Formation Of Carboxyl Group By Oxidation Patents (Class 562/523)
  • Patent number: 6395786
    Abstract: A sleep-inducing preparation which comprises as an effective ingredient a prostaglandin derivative represented by the formula: wherein X is a halogen atom, Y is a group represented by (CH2)m, a cis-vinylene group or a phenylene group, Z is an ethylene group, a trans-vinylene group, OCH2 or S(O)nCH2, R1 is a C3-10 cycloalkyl group, a C3-10 cycloalkyl group substituted with C1-4 alkyl group(s), a C4-13 cycloalkylalkyl group, a C5-10 alkyl group, a C5-10 alkenyl group, a C5-10 alkynyl group or a bridged cyclic hydrocarbon group, R2 is a hydrogen atom, a C1-10 alkyl group or a C3-10 cycloalkyl group, m is an integer of 1 to 3, and n is 0, 1 or 2, a pharmaceutically acceptable salt thereof or a hydrate thereof.
    Type: Grant
    Filed: November 27, 2000
    Date of Patent: May 28, 2002
    Assignees: Taisho Pharmaceutical Co., Ltd.
    Inventors: Fumie Sato, Tohru Tanami, Kazuya Kameo, Kenji Yamada, Shigeru Okuyama, Naoya Ono
  • Patent number: 6392092
    Abstract: 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: Grant
    Filed: April 17, 2001
    Date of Patent: May 21, 2002
    Assignee: Met-Rx USA, Inc.
    Inventors: Lawrence W. McCoy, Daniel A. Lima, Melvin E. Miller
  • Publication number: 20020010364
    Abstract: This invention relates to a process for producing one or more organic acids in high purity which process comprises (i) oxidizing in a liquid oxidation reactor one or more organic liquids with essentially pure oxygen or oxygen-enriched air containing at least about 50% oxygen, at a temperature sufficiently stable to prevent cycling of reaction rate, to produce a crude reaction product fluid, and (ii) refining said crude reaction product fluid to give said one or more organic acids in high purity. The oxidation temperature is preferably controlled to within about ±3° C. of a target temperature. The organic acids described herein is useful in a variety of applications, such as intermediates in the manufacture of chemical compounds, pharmaceutical manufacture and the like.
    Type: Application
    Filed: April 21, 1998
    Publication date: January 24, 2002
    Inventors: JOHN BRAITHWAITE, DAVID ROBERT BRYANT, DAVID JAMES MILLER, JOHN EARL LOGSDON
  • Patent number: 6326455
    Abstract: This invention relates to methods and reactor devices for controlling the oxidation of hydrocarbons to dibasic acids, in the presence of a cobalt catalyst and a monobasic acid, such as acetic acid, by treating the catalyst from the reaction mixture, outside the oxidation zone, after the oxidation has taken place at least partially. In one preferred embodiment, the catalyst is reduced to contain, preferably predominantly and more preferably substantially, cobalt ions in valence II, and at least partially precipitated by de-watering and/or thermal treatment. In a different preferred embodiment, the catalyst in the reaction mixture is first oxidized or maintained, preferably predominantly and more preferably substantially, at valence III, the reaction mixture is de-watered, the catalyst is reduced preferably predominantly and more preferably substantially, to valence II, causing precipitation either spontaneously at a predetermined temperature or after further thermal treatment.
    Type: Grant
    Filed: April 5, 2001
    Date of Patent: December 4, 2001
    Assignee: RPC Inc.
    Inventors: Eustathios Vassiliou, Mark W. Dassel, Ader M. Rostami, Douglas J. Dudgeon, David C. DeCoster
  • Patent number: 6320075
    Abstract: A process and an apparatus are for preparing saturated carboxylic acids having from one to four carbon atoms by gas-phase oxidation at a reaction temperature of from 100° C. to 400° C. and pressures of from 1.2×105 to 51×105 Pa in the presence of saturated or unsaturated C4-hydrocarbons and mixtures thereof. Also present in the reactor are an oxygen-containing gas and water vapor and in the presence of at least one catalyst, with part of the reactor outlet gas being recirculated in a reaction gas circuit. The acid concentration in the recirculated portion is reduced by means of a separation step, and the crude acid is separated from the reactor outlet gas by means of a countercurrent scrubber.
    Type: Grant
    Filed: March 8, 2000
    Date of Patent: November 20, 2001
    Assignee: Consortium für elektrochemische Industrie GmbH
    Inventors: Christoph Ruedinger, Hans-Juergen Eberle, Michael Hallmann
  • Publication number: 20010023285
    Abstract: This invention relates to methods and reactor devices for controlling the oxidation of hydrocarbons to dibasic acids, in the presence of a cobalt catalyst and a monobasic acid, such as acetic acid, by treating the catalyst from the reaction mixture, outside the oxidation zone, after the oxidation has taken place at least partially. In one preferred embodiment, the catalyst is reduced to contain, preferably predominantly and more preferably substantially, cobalt ions in valence II, and at least partially precipitated by de-watering and/or thermal treatment. In a different preferred embodiment, the catalyst in the reaction mixture is first oxidized or maintained, preferably predominantly and more preferably substantially, at valence III, the reaction mixture is de-watered, the catalyst is reduced preferably predominantly and more preferably substantially, to valence II, causing precipitation either spontaneously at a predetermined temperature or after further thermal treatment.
    Type: Application
    Filed: April 5, 2001
    Publication date: September 20, 2001
    Inventors: Eustathios Vassiliou, Mark W. Dassel, Ader M. Rostami, Douglas J. Dudgeon, David C. DeCoster
  • Publication number: 20010008948
    Abstract: Aliphatic primary alcohols, including aliphatic primary alcohols possessing one or more oxygen, nitrogen and/or phosphorus heteroatoms that may be atoms substituting for carbon atoms in the alkyl group or component atoms of substituents on the alkyl group, were converted into salts of carboxylic acids by contacting an alkaline aqueous solution of the primary alcohol with a catalyst comprising cobalt, copper, and at least one of cerium, iron, zinc, and zirconium. Diethanolamine, for example, was converted to sodium iminodiacetate by treatment in an aqueous medium containing sodium hydroxide with a catalyst that was obtained by reducing a mixture of cobalt, copper, and zirconium oxides with hydrogen.
    Type: Application
    Filed: February 5, 2001
    Publication date: July 19, 2001
    Inventors: James W. Ringer, David C. Molzahn, Dennis A. Hucul
  • Patent number: 6248922
    Abstract: 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: Grant
    Filed: March 31, 2000
    Date of Patent: June 19, 2001
    Assignee: MET-RX USA Inc.
    Inventors: Lawrence W. McCoy, Daniel A. Lima, Melvin E. Miller
  • Patent number: 6232490
    Abstract: A method for the preparation of acetic acid and/or methyl acetate by isomerization of methyl formate in a reaction mixture which includes water, a solvent and a catalytic system containing a halogenated promoter and an iridium-based compound. Carbon monoxide is present in the reaction mixture at a partial pressure between 0.1.105 Pa and 25.105 Pa, methyl formate is maintained below 20% by weight of the reaction mixture and water is maintained in an amount which is at most 5% by weight of the reaction mixture. In a typical system, method formate isomerizes to acetic acid according to the reaction: HCOOCH3CH3COOH.
    Type: Grant
    Filed: September 23, 1998
    Date of Patent: May 15, 2001
    Assignee: Acetex Chimie
    Inventors: Carl Patois, Robert Perron, Daniel Thiebaut
  • Patent number: 6229045
    Abstract: Aliphatic primary alcohols, including aliphatic primary alcohols possessing one or more oxygen, nitrogen and/or phosphorus heteroatoms that may be atoms substituting for carbon atoms in the alkyl group or component atoms of substituents on the alkyl group, were converted into salts of carboxylic acids by contacting an alkaline aqueous solution of the primary alcohol with a catalyst comprising cobalt, copper, and at least one of cerium, iron, zinc, and zirconium. Diethanolamine, for example, was converted to sodium iminodiacetate by treatment in an aqueous medium containing sodium hydroxide with a catalyst that was obtained by reducing a mixture of cobalt, copper, and zirconium oxides with hydrogen.
    Type: Grant
    Filed: September 14, 1999
    Date of Patent: May 8, 2001
    Assignee: Dow AgroSciences LLC
    Inventors: James W. Ringer, Dennis A. Hucul, David C. Molzahn
  • Patent number: 6174928
    Abstract: A fluorinated oligomer having COOH groups at both end and a &rgr;50° value of 1,000 to 10,000 is produced by swelling a fluorine rubber crosslinking product in an organic solvent, followed by decomposition in the presence of a base and a peroxide. The obtained fluorinated oligomer is soluble in solvent and thus easy to separate from fillers, etc., and can be effectively used as a chain-elongating agent for epoxy resin, isocyanate resin, oxazoline resin, etc.
    Type: Grant
    Filed: March 26, 1999
    Date of Patent: January 16, 2001
    Assignee: Nippon Mektron, Limited
    Inventors: Fumiyo Mizuide, Haruyoshi Tatsu, Sergey Vasilievich Sokolov, Michail Vasiliyevich Zhuravlev, Igor Vladimirovich Kokotin, Olga Viktorinovna Blagodatova
  • Patent number: 6111136
    Abstract: The invention consists of a new method for preparing perfluoroalcanecarboxylic and perfluoroalcanesulfonic acids in which ozone is made to react, in a protic environment, upon a perfluoroalkyl chain comprising at least one oxydizable chemical group.
    Type: Grant
    Filed: September 4, 1998
    Date of Patent: August 29, 2000
    Assignees: Electricite de France Service National, Centre National de la Recherche Scientifique
    Inventors: Hatem Marzouk, Laurent Petit, Marc Tordeux, Amaya Berecibar, Claude Wakselman
  • Patent number: 6090978
    Abstract: 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: Grant
    Filed: July 19, 1996
    Date of Patent: July 18, 2000
    Assignee: MET-RX USA, Inc.
    Inventors: Lawrence W. McCoy, Daniel A. Lima, Melvin E. Miller
  • Patent number: 6090977
    Abstract: In a process for the continuous heterogeneously catalyzed gas-phase partial oxidation of an organic compound in an oxidation reactor, whose feed gas mixture comprises, apart from the organic compound to be partially oxidized and molecular oxygen as oxidant, at least one diluent gas which is essentially inert under the conditions of the heterogeneously catalyzed gas-phase partial oxidation, where the essentially inert diluent gas consists partly of combustible gases, after passage through the oxidation reactor, the combustible constituents of the inert diluent gas present in the product gas stream leaving the oxidation reactor are not recirculated to the heterogeneously catalyzed gas-phase partial oxidation, but are put to further use for the purposes of another chemical reaction.
    Type: Grant
    Filed: March 5, 1996
    Date of Patent: July 18, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Werner Hefner, Otto Machhammer, Hans-Peter Neumann, Andreas Tenten, Wilhelm Ruppel, Herbert Vogel
  • Patent number: 6090986
    Abstract: Esters of branched C.sub.9 alcohols suitable as plasticizers are formed by esterification of a C.sub.9 alcohol produced by the aldol condensation from propanal and a C.sub.6 aldehyde and hydrogenation, the propanal optionally having been made from natural gas streams.
    Type: Grant
    Filed: October 27, 1997
    Date of Patent: July 18, 2000
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Allen David Godwin, Richard Henry Schlosberg, Frank Hershkowitz, Michael G. Matturro, Gabor Kiss, Kirk Christian Nadler, Philippe Louis Buess, Richard C. Miller, Paul William Allen, Harry William Deckman, Raf Caers, Edmund John Mozeleski, Robert P Reynolds, Francis Joseph Healy
  • 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: 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: 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: 5998572
    Abstract: Methods and devices for controlling the oxidation of a hydrocarbon to an acid by regulating the temperature hold-up time, and conversion in consecutive reaction zones. The temperature in the consecutive reaction zones progressively decreases, while the hold-up time increases. Preferably, the conversion also increases. One of the major advantages of the methods and devices of the present invention is that an outstanding balance between productivity and selectivity/yield of the desired acid may be achieved. In this respect high yields and selectivities may be obtained without sacrificing productivity.
    Type: Grant
    Filed: May 12, 1998
    Date of Patent: December 7, 1999
    Assignee: RPC Inc.
    Inventors: Ader M. Rostami, Mark W. Dassel, Eustathios Vassiliou, David C. DeCoster
  • Patent number: 5994592
    Abstract: The present invention relates to a process for producing 2,2'-bis(hydroxymethyl)alkanal and 2,2'-bis(hydroxymethyl)alkanoic acid as raw materials for dimethylol alkanoic acids or trimethylol alkanes, which are useful for the production of polyesters, polyurethanes, alkyd resins and the like, in an industrially advantageous manner.
    Type: Grant
    Filed: February 12, 1998
    Date of Patent: November 30, 1999
    Assignee: Nippon Kasei Chemical Company Limited
    Inventors: Toshiharu Yokoyama, Kouji Maeda
  • Patent number: 5981804
    Abstract: A catalyst for the production of unsaturated aldehyde and unsaturated carboxylic acid by the vapor-phase catalytic oxidation of at least one compound selected from the group consisting of propylene, isobutylene, t-butanol and methyl-t-butyl ether and a method for the production of unsaturated aldehyde and unsaturated carboxylic acid by the use of this catalyst are provided. The catalyst of this invention comprises (A) a catalyst having Mo, Bi and Fe as essential components and used for the production of unsaturated aldehyde and unsaturated carboxylic acid by vapor-phase catalytic oxidation of propylene, isobutylene, t-butanol and/or methyl-t-butyl ether 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 unsaturated aldehyde and unsaturated carboxylic acid to be produced stably at a high yield for a long time.
    Type: Grant
    Filed: December 22, 1997
    Date of Patent: November 9, 1999
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Ikuo Kurimoto, Tatsuya Kawajiri, Hideo Onodera, Michio Tanimoto, Yukio Aoki
  • Patent number: 5939582
    Abstract: Methods and apparatuses for controlling exothermic reactions involving a first reactant contained in a liquid and a second reactant in a gas to form a reaction product by atomizing the liquid in an environment of a gas and removing heat of reaction by condensing vapors of the liquid in a reaction chamber. Preferably, the condensation takes place on a simultaneously atomized second liquid of lower temperature than the atomized liquid containing the first reactant. The compositions of the two liquids are preferably similar. This invention provides waste minimization and considerable environmental improvement.
    Type: Grant
    Filed: July 17, 1998
    Date of Patent: August 17, 1999
    Assignee: Twenty-First Century Research Corporation
    Inventors: Mark William Dassel, Eustathios Vassiliou
  • Patent number: 5905168
    Abstract: Process for the treatment of a material comprising a polymer, especially a polyamide. The process consists in subjecting the polyamide to hydrolysis in the presence of a hydrolyzing nitrous grouping and transforming the hydrolyzed compounds into diacids. The treatment of a polyamide 6.6 results in the recovery of adipic acid and other diacids corresponding to the participating acid monomer and to the transformation of at least one part of the diamine monomer into diacids.
    Type: Grant
    Filed: July 25, 1995
    Date of Patent: May 18, 1999
    Assignee: Rhone-Poulenc Chimie
    Inventors: Emmanuel Dos Santos, Pascal Mettvier, Michel Gubelmann
  • Patent number: 5883292
    Abstract: Methods and apparatuses for controlling exothermic reactions involving a first reactant contained in a liquid and a second reactant in a gas to form a reaction product by atomizing the liquid in an environment of a gas and removing heat of reaction by condensing vapors of the liquid in a reaction chamber. Preferably, the condensation takes place on a simultaneously atomized second liquid of lower temperature than the atomized liquid containing the first reactant. The compositions of the two liquids are preferably similar. This invention provides waste minimization and considerable environmental improvement.
    Type: Grant
    Filed: January 17, 1996
    Date of Patent: March 16, 1999
    Assignee: Twenty-First Century Research Corporation
    Inventors: Mark William Dassel, Eustathios Vassiliou
  • Patent number: 5808143
    Abstract: Catalysts of the formula I?A.sub.a B.sub.b O.sub.x !.sub.p ?C.sub.c D.sub.d Fe.sub.e Co.sub.f E.sub.i F.sub.j O.sub.y !.sub.q I,whereA is bismuth, tellurium, antimony, tin and/or copper,B is molybdenum and/or tungsten,C is an alkali metal, thallium and/or samarium,D is an alkaline earth metal, nickel, copper, cobalt, manganese, zinc, tin, cerium, chromium, cadmium, molybdenum, bismuth and/or mercury,E is phosphorus, arsenic, boron and/or antimony,F is a rare-earth metal, vanadium and/or uranium,a is from 0.01 to 8,b is from 0.1 to 30,c is from 0 to 4,d is from 0 to 20,e is from 0 to 20,f is from 0 to 20,i is from 0 to 6,j is from 0 to 15,x and y are numbers determined by the valency and frequency of the elements other than oxygen in I, and p and q are numbers whose ratio p/q is in the range from 0.001 to 0.
    Type: Grant
    Filed: March 22, 1996
    Date of Patent: September 15, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Lothar Karrer, Hans-Peter Neumann, Hans-Dieter Eichhorn, Robin Stuart Jarret
  • Patent number: 5801275
    Abstract: The present invention is a process for the scission and oxidation of ozonide materials. The process comprises introducing an oxygen-containing gas stream into an agitated liquid body in the form of fine bubbles.
    Type: Grant
    Filed: February 20, 1996
    Date of Patent: September 1, 1998
    Assignee: Henkel Corporation
    Inventors: Kenneth R. McVay, Dennis G. Gaige, William S. Kain
  • Patent number: 5731467
    Abstract: Process for the manufacture of xylaric acid, characterized in that it consists of the oxidative degradation of 5-ketogluconic acid in alkaline medium using oxygen or a gas containing it.The xylaric acid obtained is of use as a calcium-chelating agent or as a component of polyhydroxypolyamides or as an intermediate in the synthesis of xylitol.
    Type: Grant
    Filed: July 9, 1996
    Date of Patent: March 24, 1998
    Assignee: Roquette Freres
    Inventor: Guy Fleche
  • Patent number: 5714623
    Abstract: A process for the preparation of carboxylic acids and esters thereof, which involves the steps of (a) mixing an unsaturated fatty acid or corresponding ester with an oxidative substance in the presence of a catalyst selected from the group consisting of oxides of tungsten and molybdenum and their acids and alkaline salts, (b) reacting the product mixture from step (a), which comprises vicinal diols, with oxygen or an oxygen-containing gas in the presence of a cobalt-containing compound which acts as a catalyst. The product mixture from step (a) is not subjected to any purification treatments prior to undergoing step (b).
    Type: Grant
    Filed: May 1, 1995
    Date of Patent: February 3, 1998
    Assignee: Novaol S.r.l.
    Inventors: Giampiero Sabarino, Andrea Gardano, Marco Foa'
  • Patent number: 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: 5599977
    Abstract: Rapid temperature rises which characterize carbohydrate-nitric acid oxidation reactions used to form carbohydrate-derived acids may be moderated and temperature control readily maintained by blowing a gas such as air, oxygen, nitrogen or the like into the reaction mixture as needed to control the temperature of the reaction. The more moderate reaction conditions afford higher yield of the desired product with a concomitant reduction of byproducts which may be difficult to remove and usually are unwanted as well. Upon completion the oxidation mixture is made basic (e.g. with an alkali metal base hydroxide or carbonate, ammonia or an amine) to a pH at which the the carboxyl group or groups of the product carbohydrate-derived acid are entirely in the salt form. The aqueous solution is then passed through an ion retardation resin column to recover the carbohydrate-derived salt, using water as the eluent.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: February 4, 1997
    Inventors: Donald E. Kiely, Andy Carter, David P. Shrout
  • Patent number: 5543565
    Abstract: The present invention is a process for the scission and oxidation of ozonide materials. The process comprises introducing an oxygen-containing gas stream into an agitated liquid body in the form of fine bubbles.
    Type: Grant
    Filed: January 20, 1995
    Date of Patent: August 6, 1996
    Assignee: Henkel Corporation
    Inventors: Kenneth R. McVay, Dennis G. Gaige, William S. Kain
  • Patent number: 5504246
    Abstract: A process for preparing carboxylates of polyoxyalkylene siloxanes and -amines, alkylpolyoxyalkylenes, polyoxyalkylene block polymers, alkylamidepolyoxyalkylenes and alkylpolyglucosides comprising subjecting a primary hydroxyl group-containing polyoxyalkylene compound or alkylpolyglucoside to mild oxidiation. The invention also relates to the novel polyoxyalkylene amine and alkylamidepolyoxyalkylene carboxylates prepared by the process.
    Type: Grant
    Filed: June 30, 1994
    Date of Patent: April 2, 1996
    Assignee: Sandoz Ltd.
    Inventors: Parfait J. Likibi, Robert V. Casciani, Gregory L. McCraw
  • Patent number: 5455375
    Abstract: A process for preparing adipic acid from cyclohexene oxide comprising the following steps (a) and (b):(a) hydrating cyclohexene oxide to obtain 1,2-dihydroxycyclohexane and an oligomers represented by formula (I): ##STR1## wherein n represents a number of from 1 to 5 in number average, and (b) oxidizing the 1,2-dihydroxycyclohexane and the oligomers represented by formula (I) in a nitric acid aqueous solution.
    Type: Grant
    Filed: July 25, 1994
    Date of Patent: October 3, 1995
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Tohru Ide, Masahisa Yokota
  • Patent number: 5380932
    Abstract: The present invention relates to a process for the production of methacrylic acid and methacrolein by means of gas phase oxidation of isobutane in the gaseous phase at 250.degree. to 450.degree. C. on molybdenum heteropoly acid catalysts that are made up of CU.sub.a H.sub.b P.sub.c Mo.sub.d V.sub.e O.sub.f heteropoly acid compounds (I), where a=0.1 to 1, b=0 to 7.8, c=0.8 to 1.2, d=9 to 12, e=0.5 to 3, and f depends on the molar numbers a to e, and/or the heteropoly acid H.sub.8 PMo.sub.10 VO.sub.39 (II) or its anhydride PMo.sub.10 VO.sub.35 (III).
    Type: Grant
    Filed: November 24, 1993
    Date of Patent: January 10, 1995
    Assignee: Roehm GmbH Chemische Fabrik
    Inventors: Ernst Bielmeier, Thomas Haeberle, Hermann-Josef Siegert, Wilhelm Gruber
  • Patent number: 5260465
    Abstract: This invention relates to pharmaceutical compounds of structural formula (I): ##STR1## and compositions and methods of treatment utilizing these compounds to inhibit farnesyl protein transferase and farnesylation of the oncogene protein Ras.
    Type: Grant
    Filed: December 16, 1991
    Date of Patent: November 9, 1993
    Assignee: Merck & Co., Inc.
    Inventors: Sheo B. Singh, Deborah L. Zink
  • Patent number: 5223642
    Abstract: A process for the preparation of ether carboxylic acids by ethoxylation of carbohydrates followed by catalytic oxidation and the use of the products in detergents or cleaning agents.
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: June 29, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Karl-Heinz Schonwalder
  • Patent number: 5179218
    Abstract: A process for the preparation of an alkanoic acid which comprises reacting the corresponding alkanol with a solubilized stable free radical nitroxide having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R.sub.5 and R.sub.6 is alkyl, hydrogen, aryl or a substituted heteroatom, nitric acid, and a bromide ion-containing compound in the presence of an oxidant at a temperature in the range of from about 25.degree. C. to about 60.degree. C., and thereafter separating out the alkanoic acid.
    Type: Grant
    Filed: September 30, 1991
    Date of Patent: January 12, 1993
    Assignee: Shell Oil Company
    Inventor: Herbert E. Fried
  • Patent number: 4960921
    Abstract: Certain novel multiply promoted Mn-Sb oxides are superior catalysts for the ammoxidation of olefins to the corresponding unsaturated nitriles, the selective oxidation of olefins to unsaturated aldehydes and acids, and the oxydehydrogenation of olefins to diolefins.
    Type: Grant
    Filed: February 12, 1990
    Date of Patent: October 2, 1990
    Assignee: The Standard Oil Company
    Inventors: Dev. D. Suresh, Robert K. Grasselli, Frances I. Ratka, James F. Brazdil
  • Patent number: 4886888
    Abstract: Amino acids can be purpified and/or concentrated by extracting aqueous mixtures such as fermentation broths by contacting an aqueous mixture containing amino acids with an organic solution containing a water insoluble extractant selected from the group consisting of:1. A quaternary ammonium ion having the formula: ##STR1## where R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are aliphatic, each having from 1 to 22 carbon atoms, and together have a minimum of 25 carbon atoms, and where at least three of the four R groups are at least a C.sub.4.2. A quaternary phosphonium ion having the formula: ##STR2## where R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined above. 3. A tertiary sulfonium ion having the formula: ##STR3## where R.sub.1, R.sub.2 and R.sub.3 each are aliphatic with from 1 to 22 carbon atoms, and together have a minimum of 24 carbons and where at least two of these groups are at least a C.sub.6.4. An organic boride ion having the formula: ##STR4## where R.sub.1, R.sub.2, R.sub.3 and R.sub.
    Type: Grant
    Filed: December 22, 1986
    Date of Patent: December 12, 1989
    Assignee: Henkel Corporation
    Inventors: Francis W. Tuominen, Ronald R. Swanson, Phillip L. Mattison, Kenneth D. MacKay, Bradley W. Glorvigen
  • Patent number: 4886889
    Abstract: Disclosed is a process for recovery of amino acids from aqueous mixtures. In particular, it relates to a treatment of said amino acid containing aqueous mixture prior to extraction of the amino acid with a water immiscible organic solution containing a water insoluble extractant for said amino acid. The overall process of the invention which includes the pretreatment and extraction, also includes optional methods of recovering said extracted amino acid from the water immiscible organic solution. Accordingly, the invention also relates to a process for recovery of the amino acid by stripping of the amino acid from the organic solution and precipitation of the amino acid.
    Type: Grant
    Filed: May 16, 1986
    Date of Patent: December 12, 1989
    Assignee: Henkel Corporation
    Inventors: Phillip L. Mattison, Ronald P. Wirth, Michael J. Virnig, LeRoy Krbechek
  • Patent number: 4833272
    Abstract: Disclosed is a process for preparing a polycarboxylic acid, the process comprising subjecting a Diels-Alder reaction product of maleic anhydride and a diene and/or the corresponding acid to oxidative cleavage using hydrogen peroxide in the presence of at least one catalyst selected from the group consisting of tungstic acid, molybdic acid and heteropoly acids thereof.
    Type: Grant
    Filed: April 7, 1986
    Date of Patent: May 23, 1989
    Assignee: New Japan Chemical Co., Ltd.
    Inventors: Mikio Nakazawa, Kango Fujitani
  • Patent number: 4683315
    Abstract: The present invention is directed to high-coordination transition metal complexes, i.e., those of coordination number seven and above, and the use thereof in the room temperature/atmospheric pressure formation of carbon-carbon bonds via reductive coupling of linear carbon-containing ligands, and methods for the isolation and recovery of the newly formed C.sub.2 containing species.
    Type: Grant
    Filed: August 1, 1985
    Date of Patent: July 28, 1987
    Assignee: Massachusetts Institute of Technology
    Inventors: Stephen J. Lippard, Patricia A. Bianconi
  • Patent number: 4661606
    Abstract: Amino acids can be purified and/or concentrated by extracting aqueous mixtures such as fermentation broths by contacting an aqueous mixture containing amino acids with an organic solution containing a water insoluble extractant.
    Type: Grant
    Filed: June 6, 1984
    Date of Patent: April 28, 1987
    Assignee: Henkel Corporation
    Inventors: Francis W. Tuominen, Ronald R. Swanson, Phillip L. Mattison, Kenneth D. MacKay, Bradley W. Glorvigen
  • Patent number: 4658056
    Abstract: A process for the catalytic oxidation of liquid cycloparaffins to oxidation products thereof is disclosed. In the process, partial oxidation products are formed by oxidizing the cycloparaffin with molecular oxygen-containing gas in the presence of an oxidation catalyst comprising two heavy metal compounds. The first heavy metal compound is a cobalt compound having ligands selected from dialkyl phosphate, dicycloalkylphosphate and alkylcycloalkylphosphate, optionally additionally combined with pyridine. The second heavy metal compound is a chromium alkanoate. A preferred catalyst is cobalt bis[di(2-ethylhexyl)phosphate] combined with chromium naphthenate.
    Type: Grant
    Filed: April 22, 1982
    Date of Patent: April 14, 1987
    Assignee: Du Pont Canada Inc.
    Inventor: Peter A. Sipos
  • Patent number: 4414182
    Abstract: Hydrogen is generated by contacting an alkaline aqueous solution of formaldehyde with at least one catalyst selected from the group consisting of molybdenum, tungsten, molybdenum carbides, tungsten carbides, molybdenum nitrides, tungstenum borides, copper, silver, gold and compounds of copper, silver and gold.Hydrogen can be generated at ambient temperature under atmospheric pressure and, therefore, complicated steps or complicated devices are unnecessary.
    Type: Grant
    Filed: February 2, 1982
    Date of Patent: November 8, 1983
    Assignee: Hitachi, Ltd.
    Inventors: Hiroshi Okamoto, Tetsuichi Kudo, Go Kawamura
  • Patent number: 4249015
    Abstract: Carboxylic acids and/or esters are prepared by converting the ##STR1## moiety in a 1-substituted 2,2-trihaloethanol, or derivative wherein X represents halogen and R is hydrogen or an acyl group to an organic acid and/or ester grouping of the formula ##STR2## wherein R' is hydrogen or alkyl of 1 to 6 carbon atoms, in the process which comprises reacting the 1-substituted 2,2,2-trihaloethanol or acylated derivative with molecular oxygen in the presence of a catalyst comprising a complex of a transition metal having an atomic number from 21-30, 39-48 or 57-80 and at least one molecule of a ligand containing trivalent nitrogen, phosphorus, arsenic or antimony. This reaction is carried out in a reaction medium comprising an alcohol or aqueous alcohol having 1 to 6 carbon atoms optionally containing an alkali metal, said alcoholic solvent also serving as a reactant source when carboxylic acid esters are formed.
    Type: Grant
    Filed: January 26, 1979
    Date of Patent: February 3, 1981
    Assignee: Shell Oil Company
    Inventors: John A. Schofield, John E. Hawes
  • Patent number: 4147883
    Abstract: A cycloalkylhydroperoxide is converted to an alkane-dicarboxylic acid of the same number of carbon atoms, e.g. cyclohexylhydroperoxide to adipic acid, by reaction with nitrogen dioxide.
    Type: Grant
    Filed: July 26, 1976
    Date of Patent: April 3, 1979
    Assignee: Imperial Chemical Industries Limited
    Inventor: Arthur H. Gilbert
  • Patent number: 4138417
    Abstract: A process for producing a perfluorocarboxylic acid comprises reacting a perfluoroalkyl olefin with ozone to produce a perfluoroalkyl ozonide and a perfluoroalkyl aldehyde and converting said perfluoroalkyl ozonide and perfluoroalkyl aldehyde to perfluorocarboxylic acid with an oxidizing agent.
    Type: Grant
    Filed: May 3, 1977
    Date of Patent: February 6, 1979
    Assignee: Asahi Glass Company, Ltd.
    Inventors: Hiroshi Ukihashi, Takao Hayashi, Yukio Takasaki