Caustic Oxidant Patents (Class 562/539)
  • Publication number: 20150065749
    Abstract: Disclosed is the oxidation of uronic acids, such as galacturonic acid, to the corresponding aldaric acids (characterized by the formula HOOC—(CHOH)n-COOH, with n being an integer of from 1 to 5) such as galactaric acids. The starting material comprising the uronic acid is subjected to oxygen under the influence of a supported gold catalyst and in the presence of a base. The oxidation occurs in good selectivity and yield, under unexpectedly mild conditions. A source of galacturonic acids is pectin, such as that derived from sugar beet pulp.
    Type: Application
    Filed: March 28, 2013
    Publication date: March 5, 2015
    Inventors: Daniël Stephan Van Es, Jacobus van Haveren, Henricus Wilhelmus Carolina Raaijmakers, Frits van der Klis, Gerardus Petrus Franciscus Maria van Engelen, Augustinus Emmanuël Frissen
  • Patent number: 8940933
    Abstract: The present invention provides a method for producing polyoxyalkylene alkyl ether carboxylic acid and a salt thereof, including supplying polyoxyalkylene alkyl ether, oxygen, and water to a continuous stirred tank reactor containing a noble metal catalyst to oxidize the polyoxyalkylene alkyl ether with oxygen, in which the molar ratio of the salt of polyoxyalkylene alkyl ether carboxylic acid to the polyoxyalkylene alkyl ether in the continuous stirred tank reactor is controlled to 0.33 to 49.
    Type: Grant
    Filed: December 22, 2010
    Date of Patent: January 27, 2015
    Assignee: Kao Corporation
    Inventors: Takeshi Shirasawa, Yasuo Amishige, Kaoru Omae, Akira Matsunaga, Akira Sakaguchi
  • Patent number: 8481783
    Abstract: The invention relates to a process for separating glyoxylic acid starting from an aqueous reaction medium containing glyoxylic acid and hydrochloric acid, comprising a step of countercurrent steam stripping of the reaction medium in order to obtain, on the one hand, a gas phase containing the volatile hydrochloric acid and, on the other hand, a liquid phase containing the purified glyoxylic acid.
    Type: Grant
    Filed: January 21, 2009
    Date of Patent: July 9, 2013
    Assignee: Clariant Speciality Fine Chemicals (France)
    Inventor: Olivier Simon
  • Publication number: 20130131379
    Abstract: The present invention relates to a method for preparing carboxylic acids, in particular mono- and dicarboxylic acids, by oxidative cleavage of a vicinal diol. According to the invention, said method consists of reacting a vicinal diol of formula I: where: p is an integer comprised between 1 and 6; R1 and R2 are, separately: an alkyl or hydroxyl group having 1 to 12 carbon atoms; a —(CH2)n—C02M group where n, which can be identical or different in R1 and R2, is an integer comprised between 1 and 11 and M is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms or an alkaline cation; or R1 and R2 jointly form an alkylene —(CH2)m- group where m is an integer comprised between 2 and 10, preferably between 2 and 6; with industrial-grade sodium hypochlorite (or bleach), in the absence of an organic solvent and without adding a catalyst, preferably at room temperature. The invention can be used for recycling natural vegetable oils.
    Type: Application
    Filed: March 4, 2011
    Publication date: May 23, 2013
    Applicants: UNIVERSITE CLAUDE BERNARD LYON I, CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE
    Inventors: Marc Lemaire, Alain Favre-Reguillon, Bénédicte Paquit, Sylvain Claude, Yann Raoul
  • Patent number: 8350080
    Abstract: A method is described for producing acyl glycinate salts of formula (II) in which R1 represents a saturated linear or branched alkyl radical comprising 1 to 21 carbon atoms or a monounsaturated or polyunsaturated linear or branched alkenyl radical comprising 2 to 21 carbon atoms, and B represents a cation, and/or the corresponding protonated acyl glycinic acid. Said method is characterized in that one or more fatty acid monoethanol amides of formula (I) in which R1 has the meaning indicated above is/are oxidized with oxygen in the presence of an optionally supported bimetallic catalyst consisting of gold and a metal from group VIII of the periodic table in the alkaline medium in order to obtain one or more acyl glycinate salts of formula (II). In order to produce the protonated acyl glycinic acids, the acyl glycinate salt/s of formula (II) is/are additionally reacted with an acid.
    Type: Grant
    Filed: January 7, 2009
    Date of Patent: January 8, 2013
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Peter Klug, Achim Stankowiak, Oliver Franke, Franz-Xaver Scherl, Ulf Pruesse, Nadine Decker, Klaus-Dieter Vorlop
  • Patent number: 8227638
    Abstract: A process for producing creatine, creatine monohydrate or guanidinoacetic acid is proposed, wherein firstly N-methylethanolamine or ethanolamine is catalytically dehydrogenated in each case in alkaline solution and the sarcosinate or glycinate solutions that are obtained in this manner are finally reacted under acidic conditions with a guanylating agent such as for example O-alkylisourea or cyanamide. In this manner products are obtained in high yields and very good purity where in contrast to the prior art no traces whatsoever of hydrocyanic acid, formaldehyde, chloroacetic acid or ammonia are present. The formation of the toxicologically critical dihydrotriazine is also avoided.
    Type: Grant
    Filed: April 5, 2007
    Date of Patent: July 24, 2012
    Assignee: AlzChem Trostberg GmbH
    Inventors: Franz Thalhammer, Thomas Gastner
  • Patent number: 7682724
    Abstract: This invention is directed to a process for reforming an alcohol. The process comprises contacting an alcohol with a reforming catalyst comprising copper at the surface of a metal supporting structure, preferably a metal sponge supporting structure comprising nickel. In a certain preferred embodiment, hydrogen produced by the reforming process is used as a fuel source for a hydrogen fuel cell to generate electric power, particularly for driving a vehicle.
    Type: Grant
    Filed: October 16, 2003
    Date of Patent: March 23, 2010
    Assignee: Monsanto Technology LLC
    Inventor: David A. Morgenstern
  • Patent number: 7126024
    Abstract: This invention is directed to a process for making a salt of a carboxylic acid. The process comprises contacting a catalyst with an alkaline mixture comprising a primary alcohol. In one embodiment, the catalyst comprises a metal supporting structure (preferably a metal sponge supporting structure comprising at least about 10% by weight nickel) having a copper-containing active phase at the surface thereof and iron as a catalyst modifier. The supporting structure is resistant to deformation under the conditions of the dehydrogenation reaction. This invention is also directed to novel nickel-containing catalysts having a copper-containing active phase and iron as a catalyst modifier which may, for example, be used in the above process. This invention is further directed to processes for making such catalysts.
    Type: Grant
    Filed: October 16, 2002
    Date of Patent: October 24, 2006
    Assignee: Monsanto Technology LLC
    Inventors: David A. Morgenstern, James P. Coleman, James M. Allman
  • Patent number: 7019167
    Abstract: A method for manufacturing an alkanedicarboxylic acid by oxidizing cycloalkanol and/or cycloalkanone with an aqueous solution of nitric acid, which comprises using an adiabatic reactor comprising a feed nozzle enabling to feed cycloalkanol and/or cycloalkanone at a linear velocity not lower than 8×10?2 m/sec and a mixing apparatus.
    Type: Grant
    Filed: January 24, 2002
    Date of Patent: March 28, 2006
    Assignee: Asahi Kasei Kabushiki Kaisha
    Inventors: Masatsugu Kawase, Yasuhiro Murozono
  • Publication number: 20040199007
    Abstract: Raney copper which is doped with at least one metal from the group comprising iron and/or noble metals is used as a catalyst in the dehydrogenation of alcohols.
    Type: Application
    Filed: April 15, 2004
    Publication date: October 7, 2004
    Inventors: Daniel Ostgard, Jorg Sauer, Andreas Freund, Monika Berweiler, Matthias Hopp, Rudolf Vanheertum, Walther Girke
  • Patent number: 6762319
    Abstract: The present invention relates to the oxidation, by means of oxygen or a gas containing it, of hydrocarbons to the corresponding carboxylic acids, alcohols and/or ketones or of alcohols and/or ketones to the corresponding carboxylic acids. It consists more precisely in a process for oxidizing hydrocarbon, alcohol and/or ketone, using oxygen or a gas containing it, in liquid phase and in the presence of a catalyst dissolved in the reaction medium, characterized in that the catalyst comprises a soluble manganese compound and at least one soluble chromium compound.
    Type: Grant
    Filed: April 16, 2002
    Date of Patent: July 13, 2004
    Assignee: Rhodia Polyamide Intermediates
    Inventors: Eric Fache, Michel Costantini
  • Patent number: 6646160
    Abstract: The present invention provides a new and useful improvement in the process to manufacture a carboxylic acid salt, particularly an amino carboxylic acid salt, from a primary alcohol, particularly a primary aminoalcohol. The process of manufacturing amino carboxylic acid salts comprises contacting an aqueous solution of a primary aminoalcohol with a strong hydroxide base selected from the group consisting of an alkali metal hydroxide, an alkaline earth metal hydroxide, an ammonium hydroxide compound including a tetraalkyl ammonium hydroxide, or the like, in the presence of an effective amount of a catalyst. The catalyst comprises one or more of elements selected from the group consisting of copper, cobalt, nickel, and cadmium as well as optionally lesser amounts of chromium, titanium, niobium, tantalum, zirconium, vanadium, molybdenum, manganese, tungsten, cobalt, nickel, or mixtures thereof.
    Type: Grant
    Filed: May 3, 2000
    Date of Patent: November 11, 2003
    Assignee: Monsanto Technology, LLC
    Inventors: Thaddeus S. Franczyk, II, William L. Moench, Jr.
  • Publication number: 20030162997
    Abstract: This invention is related to a shell-and-tube type reactor provided with reaction tubes packed with a catalyst and adapted to circulate a heat medium to the fluid outside the tubes and is characterized by a method introducing a gas into the catalyst beds so as to retain the relative humidity of the catalyst in the range of more than 40% while elevating the temperature of the reactor thereby starting up the reactor. This method prevents the catalyst from degradation of activity due to absorption of moisture, exalts the service life of the catalyst, and permits stable production of methacrylic acid.
    Type: Application
    Filed: January 29, 2003
    Publication date: August 28, 2003
    Inventors: Hiroyuki Uhara, Kazuo Anyouji, Hideyuki Hironaka, Hideo Onodera
  • Publication number: 20030158439
    Abstract: A process for preparing alkynecarboxylic acids and alkyne alcohol esters of alkynecarboxylic acids, includes an oxidation reaction of an alkyne alcohol with from 1 to 10 molar equivalents of a hypohalite based on the number of functional groups to be oxidized in the presence of a nitroxyl compound at a pH of less than 7. There is also a partial oxidation reaction of the alkyne alcohol with from 0.5 to 5 molar equivalents of a hypohalite based on the number of functional groups to be oxidized in the presence of a nitroxyl compound at a pH of less than 7.
    Type: Application
    Filed: February 13, 2003
    Publication date: August 21, 2003
    Applicant: CONSORTIUM FUR ELEKTROCHEMISCHE INDUSTRIE GMBH
    Inventors: Jurgen Stohrer, Elke Fritz-Langhals, Christian Bruninghaus, Dagmar Stauch
  • Publication number: 20020019564
    Abstract: This invention is directed to a process for making a salt of a carboxylic acid. The process comprises contacting a catalyst with an alkaline mixture comprising a primary alcohol.
    Type: Application
    Filed: April 11, 2001
    Publication date: February 14, 2002
    Applicant: Monsanto Company
    Inventors: David A. Morgenstern, Juan P. Arhancet, Howard C. Berk, William L. Moench, James C. Peterson
  • Patent number: 6239312
    Abstract: A method for the production of a salt of carboxylic acid by catalytic dehydrogenation effected by reacting the corresponding primary alcohol in aqueous solution with an alkaline hydroxide in the present of a copper catalyst, in which, before the catalytic dehydrogenation, the mass of the reagents comprising the said aqueous solution of a primary alcohol is subjected to a deoxygenation stage in order to remove or reduce the level of dissolved molecular oxygen. The deoxygenation stage is preferably carried out by bubbling an inert gas or by adding a reducing agent.
    Type: Grant
    Filed: March 17, 1999
    Date of Patent: May 29, 2001
    Assignee: Finichimicia S.p.A.
    Inventors: Alberto Villanti, Gianna Conti
  • Patent number: 6159894
    Abstract: Catalyst for dehydrogenating amino alcohols to aminocarboxylic acids or ethylene glycol (derivatives) to oxycarboxylic acids, said catalyst containing zirconium, copper and possibly an additional metal, whereby the cited metals are precipitated as hydroxides, washed, dried, calcined, and reduced, preparable in that zirconium hydroxide is precipitated from an aqueous zirconium salt solution using a base until a pH of 4 to 10 is attained, the aqueous solution of a copper salt and possibly of an additional salt is added to the zirconium hydroxide suspension, and by adding further base copper hydroxide and possibly the hydroxide of the metal contained in the additional salt is precipitated until a pH of 8 to 14 is attained, the suspension obtained is filtered, washed, dried, calcined in air at 450 to 600.degree. C. for 2 to 4 hours and finally reduced at 200 to 250.degree. C. in a hydrogen stream for 2 to 4 hours.
    Type: Grant
    Filed: March 26, 1999
    Date of Patent: December 12, 2000
    Assignee: Akzo Nobel NV
    Inventors: Ludwig Eisenhuth, Manfred F. Bergfeld
  • Patent number: 5831116
    Abstract: A process for partially oxidizing alcohols such as methanol, comprising the steps of a) introducing into a reactor unit containing a solid acid catalyst amounts of alcohol and oxygen; and a supercritical fluid (such as SCF CO.sub.2) mobile phase; and b) partially oxidizing the alcohol to its corresponding ether, aldehyde, ester or acid. In an advantageous embodiment, methanol is oxidized using an aerogel acid catalyst to produce methyl ether.
    Type: Grant
    Filed: April 18, 1997
    Date of Patent: November 3, 1998
    Assignee: Northeastern University
    Inventors: Chien-Tsung Wang, Ronald J. Willey
  • Patent number: 5714623
    Abstract: A process for the preparation of carboxylic acids and esters thereof, which involves the steps of (a) mixing an unsaturated fatty acid or corresponding ester with an oxidative substance in the presence of a catalyst selected from the group consisting of oxides of tungsten and molybdenum and their acids and alkaline salts, (b) reacting the product mixture from step (a), which comprises vicinal diols, with oxygen or an oxygen-containing gas in the presence of a cobalt-containing compound which acts as a catalyst. The product mixture from step (a) is not subjected to any purification treatments prior to undergoing step (b).
    Type: Grant
    Filed: May 1, 1995
    Date of Patent: February 3, 1998
    Assignee: Novaol S.r.l.
    Inventors: Giampiero Sabarino, Andrea Gardano, Marco Foa'
  • Patent number: 5689000
    Abstract: A process to manufacture a carboxylic acid salt is disclosed wherein an aqueous solution of a primary alcohol is contacted with a base hydroxide in the presence of an effective amount of a catalyst consisting essentially of an alkali resistant support, from about 0.05 wt. % to about 10 wt. %, based on the total weight of the catalyst, of an anchor metal is selected from the group consisting of platinum, palladium, ruthenium, and gold, and between about 1 wt. % and about 50 wt. %, based on the total weight of the catalyst, of an element selected from the group consisting of copper, cobalt, nickel, and cadmium combined with the anchor metal.
    Type: Grant
    Filed: March 20, 1995
    Date of Patent: November 18, 1997
    Assignee: Monsanto Company
    Inventors: Jerry R. Ebner, Thaddeus S. Franczyk
  • Patent number: 5463114
    Abstract: Ether carboxylic acids of the formula (I):R--(OC.sub.m H.sub.2m).sub.n --O--CH.sub.2 COOM (I)wherein R is an alkyl group having from 1 to about 22 carbon atoms, an aryl group or an aralkyl group; m is 2 or 3; n is a number from 1 to about 200; M is an alkali metal are made by oxidation of an ether alcohol wherein the ether alcohol, oxygen, and an alkali metal hydroxide are continuously added to an aqueous dispersion of a noble metal catalyst under reduced pressure.
    Type: Grant
    Filed: April 13, 1994
    Date of Patent: October 31, 1995
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Wolf-Eckart Noack, Paul Schulz, F. Norman Tuller
  • Patent number: 5367112
    Abstract: An improved process is disclosed to prepare an carboxylic acid salt. According to the process, an aqueous solution of an alcohol is contacted with an alkali metal hydroxide in the presence of an effective amount of a copper catalyst that contains from about 50 parts per million to about 10,000 parts per million of an element selected from the group consisting of chromium, titanium, niobium, tantalum, zirconium, vanadium, molybdenum, manganese, tungsten, cobalt, nickel and mixtures thereof. Raney copper is preferred.
    Type: Grant
    Filed: December 13, 1993
    Date of Patent: November 22, 1994
    Assignee: Monsanto Company
    Inventor: Thaddeus S. Franczyk
  • Patent number: 5338859
    Abstract: The present invention provides a process for the production of calcium salts of hydantoic acids and which comprises the steps of reacting a hydantoin with a calcium base material such as calcium hydroxide in an aqueous medium at a sufficient temperature and for a sufficient period of time to form the calcium salt of the corresponding hydantoic acid and then separating the calcium salt of such acid from the reaction mass. This separation can include the further steps of cooling the reaction mass down to facilitate the precipitation of the acid/salt crystals and then separating the precipitate by means of filtering or centrifugating. These acids can then be subjected to a HNO.sub.2 -mediated decarbamoylation process followed by an optical resolution step to thus provide high yields of D-p-hydroxyphenylglycine which is a key synthetic immediate or building block for semi-synthetic penicillin and cephalosporins.
    Type: Grant
    Filed: February 12, 1993
    Date of Patent: August 16, 1994
    Assignee: Hoechst Celanese Corporation
    Inventor: Apurba Bhattacharya
  • Patent number: 5292936
    Abstract: An improved process is disclosed to prepare an amino carboxylic acid salt. According to the process, an aqueous solution of an amino alcohol is contacted with an alkali metal hydroxide in the presence of an effective amount of a Raney copper catalyst that has from about 50 parts per million to about 10,000 parts per million of an element selected from the group consisting of chromium, titanium, niobium, tantalum, zirconium, vanadium, molybdenum, manganese, tungsten, cobalt, nickel and mixtures thereof.
    Type: Grant
    Filed: April 12, 1993
    Date of Patent: March 8, 1994
    Assignee: Monsanto Company
    Inventor: Thaddeus S. Franczyk
  • Patent number: 5220054
    Abstract: The present invention provides a novel process for producing an aminocarboxylic acid salt which is useful as a material for agricultural chemicals and drugs, a chelating agent, a food additive, etc. The process produces an aminocarboxylic acid salt from an aminoalcohol by subjecting the aminoalcohol to an oxidative dehydrogenation reaction in the coexistence of an alkali metal hydroxide and/or an alkaline earth metal hydroxide, a copper-containing catalyst and water, and is characterized by performing the reaction while maintaining the nickel concentration in the reaction mixture at 40 ppm or less.
    Type: Grant
    Filed: July 27, 1992
    Date of Patent: June 15, 1993
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Yoshiaki Urano, Yukio Kadono, Takakiyo Goto
  • Patent number: 5220055
    Abstract: There is provided a novel process for producing aminocarboxylic acid salts useful as starting materials of agricultural chemicals and medicines, chelating agents, food additives, and so on. This process is characterized in that when producing an aminocarboxylic acid salt by an oxidative dehydrogenation reaction of an amino alcohol in the presence of an alkali metal hydroxide and/or an alkaline earth metal hydroxide, a copper-containing catalyst and water, the reaction is performed by adding an aluminum metal and/or an aluminum compound (e.g., sodium aluminate and aluminum hydroxide) to the reaction system.
    Type: Grant
    Filed: June 23, 1992
    Date of Patent: June 15, 1993
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Yoshiaki Urano, Yukio Kadono, Takakiyo Goto
  • Patent number: 4885387
    Abstract: High yields of glycolic and oxalic acids, as well as good yields of lactic, formic, and acetic acids are produced from polysaccharide-containing materials by reacting the materials in a concentrated alkaline solution at elevated temperatures.
    Type: Grant
    Filed: February 12, 1988
    Date of Patent: December 5, 1989
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventor: John M. Krochta
  • Patent number: 4782183
    Abstract: A method for the manufacture of an aminocarboxylic acid salt which comprises subjecting to dehydrogenation an amino alcohol represented by the general formula (I): ##STR1## wherein R.sup.1 and R.sup.2 denote hydrogen, --CH.sub.2 CH.sub.2 OH, an alkyl group having 1 to 18 carbon atoms or an aminoalkyl group having 2 or 3 carbon atoms, which may be the same or different, in the presence of the hydroxide of at least one metal selected from the group consisting of alkali metals and alkaline earth metals, water and a catalyst containing copper metals or a copper compound and a zirconium compound.
    Type: Grant
    Filed: May 16, 1986
    Date of Patent: November 1, 1988
    Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.
    Inventors: Takakiyo Goto, Hiromi Yokoyama, Hideyuki Nishibayashi
  • Patent number: 4709090
    Abstract: A method for the manufacture of an oxydicarboxylic acid salt which comprises subjecting to dehydrogenation an polyethylene glycol represented by the general formula I:HO--CH.sub.2 CH.sub.2 O.sub.n H (I)wherein n is 2 to 14, in the presence of the hydroxide of at least one metal selected from the group consisting of alkali metals and alkaline earth meatals, water and a catalyst containing copper and zirconium compound.
    Type: Grant
    Filed: March 24, 1986
    Date of Patent: November 24, 1987
    Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.
    Inventors: Hideyuki Nishibayashi, Shigeyoshi Iio, Fumio Watanabe, Takakiyo Goto
  • Patent number: 4652673
    Abstract: A process for producing methacrylic acid by vapor phase oxidation of methacrolein with molecular oxygen or molecular oxygen-containing gas in the presence of isobutylene and/or tertiary butanol and in the presence of a catalyst having a heteropolyacid structure represented by the following general formula:Mo.sub.a V.sub.b P.sub.c X.sub.d O.sub.ewherein Mo, V, P, and O represent molybdenum, vanadium, phosphorus, and oxygen respectively, X represents the coexistence of copper and aresenic and the a, b, c, d and e represent the atomic ratio of the elements where:a is 10,b is a number of 6 or less excluding 0,c is a number of 0.5 to 6,d is a number of 3 or less excluding 0, ande is a number determined depending on the valance and atomic ratio of the other elements.
    Type: Grant
    Filed: May 18, 1983
    Date of Patent: March 24, 1987
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Mutsumi Matsumoto, Kouichi Wada
  • Patent number: 4546203
    Abstract: .beta.-Hydroxy-.beta.-methylglutaric acid is prepared by treating 3-methyl-1,3,5-pentanetriol in aqueous media with a permanganate salt.
    Type: Grant
    Filed: March 12, 1984
    Date of Patent: October 8, 1985
    Assignee: American Hoechst Corporation
    Inventor: Ernest K. Metzner
  • Patent number: 4251451
    Abstract: An improved process for reacting a mixture of branched and linear alcohols with a caustic, optionally in the presence of a catalyst, to produce a reaction mixture containing carboxylic acid salts, and to liberate hydrogen. The improvement comprises introducing into the reaction mixture at about a time when a significant evolution of hydrogen from the mixture begins to occur, an effective amount of an inert diluent for the reaction mixture. The effective amount is sufficient to maintain the fluidity of the reaction mixture. A preferred diluent is mineral oil. The improvement reduces the tendency of the reaction mixture to foam and solidify, thus permitting the reaction to proceed to completion and permitting the easy removal of the reaction mixture from the reaction zone. Additionally, the improvement insures that the branched and linear mixture of carboxylic acid salts produced substantially corresponds to the branched and linear mixture of alcohols reacted.
    Type: Grant
    Filed: December 26, 1979
    Date of Patent: February 17, 1981
    Assignee: Stauffer Chemical Company
    Inventors: Walter L. Magee, Arthur C. Bayer