Processes Patents (Class 568/449)
  • Patent number: 6069282
    Abstract: A process for the preparation of vinyl, alkynyl or aryl aldehydes or vinyl, alkynyl or aryl ketones by reaction of vinyl-, alkynyl- or aryl- methanols with the aid of a mediator and an oxidant, wherein the mediator is selected from the group of the aliphatic, cycloaliphatic, heterocyclic or aromatic NO or NOH containing compounds.
    Type: Grant
    Filed: May 21, 1998
    Date of Patent: May 30, 2000
    Assignee: Consortium fur elektrochemische Industrie GmbH
    Inventors: Elke Fritz-Langhals, Johannes Freudenreich, Norbert Hampp, Anton Candussio
  • Patent number: 6022983
    Abstract: The present invention provides convergent processes for preparing myxopyronins and corallopyronins, compounds useful as antibacterial therapeutics. The present invention also provides novel compositions of matter which are useful for the preparation of pyronin antibiotics.
    Type: Grant
    Filed: January 2, 1998
    Date of Patent: February 8, 2000
    Assignees: Scriptgen Pharmaceuticals, Inc., Trustees of Boston University
    Inventors: Mark A. Wuonola, Gary R. Gustafson, James S. Panek, Tao Hu, Jennifer V. Schaus
  • Patent number: 6023000
    Abstract: A process for the preparation of vinyl, alkynyl or aryl aldehydes or vinyl, alkynyl or aryl ketones includes reacting vinyl-, alkynyl- and aryl- and -methylene compounds with the aid of a mediator and an oxidant, wherein the mediator is selected from the group of the aliphatic, heterocyclic or aromatic NO or NOH containing compounds.
    Type: Grant
    Filed: May 21, 1998
    Date of Patent: February 8, 2000
    Assignee: Consortium fur elektrochemisch Industrie GmbH
    Inventors: Elke Fritz-Langhals, Johannes Freudenreich
  • Patent number: 5994593
    Abstract: 3,3-Dimethylbutyraldehyde is synthesized via hydrolysis of 1,1-dichloro-3,3-dimethylbutane or 1-bromo-1-chloro-3,3-dimethylbutane in the presence of water and a base and is purified via an aldehyde/bisulfite adduct.
    Type: Grant
    Filed: September 17, 1998
    Date of Patent: November 30, 1999
    Assignee: The NutraSweet Company
    Inventors: Indra Prakash, Zhi Guo
  • 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: 5986111
    Abstract: The present invention provides convergent processes for preparing myxopyronins and corallopyronins, compounds useful as antibacterial therapeutics. The present invention also provides novel compositions of matter which are useful for the preparation of pyronin antibiotics.
    Type: Grant
    Filed: March 21, 1997
    Date of Patent: November 16, 1999
    Assignees: Scriptgen Pharmaceuticals, Inc., Trustees of Boston University
    Inventors: Mark A. Wuonola, Gary R. Gustafson, James S. Panek, Tau Hu, Jennifer V. Schaus
  • Patent number: 5977415
    Abstract: This invention provides a method for preparing 3,3-dimethylbutyraldehyde from a tert-butyl cation precursor and vinyl chloride. The tert-butyl cation precursor is contacted with vinyl chloride in the presence of an inorganic acid, and the product is allowed to react with water to form 3,3-dimethylbutyraldehyde.
    Type: Grant
    Filed: August 20, 1998
    Date of Patent: November 2, 1999
    Assignee: The NutraSweet Company
    Inventors: Indra Prakash, Zhi Guo
  • Patent number: 5969191
    Abstract: A method wherein a gas stream containing a methyl mercaptan is passed in contact with a catalyst comprising a supported metal oxide or a bulk metal oxide in the presence of an oxidizing agent and for a time sufficient to convert at least a portion of the methyl mercaptan to formaldehyde (CH.sub.2 O) and sulfur dioxide (SO.sub.
    Type: Grant
    Filed: October 6, 1997
    Date of Patent: October 19, 1999
    Assignee: Lehigh University
    Inventor: Israel E. Wachs
  • Patent number: 5929288
    Abstract: To manufacture polyene aldehydes and polyene dialdehydes a polyene O,O-dialkyl acetal or polyene di(O,O-dialkyl acetal) is reacted with a 1-alkoxy-1,3-diene in the presence of a Lewis acid or a Bronsted acid. The reaction mixture is then hydrolyzed and the alcohol is cleaved under basic conditions from the polyene derivative produced by the reacting. Those intermediates in this process from which the alcohol is to be cleaved are novel. The final products are primarily carotenoids which can be used as colorants and pigments for foodstuffs, animal products, and the like.
    Type: Grant
    Filed: May 29, 1997
    Date of Patent: July 27, 1999
    Assignee: Roche Vitamins Inc.
    Inventor: August Ruttimann
  • Patent number: 5929286
    Abstract: A method of forming a hydrogen rich gas from a source of hydrocarbon fuel in which the hydrocarbon fuel contacts a two-part catalyst comprising a dehydrogenation portion and an oxide-ion conducting portion at a temperature not less than about 400.degree. C. for a time sufficient to generate the hydrogen rich gas while maintaining CO content less than about 5 volume percent. There is also disclosed a method of forming partially oxidized hydrocarbons from ethanes in which ethane gas contacts a two-part catalyst comprising a dehydrogenation portion and an oxide-ion conducting portion for a time and at a temperature sufficient to form an oxide.
    Type: Grant
    Filed: June 5, 1998
    Date of Patent: July 27, 1999
    Assignee: The University of Chicago
    Inventors: Michael Krumpelt, Shabbir Ahmed, Romesh Kumar, Rajiv Doshi
  • Patent number: 5917094
    Abstract: Acrolein-releasing emulsion homopolymers release acrolein in aqueous systems. They are produced by adding acrolein, at least 95% by weight pure, to a solution of an alkali hydroxide, with the temperature not exceeding 25.degree. C. during the addition, and then adjusting the pH to 5 to 7 by adding a mineral acid.
    Type: Grant
    Filed: December 16, 1997
    Date of Patent: June 29, 1999
    Assignee: Degussa-Huls Aktiengesellschaft
    Inventors: Peter Werle, Hans Peter Krimmer, Martin Trageser
  • Patent number: 5912389
    Abstract: A stabilizer for an aqueous aliphatic aldehyde solution comprising acetic acid, a halogenated acetic acid or a compound capable of releasing acetic acid or a halogenated acetic acid in water.
    Type: Grant
    Filed: October 14, 1997
    Date of Patent: June 15, 1999
    Assignee: Katayama Chemical, Inc.
    Inventor: Shinichi Matsumoto
  • Patent number: 5907066
    Abstract: A method wherein a methanol-containing waste gas stream, such as a pulp mill waste stream which contains methanol and other waste products, including methyl mercaptans, is passed in contact with a catalyst comprising certain supported metal oxides in the presence of an oxidizing agent; preferably the gas stream is contacted with the catalyst, in the presence of the oxidizing agent, for a time sufficient to convert at least a portion of the methanol to formaldehyde (CH.sub.2 O).
    Type: Grant
    Filed: October 6, 1997
    Date of Patent: May 25, 1999
    Assignee: Lehigh University
    Inventor: Israel E. Wachs
  • Patent number: 5905175
    Abstract: 1-chloro-3,3-dimethylbutane is oxidized by dimethyl sulfoxide, in the presence of an effective amount of inorganic bromide or iodide, and in the present of an effective amount of base, to produce 3,3-dimethylbutyraldehyde.
    Type: Grant
    Filed: May 20, 1998
    Date of Patent: May 18, 1999
    Assignee: The NutraSweet Company
    Inventors: Zhi Guo, Indra Prakash
  • Patent number: 5900495
    Abstract: The present invention provides a method for inhibiting fouling during caustic washing of a propylene oxide product stream comprising treating a solution comprising a propylene oxide product stream and a caustic wash under conditions and with an amount of an amine effective to inhibit said fouling.
    Type: Grant
    Filed: March 16, 1998
    Date of Patent: May 4, 1999
    Assignee: Baker Hughes Incorporated
    Inventor: Gail L. Smith
  • Patent number: 5892125
    Abstract: A process for the preparation of n-butyraldehyde and/or n-butanol, in whicha) 1,3-butadiene is caused to react with an amine of the formula IR.sup.1 R.sup.2 NH, Iin which R.sup.1 and R.sup.
    Type: Grant
    Filed: July 23, 1997
    Date of Patent: April 6, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Jurgen Kanand, Michael Roper, Rocco Paciello, Alfred Thome
  • Patent number: 5866381
    Abstract: Described is a microbiological method for producing C.sub.9, C.sub.11 and C.sub.13 alkanols defined according to the structures: ##STR1## wherein R.sub.1 is methyl or n-propyl using ketones defined according to the generic structure: ##STR2## as a substrate and using the microorganism: Pseudomonas cepacia ATCC 55792or mutants thereof.
    Type: Grant
    Filed: April 23, 1998
    Date of Patent: February 2, 1999
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mohamad I. Farbood, Laura E. Kizer, Lynda B. McLean, Mark A. Sprecker
  • Patent number: 5856584
    Abstract: This invention provides a method for preparing 3,3-dimethylbutyraldehyde from 3,3-dimethylbutanol using an oxidizing component. In one embodiment, 3,3-dimethylbutanol is oxidized to 3,3-dimethylbutyraldehyde in the vapor phase by contacting it with an oxidizing metal oxide compound. In another embodiment, the oxidation of 3,3-dimethylbutanol is carried out by treating it with 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical and an oxidizing agent in a solvent to produce 3,3-dimethylbutyraldehyde. The method of this invention provides a commercially practicable means of preparing 3,3-dimethylbutyraldehyde.
    Type: Grant
    Filed: August 6, 1997
    Date of Patent: January 5, 1999
    Assignee: The Nutrasweet Company
    Inventors: Indra Prakash, David J. Ager, Alan R. Katritzky
  • Patent number: 5772898
    Abstract: This invention relates to hydrocarbon conversion processes using a novel crystalline metallo manganese oxides that have the hollandite structure. The composition is represented by the formulaA.sub.y Mn.sub.8-x M.sub.x O.sub.16where A is a templating agent such as potassium, ammonium, and y varies from about 0.5 to about 2.0, M is a metal such as chromium, vanadium, gallium, antimony and x varies from about 0.01 to about 4.0. These oxides have a three-dimensional structure with manganese and the M metals forming the framework. Examples of the processes in which these compositions can be used are oxydehydrogenation and ammoxidation. These compositions are also effective for oxidizing cyanide in aqueous streams.
    Type: Grant
    Filed: May 2, 1997
    Date of Patent: June 30, 1998
    Assignee: UOP LLC
    Inventor: Gregory J. Lewis
  • Patent number: 5723498
    Abstract: A composition which is capable of releasing acrolein and is easy to handle contains (i) an acetal of acrolein with a C.sub.1-6 alcohol with 1 to 4 hydroxyl groups and (ii) an acid soluble therein and chemically compatible with a pK.sub.s value of less than 4 and (iii) is anhydrous. A preferred composition contains 2-vinyl-1,3-dioxolane as acetal, anhydrous oxalic acid, fumaric acid or maleic acid or a mixture of mono- and di(C.sub.1 - to C.sub.3 -)alkyl phosphate as acid and, in addition, a non-ionic surfactant. The acrolein is released at the site of use upon contact with for example water for the purpose of combatting microbial, vegetable and animal pests.
    Type: Grant
    Filed: September 13, 1995
    Date of Patent: March 3, 1998
    Assignee: Degussa Aktiengellschaft
    Inventors: Peter Werle, Martin Trageser, Oswald Helmling, Harold Jakob
  • Patent number: 5705706
    Abstract: 2-(Alkoxymethyl)acrolein of the formula ##STR1## is produced from acrolein, an alcohol ROH and formaldehyde, in one step, with a good yield being obtained. The acrolein is reacted with a substantially equimolar quantity of a source of formaldehyde in the presence of at least an equimolar quantity of the alcohol ROH and a catalytic quantity of a catalyst system based on a secondary amine and a mineral acid at a pH value of the reaction mixture in the range of 1 to less than 7.
    Type: Grant
    Filed: July 23, 1996
    Date of Patent: January 6, 1998
    Assignee: Degussa Aktiengesellschaft
    Inventors: Mathias Hoepp, Klaus Koehler, Dietrich Arntz
  • Patent number: 5705707
    Abstract: A process for the preparation of n-butyraldehyde and/or n-butanol, whereina) 1,3-butadiene is caused to react with an alcohol of the formula IROH I,to form a mixture of adducts of the formulas II ##STR1## and III ##STR2## b) the adduct III is isomerized to the adduct II, c) the adduct II is isomerized in the presence of a homogeneous or heterogeneous transition metal element catalyst to form the enol ether of the formula IV ##STR3## and d) n-butyraldehyde and/or n-butanol is/are produced from this ether IV by the reaction thereof with hydrogen and water or water only in the presence of a homogeneous or heterogeneous catalyst.
    Type: Grant
    Filed: July 12, 1996
    Date of Patent: January 6, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Jurgen Kanand, Michael Roper, Rolf Pinkos, Rocco Paciello, Alfred Thome
  • Patent number: 5689010
    Abstract: Aldehydes with a higher number of carbon atoms and high selection are prepared by reacting olefins, in particular from petrochemical refinery products, by a hydroformylation with aldol condensation using a mixed catalyst of rhodium-carbonyl-phosphines and Mannich catalyst.
    Type: Grant
    Filed: April 29, 1996
    Date of Patent: November 18, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Rocco Paciello, Franz Merger, Michael Roper, Heinz-Josef Kneuper
  • Patent number: 5686554
    Abstract: The process comprises providing a formaldehyde solution at a concentration of 80-89%; heating the solution to a temperature of 80.degree.-100.degree. C.; pouring the heated solution over heated zones on a metal belt conveyor travelling from the heated zones to other, chilled zones. The formaldehyde solution is preferably previously mixed with a catalyst.
    Type: Grant
    Filed: July 10, 1995
    Date of Patent: November 11, 1997
    Assignee: Patentes Y Novedades, S.L.
    Inventor: Luis Eek-Vancells
  • Patent number: 5585523
    Abstract: Process for the preparation of aldehydes by catalytic gas phase hydrogenation of carboxylic acid or their derivatives with the aid of a tin catalystThe invention relates to a process for the preparation of aldehydes by catalytic gas phase hydrogenation of carboxylic acids or carboxylic acid derivatives at elevated temperature, which comprises employing at tin catalyst supplied to an oxidic support material.
    Type: Grant
    Filed: September 6, 1995
    Date of Patent: December 17, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jens Weiguny, Holger Borchert, Thomas Gerdau
  • Patent number: 5567855
    Abstract: Methods for stereospecific synthesis of 9-cis olefins and retinoids. In one particular aspect, a cis olefin is generated via a lactol ring opening with complete retention of double bond configuration.
    Type: Grant
    Filed: April 21, 1994
    Date of Patent: October 22, 1996
    Assignee: Ligand Pharmaceuticals Incorporated
    Inventors: Steven K. White, Chan K. Hwang, David T. Winn
  • Patent number: 5563235
    Abstract: Fluorinated aldehydes are made by reacting a fluorinated acyl chloride with a silicon hydride in the presence of palladium. Also disclosed are fluorinated ether aldehydes and their polymers, a process for making fluorinated aldehydes polymers using titanium or aluminum alkoxide catalysts, and a process for endcapping fluorinated polymers using perfluoroallyl fluorosulfate or fluorine.
    Type: Grant
    Filed: January 16, 1996
    Date of Patent: October 8, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William B. Farnham
  • Patent number: 5560833
    Abstract: Stretches of flowing water are doped with acrolein for the purpose of preventing excessive growth of plants and algae. In order to avoid transport of acrolein, acrolein is produced at the site where it is required by deacetalation of an acrolein acetal in the presence of an aqueous mineral acid. No electrical energy is necessary for this process. An acrolein acetal and an aqueous mineral acid solution are delivered from compression-proof storage tanks into a mixing chamber by the application of pressure from a pressure cylinder. The mixture is passed through a deacetalation reactor unit which includes a tubular reactor part and a container-shaped reactor part.
    Type: Grant
    Filed: July 27, 1994
    Date of Patent: October 1, 1996
    Assignee: Degussa Aktiengesellschaft
    Inventors: Peter Werle, Bernd Geissler, Martin Trageser
  • Patent number: 5550309
    Abstract: A process for the dehydrogenation of a hydrocarbon and/or oxygenated hydrocarbon feed, which process comprises the steps of(a) sequentially contacting the feed with a catalyst bed in a reaction chamber at elevated temperature, said catalyst bed comprising a first catalyst which is a dehydrogenation catalyst to produce a dehydrogenated product and hydrogen and a second catalyst capable of adsorbing and/or reacting with at least some of said hydrogen, said second catalyst having a porous coating.(b) removing the dehydrogenated product and any hydrogen which has not been adsorbed or reacted from the reaction chamber;(c) removing at least some of the adsorbed/reacted hydrogen from the coated catalyst and/or oxidising at least some of the reduced coated catalyst, thereby regenerating the second catalyst;(d) using said regenerated second catalyst in step (a).
    Type: Grant
    Filed: October 31, 1994
    Date of Patent: August 27, 1996
    Assignee: BP Chemicals Limited
    Inventors: Barry M. Maunders, Stephen R. Partington
  • Patent number: 5512652
    Abstract: Fluorinated aldehydes are made by reacting a fluorinated acyl chloride with a silicon hydride in the presence of palladium. Also disclosed are fluorinated ether aldehydes and their polymers, a process for making fluorinated aldehydes polymers using titanium or aluminum alkoxide catalysts, and a process for endcapping fluorinated polymers using perfluoroallyl fluorosulfate or fluorine.
    Type: Grant
    Filed: February 14, 1995
    Date of Patent: April 30, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William B. Farnham
  • Patent number: 5491266
    Abstract: This invention relates to asymmetric syntheses in which a prochiral or chiral compound is contacted in the presence of an optically active metal-ligand complex catalyst to produce an optically active product.
    Type: Grant
    Filed: June 20, 1994
    Date of Patent: February 13, 1996
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: James E. Babin, Gregory T. Whiteker
  • Patent number: 5453547
    Abstract: A novel process for the manufacture of .gamma.-acetoxytiglic aldehyde ("C.sub.5 -aldehyde"), which is known as an important starting material for the production of vitamin A acetate from a (.beta.-ionylidenethyl)triphenylphosphonium halide and C.sub.5 -aldehyde, comprises treating a pentenyn-3-ol of the formula HC.tbd.C--C(CH.sub.3)(OH)--CH.dbd.C(R).sub.2 (II), wherein both R's signify either hydrogen or methyl, with ozone, preferably in a lower alkanol R.sup.1 OH, wherein R.sup.1 signifies C.sub.1-4 -alkyl, to obtain an aldehyde 2-hydroxy-2-methyl-3-butynal of the formula HC.tbd.C--C(CH.sub.3)(OH)--CHO (III). The aldehyde III may be converted to the C.sub.5 -aldehyde by conventional means.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: September 26, 1995
    Assignee: Hoffman-La Roche Inc.
    Inventor: Ulriche Zutter
  • Patent number: 5414154
    Abstract: A process for the reduction of methylbenzofuran (MBF) impurities in phenol obtained from the decomposition product of cumene hydroperoxide requires treating the phenol to reduce the level of acetol, contacting the phenol containing a low level of acetol with an acid resin at sufficient temperature and residence time to reduce the level of MBF by conversion to higher boiling compounds, then distilling the phenol to separate phenol from higher boiling compounds. The phenol may be treated in known ways, such as by treatment with an amine, to reduce the level of acetol. The phenol containing a low level of acetol is contacted with a strong acid resin to reduce the level MBF.
    Type: Grant
    Filed: June 6, 1994
    Date of Patent: May 9, 1995
    Assignee: AlliedSignal Inc.
    Inventors: Theodore J. Jenczewski, Lamberto Crescentini, James A. Kweeder
  • Patent number: 5414140
    Abstract: Fluorinated aldehydes are made by reacting a fluorinated acyl chloride with a silicon hydride in the presence of palladium. Also disclosed are fluorinated ether aldehydes and their polymers, a process for making fluorinated aldehydes polymers using titanium or aluminum alkoxide catalysts, and a process for endcapping fluorinated polymers using perfluoroallyl fluorosulfate or fluorine.
    Type: Grant
    Filed: January 21, 1992
    Date of Patent: May 9, 1995
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: William B. Farnham
  • Patent number: 5387720
    Abstract: A process for the production of acrolein by dehydration of glycerol in the liquid phase or in the gaseous phase, in each case on acidic solid catalysts, is described. Compared with previously known processes, the space-time yield and catalyst service life may be surprisingly increased with higher selectivity by treating a glycerol-water mixture with a glycerol content of 10 to 40 wt. % at 180.degree. to 340.degree. C. (liquid phase) or at 250.degree. to 340.degree. C. (gaseous phase) on a solid catalyst with an H.sub.o value (Hammett acidity function) of less than +2, preferably less than -3.
    Type: Grant
    Filed: November 12, 1993
    Date of Patent: February 7, 1995
    Assignee: Degussa Aktiengesellschaft
    Inventors: Armin Neher, Thomas Haas, Dietrich Arntz, Herbert Klenk, Walter Girke
  • Patent number: 5386063
    Abstract: (all-E)-2,7,-dimethylocta-2,4,6-triene-1,8-dial-.sup.13 C.sub.4 is synthesized from commercially available and relatively inexpensive starting compounds, and the key starting compound is triethyl phosphonoacetate-.sup.13 C.sub.2. The .sup.13 C labeled dial is useful as an intermediate in synthesizing .sup.13 C labeled carotenoids.
    Type: Grant
    Filed: June 16, 1993
    Date of Patent: January 31, 1995
    Assignees: The Catholic University of America, The United States of America as represented by the Secretary of Agriculture
    Inventors: Frederick Khachik, Gary R. Beecher, Betty W. Li
  • Patent number: 5371297
    Abstract: A process for the preparation of aldehydes of the general formula I ##STR1## in which R.sup.1, R.sup.2 denote hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.8 cycloalkyl, acyl, aryl, or C.sub.7 -C.sub.20 aralkyl or together stand for --(CH.sub.2).sub.n --X--(CH.sub.2).sub.m --,X denotes methylene, oxygen, sulfur, NH or NR.sub.3 andn, m stand for an integer from 0 bis 8,wherein a geminal formyl ester of the general formula II ##STR2## in which R.sup.1 and R.sup.2 have the aforementioned meanings and R.sup.3 denotes C.sub.1 -C.sub.12 alkyl, is caused to react in the presence of an acid catalyst at temperatures ranging from 150.degree. to 400.degree. C.
    Type: Grant
    Filed: September 16, 1993
    Date of Patent: December 6, 1994
    Assignee: BASF Aktiengesellschaft
    Inventor: Rolf Fischer
  • Patent number: 5364969
    Abstract: A novel and very effective method is proposed for the stabilization of a higher aliphatic compound having at least one double bond in a molecule such as the sex pheromone compounds of agricultural pest insects used for the elimination of the pest insect by the method of mating disruption. The method comprises admixing the sex pheromone compound with each a specified amount of (a) a specific phenolic compound, e.g., tert-butyl hydroquinone, di-tert-butyl hydroquinone, di-tert-amyl hydroquinone, di-tert-butyl p-cresol, methyl hydroquinone and p-methoxy phenol, as an antioxidant and (b) 2-(2'-hydroxy-3'-tert-butyl-5'-methyl phenyl)-5-chloro benzotriazole in combination.
    Type: Grant
    Filed: September 3, 1993
    Date of Patent: November 15, 1994
    Assignee: Shiu-Etsu Chemical Co., Ltd.
    Inventors: Toyohisa Sakurada, Hiroshi Suzuki, Ryuichi Saguchi
  • Patent number: 5360938
    Abstract: This invention relates to asymmetric syntheses in which a prochiral or chiral compound is contacted in the presence of an optically active metal-ligand complex catalyst to produce an optically active product.
    Type: Grant
    Filed: July 16, 1992
    Date of Patent: November 1, 1994
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: James E. Babin, Gregory T. Whiteker
  • Patent number: 5354908
    Abstract: A method for absorbing cobalt within an olefinic feedstock which comprises the steps of introducing a volatile cobalt compound and an olefinic feedstock into an absorber to form a cobalt-containing olefin mixture, withdrawing the cobalt-containing olefin mixture from the absorber, introducing at least a portion of the cobalt-containing olefin mixture into a reactor, wherein a substantial portion of the volatile cobalt compound entrained within the cobalt-containing olefin mixture decomposes to its non-volatile cobalt compound species, and recycling this mixture back to the absorber so that it can be used to further absorb volatile cobalt such that a more concentrated cobalt-containing olefin solution is formed.
    Type: Grant
    Filed: July 16, 1993
    Date of Patent: October 11, 1994
    Assignee: Exxon Chemical Patents Inc.
    Inventor: Kirk C. Nadler
  • Patent number: 5354909
    Abstract: A process for isolating 4-hydroxybutanal and 3-hydroxy-2-methylpropanal from aqueous mixtures of the isomers is disclosed. Reaction of the aqueous mixture with a hydroxy compound in the presence of an acidic catalyst and a nonpolar organic solvent gives a product aqueous solution of 3-hydroxy-2-methylpropanal and an organic solution containing a 2-oxytetrahydrofuran derived from 4-hydroxybutanal. The 4-hydroxybutanal can be regenerated by acidic hydrolysis of the 2-oxytetrahydrofuran.
    Type: Grant
    Filed: August 17, 1993
    Date of Patent: October 11, 1994
    Assignee: ARCO Chemical Technology, L.P.
    Inventors: Jeffrey A. Klang, Ann P. Lawson
  • Patent number: 5352841
    Abstract: Liquid acrolein, whose hazardous properties make handling difficult, is used to dose aqueous systems with acrolein in a biocidally effective concentration. Disclosed are agents which increase the ease and safety of acrolein handling and which are characterized by a content of 30 to 95% by weight acrolein and 5 to 70% by weight inorganic carrier materials. Silicas are the preferred carrier materials. The powdery or highly viscous mixture of substances will preferably exist in molded form and is additionally provided with a cladding that is impermeable to acrolein vapor. In dosing the aqueous systems, the agents are introduced directly in the water whereupon the acrolein is released.
    Type: Grant
    Filed: December 14, 1993
    Date of Patent: October 4, 1994
    Assignee: Degussa Aktiengesellschaft
    Inventors: Peter Werle, Werner Pahling, Martin Trageser
  • Patent number: 5344994
    Abstract: Coniferyl aldehyde can be prepared from eugenol with the aid of fungi or their constituents.
    Type: Grant
    Filed: June 11, 1993
    Date of Patent: September 6, 1994
    Assignee: Haarmann & Reimer GmbH
    Inventors: Wolf-Rainer Abraham, Hans-Adolf Arfmann
  • Patent number: 5334769
    Abstract: The present invention relates to a process for the preparation of aldehydes by hydrogen reduction of carboxylic acids, esters or anhydrides, characterized in that the reduction is conducted in the vapour phase, in the presence of a bimetallic catalyst of the ruthenium/tin type.
    Type: Grant
    Filed: October 26, 1992
    Date of Patent: August 2, 1994
    Assignee: Rhone-Poulenc Chimie
    Inventors: Rose-Marie Ferrero, Roland Jacquot
  • Patent number: 5321166
    Abstract: A process for the manufacture of aldehydes by the catalytic reduction of carboxylic acid halides with hydrogen in the presence of an alkylene oxide.
    Type: Grant
    Filed: February 18, 1993
    Date of Patent: June 14, 1994
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Hans Hilpert
  • Patent number: 5306845
    Abstract: A method for producing an aldehyde, which comprises hydrogenating a carboxylic acid or its alkyl ester with molecular hydrogen in the presence of a catalyst, wherein (1) chromium oxide of high purity having a specific surface area of at least 10 m.sup.2 /g and a total content of sodium, potassium, magnesium and calcium of not more than 0.4 wt %, is used as the catalyst, and (2) the hydrogenation reaction is conducted while maintaining the carboxylic acid or its alkyl ester at a concentration of not more than 10 vol %.
    Type: Grant
    Filed: June 28, 1993
    Date of Patent: April 26, 1994
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Toshiharu Yokohama, Naoko Fujita, Takao Maki
  • Patent number: 5278338
    Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen, hydroxy, halo, cyano, C.sub.1 to C.sub.6 linear or branched alkoxy, amino or substituted amino or the group ##STR2## is nitrile; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched haloalkyl, aralkyl, cycloalkyl, alkyl substituted cycloalkyl, C.sub.6 to C.sub.10 aryl, C.sub.1 to C.sub.6 linear or branched alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.1 to C.sub.6 alkylthio, C.sub.3 to C.sub.8 cycloalkylthio, C.sub.6 to C.sub.10 arylthio, C.sub.6 to C.sub.10 arylcarbonyl, C.sub.4 to C.sub.8 cycloalkenyl, trifluoromethyl, halo, C.sub.4 to C.sub.5 heteroaryl, C.sub.10 to C.sub.14 aryl, or biphenyl unsubstituted or substituted with methyl or halo, comprising heating said optically active carboxylic acid or ester thereof in the presence of water at a temperature of from about 40.degree. C.
    Type: Grant
    Filed: November 4, 1992
    Date of Patent: January 11, 1994
    Assignee: Ethyl Corporation
    Inventor: Rhonda L. Trace
  • Patent number: 5245093
    Abstract: A process for reacting a fluid phase (gaseous and/or liquid phase) in contact with a solid phase in a reaction zone, wherein the improvement in said process comprises reacting the fluid phase in contact with the solid phase in a horizontally-oriented fluidized bed vessel. The vessel includes at least two compartments or stages, and includes means for vibrating the vessel. The process of the present invention enables one to effect fluidization of the solid phase independently of the flow rate or velocity of the fluid phase, thus enabling proper contact time of the fluid phase with the solid phase and minimizing the amount of fluid phase reactant to be recycled.
    Type: Grant
    Filed: January 26, 1989
    Date of Patent: September 14, 1993
    Assignee: ABB Lummus Crest Inc.
    Inventor: George Ember
  • Patent number: 5241122
    Abstract: Catalysts, catalyst precursors, and catalytic systems are provided. The catalysts generally comprise a substrate that includes a group IB metal and a porous, microcrystalline layer that includes the metal and that is disposed on at least a portion of the substrate. The catalysts are prepared by providing a substrate that includes group IB metal, oxidizing said substrate in the presence of stainless steel to produce an oxide coating of said group IB metal, and reducing substantially all of said oxidized substrate.
    Type: Grant
    Filed: March 3, 1992
    Date of Patent: August 31, 1993
    Assignee: Union Camp Corporation
    Inventors: James B. Woell, John W. Catino
  • Patent number: 5239108
    Abstract: A process for producing an aliphatic or alicyclic aldehyde is disclosed, which process comprises the step of hydrogenating an aliphatic or alicyclic carboxylic acid or a derivative thereof with molecular hydrogen in the presence of a catalyst, wherein the catalyst is a zirconium oxide catalyst which contains chromium as an essential component, has a weakly basic site amount of more than 0.03 mmol/g as determined by a temperature programmed desorption method using carbon dioxide as an adsorbate in which the amount of carbon dioxide desorbed in the temperature range of from 100.degree. to 250.degree. C. is measured, and has pores having a radius of from 20 to 500 .ANG. in an amount of not less than 0.1 cc/g and pores having a radius of from 1,000 to 50,000 .ANG. in an amount of not less than 0.05 cc/g as measured with a mercury porosimeter. Aldehydes can be obtained directly from aliphatic or alicyclic carboxylic acids or derivatives thereof in high yield.
    Type: Grant
    Filed: October 20, 1992
    Date of Patent: August 24, 1993
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Toshiharu Yokoyama, Naoko Matsuyama, Takao Maki