Of Ketone Patents (Class 562/527)
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Publication number: 20140256980Abstract: A continuous process and system for manufacturing beta-hydroxy-beta-methylbutyrate (HMB) and salts thereof is provided. The continuous process includes providing at least one oxidant and diacetone alcohol, and combining the at least one oxidant with the diacetone alcohol in a first flow reactor to produce a product stream comprising HMB or a salt thereof. Optionally, the process includes a second flow reactor for the acidification of a salt of beta-hydroxy-beta-methylbutyrate to produce beta-hydroxy-beta-methylbutyrate in free acid form.Type: ApplicationFiled: August 15, 2012Publication date: September 11, 2014Applicant: ABBOTT LABORATORIESInventor: Yao-En Li
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Publication number: 20140128622Abstract: A process for the oxidation of an organic carbonyl compound comprising reacting the organic carbonyl compound, optionally in the presence of a solvent, with hydrogen peroxide in the presence of a catalyst comprising a tin-containing zeolitic material having an MWW-type framework structure.Type: ApplicationFiled: November 5, 2013Publication date: May 8, 2014Applicant: BASF SEInventors: Nicolas Vautravers, Joaquim Henrique Teles, Andrei-Nicolae Parvulescu, Ulrich Müller
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Publication number: 20110046413Abstract: The present invention relates to a process for preparing 4-pentenoic acid, at least comprising the oxidation of a mixture (G) comprising 4-pentenal, 3-methyl-2-butanone and cyclopentene oxide, and to the use of a mixture (G) comprising 4-pentenal, 3-methyl-2-butanone and cyclopentene oxide for preparing 4-pentenoic acid. In the context of the present invention, the mixture (G) is preferably obtained as a by-product of the oxidation of cyclopentene to cyclopentanone by means of dinitrogen monoxide.Type: ApplicationFiled: August 19, 2010Publication date: February 24, 2011Applicant: BASF SEInventors: Joaquim Henrique Teles, Michael Schelper, Kai Gumlich, Mathieu Chabanas, Christian Müller, Anton Meier
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Patent number: 7868201Abstract: A process for the oxidation of hydrocarbons comprises contacting the hydrocarbon with an oxygen-containing gas in the presence of a catalyst comprising a microporous solid support, preferably a zeolite, having from 8- to 12-ring open windows and comprising non-framework metal cations selected from manganese, iron, cobalt, vanadium, chromium, copper, nickel, and ruthenium, and mixtures thereof, providing that the oxygen-containing gas does not contain significant amounts of added hydrogen. The catalyst is novel and forms part of the invention. The process may be used for oxidation of alkanes, cycloalkanes, benzene and alkylbenzenes, and is suitable for use in regioselective terminal oxidation of straight chain alkanes and for selective oxidation/separation of p-dialkylbenzenes from an alkylbenzene mixture, for example, p-xylene from an isomeric mixture of xylenes.Type: GrantFiled: July 1, 2005Date of Patent: January 11, 2011Assignee: ExxonMobil Research and Engineering CompanyInventors: Bi-Zeng Zhan, Bjorn Moden, Jihad Dakka, Jose Santiesteban, Sebastian C. Reyes, Enrique Iglesia
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Publication number: 20100249451Abstract: The classical process for the rearrangement of substituted benzil to benzilic acid is performed in the presence of sodium or potassium hydroxide as a base using ethanol-ether as a medium. The reaction requires reflux temperature for complete conversion. However, these bases containing metallic ions and generate metallic containing effluent waste which may require additional expenditure for treatment. Moreover, because of corrosive nature of base, and use of flammable solvent, the safety measures are needed during large scale production. Another method also reported for benzilic acid rearrangement at 380° C. which is practically not feasible. The present invention describes the use of quaternary ammonium hydroxides as a base for the rearrangement of the substituted benzils to benzilc acids. It also avoids the use of solvent and reaction can be carried out at relatively lower temperatures. Because of the solvent free reaction condition it reduces the mass/volume of reaction mixture.Type: ApplicationFiled: March 18, 2010Publication date: September 30, 2010Applicant: COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCHInventors: Harshadas Mitaram MESHRAM, Palakuri Ramesh GOUD, Bandi Chennakesava REDDY, Busam Ramalinga Vara PRASAD, Mende SREENIVAS, Jhillu Singh YADAV
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Patent number: 7012155Abstract: Aliphatic carboxylic acids of formulae (Ib) R1—COOH(Ia) and R2—COOH wherein R1 is tertiary C4-20-alkyl and R2 together are —(CH2)n— with n=3 to 10, are produced by oxidizing an aliphatic or alicyclic ketone of the formula (II): wherein R1 and R2 are as defined above, with molecular oxygen in the presence of a soluble manganese (II) compound. The process has a high selectivity and is carried out under very mild conditions. It is especially useful for the production of dicarboxylic acids, such as, adipic acid, from cyclic ketones.Type: GrantFiled: May 11, 2001Date of Patent: March 14, 2006Assignee: Lonza S.p.A.Inventors: Carlo Fumagalli, Francesco Minisci, Roberto Pirola
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Patent number: 6939991Abstract: In a process for preparing acrylic acid, an acrylic acid-containing product gas mixture obtained by catalytic gas phase partial oxidation of a C3 precursor of acrylic acid, after direct cooling with a quench liquid, is fractionally condensed in a separating column provided with internals, rising into itself with sidestream takeoff of crude acrylic acid, and the acrylic acid oligomers which form are dissociated and the resulting dissociation gas is subjected to a countercurrent rectification before it is recycled.Type: GrantFiled: June 20, 2003Date of Patent: September 6, 2005Assignee: BASF AktiengesellschaftInventors: Joachim Thiel, Ulrich Hammon, Dieter Baumann, Jörg Heilek, Jürgen Schröder, Klaus Joachim Müller-Engel
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Patent number: 6884909Abstract: A process for preparing saturated carboxylic acids having from one to four carbon atoms by gas-phase oxidation, includes reacting 2-butanone with oxygen over a coated catalyst which is an inert nonporous support body and a catalytically active mixed oxide composition comprising (a) one or more oxides selected from the group consisting of titanium dioxide, zirconium dioxide, tin dioxide and aluminum oxide, and (b) from 0.1% to 1.5% by weight, based on the weight of the component (a) and per m2/g of specific surface area of the component (a), of vanadium pentoxide, applied to the external surface of the support body.Type: GrantFiled: October 31, 2002Date of Patent: April 26, 2005Assignee: Consortium für elektrochemische Industrie GmbHInventors: Christoph Rüdinger, Harald Herbert Voit, Hans-Jürgen Eberle
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Patent number: 6872369Abstract: The invention relates to a process for selectively separating iron from other metal ions, in particular ions present in certain oxidation catalysts. It also relates to a process for recycling catalysts in the reaction for the oxidation of alcohols and/or ketones to carboxylic acids and more particularly the oxidation of cyclic alcohols and/or cyclic ketones to dicarboxylic acids, such as the oxidation of cyclohexanol and/or cyclohexanone to adipic acid. This process consists in treating the solution comprising the oxidation catalyst, before it is recycled, with an ion-exchange resin which makes it possible to selectively separate the iron from the other metal elements, in particular from copper and from vanadium.Type: GrantFiled: June 8, 2000Date of Patent: March 29, 2005Assignee: Rhodia Fiber and Resin IntermediatesInventors: Patrice Gotteland, Sébastien Logette
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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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Publication number: 20030176733Abstract: The invention relates to a method for oxidizing substrates such as hydrocarbons, waxes or soot. The method involves the use of a compound of formula (I) in which: R1 and R2 represent H, an aliphatic or aromatic alkoxy radical, carboxyl radical, alkoxycarbonyl radical or hydrocarbon radical, each having 1 to 20 hydrocarbon atoms, SO3H, NH2, OH, F, Cl, Br, I and/or NO2, whereby R1 and R2 designate identical or different radicals or R1 and R2 can be linked to one another via a covalent bonding; Q1 and Q2 represent C, CH, N, CR5, each being the same or different; X and Z represent C, S, CH2, each being the same or different; Y represents O and OH; k=0, 1, 2; l=0, 1, 2; m=1 to 3, and; R5 represents one of the meanings of R1. Said compound is used as a catalyst in the presence of a radical initiator, whereby the molar ratio of the catalyst to the hydrocarbon is less than 10 mol %. Peroxy compounds or azo compounds can be used as the radical initiator.Type: ApplicationFiled: January 15, 2003Publication date: September 18, 2003Inventors: Adolf Knhle, Mark Duda, Carsten Jost, Guido Fries, Jochen Kirchhoff, Thomas Schiffer
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Publication number: 20030144549Abstract: Aliphatic carboxylic acids of formulae (Ib) R1—COOH(Ia) and R2—COOH wherein R1 is tertiary C4-20-alkyl and R2 is selected from hydrogen and C1-6-alkyl, or R1 and R2 together are —(CH2)n— with n=3 to 10, are produced by oxidizing an aliphatic or alicyclic ketone of formula (II), wherein R1 and R2 are as defined above, with molecular oxygen in the presence of a soluble manganese(II) compound. The process has a high selectivity and is carried out under very mild conditions. It is especially useful for the production of dicarboxylic acids such as adipic acid from cyclic ketones.Type: ApplicationFiled: November 15, 2002Publication date: July 31, 2003Inventors: Carlo Fumagalli, Francesco Minisci, Roberto Pirola
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Publication number: 20030114709Abstract: A process for preparing saturated carboxylic acids having from one to four carbon atoms by gas-phase oxidation, includes reacting 2-butanone with oxygen over a coated catalyst which is an inert nonporous support body and a catalytically active mixed oxide composition comprising (a) one or more oxides selected from the group consisting of titanium dioxide, zirconium dioxide, tin dioxide and aluminum oxide, and (b) from 0.1% to 1.5% by weight, based on the weight of the component (a) and per m2/g of specific surface area of the component (a), of vanadium pentoxide, applied to the external surface of the support body.Type: ApplicationFiled: October 31, 2002Publication date: June 19, 2003Applicant: CONSORTIUM FUR ELEKTROCHEMISCHE INDUSTRIE GmbHInventors: Christoph Rudinger, Harald Herbert Voit, Hans-Jurgen Eberle
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Patent number: 6498269Abstract: A method for the oxidation of substrates comprising treating an aqueous, basic solution of a substrate having an oxidizable functionality using an elemental halogen as terminal oxidant in the presence of an oxoammonium catalyst/halide co-catalyst system. Use of elemental halogen, preferably chlorine gas or elemental bromine, unexpectedly allows oxidation without significant degradation of the substrate. The substrate is preferably a monosaccharide, oligosaccharide, or polysaccharide, and the oxidizable functionality is preferably an aldehyde, hemiacetal, or a primary alcohol. An effective source of the oxoammonium catalyst is 2,2,6,6-tetramethylpiperidinyl-1-oxy (TEMPO) and a particularly economical and effective catalyst is 4-acetylamino-2,2,6,6-tetramethylpiperidinyl-1-oxy.Type: GrantFiled: October 17, 2000Date of Patent: December 24, 2002Assignee: The University of ConnecticutInventors: Nabyl Merbouh, James M. Bobbitt, Christian Brückner
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Patent number: 6392092Abstract: A method for manufacturing 3-hydroxy-3-methylbutanoic acid (HMB) in commercially viable amounts is disclosed. The reaction mixture cycles through an external heat exchanger while the primary reactant is added in a warmer so as to control and maintain a low temperature for the reaction mixture. The manufacturing process herein disclosed increases yield while decreasing reaction time from the synthetic processes currently practiced.Type: GrantFiled: April 17, 2001Date of Patent: May 21, 2002Assignee: Met-Rx USA, Inc.Inventors: Lawrence W. McCoy, Daniel A. Lima, Melvin E. Miller
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Publication number: 20020004609Abstract: A process of producing an aliphatic aldehyde-acid (e.g., adipaldehyde-acid) and/or an aliphatic dicarboxylic acid (e.g., adipic acid) comprising oxidizing a cyclic ketone (e.g., cyclohexanone) with molecular oxygen in the presence of a fixed catalyst which comprises a composite of a carrier and at least one metal element belonging to the groups 4 to 11 of the Periodic Table supported on the carrier and has an acid amount of 0.06 mmol/g or more per unit weight of the carrier.Type: ApplicationFiled: June 22, 2001Publication date: January 10, 2002Applicant: Mitsubishi Chemical CorporationInventors: Masaru Fujii, Tohru Setoyama
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Publication number: 20010014757Abstract: A method for manufacturing 3-hydroxy-3-methylbutanoic acid (HMB) in commercially viable amounts is disclosed. The reaction mixture cycles through an external heat exchanger while the primary reactant is added in a warmer so as to control and maintain a low temperature for the reaction mixture. The manufacturing process herein disclosed increases yield while decreasing reaction time from the synthetic processes currently practiced.Type: ApplicationFiled: April 17, 2001Publication date: August 16, 2001Applicant: Met-Rx USA, Inc.Inventors: Lawrence W. McCoy, Daniel A. Lima, Melvin E. Miller
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Patent number: 6248922Abstract: A method for manufacturing 3-hydroxy-3-methylbutanoic acid (HMB) in commercially viable amounts is disclosed. The reaction mixture cycles through an external heat exchanger while the primary reactant is added in a warmer so as to control and maintain a low temperature for the reaction mixture. The manufacturing process herein disclosed increases yield while decreasing reaction time from the synthetic processes currently practiced.Type: GrantFiled: March 31, 2000Date of Patent: June 19, 2001Assignee: MET-RX USA Inc.Inventors: Lawrence W. McCoy, Daniel A. Lima, Melvin E. Miller
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Patent number: 6090978Abstract: A method for manufacturing 3-hydroxy-3-methylbutanoic acid (HMB) in commercially viable amounts is disclosed. The reaction mixture cycles through an external heat exchanger while the primary reactant is added in a warmer so as to control and maintain a low temperature for the reaction mixture. The manufacturing process herein disclosed increases yield while decreasing reaction time from the synthetic processes currently practiced.Type: GrantFiled: July 19, 1996Date of Patent: July 18, 2000Assignee: MET-RX USA, Inc.Inventors: Lawrence W. McCoy, Daniel A. Lima, Melvin E. Miller
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Patent number: 5763656Abstract: A method of preparing tartaric acid in which 5-ketogluconate is oxidized in a carbonate buffer at an alkaline pH preferably in the range of 8 to 10 using vanadate.Type: GrantFiled: May 8, 1997Date of Patent: June 9, 1998Assignee: Forschungszentrum Julich GmbHInventors: Ralf Klasen, Hermann Sahm, Ingo Matzerath, Wolfgang Klaui
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Patent number: 5364951Abstract: Tungsten-(VI) or molybdenum-(VI)-based compounds which contain cationic groups from onium salts anchored on solid inorganic matrices having the general formula (I):(P) - - - [(CH.sub.2).sub.n Q.sup.+ RR'R"].sub.2 [M.sub.2 O.sub.11 ].sup.2-(I)wherein:(P) represents a solid matrix of inorganic type;n represents an integer comprised within the range of from 1 to 20;Q represents a pentavalent element belonging to Group VA of the Periodic System;R, R' and R", which may be the same or different from each other, represent a hydrogen atom or an alkyl C.sub.1 C.sub.20 group;M represents a tungsten or molybdenum atom.Type: GrantFiled: October 14, 1993Date of Patent: November 15, 1994Assignee: Eniricerche S.P.A.Inventors: Paolo Soncini, Stefanio Bonsignore
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Patent number: 4959494Abstract: A method for oxidizing organic compounds by contacting organic compounds with molecular oxygen in the presence of a noble metal pyrochlore having the formula:A.sub.2+x B.sub.2-x O.sub.7-ywherein A is a pyrochlore structure metal cation, and B is one or more of Ru, Rh, Ir, Os, and Pt; x and y are greater than or equal to 0 and less than or equal to 1.0, at a temperature up to about 200.degree. C.Type: GrantFiled: July 6, 1987Date of Patent: September 25, 1990Assignee: Monsanto CompanyInventor: Timothy R. Felthouse
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Patent number: 4599446Abstract: A process for the preparation of 2-keto-L-gulonic acid by the oxidation of L-sorbose with an oxygen-containing gas in water used as the solvent, wherein the reaction is carried out in the presence of a specific catalyst, preferably with the pH of the reaction fluid kept within the range of 6 to 10. The catalyst contains platinum and/or palladium, as well as lead or bismuth. 2-Keto-L-gulonic acid is a compound which is useful as a precursor of vitamin C.Type: GrantFiled: April 17, 1985Date of Patent: July 8, 1986Assignee: Mitsui Toatsu Chemicals, IncorporatedInventor: Tadamitsu Kiyoura
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Patent number: 4570017Abstract: A process for the preparation of an optically-active (mixed) anhydride of an alpha-chiral (optically-active) carboxylic acid by treating a non-symmetrical ketene with a carboxylic acid in the presence of an optically-active (chiral) tertiary amine catalyst. Hydrolysis of the resulting (mixed) anhydride yields the optically-active acid corresponding to the non-symmetrical ketene.Type: GrantFiled: March 26, 1984Date of Patent: February 11, 1986Assignee: Shell Oil CompanyInventor: Donald W. Stoutamire
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Patent number: 4532347Abstract: The instant invention relates to a membrane solvent extraction and reaction system. More particularly it pertains to an improvement in the membrane solvent extraction system wherein a solute is extracted through a polymeric membrane from one solvent liquid phase to an extracting solvent liquid without direct contact between the liquid phases which are separated by the membrane and in which the extracting solvent has no greater solubility and usually substantially less solubility for the solute than the feed solvent. The impovement comprises converting the solute permeating across the membrane to a different chemical compound, whereby a high concentration gradient for the solute across the membrane is maintained to improve the separation of the solute from the feed solvent liquid phase.Type: GrantFiled: January 21, 1980Date of Patent: July 30, 1985Assignee: Varen TechnologyInventor: Ronald J. Vaughan
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Patent number: 4510321Abstract: Processes for the autoxidative cleavage of selected ketones such as C.sub.4 -C.sub.10 cycloalkanones having at least one hydrogen or at least one R group on a carbon alpha to the carbonyl carbon or aryl alkyl ketones having the formula III ##STR1## comprising contacting a liquid phase comprising said ketone with elemental oxygen gas, preferably air, in the presence of a pulverized alkali metal hydroxide at a temperature of no more than 50.degree. C. for a time sufficient to produce an oxidized product are disclosed. Preferred cycloalkanones, 2-alkyl- and 2-arylcyclohexanone are autoxidized in pulverized sodium hydroxide/dimethoxyethane to produce 6-alkyl- or 6-aryl-6-oxohexanoic acids, respectively.Type: GrantFiled: January 31, 1983Date of Patent: April 9, 1985Assignee: Allied CorporationInventors: Divakaran Masilamani, Edward H. Manahan
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Patent number: 4450291Abstract: A process for the decontamination of the distillation refinement residue from the process of oxidizing cyclohexane to KA oil is provided. The process comprises washing the distillation refinement residue with the crystallization by-product obtained in crystallizing adipic acid from the product stream of the process of oxidizing the KA oil with a strong acid. This crystallization residue comprises residual amounts of the strong acid and adipic acid, as well as substantial amounts of glutaric acid and succinic acid.Type: GrantFiled: May 2, 1983Date of Patent: May 22, 1984Assignee: Monsanto CompanyInventors: Ching T. Chi, J. Harvey Lester, Jr.
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Patent number: 4386222Abstract: A method is provided for oxidatively cleaving .alpha.,.beta.-unsaturated cyclic ketones, such as isophorone, with an oxidizing agent, for example, ozone, and thereafter recovering the resulting keto acid. In instances where ozone is used, an aqueous hydroperoxide and phase transfer catalyst can be used to recover the keto acid. Dione cyclics, for example, dimedone, can be obtained by direct dehydration of the keto acid.Type: GrantFiled: December 4, 1981Date of Patent: May 31, 1983Assignee: General Electric CompanyInventor: James A. Cella
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Patent number: 4304927Abstract: Compounds of the structure ##STR1## wherein X is --F or Cl and each R is independently --H, --CH.sub.3, --C.sub.2 H.sub.5, --CH.sub.2 CH.sub.2 CH.sub.3, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 or M where M is an alkali metal, an alkaline earth metal, ammonium or a quaternary ammonium are disclosed. The above compounds are prepared by treating a compound of the structure ##STR2## where each R.sup.1 is independently --CH.sub.3, --C.sub.2 H.sub.5, --CH.sub.2 CH.sub.2 CH.sub.3 or --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 ; or ##STR3## with a strong protic acid, followed, as desired, by base hydrolysis to form carboxylate salts (R.dbd.M).Type: GrantFiled: November 11, 1977Date of Patent: December 8, 1981Assignee: E. I. DuPont de Nemours and CompanyInventor: Carl G. Krespan
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Patent number: 4247716Abstract: A novel process for producing pyruvic acid is provided in which process hydroxyacetone is oxidized with a molecular oxygen-containing gas in a water-containing or aqueous solvent in the presence of a catalyst. The catalysts useful for the above oxidation reaction are those composed of either at least one metal selected from the group consisting of platinum, palladium, rhodium, ruthenium, and rhenium, or the at least one metal admixed with at least one element selected from the group consisting of silver, tellurium, tin, bismuth, lead and indium or with a compound of the at least one element. The resulting pyruvate can be effectively isolated in the form of a solid by concentrating the reaction solution and adding the concentrate to isopropyl alcohol.Type: GrantFiled: August 11, 1978Date of Patent: January 27, 1981Assignee: Mitsui Toatsu Chemicals, Inc.Inventor: Tadamitsu Kiyoura
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Patent number: 4217290Abstract: This invention consists of a process for preparing bifunctional aliphatic organic compounds of at least 6 carbon atoms, wherein a cycloaliphatic oxyhydroperoxide is reacted with an alpha-olefine having its double bond activated by a conjugate electron-attracting group, in the presence of a bivalent Cr salt, a bivalent V salt or a trivalent Ti salt.Type: GrantFiled: June 20, 1979Date of Patent: August 12, 1980Assignee: Brichima S.p.A.Inventors: Paolo Maggioni, Francesco Mauri, Attilio Citterio