Preparing By Reduction Or Dehydrogenation (e.g., By Hydrogenation, Etc.) Patents (Class 568/772)
  • Patent number: 4431849
    Abstract: A process for preparing a methyl phenol from a tertiary hydroperoxide in an oxidation product of an alkylbenzene of the general structural formula ##STR1## wherein R is a secondary alkyl group and n is an integer of 1 to 3, which comprises hydrogenating the oxidation product in the presence of a mineral acid medium with a hydrogenation catalyst.
    Type: Grant
    Filed: October 21, 1981
    Date of Patent: February 14, 1984
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Howard A. Colvin
  • Patent number: 4431848
    Abstract: A process is disclosed for making resorcinol and substituted resorcinols by a first reaction step of vapor-phase cyclization of a delta-keto carboxylic acid ester over a carbon catalyst bed to form a 1,3-cyclic dione intermediate. The delta-keto ester is conveyed through the catalyst bed by a vaporized carrier characterized by being liquid at 25.degree. C. and having a sufficiently high boiling point that the vaporized carrier is easily condensable under ambient conditions. In a second reaction step, a liquid solvent containing the 1,3-cyclic dione intermediate is contacted with a supported noble-metal catalyst to form resorcinol or a substituted resorcinol.
    Type: Grant
    Filed: April 26, 1982
    Date of Patent: February 14, 1984
    Assignee: Koppers Company, Inc.
    Inventor: Nicholas P. Greco
  • Patent number: 4419529
    Abstract: A 2-alkylphenol is prepared by reduction of a 2-acylphenol in the presence of a metallic catalyst. The reaction is carried out at a temperature of 80.degree. to 200.degree. C. and under a pressure of 10 to 100 bars, and a base metal, in particular copper, is used as a catalyst. It is particularly advantageous to use the catalyst in combination with a support. The hydrogenation of the acylphenol is advantageously carried out in the presence of an inert solvent. The process can be carried out continuously or discontinuously. The alkylphenols obtained are suitable for use in the synthesis of active substances having biocidal properties.
    Type: Grant
    Filed: March 3, 1982
    Date of Patent: December 6, 1983
    Assignee: Riedel-de Haen Aktiengesellschaft
    Inventor: Arthur Steinmetz
  • Patent number: 4417076
    Abstract: A catalyst for dehydrogenation of oxygen-containing derivatives of the cyclohexane series of the general formula: ##STR1## wherein R.sub.1 is hydrogen or a C.sub.1 -C.sub.4 alkyl;R.sub.2 and R.sub.3 are radicals having the same or different meanings: --H, --OH, .dbd.O, provided that R.sub.2 and R.sub.3 are not simultaneously hydrogen and R.sub.1, R.sub.2 and R.sub.3 are attached to different carbon atoms of the cycle,into corresponding cyclic ketones and/or phenols containing the following components, percent by weight:______________________________________ nickel 15 to 55 promotor-germanium and/or lead 0.2 to 8.0 inert carrier 84.8 to 37.0 ______________________________________and an atomic ratio of nickel to the promotor is within the range of from 15:1 to 410:1 respectively. The catalyst can additionally contain a salt of an alkali metal and a mineral acid in an amount of from 0.01 to 1.0% by weight.
    Type: Grant
    Filed: August 9, 1982
    Date of Patent: November 22, 1983
    Inventors: Alexandr Y. Rozovsky, Valentin D. Stytsenko, Svetlana A. Nizova, Petr S. Belov, Alexandr J. Dyakonov
  • Patent number: 4379939
    Abstract: A process for the preparation of nitrogen fertilizers, especially oxamide, either indirectly, or directly from oxalate esters, including the regeneration of the quinone oxidant utilized in the formation of the above esters.Preparation of oxalate esters as potential intermediates for nitrogen fertilizers by the oxidative carbonylation of alcohols with carbon monoxide in the presence of a catalytic amount of a platinum group metal salt with or without a corresponding metal oxidant salt and an optionally substituted quinone (substituted or unsubstituted 2,5-cyclohexadiene-1,4-dione). High yields of isolated dialkyl oxalates are obtained by regulating temperature and carbon monoxide pressure and by maintaining essentially anhydrous conditions. In addition, high yields of the hydroquinones (1,4-dihydroxybenzenes) are recovered.
    Type: Grant
    Filed: June 30, 1980
    Date of Patent: April 12, 1983
    Assignee: Tennessee Valley Authority
    Inventors: Robert J. Radel, Jack M. Sullivan
  • Patent number: 4360469
    Abstract: It has been found that unexpectedly high yields of a high purity product can be obtained when substituted p-quinones are prepared by oxidation, using a molecular oxygen-containing gas, of the corresponding phenols in an inert solvent having a dipole moment of at least 2.7 and in the presence of a salcomine catalyst.
    Type: Grant
    Filed: June 11, 1970
    Date of Patent: November 23, 1982
    Assignee: Eastman Kodak Company
    Inventors: Hans K. Dietl, Howard S. Young
  • Patent number: 4319054
    Abstract: There is disclosed a process for producing pyrogallol by dehydrogenation of cyclohexane-1,2,3-triol in the presence of a platinum group metal catalyst in an inert gas stream. The catalyst contains, as modifier, (a) at least one alkali metal salt and/or (b) at least one member selected from the group consisting of gold, tellurium, silver, arsenic, selenium, indium, antimony, bismuth, copper and zinc, with the Pd-Te catalyst being preferred. The catalyst ingredients are supported on a carrier. The process gives high selectivity of pyrogallol.
    Type: Grant
    Filed: December 8, 1980
    Date of Patent: March 9, 1982
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Takao Maki, Kenji Murayama
  • Patent number: 4310465
    Abstract: A synthesis of Vitamin E has the condensation of 2,4-pentanediene and 1,2-epoxy-2,6,10,14-tetramethylpentadecane including intermediates in this synthesis which uses base catalyzed condensations of aliphatic compounds to construct the Vitamin E molecule from aliphatic precursors.
    Type: Grant
    Filed: December 17, 1979
    Date of Patent: January 12, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Gary L. Olson, Gabriel Saucy
  • Patent number: 4288640
    Abstract: Process for carrying out exothermic reactions between a gas and a liquid in the presence of a solid catalyst by passing the gas and the liquid cocurrently through a packed reaction vessel, preferably of elongated shape, wherein the gas and liquid pass through the packed reaction vessel in transition flow.
    Type: Grant
    Filed: July 22, 1976
    Date of Patent: September 8, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Ludwig Schuster, Paul Raff, Herwig Hoffmann, Rolf Schneider, Erich Flickinger
  • Patent number: 4271091
    Abstract: Cyclohexanone and/or cyclohexanol can be oxidized in the vapor phase to phenol by contacting the cyclohexanone and/or cyclohexanol with a suitable oxidation catalyst in the presence of molecular oxygen. Suitable catalysts are solids comprising Mo, W, Sb and/or V oxides or complexes thereof. The catalysts may be promoted with additional elements.
    Type: Grant
    Filed: June 17, 1978
    Date of Patent: June 2, 1981
    Assignee: Standard Oil Company
    Inventors: Robert K. Grasselli, Dev D. Suresh
  • Patent number: 4250336
    Abstract: Resorcinols are prepared by converting .delta.-ketocarboxylic acid esters in the gaseous phase at a temperature from 250.degree. to 500.degree. C. in the presence of hydrogen at a catalyst. The catalyst consists of two components which are prepared separately and combined thereafter. The first component contains at least one compound of a metal of group VIII and/or at least one compound of a metal of group I B supported on one or several carrier materials. The second component contains at least one compound of a metal of group II A and/or IV A and/or III B and/or IV B supported on one or several carrier materials. A particularly preferred catalyst consists of a mixture of equal volume parts of platinum/charcoal as first component and of thorium/charcoal as second component.
    Type: Grant
    Filed: June 6, 1979
    Date of Patent: February 10, 1981
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Werner H. Muller, Karl E. Mack, Hansjorg Hey
  • Patent number: 4247720
    Abstract: A process for preparing -trimethylhydroquinone by contacting 3,5,5-trimethyl-2-cyclohexene-1,4-dione with an acid catalyst in the vapor phase.
    Type: Grant
    Filed: October 12, 1976
    Date of Patent: January 27, 1981
    Assignee: Rhone-Poulenc Industries
    Inventors: Michel M. Baudouin, Robert M. Perron
  • Patent number: 4235790
    Abstract: A process for separating p-benzoquinone as quinhydrone from the reaction solution obtained in the oxidation of phenol with oxygen in the presence of copper salts and of nitriles as the solvent, which comprises suspending and/or dissolving solid hydroquinone in this reaction solution, precipitating the p-benzoquinone contained therein as quinhydrone and separating it from the reaction solution.
    Type: Grant
    Filed: January 22, 1979
    Date of Patent: November 25, 1980
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Werner H. Muller, Dieter Freudenberger
  • Patent number: 4224248
    Abstract: A process has been developed for the depyrophorization of pyrophoric metal catalysts, such as Raney nickel catalysts, which comprises treating said pyrophoric metal catalysts in water and/or an organic solvent with an organic nitro compound or a nitroso compound. The catalysts which are obtained according to the process of the invention are useful for carrying out all hydrogenation reaction which can be carried out using the corresponding pyrophoric catalysts. The catalysts obtained are further distinguished by high activity and extended life. They are not contaminated by contact catalyst poisons and can be used essentially without pre-activation.
    Type: Grant
    Filed: October 17, 1978
    Date of Patent: September 23, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Udo Birkenstock, Josef Haydn
  • Patent number: 4208339
    Abstract: p-Benzoquinone is prepared by oxidizing phenol with molecular oxygen or with a gas in which oxygen is present, in the liquid phase, in the presence of cuprous or cupric ions. The improvement resides in carrying out the reaction in the presence of a metal, in the metallic form, which is selected from the group consisting of nickel, iron, tin, cobalt, chromium, molybdenum, magnesium and copper. The resultant p-benzoquinone is useful as an industrial source of hydroquinone, which is employed in photography.
    Type: Grant
    Filed: June 23, 1978
    Date of Patent: June 17, 1980
    Assignee: Rhone-Poulenc Industries
    Inventors: Michel Costantini, Michel Jouffret
  • Patent number: 4172960
    Abstract: Pyrogallol is prepared by (A) reacting a halo compound of formula ##STR1## where X represents Br or I, R.sup.1 represents hydrogen, secondary or tertiary alkyl of up to 10 carbon atoms, carboxy or alkoxycarbonyl of 2-5 carbon atoms and R.sup.2 represents hydrogen or alkyl of 1-4 carbon atoms, with an alkali metal alkoxide of formula ROM where M represents an alkali metal and R represents alkyl of 1-4 carbon atoms, to replace each X by OR, and then (B) dealkylating each OR and each OR.sup.2 where R.sup.2 represents alkyl of 1-4 carbon atoms and removing the R.sup.1 group where this is not hydrogen.
    Type: Grant
    Filed: December 20, 1977
    Date of Patent: October 30, 1979
    Assignee: Fisons Limited
    Inventors: Derek Baldwin, Peter S. Gates
  • Patent number: 4160113
    Abstract: The present invention is related to a process for the manufacture of resorcinols by catalytic dehydrogenation of cyclohexane diones-(1,3) in the liquid phase by means of a dehydrogenating mixture consisting of a solvent and of a catalyst containing a noble metal from Group VIII of the Periodic Table.
    Type: Grant
    Filed: November 11, 1977
    Date of Patent: July 3, 1979
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Werner H. Muller, Knut Riedel, Hans Krekeler
  • Patent number: 4154965
    Abstract: A two-stage process for the conversion of certain esters of delta-keto carboxylic acids to the corresponding resorcinol is described, using a first vapor phase stage for cyclization to a dihydroresorcinol followed by a second liquid phase dehydrogenation, in the presence of unconverted ester, to form the resorcinol product.
    Type: Grant
    Filed: November 1, 1977
    Date of Patent: May 15, 1979
    Assignee: Stamicarbon, B.V.
    Inventors: Peter J. N. Meijer, Annita M. F. Vanholsaet, Erik T. M. Wolters
  • Patent number: 4091225
    Abstract: This invention comprises an alkylation, reduction and transesterification process for the preparation of ester substituted phenols. The products are useful as antioxidants and may be prepared in high yields and with a high degree of purity.
    Type: Grant
    Filed: January 22, 1974
    Date of Patent: May 23, 1978
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Dane K. Parker