Six-membered Alicyclic Ring Double Bonded Directly To The Oxime Nitrogen Patents (Class 564/267)
  • Patent number: 6768013
    Abstract: 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: Grant
    Filed: June 15, 2001
    Date of Patent: July 27, 2004
    Assignee: UOP LLC
    Inventor: Peter R. Pujado
  • Patent number: 6759556
    Abstract: 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: Grant
    Filed: August 28, 2003
    Date of Patent: July 6, 2004
    Assignee: DSM N.V.
    Inventors: Marc Blaauw, Theodorus Friederich Maria Riesthuis, Alex Pit, Henk Oevering, Antonius Jacobus Franciscus Simons
  • Publication number: 20040116746
    Abstract: 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: Application
    Filed: December 12, 2003
    Publication date: June 17, 2004
    Inventors: Mitsuji Ono, Hajime Nagahara
  • Publication number: 20040116745
    Abstract: 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: Application
    Filed: January 9, 2004
    Publication date: June 17, 2004
    Inventors: Marc Blaauw, Antonius Jacobus Franciscus Simons, Henk Oevering
  • Publication number: 20040077903
    Abstract: A method for producing cyclohexanone oxime, comprising the steps of:
    Type: Application
    Filed: July 28, 2003
    Publication date: April 22, 2004
    Inventors: Ken Suzuki, Hajime Nagahara
  • Publication number: 20040073064
    Abstract: 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: Application
    Filed: August 20, 2003
    Publication date: April 15, 2004
    Applicant: Ube Industries,Ltd.
    Inventors: Katzumasa Harada, Yasuhisa Fukuda, Yoshinori Yamanaka
  • Patent number: 6706153
    Abstract: 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: Grant
    Filed: January 7, 1999
    Date of Patent: March 16, 2004
    Assignee: DSM N.V.
    Inventors: Yvonne H. Frentzen, Nicolaas F. Haasen, Henricus F. W. Wolters
  • Publication number: 20040039230
    Abstract: 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: Application
    Filed: September 12, 2003
    Publication date: February 26, 2004
    Inventors: Arno Benneker, Paulus Johannes Jacobus, Alex Pit, Henk Oevering
  • Publication number: 20040039231
    Abstract: 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: Application
    Filed: August 28, 2003
    Publication date: February 26, 2004
    Inventors: Marc Blaauw, Theodorus Friederich Maria Riesthuis, Alex Pit, Henk Oevering, Antonius Jacobus Franciscus Simons
  • Publication number: 20040002619
    Abstract: 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: Application
    Filed: June 10, 2003
    Publication date: January 1, 2004
    Inventors: Miyuki Oikawa, Masami Fukao
  • Patent number: 6620970
    Abstract: 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: Grant
    Filed: September 3, 2002
    Date of Patent: September 16, 2003
    Assignee: Degussa AG
    Inventors: Thomas Schiffer, Peter Ernst Esser, Jörg Krissmann, Martin Roos, Günter Stevermüer, Georg Friedrich Thiele
  • Publication number: 20030013916
    Abstract: 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: Application
    Filed: June 27, 2002
    Publication date: January 16, 2003
    Applicant: ENICHEM S.p.A.
    Inventors: Masami Fukao, Francesco Cainelli, Roberto Tessari, Piero Furlan
  • Patent number: 6339042
    Abstract: 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: Grant
    Filed: November 29, 1999
    Date of Patent: January 15, 2002
    Assignee: American Cyanamid Co.
    Inventors: Trevor Newton, Helmut Siegfried Baltruschat
  • Patent number: 6106803
    Abstract: 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: Grant
    Filed: July 23, 1998
    Date of Patent: August 22, 2000
    Assignee: Degussa-Huls AG
    Inventors: Steffen Hasenzahl, Georg Markowz, Mathias Viandt, Eckehart E. Roland, Georg Thiele, Gustaaf Goor, Alexander Moller
  • Patent number: 6037378
    Abstract: 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: Grant
    Filed: January 14, 1999
    Date of Patent: March 14, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Grote, Herbert Bayer, Ruth Muller, Hubert Sauter, Reinhard Kirstgen, Volker Harries, Gisela Lorenz, Eberhard Ammermann, Siegfried Strathmann
  • Patent number: 5874596
    Abstract: 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: Grant
    Filed: June 27, 1997
    Date of Patent: February 23, 1999
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takashi Onozawa, Osamu Kondo
  • Patent number: 5736479
    Abstract: 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: Grant
    Filed: May 24, 1995
    Date of Patent: April 7, 1998
    Assignee: Leuna-Katalysatoren GmbH
    Inventors: Rainer Schodel, Peter Birke, Reinhard Geyer, Peter Kraak, Willibald Muller, Hans-Dieter Neubauer, Rolf Pester, Fritz Vogt, Klaus-Peter Wendlandt
  • Patent number: 5684201
    Abstract: 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: Grant
    Filed: June 20, 1995
    Date of Patent: November 4, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Norbert Rieber, Peter Lingelbach, Tom Witzel, Ulrich Muller
  • Patent number: 5637715
    Abstract: 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: Grant
    Filed: April 3, 1995
    Date of Patent: June 10, 1997
    Assignee: Degussa Aktiengesellschaft
    Inventors: Georg Thiele, Eckehart Roland
  • Patent number: 5599987
    Abstract: 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: Grant
    Filed: March 31, 1995
    Date of Patent: February 4, 1997
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Guy L. Crocco, John C. Jubin, Jr., John G. Zajacek
  • Patent number: 5498793
    Abstract: 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: Grant
    Filed: June 5, 1995
    Date of Patent: March 12, 1996
    Assignee: Enichem S.p.A.
    Inventors: Maria A. Mantegazza, Guido Petrini
  • Patent number: 5451701
    Abstract: 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: Grant
    Filed: June 27, 1994
    Date of Patent: September 19, 1995
    Assignee: Arco Chemical Technology, L.P.
    Inventors: John G. Zajacek, John C. Jubin, Guy L. Crocco
  • Patent number: 5312987
    Abstract: 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: Grant
    Filed: March 30, 1993
    Date of Patent: May 17, 1994
    Assignee: Enichem Anic S.r.l.
    Inventors: Maria A. Mantegazza, Guido Petrini, Alberto Cesana
  • Patent number: 5266726
    Abstract: Sterically hindered oximes provide polyolefin compositions, including those also containing a phenolic antioxidant, with improved resistance to discoloration during processing at elevated temperatures.
    Type: Grant
    Filed: May 8, 1992
    Date of Patent: November 30, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Stephen D. Pastor, Paul A. Odorisio
  • Patent number: 5252758
    Abstract: 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: Grant
    Filed: November 25, 1992
    Date of Patent: October 12, 1993
    Inventors: Mario G. Clerici, Patrizia Ingallina
  • Patent number: 5227525
    Abstract: 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: Grant
    Filed: January 21, 1992
    Date of Patent: July 13, 1993
    Assignee: Enichem Anic s.r.l.
    Inventors: Sergio Tonti, Paolo Roffia, Vittorio Gervasutti
  • Patent number: 5130487
    Abstract: 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: Grant
    Filed: August 27, 1991
    Date of Patent: July 14, 1992
    Assignee: EGIS Gyogyszergyar
    Inventors: 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
  • Patent number: 5124138
    Abstract: 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: Grant
    Filed: December 20, 1990
    Date of Patent: June 23, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Hugo Fuchs, Gerald Neubauer, Josef Ritz
  • Patent number: 5041652
    Abstract: 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: Grant
    Filed: September 17, 1990
    Date of Patent: August 20, 1991
    Assignee: Montedipe S.p.A.
    Inventors: Mario Padovan, Giordano De Alberti, Paolo Roffia
  • Patent number: 5026911
    Abstract: 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: Grant
    Filed: April 25, 1990
    Date of Patent: June 25, 1991
    Assignee: Istituto Guido Donegani S.p.A.
    Inventors: Carlo Venturello, Rino D'Aloisio
  • Patent number: 4968842
    Abstract: 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: Grant
    Filed: September 15, 1989
    Date of Patent: November 6, 1990
    Assignee: Montedipe, S.p.A.
    Inventors: Mario Padovan, Fausto Genoni, Giuseppe Leofanti, Guido Petrini, Paolo Roffia, Alberto Cesana
  • Patent number: 4931592
    Abstract: 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: Grant
    Filed: October 31, 1989
    Date of Patent: June 5, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Hugo Fuchs, David Agab, Gerald Neubauer, Josef Ritz
  • Patent number: 4929756
    Abstract: 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: Grant
    Filed: June 1, 1989
    Date of Patent: May 29, 1990
    Assignee: Mitsubishi Kasei Corporation
    Inventor: Kiyoji Kuma
  • Patent number: 4906768
    Abstract: 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: Grant
    Filed: February 11, 1988
    Date of Patent: March 6, 1990
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Toshiro Yamada, Jiro Tsuji, Kuniaki Goto
  • Patent number: 4894478
    Abstract: 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: Grant
    Filed: July 25, 1988
    Date of Patent: January 16, 1990
    Assignee: Montedipe S.p.A.
    Inventors: Paolo Roffia, Giuseppe Paparatto, Alberto Cesana, Giorgio Tauszik
  • Patent number: 4794198
    Abstract: 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: Grant
    Filed: June 8, 1987
    Date of Patent: December 27, 1988
    Assignee: Montedipe S.p.A.
    Inventors: Paolo Roffia, Mario Padovan, Giuseppe Leofanti, Maria A. Mantegazza, Giordano De Alberti, Giorgio R. Tauszik
  • Patent number: 4792616
    Abstract: 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: Grant
    Filed: April 17, 1986
    Date of Patent: December 20, 1988
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Paul Winternitz, Ren/e/ Zurfl/u/ h
  • Patent number: 4745221
    Abstract: 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: Grant
    Filed: July 7, 1986
    Date of Patent: May 17, 1988
    Assignee: Montedipe S.p.A.
    Inventors: Paolo Roffia, Mario Padovan, Enrico Moretti, Giordano De Alberti
  • Patent number: 4714605
    Abstract: Technetium-99m labeled dioxime complexes are useful for imaging the myocardium, brain and hepatobiliary system, in humans and other mammalian species.
    Type: Grant
    Filed: October 14, 1986
    Date of Patent: December 22, 1987
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Thomas A. Feld, Pedro N. Juri, Elizabeth N. Treher
  • Patent number: 4654169
    Abstract: 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: Grant
    Filed: January 27, 1986
    Date of Patent: March 31, 1987
    Assignee: Givaudan Corporation
    Inventor: Paul A. Ochsner
  • Patent number: 4560797
    Abstract: 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: Grant
    Filed: December 20, 1982
    Date of Patent: December 24, 1985
    Assignee: Allied Corporation
    Inventors: Jean Yamanis, Emery J. Carlson, John N. Armor
  • Patent number: 4517382
    Abstract: 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: Grant
    Filed: September 16, 1982
    Date of Patent: May 14, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Lothar Janitschke, Werner Hoffmann
  • Patent number: 4504681
    Abstract: 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: Grant
    Filed: December 20, 1982
    Date of Patent: March 12, 1985
    Assignee: Allied Corporation
    Inventor: John N. Armor
  • Patent number: 4408077
    Abstract: 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: Grant
    Filed: November 13, 1981
    Date of Patent: October 4, 1983
    Assignee: Ayerst, McKeena & Harrison, Inc.
    Inventors: Kazimir Sestanj, Steven Fung, Nedumparambil A. Abraham, Francesco Bellini
  • Patent number: 4395413
    Abstract: 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: Grant
    Filed: June 24, 1980
    Date of Patent: July 26, 1983
    Assignee: Egyt Gyogyszervegyeszeti Gyar
    Inventors: Zoltan Budai, Aranka Lay nee Konya, Tibor Mezei, Lujza Petocz, Katalin Grasser, Ibolya Kosoczky, Eniko Szirt nee Kiszelly, Peter Gorog
  • Patent number: 4337358
    Abstract: 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: Grant
    Filed: April 13, 1981
    Date of Patent: June 29, 1982
    Assignee: Allied Corporation
    Inventor: John N. Armor
  • Patent number: 4281194
    Abstract: 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: Grant
    Filed: February 28, 1980
    Date of Patent: July 28, 1981
    Assignee: Allied Chemical Corporation
    Inventors: John N. Armor, Emery J. Carlson
  • Patent number: 4256668
    Abstract: 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: Grant
    Filed: June 20, 1979
    Date of Patent: March 17, 1981
    Assignee: Allied Chemical Corporation
    Inventors: Chempolil T. Mathew, Donald Pickens
  • Patent number: 4242277
    Abstract: 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: Grant
    Filed: May 30, 1979
    Date of Patent: December 30, 1980
    Assignee: Mitsubishi Petrochemical Company, Limited
    Inventors: Morihisa Tanaka, Kazuhiko Konno, Norio Sasaki, Kunio Uchimura