Of Aldehyde Patents (Class 562/531)
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Patent number: 6084125Abstract: A shell and tube heat exchanger reactor with forced circulation is used to improve heat and mass transfer for exothermic liquid--liquid, gas-liquid and gas-liquid-solid reactions. Enhanced productivity and selectivity are obtained.Type: GrantFiled: July 23, 1998Date of Patent: July 4, 2000Assignee: Praxair Technology, Inc.Inventors: Jeffrey Paul Kingsley, Mitchell Adis, Friedrich E. Purkert
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Patent number: 6084124Abstract: The present invention is a method to produce an unsaturated carboxylic acid which includes the steps of: providing an epoxy compound; contacting the epoxy compound with carbon monoxide in the presence of a catalytically effective amount of a catalyst system comprising tin and cobalt under conditions effective for carbonylation of the epoxy; and recovering a .alpha.-.beta. unsaturated carboxylic acid product. The preferred epoxy is ethylene oxide which is reacted to acrylic acid by the method of the present invention.Type: GrantFiled: February 4, 1999Date of Patent: July 4, 2000Assignee: Shell Oil CompanyInventors: Lynn Henry Slaugh, Thomas Clayton Forschner
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Patent number: 6072082Abstract: A process for producing 2,2'-bis(hydroxymethyl)alkanoic acid of the present invention, comprises:a 2,2'-bis(hydroxymethyl)alkanal production step (A1) of reacting aliphatic aldehyde having two hydrogen atoms bonded to .alpha.Type: GrantFiled: February 9, 1999Date of Patent: June 6, 2000Assignee: Nippon Kasei Chemical CompanyInventors: Hideshi Saito, Mikio Suzuki, Shoji Sakamoto, Toshiharu Yokoyama, Kouji Maeda
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Patent number: 6049004Abstract: A method for synthesizing and isolating an oxidation product is disclosed wherein nitric acid is reacted with an oxidizable reactant and the desired oxidized product is extracted using an organic solvent such as a dialkyl ether. The method permits the direct crystallization of aldaric acids such as glucaric acid and mannaric acid and eliminates the necessity of employing complicated, time consuming and wasteful neutralization/acidification steps.Type: GrantFiled: December 11, 1998Date of Patent: April 11, 2000Inventors: Donald E. Kiely, Glenn Ponder
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Patent number: 6028220Abstract: The present invention concerns a method for producing acrolein and acrylic acid by carrying out vapor phase catalytic oxidation of propylene with molecular oxygen or a gas containing molecular oxygen using a oxidation catalysts comprising Mo, Bi and Fe as an essentially element and a fixed bed multitubular reactor, which comprisesa) using a plurality of supported catalysts having different activities, which was obtained, for example, by different calcination method in the production process of the supported catalysts,b) setting a catalyst layer in a reaction tube, which is formed by dividing it into plural portions in the tube axial direction, andc) arranging the aforementioned plural supported catalysts in such order that the activity becomes high toward the outlet from the inlet of the material gas in the reaction tube axial direction.Type: GrantFiled: July 28, 1998Date of Patent: February 22, 2000Assignee: Nippon Kayaku Kabushiki KaishaInventors: Koichi Wada, Yoshimasa Seo, Akira Iwamoto, Atsushi Sudo, Fumio Sakai, Kazuo Shiraishi, Hiroyoshi Nowatari
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Patent number: 6013816Abstract: Process for the preparation of a linear .omega.-formyl-carboxylic acid or a corresponding linear formylnitrile compound starting from an internally unsaturated C.sub.4 -C.sub.12 carboxylic acid or a corresponding ester or nitrile by means of hydroformylation in the presence of carbon monoxide, hydrogen and a catalyst system, wherein the hydroformylation is carried out in an aqueous medium and in that the catalyst system comprises platinum and a water-soluble organic bidentate ligand.Type: GrantFiled: July 5, 1996Date of Patent: January 11, 2000Assignee: DSM NVInventors: Onko J. Gelling, Imre Toth
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Patent number: 5998660Abstract: This invention relates to a process for preparing carboxylic acids by oxidizing an aldehyde with a peracid in the presence of an amine and/or amine N-oxide catalyst selected from the group consisting of a substituted or unsubstituted alkyl amine, alkyl amine N-oxide, aromatic amine, aromatic amine N-oxide, heterocyclic amine, heterocyclic amine N-oxide and mixtures thereof, to produce the carboxylic acid. Such carboxylic acids have utility for example as chemical intermediates.Type: GrantFiled: December 23, 1997Date of Patent: December 7, 1999Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Bruce Armin Barner, Jonathan Joshua Kurland
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Patent number: 5986145Abstract: Cobalt or rhodium carbonyl compounds are removed from an aqueous solution of 3-hydroxypropanal by a process comprising the steps of:(a) contacting the 3-hydroxypropanal solution with oxygen under acidic conditions at a temperature within the range of about 5 to about 45.degree. C. to produce an oxidation product mixture comprising an aqueous solution of 3-hydroxypropanal, one or more water-soluble cobalt or rhodium species, and byproduct carbon monoxide;(b) removing byproduct carbon monoxide from the oxidation product mixture as it is generated; and(c) passing the oxidation product mixture in contact with an acidic ion exchange resin maintained at a temperature less than about 45.degree. C. and removing at least a portion of the soluble metal compounds from the oxidation product mixture.Type: GrantFiled: August 21, 1998Date of Patent: November 16, 1999Assignee: Shell Oil CompanyInventors: Joseph Broun Powell, Paul Richard Weider, Robert Lawrence Blackbourn, Stephen Blake Mullin
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Patent number: 5980801Abstract: Methods for oxidizing a hydrocarbon to an intermediate oxidation product by utilizing an activated initiator. The initiator is activated by partially oxidizing a first mixture of the initiator and a hydrocarbon, which mixture contains a rather large amount of initiator. The first mixture may even be just initiator. The first mixture, after the partial oxidation, is mixed with a second mixture containing hydrocarbon and a smaller amount of initiator. The second mixture may even contain no initiator at all. The oxidation is continued to a desired degree. Preferably, at least one of the two mixtures, and even more preferably both reaction mixtures contain an oxidation catalyst and an acidic solvent.Type: GrantFiled: June 25, 1998Date of Patent: November 9, 1999Assignee: Twenty-First Century Research CorporationInventors: Mark W. Dassel, Eustathios Vassiliou, David C. DeCoster, Ader M. Rostami
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Patent number: 5831121Abstract: 3-hydroxy propionic acid is obtained in high yield through the catalytic oxidation of 3-hydroxy propionaldehyde with O.sub.2 or an O.sub.2 -containing gas in the aqueous phase in the presence of a platinum-group catalyst, in particular a Pd or Pt supported catalyst. The catalyst is used in a quantity corresponding to at least 10 percent by weight of the platinum-group metal relative to 3-hydroxy propionaldehyde.Type: GrantFiled: July 21, 1997Date of Patent: November 3, 1998Assignee: Degussa AktiengesellschaftInventors: Thomas Haas, Martin Meier, Christoph Brossmer, Dietrich Arntz, Andreas Freund
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Patent number: 5824819Abstract: Methods for oxidizing a hydrocarbon to an intermediate oxidation product by utilizing an activated initiator. The initiator is activated by partially oxidizing a first mixture of the initiator and a hydrocarbon, which mixture contains a rather large amount of initiator. The first mixture may even be just initiator. The first mixture, after the partial oxidation, is mixed with a second mixture containing hydrocarbon and a smaller amount of initiator. The second mixture may even contain no initiator at all. The oxidation is continued to a desired degree. Preferably, at least one of the two mixtures, and even more preferably both reaction mixtures contain an oxidation catalyst and an acidic solvent.Type: GrantFiled: May 21, 1997Date of Patent: October 20, 1998Assignee: Twenty-First Century Research CorporationInventors: Mark W. Dassel, Eustathios Vassiliou, David C. DeCoster, Ader M. Rostami
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Patent number: 5817870Abstract: Malonic acid or a salt of the same is obtained at high yield according to the invention through the catalytic oxidation with oxygen or an O.sub.2 -containing gas of 3-hydroxy propionaldehyde or 3-hydroxy propionic acid in the aqueous phase. The conversion takes place in the presence of at least 10 percent by weight, relative to the C.sub.3 building block used, of a precious metal from the platinum group. Pd and Pt supported catalysts are preferred.Type: GrantFiled: July 21, 1997Date of Patent: October 6, 1998Assignee: Degussa AktiengesellschaftInventors: Thomas Haas, Martin Meier, Christoph Brossmer, Dietrich Arntz, Andreas Freund
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Patent number: 5801276Abstract: Hydroxypivalic acid can be prepared by oxidation of hydroxypivalaldehyde with hydrogen peroxide by metering the hydrogen peroxide, as the oxidizing agent, into an aqueous hydroxypivalaldehyde reservoir in the temperature range from 60.degree. to 80.degree. C. such that a hydrogen peroxide concentration of 4% by weight, based on the total weight of the reaction mixture, is not exceeded, and ending the addition of hydrogen peroxide as soon as the concentration of hydroxypivalaldehyde in the reaction mixture falls below 1% by weight.Type: GrantFiled: August 5, 1997Date of Patent: September 1, 1998Assignee: Bayer AktiengesellschaftInventors: Karl-Heinz Neumann, Winfried Joentgen, Dieter Heitkamp, Helmut Fiege
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Patent number: 5756306Abstract: A process for producing an .alpha.-hydroxy acid or an .alpha.-hydroxyamide which comprises treating an aldehyde and prussic acid or an .alpha.-hydroxynitrile with a microorganism having nitrilase or nitrile hydratase activity in an aqueous medium and maintaining the aldehyde concentration and/or the .alpha.-hydroxynitrile concentration in the reaction mixture within a predetermined range. Also disclosed is a process for producing an .alpha.-hydroxy acid or an .alpha.-hydroxyamide from an aldehyde and prussic acid with a microorganism in an aqueous medium, which comprises maintaining the cyanogen concentration in the reaction mixture within a predetermined range and supplying the aldehyde to the reaction mixture at a predetermined ratio to the prussic acid.Type: GrantFiled: November 8, 1996Date of Patent: May 26, 1998Assignee: Nitto Chemical Industry Co., Ltd.Inventors: Yasumasa Yamaguchi, Masahiro Ushigome, Takeshi Kato
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Patent number: 5686638Abstract: Process for the preparation of aliphatic or aromatic mono- or dicarboxylic acids of 4 to 22 carbon atoms by oxidation of the corresponding aldehydes having the same number of carbon atoms in a carboxylic acid from the group consisting of formic acid, acetic acid, and propionic acid or in a carboxylic acid/water mixture at a temperature of 50.degree.-130.degree. C. and at 1 to 25 bar and in the presence of an oxidizing agent.Type: GrantFiled: September 5, 1995Date of Patent: November 11, 1997Assignee: DSM Chemie Linz GmbHInventors: Carlo Kos, Manfred Schoftner, Johann Friedhuber
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Patent number: 5663388Abstract: A process for forming acids from aldehydes which comprises reacting an oxo aldehyde with water in the presence of an acid-forming catalyst and in the absence of hydrogen, and at a pressure of about 0.1 to 6.99 MPa and a temperature of about 93.degree. to 205.degree. C., thereby converting aldehyde to an oxo acid.Type: GrantFiled: June 30, 1994Date of Patent: September 2, 1997Assignee: Exxon Chemical Patents Inc.Inventors: Jose M. Vargas, Magdiel Agosto
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Patent number: 5618974Abstract: A catalyst for the production of methacrylic acid by the vapor-phase catalyst oxidation and/or oxidative dehydrogenation of at least one compound selected rom the group consisting of methacrolein, isobutyl aldehyde, and isobutyric acid and a method for the production of methacrylic acid by the use of this catalyst are provided. The catalyst of this invention comprises (A) a composite oxide having Mo and P as essential components and used for the production of methacrylic acid by vapor-phase catalytic oxidation and/or oxidative dehydrogenation of methacrolein, isobutyl aldehyde, and/or isobutyric acid and (B) a solid acid having acid strength (Ho) of not more than -11.93. Since this catalyst excels in catalytic activity and service life, it allows methacrylic acid to be produced stably at a high yield for a long time.Type: GrantFiled: May 31, 1995Date of Patent: April 8, 1997Assignee: Nippon Shokubai Co., Ltd.Inventors: Ikuo Kurimoto, Hideo Onodera, Yukio Aoki
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Patent number: 5603813Abstract: Vinyl formate containing formic acid, acetaldehyde and water following synthesis is separated from formic acid and water in a first distillation stage and from acetaldehyde in a second stage to give pure vinyl formate.Type: GrantFiled: August 2, 1995Date of Patent: February 18, 1997Assignee: BASF AktiengesellschaftInventors: Thomas Ruhl, Marc Heider, Jochem Henkelmann, Ralf-Thomas Rahn, Harald Rust
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Patent number: 5395965Abstract: A catalyst containing platinum on carbon as carrier for the catalytic oxidation of glyoxal to glyoxalic acid. Activity and selectivity of the catalyst can be considerably improved by modification with molybdenum and/or cerium.Type: GrantFiled: May 20, 1994Date of Patent: March 7, 1995Assignee: Degussa AktiengesellschaftInventors: Roland Burmeister, Klaus Deller, Bertrand Despeyroux, Hatte Christine
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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: 5330954Abstract: A catalytic system based on oxygen, vanadium, phosphorus, and molybdenum corresponding to the formula H.sub.m X.sub.n Me.sub.p PMo.sub.12-x V.sub.x O.sub.40, wherein X represents the VO.sup.2+ cation with 0<n.ltoreq.2, H represents protons with 0.ltoreq.m<4, 0.ltoreq.x.ltoreq.3, Me is a metal ion, especially an ion of a transition metal, with 0.ltoreq.p.ltoreq.t, t depending on the charge of the corresponding ion, is useful for the oxydehydrogenation of saturated carboxylic acids to .alpha.,.beta.-unsaturated acids and for oxidizing aldehydes to acids.Type: GrantFiled: September 3, 1992Date of Patent: July 19, 1994Assignee: Elf Atochem, S.A.Inventors: Emmanuel Cadot, Franck Daubrege, Gilbert Herve, Andre Teze
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Patent number: 5248818Abstract: Calcium formate is produced in aqueous phase by reaction of calcium hydroxide with formaldehyde in the presence of hydrogen peroxide or by reaction of calcium peroxide with formaldehyde. The molar ratio of CaO or Ca(OH).sub.2 to H.sub.2 CO to H.sub.2 O.sub.2 is 1 to 2 to 1-1.2 and the molar ratio of CaO.sub.2 to H.sub.2 CO is 1 to 2. Calcium formate is obtained in an almost substantially quantitative yield and in highly pure form. The process avoids the disadvantages of prior processes for the production of calcium formate from calcium hydroxide and formaldehyde.Type: GrantFiled: March 24, 1992Date of Patent: September 28, 1993Assignee: Degussa AktiengesellschaftInventors: Peter Werle, Martin Trageser, Ulrike Duderstadt
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Patent number: 5215671Abstract: The present invention is directed to a method for recovering 2-chloropropionic acid so that this compound can be separated in a high-purity form. According to the method, crude 2-chloropropionic acid is heat-treated in the presence of a metal compound at a temperature in the range of 130.degree.-180.degree. C. where dichloro derivatives are contained as impurities or at a temperature not exceeding 160.degree. C. where no dichloro derivatives are contained. The metal compound is then removed at 160.degree. C. or lower. Final purification is thereafter conducted to obtain 2-chloropropionic acid as a high-purity product.Type: GrantFiled: June 11, 1991Date of Patent: June 1, 1993Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Yuzo Ono, Thutomu Kajikuri, Shoji Kitado, Kenji Senoo
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Patent number: 5208258Abstract: A method of preparing compactin and mevinolin, ketoacid, enone, and glutarate analogs thereof, and related compounds. The compounds are prepared in substantially enantiomerically pure form using a structurally convergent synthesis. Total syntheses of (+)-compactin, (+)-mevinolin and related compounds are provided. Novel compounds are identified, several of which show significant anti-hypercholesterolemic activity.Type: GrantFiled: April 17, 1990Date of Patent: May 4, 1993Assignee: The Regents of the University of CaliforniaInventors: Clayton H. Heathcock, Terry J. Rosen
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Patent number: 5202478Abstract: Process for the preparation of alpha, omega-alkanedicarboxylic acids of the general formula I ##STR1## in which A is an alkylene radical having 4-14 C atoms by reacting a cycloalkene of the general formula II ##STR2## in which A has the abovementioned meaning with ozone in the presence of an inert solvent, catalytically hydrogenating the peroxide solution formed, followed by oxidation of the dialdehyde formed to the diacid of the formula I in the presence of an inert aprotic solvent.Type: GrantFiled: December 12, 1990Date of Patent: April 13, 1993Assignee: Chemie Linz Gesellschaft m.b.H.Inventors: Karl Schermanz, Manfred Schoftner, Engelbert Kloimstein, Josef Schaller, Eduard Perndorfer, Klaus Reiter, Rudolf Neuhofer
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Patent number: 5196578Abstract: A process is provided for the purification of methacrylic acid. The process can easily remove dibasic acids and aldehydes containing in trace amounts as impurities. According to the process, crude methacrylic acid obtained as an aqueous solution by vapor-phase catalytic oxidation of isobutylene, tertiary butanol, methacrolein or isobutyl aldehyde is treated with at least one compound selected from the group consisting of m-aminophenol, m-phenylenediamine, 2,4-diaminotoluene and 2,4-diamino-diphenylamine, followed by distillation, optionally, in the presence of a p-phenylene diamine.Type: GrantFiled: September 10, 1991Date of Patent: March 23, 1993Assignees: Mitsui Toatsu Chemicals, Incorporated, Kuraray Co., Ltd.Inventors: Morimasa Kuragano, Takeshi Isobe, Nobutaka Ueda, Minoru Koshibe, Yoshihiro Sezaki, Hirozo Segawa, Katsuji Yoguchi, Rensuke Ikarashi
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Patent number: 5171884Abstract: Preparation process for glyoxylic acid in which glyoxal is subjected to a heterogeneous catalytic oxidation in an aqueous medium by oxygen in the presence of catalytic quantities of platinum.Type: GrantFiled: January 22, 1991Date of Patent: December 15, 1992Assignee: Societe Francaise HoechstInventors: Regine de Mesantourne, Pierre Gallezot
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Patent number: 5138096Abstract: Continuous manufacturing process for an aqueous solution of glyoxylic acid by nitric oxidation of an aqueous solution of glyoxal carried out in the presence of hydrochloric acid in which the oxidation is effected continuously using 0.80.+-.0.2 mole of nitric acid and 0.70.+-.0.05 mole of hydrochloric acid per mole of glyoxal in a reaction medium having a concentration by weight between 5 and 6% of hydrochloric acid and higher than 10% of nitric acid.Type: GrantFiled: November 16, 1990Date of Patent: August 11, 1992Assignee: Societe Francaise HoechstInventors: Alain Schouteeten, Jean-Michel Alarcon
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Patent number: 5132452Abstract: A process for making gluconic acid and its alkali metal salts by oxidizing glucose with oxygen or oxygen containing gas in an aqueous alkaline solution in the presence of an activated charcoal supported catalyst containing a platinum group metal component, e.g. platinum and palladium and bismuth wherein the platinum, palladium and bismuth are simultaneously deposited on the charcoal support.Type: GrantFiled: December 14, 1990Date of Patent: July 21, 1992Assignee: Degussa AktiengesellschaftInventors: Klaus Deller, Helmfried Krause, Erik Peldszus, Bertrand Despeyroux
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Patent number: 5095143Abstract: A method to oxidize an oxidizable component in a liquid phase with an oxygen-containing gas is disclosed. The method comprises mixing the liquid phase and gas phase in a reactor with a rotating agitator element operated at constant power.Type: GrantFiled: June 13, 1990Date of Patent: March 10, 1992Assignee: Amoco CorporationInventors: Daniel L. Heberer, Paul R. Schiller, Virginia R. Seemann, Michael J. Yerkes
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Patent number: 5091566Abstract: The invention relates to the preparation of glyoxylic acid by oxidizing an aqueous solution of glyoxal having a pH less than 1 with molecular oxygen in the presence of nitrogen monoxide as a catalyst.This process allows the practically total conversion of the starting glyoxal with a good yield of glyoxylic acid.Type: GrantFiled: July 3, 1989Date of Patent: February 25, 1992Assignee: Societe Francaise HoechstInventors: Alain Schouteeten, Yani Christidis
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Patent number: 5068366Abstract: A process for the preparation of isobutylene oxide and isobutyric acid from isobutylene and isobutyraldehyde, respectively, by a co-oxidation process conducted in the presence of oxygen and a cobalt salt catalyst at a temperature of about 20.degree. to about 180.degree. C. is disclosed.Type: GrantFiled: August 6, 1990Date of Patent: November 26, 1991Assignee: Texaco Chemical CompanyInventors: John R. Sanderson, Edward T. Marquis
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Patent number: 5068408Abstract: A process for oxidizing an organic compound selected from an aliphatic, aromatic, aliphatic/aromatic, cycloaliphatic and heterocyclic alcohol, thiol, sulfide, aldehyde, amine, amide, ketone, acid, ether, ester, and organic compounds containing an activated carbon-carbon double bond, which process comprises contacting said organic compound dissolved in an organic solvent with a hypochlorous acid solution.Type: GrantFiled: January 31, 1990Date of Patent: November 26, 1991Assignee: Olin CorporationInventors: Robert J. Raynor, Budd L. Duncan
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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: 4902828Abstract: Aqueous glyoxylic acid solutions, essentially free of other acids, are recovered from aqueous solutions which still contain other acids, by a method in which the aqueous solution is mixed with an organic nitrogen compound at as high as 50.degree. C., the phases are separated, and the glyoxylic acid is extracted from the organic phase with water, at a higher temperature.Type: GrantFiled: October 18, 1984Date of Patent: February 20, 1990Assignee: BASF AktiengesellschaftInventors: Gerhard Wickenhaeuser, Bernd Heida, Fritz Graf, Leopold Hupfer
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Patent number: 4843173Abstract: Gluconic acid is produced by oxidizing glucose with an oxygen-containing gas in an aqueous alkali solution in the presence of a palladium-bismuth/carbon catalyst which has adsorbed firstly bismuth and secondly palladium. The catalyst has an improved activity, selectivity and durability.Type: GrantFiled: May 16, 1988Date of Patent: June 27, 1989Assignees: Kawaken Fine Chemicals Co., Ltd., Kao CorporationInventors: Hisashi Saito, Shinji Ohnaka, Shigeo Fukuda
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Patent number: 4791228Abstract: A process for preparing .alpha.,.omega.-dicarboxylic acids of the formula OC--(CH.sub.2).sub.n --COOH in which n=6 to 10 is disclosed. The process consists of the catalytic oxidation of a compound of formula X--(CH.sub.2).sub.n --CHO wherein X is CHO or COOH and n is 6 to 10 by O.sub.2 pure or in mixture with inert gas, possibly under pressure, in at least one polar solvent, at a temperature comprised between 20.degree. and 90.degree. C. and in the presence of a catalyst. The catalyst is chosen from the group consisting of at least one cobalt (II) salt and one ferrous salt. The amount of the catalyst is .ltoreq.0.001 mol % calculated on the equivalents of the aldehyde groups in the starting compound.Type: GrantFiled: February 12, 1985Date of Patent: December 13, 1988Assignee: SNIA Viscosa Societa' Nazionale Industria Applicazioni Viscosa S.p.A.Inventors: Francesco Siclari, Pier P. Rossi, Luigi Canavesi
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Patent number: 4698441Abstract: A process for producing glyoxylic acid is disclosed which comprises oxidizing glyoxal with an aqueous oxidizing agent composition obtained from nitric acid and a nonoxidizing strong acid present in a concentration of 6 to 40 wt. % in the reaction mixture. Preferably, the nonoxidizing strong acid is hydrochloric acid and the reaction is carried out while nitric acid is gradually added to the reaction mixture so that the concentration of said nitric acid in said reaction mixture does not exceed 1 wt. % during the reaction.Type: GrantFiled: November 5, 1982Date of Patent: October 6, 1987Assignee: Daicel Chemical Industries, Ltd.Inventors: Tadayuki Mitani, Mamoru Endo, Takashi Hiramoto
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Patent number: 4691053Abstract: A novel process for producing oxygen-containing organic compounds with high selectivity and good yield by oxidizing organic compounds under mild conditions is provided, which process comprises using as a catalyst for the oxidation, a complex (M.sub.m X.sub.n.L.sub.l) consisting of a transition metal compound (M.sub.m X.sub.n) and an organic phosphorous compound (L) as a ligand, wherein M represents a transition metal belonging to group I, group IV.about.VII or iron group in group VIII of the periodic table; X represents an anion such as a halogen; ligand L represents an organic phosphorous compound; and m and n mean a number of the atomic valence of said transition metal (ion) M and said anion X, respectively, and l means a number of said ligand.Type: GrantFiled: June 4, 1984Date of Patent: September 1, 1987Assignee: Babcock-Hitachi Kabushiki KaishaInventors: Mutsuo Yamada, Yasuyuki Nishimura, Yoshijiro Arikawa, Takanori Kuwahara, Taiji Kamiguchi, Hirotoshi Tanimoto
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Patent number: 4620034Abstract: Preparation of 2-keto-aldonic acids, e.g., 2-keto-gluconic acid, by oxidizing an aldose, e.g. glucose, or aldonic acid in aqueous solution with molecular oxygen. Use is made of a platinum catalyst together with a catalytic amount of lead and/or bismuth and/or a compound thereof. The pH of the solution is in the range of from 4 to 12 and preferably in the range of from 7 to 9. The reaction may be carried out at a temperature in the range of 0.degree. to 200.degree. C. and preferably in the range of from 25.degree. to 80.degree. C.Type: GrantFiled: January 22, 1985Date of Patent: October 28, 1986Assignee: Akzo NVInventor: Peter C. C. Smits
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Patent number: 4549025Abstract: Carboxylic acids having the general formula:R--COOHwherein R is selected from the group consisting of aryl, aralkyl, aralkenyl, aralkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, heteroarylalkynyl, alkyl, alkenyl and alkynyl, optionally substituted by inert or non-reactive substituents under the reaction conditions, are obtained by oxidation of the corresponding aldehydes with an alkali metal or alkaline-earth metal chlorite in the presence of hydrogen peroxide and in an aqueous-organic solvent. The resulting carboxylic acids are utilizable as intermediates for preparing fine chemicals in known ways.Type: GrantFiled: December 12, 1984Date of Patent: October 22, 1985Assignee: Montedison S.p.A.Inventors: Enrico Dalcanale, Giorgio Bottaccio, Stefano Campolmi, Fernando Montanari
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Patent number: 4529550Abstract: Improvements in efficiencies and yields are achieved in the production of a saturated aliphatic monocarboxylic acid containing 5 to 9 carbon atoms from its corresponding aldehyde by rapidly hydrolyzing the anhydride of the monocarboxylic acid formed in the oxidation. The hydrolysis is accomplished by contacting the anhydride with water at a temperature from about 130.degree. C. to about 215.degree. C. and at a pressure under which the water is maintained in the liquid state to convert the anhydride to its corresponding acid.Type: GrantFiled: January 17, 1983Date of Patent: July 16, 1985Assignee: Celanese CorporationInventors: Olan S. Fruchey, James S. Alder
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Patent number: 4503246Abstract: A process for the preparation of glyoxylic acid is disclosed which comprises reacting an aqueous solution of glyoxal with chlorine. The reaction is preferably carried out under pressure, under the condition that the hydrochloric acid concentration in the aqueous solution of glyoxal is 1 to 15%. The reaction can be carried out in the presence of a catalytically effective amount of bromine as a catalyst.Type: GrantFiled: December 1, 1981Date of Patent: March 5, 1985Assignee: Daicel Chemical Industries, Ltd.Inventors: Tadayuki Mitani, Mamoru Endo
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Patent number: 4487962Abstract: An oxidation catalyst wherein the catalytically active component has the general formulaMo.sub.12 P.sub.a Rh.sub.b Cu.sub.c V.sub.d Cs.sub.e X.sub.f Y.sub.g Z.sub.h O.sub.x,where X is Cr and/or Fe, Y is Nb, Z is Na, Li, K and/or Rb, a is 0.1-4, b is 0.001-1, c is 0.05-2, d is 0.05-4, e is 0.1-5, f is 0-2, g is 0-3 and h is 0-2, and x is the number of oxygen atoms required to saturate the valencies of the other constituents, is very suitable for the preparation of methacrylic acid by gas phase oxidation of methacrolein with an oxygen-containing and steam-containing gas mixture.Type: GrantFiled: September 27, 1982Date of Patent: December 11, 1984Assignee: BASF AktiengesellschaftInventors: Richard Krabetz, Franz Merger, Matthias Schwarzmann
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Patent number: 4487720Abstract: In the purification of the corresponding acid products obtained by oxidizing C.sub.5 to C.sub.9 organic saturated aliphatic aldehydes in the presence of a combination of manganese and copper catalysts soluble in said acids, the liquid acid reaction product is separated from the soluble catalysts by distillation in the presence of a sufficient amount of oxygen to prevent copper from plating out on the distillation equipment.Type: GrantFiled: September 27, 1982Date of Patent: December 11, 1984Assignee: Celanese CorporationInventor: Olan S. Fruchey
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Patent number: 4485047Abstract: A process is described for recovering water soluble copper and manganese compounds from an aqueous solution by reacting the copper and manganese compounds with saturated aliphatic monocarboxylic acids containing 5 to 9 carbon atoms at elevated temperatures forming cupric and manganous alkanoates containing 5 to 9 carbon atoms, and simultaneously removing the water by distillation in the presence of sufficient oxygen-containing gas to prevent the copper from plating on the distillation equipment, recovering the cupric and manganese alkanoates.Type: GrantFiled: February 15, 1983Date of Patent: November 27, 1984Assignee: Celanese CorporationInventors: Olan S. Fruchey, Edward M. de la Garza
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Patent number: 4485046Abstract: A process for the production of cupric and manganous alkanoates containing from 6 to 9 carbon atoms is described. This process comprises first thermally decomposing a mixture of cupric and manganous oxalates, obtained from the oxidation of C.sub.6 to C.sub.9 aldehydes to the corresponding acids using a mixture of copper and manganese compounds soluble in the acid product as the catalyst, in the presence of an organic saturated aliphatic monocarboxylic acid containing from 6 to 9 carbon atoms, and in the absence of oxygen, to produce manganous alkanoate and metallic copper. The metallic copper is then oxidized with oxygen to copper in the cupric form, which reacts with the organic saturated aliphatic monocarboxylic acid present to produce cupric alkanoate. The mixtures of cupric and manganous alkanoates obtained can be used as oxidation catalysts, and in fact may be recycled to the reaction sphere in which the C.sub.6 -C.sub.Type: GrantFiled: September 28, 1982Date of Patent: November 27, 1984Assignee: Celanese CorporationInventor: Olan S. Fruchey
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Patent number: 4471062Abstract: The present invention relates to a method for the reactivation of phosphomolybdic acid based catalysts used for the conversion of saturated and unsaturated aldehydes to acids. The method comprises the step of feeding an oxide of nitrogen over the deactivated catalyst at a temperature of from about 100.degree. C. to about 400.degree. C. The method can be employed in the reactor by terminating the feed of reactant to the reactor, adjusting the reactor temperature as may be necessary to one suitable for reactivation and sweeping the reactor with a gas. Alternatively, the catalyst can be removed from the reactor for reactivation. Reactivated phosphomolybdic acid based catalysts are also disclosed. These catalysts have a ratio of molybdenum to phosphorus of 3:1 to 15:1 and are prepared by the process of feeding an oxide of nitrogen over the catalyst at a temperature of from about 100.degree. C. to about 400.degree. C.Type: GrantFiled: June 9, 1983Date of Patent: September 11, 1984Assignee: The Standard Oil CompanyInventors: Diane G. Farrington, James F. White
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Patent number: 4471061Abstract: The present invention relates to a method for maintaining the activity of PMA based catalysts during reactor shutdown by flushing the reactor with an oxide of nitrogen gas at a temperature of from about 150.degree. C. to about 370.degree. C. The method can be employed in the reactor by terminating the feed of hydrocarbon to the reactor and then flushing the reactor. The method can be employed to treat PMA based catalysts having the general formula Mo.sub.x P.sub.y A.sub.a B.sub.b C.sub.c D.sub.d E.sub.e O.sub.z wherein A is selected from the group consisting of ammonium, cesium, potassium, rubidium and thallium; B is selected from the group consisting of copper and vanadium; C is selected from the group consisting of antimony, arsenic, bismuth and tellurium; D is palladium; E is aluminum, barium, calcium, cerium, chromium, cobalt, iron, magnesium, manganese, nickel tantalum, titanium, tungsten, zinc, zirconium, chlorine and/or bromine; x can be 3 to 15, y can be 1 to 1.5; a can be 0.1 to 3; b can be 0.Type: GrantFiled: May 24, 1983Date of Patent: September 11, 1984Assignee: The Standard Oil CompanyInventors: Wilfrid G. Shaw, Christos Paparizos, Diane G. Farrington
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Patent number: 4469887Abstract: To produce methacrylic acid, firstly, isobutyraldehyde is acetalized. The resultant acetal is cleaved into the isobutenyl ether and alcohol. The isobutenyl ether is oxidized with molecular oxygen or an oxygen-containing gaseous mixture in the presence of an alkaline solution at temperatures of 30.degree.-70.degree. C. to obtain the epoxide. This epoxide is hydrolyzed to the .alpha.-hydroxyisobutyraldehyde. The latter is then oxidized with concentrated or fuming nitric acid at temperatures of 20.degree.-110.degree. C. to produce .alpha.-hydroxyisobutyric acid, and methacrylic acid is obtained therefrom by splitting off water.Type: GrantFiled: October 26, 1982Date of Patent: September 4, 1984Assignee: Chemische Werke Huels, AGInventors: Rudolf Brockhaus, Hans-Jurgen Franke