Caustic Oxidant Patents (Class 562/539)
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Publication number: 20150065749Abstract: 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: ApplicationFiled: March 28, 2013Publication date: March 5, 2015Inventors: Daniël Stephan Van Es, Jacobus van Haveren, Henricus Wilhelmus Carolina Raaijmakers, Frits van der Klis, Gerardus Petrus Franciscus Maria van Engelen, Augustinus Emmanuël Frissen
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Patent number: 8940933Abstract: 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: GrantFiled: December 22, 2010Date of Patent: January 27, 2015Assignee: Kao CorporationInventors: Takeshi Shirasawa, Yasuo Amishige, Kaoru Omae, Akira Matsunaga, Akira Sakaguchi
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Patent number: 8481783Abstract: 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: GrantFiled: January 21, 2009Date of Patent: July 9, 2013Assignee: Clariant Speciality Fine Chemicals (France)Inventor: Olivier Simon
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Publication number: 20130131379Abstract: 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: ApplicationFiled: March 4, 2011Publication date: May 23, 2013Applicants: UNIVERSITE CLAUDE BERNARD LYON I, CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUEInventors: Marc Lemaire, Alain Favre-Reguillon, Bénédicte Paquit, Sylvain Claude, Yann Raoul
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Patent number: 8350080Abstract: 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: GrantFiled: January 7, 2009Date of Patent: January 8, 2013Assignee: Clariant Finance (BVI) LimitedInventors: Peter Klug, Achim Stankowiak, Oliver Franke, Franz-Xaver Scherl, Ulf Pruesse, Nadine Decker, Klaus-Dieter Vorlop
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Patent number: 8227638Abstract: 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: GrantFiled: April 5, 2007Date of Patent: July 24, 2012Assignee: AlzChem Trostberg GmbHInventors: Franz Thalhammer, Thomas Gastner
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Patent number: 7682724Abstract: 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: GrantFiled: October 16, 2003Date of Patent: March 23, 2010Assignee: Monsanto Technology LLCInventor: David A. Morgenstern
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Patent number: 7126024Abstract: 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: GrantFiled: October 16, 2002Date of Patent: October 24, 2006Assignee: Monsanto Technology LLCInventors: David A. Morgenstern, James P. Coleman, James M. Allman
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Patent number: 7019167Abstract: 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: GrantFiled: January 24, 2002Date of Patent: March 28, 2006Assignee: Asahi Kasei Kabushiki KaishaInventors: Masatsugu Kawase, Yasuhiro Murozono
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Publication number: 20040199007Abstract: 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: ApplicationFiled: April 15, 2004Publication date: October 7, 2004Inventors: Daniel Ostgard, Jorg Sauer, Andreas Freund, Monika Berweiler, Matthias Hopp, Rudolf Vanheertum, Walther Girke
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Patent number: 6762319Abstract: 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: GrantFiled: April 16, 2002Date of Patent: July 13, 2004Assignee: Rhodia Polyamide IntermediatesInventors: Eric Fache, Michel Costantini
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Patent number: 6646160Abstract: 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: GrantFiled: May 3, 2000Date of Patent: November 11, 2003Assignee: Monsanto Technology, LLCInventors: Thaddeus S. Franczyk, II, William L. Moench, Jr.
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Publication number: 20030162997Abstract: 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: ApplicationFiled: January 29, 2003Publication date: August 28, 2003Inventors: Hiroyuki Uhara, Kazuo Anyouji, Hideyuki Hironaka, Hideo Onodera
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Publication number: 20030158439Abstract: 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: ApplicationFiled: February 13, 2003Publication date: August 21, 2003Applicant: CONSORTIUM FUR ELEKTROCHEMISCHE INDUSTRIE GMBHInventors: Jurgen Stohrer, Elke Fritz-Langhals, Christian Bruninghaus, Dagmar Stauch
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Publication number: 20020019564Abstract: 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: ApplicationFiled: April 11, 2001Publication date: February 14, 2002Applicant: Monsanto CompanyInventors: David A. Morgenstern, Juan P. Arhancet, Howard C. Berk, William L. Moench, James C. Peterson
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Patent number: 6239312Abstract: 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: GrantFiled: March 17, 1999Date of Patent: May 29, 2001Assignee: Finichimicia S.p.A.Inventors: Alberto Villanti, Gianna Conti
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Patent number: 6159894Abstract: 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: GrantFiled: March 26, 1999Date of Patent: December 12, 2000Assignee: Akzo Nobel NVInventors: Ludwig Eisenhuth, Manfred F. Bergfeld
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Patent number: 5831116Abstract: 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: GrantFiled: April 18, 1997Date of Patent: November 3, 1998Assignee: Northeastern UniversityInventors: Chien-Tsung Wang, Ronald J. Willey
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Patent number: 5714623Abstract: 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: GrantFiled: May 1, 1995Date of Patent: February 3, 1998Assignee: Novaol S.r.l.Inventors: Giampiero Sabarino, Andrea Gardano, Marco Foa'
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Patent number: 5689000Abstract: 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: GrantFiled: March 20, 1995Date of Patent: November 18, 1997Assignee: Monsanto CompanyInventors: Jerry R. Ebner, Thaddeus S. Franczyk
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Patent number: 5463114Abstract: 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: GrantFiled: April 13, 1994Date of Patent: October 31, 1995Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Wolf-Eckart Noack, Paul Schulz, F. Norman Tuller
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Patent number: 5367112Abstract: 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: GrantFiled: December 13, 1993Date of Patent: November 22, 1994Assignee: Monsanto CompanyInventor: Thaddeus S. Franczyk
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Patent number: 5338859Abstract: 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: GrantFiled: February 12, 1993Date of Patent: August 16, 1994Assignee: Hoechst Celanese CorporationInventor: Apurba Bhattacharya
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Patent number: 5292936Abstract: 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: GrantFiled: April 12, 1993Date of Patent: March 8, 1994Assignee: Monsanto CompanyInventor: Thaddeus S. Franczyk
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Patent number: 5220054Abstract: 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: GrantFiled: July 27, 1992Date of Patent: June 15, 1993Assignee: Nippon Shokubai Co., Ltd.Inventors: Yoshiaki Urano, Yukio Kadono, Takakiyo Goto
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Patent number: 5220055Abstract: 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: GrantFiled: June 23, 1992Date of Patent: June 15, 1993Assignee: Nippon Shokubai Co., Ltd.Inventors: Yoshiaki Urano, Yukio Kadono, Takakiyo Goto
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Patent number: 4885387Abstract: 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: GrantFiled: February 12, 1988Date of Patent: December 5, 1989Assignee: The United States of America as represented by the Secretary of AgricultureInventor: John M. Krochta
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Patent number: 4782183Abstract: 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: GrantFiled: May 16, 1986Date of Patent: November 1, 1988Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.Inventors: Takakiyo Goto, Hiromi Yokoyama, Hideyuki Nishibayashi
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Patent number: 4709090Abstract: 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: GrantFiled: March 24, 1986Date of Patent: November 24, 1987Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.Inventors: Hideyuki Nishibayashi, Shigeyoshi Iio, Fumio Watanabe, Takakiyo Goto
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Patent number: 4652673Abstract: 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: GrantFiled: May 18, 1983Date of Patent: March 24, 1987Assignee: Nippon Kayaku Kabushiki KaishaInventors: Mutsumi Matsumoto, Kouichi Wada
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Patent number: 4546203Abstract: .beta.-Hydroxy-.beta.-methylglutaric acid is prepared by treating 3-methyl-1,3,5-pentanetriol in aqueous media with a permanganate salt.Type: GrantFiled: March 12, 1984Date of Patent: October 8, 1985Assignee: American Hoechst CorporationInventor: Ernest K. Metzner
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Patent number: 4251451Abstract: 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: GrantFiled: December 26, 1979Date of Patent: February 17, 1981Assignee: Stauffer Chemical CompanyInventors: Walter L. Magee, Arthur C. Bayer