Preparing By Oxidation Patents (Class 568/836)
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Publication number: 20150105590Abstract: A process for preparing cyclohexanol and cyclohexanone by cyclohexane oxidation includes steps of: non-catalyticly oxidizing cyclohexane with molecular oxygen in the air to obtain an oxidation mixture containing CHHP as a main product; performing a homogenous catalytic decomposition of the CHHP to obtain cyclohexanol and cyclohexanone; and rectifying to obtain products of the cyclohexanol and the cyclohexanone, wherein the step of performing the homogenous catalytic decomposition involves a homogeneous catalytic decomposition reaction and distillation vessel which removes water via azeotropic rectification to reduce a water content of a decomposition liquid to be below 100 ppm. A device therefor includes the homogeneous catalytic decomposition reaction and distillation vessel for performing the homogenous catalytic decomposition of the CHHP.Type: ApplicationFiled: May 17, 2012Publication date: April 16, 2015Inventor: Zaosheng Xiao
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Publication number: 20150099876Abstract: This invention relates to molecular catalysts and chemical reactions utilizing the same, and particularly to molecular catalysts for efficient catalytic oxidation of hydrocarbons, such as hydrocarbons from natural gas. The molecular catalytic platform provided herein is capable of the facile oxidation of hydrocarbons, for example, under ambient conditions such as near room temperature and atmospheric pressure.Type: ApplicationFiled: October 2, 2014Publication date: April 9, 2015Inventors: Sunney Ignatius CHAN, Sheng-Fa YU, Penumaka NAGABABU, Suman MAJI, Ping-Yu CHEN, Ravirala RAMU, Chung-Yuan MOU, Chih-Cheng LIU
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Patent number: 8981157Abstract: 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: GrantFiled: May 9, 2012Date of Patent: March 17, 2015Assignee: Ever Nu Technology, LLCInventors: Manhua Lin, Xiang Wang, Younghoon Yeom
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Publication number: 20150073179Abstract: A process for preparing cyclohexanol and cyclohexanone by cyclohexane oxidation, includes steps of: firstly processing uncatalyzed oxidation on cyclohexane by molecular oxygen, in such a manner that an oxidized mixture with cyclohexyl hydrogen peroxide serving as a primary product is generated; then decomposing the cyclohexyl hydrogen peroxide to produce cyclohexanol and cyclohexanone; and then distilling to obtain a cyclohexanol product and a cyclohexanone product, wherein the step decomposing the cyclohexyl hydrogen peroxide utilizes a three-step decomposition process including steps of: (1) performing the homogeneous catalytic decomposition by utilizing the bis(tert-butyl)chromate as a catalyst; (2) performing the heterogeneous catalytic decomposition of the sodium hydroxide alkaline aqueous solution under low alkalinity; and (3) performing the heterogeneous catalytic decomposition of the sodium hydroxide alkaline aqueous solution under high alkalinity.Type: ApplicationFiled: May 17, 2012Publication date: March 12, 2015Inventor: Zaosheng Xiao
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Patent number: 8940939Abstract: A process of oxidizing cyclohexane, comprising feeding cyclohexane, an aqueous hydrogen peroxide solution and optionally an organic solvent into a reaction zone through a feed inlet thereof under the oxidation reaction conditions for contact, and providing all or most of the oxidation product at the reaction zone bottom, wherein a part or all of the packing in the reaction zone is a titanium silicate molecular sieve-containing catalyst. The process of oxidizing cyclohexane according to the present invention carries out the oxidation in the reaction zone, which, firstly, utilizes the latent heat from reaction sufficiently so as to achieve energy-saving; secondly, increases the yield of target product and the availability of oxidizer; and thirdly, allows the separation of the oxidation product from the raw material cyclohexane as the reaction proceeds, such that the cost for subsequent separations can be saved.Type: GrantFiled: May 2, 2012Date of Patent: January 27, 2015Assignees: China Petroleum & Chemical Corporation, Research Institute of Petroleum Processing, SinopecInventors: Min Lin, Chunfeng Shi, Bin Zhu, Yingchun Ru
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Publication number: 20150011797Abstract: The present invention relates to a process for the oxidation of cycloalkanes utilising a supported gold and palladium catalyst and the use of the supported gold and palladium catalyst for the oxidation of cycloalkanes. Also described is a process for the preparation of the supported catalyst.Type: ApplicationFiled: February 1, 2013Publication date: January 8, 2015Applicant: INVISTA NORTH AMERICA S.A R.L.Inventors: Keith Whiston, Xi Liu, Graham Hutchings
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Patent number: 8658839Abstract: In a process for oxidizing a hydrocarbon to a corresponding hydroperoxide, alcohol, ketone, carboxylic acid or dicarboxylic acid, the hydrocarbon is contacted with an oxygen-containing gas in the presence of a catalyst comprising a cyclic imide of the general formula (I): wherein each of R1 and R2 is independently selected from hydrocarbyl and substituted hydrocarbyl radicals having 1 to 20 carbon atoms, or from the groups SO3H, NH2, OH and NO2, or from the atoms H, F, Cl, Br and I provided that R1 and R2 can be linked to one another via a covalent bond; each of Q1 and Q2 is independently selected from C, CH, N and CR3; each of X and Z is independently selected from C, S, CH2, N, P and elements of Group 4 of the Periodic Table; Y is O or OH; k is 0, 1, or 2; l is 0, 1, or 2; m is 1 to 3, and R3 can be any of the entities listed for R1.Type: GrantFiled: October 8, 2008Date of Patent: February 25, 2014Assignee: ExxonMobil Chemical Patents Inc.Inventors: Jihad M. Dakka, James C. Vartuli, Stephen Zushma
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Publication number: 20130204038Abstract: A method for oxidizing hydrocarbons, in particular saturated hydrocarbons, for producing peroxides, alcohols, ketones, aldehydes and/or diacids is described. Also described, is a method for oxidizing a cycloaliphatic saturated hydrocarbon using molecular oxygen for producing ketones/alcohols, and more precisely for oxidizing cyclohexane into cyclohexanol and cyclohexanone using molecular oxygen.Type: ApplicationFiled: January 14, 2011Publication date: August 8, 2013Applicant: RHODIA OPERATIONSInventors: Sophie Galinat, Francoise Igersheim, Serge Veracini
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Publication number: 20130203984Abstract: In a process for oxidizing a hydrocarbon to a product comprising at least one of the corresponding hydroperoxide, alcohol, ketone, carboxylic acid and dicarboxylic acid, the hydrocarbon is contacted with an oxygen-containing compound in at least one oxidation zone in the presence of a catalyst comprising a cyclic imide having an imide group of formula (I): wherein X represents an oxygen atom, a hydroxyl group, or an acyloxy group and wherein the oxygen-containing compound supplied to said at least one oxidation zone has a water content of less than or equal to 0.6% by weight of the oxygen-containing compound.Type: ApplicationFiled: August 16, 2011Publication date: August 8, 2013Inventors: Christopher L. Becker, Jihad M. Dakka, Franisco M. Benitez, Edmund J. Mozeleski
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Publication number: 20130184494Abstract: 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: ApplicationFiled: September 26, 2011Publication date: July 18, 2013Applicant: USE Industries, Ltd.Inventors: Kazunori Kurosawa, Joji Funatsu, Naoya Katagiri, Junichi Kugimoto
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Patent number: 8088953Abstract: Disclosed herein is a method for cyclohexane oxidation. The method comprises a) forming a dispersion comprising liquid cyclohexane and an oxidant gas utilizing a high shear device, wherein the dispersion comprises oxidant gas bubbles with a mean diameter of less than about 5 ?m, and wherein the high shear device comprises at least one rotor and at least one stator; and b) hydrogenating the dispersion in the presence of a hydrogenation catalyst to form a product comprising cyclohexanol or cyclohexanone. In some embodiments, the oxidant comprises air, oxygen-enriched air, oxygen, or an oxygen-containing gas. In some embodiments, step a) of the method comprises forming the dispersion in the presence of an oxidation catalyst. Also disclosed herein is a system for oxidizing cyclohexane.Type: GrantFiled: December 1, 2009Date of Patent: January 3, 2012Assignee: H R D CorporationInventors: Abbas Hassan, Aziz Hassan, Gregory G. Borsinger, Krishnan Viswanathan, Rayford G. Anthony
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Patent number: 7956221Abstract: 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: GrantFiled: December 16, 2005Date of Patent: June 7, 2011Assignee: DSM IP Assets B.V.Inventor: Imre Toth
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Patent number: 7923583Abstract: 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: GrantFiled: February 25, 2009Date of Patent: April 12, 2011Assignee: Sumitomo Chemical Company, LimitedInventors: Masahiro Hoshino, Nobufumi Watanabe, Keisuke Sugita
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Patent number: 7868201Abstract: A process for the oxidation of hydrocarbons comprises contacting the hydrocarbon with an oxygen-containing gas in the presence of a catalyst comprising a microporous solid support, preferably a zeolite, having from 8- to 12-ring open windows and comprising non-framework metal cations selected from manganese, iron, cobalt, vanadium, chromium, copper, nickel, and ruthenium, and mixtures thereof, providing that the oxygen-containing gas does not contain significant amounts of added hydrogen. The catalyst is novel and forms part of the invention. The process may be used for oxidation of alkanes, cycloalkanes, benzene and alkylbenzenes, and is suitable for use in regioselective terminal oxidation of straight chain alkanes and for selective oxidation/separation of p-dialkylbenzenes from an alkylbenzene mixture, for example, p-xylene from an isomeric mixture of xylenes.Type: GrantFiled: July 1, 2005Date of Patent: January 11, 2011Assignee: ExxonMobil Research and Engineering CompanyInventors: Bi-Zeng Zhan, Bjorn Moden, Jihad Dakka, Jose Santiesteban, Sebastian C. Reyes, Enrique Iglesia
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Patent number: 7834217Abstract: 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: GrantFiled: November 30, 2007Date of Patent: November 16, 2010Assignee: Daicel Chemical Industries, Ltd.Inventors: Takumi Omori, Yasushi Sato
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Publication number: 20100168477Abstract: Disclosed herein is a method for cyclohexane oxidation. The method comprises a) forming a dispersion comprising liquid cyclohexane and an oxidant gas utilizing a high shear device, wherein the dispersion comprises oxidant gas bubbles with a mean diameter of less than about 5 ?m, and wherein the high shear device comprises at least one rotor and at least one stator; and b) hydrogenating the dispersion in the presence of a hydrogenation catalyst to form a product comprising cyclohexanol or cyclohexanone. In some embodiments, the oxidant comprises air, oxygen-enriched air, oxygen, or an oxygen-containing gas. In some embodiments, step a) of the method comprises forming the dispersion in the presence of an oxidation catalyst. Also disclosed herein is a system for oxidizing cyclohexane.Type: ApplicationFiled: December 1, 2009Publication date: July 1, 2010Applicant: H R D CORPORATIONInventors: Abbas Hassan, Aziz Hassan, Gregory G. Borsinger, Krishnan Viswanathan, Rayford G. Anthony
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Patent number: 7741523Abstract: 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: GrantFiled: October 6, 2005Date of Patent: June 22, 2010Assignee: Rhodia ChimieInventors: Serge Veracini, Frédéric Augier
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Publication number: 20100081848Abstract: 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: ApplicationFiled: November 30, 2007Publication date: April 1, 2010Inventors: Takumi Omori, Yasushi Sato
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Patent number: 7615667Abstract: 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. Cycloalkanol and/or cycloalkanone are produced by oxidizing cycloalkane with oxygen in the presence of a catalyst comprising calcium oxide and a transition metal supported on the calcium oxide. The transition metal is preferably at least one metal selected from cobalt, gold, vanadium, chromium, manganese, iron, ruthenium and palladium, and more preferably cobalt or gold.Type: GrantFiled: November 12, 2008Date of Patent: November 10, 2009Assignee: Sumitomo Chemical Company, LimitedInventor: Avelino Corma
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Patent number: 7592493Abstract: Use of a high shear mechanical device incorporated into a process for the production of cyclohexanol is capable of decreasing mass transfer limitations, thereby enhancing the cyclohexanol production process. A system for the production of cyclohexanol from air oxidation of cyclohexane, the system comprising a high shear device, the outlet of the high shear device fluidly connected to the inlet of a reactor; the high shear device capable of providing a dispersion of air bubbles within a liquid comprising cyclohexane, the bubbles having an average bubble diameter of less than about 100 ?m.Type: GrantFiled: June 12, 2008Date of Patent: September 22, 2009Assignee: H R D CorporationInventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Publication number: 20090227814Abstract: 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: ApplicationFiled: February 25, 2009Publication date: September 10, 2009Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Masahiro HOSHINO, Nobufumi Watanabe, Keisuke Sugita
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Patent number: 7579506Abstract: 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: GrantFiled: November 30, 2005Date of Patent: August 25, 2009Assignee: Rhodia ChimieInventors: Philippe Leconte, Serge Veracini, Philippe Morel
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Patent number: 7541500Abstract: In case of oxidizing cycloalkane with oxygen, the catalyst to be used is a catalyst obtained by supporting metals of Groups 5 to 10 of the Periodic Table on a carrier, the carrier being subjected to a catalytic treatment with an organosilicon compound. The metal is preferably vanadium, chromium, manganese, iron, cobalt, ruthenium or palladium, while the carrier is preferably an oxide of magnesium, aluminum, silicon, titanium or zirconium.Type: GrantFiled: February 26, 2007Date of Patent: June 2, 2009Assignee: Sumitomo Chemical Company, LimitedInventor: Masahiro Hoshino
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Publication number: 20090036714Abstract: 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: ApplicationFiled: August 1, 2008Publication date: February 5, 2009Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Masahiro HOSHINO, Nobufumi Watanabe
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Patent number: 7432402Abstract: The present invention relates to new crystalline molecular sieve SSZ-74 prepared using a hexamethylene-1,6-bis-(N-methyl N-pyrrolidinium) dication as a structure-directing agent, and processes employing SSZ-74 in a catalyst.Type: GrantFiled: December 21, 2006Date of Patent: October 7, 2008Assignee: Chevron U.S.A.Inventors: Stacey I. Zones, Allen W. Burton, Jr.
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Patent number: 7358401Abstract: 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 cobalt is supported on layer silicate cycloalkane. Said oxidation is performed in the coexistence of a heteropoly acid compound and the heteropoly acid compound preferably contains cobalt as a central element and/or a skeletal element.Type: GrantFiled: March 28, 2006Date of Patent: April 15, 2008Assignee: Sumitomo Chemical Company, LimitedInventors: Avelino Corma, Jose Manuel Lopez Nieto, Marcelo Eduardo Domine
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Patent number: 7145041Abstract: 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: GrantFiled: June 12, 2002Date of Patent: December 5, 2006Assignee: Degussa AGInventors: Adolf Kuehnle, Carsten Jost, Roger Arthur Sheldon, Sandrine M. M. Chatel, Isabella W. C. E. Arends
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Patent number: 7087793Abstract: 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: GrantFiled: August 26, 2005Date of Patent: August 8, 2006Assignee: Sumitomo Chemical Company, LimitedInventors: Avelino Corma, Jose Manuel Lopez Nieto
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Patent number: 7087792Abstract: The present invention relates to new molecular sieve SSZ-71 prepared using a N-benzyl-1,4-diazabicyclo[2.2.2]octane cation as a structure-directing agent, methods for synthesizing SSZ-71 and processes employing SSZ-71 in a catalyst.Type: GrantFiled: November 2, 2005Date of Patent: August 8, 2006Assignee: Chevron U.S.A. Inc.Inventors: Cong-Yan Chen, Allen W. Burton, Jr., Ann J. Liang
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Patent number: 7084305Abstract: The present invention relates to new crystalline molecular sieve SSZ-70 prepared using a N,N?-diisopropyl imidazolium cation as a structure-directing agent, methods for synthesizing SSZ-70 and processes employing SSZ-70 in a catalyst.Type: GrantFiled: November 2, 2005Date of Patent: August 1, 2006Assignee: Chevron U.S.A. Inc.Inventors: Stacey I. Zones, Allen W. Burton, Jr.
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Patent number: 7081552Abstract: 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: GrantFiled: August 17, 2004Date of Patent: July 25, 2006Assignee: Solutia Inc.Inventors: Larisa V. Pirutko, Alexander S. Kharitonov, Mikhail I. Khramov, Anthony K. Uriarte
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Patent number: 7045667Abstract: A process for producing a cycloalkanol and/or a cycloalkanone is provided, the process comprising the step of oxidizing cycloalkane with molecular oxygen in the presence of a mixture of metal oxides and/or a composite metal oxide, each containing cerium and zirconium as the metal elements therein.Type: GrantFiled: September 27, 2004Date of Patent: May 16, 2006Assignee: Sumitomo Chemical Company, LimitedInventors: Hajime Ishida, Naoki Miura
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Patent number: 7019175Abstract: 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: GrantFiled: May 30, 2002Date of Patent: March 28, 2006Assignee: Imperial Chemical Industries PLCInventors: Xavier Baucherel, Roger Arthur Sheldon
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Patent number: 6960693Abstract: The present invention relates to an oxidation reaction catalyzed by a reaction controlled phase-transfer catalyst having the general formula of [R1R2R3R4N]xHy[A] or QmMO3(L). The catalysts themselves are not soluble in the reaction medium, but can form an active species that is soluble in the reaction medium under the action of one of the reactants. The active species can in turn react selectively with another reactant. When one of the reactants is completely consumed, the catalyst will separated out from the reacting system and can be recovered by means of simple separation method. The recovered catalyst can be recycled with comparable efficiency as that of the original catalyst. The separation of said catalyst is similar to that of heterogeneous catalyst while said catalyst will completely exhibit the characteristics of homogeneous catalyst during the reaction.Type: GrantFiled: November 29, 2001Date of Patent: November 1, 2005Assignees: China Petroleum & Chemical Corporation, Dalian Institute of Chemical Physics the Chinese Academy of SciencesInventors: Zuwei Xi, Yu Sun, Kunlan Li, Ning Zhou
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Patent number: 6930209Abstract: 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: GrantFiled: May 20, 2003Date of Patent: August 16, 2005Assignee: Chinese Petrochemical Development Co., Ltd.Inventors: Jenq-Renn Chen, Hsiao-Hui Yang, Chung-Ho Wu
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Patent number: 6927311Abstract: A method for producing an oxygenated compound from a cycloalkane compound which method is characterized in that a cycloalkane compound is contacted with oxygen in the presence of a cobalt compound and a ruthenium compound.Type: GrantFiled: March 26, 2003Date of Patent: August 9, 2005Assignee: Sumitomo Chemical Company, LimitedInventors: Nobuhiro Tani, Shuzo Murata
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Patent number: 6911563Abstract: A method for carrying out a reaction of one substance capable of being activated by a catalyst with another substance capable of reacting with said one substance activated, characterized in that the substance capable of being activated is activated by passing the substance through a diaphragm type catalyst and the reaction is thus performed in one reaction step; a method for producing an aromatic alcohol utilizing the above method; and a reaction apparatus suitable for these reactions. In the method, one substance is activated by passing through a diaphragm type catalyst and an objective reaction is carried out by using the activated substance, and the reaction can be performed in one reaction step and with safety. Moreover, the contact of the above activated substance with a compound to be reacted therewith can be freely controlled, and therefore, over-reaction can be prevented and an objective product can be produced in high yield.Type: GrantFiled: December 27, 2001Date of Patent: June 28, 2005Assignees: National Institute of Advanced Industrial Science, NOK CorporationInventors: Fujio Mizukami, Shuichi Niwa, Makoto Toba, Naotsugu Itoh, Tomonari Saito, Takemi Nanba, Hiroshi Shoji, Kazuhiko Haba
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Patent number: 6888034Abstract: 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: GrantFiled: November 5, 2003Date of Patent: May 3, 2005Assignee: Invista North America S.A.R.L.Inventors: David Paul Landray, Ludovic Rick Fodor, Bruce Edwin Murphree, James Marvin Rung
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Patent number: 6814867Abstract: Disclosed herein is a process for reducing or substantially eliminating chromium in non-volatile residue obtained from a certain processes, and particularly from cyclohexane oxidation processes.Type: GrantFiled: September 12, 2002Date of Patent: November 9, 2004Assignee: Inuista North America S.à.r.l.Inventors: Ludovic Fodor, Bennett Haines Novak, Jules Charles Joseph Perilloux, Jr., Bhagya Chandra Sutradhar
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Patent number: 6806390Abstract: 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: GrantFiled: February 11, 2003Date of Patent: October 19, 2004Assignee: Inuista North America S.àr.l.Inventors: Norman Herron, Stephan Schwarz, Joe Douglas Druliner
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Publication number: 20040162445Abstract: 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: ApplicationFiled: May 20, 2003Publication date: August 19, 2004Applicant: Chinese Petrochemical Development Co., Ltd.Inventors: Jenq-Renn Chen, Hsiao-Hui Yang, Chung-Ho Wu
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Publication number: 20040054235Abstract: 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: ApplicationFiled: September 12, 2002Publication date: March 18, 2004Inventors: Ludovic Fodor, Bhagya Chandra Sutradhar
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Patent number: 6703529Abstract: 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: GrantFiled: September 12, 2002Date of Patent: March 9, 2004Assignee: E. I. du Pont de Nemours and CompanyInventors: Ludovic Fodor, Bhagya Chandra Sutradhar
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Patent number: 6677490Abstract: 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: GrantFiled: October 15, 2002Date of Patent: January 13, 2004Assignee: Rhodia Polyamide IntermediatesInventors: James Clark, Eric Fache, Ducan Macquarrie, Peter Price, John Rafelt
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Publication number: 20030216601Abstract: A method for producing an oxygenated compound from a cycloalkane compound which method is characterized in that a cycloalkane compound is contacted with oxygen in the presence of a cobalt compound and a ruthenium compound.Type: ApplicationFiled: March 26, 2003Publication date: November 20, 2003Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Nobuhiro Tani, Shuzo Murata
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Patent number: 6642419Abstract: 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: GrantFiled: October 18, 2000Date of Patent: November 4, 2003Assignee: Daicel Chemical Industries, Ltd.Inventors: Hiroyuki Miura, Hitoshi Watanabe, Tomohide Ina, Hidehiko Nakajima
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Patent number: 6476275Abstract: Processes applying mesoporous titanium containing zeolite based catalysts for selective oxidation or epoxidation of hydrocarbons by peroxides.Type: GrantFiled: September 21, 2001Date of Patent: November 5, 2002Assignee: Haldor Topsoe A/SInventors: Iver Schmidt, Michael Brorson, Claus J. H. Jacobsen
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Patent number: 6294689Abstract: This invention relates to oxidative methods for controlling the oxidation of a class of compounds, including hydrocarbons, such as cyclohexane for example, alcohols, such as cyclohexanol for example, ketones, such as cyclohexanone for example, and peroxides, such as cyclohexylhydroperoxide for example, to intermediate oxidation products, such as adipic acid for example, by the removing the catalyst, such as cobalt compounds for example, from the oxidation mixture, outside the oxidation zone, after the oxidation has taken place at least partially. The catalyst is at least partially precipitated by following the steps of changing the temperature to be within a specific range, and sequentially reducing the water level to such a degree that causes the catalyst to precipitate. The precipitated catalyst is thereafter preferably filtered from the oxidation mixture and recycled to the oxidation zone.Type: GrantFiled: September 19, 2000Date of Patent: September 25, 2001Assignee: RPC Inc.Inventors: Mark W. Dassel, Ader M. Rostami, David C. DeCoster, Eustathios Vassiliou
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Patent number: 6255533Abstract: Organic by-products having higher boiling points than cyclohexanone (usually obtained from the bottoms of a distillation operation to separate cyclohexanone from other reaction products during cyclohexanone production) can be converted to recoverable cyclohexanone and cyclohexanol using a catalyst having high aluminum oxide concentrations. The preferred catalyst is one which has an aluminum oxide (Al2O3) content of at least about 95 wt. %, and more preferably greater than about 99 wt. %.Type: GrantFiled: November 9, 1999Date of Patent: July 3, 2001Assignee: BASF CorporationInventors: Andrew J. McNabb, Deirdre R. Williams
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Patent number: 6215027Abstract: The amount of a ballast gas needed, to prevent combustion, deflagration, and/or detonations during a liquid phase reaction of molecular oxygen and a flammable process liquid, is reduced by using a ballast gas other than nitrogen. The ballast gas is selected to have a boiling point lower than the boiling point of the flammable process liquid and selected to produce a higher limiting oxygen value (LOV) in a mixture with the flammable process liquid vapor and molecular oxygen than the LOV for the corresponding mixture substituting just nitrogen for the inerting gas.Type: GrantFiled: October 20, 1998Date of Patent: April 10, 2001Assignee: Praxair Technology, Inc.Inventors: Vasilis Papavassiliou, William Robert Williams, Matthew Lincoln Wagner