Heavy Metal Containing Material Utilized Patents (Class 568/360)
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Patent number: 11643381Abstract: Methods for aldehyde synthesis are provided. In one embodiment, a method for manufacturing aldehydes includes providing an aldehyde precursor stream and an air stream comprising nitrogen gas and oxygen gas to a reactor comprising a catalyst, reacting the aldehyde precursor stream and the oxygen gas, and converting the air stream to an oxygen gas stream when reacting the aldehyde precursor stream and oxygen gas.Type: GrantFiled: June 22, 2022Date of Patent: May 9, 2023Assignee: HEXION INC.Inventors: James M. Barker, Roy Smith, Gerlof Bouma
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Patent number: 11572330Abstract: The present invention concerns a method of oxidizing a cycloalkane to form a product mixture containing a corresponding alcohol and ketone, said method comprising contacting the cycloalkane with a hydroperoxide compound in the presence of a heterogenous catalyst comprising gold.Type: GrantFiled: January 28, 2019Date of Patent: February 7, 2023Inventors: Sandra Chouzier, Sergio Mastroianni, Avelino Corma, Mercedes Boronat, Javier Tirso Lopez Ausens
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Patent number: 11495804Abstract: An air electrode catalyst for an air secondary battery includes a pyrochlore-type composite oxide having two or more crystal structures having a different amount of oxygen. A battery, according to some embodiments, includes an electrode group including an air electrode and a negative electrode stacked with a separator therebetween, and a container accommodating the electrode group along with an alkali electrolyte solution, wherein the air electrode includes the air electrode catalyst. The air electrode catalyst may have a pyrochlore-type composite oxide having a crystal structure represented by Bi2Ru2O6.92 and a crystal structure represented by Bi2Ru2O7.33.Type: GrantFiled: February 4, 2020Date of Patent: November 8, 2022Assignees: FDK CORPORATION, JAPAN METALS AND CHEMICALS CO., LTD.Inventors: Shohei Unoki, Takeshi Kajiwara, Takahiro Endo, Shigekazu Yasuoka, Yoshikatsu Watanabe
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Patent number: 11485985Abstract: A process for producing rotundone from ?-guaiene, in particular by oxidation of the C(3) position, wherein the ?-guaiene is produced from a precursor by a sesquiterpene synthase. The sesquiterpene synthase is produced in a microorganism.Type: GrantFiled: November 21, 2018Date of Patent: November 1, 2022Assignee: Givaudan SAInventors: Andreas Goeke, Julie Charpentier, Boris Schilling, Fridtjof Schröder
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Patent number: 11472760Abstract: A process is proposed for preparing unsaturated macrocyclic monoketones, comprising the following steps: (a) providing macrocyclic dienes having a ring size of at least 9 carbon atoms; (b) contacting the starting materials from step (a) with (b1) a palladium(II) salt and/or a palladium(II) complex; and (b2) an oxidizing agent; and (b3) a solvent; and optionally (b4) a ligand; and optionally (b5) a co-catalyst; and optionally (b6) an acid, with the proviso that the co-catalyst (b5) comprises or consists of a divalent or trivalent iron salt which is different from FeSO4 and is preferably iron(III) nitrate.Type: GrantFiled: January 17, 2019Date of Patent: October 18, 2022Assignee: Symrise AGInventors: Tom Brunzel, Angela Köckritz
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Patent number: 11261148Abstract: A method for producing a carbonyl compound represented by formula (1): wherein R1 is hydrogen or an organic group; R2 is hydrogen or an organic group; and R3 is hydrogen or an organic group; or two or three of R1, R2, and R3 may be linked to form a ring that may have at least one substituent, the method comprising step A of oxidizing an olefin compound represented by formula (2): wherein symbols are as defined above, by an oxidizing agent in the presence of (a) a non-alcohol organic solvent, (b) water, (c) a metal catalyst, and (d) an additive represented by the formula: MXn, wherein M is an element belonging to any one of Group 1, Group 2, Group 13, Group 14, and Group 15 in the periodic table, or NR4, wherein R is hydrogen or a C1-10 organic group; X is halogen; and n is a number of 1 to 5.Type: GrantFiled: March 7, 2019Date of Patent: March 1, 2022Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Masahiro Higashi, Satoru Yoneda, Sumi Ishihara, Yosuke Kishikawa
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Patent number: 11021426Abstract: A method for producing unsaturated macrocyclic monoketones comprising the following steps: (a) preparing macrocyclic dienes with a ring size of at least 9 carbon atoms; (b) contacting the starting materials from step (a) with (b1) a palladium(II) salt and/or a palladium(II) complex; and (b2) an oxidant; and (b3) a solvent; and optionally (b4) a ligand; and optionally (b5) a co-catalyst; and optionally (b6) an acid.Type: GrantFiled: October 25, 2017Date of Patent: June 1, 2021Assignee: Symrise AGInventors: Tom Brunzel, Angela Köckritz, Andreas Martin, Diego A. Jaime Trevino
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Patent number: 10752549Abstract: The present invention relates to modification of hydratable cement and cementitious materials, such as mortar cement and masonry or ready-mix concrete using ketone alcohol oil waste (“KAOW”) material, obtained as an alkali-soluble liquor waste byproduct at a certain stage in the commercial production of cyclohexanol and cyclohexanone. Preferred applications for KAOW are in chemical admixture formulations whereby KAOW is used to substitute for a portion of a cement dispersant such as sodium lignosulfonate, sodium gluconate, or other conventional dispersant. Another preferred use is in mortar cement and masonry concrete units such as blocks, pavers, curbstones, and other concrete masonry units wherein air void systems advantageously foster freeze-thaw durability.Type: GrantFiled: February 27, 2015Date of Patent: August 25, 2020Inventors: Shuqiang Zhang, Hua Zhong, Wee Fuk Lai, Felek Jachimowicz, Byong-wa Chun, Yin-Zar Hnin
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Patent number: 9822052Abstract: Methods for converting an alcohol, such as cyclohexanol to a ketone, such as cyclohexanone, include reacting the alcohol in the presence of a catalyst and oxygen to produce the ketone. In one exemplary embodiment, the catalyst comprises a microporous copper chloropyrophosphate framework including a plurality of noble metal nanoparticles. In one exemplary embodiment, the noble metal nanoparticles include at least one metal selected from the group consisting of platinum, palladium, and gold.Type: GrantFiled: September 29, 2016Date of Patent: November 21, 2017Assignees: ADVANSIX RESINS & CHEMICALS LLC, UNIVERSITY OF SOUTHAMPTONInventors: Alan B. Levy, Scott R. Keenan, Robert Raja, Arran M. Gill, Matthew E. Potter, Sivan A. Van Aswegen
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Patent number: 9409791Abstract: Provided is a visible active photocatalyst of formula BiOX wherein X=P or S and process of preparation and use thereof. Use of the catalyst is demonstrated in the photocatalytic degradation of pharmaceutical drug pollutants and pollutant dyes using solar radiation or artificial radiation.Type: GrantFiled: December 29, 2014Date of Patent: August 9, 2016Assignee: Council of Scientific & Industrial ResearchInventor: Sanjay Pandurang Kamble
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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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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: 8507728Abstract: A method for manufacturing a ketone includes oxidizing an internal olefin or a cyclic olefin having 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, thereby bonding an oxo group to at least one of the carbon atoms constituting the carbon-carbon double bond, in which the amide-based solvent is represented by the formula in the formula (1), 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: GrantFiled: November 24, 2009Date of Patent: August 13, 2013Assignee: JX Nippon Oil & Energy CorporationInventors: Kiyotomi Kaneda, Hisashi Sone
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Publication number: 20130172625Abstract: Methods for using ailylic oxidation catalysts to perform oxidation reactions. In an exemplary method for catalyzing an ailylic oxidation reaction of the present disclosure, the method comprises the step of catalyzing an oxidation of an ailylic compound using an ailylic oxidation catalyst. In at least one embodiment, the ailylic oxidation catalyst comprises palladium, gold, and titanium, In an exemplary embodiment, the ailylic oxidation catalyst comprises 2.5% A?÷2.5% Pd/TiO2.Type: ApplicationFiled: February 10, 2011Publication date: July 4, 2013Inventors: Brian Tarbit, Graham J. Hutchings, Jennifer K. Edwards, Peter Miedziak
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Publication number: 20130053585Abstract: Fe2(dobdc) has a metal-organic framework with a high density of coordinatively-unsaturated FeII centers lining the pore surface. It can be effectively used to separate O2 from N2 and in a number of additional separation applications based on selective, reversible electron transfer reactions. In addition to being an effective O2 separation material, it can be used for many other processes, including paraffin/olefin separation, nitric oxide/nitrous oxide separation, acetylene storage, and as an oxidation catalyst.Type: ApplicationFiled: August 24, 2012Publication date: February 28, 2013Applicant: The Regents of the University of CaliforniaInventors: Jeffrey R. LONG, Eric D. BLOCH, Leslie MURRAY
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Patent number: 8304581Abstract: The present invention relates to a method of enantioselective addition to enones, including: reacting R3(CH2)pCH?CR5C(?O)Y(CH2)qR4 with R6ZnR7 in the presence of a compound represented by the following formula (I) and a transition metal catalyst, in which Y, p, q, R1, R2, R3, R4, R5, R6 and R7 are defined the same as the specification. Accordingly, the present invention can perform asymmetric conjugate addition in high yields and enantioselectivity.Type: GrantFiled: July 19, 2010Date of Patent: November 6, 2012Assignee: National Tsing Hua UniversityInventors: Biing-Jiun Uang, Chih-Hao Tseng
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Patent number: 8258348Abstract: A process for producing a carbonyl compound corresponding to an olefin, the process comprising reacting the olefin with molecular oxygen in a water-containing liquid phase comprising a palladium catalyst, a vanadium compound, and a heteropoly acid having a heteropoly anion represented by the Formula: [XaMbM?cOd]n? wherein X is any of elements selected from P, Si, and S; a represents an integer of 1 or 2; M and M? represent any of elements selected from Mo, W, V, Ta, and Nb; b and c represent an integer of 0 or more; d represents an integer of 1 or more; and n represents an integer of 1 or more.Type: GrantFiled: March 18, 2009Date of Patent: September 4, 2012Assignee: Sumitomo Chemical Company, LimitedInventors: Junichi Nishimoto, Masayoshi Murakami
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Publication number: 20120220792Abstract: 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: ApplicationFiled: July 30, 2010Publication date: August 30, 2012Inventors: 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
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Publication number: 20110288340Abstract: A method for manufacturing a ketone includes oxidizing an internal olefin or a cyclic olefin having 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, thereby bonding an oxo group to at least one of the carbon atoms constituting the carbon-carbon double bond, in which the amide-based solvent is represented by the formula in the formula (1), 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: ApplicationFiled: November 24, 2009Publication date: November 24, 2011Applicant: JX NIPPON OIL & ENERGY CORPORATIONInventors: Kiyotomi Kaneda, Hisashl Sone
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Patent number: 7939692Abstract: 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: GrantFiled: January 3, 2007Date of Patent: May 10, 2011Assignee: Sumitomo Chemical Company, LimitedInventors: Roger Gläser, Sudhir Dapurkar, Carsten Stöcker, Junichi Nishimoto, Masayoshi Murakami
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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: 7897818Abstract: 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: GrantFiled: July 7, 2009Date of Patent: March 1, 2011Assignee: China Petrochemical Development CorporationInventors: Jui-Tsung Hung, Chin-Yi Lee, Chia-Jung Tsai
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Publication number: 20110021842Abstract: A process for producing a carbonyl compound, the process comprising reacting an olefin with molecular oxygen in the presence of a heteropoly anion, a palladium catalyst, and an iron compound, in an acetonitrile-containing aqueous solution, in the presence of an effective amount of a proton under a condition that an amount of an alkali metal in a reaction system is 1 or less g-atm per 1 mol of the heteropoly anion.Type: ApplicationFiled: March 17, 2009Publication date: January 27, 2011Inventors: Junichi Nishimoto, Masayoshi Murakami
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Publication number: 20110015444Abstract: A process for producing a carbonyl compound corresponding to an olefin, the process comprising reacting the olefin with molecular oxygen in a water-containing liquid phase comprising a palladium catalyst, a vanadium compound, and a heteropoly acid having a heteropoly anion represented by the Formula: [XaMbM?cOd]n? wherein X is any of elements selected from P, Si, and S; a represents an integer of 1 or 2; M and M? represent any of elements selected from Mo, W, V, Ta, and Nb; b and c represent an integer of 0 or more; d represents an integer of 1 or more; and n represents an integer of 1 or more.Type: ApplicationFiled: March 18, 2009Publication date: January 20, 2011Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Junichi Nishimoto, Masayoshi Murakami
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Publication number: 20100036172Abstract: 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: ApplicationFiled: July 7, 2009Publication date: February 11, 2010Applicant: China Petrochemical Development CorporationInventors: Jui-Tsung HUNG, Chin-Yi LEE, Chia-Jung TSAI
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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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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: 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: 20090131724Abstract: 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: ApplicationFiled: November 12, 2008Publication date: May 21, 2009Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventor: Avelino CORMA
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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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Publication number: 20080228007Abstract: 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: ApplicationFiled: March 14, 2008Publication date: September 18, 2008Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Masahiro HOSHINO, Tatsuya Suzuki, Hajime Ishida
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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: 7304185Abstract: There is provided a process for the production of carbonyl compounds, characterized by reacting a diol represented by the formula (1); wherein R1, R2, R3 and R4 are the same or different, and independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted acyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted aryloxycarbonyl group, a substituted or unsubstituted aralkyloxycarbonyl group, carboxyl group or a hydrogen atom, or R1 and R2 or R3 and R4 are bonded together with the carbon atoms to which they are bonded to form a ring, provided that all of R1, R2, R3 and R4 are not hydrogen atoms simultaneously; with bromine or an inorganic bromine compound in the presence of a trivalent bismuth compound and a base to form carbonyl compounds represented by the formula (2); wherein R1 and R3 are as defined above; and the formula (3); whereinType: GrantFiled: March 24, 2004Date of Patent: December 4, 2007Assignee: Sumitomo Chemical Company, LimitedInventors: Naoyuki Takano, Koji Hagiya
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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: 6881870Abstract: 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: GrantFiled: June 24, 2002Date of Patent: April 19, 2005Assignee: Idemitsu Kosan Co., Ltd.Inventors: Kiyoshi Otsuka, Ichiro Yamanaka
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Patent number: 6872856Abstract: A method is provided for making an enantiomerically pure compound of the formula: in which R and R? represent C1?C10 alkyl, C2?C10 alkenyl or C3?C10 cycloalkyl and the wedges signify (S)- or (R)-stereochemistry, the substituents in compound (II) being trans. Conjugate addition is carried out between an organometallic nucleophile that provides a group R as defined above and (R)-4-acetoxycyclopent-2-en-1-one, (S)-4-acetoxycyclopent-2-en-1-one or a similar compound in which acetoxy is replaced by another leaving group to give, e.g.Type: GrantFiled: June 28, 2001Date of Patent: March 29, 2005Assignee: Warner-Lambert CompanyInventors: David Clive Blakemore, Justin Stephen Bryans
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Patent number: 6790997Abstract: 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: GrantFiled: July 23, 2002Date of Patent: September 14, 2004Assignee: Bayer AktiengesellschaftInventors: Markus Eckert, Hans-Christian Militzer, Matthias Beller, Christian Döbler, Gerald Mehltretter, Uta Sundermeier
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Publication number: 20040158103Abstract: A cycloalkane, such as cyclohexane, is catalytically oxidized to form a ketone/alcohol mixture. A cycloalkane-containing reaction mixture is contacted with a source of oxygen in the presence of a catalytic effective amount of gold supported on a crystalline zeolite-like support. The zeolite-like support optionally contains one or more heteroatoms.Type: ApplicationFiled: February 11, 2003Publication date: August 12, 2004Applicant: Solutia Inc.Inventors: Larisa V. Pirutko, Alexander S. Kharitonov, Mikhail I. Khramov, Anthony K. Uriarte
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Patent number: 6716789Abstract: The disclosure is directed to a process for preparing an oxidic catalyst comprising copper in an oxidation state >0, which comprises treating a solid oxidic support material with an aqueous solution comprising at least one copper salt and at least one organic water soluble polymer which binds copper ions coordinatively in a concentration of from 0.1 to 100 g/l and then calcining, to the catalyst obtainable by this process and also to a process for dehydrogenating secondary alcohols to ketones using the catalysts, especially for dehydrogenating cyclohexanol.Type: GrantFiled: June 21, 2000Date of Patent: April 6, 2004Assignee: BASF AktiengesellschaftInventors: Daniel Heineke, Ruprecht Meissner, Michael Hesse, Henning-Peter Gehrken
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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: 6486357Abstract: 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: GrantFiled: August 14, 2001Date of Patent: November 26, 2002Assignee: The University of ConnecticutInventors: Steven L. Suib, Young Chan Son, Amy R. Howell
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Patent number: 6376422Abstract: Catalyst mixtures are comprised of zinc oxide, calcium carbonate or calcium oxide, and an amount of chromium (III) oxide in an amount sufficient to improve conversion and/or selectivity of cyclohexanol to cyclohexanone under cyclohexanol dehydrogenation conditions.Type: GrantFiled: February 28, 2001Date of Patent: April 23, 2002Assignee: BASF CorporationInventors: Andrew J. McNabb, Karen A. Lewno, R. Merritt Sink
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Patent number: 6300521Abstract: 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: GrantFiled: June 21, 2000Date of Patent: October 9, 2001Assignee: BASF AktiengesellschaftInventors: Martin Jochen Klatt, Thomas Müller, Bernhard Bockstiegel
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Publication number: 20010016670Abstract: 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 10% 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: ApplicationFiled: December 14, 2000Publication date: August 23, 2001Inventors: Shuzo Murata, Nobuhiro Tani, Hiroyuki Asano
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Patent number: 6160183Abstract: A catalytic process is disclosed for oxidizing cycloalkanes directly to form, in a single step, a mixture containing the corresponding alcohol and ketone. In particular, the invention relates to oxidizing a cycloalkane by contacting it with a source of oxygen and a catalytic amount of a heterogeneous catalyst. The catalysts of the invention include gold (including gold sol-gel compounds) and sol-gel compounds containing particular combinations of Cr, Co, Zr, Ta, Si, Mg, Nb, Al and Ti, wherein certain of those metals have been combined with an oxide, such as an inorganic matrix of hydroxides or oxides, or combinations thereof. The catalysts may also optionally be supported on a suitable support member.Type: GrantFiled: February 8, 1999Date of Patent: December 12, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Joe Douglas Druliner, Norman Herron, Kostantinos Kourtakis
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Patent number: 6124505Abstract: The invention provides a catalyst for partial oxidation of hydrocarbon in the presence of a reducing compound, the catalyst comprising ultra-fine gold particles immobilized on a titanium-containing oxide, and a process for preparing an oxygen-containing organic compound, the process comprising the step of oxidizing hydrocarbon with oxygen in the presence of the above catalyst and a reducing compound.Type: GrantFiled: October 29, 1998Date of Patent: September 26, 2000Assignees: Agency of Industrial Science and Technology, Nippon Shokubai Co., Ltd.Inventors: Masatake Haruta, Yuri Angelov Kalvachev, Susumu Tsubota, Toshio Hayashi, Masahiro Wada
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Patent number: 6075169Abstract: In a process for preparing oxidation products of cyclohexane by catalytic oxidation with oxygen-containing gases in the liquid phase, where the gases are brought into contact essentially uniformly with the liquid cyclohexane in a reaction zone, liquid cyclohexane and the oxygen-containing gases are passed in countercurrent through the reaction zone.Type: GrantFiled: April 14, 1999Date of Patent: June 13, 2000Assignee: BASF AktiengesellshcaftInventors: Alwin Rehfinger, Martin Gann, Robert Markl, Rudiger Schmitt
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Patent number: 6002026Abstract: The present invention relates to novel oxidative processes for substrates such as olefins, alkanes, aromatics and alcohols using metallic porphyrin or salen catalytic complexes which have been specifically designed to maximize catalytic activity, thereby enhancing efficiency, selectively and speed of oxidation of these substrates. The choice of the substituents in the metallic complexes may be varied, but must be chosen to prevent specific ligand set arrangements known to be stable and therefore less catalytically efficient. Coordination complexes, particularly porphyrins and salens having nitrosyl axial ligands and electron-withdrawing peripheral substituents are preferred. Ruthenium coordination metals are the preferred metal center, with the highly reactive catalytic species found to be Ru.sup.III.Type: GrantFiled: December 5, 1996Date of Patent: December 14, 1999Assignee: The Trustees of Princeton UniversityInventors: John T. Groves, Tommaso Carofiglio, Marcella Bonchio, Anthony Sauve
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Patent number: 5977416Abstract: A dehydration catalyst useful for producing a monoalkylether of dihydric phenolic compound by a dehydration reaction of a dihydric phenolic compound with a lower alkyl alcohol with a high conversion at a high selectivity, comprises at least one inorganic substance of the empirical formula (I):Al.sub.a P.sub.b Ti.sub.c Si.sub.d X.sub.e O.sub.f (I)wherein X represents a member selected from the group consisting of (1) an antimony and/or a bismuth atom, and (2) a sulfur atom, a, b, c, d, e and f respectively represent the numbers of Al, P, Ti, Si, X and 0 atoms, the atomic ratio a:b is 1:1.0 to 1.9, the atomic ratio a:c is 1:0.05 to 0.5, the atomic ratio a:d is 1:0.05 to 0.2, the atomic ratio a:e is 1:0.01 to 0.3 when X represents antimony and/or bismuth atom and 1:0.004 to 0.015 when X represents a sulfur atom, and the atomic ratio a:f is 1:4.1 to 8.4.Type: GrantFiled: April 9, 1998Date of Patent: November 2, 1999Assignee: Ube Industries, Ltd.Inventors: Tokuo Matsuzaki, Tsunemi Sugimoto, Yasuo Nakamura, Takumi Manabe