Six-membered Alicyclic Ring Double Bonded Directly To The Oxime Nitrogen Patents (Class 564/267)
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Patent number: 6768013Abstract: A novel process for the direct oxidation of hydrogen and hydrocarbons is disclosed, where the explosion risks inherent in gas phase oxidations are substantially eliminated. Gaseous oxidation reactants are soluble in a first reaction solvent phase such as a perfluorocarbon (e.g. C8F18) and the oxidation product is preferentially soluble in a second product solvent phase such as water or a dilute acid. A solid catalyst such as palladium on alumina is then contacted with the dissolved reactants. The oxidation product such as hydrogen peroxide may be separated from the reaction solvent phase by extraction into the immiscible product solvent phase and then separated from it by distillation, thereby allowing re-use of the aqueous phase. The present invention may be carried out using a two-phase reaction system whereby both the reaction solvent and product solvent are contained within a reaction vessel into which the solid catalyst is slurried and mechanically agitated to promote the reaction.Type: GrantFiled: June 15, 2001Date of Patent: July 27, 2004Assignee: UOP LLCInventor: Peter R. Pujado
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Patent number: 6759556Abstract: Process for the production of cyclohexanone oxime in which a phosphate-containing aqueous reaction medium is cycled from a hydroxylammonium synthesis zone to a cyclohexanone oxime synthesis zone and back to the hydroxylammonium synthesis zone, in which hydroxylammonium synthesis zone hydroxylammonium is formed by catalytic reduction of nitrate with hydrogen, and in which cyclohexanone oxime synthesis zone hydroxylammonium is reacted with cyclohexanone to form cyclohexanone oxime, wherein the phosphate concentration in the acqueous reaction medium entering the cyclohexanone oxime synthesis zone is higher than 3.0 mol/l.Type: GrantFiled: August 28, 2003Date of Patent: July 6, 2004Assignee: DSM N.V.Inventors: Marc Blaauw, Theodorus Friederich Maria Riesthuis, Alex Pit, Henk Oevering, Antonius Jacobus Franciscus Simons
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Publication number: 20040116746Abstract: Disclosed is a method for producing a cyclic aliphatic oxime, which comprises subjecting a cyclic aliphatic primary amine to oxidation in the liquid phase under superatmospheric pressure in the presence of molecular oxygen and a solid catalyst, wherein the solid catalyst comprises an oxide of at least one metal (a) selected from the group consisting of metals belonging to Groups 5 and 6 of the Periodic Table.Type: ApplicationFiled: December 12, 2003Publication date: June 17, 2004Inventors: Mitsuji Ono, Hajime Nagahara
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Publication number: 20040116745Abstract: The invention relates to a process for the production of cyclohexanone oxime in which a phosphate-containing aqueous reaction medium is cycled from a hydroxylammonium synthesis zone to a cyclohexanone oxime synthesis zone and back to the hydroxylammonium synthesis zone, in which hydroxylammonium synthesis zone hydroxylammonium is formed by catalytic reduction of nitrate with hydrogen, and in which cyclohexanone oxime synthesis zone hydroxylammonium is reacted with cyclohexanone to form cyclohexanone oxime, the cyclohexanone and an organic solvent being fed into the cyclohexanone oxime synthesis zone, an organic medium comprising the organic solvent and cyclohexanone oxime being withdrawn from the cyclohexanone oxime synthesis zone, characterized in that the ratio fh/fc<1.Type: ApplicationFiled: January 9, 2004Publication date: June 17, 2004Inventors: Marc Blaauw, Antonius Jacobus Franciscus Simons, Henk Oevering
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Publication number: 20040077903Abstract: A method for producing cyclohexanone oxime, comprising the steps of:Type: ApplicationFiled: July 28, 2003Publication date: April 22, 2004Inventors: Ken Suzuki, Hajime Nagahara
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Publication number: 20040073064Abstract: The present invention relates to a process for preparing 2-halogenocycloalkanone oxime which comprises subjecting a 2-halogenocycloalkenone oxime compound to reduction with hydrogen in the presence of a platinum-carried catalyst.Type: ApplicationFiled: August 20, 2003Publication date: April 15, 2004Applicant: Ube Industries,Ltd.Inventors: Katzumasa Harada, Yasuhisa Fukuda, Yoshinori Yamanaka
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Patent number: 6706153Abstract: The invention relates to a process for the separation of a ketoxime or aldoxime from a ketoxime- or aldoxime-containing amide mixture in which the ketoxime or aldoxime is separated from the amide mixture by distillation. This has proved to be a very simple and direct method for separating the ketoxime and/or aldoxime from the desired amide.Type: GrantFiled: January 7, 1999Date of Patent: March 16, 2004Assignee: DSM N.V.Inventors: Yvonne H. Frentzen, Nicolaas F. Haasen, Henricus F. W. Wolters
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Publication number: 20040039230Abstract: The invention relates to a process for the production of cyclohexanone oxime in which a phosphate-containing aqueous reaction medium is cycled from a hydroxylammonium synthesis zone to a cyclohexanone oxime synthesis zone and back to the hydroxylammonium synthesis zone, in which hydroxylammonium synthesis zone hydroxylammonium is formed by catalytic reduction of nitrate with hydrogen, and in which cyclohexanone oxime synthesis zone hydroxylammonium is reacted with cyclohexanone to form cyclohexanone oxime, where the concentration hydroxylammonium in the aqueous reaction medium entering the cyclohexanone oxime synthesis zone is higher than 1.0 mol/l.Type: ApplicationFiled: September 12, 2003Publication date: February 26, 2004Inventors: Arno Benneker, Paulus Johannes Jacobus, Alex Pit, Henk Oevering
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Publication number: 20040039231Abstract: Process for the production of cyclohexanone oxime in which a phosphate-containing aqueous reaction medium is cycled from a hydroxylammonium synthesis zone to a cyclohexanone oxime synthesis zone and back to the hydroxylammonium synthesis zone, in which hydroxylammonium synthesis zone hydroxylammonium is fomed by catalytic reduction of nitrate with hydrogen, and in which cyclohexanone oxime synthesis zone hydroxylammonium is reacted with cyclohexanone to form cyclohexanone oxime, wherein the phosphate concentration in the acqueous reaction medium entering the cyclohexanone oxime synthesis zone is higher than 3.0 mol/l.Type: ApplicationFiled: August 28, 2003Publication date: February 26, 2004Inventors: Marc Blaauw, Theodorus Friederich Maria Riesthuis, Alex Pit, Henk Oevering, Antonius Jacobus Franciscus Simons
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Publication number: 20040002619Abstract: A cyclohexanone oxime is produced in a method comprising the step of reacting a cyclohexanone with a hydrogen peroxide and an ammonia in the presence of a titanium silicate and a silicon compound other than the titanium silicate. In the method, the reaction is conducted with suppressing the inactivation of the titanium silicate as a catalyst, to produce the cyclohexanone oxime with a high yield.Type: ApplicationFiled: June 10, 2003Publication date: January 1, 2004Inventors: Miyuki Oikawa, Masami Fukao
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Patent number: 6620970Abstract: The present invention relates to a process for working up an ammoximation reaction mixture, by separating a catalyst from the reaction mixture, removing the ketone oxime product, discharging the water of the reaction, and recirculating a solvent, where the ketone oxime formed is removed in a liquid phase with at least one liquid-liquid extraction in a ternary solvent system.Type: GrantFiled: September 3, 2002Date of Patent: September 16, 2003Assignee: Degussa AGInventors: Thomas Schiffer, Peter Ernst Esser, Jörg Krissmann, Martin Roos, Günter Stevermüer, Georg Friedrich Thiele
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Publication number: 20030013916Abstract: The invention relates to a purification method of cyclohexanone-oxime in a solution of solvents immiscible with water, which consists in washing said solutions with water or with an aqueous solution of a base having a pK<5 or in passing the solutions of cyclohexanone-oxime through a weakly alkaline ion exchange resin and, optionally, also through a weakly acid ion exchange resin.Type: ApplicationFiled: June 27, 2002Publication date: January 16, 2003Applicant: ENICHEM S.p.A.Inventors: Masami Fukao, Francesco Cainelli, Roberto Tessari, Piero Furlan
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Patent number: 6339042Abstract: The novel compounds of formula I: wherein Het represents an optionally substituted, optionally benzofused nitrogen containing 5- or 6-membered heteroaromatic group; R1 represents an alkyl, alkoxyalkyl or cycloalkyl group; R2 each independently represent an alkyl or alkenyl group, and m is 0 or an integer from 1 to 6, and herbicidal compositions containing such compounds as active ingredients can be utilized in various agricultural methods.Type: GrantFiled: November 29, 1999Date of Patent: January 15, 2002Assignee: American Cyanamid Co.Inventors: Trevor Newton, Helmut Siegfried Baltruschat
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Patent number: 6106803Abstract: Granulates which contain titanium silicalite-1 are composed of silicon dioxide, titanium dioxide and titanium silicalite-1 crystals. The granulates can be prepared by spray-drying or spray granulating the crystallization suspension. The granulates may be used as suspension catalysts, such as for the epoxidation of olefins using hydrogen peroxide.Type: GrantFiled: July 23, 1998Date of Patent: August 22, 2000Assignee: Degussa-Huls AGInventors: Steffen Hasenzahl, Georg Markowz, Mathias Viandt, Eckehart E. Roland, Georg Thiele, Gustaaf Goor, Alexander Moller
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Patent number: 6037378Abstract: Phenylacetic acid derivatives of the formula I ##STR1## where the substituents and the index have the following meanings: X is NOCH.sub.3, CHOCH.sub.3, CHCH.sub.3 ;Y is O, NRR.sup.1,R independently of one another are hydrogen and C.sub.1 -C.sub.4 -alkyl;R.sup.2 is cyano, nitro, trifluoromethyl, halogen, alkyl and alkoxy;m is 0, 1 or 2, it being possible for the radicals R.sup.2 to be different when m is 2;R.sup.3 is hydrogen, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.3 -C.sub.6 -cycloalkyl;R.sup.4, R.sup.5 and R.sup.6 have the meanings given in claim 1,and their salts, a process and intermediates for the preparation of these compounds, and compositions comprising them for controlling animal pests and harmful fungi.Type: GrantFiled: January 14, 1999Date of Patent: March 14, 2000Assignee: BASF AktiengesellschaftInventors: Thomas Grote, Herbert Bayer, Ruth Muller, Hubert Sauter, Reinhard Kirstgen, Volker Harries, Gisela Lorenz, Eberhard Ammermann, Siegfried Strathmann
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Patent number: 5874596Abstract: A titanosilicate catalyst and method for preparing the same, comprising primary titanosilicate particles which are combined with one another, wherein the titanosilicate catalyst comprises pores having a pore diameter of from 50 to 300 .ANG.. The inventive catalyst exhibits activity in a hydroxylation reaction of an aromatic compound, or an epoxidation reaction of an olefin, or an ammoximation reaction of a ketone using hydrogen peroxide as an oxidant.Type: GrantFiled: June 27, 1997Date of Patent: February 23, 1999Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takashi Onozawa, Osamu Kondo
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Patent number: 5736479Abstract: The invention concerns new oxidation catalysts, methods of producing them and their use. These catalysts consist of titanium silicalites crystallized in situ onto activated charcoal or metal oxides. The titanium silicalite content lies preferably in the range of 30 to 60% by wt. The atomic ratio of Si to Ti in the carrier-borne phase is 10 to 100. Such catalysts are particularly suitable for oxidation reactions with H.sub.2 O.sub.2 under mild conditions, such as temperatures of 20.degree. to 120.degree. C. and pressures equal to or higher than atmospheric.Type: GrantFiled: May 24, 1995Date of Patent: April 7, 1998Assignee: Leuna-Katalysatoren GmbHInventors: Rainer Schodel, Peter Birke, Reinhard Geyer, Peter Kraak, Willibald Muller, Hans-Dieter Neubauer, Rolf Pester, Fritz Vogt, Klaus-Peter Wendlandt
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Patent number: 5684201Abstract: Aliphatic or cycloaliphatic oximes are prepared by treating aliphatic or cycloaliphatic imines with oxygen or with an oxygen-containing gas in the presence of a catalyst.Type: GrantFiled: June 20, 1995Date of Patent: November 4, 1997Assignee: BASF AktiengesellschaftInventors: Norbert Rieber, Peter Lingelbach, Tom Witzel, Ulrich Muller
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Patent number: 5637715Abstract: A catalyst includes or consists essentially of the oxides of silicon, aluminum and titanium, characterized in that the catalyst particles are built up from a core with the composition (SiO.sub.2).sub.y (AlO.sub.2).sub.y M.sub.y, wherein x/y=10 to .infin. and M=H, Na, K, NH.sub.4, or NR.sub.4, wherein R is a C.sub.1-8 -alkyl, and a shell with the composition (SiO.sub.2).sub.n (TiO.sub.2).sub.m, wherein n/m=12 to 1000. Both the core and the shell have a crystal structure of MFI or MEL. The catalyst can be prepared by preparing a synthesis gel for the preparation of a titanium silicalite, thereafter introducing an aluminosilicata of the MFI or MEL structural type into this synthesis gel, and working up the synthesis gel in a known manner to obtain the product.Type: GrantFiled: April 3, 1995Date of Patent: June 10, 1997Assignee: Degussa AktiengesellschaftInventors: Georg Thiele, Eckehart Roland
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Patent number: 5599987Abstract: An integrated process for producing cyclohexanone oxime, a caprolactam precursor, is provided wherein isopropanol is utilized to generate the hydrogen peroxide oxidizing agent. The acetone produced as a co-product is recycled back to the secondary alcohol by hydrogenation. Ammoximation of cyclohexanone is performed in the presence of water and an alcohol other than isopropanol such as methanol or t-butyl alcohol.Type: GrantFiled: March 31, 1995Date of Patent: February 4, 1997Assignee: Arco Chemical Technology, L.P.Inventors: Guy L. Crocco, John C. Jubin, Jr., John G. Zajacek
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Patent number: 5498793Abstract: Process for the production of oximes which comprises ammoximation of a carbonylic compound selected from acetophenone and cyclododecanone with H.sub.2 O.sub.2 and NH.sub.3 in the presence of a catalyst based on silicon, titanium and oxygen and a cocatalyst consisting of amorphous silica.Type: GrantFiled: June 5, 1995Date of Patent: March 12, 1996Assignee: Enichem S.p.A.Inventors: Maria A. Mantegazza, Guido Petrini
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Patent number: 5451701Abstract: An integrated process for producing cyclohexanone oxime, a caprolactam precursor, is provided wherein a secondary alcohol is utilized to generate the hydrogen peroxide oxidizing agent and as a reaction medium for ammoximation. The ketone produced as a co-product is recycled back to the secondary alcohol by hydrogenation.Type: GrantFiled: June 27, 1994Date of Patent: September 19, 1995Assignee: Arco Chemical Technology, L.P.Inventors: John G. Zajacek, John C. Jubin, Guy L. Crocco
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Patent number: 5312987Abstract: Two-step process in the liquid phase for producing oximes at 60.degree.-100.degree. C. and 1.5-5 bars, which comprises:(a) in a primary step, ammoximating a carbonylic compound with H.sub.2 O.sub.2 and NH.sub.3 in the presence of a silicon, titanium and oxygen based catalyst;(b) oximating the residual carbonylic compound with a solution of hydroxylamine, obtained in its turn by oxidizing ammonia with H.sub.2 O.sub.2, having a concentration comprised within the range of from 0.01 to 3%, preferably of from 0.5 to 2% by weight, in such a way as to have a molar ratio of hydroxylamine to the carbonylic compound comprised within the range of from 0.9 to 3, preferably of from 1 to 2.Type: GrantFiled: March 30, 1993Date of Patent: May 17, 1994Assignee: Enichem Anic S.r.l.Inventors: Maria A. Mantegazza, Guido Petrini, Alberto Cesana
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Patent number: 5266726Abstract: Sterically hindered oximes provide polyolefin compositions, including those also containing a phenolic antioxidant, with improved resistance to discoloration during processing at elevated temperatures.Type: GrantFiled: May 8, 1992Date of Patent: November 30, 1993Assignee: Ciba-Geigy CorporationInventors: Stephen D. Pastor, Paul A. Odorisio
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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: 5227525Abstract: A multistep process for the liquid phase ammoximation of carbonyl compounds with H.sub.2 O.sub.2 and NH.sub.3, at 60.degree.-100.degree. C., at 1.5-5 bar and in the presence of a catalyst based on silicon, titanium and oxygen, characterized in that:a) in one or more primary steps, the H.sub.2 O.sub.2 : carbonyl compound molar ratio ranges from 0.9 to 1.15 by mols and the carbonyl component conversion is carried out up to at least 95%;b) in a last (exhaustion) step the H.sub.2 O.sub.2 : carbonyl compound ratio is in a higher range, i.e. from 1.5 to 3.0 by mols.Type: GrantFiled: January 21, 1992Date of Patent: July 13, 1993Assignee: Enichem Anic s.r.l.Inventors: Sergio Tonti, Paolo Roffia, Vittorio Gervasutti
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Patent number: 5130487Abstract: The invention relates to novel racemic or optically active aminopropanol derivatives of formula I ##STR1## wherein R and R.sup.1 are independently hydrogen atom, halogen atom, lower alkoxy, or together represent a methylene dioxy group,R.sup.2 and R.sup.3 together represent a chemical bond or independently stand for a hydrogen atom,R.sup.4 and R.sup.5 are independently hydrogen atom, C.sub.3-7 cycloalkyl group or straight or branched, saturated or unsaturated C.sub.1-12 alkyl group optionally substituted by one or more dialkylaminoalkyl, dimethoxyphenyl or phenyl groups, orR.sup.4 and R.sup.5 together with the adjacent nitrogen atom form a 4 to 7 membered ring optionally comprising an oxygen, sulfur or a further nitrogen atom, which ring is optionally substituted by a phenyl, benzyl or C.sub.1-3 alkyl group and the said substituents may carry a hydroxyl group, one or two methoxy groups, halogen atoms or trifluoromethyl groups, orR.sup.4 and R.sup.Type: GrantFiled: August 27, 1991Date of Patent: July 14, 1992Assignee: EGIS GyogyszergyarInventors: Zoltan Budai, Tibor Mezei, Klara Reiter nee Esses, Eniko Sziri neKiszelly, Gizella Zsila, Gabor Gigler, Lujza Petocz, Maria Szecsey nee Hegedus, Marton Fekete, Valeria Hoffmann, Laszlo Kapolnai
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Patent number: 5124138Abstract: A process for working up aqueous mother liquors containing hydrochloric acid, sulfuric acid and their hydroxylammonium and ammonium salts, entails the mother liquors being intimately mixed with an excess of cyclohexanone based on the content of hydroxylammonium salts, while maintaining a pH of from 3 to 5.5 by adding alkali metal hydroxide solutions, and the cyclohexanone phase which contains cyclohexanone oxime being removed and washed with water until essentially free of chloride.Type: GrantFiled: December 20, 1990Date of Patent: June 23, 1992Assignee: BASF AktiengesellschaftInventors: Hugo Fuchs, Gerald Neubauer, Josef Ritz
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Patent number: 5041652Abstract: The present invention relates to a method of preparing a catalyst for the ammoximation of carboxylic compounds, consisting of a synthetic, crystaline and porous material based on silicon and titanium oxides, characterized in that a preformed matrix of amorphous silica is impregnated with an aqueous solution, containing a titanium compound and an organic compound of nitrogen, as a templating agent, and that to the thus impregnated material a zeolitic structure is given by means of a hydrothermal synthesis of usual type, shape and size of the matrix being substantially maintained unchanged.Type: GrantFiled: September 17, 1990Date of Patent: August 20, 1991Assignee: Montedipe S.p.A.Inventors: Mario Padovan, Giordano De Alberti, Paolo Roffia
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Patent number: 5026911Abstract: The invention relates to a process for preparing oximes starting from saturated primary (cyclo)aliphatic amines optionally substituted by groups which are inert under the reaction conditions, by reacting the saturated primary amine with oxygen, the reaction being conducted in the liquid phase in the presence of at least a catalyst based on compounds belonging to Group IV B of the Periodic System, thereby obtaining the corresponding aliphatic and cycloaliphatic oximes.Type: GrantFiled: April 25, 1990Date of Patent: June 25, 1991Assignee: Istituto Guido Donegani S.p.A.Inventors: Carlo Venturello, Rino D'Aloisio
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Patent number: 4968842Abstract: The invention concerns a catalytic process for the manufacture of oximes by ammoximation of the corresponding carbonyl compounds, characterized in that the catalyst is a solid composition consisting of silicon, titanium and oxygen, chemically combined with each other, and in that the titanium amount, expressed as TiO.sub.2, ranges from 1 to 95% by weight, the XR diffractogam of said composition being a smooth-trend line (halo), typical of the amorphous solids.Type: GrantFiled: September 15, 1989Date of Patent: November 6, 1990Assignee: Montedipe, S.p.A.Inventors: Mario Padovan, Fausto Genoni, Giuseppe Leofanti, Guido Petrini, Paolo Roffia, Alberto Cesana
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Patent number: 4931592Abstract: The storability of molten cyclohexanone oxime containing 0.5-15% by weight of cyclohexanone and 1-8% by weight of aqueous ammonium bisulfate solution is improved by washing the molten cyclohexanone oxime with a 10-42% strength by weight aqueous ammonium sulfate solution and maintaining a pH of 4.5-5.8.Type: GrantFiled: October 31, 1989Date of Patent: June 5, 1990Assignee: BASF AktiengesellschaftInventors: Hugo Fuchs, David Agab, Gerald Neubauer, Josef Ritz
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Patent number: 4929756Abstract: A process for preparing an oxime, which comprises reacting a ketone or an aldehyde with nitrogen monoxide and hydrogen in the presence of a platinum group metal catalyst to form the corresponding oxime.Type: GrantFiled: June 1, 1989Date of Patent: May 29, 1990Assignee: Mitsubishi Kasei CorporationInventor: Kiyoji Kuma
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Patent number: 4906768Abstract: A process for producing an oxime derivative, which comprises protecting the hydroxyimino group of an oxime compound with a protecting agent, subjecting the protected oxime compound to a given reaction, and thereafter deprotecting the reaction product, wherein a 2-alkenylating agent is used as the protecting agent.Type: GrantFiled: February 11, 1988Date of Patent: March 6, 1990Assignee: Nippon Zeon Co., Ltd.Inventors: Toshiro Yamada, Jiro Tsuji, Kuniaki Goto
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Patent number: 4894478Abstract: The invention relates to a process of producing ketoximes, characterized in that a secondary alcohol, corresponding to the desired ketoxime, is partially oxidated in the liquid phase with O.sub.2, an oxidated mixture being thereby formed, which contains an excess of unreacted alcohol, the ketone corresponding to said alcohol, and H.sub.2 O.sub.2, and that said oxidated mixture is directly reacted with NH.sub.3 in the liquid phase (without isolating the alcohol, the ketone and H.sub.2 O.sub.2) in the presence of an ammoximation catalyst.Type: GrantFiled: July 25, 1988Date of Patent: January 16, 1990Assignee: Montedipe S.p.A.Inventors: Paolo Roffia, Giuseppe Paparatto, Alberto Cesana, Giorgio Tauszik
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Patent number: 4794198Abstract: The invention concerns a catalytic process for the manufacture of oximes by reaction, in the liquid phase, of the corresponding carbonylic compounds with NH.sub.3 and H.sub.2 O.sub.2, in which process the catalyst is substantially consisting of a crystalline material with a zeolitic structure containing silicon and titanium, subjected, before use, to an activating treatment with H.sub.2 O.sub.2.Type: GrantFiled: June 8, 1987Date of Patent: December 27, 1988Assignee: Montedipe S.p.A.Inventors: Paolo Roffia, Mario Padovan, Giuseppe Leofanti, Maria A. Mantegazza, Giordano De Alberti, Giorgio R. Tauszik
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Patent number: 4792616Abstract: Novel diaryl ethers of the formula ##STR1## wherein A is CR.sup.3 or N and R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, n and R.sup.6 are as defined hereinafter, processes for their preparation, herbicidal compositions which contain these compounds as the active ingredient as well as the use of these compounds or compositions for the control of weeds is disclosed.Type: GrantFiled: April 17, 1986Date of Patent: December 20, 1988Assignee: Hoffmann-La Roche Inc.Inventors: Paul Winternitz, Ren/e/ Zurfl/u/ h
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Patent number: 4745221Abstract: A catalytic process for preparing cyclohexanone-oxime, by reacting cyclohexanone with NH.sub.3 and H.sub.2 O.sub.2 in the liquid phase, characterized in that the catalyst substantially consists of a highly crystalline substance, containing SiO.sub.2 and having a zeolitic structure.Type: GrantFiled: July 7, 1986Date of Patent: May 17, 1988Assignee: Montedipe S.p.A.Inventors: Paolo Roffia, Mario Padovan, Enrico Moretti, Giordano De Alberti
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Patent number: 4714605Abstract: Technetium-99m labeled dioxime complexes are useful for imaging the myocardium, brain and hepatobiliary system, in humans and other mammalian species.Type: GrantFiled: October 14, 1986Date of Patent: December 22, 1987Assignee: E. R. Squibb & Sons, Inc.Inventors: Thomas A. Feld, Pedro N. Juri, Elizabeth N. Treher
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Patent number: 4654169Abstract: The invention concerns the novel odorants 2,2,4-trimethyl-1-phenyl-3-pentanone oxime, 2,4,4-trimethyl-5-phenyl-3-hexanone oxime and 2,4,4-trimethyl-5-phenyl-3-heptanone oxime, a process for making same, odorant compositions containing same and methods for preparing improved odorant compositions using same.Type: GrantFiled: January 27, 1986Date of Patent: March 31, 1987Assignee: Givaudan CorporationInventor: Paul A. Ochsner
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Patent number: 4560797Abstract: Improved processes for the conversion to oximes by selective oxidation, in the vapor phase, of saturated primary aliphatic or alicyclic amines having 2 to 12 carbon atoms especially cyclohexylamine to cyclohexanone oxime with elemental oxygen, in a reaction zone, in the presence of an effective amount of a catalyst comprising an oxygen-containing tungsten compound and alumina by (1) periodically regenerating the oxygen-containing tungsten catalyst by heating same at about 250.degree. C.-300.degree. C. in the presence of elemental oxygen, or (2) maintaining the temperature of the oxygen-containing tungsten catalyst in a range of about 100.degree. C.-145.degree. C. or (3) employing higher mol fractions of oxygen and of amine in a range of about 0.2-0.4 in the vapor phase are disclosed. An improved method of preparing an oxygen-containing tungsten on an alumina catalyst is also disclosed.Type: GrantFiled: December 20, 1982Date of Patent: December 24, 1985Assignee: Allied CorporationInventors: Jean Yamanis, Emery J. Carlson, John N. Armor
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Patent number: 4517382Abstract: 1-Formyl-2,6,6-trimethyl-cyclohex-1-ene derivatives of the formula I ##STR1## where R is --H or --CH.sub.3 and A is O or NOH are prepared by nitrosylating the corresponding 1-formyl-2,6,6-trimethyl-cyclohex-1-ene or -cyclohex-2-ene and, where appropriate, hydrolyzing the resulting oxime (where A is NOH) to the corresponding ketone (where A is O).The compounds I, except where R is H and A is O, are novel.Type: GrantFiled: September 16, 1982Date of Patent: May 14, 1985Assignee: BASF AktiengesellschaftInventors: Lothar Janitschke, Werner Hoffmann
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Patent number: 4504681Abstract: A process for the production of oximes which comprises contacting, in the vapor phase, a primary saturated aliphatic or alicyclic amine of 2 to 12 carbon atoms with an elemental oxygen gas in the presence of an effective amount of a catalyst comprising an alumina or oxygen-containing tungsten substance on a metal oxide support using temperatures between about 130.degree. and 230.degree. C. at atmospheric pressure is disclosed. Preferred alumina catalysts are alumina xerogels, .gamma.-alumina and acidic, fluorinated alumina. Preferred oxygen-containing tungsten catalysts are WO.sub.3 on .gamma.-alumina or WO.sub.3 on alumina xerogels.Type: GrantFiled: December 20, 1982Date of Patent: March 12, 1985Assignee: Allied CorporationInventor: John N. Armor
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Patent number: 4408077Abstract: A process and intermediates for preparing 6-(lower alkoxy)-5-(trifluoromethyl)-1-naphthalenecarboxylic acid derivatives are disclosed. The derivatives are useful for preparing aldose reductase inhibitors. With reference to the process, 1,1,1-trifluoro-5-(2-methylphenyl)-2,3-pentadione 3-oxime is cyclized to give a key intermediate 3,4-dihydro-1-hydroxy-5-methyl-1-(trifluoromethyl)-2(1H)-naphthalenone oxime; and 3,4-dihydro-1-hydroxy-5-methyl-1-(trifluoromethyl)-2(1H)-naphthalenone is aromatized to 5-methyl-1-(trifluoromethyl)-2-naphthalenol with a dehydrating agent.Type: GrantFiled: November 13, 1981Date of Patent: October 4, 1983Assignee: Ayerst, McKeena & Harrison, Inc.Inventors: Kazimir Sestanj, Steven Fung, Nedumparambil A. Abraham, Francesco Bellini
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Patent number: 4395413Abstract: The invention relates to novel oxime ethers of the general formula /I/ and acid addition salts and quaternary ammonium derivatives thereof, ##STR1## wherein A represents a C.sub.2-6 straight or branched alkylene chain,R and R.sup.1 each represent a C.sub.1-6 alkyl group or they form together with the adjacent nitrogen atom a heterocyclic ring containing 4 to 7 carbon atoms and optionally a further hetero atom, i.e. an oxygen, sulfur or nitrogen atom, and said ring may be optionally substituted by a C.sub.1-3 alkyl, phenyl or benzyl group,R.sup.2 and R.sup.3 each denote a hydrogen atom or together form a valency bond,R.sup.4 denotes a C.sub.1-10 alkyl or C.sub.2-10 alkenyl group, andn denotes an integer from 3 to 7.The compounds of the general formula /I/ are prepared according to the invention by reacting a cycloalkane derivative of the general formula /II/ ##STR2## wherein R.sup.2, R.sup.3, R.sup.4 and n have the same meaning as above, whereasY denotes an oxygen or sulphur atom or a .dbd.Type: GrantFiled: June 24, 1980Date of Patent: July 26, 1983Assignee: Egyt Gyogyszervegyeszeti GyarInventors: Zoltan Budai, Aranka Lay nee Konya, Tibor Mezei, Lujza Petocz, Katalin Grasser, Ibolya Kosoczky, Eniko Szirt nee Kiszelly, Peter Gorog
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Patent number: 4337358Abstract: Primary saturated aliphatic and alicyclic amines are oxidized by elemented oxygen to oximes, especially cyclohexylamine to cyclohexanone oxime, in vapor phase using silica gel catalyst; preferably using concentrations by volume such as 1% to 5% of amine and 5% to 30% of oxygen, and using temperatures between about 120.degree. C. and 250.degree. C. at atmospheric pressure.Type: GrantFiled: April 13, 1981Date of Patent: June 29, 1982Assignee: Allied CorporationInventor: John N. Armor
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Patent number: 4281194Abstract: An amorphous silica/alumina gel catalyst obtained by coprecipitating orthosilicate tetraester and aluminate triester in about 2.5:1 mole ratio, via rapid addition of about 0.4 to 5 moles of water per molecular equivalent of total ester groups, and drying at not over about 275.degree. C. is an effective catalyst for vapor phase reaction of cyclohexanone, ammonia and oxygen to form cyclohexanone oxime. This oxime can be rearranged to caprolactam, the starting material for nylon-6.Type: GrantFiled: February 28, 1980Date of Patent: July 28, 1981Assignee: Allied Chemical CorporationInventors: John N. Armor, Emery J. Carlson
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Patent number: 4256668Abstract: An organic, substantially water-insoluble oxime product is recovered from the liquid reaction mixture of water, ammonium sulfate and the oxime product. First the reaction mixture is separated into a first liquid layer containing an aqueous ammonium sulfate solution and a second liquid layer containing an emulsion of the oxime product as the continuous phase and aqueous ammonium sulfate as the discontinuous phase. These layers are separated and the second liquid layer is contacted with solid ammonium sulfate for a time sufficient to agglomerate the discontinuous phase. The agglomerated discontinuous phase is then removed from the continuous phase. Thereafter, either a lites fraction can be distilled from the continuous phase or the oxime product can be distilled from the continuous phase, or both. The process is particularly applicable to the production of oximes such as Aldicarb oxime, cyclohexanone oxime and methylethylketoxime from aqueous reaction mixtures in which by-product ammonium sulfate is formed.Type: GrantFiled: June 20, 1979Date of Patent: March 17, 1981Assignee: Allied Chemical CorporationInventors: Chempolil T. Mathew, Donald Pickens
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Patent number: 4242277Abstract: In the process of subjecting a compound selected from phenols, N,N-dialkylanilines and mixtures thereof to nitrosation reaction conditions using a nitrite in an aqueous system to prepare nitrosated products selected from benzoquinone oximes and p-nitroso-N,N-dialkylanilines, the nitrosation reaction is advantageously carried out in the presence of an acid stronger than nitrous acid an organic acid of pKa 2 to pKa 5 or a salt thereof and water, the quantities of the organic acid and water being up to 5 times by mole and up to 10 times by weight the quantity of the compound to be nitrosated, respectively.Type: GrantFiled: May 30, 1979Date of Patent: December 30, 1980Assignee: Mitsubishi Petrochemical Company, LimitedInventors: Morihisa Tanaka, Kazuhiko Konno, Norio Sasaki, Kunio Uchimura