Organic Hydroxy Containing Reactant Patents (Class 568/471)
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Publication number: 20040133045Abstract: A catalyst particle containing an active metal and a carrier composed of a carbon material, wherein the active metal being supported by cavities on a surface of the carrier and their edge portions. The active metal is fixedly attached to the carrier for a long period of time, so that the catalyst particle stably shows a high catalytic activity, which is hardly reduced by a reaction. The catalyst particle is usable for the dehydrogenation of alcohols.Type: ApplicationFiled: August 26, 2003Publication date: July 8, 2004Inventors: Hitoshi Okanobori, Atsushi Kamachi
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Patent number: 6750371Abstract: An alcohol is oxidized to an aldehyde or a ketone in the presence of a nitroxyl compound as catalyst, wherein the alcohol to be oxidized is contained in an organic liquid phase, and is reacted in the presence of a nitroxyl compound with an aqueous phase comprising an oxidant. The reaction is carried out continuously at a contact time of the phases of from 0.1 s to a maximum of 15 minutes, with intensive mixing of the phases. The process produces high yields with low quantities of other oxidation byproducts.Type: GrantFiled: October 4, 2002Date of Patent: June 15, 2004Assignee: Consortium fuer elektrochemische Industrie GmbHInventors: Elke Fritz-Langhals, Juergen Stohrer, Hermann Petersen
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Publication number: 20040064000Abstract: The present invention relates to the field of organic synthesis and more precisely to a process for the synthesis of an unsaturated aldehyde or ketone by oxidation of the corresponding alcohol. The oxidation is performed by a hypochlorite salt and a catalytic amount of a N-(2,2,6,6-tetraalkyl-4-piperidinyl-N-oxyl)-2-amino-1,3,5-triazine compound, preferably a N-oxyl derivative of one of the polymers known under the trademark Chimassorb® 944 or 2020.Type: ApplicationFiled: September 22, 2003Publication date: April 1, 2004Inventor: Eric Walther
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Publication number: 20040006247Abstract: 3,3-Dimethylbutanal is prepared from 3,3-dimethylbutanol. Intermediate 3,3-dimethylbutanol is obtained by reacting ethylene, isopropylene and a mineral acid to produce a 3,3-dimethylbutyl ester which is hydrolyzed to the alcohol. The hydrolysis step is effectively carried out by reactive distillation. Alternatively, 3,3-dimethylbutanal is prepared from 3,3-dimethylbutanol obtained by reduction of the corresponding carboxylic acid or 1,2-epoxy-3,3-dimethylbutane, or by hydrolysis of 1-halo-3,3-dimethylbutane. Fixed bed gas phase and stirred tank liquid phase processes are provided for converting 3,3-dimethylbutanol to 3,3-dimethylbutanal by catalytic dehydrogenation.Type: ApplicationFiled: March 27, 2003Publication date: January 8, 2004Applicant: The Nutrasweet CompanyInventors: Jerry R. Ebner, Zhi Guo, Arnold Hershman, Loraine M. Klein, William D. McGhee, Mark D. Paster, Indra Prakash
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Publication number: 20040002620Abstract: A process for making aldehydes involving: (a) providing a fatty alcohol; (b) providing an oxidic copper/zinc catalyst; and (c) continuously dehydrogenating the fatty alcohol, in the presence of the oxidic copper/zinc catalyst, at a temperature of from about 200 to 280° C. and a pressure of from about 10 mbar to 1 bar.Type: ApplicationFiled: July 11, 2003Publication date: January 1, 2004Inventors: Albrecht Schwerin, Gerrit Pelzer, Lothar Friesenhagen, Bernhard Gutsche
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Patent number: 6624332Abstract: The method of the present invention involves the in situ formation of metal-molybdate catalyst particles active for methanol oxidation to formaldehyde, with iron as an example, the catalyst is made by mixing particulate forms of Fe2O3 and MoO3 which form an active Fe2(MoO4)3/MoO3 component inside the reactor during methanol oxidation.Type: GrantFiled: October 31, 2001Date of Patent: September 23, 2003Assignee: Lehigh UniversityInventors: Israel E. Wachs, Laura E. Briand
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Publication number: 20030176733Abstract: The invention relates to a method for oxidizing substrates such as hydrocarbons, waxes or soot. The method involves the use of a compound of formula (I) in which: R1 and R2 represent H, an aliphatic or aromatic alkoxy radical, carboxyl radical, alkoxycarbonyl radical or hydrocarbon radical, each having 1 to 20 hydrocarbon atoms, SO3H, NH2, OH, F, Cl, Br, I and/or NO2, whereby R1 and R2 designate identical or different radicals or R1 and R2 can be linked to one another via a covalent bonding; Q1 and Q2 represent C, CH, N, CR5, each being the same or different; X and Z represent C, S, CH2, each being the same or different; Y represents O and OH; k=0, 1, 2; l=0, 1, 2; m=1 to 3, and; R5 represents one of the meanings of R1. Said compound is used as a catalyst in the presence of a radical initiator, whereby the molar ratio of the catalyst to the hydrocarbon is less than 10 mol %. Peroxy compounds or azo compounds can be used as the radical initiator.Type: ApplicationFiled: January 15, 2003Publication date: September 18, 2003Inventors: Adolf Knhle, Mark Duda, Carsten Jost, Guido Fries, Jochen Kirchhoff, Thomas Schiffer
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Patent number: 6573409Abstract: 3,3-Dimethylbutanal is prepared from 3,3-dimethylbutanol. Intermediate 3,3-dimethylbutanol is obtained by reacting ethylene, isopropylene and sulfuric acid to produce a 3,3-dimethylbutyl ester which is hydrolyzed to the alcohol. The hvdrolysis step is effectively carried out by reactive distillation. Alternatively, 3,3-dimethylbutanal is prepared from 3,3-dimethylbutanol obtained by reduction of the corresponding carboxylic acid or 1,2-epoxy-3,3-dimethylbutane, or by hydrolysis of 1-halo-3,3-dimethylbutane. Fixed bed gas phase and stirred tank liquid phase processes are provided for converting 3,3-dimethylbutanol to 3,3-dimethylbutanal by catalytic dehydrogenation.Type: GrantFiled: May 19, 2000Date of Patent: June 3, 2003Assignee: The Nutrasweet CompanyInventors: Jerry R. Ebner, Zhi Guo, Arnold Hershman, Loraine M. Klein, William D. McGhee, Mark D. Paster, Indra Prakash
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Patent number: 6559345Abstract: A process and apparatus for oxidizing methanol in a gas stream into formaldehyde in a fixed bed reactor. The process first introduces a gas stream into a fixed bed reactor. The fixed bed reactor contains a catalyst bed having a depth, a width, a length, an inlet, an upstream region, a downstream region and an outlet. Preferably, the inlet, the upstream region, the downstream region and the outlet are provided in the order stated. A vanadia-titania catalyst is provided in the upstream region and a molybdena-titania catalyst is provided in the downstream region. The vanadia-titania catalyst in the upstream region is substantially free of MoO3 and initially (i.e., during oxidation some V2O5 may sublime and migrate to the downstream region) the molybdena-titania catalyst in the downstream region is substantially free of V2O5. Next, the gas stream is contacted with the vanadia-titania catalyst under oxidizing conditions.Type: GrantFiled: September 13, 2001Date of Patent: May 6, 2003Assignee: Leigh UniversityInventor: Israel E. Wachs
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Patent number: 6552233Abstract: A process and a catalyst reaction zone comprising one or more fixed bed reactors for oxidizing methanol in a reactant gas feed stream to formaldehyde. According to one embodiment, the process comprises introducing the reactant gas feed stream into an upstream region containing a vanadia-titania first catalyst (substantially free of a volatile MoO3 species) under oxidizing conditions to form a partially oxidized reactant gas feed stream which is then introduced under oxidizing conditions into a downstream region containing a metal molybdate second catalyst to further oxidize any residual methanol contained therein. According to another embodiment, a fixed bed reactor comprising an upstream region and a downstream region containing the aforementioned vanadia-titania and metal molybdate catalysts, respectively, is utilized to implement the inventive process to yield a product gas stream containing formaldehyde preferably at a conversion of 85% or more and a selectivity of 90% or more.Type: GrantFiled: September 13, 2001Date of Patent: April 22, 2003Assignees: Lehigh University, Georgia-Pacific Resings, Inc.Inventors: Israel E. Wachs, Ray P. Bourne
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Publication number: 20030060656Abstract: This invention provides methods and catalyst systems for catalyzing enantioselective oxidation reactions, including cyclization reactions and enantioselective oxidation reactions of secondary alcohols and other similarly reactive organic substrates. Use of the methods and catalyst systems for kinetic resolution of racemic mixtures of secondary alcohols is also described.Type: ApplicationFiled: March 4, 2002Publication date: March 27, 2003Inventors: Eric M. Ferreira, Brian M. Stoltz
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Publication number: 20030055271Abstract: Alcohols are catalytically oxidized to aldehydes, in particular to benzaldehyde and diformylfuran, which are useful as intermediates for a multiplicity of purposes. The invention also relates to the polymerization of the dialdehyde and to the decarbonylation of the dialdehyde to furan.Type: ApplicationFiled: August 14, 2002Publication date: March 20, 2003Inventors: Vladimir Grushin, Walter Partenheimer, Leo E. Manzer
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Patent number: 6531635Abstract: Processes for the preparation of 3-alkoxyalkanols useful as solvents for coating materials, photoresists, or the like.Type: GrantFiled: November 19, 2001Date of Patent: March 11, 2003Assignee: Idemitsu Petrochemicals Co., Ltd.Inventors: Toshihide Yoshitome, Hiroshi Kawasaki, Naoya Kawano
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Patent number: 6512144Abstract: Processes for oxidizing hydrocarbons using a new family of crystalline manganese phosphate compositions have been developed. These compositions have an extended network which network can be a one-, two-, or three-dimensional network. The composition has an empirical formula of: (Aa+)v(Mnb+)(Mc+)xPyOz where A is a structure directing agent such as an alkali metal, M is a metal such as Al, Fe3+ and “b” is the average manganese oxidation state and varies from greater than 2.0 to a maximum of 3.0. Specific oxidation processes are oxidative dehydrodimerization and oxidative dehydrogenation.Type: GrantFiled: December 1, 2000Date of Patent: January 28, 2003Assignee: UOP LLCInventors: Gregory J. Lewis, Paula L. Bogdan, Feng Xu, Joseph A. Kocal
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Patent number: 6504055Abstract: Processes for producing citraconic anhydride and citraconic acid using porous materials with specific surface acidities and surface areas are described. The preferred catalyst is a porous gamma alumina. Itaconic acid is produced from citraconic acid. Itaconic acid is an intermediate to a variety of compounds including polymers.Type: GrantFiled: September 21, 2000Date of Patent: January 7, 2003Assignee: Board of Trustees of Michigan State UniversityInventors: Dennis J Miller, Dushyant Shekhawat, Kirthivasan Nagarajan, James E. Jackson
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Publication number: 20020198411Abstract: Allyl alcohols are converted into corresponding aldehydes or ketones in a high yield under a mild condition by using an inexpensive aluminum alkoxide as an Oppenauer oxidation catalyst and a hydride acceptor. Thus, there is provided an industrially useful method for converting allyl alcohols to corresponding aldehydes or ketones.Type: ApplicationFiled: May 21, 2002Publication date: December 26, 2002Applicant: NIKKEN CHEMICALS CO., LTD.Inventors: Shin Tanikawa, Sou Matsubayashi, Michika Tanikawa, Toshiya Komatsu
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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: 6476260Abstract: The invention relates to a method for oxidizing primary alcohols in order to obtain aldehydes and/or carboxylic acids. The reaction takes place in the presence of a catalyst supported on aluminium oxides or aluminium silicates and containing palladium, platinum, cobalt, rhodium, ruthenium, iridium, rhenium, optionally with co-catalysts.Type: GrantFiled: May 31, 2000Date of Patent: November 5, 2002Assignee: RWE-DEA Aktiengesellschraft fur Mineraloel und ChemieInventors: Albert Thomas Herrmann, Ernst Tönsen
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Publication number: 20020128506Abstract: 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 manganese-containing octahedral molecular sieve or octahedral layer. Primary alcohols are selectively oxidized to aldehydes, and secondary alcohols are selectively oxidized to ketones.Type: ApplicationFiled: August 14, 2001Publication date: September 12, 2002Inventors: Steven L. Suib, Young Chan Son, Amy R. Howell
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Patent number: 6399818Abstract: As an improvement in the process for preparing unsaturated aldehydes and unsaturated carboxylic acids through vapor-phase catalytic oxidation of at least one starting compound selected from propylene, isobutylene, t-butanol and methyl-t-butyl ether with molecular oxygen or a molecular oxygen-containing gas, using a fixed bed shell-and-tube type reactor which is filled with shaped catalysts, a process capable of effectively inhibiting occurrence of hot spots or excessive heat generation at the hot spots and producing unsaturated aldehydes and unsaturated carboxylic acids at high yields is provided.Type: GrantFiled: May 11, 2001Date of Patent: June 4, 2002Assignee: Nippon Shokubai Co. Ltd.Inventors: Michio Tanimoto, Tadashi Sento
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Patent number: 6350916Abstract: 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: GrantFiled: March 21, 2000Date of Patent: February 26, 2002Assignee: Symyx Technologies, Inc.Inventors: Anil Guram, Xiaohong Bei
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Patent number: 6350918Abstract: Preparing an aldehyde from an alcohol by contacting the alcohol in the presence of oxygen with a catalyst prepared by contacting an intimate mixture containing metal oxide support particles and particles of a catalytically active metal oxide from Groups VA, VIA, or VIIA, with a gaseous stream containing an alcohol to cause metal oxide from the discrete catalytically active metal oxide particles to migrate to the metal oxide support particles and to form a monolayer of catalytically active metal oxide on said metal oxide support particles.Type: GrantFiled: April 17, 2001Date of Patent: February 26, 2002Assignee: Lehigh UniversityInventors: Israel E. Wachs, Yeping Cai
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Publication number: 20010053865Abstract: In a process for preparing formaldehyde from methanol by dehydrogenation in a reactor in the presence of a catalyst at a temperature in the range from 300 to 1000° C., a carrier gas stream which has a temperature above the dehydrogenation temperature is fed to the reactor.Type: ApplicationFiled: July 9, 2001Publication date: December 20, 2001Applicant: Ticona GmbH, corporation of GermanyInventors: Elke Schweers, Thomas Kaiser, Michael Haubs, Michael Rosenberg
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Patent number: 6313343Abstract: Alkylene glycol is oxidized in a vapor phase in the presence of alcohol (a), oxygen, and a catalyst (a) (primary reaction). &agr;-oxoaldehyde, and alcohol (b) or olefin, are oxidized in a vapor phase in the presence of oxygen and a catalyst (b) (secondary reaction). A molar ratio of the alkylene glycol to the alcohol (a) is preferably in a range of 1/100 to 5/1. It is preferable that one same compound is used as the alcohol (a) and the alcohol (b). In the case where the primary and secondary reactions are successively executed, a reaction device in which a primary reactor and a secondary reactor are connected in a two-stage connection type is preferably used. This ensures that a method is provided that is capable of producing &agr;-oxoaldehyde at a higher yield than conventionally, and further, that is capable of stably obtaining an &agr;-oxoaldehyde solution or gas with a higher concentration than conventionally.Type: GrantFiled: January 7, 2000Date of Patent: November 6, 2001Assignee: Nippon Shokubai Co., Ltd.Inventors: Yoshitaka Arita, Akihiko Ohta, Noboru Saito, Kimio Ariyoshi
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Publication number: 20010031899Abstract: The method of the present invention involves a composition containing an intimate mixture of (a) metal oxide support particles and (b) a catalytically active metal oxide from Groups VA, VIA, or VIIA, its method of manufacture, and its method of use for converting alcohols to aldehydes. During the conversion process, catalytically active metal oxide from the discrete catalytic metal oxide particles migrates to the oxide support particles and forms a monolayer of catalytically active metal oxide on the oxide support particle to form a catalyst composition having a higher specific activity than the admixed particle composition.Type: ApplicationFiled: April 17, 2001Publication date: October 18, 2001Inventors: Israel E. Wachs, Yeping Cai
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Patent number: 6255534Abstract: Carbonyl compounds of the formula where R1 is a hydrogen atom or an alkyl radical having from 1 to 3 carbon atoms, R2 is a hydrogen atom, an unsubstituted or C1-C3-alkyl-monosubstituted to -trisubstituted C2-C4-alkenyl radical or a radical of the formula where R3 is a hydrogen atom or together with R4 is an oxygen atom, R4 is the radical OR6 or together with R3 is an oxygen atom, R5 is a hydrogen atom, an alkyl radical having from 1 to 8 carbon atoms, an unsubstituted or C1-C3-alkyl-monosubstituted to -trisubstituted C2-C4-alkenyl radical or a cyclohexyl or cyclopentyl radical and R6 is an alkyl radical having from 1 to 4 carbon atoms, a cyclohexyl or cyclopentyl radical or a radical of the formula —CH2—CHO or —CH2—CH2—O—CH2—CHO, are prepared by gas-phase oxidation of methanol or alcohols of the formula where R1 and R5 are as defined above, by means of an oxygen-containing gas in the presence of copper- and/or silvType: GrantFiled: February 1, 1999Date of Patent: July 3, 2001Assignee: BASF AktiengesellschaftInventors: Dirk Demuth, Thomas Fetzer, Volker Pratsch, Thomas Wendrich, Helmuth Menig, Ludwig Wambach, Klaus Harth
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Patent number: 6169214Abstract: A coated catalyst which consists of a hollow cylindrical carrier and a catalytically active oxide material applied to the outer surface of the carrier, the applied catalytically active oxide material being applied in a coat thickness of from 10 to 1000 &mgr;m, and having a specific catalytic surface area of from 20 to 30 m2/g and an abrasion of <10, preferably <5, particularly preferably <0.5, % by weight in the turntable abrasion test.Type: GrantFiled: March 8, 1999Date of Patent: January 2, 2001Assignee: BASF AktiengesellschaftInventors: Andreas Tenten, Peter Weidlich, Gerd Linden
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Patent number: 6166264Abstract: The oxidation catalyst system of the invention is composed of (A) a ruthenium compound and (B) a dioxybenzene or its oxidant. The ruthenium compound (A) includes dichlorotris(triphenylphosphine)ruthenium (II) and other ruthenium complexes and Ru/C. The dioxybenzene or its oxidant (B) includes hydroquinone. The oxidation of an alcohol by molecular oxygen in the presence of the oxidation catalyst system can give the corresponding carbonyl compound in high yield. A primary alcohol is more selectively oxidized than a secondary alcohol.Type: GrantFiled: September 24, 1999Date of Patent: December 26, 2000Assignee: Daicel Chemical Industries, Ltd.Inventors: Yasutaka Ishii, Tatsuya Nakano
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Patent number: 6165352Abstract: A continuous process for the dehydrogenation of a hydrocarbon and/or oxygenated hydrocarbon feed, comprising contacting the hydrocarbon and/or oxygenated hydrocarbon feed with a dehydrogenation catalyst at elevated temperature in a reaction zone characterised in that the catalyst is capable of retaining hydrogen and (a) is contacted with a feed to form a dehydrogenated product and hydrogen, at least some of the hydrogen formed being adsorbed by the catalyst and/or reacting therewith to reduce at least part of the catalyst; (b) the dehydrogenated product and any unadsorbed/unreacted hydrogen is removed from the reaction zone; (c) at least some of the adsorbed hydrogen is removed from the catalyst and/or at least some of the reduced catalyst is oxidised; and (d) reusing the catalyst from step (c) in step (a).Type: GrantFiled: March 12, 1998Date of Patent: December 26, 2000Assignee: BP Chemicals LimitedInventors: Jeremy Bernard Cooper, Jonathon Charles Frost, Stephen Roy Partington
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Patent number: 6156931Abstract: A new family of crystalline manganese phosphate compositions has been prepared. These compositions have an extended network which network can be a one-, two-, or three-dimensional network. The composition has an empirical formula of:(A.sup.3+).sub.v (Mn.sup.b+)(M.sup.c+).sub.x P.sub.y O.sub.zwhere A is a structure directing agent such as an alkali metal, M is a metal such as Al, Fe.sup.3+ and "b" is the average manganese oxidation state and varies from greater than 2.0 to a maximum of 3.0. These compositions can be used as adsorbents and as catalysts in the oxidation of hydrocarbons.Type: GrantFiled: March 24, 1999Date of Patent: December 5, 2000Assignee: UOP LLCInventor: Gregory J. Lewis
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Patent number: 6133482Abstract: In a process for preparing carbonyl compounds of the formula ##STR1## where R.sup.1 is a hydrogen atom or an alkyl radical having from 1 to 3 carbon atoms, R.sup.2 is a hydrogen atom or a radical of the formula ##STR2## where R.sup.3 is a hydrogen atom or together with R.sup.4 is an oxygen atom, R.sup.4 is the radical OR.sup.6 or together with R.sup.3 is an oxygen atom, R.sup.5 is a hydrogen atom, an alkyl radical having from 1 to 8 carbon atoms or a cyclohexyl or cyclopentyl radical and R.sup.6 is an alkyl radical having from 1 to 4 carbon atoms, a cyclohexyl or cyclopentyl radical or a radical of the formula --CH.sub.2 --CHO or --CH.sub.2 --CH.sub.2 --O--CH.sub.2 --CHO, by gas-phase oxidation of methanol or alcohols of the formula ##STR3## where R.sup.1 and R.sup.5 are as defined above and R.sup.7 is a hydrogen atom or a radical OR.sup.8 and R.sup.8 is a hydrogen atom, an alkyl radical having from 1 to 4 carbon atoms, a cyclohexyl or cyclopentyl radical or a radical for the formula --CH.sub.2 --CH.sub.Type: GrantFiled: June 16, 1999Date of Patent: October 17, 2000Assignee: BASF AktiengesellschaftInventors: Thomas Fetzer, Dirk Demuth, Heinz Rutter, Helmuth Menig, Peter Resch, Wilhelm Ruppel, Harro Wache
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Patent number: 6072087Abstract: The present invention relates to a process for the preparation of carbonyl compounds of the formula ##STR1## in which R.sup.1 denotes a hydrogen atom or an alkyl radical containing from 1 to 3 carbon atoms, R.sup.2 denotes a hydrogen atom or a radical of the formula ##STR2## in which R.sup.3 denotes a hydrogen atom or, together with R.sup.4, an oxygen atom, R.sup.4 denotes the radical OR.sup.6 or, together with R.sup.3, an oxygen atom, R.sup.5 denotes a hydrogen atom or an alkyl radical containing from 1 to 8 carbon atoms or a cyclohexyl or cyclopentyl radical, and R.sup.6 denotes an alkyl radical containing from 1 to 4 carbon atoms, a cyclohexyl or cyclopentyl radical or a radical of the formula--CH.sub.2 --CHO or --CH.sub.2 --CH.sub.2 --O--CH.sub.2 --CHO,by gas-phase oxidation of methanol or alcohols of the formula ##STR3## in which R.sup.1 and R.sup.5 have the meanings specified above and R.sup.7 denotes a hydrogen atom or a radical OR.sup.8, and R.sup.Type: GrantFiled: June 16, 1999Date of Patent: June 6, 2000Assignee: BASF AktiengesellschaftInventors: Thomas Fetzer, Dirk Demuth, Heinz Rutter, Helmuth Menig, Peter Resch, Wilhelm Ruppel, Harro Wache
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Patent number: 6013843Abstract: A process for continuous industrial production of unsaturated aliphatic aldehydes having a boiling range from 95 to 136.degree. C. by oxidative dehydrogenation of the corresponding alcohols with an oxygen-comprising gas over a supported catalyst consisting of copper, silver and/or gold on an inert support in a tube bundle reactor, rapid cooling of the reaction gases and removal of the aldehydes from the resulting condensate with recycling of the unconverted alcohols comprisesa) vaporizing the alcohol,b) admixing the alcohol vapor with an oxygen-comprising gas,c) initially passing the resulting oxygen-comprising alcohol vapor at above the dew point of the alcohol but below the commencement temperature of the reaction through a layer of one of the abovementioned supported catalysts which is at least 0.5 cm in thickness and only thend) reacting the oxygen-comprising alcohol vapor at from 300 to 600.degree. C.Type: GrantFiled: May 28, 1998Date of Patent: January 11, 2000Assignee: BASF AktiengeselllschaftInventors: Werner Aquila, Hartwig Fuchs, Otto Worz, Wilhelm Ruppel, Klaus Halbritter
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Patent number: 5990358Abstract: A process for preparing formaldehyde by oxidative dehydrogenation of methanol comprises passing a gas mixture (i) comprisinga) from 0.1 to 50% by volume of methanol,b) from 0.1 to 30% by volume of oxygen,c) from 0 to 50% by volume of nitrogen oxide andd) from 0 to 60% by volume of water at from 150 to 800.degree. C. through a phosphorus-doped silver catalyst fixed bed (a) and applying from 0.01 to 100 ppm by weight of phosphorus, based on the phosphorus-doped silver catalyst fixed bed, in the form of a finely divided phosphorus compound having a melting point or decomposition temperature of more than 500.degree. C. (phosphorus compound P) to the phosphorus-doped silver catalyst fixed bed (a) per kg of methanol which is passed through in the form of the gas mixture (i) per cm.sup.2 of the cross-sectional area of the phosphorus-doped silver catalyst fixed bed (a).Type: GrantFiled: March 13, 1998Date of Patent: November 23, 1999Assignee: BASF AktiengesellschaftInventors: Bernhard Knuth, Rainer Diercks
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Patent number: 5912388Abstract: A process for preparing an aldehyde or ketone comprising reacting a primary or secondary alcohol with oxygen in the presence of a base, a catalytic amount of a copper salt and a suitable lignad under anhydrous conditions.Type: GrantFiled: November 12, 1997Date of Patent: June 15, 1999Assignee: Zeneca LimitedInventors: Christopher John Urch, Istvan Ettienne Marko, Masao Tuskazaki, Paul Richard Giles, Stephen Martin Brown
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Patent number: 5336779Abstract: In producing formylimidazoles by catalytically oxidizing the corresponding 4- or 5-hydroxymethylimidazoles, the catalytic oxidation is carried out in the presence of a noble metal catalyst while oxygen or air is blown into the reaction system. In this case, it is particularly desirable that the catalytic oxidation in the presence of a noble metal catalyst be carried out in a solvent comprising an aqueous alkali or in a mixed solvent composed of an aqueous alkali and an organic solvent immiscible with water.Type: GrantFiled: September 23, 1993Date of Patent: August 9, 1994Assignee: Nippon Gohsei Kagaku Kogyo Kabushiki KaishaInventors: Toshio Yamamoto, Kazumasa Hirata, Shigenori Wakabayashi, Akio Katsuura
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Patent number: 5274187Abstract: A compound having a carbonyl group and/or a carboxyl group is produced by catalytically oxidizing a polyhydric alcohol having at least one primary hydroxyl group and at least one secondary hydroxyl group in the presence of a supported catalyst comprising at least one catalytic component selected from among the following components (I) to (IV) loaded on a support:(I) A first catalytic component chosen from at least one element selected from group A consisting of platinum, palladium, rhodium, ruthenium, rhenium, gold, silver and copper,(II) a combination of the first catalytic component with a second catalytic component chosen from at least one element selected from group B consisting of tin, lead, antimony, bismuth, selenium and tellurium,(III) a combination of the first catalytic component with a third catalytic component chosen from at least one element selected from group C consisting of rare earth elements, and(IV) a combination of the first catalytic component with the second catalytic component and the tType: GrantFiled: August 28, 1992Date of Patent: December 28, 1993Assignee: Kao CorporationInventors: Hiroshi Kimura, Keiichi Tsuto
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Patent number: 5252758Abstract: Process for oxidizing organic compounds with hydrogen peroxide in the presence of titanium-silicalite and of a water-alcohol solvent which, after the preliminary separation of the oxidation product and of the water formed during the reaction, is used again in order to extract hydrogen peroxide produced in a redox process with alkyl-anthraquinone and is fed again to the oxidation reaction.Type: GrantFiled: November 25, 1992Date of Patent: October 12, 1993Inventors: Mario G. Clerici, Patrizia Ingallina
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Patent number: 5245083Abstract: A catalyst is herein disclosed, which comprises a mixture of a composition (1) represented by the following general formula (1):(Mo).sub.a (Bi).sub.b (Fe).sub.c (X).sub.d (Z).sub.f (O).sub.g (1)(wherein X represents one or both of Ni and Co, Z represents at least one element selected from the group consisting of W, Be, Mg, S, Ca, Sr, Ba, Te, Se, Ce, Ge, Mn, Zn, Cr, Ag, Sb, Pb, As, B, P, Nb, Cu, Cd, Sn, Al, Zr and Ti, a, b, c, d, f and g each represents an atomic ratio of each corresponding element and if a is assumed to be 12, b ranges from 0.1 to 10, c ranges from 0 to 20, d ranges from 0 to 20 and f ranges from 0 to 4 and g is a number of oxygen atom required for satisfying the valency requirement of the foregoing elements) and a composition (2) represented by the following general formula (2):(A).sub.m (Mo).sub.n (O).sub.p (2)(wherein A represents at least one element selected from K, Rb and Cs and m, n and p each represents an atomic ratio and if m is assumed to be 2, n ranges from 1 to 9 and p is 3n+1).Type: GrantFiled: February 26, 1992Date of Patent: September 14, 1993Assignee: Mitsui Toatsu Chemicals, Inc.Inventor: Ikuya Matsuura
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Patent number: 5241122Abstract: Catalysts, catalyst precursors, and catalytic systems are provided. The catalysts generally comprise a substrate that includes a group IB metal and a porous, microcrystalline layer that includes the metal and that is disposed on at least a portion of the substrate. The catalysts are prepared by providing a substrate that includes group IB metal, oxidizing said substrate in the presence of stainless steel to produce an oxide coating of said group IB metal, and reducing substantially all of said oxidized substrate.Type: GrantFiled: March 3, 1992Date of Patent: August 31, 1993Assignee: Union Camp CorporationInventors: James B. Woell, John W. Catino
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Patent number: 5196608Abstract: The present invention relates to the use of an allylchloride of the general formula ##STR1##wherein R is a C.sub.1 -C.sub.12 alkyl group or a C.sub.2 -C.sub.12 alkenyl group, which groups may be substituted with one or more substitutents selected from the group consisting of C.sub.1 -C.sub.4 alkoxy, halogen, unsubstituted phenyl and substituted phenyl; a (trihydrocarbyl)silyl group; a (dihydrocarbyl) (hydrocarbyloxy)silyl group; or a dihydropyran-2-yl group, a tetrahydropyran-2-yl group, a dihydrofur-2-yl group or a tetrahydrofur-2-yl group, which groups may be substituted with C.sub.1 -C.sub.6 alkyl;for preparing an aldehyde compound via an intermediate alcohol compound.The invention further relates to a new allylchloride.Type: GrantFiled: December 2, 1991Date of Patent: March 23, 1993Assignee: Duphar International Research B.V.Inventors: Gerrit J. Lagerweij, Cornelis Bakker, Monique E. A. De Bruin-Van Der Flier
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Patent number: 5196609Abstract: The preparation of 3-alkoxycarbonyl propenals and 3-dialkoxymethyl propenals of the general formulae Ia and Ib respectively: ##STR1## (R.sup.1 =C.sub.1 -C.sub.3 -alkyl group; R.sup.2 and R.sup.3 =hydrogen, methyl, or ethyl; and R.sup.4 and R.sup.5 =C.sub.1 -C.sub.4 -alkyl groups, which may be joined to form a 5-membered or 6-membered ring), is effected by reacting a corresponding alcohol of the general formula IIa or IIb ##STR2## with oxygen or an oxygen-containing gas in the gas phase in the presence of a metal from Group IB of the Periodic Table or a compound of one such metal acting as catalyst.The target products serve as intermediates for the synthesis of carotenoids.Type: GrantFiled: March 2, 1992Date of Patent: March 23, 1993Assignee: BASF AktiengesellschaftInventors: Werner Aquila, Hans-Ulrich Scholz, Hartwig Fuchs, Wolfgang Krause, Joachim Paust, Werner Hoffmann
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Patent number: 5155279Abstract: A process for the preparation of an aldehyde which comprises reacting the corresponding alkanol with a solubilized stable free radical nitroxide having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R.sub.5 and R.sub.6 is alkyl, hydrogen, aryl or a substituted heteroatom, nitric acid and a solvent, in the absence of an oxidant at a temperature in the range of from about -10.degree. C. to about 60.degree. C. and thereafter separating out the aldehyde.Type: GrantFiled: October 18, 1991Date of Patent: October 13, 1992Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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Patent number: 5155280Abstract: A process for the preparation of an aldehyde which comprises reacting the corresponding alkanol with a solubilized stable free radical nitroxide having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R.sub.5 and R.sub.6 is alkyl, hydrogen, aryl or a substituted heteroatom, an alkali metal nitrosodisulfonate, a non-basic polar solvent and an oxidant, for about eight hours or less at a temperature in the range of from about 10.degree. C. to about 20.degree. C. and thereafter separating out the aldehyde.Type: GrantFiled: September 30, 1991Date of Patent: October 13, 1992Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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Patent number: 5155278Abstract: A process for the preparation of an aldehyde which comprises reacting the corresponding alkanol with a solubilized stable free radical nitroxide having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R.sub.5 and R.sub.6 is alkyl, hydrogen, aryl or a substituted heteroatom, nitric acid and a non-basic polar solvent, in the presence of an oxidant, for about eight hours or less at a temperature in the range of from about -10.degree. C. to about 25.degree. C., and thereafter separating out the aldehyde.Type: GrantFiled: September 30, 1991Date of Patent: October 13, 1992Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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Patent number: 5149884Abstract: In a tube bundle reactor for carrying out catalytic organic reactions in the gas phase, comprising reaction tubes (A) arranged between tubesheets (B), the reaction tubes have an inside diameter ranging from 0.5 to 3 cm, the ratio of reaction tube length to inside diameter ranges from 2 to 10, and the reaction tubes (A) are surrounded by a fluid heat transport medium flowing in the crosswise direction; said tube bundle reactor is useful in particular in exothermic organic reactions.Type: GrantFiled: April 1, 1991Date of Patent: September 22, 1992Assignee: BASF AktiengesellschaftInventors: Karl Brenner, Wilhelm Ruppel, Otto Woerz, Klaus Halbritter, Hans-Juergen Scheiper, Werner Aquila, Hartwig Fuchs
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Patent number: 5144090Abstract: A method for preparing acrolein or methacrolein comprises subjecting propylene, secondary propanol, isobutylene or tertiary butanol to gas phase catalytic oxidation with molecular oxygen in the presence of a catalyst represented by the following general formula (I):Mo.sub.a Bi.sub.b Fe.sub.c X.sub.d Y.sub.O Z.sub.f O.sub.g (I)wherein X represents at least one element selected from the group consisting of Ni and Co; Y represents at least one element selected from the group consisting of K, Rb, Cs and Tl; and Z represents at least one element selected from the group consisting of Be, Mg, Ca, Sr, Ba, Ce, Ti, Zr, Nb, Cr, W, Mn, Cu, Ag, Zn, Cd, B, Al, Si, Ge, Sn, Pb, P, As, Sb, S, Se and Te; a, b, c, d, e, f and g each represents an atomic ratio of the corresponding element and when a is assumed to be 12, b=0.1.about.10, c=0.1.about.20, d=2.about.20, e=0.01.about.2, f=0.about.Type: GrantFiled: June 6, 1991Date of Patent: September 1, 1992Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Tadatoshi Honda, Tokio Nagayama, Nobuhiko Horiuchi, Jun Kitagawa, Kazunori Kawahara, Masami Murakami
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Patent number: 5118868Abstract: A catalyst for the partial oxidation of an alcohol to a corresponding aldehyde. The catalyst includes a monolithic structured inert carrier and an active catalytic mixture of oxides of molybdenum and either chromium, vanadium, aluminum, iron, tungsten, manganese or mixtures thereof in a molar ratio of the molybdenum oxide to the other oxide or oxides of between 1 and 5. The catalyst has a reduced pressure drop compared to a particulate catalyst bed.Type: GrantFiled: October 12, 1990Date of Patent: June 2, 1992Assignee: Haldor Topsoe A/SInventors: Bent Sarup, Poul E. H. Nielsen, Viggo L. Hansen, Keld Johansen
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Patent number: 5026922Abstract: There is disclosed a process for preparing glycol aldehyde from ethylene glycol by use of a complex system catalyst comprising copper and other inorganic component, which comprises permitting 0.001 to 0.3 mole of oxygen per one mole of ethylene glycol to be copresent in the reaction system.Type: GrantFiled: December 22, 1989Date of Patent: June 25, 1991Assignee: Research Association for Utilization of Light OilInventors: Takatoshi Seto, Takashi Yokoi, Masaki Odagiri, Makoto Imanari
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Patent number: 4996007Abstract: The instant invention relates to a process for the oxidation of primary alcohols to aldehydes, acids and esters, particularly to aldehydes. In this process and alcohol and oxygen are contacted and reacted with a dihydrodihydroxynaphthalene or a dihydrodihydroxyanthracene in the presence of a Group VIII metal oxidation catalyst and optionally in the presence of a quaternary ammonium halide cocatalyst, and subsequently product aldehyde/acid/ester and the corresponding napthoquinone or anthraquinone are separated from the reaction mixture. The by-product naphthoquinone or anthraquinone is suitably recycled to the alcohol oxidation step by hydrogenating the naphthoquinone or anthraquinone to the corresponding dihydrodihydroxynaphthalene or dihydrodihydroxyanthracene by contacting it with hydrogen in the presence of a hydrogenation catalyst.Type: GrantFiled: January 19, 1990Date of Patent: February 26, 1991Assignee: Shell Oil CompanyInventors: Kuo-Hua Chao, Tamal K. Dutta, Lynn H. Slaugh