Oxidation Of Organic Compound Utilizing Gaseous Oxygen Patents (Class 568/357)
  • Patent number: 9561991
    Abstract: This invention relates to a process for co-producing cyclohexanol and alkanol, including a cyclohexene esterification step and a cyclohexyl ester hydrogenation step. This invention further relates to a process for further producing cyclohexanone or caprolactam, starting from the co-producing process, and an apparatus for co-producing cyclohexanol and alkanol. The process for co-producing cyclohexanol and alkanol of this invention is environment-friendly, with low production cost and highly improved atom economy.
    Type: Grant
    Filed: September 17, 2013
    Date of Patent: February 7, 2017
    Assignees: CHINA PETROLEUM & CHEMICAL CORPORATION, RESEARCH INSTITUTE OF PETROLEUM PROCESSING, SINOPEC
    Inventors: Baoning Zong, Dongqiang Ma, Langyou Wen, Bin Sun, Keyong Yang
  • Patent number: 9464011
    Abstract: A process for producing an alkylated aromatic compound comprises contacting an aromatic starting material and hydrogen with a plurality of catalyst particles under hydroalkylation conditions to produce an effluent comprising the alkylated aromatic compound, the catalyst comprising a composite of a solid acid, an inorganic oxide different from the solid acid and a hydrogenation metal, wherein the distribution of the hydrogenation metal in at least 60 wt % of the catalyst particles is such that the average concentration of the hydrogenation metal in the rim portion of a given catalyst particle is Crim, the average concentration of the hydrogenation metal in the outer portion of a given catalyst particle is Couter, the average concentration of the hydrogenation metal in the center portion of the given catalyst particle is Ccenter, where Crim/Ccenter?2.0 and/or Couter/Ccenter2.0. Also disclosed are rimmed catalyst and process for making phenol and/or cyclohexanone using the catalyst.
    Type: Grant
    Filed: March 6, 2014
    Date of Patent: October 11, 2016
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Gabor Kiss, Thomas E. Green, Terry E. Helton, William C. Horn, William A. Lamberti, Tan-Jen Chen
  • Patent number: 8993819
    Abstract: The present invention provides a process for preparing cycloheptene and derivatives thereof by ring-closing metathesis of unsymmetric 1,8-dienes whose C—C double bond at the 8 position is nonterminal. Cycloheptene and the cycloheptanone, cycloheptylamine, cycloheptanecarbaldehyde, cycloheptanecarboxylic acid and cycloheptanecarbonyl chloride conversion products thereof, and the derivatives thereof, are important synthesis units for active ingredient compounds. The ring-closing metathesis is preferably performed as a reactive distillation. The unsymmetric 1,8-dienes for the ring-closing metathesis can be obtained by catalytic decarbonylation or oxidative decarboxylation from the corresponding unsaturated carboxylic acids or carboxylic acid derivatives.
    Type: Grant
    Filed: July 10, 2012
    Date of Patent: March 31, 2015
    Assignee: BASF SE
    Inventors: Joaquim Henrique Teles, Michael Limbach, Richard Dehn, Stephan Deuerlein, Manuel Danz
  • Publication number: 20130184494
    Abstract: According to the first embodiment of the present invention, an oxide of a hydrocarbon compound can be produced with high yield and high productivity by oxidizing the hydrocarbon compound with molecular oxygen in the co-presence of an N-hydroxy compound, such as methyl ethyl ketone or N-hydroxysuccinimide, and a phosphate ester, such as dibutyl phosphate. According to another embodiment of the present invention, an oxide of a hydrocarbon compound can be produced with high yield by using an oxidation catalyst that comprises an oxime compound, such as methyl ethyl ketone. According to another embodiment of the present invention, an alcohol and/or a ketone can be produced with high yield by oxidizing the hydrocarbon compound at a temperature of 160° C. or less, and by decomposing the resulting hydroperoxide, for example, in a unit having an inner surface formed by a material from which no transition metal ion is generated.
    Type: Application
    Filed: September 26, 2011
    Publication date: July 18, 2013
    Applicant: USE Industries, Ltd.
    Inventors: Kazunori Kurosawa, Joji Funatsu, Naoya Katagiri, Junichi Kugimoto
  • Publication number: 20130018205
    Abstract: The present invention provides a process for preparing cycloheptene and derivatives thereof by ring-closing metathesis of unsymmetric 1,8-dienes whose C—C double bond at the 8 position is nonterminal. Cycloheptene and the cycloheptanone, cycloheptylamine, cycloheptanecarbaldehyde, cycloheptanecarboxylic acid and cycloheptanecarbonyl chloride conversion products thereof, and the derivatives thereof, are important synthesis units for active ingredient compounds. The ring-closing metathesis is preferably performed as a reactive distillation. The unsymmetric 1,8-dienes for the ring-closing metathesis can be obtained by catalytic decarbonylation or oxidative decarboxylation from the corresponding unsaturated carboxylic acids or carboxylic acid derivatives.
    Type: Application
    Filed: July 10, 2012
    Publication date: January 17, 2013
    Applicant: BASF SE
    Inventors: Joaquim Henrique TELES, Michael Limbach, Richard Dehn, Stephan Deuerlein, Manuel Danz
  • Patent number: 8252959
    Abstract: A process for the preparation of an 1,1-disubstituted oxirane is disclosed, wherein an organic sulphide is reacted in a polar solvent with an educt containing a leaving group attached to a primary or secondary carbon atom, and/or the sulfonium salt formed in this way is reacted with a ketone in presence of a base and a polar solvent. Oxiranes of the type obtained may be further converted into the corresponding ?-hydroxyketone or ?-aminoketone, either in one step by subjecting to aerobic oxidation in the presence of a transition metal catalyst, or in two steps by hydrolyzation in the presence of an aqueous acid to the corresponding dialcohol and subsequent selective oxidation. Further described are some novel epoxide intermediates. The ?-hydroxyketones and ?-aminoketones thus obtainable are useful inter alga as photoinitiators.
    Type: Grant
    Filed: June 29, 2005
    Date of Patent: August 28, 2012
    Assignee: BASF SE
    Inventors: Nicole End, Reinhard H. Sommerlade, Yvonne Richter
  • Publication number: 20120053354
    Abstract: [Problem] There is provided a method for producing an oxygen-containing compound safely and with improved reaction efficiency, in which an undesired peroxide is unlikely to be produced, and efficient heat exchange of the ozonization can be achieved.
    Type: Application
    Filed: February 17, 2010
    Publication date: March 1, 2012
    Applicant: Utsunomiya University
    Inventor: Masaaki Yoshida
  • Patent number: 7956221
    Abstract: The present invention relates to a process for decomposing cyclohexylhydroperoxide into cyclohexanone, said process comprising mixing an organic feed solution comprising cyclohexylhydroperoxide with an aqueous base solution in the absence of a transition metal catalyst resulting in a mixture comprising (i) an aqueous phase and (ii) an organic phase comprising cyclohexanone and cyclohexanol.
    Type: Grant
    Filed: December 16, 2005
    Date of Patent: June 7, 2011
    Assignee: DSM IP Assets B.V.
    Inventor: Imre Toth
  • Patent number: 7939692
    Abstract: There are disclosed a method for producing a ketone compound, which comprises reacting an olefin compound with molecular oxygen and water in the presence of an effective amount of proton and a catalyst containing i) a chlorine-free palladium source, ii) a heteropoly acid or an acid salt of a heteropoly acid, and iii) a mesoporous silicate, and catalysts for the process.
    Type: Grant
    Filed: January 3, 2007
    Date of Patent: May 10, 2011
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Roger Gläser, Sudhir Dapurkar, Carsten Stöcker, Junichi Nishimoto, Masayoshi Murakami
  • Patent number: 7923583
    Abstract: An object of the present invention is to provide a method capable of producing a cycloalkanol and/or a cycloalkanone with a favorable selectivity coefficient by oxidizing a cycloalkane with a favorable conversion ratio. Disclosed is a method for producing a cycloalkanol and/or a cycloalkanone, which comprises oxidizing a cycloalkane with oxygen in the presence of a mesoporous silica which contains at least one transition metal and has been also subjected to contact treatment with an amine and/or ammonia. Preferably, a crystal obtained by mixing a compound containing the metal, a silicon compound, a structure-directing agent and water is subjected to contact treatment with an amine and/or ammonia and then fired to obtain a mesoporous silica, and a cycloalkane is oxidized with oxygen in the presence of the mesoporous silica.
    Type: Grant
    Filed: February 25, 2009
    Date of Patent: April 12, 2011
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masahiro Hoshino, Nobufumi Watanabe, Keisuke Sugita
  • Patent number: 7910777
    Abstract: The present invention provides a method for producing cycloalkanol and/or cycloalkanone, which comprises reacting cycloalkane with molecular oxygen in the presence of mesoporous silica, (1) the mesoporous silica containing at least one transition metal; (2) the mesoporous silica having such pore distribution that the ratio of a total pore volume of mesoporous silica particles having a pore size of 3 to 50 nm to a total pore volume of mesoporous silica particles having a pore size of 2 to 50 nm is 50% or more; and (3) the mesoporous silica being modified by an organic silicon compound.
    Type: Grant
    Filed: September 16, 2009
    Date of Patent: March 22, 2011
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masahiro Hoshino, Keisuke Sugita, Avelino Corma
  • Patent number: 7897818
    Abstract: A method of oxidizing hydrocarbons in liquid phase is provided. According to this method, a liquid-phase oxidation reaction of hydrocarbons is carried out by using an organic compound capable of chelating metals as auxiliary agent, represented by formula (II), in the presence of an oxygen-containing gas and a transition metal catalyst. Accordingly, the conversion degree of the hydrocarbon is increased, and the overall yields of products are improved while the selectivity of catalytic oxidation reaction is still high.
    Type: Grant
    Filed: July 7, 2009
    Date of Patent: March 1, 2011
    Assignee: China Petrochemical Development Corporation
    Inventors: Jui-Tsung Hung, Chin-Yi Lee, Chia-Jung Tsai
  • Publication number: 20110021841
    Abstract: In a process for producing cyclohexylbenzene, benzene and hydrogen are contacted with a catalyst under hydroalkylation conditions to produce an effluent containing cyclohexylbenzene. The catalyst comprises a composite of a molecular sieve, an inorganic oxide different from said molecular sieve and at least one hydrogenation metal, wherein at least 50 wt % of said hydrogenation metal is supported on the inorganic oxide and the inorganic oxide has an average particle size less than 40 ?m (microns).
    Type: Application
    Filed: February 23, 2009
    Publication date: January 27, 2011
    Inventors: Tan-Jen Chen, Jane C. Cheng, Francisco M. Benitez, Terry E. Helton, Jon E. Stanat
  • 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: 7834217
    Abstract: Disclosed is a method for industrially efficiently producing a corresponding useful oxidation product such as a cycloalkyl hydroperoxide, a cycloalkanol, and/or a cycloalkanone, especially a particularly useful cycloalkanone, from a cycloalkane with a high selectivity in a good yield at low cost. This method is advantageous in respect of energy and process. Specifically, an oxidation product of a cycloalkane is obtained by oxidizing the cycloalkane in a liquid-liquid two phase system using an aqueous solvent in the presence of a nitrogen atom-containing cyclic compound which contains, as its ring constituent, a structure represented by following Formula (I): wherein X represents an oxygen atom or an —OR group, and wherein R represents a hydrogen atom or a hydroxyl-protecting group, and which has a solubility in water at 25° C. of 0.5 g/100 g-H2O or more.
    Type: Grant
    Filed: November 30, 2007
    Date of Patent: November 16, 2010
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Takumi Omori, Yasushi Sato
  • Publication number: 20100191017
    Abstract: In a process for producing cyclohexylbenzene, benzene and hydrogen are contacted with a catalyst under hydroalkylation conditions to produce an effluent containing cyclohexylbenzene. The catalyst comprises a composite of a molecular sieve, an inorganic oxide different from said molecular sieve and at least one hydrogenation metal, wherein at least 50 wt % of said hydrogenation metal is supported on the inorganic oxide.
    Type: Application
    Filed: July 11, 2008
    Publication date: July 29, 2010
    Inventors: Tan-Jen Chen, John Scott Buchanan, Jane Chi-ya Cheng, Terry E. Helton
  • Patent number: 7709685
    Abstract: An object of the present invention is to provide a method capable of producing cycloalkanol and/or cycloalkanone with a favorable selectivity by oxidizing cycloalkane with a favorable conversion. A cycloalkanol and/or cycloalkanone are produced by oxidizing cycloalkane with oxygen in the presence of mesoporous silica which contains at least one metal selected from metals of Groups 5 to 10 of the Periodic Table and which is also subjected to a contact treatment with an organosilicon compound. The metal is preferably at least one metal selected from the group consisting of vanadium, chromium, manganese, iron, cobalt, ruthenium and palladium, and the mesoporous silica is preferably MCM-41 type mesoporous silica.
    Type: Grant
    Filed: March 14, 2008
    Date of Patent: May 4, 2010
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masahiro Hoshino, Tatsuya Suzuki, Hajime Ishida
  • Patent number: 7692044
    Abstract: An object of the present invention is to provide a process capable of producing cycloalkanol and/or cycloalkanone with a favorable selectivity by oxidizing cycloalkane with a favorable conversion. Disclosed is a process for producing cycloalkanol and/or cycloalkanone, which comprises oxidizing cycloalkane with oxygen in the presence of mesoporous silica, wherein (1) the mesoporous silica contains at least one transition metal, and (2) a ratio of total volume of mesoporous silica particles having a particle diameter of 20 ?m or less to total volume of entire mesoporous silica particles is 25% or more in the mesoporous silica.
    Type: Grant
    Filed: August 1, 2008
    Date of Patent: April 6, 2010
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masahiro Hoshino, Nobufumi Watanabe
  • Patent number: 7622614
    Abstract: The present invention is directed to novel methods for production of 5-epi-?-vetivone, 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-2,6-dien-8-one and 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-1,6-dien-8-one, which are useful for their fragrant qualities. In one embodiment the present invention describes a method for production of 5-epi-?-vetivone by the use of premnaspirodiene as starting material. In another embodiment the present invention describes a method for production of 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-2,6-dien-8-one and 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-1,6-dien-8-one by the use of premnaspirodiene as starting material. In yet another embodiment the present invention describes a novel method for production of premnaspirodiene from a terpene substrate.
    Type: Grant
    Filed: March 20, 2008
    Date of Patent: November 24, 2009
    Assignee: Allylix, Inc.
    Inventors: Bryan N. Julien, David M. Wallace
  • Patent number: 7622615
    Abstract: There is provided a process with which the cycloalkane is oxidized so as to produce a cycloalkanol and/or a cycloalkanone with an improved conversion of the cycloalkane. Such process includes the steps of supplying the oxygen-containing gas and a liquid including the cycloalkane into a bubble forming apparatus so as to prepare a gas-liquid mixture, and supplying such gas-liquid mixture into a reaction vessel.
    Type: Grant
    Filed: April 10, 2008
    Date of Patent: November 24, 2009
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hajime Ishida, Masashi Yokota
  • Patent number: 7597090
    Abstract: The present invention provides an internal combustion engine which can produce several types of fuels from a single fuel as needed. The internal combustion engine comprises reforming means 3 for reforming a first fuel to be used in homogeneous charge compression ignition combustion into a second fuel having high ignitability, by making the first fuel contact with a catalyst formed from N-hydroxyphthalimide. The engine uses the second fuel when conducting diesel combustion. The engine can switch between the homogeneous charge compression ignition combustion with the use of the first fuel and the diesel combustion with the use of the second fuel. The engine conducts the homogeneous charge compression ignition combustion when a load is low, and conducts the diesel combustion when the load is high.
    Type: Grant
    Filed: March 12, 2007
    Date of Patent: October 6, 2009
    Assignee: Honda Motor Co., Ltd.
    Inventors: Kohtaro Hashimoto, Kohjiroh Aimoto, Takahiro Gunji, Fumiaki Ikegawa
  • Patent number: 7579506
    Abstract: The invention relates to a method for the preparation of cyclohexanone from cyclohexane. The invention relates more particularly to a method for the production of cyclohexane whose impurity content enables cyclohexanone to be used as a raw material for the production of e-caprolactam. The inventive method consists in treating the mixture of cyclohexanol/cyclohexanone arising from oxidation of cyclohexane by oxygen in a dehydrogenation stage in order to transform cyclohexanol into cyclohexanone and the impurities present such as cyclopentenal. The inventive method makes it possible to obtain highly pure cyclohexanone which is compatible when used as a raw material in the synthesis of e-caprolactam.
    Type: Grant
    Filed: November 30, 2005
    Date of Patent: August 25, 2009
    Assignee: Rhodia Chimie
    Inventors: Philippe Leconte, Serge Veracini, Philippe Morel
  • Publication number: 20090076308
    Abstract: The present invention relates to a continuous method for oxidizing saturated cyclic hydrocarbons by oxygen to obtain a mixture of hydroperoxides, alcohols and ketones. It relates more particularly to a method for oxidizing cyclohexane in a column forming a bubble reactor, for the formation of cyclohexyl hydroperoxide, cyclohexanol and cyclohexanone. According to the invention, the column may be supplied with oxygen-enriched air, while meeting the maximum oxygen concentration requirements in the headspace of the reactor to avoid any risk of explosion.
    Type: Application
    Filed: October 6, 2005
    Publication date: March 19, 2009
    Inventors: Serge Veracini, Frederic Augier
  • Patent number: 7335796
    Abstract: The invention relates to a process for the preparation of a ketone from a tertiary alcohol having a double bond in the alpha position, that includes the step of contacting tertiary alcohol having a double bond in the alpha position with ozone in the presence of an inorganic base under ketone-forming reaction conditions.
    Type: Grant
    Filed: April 4, 2006
    Date of Patent: February 26, 2008
    Assignee: Symrise GmbH & Co., KG
    Inventor: Markus Nobis
  • 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: 7169954
    Abstract: A ruthenium-carrying alumina, which is prepared by suspending alumina in a solution containing trivalent ruthenium and adding a base to the suspension, is provided. This ruthenium-carrying alumina is useful as a catalyst for oxidizing alcohols by contacting the alcohols with molecular oxygen, and can be used for oxidizing the alcohols at a high conversion to produce ketones, aldehydes, carboxylic acids, etc. with good productivity.
    Type: Grant
    Filed: April 25, 2003
    Date of Patent: January 30, 2007
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noritaka Mizuno, Kazuya Yamaguchi, Hajime Ishida
  • 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: 7081552
    Abstract: A cyclic ketone/alcohol mixture is prepared by catalytic oxidation of the corresponding cycloalkane or catalytic decomposition of the corresponding cycloalkyl hydroperoxide. Gold supported on a porous crystalline silicate containing less than about 2 wt. % aluminum or a crystalline phosphate is used as a catalyst. The support material optionally contains one or more heteroatoms.
    Type: Grant
    Filed: August 17, 2004
    Date of Patent: July 25, 2006
    Assignee: Solutia Inc.
    Inventors: Larisa V. Pirutko, Alexander S. Kharitonov, Mikhail I. Khramov, Anthony K. Uriarte
  • Patent number: 7030279
    Abstract: An alcohol can be oxidized by a process in which a primary or secondary alcohol are reacted with an oxygen-containing gas in the presence of a catalyst composition containing (i) a stable free nitroxyl radical derivative, (ii) a nitrate source, (iii) a bromide source, and (iiii) a carboxylic acid, thereby obtaining an aldehyde or a ketone.
    Type: Grant
    Filed: December 23, 2004
    Date of Patent: April 18, 2006
    Assignee: Degussa AG
    Inventors: Setrak Tanielyan, Robert Augustine, Oliver Meyer, Michael Korell
  • Patent number: 7019175
    Abstract: The invention provides a process for the catalytic oxidation of an alkane, which comprises contacting the alkane with a source of oxygen in the presence of a catalyst comprising a compound of the formula (2) where R1 and R2 independently represent a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a cycloalkyl group, a hydroxyl group, an alkoxy group, a carboxyl group, an alkoxycarbonyl group, or an acyl group, or R1 and R2 may together form a double bond or an aromatic or non-aromatic ring; Y represents an oxygen atom or a sulfur atom; X represents an oxygen atom or a hydroxyl group; m denotes an integer of 0 to 4; and n denotes an integer of 1 to 3. Compounds in accordance with formula (2) possess good catalytic properties, such that when they are employed in a process in accordance with the present invention, they are capable of activating a source of oxygen and promoting the oxidation of an alkane at mild reaction temperatures.
    Type: Grant
    Filed: May 30, 2002
    Date of Patent: March 28, 2006
    Assignee: Imperial Chemical Industries PLC
    Inventors: Xavier Baucherel, Roger Arthur Sheldon
  • Patent number: 6930209
    Abstract: A method for liquid phase oxidation of a cycloalkane compound is provided by which the cycloalkane compound intended to be oxidized mixes with water to form an azeotropic mixture, and then an oxygen enriched gas is introduced to perform an oxidation reaction. This method is particularly suitable for liquid phase oxidation of cyclohexane by using an oxygen enriched gas or pure oxygen, which not only enhances conversion rate and selectivity of the cyclohexane oxidation process but also improves process safety in the use of an oxygen enriched gas or pure oxygen for cyclohexane oxidation.
    Type: Grant
    Filed: May 20, 2003
    Date of Patent: August 16, 2005
    Assignee: Chinese Petrochemical Development Co., Ltd.
    Inventors: Jenq-Renn Chen, Hsiao-Hui Yang, Chung-Ho Wu
  • Patent number: 6888034
    Abstract: Process for oxidizing cyclohexane in which oxygen is contacted with cyclohexane at a pre-selected feed rate in a first reaction zone and unconsumed oxygen is contacted with cyclohexane in a second reaction zone in which the cyclohexane feed rate is lower than the pre-selected feed rate.
    Type: Grant
    Filed: November 5, 2003
    Date of Patent: May 3, 2005
    Assignee: Invista North America S.A.R.L.
    Inventors: David Paul Landray, Ludovic Rick Fodor, Bruce Edwin Murphree, James Marvin Rung
  • Patent number: 6881870
    Abstract: There is provided a process for producing adamantanol and adamantanone which comprises reacting adamantane and oxygen in the presence of an oxidation catalyst constituted of a rare earth metal salt and a promoter containing an element selected from group 4 to group 10 of the new Periodic Table, and it is made possible through the production process according to the present invention to produce 2-adamantanol and 2-adamantanone in a high selectivity, high efficiency and safety by oxidizing adamantane under a mild reaction condition.
    Type: Grant
    Filed: June 24, 2002
    Date of Patent: April 19, 2005
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Kiyoshi Otsuka, Ichiro Yamanaka
  • Publication number: 20040199022
    Abstract: There is provided a process for producing adamantanol and adamantanone which comprises reacting adamantane and oxygen in the presence of an oxidation catalyst constituted of a rare earth metal salt and a promoter containing an element selected from group 4 to group 10 of the new Periodic Table, and it is made possible through the production process according to the present invention to produce 2-adamantanol and 2-adamantanone in a high selectivity, high efficiency and safety by oxidizing adamantane under a mild reaction condition.
    Type: Application
    Filed: December 29, 2003
    Publication date: October 7, 2004
    Inventors: Kiyoshi Otsuka, Ichiro Yamanaka
  • Publication number: 20040162445
    Abstract: A method for liquid phase oxidation of a cycloalkane compound is provided by which the cycloalkane compound intended to be oxidized mixes with water to form an azeotropic mixture, and then an oxygen enriched gas is introduced to perform an oxidation reaction. This method is particularly suitable for liquid phase oxidation of cyclohexane by using an oxygen enriched gas or pure oxygen, which not only enhances conversion rate and selectivity of the cyclohexane oxidation process but also improves process safety in the use of an oxygen enriched gas or pure oxygen for cyclohexane oxidation.
    Type: Application
    Filed: May 20, 2003
    Publication date: August 19, 2004
    Applicant: Chinese Petrochemical Development Co., Ltd.
    Inventors: Jenq-Renn Chen, Hsiao-Hui Yang, Chung-Ho Wu
  • Publication number: 20040138506
    Abstract: Aliphatic or alicyclic monoketones or alicyclic diketones of formula (I): R1—C(═O)—R2, wherein R1 is a linear or branched C1-10-alkyl group and R2 is a linear or branched C1-10-alkyl group or a phenyl group, or R1 and R2 together are —(CH2)m—[C(═O)]n—(CH2)p—, wherein m and p independently are integers from 1 to 4 and n is 0 or 1, thus forming an alicyclic ring together with the carbonyl group of (I), are produced by oxidizing an alcohol of formula (II): R1′—CHOH—R2′, in which R1′ and R2′ either have the same meaning as R1 and R2 above or, if R1 and R2 together are —(CH2)m—[C(═O]n—(CH2)p—, are together —(CH2)m—(CHOH)n—(CH2)p— wherein m, n and p are as defined above, with a peroxy compound in the presence of a carboxylic acid and a manganese(IV) complex of 1,4,7-trimethyl-1,4,7-triazacyclononane.
    Type: Application
    Filed: October 27, 2003
    Publication date: July 15, 2004
    Inventors: Georg Sss-Fink, Georgiy B Shul'Pin, Lidia S Shul'Pina
  • Publication number: 20040054235
    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: Application
    Filed: September 12, 2002
    Publication date: March 18, 2004
    Inventors: Ludovic Fodor, Bhagya Chandra Sutradhar
  • Publication number: 20040010164
    Abstract: The present invention relates to a process for the production of canthaxanthin by oxidation of beta-carotene or carotinoids derived therefrom which have conjugated double bonds.
    Type: Application
    Filed: June 6, 2003
    Publication date: January 15, 2004
    Applicant: Degussa AG
    Inventors: Frank Dubner, Jurgen Bilz, Christoph Weckbecker, Klaus Huthmacher
  • 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: 20030212283
    Abstract: A process of activating a fresh catalyst or regenerating a deactivated catalyst which is used in a hydro-oxidation process, preferably, the hydro-oxidation of an olefin in the presence of oxygen and hydrogen to an olefin oxide. The hydro-oxidation catalyst preferably comprises at least one metal selected from gold, silver, the platinum group metals, the lanthanide metals, and combinations thereof, incorporated onto a titanium- , vanadium- , or zirconium-containing support more preferably, a titanium-containing support, such as titanium oxide or a titanosilicate. The activation or regeneration process involves contacting the fresh catalyst or the deactivated catalyst with ozone.
    Type: Application
    Filed: September 30, 2002
    Publication date: November 13, 2003
    Inventors: Deborah H. Parker, Robert G. Bowman, Howard W. Clark, George E. Hartwell, Alex Kuperman
  • Patent number: 6642419
    Abstract: In the presence of (1) an oxidizing catalyst comprising an imide compound such as N-hydroxyphthalimide, or (2) an oxidizing catalyst comprising such imide compound and a transition metal element-containing compound as a co-oxidizing agent (e. g., oxides, halides, complexes, hetero polyacid salts) a hydrocaron, an alcohol, an aldehyde, or a ketone as a substrate is brought into contact with molecular oxygen for oxidation. In the above-described oxidation process, the water content of the oxidizing reaction system is 200 mol or lower relative to 1 mol of the imide compound. According to the present invention, a substrate is efficiently oxidized with molecular oxygen under mild conditions, and there can be obtained the object compound(s) of high quality.
    Type: Grant
    Filed: October 18, 2000
    Date of Patent: November 4, 2003
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Hiroyuki Miura, Hitoshi Watanabe, Tomohide Ina, Hidehiko Nakajima
  • Publication number: 20030144541
    Abstract: The invention concerns a method for preparing &agr;-halogenated ketones from secondary &agr;-halogenated alcohols. More particularly, the invention concerns the preparation of &agr;-trihalogenated ketones from secondary &agr;-trihalogenated alcohols. The method for preparing said &agr;-halogenated ketone is characterized in that it consists in oxidizing in liquid phase, a secondary &agr;-halogenated alcohol, using molecular oxygen or a gas containing same, in the presence of a catalyst based on a metal M1 selected among metals of group 1b and 8 of the periodic system of elements and optionally an activating element.
    Type: Application
    Filed: November 4, 2002
    Publication date: July 31, 2003
    Inventor: Roland Jacquot
  • 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: 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: 6459002
    Abstract: Cyclohexanone, cyclohexanol and/or cyclohexyl hydroperoxide are prepared at a high productivity by allowing cyclohexane to be in contact with an oxygen-containing gas using a catalyst comprising a cyclic N-hydroxyimide and a transition metal compound in the presence of cyclohexanone and optional cyclohexanol.
    Type: Grant
    Filed: November 26, 2001
    Date of Patent: October 1, 2002
    Assignees: Sumitomo Chemical Company, Limited, Daicel Chemical Industries, Ltd.
    Inventors: Shuzo Murata, Nobuhiro Tani
  • Publication number: 20020077510
    Abstract: Improved, safe process for the purification of ketones obtained by ozonolysis and subsequent reduction of the corresponding terpenes, in which, after the ozonolysis and reduction of acyclic mono-, bi- or tricyclic terpenes with ozonizable double bonds, converting the resulting corresponding crude ketone into a high-purity ketone by means of steam distillation at atmospheric pressure or at reduced pressure, extraction of the steam distillate and subsequent distillation.
    Type: Application
    Filed: December 12, 2001
    Publication date: June 20, 2002
    Inventors: Karlheinz Giselbrecht, Josef Schaller, Rudolf Hermanseder, Klaus Reiter
  • Publication number: 20020065436
    Abstract: Cyclohexanone, cyclohexanol and/or cyclohexyl hydroperoxide are prepared at a high productivity by allowing cyclohexane to be in contact with an oxygen-containing gas using a catalyst comprising a cyclic N-hydroxyimide and a transition metal compound in the presence of cyclohexanone and optional cyclohexanol.
    Type: Application
    Filed: November 26, 2001
    Publication date: May 30, 2002
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED, DAICEL CHEMICAL INDUSTRIES, LTD.
    Inventors: Shuzo Murata, Nobuhiro Tani
  • 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
  • Publication number: 20020016513
    Abstract: The first embodiment of the present invention provides a process, which includes:
    Type: Application
    Filed: January 24, 2001
    Publication date: February 7, 2002
    Applicant: Degussa-Huels Aktiengesellschaft
    Inventors: Stephan Laue, Andreas Liese, Christian Wandrey, Olaf Burkhardt, Jens Woeltinger, Andreas Bommarius, Karlheinz Drauz, Jean-Louis Philippe, Hans Henniges, Adreas Karau
  • Publication number: 20020004616
    Abstract: A process for oxidizing a cycloalkane, includes contacting a gas with a starting mixture, to form a product mixture, where the starting mixture contains (i) a cycloalkane, (ii) boric acid, and (iii) cobalt. The gas contains oxygen, the cycloalkane has 9 to 16 carbon atoms, and the product mixture contains a cyclic alcohol. The reactor output is increased by adding the cobalt salt, so that it is possible to lower the temperature, which decreases the rate of parallel and secondary reactions.
    Type: Application
    Filed: October 25, 1999
    Publication date: January 10, 2002
    Inventors: GERDA GRUND, BERND GUENZEL