Yuli Wang, Qiong Yu, Weiming Yuan, Suhua Li, Bo Chen, Jiajia Cheng, Baoqiang Wan, Juntao Ye, Shichao Yu
  • Patent number: 8664447
    Abstract: Provided is a process for effectively and efficiently oxidizing alkyl-containing molecules with the use of an oxygen-containing gas. An iridium metal catalyst complex with the iridium being coordinated with the nitrogen atoms of a benzimidazolyl-containing ligand is used as the catalyst. The process generates alcohols, ketones and aldehydes directly from alkyl-containing molecules and/or aromatic molecules.
    Type: Grant
    Filed: September 12, 2012
    Date of Patent: March 4, 2014
    Assignee: Rutgers, The State University of New Jersey
    Inventors: Alan Stuart Goldman, Robert Timothy Stibrany
  • Publication number: 20130316938
    Abstract: Provided is class of compounds of formula (I) wherein X, R1, R2 and R3 have the same meaning as given in the specification capable of releasing fragrant compounds in a controlled manner into the surroundings.
    Type: Application
    Filed: December 23, 2011
    Publication date: November 28, 2013
    Applicant: GIVAUDAN S.A.
    Inventors: Corinne Baumgartner, Felix Flachsmann, Philip Kraft
  • Publication number: 20130245324
    Abstract: Provided is a process for effectively and efficiently oxidizing alkyl-containing molecules with the use of an oxygen-containing gas. An iridium metal catalyst complex with the iridium being coordinated with the nitrogen atoms of a benzimidazolyl-containing ligand is used as the catalyst. The process generates alcohols, ketones and aldehydes directly from alkyl-containing molecules and/or aromatic molecules.
    Type: Application
    Filed: September 12, 2012
    Publication date: September 19, 2013
    Inventors: Alan Stuart Goldman, Robert Timothy Stibrany
  • Patent number: 8519132
    Abstract: The invention concerns processes for oxidizing an alcohol to produce a carbonyl compound. The processes comprise contacting the alcohol with (i) a gaseous mixture comprising oxygen; and (ii) an amine compound in the presence of a catalyst, having the formula: where each of R1-R12 are independently H, alkyl, aryl, CF3, halogen, OR13, SO3R14, C(O)R15, CONR16R17 or CO2R18; each of R13-R18 is independently alkyl or aryl; and Z is alkl or aryl.
    Type: Grant
    Filed: March 8, 2012
    Date of Patent: August 27, 2013
    Assignee: Los Alamos National Security, LLC
    Inventors: Susan Kloek Hanson, Louis A. Silks, Ruilian Wu
  • 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
  • Publication number: 20120232279
    Abstract: The invention concerns processes for oxidizing an alcohol to produce a carbonyl compound. The processes comprise contacting the alcohol with (i) a gaseous mixture comprising oxygen; and (ii) an amine compound in the presence of a catalyst, having the formula: where each of R1-R12 are independently H, alkyl, aryl, CF3, halogen, OR13, SO3R14, C(O)R15, CONR16R17 or CO2R18; each of R13-R18 is independently alkyl or aryl; and Z is alkl or aryl.
    Type: Application
    Filed: March 8, 2012
    Publication date: September 13, 2012
    Applicant: LOS ALAMOS NATIONAL SECURITY, LLC
    Inventors: Susan Kloek Hanson, Louis A. Silks, Ruilian Wu
  • Publication number: 20120220792
    Abstract: Provided is a process for producing aldehydes or ketones by oxidizing alcohols with oxygen, which comprises oxidizing alcohols to aldehydes or ketones in an organic solvent at room temperature with oxygen or air as an oxidant, wherein ferric nitrate (Fe(NO3)3.9H2O), 2,2,6,6-tetramethylpiperidine N-oxyl (TEMPO) and an inorganic chloride are used as catalysts, the reaction time is 1-24 hours, and the molar ratio of said alcohols, 2,2,6,6-tetramethylpiperidine N-oxyl and the inorganic chloride is 100:1˜10:1˜10:1˜10. The present process has the advantages of high yield, mild reaction conditions, simple operation, convenient separation and purification, recoverable solvents, substrates used therefor being various and no pollution, and therefore it is adaptable to industrialization.
    Type: Application
    Filed: July 30, 2010
    Publication date: August 30, 2012
    Inventors: Shengming Ma, Jinxian Liu, Jinqiang Kuang, Yu Liu, Yuli Wang, Qiong Yu, Weiming Yuan, Suhua Li, Bo Chen, Jiajia Cheng, Baoqiang Wan, Juntao Ye, Shichao Yu
  • 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
  • Publication number: 20120035308
    Abstract: Mono- or diester plasticizers of the formula: wherein A is either —OC(O)R? or ?O, and X is either —COC(O)R or —C(O)OR, and R and R? are C3 to C13 alkyl, which are the same or different, formed from cyclohexylbenzene and processes of making them.
    Type: Application
    Filed: August 3, 2011
    Publication date: February 9, 2012
    Applicant: EXXONMOBIL RESEARCH AND ENGINEERING COMPANY
    Inventors: Kun Wang, Jihad Mohammed Dakka, Edmund John Mozeleski, Francisco Manuel Benitez, Lisa Saunders Baugh, Allen David Godwin, Diana S. Smirnova, Stephen Zushma
  • 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
  • Patent number: 7683232
    Abstract: A process is disclosed for producing functionalized olefins from a fuel source including an organic compound including a functional group. Useful fuel sources include, for example, biofeedstocks (e.g., carbohydrates, triglycerides, polyols, and biodiesel). The process is preferably carried out by partial oxidation. The overall process can be carried out autothermally.
    Type: Grant
    Filed: May 25, 2005
    Date of Patent: March 23, 2010
    Assignee: Regents of the University of Minnesota
    Inventors: Lanny D. Schmidt, Ramanathan Subramanian
  • Patent number: 7645907
    Abstract: This invention relates to a Polyoxometalate (POM) represented by the formula: (An)m+[HqM16X8W48O184(OH)32]m? or solvates thereof, wherein: A represents a cation, n is the number of the cations A, m is the charge of the polyoxoanion, q is the number of protons and varies from 0 to 12, M represents a transition metal, and X represents a heteroatom selected from P, As and mixtures thereof. This invention also relates to a process to produce such POMs and to a process for the homogeneous or heterogeneous oxidation of organic substrates comprising contacting the organic substrate with such POMs.
    Type: Grant
    Filed: March 23, 2007
    Date of Patent: January 12, 2010
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Ulrich Kortz, Sib Sankar Mal
  • Patent number: 7453013
    Abstract: The invention relates to a catalytic method for the production of aliphatic and aromatic carbonyl compounds with at least one aldehyde or ketone function, whereby said compounds can also comprise at least one aldehyde and ketone function. A starting material comprising at least one aliphatic- and/or aromatic-bonded functional group of formula (I), where R1?H, alkyl or aryl, X?H, or a group which may be substituted by the sulphinyl group of a sulphoxide during the catalytic reaction, n=a whole number from 1 to 8, is oxidised in the presence of a sulphoxide and/or a sulphide and the presence of iron salts or redox pairs of iron/copper or silver/copper salts, by means of an oxidising agent with a redox potential of E0>+2 V vs. NHE, whereby the sulphoxide or sulphide has a catalytic function.
    Type: Grant
    Filed: September 11, 2007
    Date of Patent: November 18, 2008
    Assignee: Weylchem Frankfurt GmbH
    Inventors: Franco Antognoli, Paul Rys
  • Patent number: 7351867
    Abstract: The present invention relates to a process of oxidation of alcohols selectively to aldehydes or ketones with molecular oxygen using a TEMPO based catalyst, Fe-bipyridyl or Fe-phenantroline co-catalyst and N-bromosuccinimide promoter in acetic acid solvent. The oxidation takes places at high rates and high aldehyde selectivity at temperatures in the range 45-50° C. and oxygen or air pressures of 0-15 psi. The alcohol conversion of 95-100% and aldehyde selectivity higher than 95% are achieved over 3-4 hours reaction time. Aldehydes such as 3,3-dimethyl-1-butanal can be produced efficiently using the present invention.
    Type: Grant
    Filed: February 24, 2005
    Date of Patent: April 1, 2008
    Assignee: The NutraSweet Company
    Inventors: Setrak K. Tanielyan, Robert L. Augustine, Indra Prakash, Kenneth E. Furlong, Handley E. Jackson
  • Patent number: 7273954
    Abstract: The invention relates to a catalytic method for the production of aliphatic and aromatic carbonyl compounds with at least one aldehyde or ketone function, whereby said compounds can also comprise at least one aldehyde and ketone function. A starting material comprising at least one aliphatic- and/or aromatic-bonded functional group of formula (I), where R1=H, alkyl or aryl, X=H, or a group which may be substituted by the sulphinyl group of a sulphoxide during the catalytic reaction, n=a whole number from 1 to 8, is oxidised in the presence of a sulphoxide and/or a sulphide and the presence of iron salts or redox pairs of iron/copper or silver/copper salts, by means of an oxidising agent with a redox potential of Eo>+2 V vs. NHE, whereby the sulphoxide or sulphide has a catalytic function.
    Type: Grant
    Filed: November 14, 2003
    Date of Patent: September 25, 2007
    Assignee: Clariant Speciality Fine Chemicals (Deutschland) GmbH
    Inventors: Franco Antognoli, Paul Rys
  • Patent number: 7235699
    Abstract: The present invention relates to alkoxy-substituted indanes, their preparation and use and to the preparation and use of the corresponding alkoxy-substituted indanones.
    Type: Grant
    Filed: February 27, 2003
    Date of Patent: June 26, 2007
    Assignee: Symrise GmbH & Co. KG
    Inventor: Oskar Koch
  • Patent number: 7148384
    Abstract: The invention relates to a process for preparing fluorinated acetophenones from fluorinated aryl compounds in the presence of N-hydroxyphthalimide and the use thereof.
    Type: Grant
    Filed: June 17, 2004
    Date of Patent: December 12, 2006
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albrecht Marhold, Jens Peter Joschek
  • 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: 6946579
    Abstract: A series of aryl piperazine compounds are effective pharmaceuticals for the treatment of conditions related to or affected by the serotonin 1A receptor; the compounds are particularly effective antagonists at that receptor, and are particularly useful for alleviating the symptoms of nicotine and tobacco withdrawal.
    Type: Grant
    Filed: July 2, 2003
    Date of Patent: September 20, 2005
    Assignee: Eli Lilly and Company
    Inventors: Alexander Glenn Godfrey, Daniel Timothy Kohlman, John Cunningham O'Toole, Yao-Chang Xu, Tony Yantao Zhang
  • Patent number: 6828463
    Abstract: The present invention relates to a process for the preparation of aromatic carbonyl compound with carbonyl group attached to its aromatic ring, particularly relates to a process for the preparation of aromatic carbonyl compound with carbonyl group attached to its aromatic ring, by oxidizing with molecular oxygen the methylene or alcoholic group attached to aromatic ring of an aromatic compound, using a polyoxotnetallate(s) anion exchanged hydrotalcite catalyst.
    Type: Grant
    Filed: March 26, 2003
    Date of Patent: December 7, 2004
    Assignee: Council of Scientific and Industrial Research
    Inventors: Vasant R. Choudhary, Vijay S. Narkhede, Jayant R. Indurkar
  • Patent number: 6790997
    Abstract: The invention relates to a process for the preparation of carbonyl compounds by the oxidation of alcohols in the presence of osmium compounds as catalysts in water or a solvent mixture containing water.
    Type: Grant
    Filed: July 23, 2002
    Date of Patent: September 14, 2004
    Assignee: Bayer Aktiengesellschaft
    Inventors: Markus Eckert, Hans-Christian Militzer, Matthias Beller, Christian Döbler, Gerald Mehltretter, Uta Sundermeier
  • Patent number: 6680385
    Abstract: A method for the preparation of aryl methyl ketones converts a variety of ethyl arenas to the corresponding aryl methyl ketones using a dioxygen-containing gas as the oxidant. The catalyst used for the reaction is a metal complex bearing general formulas as disclosed.
    Type: Grant
    Filed: January 25, 2002
    Date of Patent: January 20, 2004
    Assignees: The Hong Kong Polytechnic University, Sichuan University
    Inventors: Albert Sun-Chi Chan, Jian-Ying Qi, Cheng-Chao Pai, Xian-Jun Li, Li-Sheng Deng, Wen-Zao Li, Bin Sun, Jia-Yuan Hu
  • Patent number: 6670509
    Abstract: A process for oxygenating organic substrates such as aliphatic hydrocarbons has been developed. The process involves contacting the organic substrate with oxygen in the presence of a bicyclo imide promoter and a metal co-catalyst. The process is preferably carried out using sulfolane as the solvent. Optionally, the oxygenated product can be hydrogenated to give the corresponding alcohol which can optionally in turn be dehydrated to provide the corresponding olefin.
    Type: Grant
    Filed: April 11, 2002
    Date of Patent: December 30, 2003
    Assignee: UOP LLC
    Inventors: Paul R. Kurek, David W. House
  • Publication number: 20030166682
    Abstract: An improved process for the manufacture of fexofenadine is described in which a compound of formula (F): wherein R2 represents COOH, COO—C1-6 alkyl or CN; and R3 represents hydrogen, mesylate, triflate, tosylate or carboxy-C1-6-alkyl, or a salt thereof is prepared by: (I) reacting a compound of formula (B): wherein R1 represents hydrogen or carboxy-C1-6-alkyl; and R2 is a hereinbefore defined, with a copper and/or silver compound in the presence of palladium or a compound thereof to yield a compound of formula (C): wherein R1, and R2 are as hereinbefore defined; (II) converting said compound of formula (C) into a compound of formula (E): wherein R2 and R3 are as hereinbefore defined and R4 represents a halogen atom, and (III) reacting said compound of formula (E) with azacyclonol.
    Type: Application
    Filed: March 19, 2003
    Publication date: September 4, 2003
    Inventor: Federico Junquera Milla
  • Publication number: 20030144554
    Abstract: A method for the preparation of aryl methyl ketones converts a variety of ethyl arenas to the corresponding aryl methyl ketones using a dioxygen-containing gas as the oxidant. The catalyst used for the reaction is a metal complex bearing general formulas as disclosed.
    Type: Application
    Filed: January 25, 2002
    Publication date: July 31, 2003
    Applicant: The Hong Kong Polytechnic University
    Inventors: Albert Sun-Chi Chan, Jian-Ying Qi, Cheng-Chao Pai, Xian-Jun Li, Li-Sheng Deng, Wen-Zao Li, Bin Sun, Jia-Yuan Hu
  • Patent number: 6486357
    Abstract: A method of oxidizing an organic alcohol, wherein the organic alcohol is contacted with a stoichiometric excess of oxygen in the presence of an effective catalytic amount of a maganese-containing octahedral molecular sieve or octahedral layer. Primary alcohols are selectively oxidized to aldehydes, and secondary alcohols are selectively oxidized to ketones.
    Type: Grant
    Filed: August 14, 2001
    Date of Patent: November 26, 2002
    Assignee: The University of Connecticut
    Inventors: Steven L. Suib, Young Chan Son, Amy R. Howell
  • Patent number: 6479705
    Abstract: A process for preparing a ketone, an alcohol and/or a hydroperoxide is provided by reacting a hydrocarbon with molecular oxygen in the presence of a cyclic N-hydroxyimide and a compound of a transition metal, in which an oxygen-containing gas is supplied in a reaction system and at the same time a gas containing 1 to-about 8.59, by volume of oxygen is discharged from the reaction system. This process is excellent in productivity and safety and produces the desired products at a high selectivity.
    Type: Grant
    Filed: December 14, 2000
    Date of Patent: November 12, 2002
    Assignees: Sumitomo Chemical Company, Limited, Daicel Chemical Industries, Ltd.
    Inventors: Shuzo Murata, Nobuhiro Tani, Hiroyuki Asano
  • Patent number: 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: 20020045778
    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: Application
    Filed: July 18, 2001
    Publication date: April 18, 2002
    Inventors: Shun-Ichi Murahashi, Naruyoshi Komiya, Yukiko Hayashi
  • Patent number: 6350916
    Abstract: Alcohols are oxidized to their corresponding ketone or aldehyde using an aryl chloride oxidant and a metal-ligand complex or metal/ligand composition. This reaction is particularly applicable to aromatic alcohols and cyclic and bicyclic aliphatic alcohols.
    Type: Grant
    Filed: March 21, 2000
    Date of Patent: February 26, 2002
    Assignee: Symyx Technologies, Inc.
    Inventors: Anil Guram, Xiaohong Bei
  • Patent number: 6326520
    Abstract: The invention relates to a method for producing a novel optically active compound represented by the general formula [IV]. This method includes the step of reacting a vinyl ether with a halogenated acetaldehyde in the presence of an optically active binaphthol-titanium complex. With this, the novel optically active compound can be produced very easily. Furthermore, the novel optically active compound can easily be oxidized to a novel optically active &agr;,&bgr;-dihydrexyketone represented by the general formula [V]. These novel optically active compounds can each be used as useful intermediates.
    Type: Grant
    Filed: August 20, 1999
    Date of Patent: December 4, 2001
    Assignee: Central Glass Company, Limited
    Inventors: Akihiro Ishii, Koichi Mikami
  • 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: 6297403
    Abstract: A process for the preparation of vinyl, alkynyl, aryl or heteroaryl aldehydes or vinyl, alkynyl, aryl or heteraoryl ketones includes reacting vinyl-, alkynyl-, aryl- and heteroarylmethyl and -methylene compounds with the aid of a mediator and an oxidant, wherein the mediator is selected from the group of the aliphatic, heterocyclic or aromatic NO, or NOH containing compounds.
    Type: Grant
    Filed: January 5, 2000
    Date of Patent: October 2, 2001
    Assignee: Consortium für elektrochemische Industrie GmbH
    Inventors: Elke Fritz-Langhals, Johannes Freudenreich
  • 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: 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: 6252121
    Abstract: This invention relates to a process for separating one or more cyclic products from a reaction product fluid comprising one or more cyclic reactants, a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, a non-polar solvent and said one or more cyclic products, wherein said process comprises: (1) reacting said one or more cyclic reactants in the presence of said metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand and non-polar solvent to form a multiphase reaction product fluid; and (2) separating said multiphase reaction product fluid to obtain a non-polar phase comprising said one or more cyclic reactants, metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand and non-polar solvent and a polar phase comprising said one or more cyclic products.
    Type: Grant
    Filed: July 27, 1999
    Date of Patent: June 26, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John Nicholas Argyropoulos, David Robert Bryant, Michael Leo Tulchinsky, Jeffrey Scott Kanel, Paul Foley, Barry Brent Fish
  • 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: 6169213
    Abstract: Process for the preparation of heteroaryl aldehydes or heteroaryl ketones by reaction with heteroarylmethanols with the aid of a mediator and an oxidant, wherein the mediator is selected from the group of the aliphatic, cycloaliphatic, heterocyclic or aromatic NO, and NOH containing compounds.
    Type: Grant
    Filed: January 5, 2000
    Date of Patent: January 2, 2001
    Assignee: Consortium f{umlaut over (u)}r elektrochemische Industrie GmbH
    Inventors: Elke Fritz-Langhals, Johannes Freudenreich, Norbert Hampp, Anton Candussio
  • Patent number: 6069282
    Abstract: A process for the preparation of vinyl, alkynyl or aryl aldehydes or vinyl, alkynyl or aryl ketones by reaction of vinyl-, alkynyl- or aryl- methanols with the aid of a mediator and an oxidant, wherein the mediator is selected from the group of the aliphatic, cycloaliphatic, heterocyclic or aromatic NO or NOH containing compounds.
    Type: Grant
    Filed: May 21, 1998
    Date of Patent: May 30, 2000
    Assignee: Consortium fur elektrochemische Industrie GmbH
    Inventors: Elke Fritz-Langhals, Johannes Freudenreich, Norbert Hampp, Anton Candussio
  • Patent number: 6037501
    Abstract: By subjecting an aromatic compound of the formula (I), which is an inexpensive raw material, to a vapor-phase intramolecular cyclodehydrogenation reaction, fluorenes of the formula (II) can be obtained industrially advantageously in a high yield. Fluorenes (II) are expected to be used as raw materials for heat-resistant epoxy resins, polycarbonates or polyesters. wherein R.sub.1 and R.sub.2 each represent a hydrogen atom, a methyl group or an ethyl group, or R.sub.1 and R.sub.2 represent .dbd.O at the same time; and R and R' each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.
    Type: Grant
    Filed: June 6, 1998
    Date of Patent: March 14, 2000
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Noboru Saito, Toshiya Iida, Isamu Maeda
  • Patent number: 6023000
    Abstract: A process for the preparation of vinyl, alkynyl or aryl aldehydes or vinyl, alkynyl or aryl ketones includes reacting vinyl-, alkynyl- and aryl- and -methylene compounds with the aid of a mediator and an oxidant, wherein the mediator is selected from the group of the aliphatic, heterocyclic or aromatic NO or NOH containing compounds.
    Type: Grant
    Filed: May 21, 1998
    Date of Patent: February 8, 2000
    Assignee: Consortium fur elektrochemisch Industrie GmbH
    Inventors: Elke Fritz-Langhals, Johannes Freudenreich
  • Patent number: 5990357
    Abstract: In a process for the catalytic oxidation of isoalkylaromatic hydrocarbons into ketones, alcohols and peroxides the isoalkyl- aromatic hydrocarbons in fluid phase at a temperature of 60 to 120.degree. C. are oxidized by oxygen in the presence of a catalyst of metal salt of different valency and alkylammonium salt or alkylphosphonium salt. Further there is claimed a catalyst for the oxidation of isoalkylaromatic hydrocarbons, containing a metal salt selected from copper salts, cobalt salts and manganese salts or their mixtures and an alkylammonium salt or alkylphosphonium salt in a ratio of metal salt to alkylammonium salt or alkylphosphonium salt of 0.5 to 50:1.
    Type: Grant
    Filed: March 19, 1997
    Date of Patent: November 23, 1999
    Assignee: Rutgers Kureha Solvents GmbH
    Inventors: Jan Zawadiak, Zbigniew Stec, Ulrich Knips, Robert Zellerhoff, Danuta Gilner, Beata Orlinska, Jerzy Polaczek
  • Patent number: 5912388
    Abstract: A process for preparing an aldehyde or ketone comprising reacting a primary or secondary alcohol with oxygen in the presence of a base, a catalytic amount of a copper salt and a suitable lignad under anhydrous conditions.
    Type: Grant
    Filed: November 12, 1997
    Date of Patent: June 15, 1999
    Assignee: Zeneca Limited
    Inventors: Christopher John Urch, Istvan Ettienne Marko, Masao Tuskazaki, Paul Richard Giles, Stephen Martin Brown
  • 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: 5563297
    Abstract: The present invention relates to novel intermediates for the preparation of vitamin A and carotenoids, corresponding to the following formula (I): ##STR1## in which X is a carbon atom; n is equal to 1 or 2; R.sub.1, R.sub.2 and R.sub.3, which may be identical or different, each independently represent hydrogen, alkyl containing 1 to 4 carbon atoms, alkenyl containing 2 to 11 carbon atoms or aryl, each alkyl and alkenyl may be linear, branched or cyclic, or R.sub.1 and R.sub.2 can together with the carbon atom to which they are attached form a cycloaliphatic compound which is optionally substituted; and R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8, which may be identical or different, each independently represent hydrogen, alkyl containing 1 to 4 carbon atoms or alkenyl containing 2 to 10 carbon atoms, each alkyl or alkenyl being linear, or if containing sufficient numbers of carbon atoms, may also be branched or cyclic, or an aryl containing 6 to 10 carbon atoms, or any two of R.sub.4, R.sub.5, R.sub.6, R.
    Type: Grant
    Filed: October 7, 1994
    Date of Patent: October 8, 1996
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventor: Hugues Bienayme
  • Patent number: 5453521
    Abstract: Process for producing 10-deacetylbaccatin III from the various parts of the yew (Taxus sp.) by extraction and selective crystallization from a methanolic extract of the plant mass.
    Type: Grant
    Filed: September 17, 1993
    Date of Patent: September 26, 1995
    Assignee: Rhone-Poulenc Rorer S.A.
    Inventors: Jean-Claude Gaullier, Bernadette Mandard, Rodolphe Margraff