Of Aldehyde Patents (Class 562/531)
  • Patent number: 6084124
    Abstract: 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: Grant
    Filed: February 4, 1999
    Date of Patent: July 4, 2000
    Assignee: Shell Oil Company
    Inventors: Lynn Henry Slaugh, Thomas Clayton Forschner
  • Patent number: 6084125
    Abstract: 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: Grant
    Filed: July 23, 1998
    Date of Patent: July 4, 2000
    Assignee: Praxair Technology, Inc.
    Inventors: Jeffrey Paul Kingsley, Mitchell Adis, Friedrich E. Purkert
  • Patent number: 6072082
    Abstract: 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: Grant
    Filed: February 9, 1999
    Date of Patent: June 6, 2000
    Assignee: Nippon Kasei Chemical Company
    Inventors: Hideshi Saito, Mikio Suzuki, Shoji Sakamoto, Toshiharu Yokoyama, Kouji Maeda
  • Patent number: 6049004
    Abstract: 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: Grant
    Filed: December 11, 1998
    Date of Patent: April 11, 2000
    Inventors: Donald E. Kiely, Glenn Ponder
  • Patent number: 6028220
    Abstract: 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: Grant
    Filed: July 28, 1998
    Date of Patent: February 22, 2000
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Koichi Wada, Yoshimasa Seo, Akira Iwamoto, Atsushi Sudo, Fumio Sakai, Kazuo Shiraishi, Hiroyoshi Nowatari
  • Patent number: 6013816
    Abstract: 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: Grant
    Filed: July 5, 1996
    Date of Patent: January 11, 2000
    Assignee: DSM NV
    Inventors: Onko J. Gelling, Imre Toth
  • Patent number: 5998660
    Abstract: 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: Grant
    Filed: December 23, 1997
    Date of Patent: December 7, 1999
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Bruce Armin Barner, Jonathan Joshua Kurland
  • Patent number: 5986145
    Abstract: 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: Grant
    Filed: August 21, 1998
    Date of Patent: November 16, 1999
    Assignee: Shell Oil Company
    Inventors: Joseph Broun Powell, Paul Richard Weider, Robert Lawrence Blackbourn, Stephen Blake Mullin
  • Patent number: 5980801
    Abstract: 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: Grant
    Filed: June 25, 1998
    Date of Patent: November 9, 1999
    Assignee: Twenty-First Century Research Corporation
    Inventors: Mark W. Dassel, Eustathios Vassiliou, David C. DeCoster, Ader M. Rostami
  • Patent number: 5831121
    Abstract: 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: Grant
    Filed: July 21, 1997
    Date of Patent: November 3, 1998
    Assignee: Degussa Aktiengesellschaft
    Inventors: Thomas Haas, Martin Meier, Christoph Brossmer, Dietrich Arntz, Andreas Freund
  • Patent number: 5824819
    Abstract: 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: Grant
    Filed: May 21, 1997
    Date of Patent: October 20, 1998
    Assignee: Twenty-First Century Research Corporation
    Inventors: Mark W. Dassel, Eustathios Vassiliou, David C. DeCoster, Ader M. Rostami
  • Patent number: 5817870
    Abstract: 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: Grant
    Filed: July 21, 1997
    Date of Patent: October 6, 1998
    Assignee: Degussa Aktiengesellschaft
    Inventors: Thomas Haas, Martin Meier, Christoph Brossmer, Dietrich Arntz, Andreas Freund
  • Patent number: 5801276
    Abstract: 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: Grant
    Filed: August 5, 1997
    Date of Patent: September 1, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Heinz Neumann, Winfried Joentgen, Dieter Heitkamp, Helmut Fiege
  • Patent number: 5756306
    Abstract: 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: Grant
    Filed: November 8, 1996
    Date of Patent: May 26, 1998
    Assignee: Nitto Chemical Industry Co., Ltd.
    Inventors: Yasumasa Yamaguchi, Masahiro Ushigome, Takeshi Kato
  • Patent number: 5686638
    Abstract: 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: Grant
    Filed: September 5, 1995
    Date of Patent: November 11, 1997
    Assignee: DSM Chemie Linz GmbH
    Inventors: Carlo Kos, Manfred Schoftner, Johann Friedhuber
  • Patent number: 5663388
    Abstract: 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: Grant
    Filed: June 30, 1994
    Date of Patent: September 2, 1997
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Jose M. Vargas, Magdiel Agosto
  • Patent number: 5618974
    Abstract: 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: Grant
    Filed: May 31, 1995
    Date of Patent: April 8, 1997
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Ikuo Kurimoto, Hideo Onodera, Yukio Aoki
  • Patent number: 5603813
    Abstract: 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: Grant
    Filed: August 2, 1995
    Date of Patent: February 18, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Ruhl, Marc Heider, Jochem Henkelmann, Ralf-Thomas Rahn, Harald Rust
  • Patent number: 5395965
    Abstract: 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: Grant
    Filed: May 20, 1994
    Date of Patent: March 7, 1995
    Assignee: Degussa Aktiengesellschaft
    Inventors: Roland Burmeister, Klaus Deller, Bertrand Despeyroux, Hatte Christine
  • Patent number: 5364951
    Abstract: 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: Grant
    Filed: October 14, 1993
    Date of Patent: November 15, 1994
    Assignee: Eniricerche S.P.A.
    Inventors: Paolo Soncini, Stefanio Bonsignore
  • Patent number: 5330954
    Abstract: 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: Grant
    Filed: September 3, 1992
    Date of Patent: July 19, 1994
    Assignee: Elf Atochem, S.A.
    Inventors: Emmanuel Cadot, Franck Daubrege, Gilbert Herve, Andre Teze
  • Patent number: 5248818
    Abstract: 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: Grant
    Filed: March 24, 1992
    Date of Patent: September 28, 1993
    Assignee: Degussa Aktiengesellschaft
    Inventors: Peter Werle, Martin Trageser, Ulrike Duderstadt
  • Patent number: 5215671
    Abstract: 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: Grant
    Filed: June 11, 1991
    Date of Patent: June 1, 1993
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Yuzo Ono, Thutomu Kajikuri, Shoji Kitado, Kenji Senoo
  • Patent number: 5208258
    Abstract: 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: Grant
    Filed: April 17, 1990
    Date of Patent: May 4, 1993
    Assignee: The Regents of the University of California
    Inventors: Clayton H. Heathcock, Terry J. Rosen
  • Patent number: 5202478
    Abstract: 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: Grant
    Filed: December 12, 1990
    Date of Patent: April 13, 1993
    Assignee: Chemie Linz Gesellschaft m.b.H.
    Inventors: Karl Schermanz, Manfred Schoftner, Engelbert Kloimstein, Josef Schaller, Eduard Perndorfer, Klaus Reiter, Rudolf Neuhofer
  • Patent number: 5196578
    Abstract: 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: Grant
    Filed: September 10, 1991
    Date of Patent: March 23, 1993
    Assignees: Mitsui Toatsu Chemicals, Incorporated, Kuraray Co., Ltd.
    Inventors: Morimasa Kuragano, Takeshi Isobe, Nobutaka Ueda, Minoru Koshibe, Yoshihiro Sezaki, Hirozo Segawa, Katsuji Yoguchi, Rensuke Ikarashi
  • Patent number: 5171884
    Abstract: 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: Grant
    Filed: January 22, 1991
    Date of Patent: December 15, 1992
    Assignee: Societe Francaise Hoechst
    Inventors: Regine de Mesantourne, Pierre Gallezot
  • Patent number: 5138096
    Abstract: 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: Grant
    Filed: November 16, 1990
    Date of Patent: August 11, 1992
    Assignee: Societe Francaise Hoechst
    Inventors: Alain Schouteeten, Jean-Michel Alarcon
  • Patent number: 5132452
    Abstract: 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: Grant
    Filed: December 14, 1990
    Date of Patent: July 21, 1992
    Assignee: Degussa Aktiengesellschaft
    Inventors: Klaus Deller, Helmfried Krause, Erik Peldszus, Bertrand Despeyroux
  • Patent number: 5095143
    Abstract: 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: Grant
    Filed: June 13, 1990
    Date of Patent: March 10, 1992
    Assignee: Amoco Corporation
    Inventors: Daniel L. Heberer, Paul R. Schiller, Virginia R. Seemann, Michael J. Yerkes
  • Patent number: 5091566
    Abstract: 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: Grant
    Filed: July 3, 1989
    Date of Patent: February 25, 1992
    Assignee: Societe Francaise Hoechst
    Inventors: Alain Schouteeten, Yani Christidis
  • Patent number: 5068366
    Abstract: 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: Grant
    Filed: August 6, 1990
    Date of Patent: November 26, 1991
    Assignee: Texaco Chemical Company
    Inventors: John R. Sanderson, Edward T. Marquis
  • Patent number: 5068408
    Abstract: 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: Grant
    Filed: January 31, 1990
    Date of Patent: November 26, 1991
    Assignee: Olin Corporation
    Inventors: Robert J. Raynor, Budd L. Duncan
  • Patent number: 4959494
    Abstract: 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: Grant
    Filed: July 6, 1987
    Date of Patent: September 25, 1990
    Assignee: Monsanto Company
    Inventor: Timothy R. Felthouse
  • Patent number: 4902828
    Abstract: 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: Grant
    Filed: October 18, 1984
    Date of Patent: February 20, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Wickenhaeuser, Bernd Heida, Fritz Graf, Leopold Hupfer
  • Patent number: 4843173
    Abstract: 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: Grant
    Filed: May 16, 1988
    Date of Patent: June 27, 1989
    Assignees: Kawaken Fine Chemicals Co., Ltd., Kao Corporation
    Inventors: Hisashi Saito, Shinji Ohnaka, Shigeo Fukuda
  • Patent number: 4791228
    Abstract: 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: Grant
    Filed: February 12, 1985
    Date of Patent: December 13, 1988
    Assignee: SNIA Viscosa Societa' Nazionale Industria Applicazioni Viscosa S.p.A.
    Inventors: Francesco Siclari, Pier P. Rossi, Luigi Canavesi
  • Patent number: 4698441
    Abstract: 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: Grant
    Filed: November 5, 1982
    Date of Patent: October 6, 1987
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Tadayuki Mitani, Mamoru Endo, Takashi Hiramoto
  • Patent number: 4691053
    Abstract: 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: Grant
    Filed: June 4, 1984
    Date of Patent: September 1, 1987
    Assignee: Babcock-Hitachi Kabushiki Kaisha
    Inventors: Mutsuo Yamada, Yasuyuki Nishimura, Yoshijiro Arikawa, Takanori Kuwahara, Taiji Kamiguchi, Hirotoshi Tanimoto
  • Patent number: 4620034
    Abstract: 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: Grant
    Filed: January 22, 1985
    Date of Patent: October 28, 1986
    Assignee: Akzo NV
    Inventor: Peter C. C. Smits
  • Patent number: 4549025
    Abstract: 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: Grant
    Filed: December 12, 1984
    Date of Patent: October 22, 1985
    Assignee: Montedison S.p.A.
    Inventors: Enrico Dalcanale, Giorgio Bottaccio, Stefano Campolmi, Fernando Montanari
  • Patent number: 4529550
    Abstract: 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: Grant
    Filed: January 17, 1983
    Date of Patent: July 16, 1985
    Assignee: Celanese Corporation
    Inventors: Olan S. Fruchey, James S. Alder
  • Patent number: 4503246
    Abstract: 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: Grant
    Filed: December 1, 1981
    Date of Patent: March 5, 1985
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Tadayuki Mitani, Mamoru Endo
  • Patent number: 4487720
    Abstract: 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: Grant
    Filed: September 27, 1982
    Date of Patent: December 11, 1984
    Assignee: Celanese Corporation
    Inventor: Olan S. Fruchey
  • Patent number: 4487962
    Abstract: 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: Grant
    Filed: September 27, 1982
    Date of Patent: December 11, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Richard Krabetz, Franz Merger, Matthias Schwarzmann
  • Patent number: 4485046
    Abstract: 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: Grant
    Filed: September 28, 1982
    Date of Patent: November 27, 1984
    Assignee: Celanese Corporation
    Inventor: Olan S. Fruchey
  • Patent number: 4485047
    Abstract: 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: Grant
    Filed: February 15, 1983
    Date of Patent: November 27, 1984
    Assignee: Celanese Corporation
    Inventors: Olan S. Fruchey, Edward M. de la Garza
  • Patent number: 4471061
    Abstract: 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: Grant
    Filed: May 24, 1983
    Date of Patent: September 11, 1984
    Assignee: The Standard Oil Company
    Inventors: Wilfrid G. Shaw, Christos Paparizos, Diane G. Farrington
  • Patent number: 4471062
    Abstract: 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: Grant
    Filed: June 9, 1983
    Date of Patent: September 11, 1984
    Assignee: The Standard Oil Company
    Inventors: Diane G. Farrington, James F. White
  • Patent number: 4469887
    Abstract: 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: Grant
    Filed: October 26, 1982
    Date of Patent: September 4, 1984
    Assignee: Chemische Werke Huels, AG
    Inventors: Rudolf Brockhaus, Hans-Jurgen Franke