Oxidation Of Organic Compound Utilizing Gaseous Oxygen Patents (Class 568/389)
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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: 6689918Abstract: A method for producing &agr;-dicarbonyl compounds of formula (I): wherein R1 and R2, independently of each other, mean C1-6-alkyl. In the method, an &agr;,&bgr;-unsaturated ketone of formula (II): wherein R1 and R2 have the meaning above and R3 and R4, independently of each other, mean hydrogen, C1-6-alkyl or di-C1-6-alkylamino, is reacted with ozone in the absence of a catalyst and the resultant ozonide is treated reductively.Type: GrantFiled: November 19, 2002Date of Patent: February 10, 2004Assignee: Lonza AGInventors: Uta Glufke, Paul Hanselmann
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Patent number: 6657087Abstract: The present invention claims a process and an apparatus for the work-up by distillation of cleavage product mixtures produced in the cleavage of alkylaryl hydroperoxides. Usually, in the work-up by distillation of cleavage product mixtures which are produced in the cleavage of alkylaryl hydroperoxides, the cleavage product mixture is divided into three main fractions, for which at least two distillation columns are used. The use of two distillation columns has the disadvantage that the capital costs, and also the energy costs, in these conventional processes are relatively high. By means of the inventive process for the work-up by distillation of cleavage product mixtures, the equipment requirements and the energy consumption can be markedly reduced in comparison with customary plants, since the cleavage product mixture can be resolved into the three main fractions in only one apparatus.Type: GrantFiled: November 13, 2001Date of Patent: December 2, 2003Assignee: INEOS Phenol GmbH & Co. KGInventors: Markus Weber, Christoph Schwarz, Uwe Tanger, Hermann-Josef Korte, Jochen Ullrich
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Publication number: 20030055292Abstract: A method and apparatus for the production of ketones via a one-step synthesis from aldehydes. In the method of the invention, an aldehyde, a carboxylic acid, and a source of oxygen, such as water, are allowed to react in the vapor phase in a catalytic tube reactor. Asymmetrical ketones, such as methyl cyclopropyl ketone, are particularly desirable reaction products.Type: ApplicationFiled: October 17, 2001Publication date: March 20, 2003Inventors: Jack S. Warren, David R. Westphal, Steve J. Zoubek
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Patent number: 6534436Abstract: The invention relates to catalysts comprising cobalt supported on a solid silica support and, in particular, to a method for manufacturing such catalysts. The catalysts may be prepared by slurrying a silica powder or impregnating a silica particle with a solution of a cobalt compound, cobalt amine carbonate, and aging the resulting slurry or solid at elevated temperature; the cobalt amine carbonate is decomposed and precipitated as basic cobalt carbonate onto the silica support. Preferably, the catalysts have a cobalt surface area in the range of 25 to >100 m2 per gram total cobalt. The catalyst may be used in hydrogenation reactions, Fischer-Tropsch reactions and oxidation reactions.Type: GrantFiled: July 26, 2002Date of Patent: March 18, 2003Assignee: Imperial Chemical Industries PLCInventors: Cornelis M Lok, Stephen Bailey, Gavin Gray
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Patent number: 6482989Abstract: A method for oxidizing an alkane, comprising the step of oxidizing said alkane with oxygen in the presence of an aldehyde, a copper-based catalyst and a nitrogen-containing compound. This method may be used to convert alkanes to corresponding alcohols and ketone having pharmaceutical activities, etc.Type: GrantFiled: July 18, 2001Date of Patent: November 19, 2002Assignee: Osaka UniversityInventors: Shun-ichi Murahashi, Naruyoshi Komiya, Yukiko Hayashi
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Patent number: 6479705Abstract: A process for preparing a ketone, an alcohol and/or a hydroperoxide is provided by reacting a hydrocarbon with molecular oxygen in the presence of a cyclic N-hydroxyimide and a compound of a transition metal, in which an oxygen-containing gas is supplied in a reaction system and at the same time a gas containing 1 to-about 8.59, by volume of oxygen is discharged from the reaction system. This process is excellent in productivity and safety and produces the desired products at a high selectivity.Type: GrantFiled: December 14, 2000Date of Patent: November 12, 2002Assignees: Sumitomo Chemical Company, Limited, Daicel Chemical Industries, Ltd.Inventors: Shuzo Murata, Nobuhiro Tani, Hiroyuki Asano
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Patent number: 6459002Abstract: Cyclohexanone, cyclohexanol and/or cyclohexyl hydroperoxide are prepared at a high productivity by allowing cyclohexane to be in contact with an oxygen-containing gas using a catalyst comprising a cyclic N-hydroxyimide and a transition metal compound in the presence of cyclohexanone and optional cyclohexanol.Type: GrantFiled: November 26, 2001Date of Patent: October 1, 2002Assignees: Sumitomo Chemical Company, Limited, Daicel Chemical Industries, Ltd.Inventors: Shuzo Murata, Nobuhiro Tani
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Publication number: 20020120170Abstract: The present invention provides a novel process for the conversion of &agr;,&bgr;-unsaturated ketones. This invention is an improvement over existing processes in that it operates at neutral reaction conditions that prevent the formation of side reactions and that it is a single step, which proceeds with complete selectivity and gives a yield that is approximately 30% higher than the currently used processes. An example of this process is the conversion of 16-dehydroprogesterone into 17 &agr;-hydroxyprogesterone.Type: ApplicationFiled: September 14, 2001Publication date: August 29, 2002Applicant: Board of Regents The University of Texas SystemInventors: Philip D. Magnus, Andrew H. Payne
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Patent number: 6433229Abstract: Preparation of cyclic, &agr;,&bgr;-unsaturated ketones of formula II by dehydrogenation of cyclic ketones which conform to formula I in which n denotes an integer from 1 to 10, and which may be substituted, at elevated temperature in the presence of catalysts in the vapor phase, wherein the reaction is carried out in the absence of oxygen or in the presence of less than 0.5 mol of oxygen per mol of compound I at temperatures ranging from 250° to 600° C. and using catalysts having a surface area (BET) of more than 0.5 m2/g.Type: GrantFiled: September 5, 2001Date of Patent: August 13, 2002Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Rolf Pinkos
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Patent number: 6403346Abstract: Enzymatic processes can produce intermediates for manufacturing retiferol derivatives that are useful for treating or preventing hyperproliferative skin diseases and for reversing conditions associated with photodamage. These processes can use as a starting material trihydroxycyclohexane, which can be chemically modified by a process that includes an enzymatic step, typically involving lipases of EC-class 3.1.1.3 or 3.1.1.34.Type: GrantFiled: September 6, 2001Date of Patent: June 11, 2002Assignee: Basilea Pharmaceutica AGInventors: Hans Hilpert, Beat Wirz
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Patent number: 6316676Abstract: The process for the preparation of carbonyl compounds of the formula I where R1 and R2 are a hydrocarbon radical, or R1 and R2 together are an unsubstituted or substituted alkylene group, and X is ═O or two alkoxy groups, comprises oxidizing alcohols of the formula II where R1 to R2 and X are as defined above, with oxygen in the gaseous phase a) at temperatures of from 270 to 600° C. on silver coated catalysts which comprise an abrasion-resistant coating of metallic silver on a core of inert support material, or b) at temperatures of from 450 to 750° C. on silver crystals and/or copper crystals having a particle size of from 0.1 to 2.5 mm for a residence time of at most 0.1 second. Also claimed is an advantageous overall process for the preparation of &agr;-diketones, preferably diacetal, from the corresponding ketone, in particular methyl ethyl ketone, via the carbonyl compounds of the formula I where X is two alkoxy groups.Type: GrantFiled: February 28, 2001Date of Patent: November 13, 2001Assignee: BASF AktiengesellschaftInventors: Werner Aquila, Jörg Botzem, Melanie Brunner, Hartwig Fuchs, Wolfgang Krause, Klaus Pandl, Ulrich Schäfer-Lüderssen
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Patent number: 6242653Abstract: The process for the preparation of carbonyl compounds of the formula I where R1 and R2 are a hydrocarbon radical, or R1 and R2 together are an unsubstituted or substituted alkylene group, and X is=O or two alkoxy groups, comprises oxidizing alcohols of the formula II where R1 to R2 and X are as defined above, with oxygen in the gaseous phase a) at temperatures of from 270 to 600° C. on silver coated catalysts which comprise an abrasion-resistant coating of metallic silver on a core of inert support material, or b) at temperatures of from 450 to 750° C. on silver crystals and/or copper crystals having a particle size of from 0.1 to 2.5 mm for a residence time of at most 0.1 second. Also claimed is an advantageous overall process for the preparation of &agr;-diketones, preferably diacetal, from the corresponding ketone, in particular methyl ethyl ketone, via the carbonyl compounds of the formula I where X is two alkoxy groups.Type: GrantFiled: August 19, 1999Date of Patent: June 5, 2001Assignee: BASF AktiengesellschaftInventors: Werner Aquila, Jörg Botzem, Melanie Brunner, Hartwig Fuchs, Wolfgang Krause, Klaus Pandl, Ulrich Schäfer-Lüderssen
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Patent number: 6057474Abstract: Preparation process for .alpha.,.beta.-dicarbonylated compounds of formula (I) ##STR1## in which R.sub.2 =alkyl, phenyl or benzyl being able to be substituted in various ways on the cycle, or carboxylic ester, and R.sub.3 =alkyl or alkoxy or carboxylic ester in which a compound of formula (II) ##STR2## in which R.sub.1 =alkyl, or alkyl .alpha.-ketocarboxylate or carboxylic ester, and R.sub.2 and R.sub.3 have the same meanings as previously is reacted in a nitrile type solvent, with molecular oxygen in the presence of copper.sup.II nitrate or ferric chloride as catalyst, and use for obtaining ethyl .alpha.-ketobutyrate, ethyl phenyl pyruvate, ethyl pyruvate, ethyl phenylglyoxylate, butane-2,3-dione or diethyl mesoxalate.Type: GrantFiled: December 22, 1998Date of Patent: May 2, 2000Assignee: Clariant S.A.Inventors: Jean-Claude Vallejos, Nicolas Capelle, Henri Arzoumanian
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Patent number: 5886233Abstract: Described are cyclohexanone derivatives of the formula (I), a method of preparing them and intermediates used in their preparation.Type: GrantFiled: August 8, 1997Date of Patent: March 23, 1999Assignee: Schering AktiengesellschaftInventors: Andreas Steinmeyer, Gunter Neef, Gunnar Muller, Hans-Joachim Knolker
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Patent number: 5859301Abstract: An improved process for preparing alkanones and alkanols by oxidizing an alkane and/or alkene having from 3 to 30 carbon atoms to form an oxidation mixture containing alkylhydroperoxide. A basic, aqueous solution is added to the oxidation mixture so that a separate basic water phase with a pH higher than 8.5 is formed. The alkylhydroperoxide is then decomposed in the presence of a heterogeneous catalyst which contains a metal compound immobilized on a carrier material. The metal of the catalyst is selected from the group consisting of Mn, Fe, Co, Ni, and Cu. The carrier material is stable in the presence of the separate basic water phase.Type: GrantFiled: December 23, 1994Date of Patent: January 12, 1999Assignee: DSM N.V.Inventors: Ubaldus F. Kragten, Henricus A. C. Baur
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Patent number: 4980513Abstract: A process for making a hydrocarbyl vinyl ketone is disclosed. In this process a ketone having the structural formula CH.sub.3 COR, where R is lower alkyl, phenyl or C.sub.7 -C.sub.8 aralkyl, is reacted with methanol in an oxygen-containing atmosphere in the presence of a catalyst system comprising a catalytically effective amount of iron on an inert support. In another preferred embodiment, the catalyst system comprises a catalytically effective amount of a precious metal selected from the group consisting of silver and gold, in addition to iron, supported on an inert material.Type: GrantFiled: January 4, 1990Date of Patent: December 25, 1990Assignee: Quantum Chemical CorporationInventors: Thomas S. Brima, Ronnie M. Hanes
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Patent number: 4487962Abstract: An oxidation catalyst wherein the catalytically active component has the general formulaMo.sub.12 P.sub.a Rh.sub.b Cu.sub.c V.sub.d Cs.sub.e X.sub.f Y.sub.g Z.sub.h O.sub.x,where X is Cr and/or Fe, Y is Nb, Z is Na, Li, K and/or Rb, a is 0.1-4, b is 0.001-1, c is 0.05-2, d is 0.05-4, e is 0.1-5, f is 0-2, g is 0-3 and h is 0-2, and x is the number of oxygen atoms required to saturate the valencies of the other constituents, is very suitable for the preparation of methacrylic acid by gas phase oxidation of methacrolein with an oxygen-containing and steam-containing gas mixture.Type: GrantFiled: September 27, 1982Date of Patent: December 11, 1984Assignee: BASF AktiengesellschaftInventors: Richard Krabetz, Franz Merger, Matthias Schwarzmann
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Patent number: 4433167Abstract: A catalyst comprising (1) palladium, (2) phosphorus, (3) antimony, (4) X and (5) oxygen wherein X denotes at least one element selected from the group consisting of potassium, sodium, rubidium, lithium, cerium, beryllium, magnesium, calcium, vanadium, strontium, zinc, thorium and rhenium.There is also provided a process for the manufacture of methacrylic or acrylic acid by oxidizing methacrolein or acrolein with molecular oxygen in the vapor phase in the presence of the catalyst defined above.Type: GrantFiled: March 4, 1982Date of Patent: February 21, 1984Assignee: Nippon Kayaku Kabushiki KaishaInventors: Masanobu Ogawa, Toshitake Kojima
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Patent number: 4350829Abstract: There is disclosed a process for the production of isobutyric acid by liquid-phase oxidation of isobutyraldehyde in the presence of an alkali metal-containing compound, the oxidation being effected while maintaining the molar ratio of oxygen to isobutyraldehyde to be fed at 0.5 or above.Type: GrantFiled: June 27, 1979Date of Patent: September 21, 1982Assignee: Mitsubishi Chemical Industries, LimitedInventors: Tatsuo Masuko, Shigeo Fukaya, Nobuyuki Murai, Jun Noma
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Patent number: 4250119Abstract: Isobutyraldehyde is produced by the oxo process and converted to acetone in the gas phase by oxidative decarbonylation on a zinc oxide supported copper oxide catalyst. The conversion is improved by adding about 2.5 to 25 percent by weight graphite to the catalyst, based on the total weight of catalyst.Type: GrantFiled: August 7, 1978Date of Patent: February 10, 1981Assignee: Chemische Werke Huls AktiengesellschaftInventors: Helmut Scharf, Gerhard Franz, HoGunther