Preparing Esters By Dehydrogenation Of Alcohols Patents (Class 560/239)
  • Patent number: 5756830
    Abstract: A process for producing a crystalline chiral hydroxy ester of the formula: ##STR1## is disclosed. The process comprises reacting a diol of the formula: ##STR2## with an effective amount of isobutryic anhydride and an effective amount of a lipase enzyme in an effective amount of acetonitrile, said reaction being conducted at a low temperature, and wherein X.sup.1 and X.sup.2 are each independently selected from F or Cl.
    Type: Grant
    Filed: December 12, 1996
    Date of Patent: May 26, 1998
    Assignee: Schering Corporation
    Inventors: Christopher M. Nielsen, Anantha Sudhakar
  • Patent number: 5726345
    Abstract: We describe a process for perfuming fabrics washed in the presence of a lipase-containing detergent and, optionally, subsequently treated with a fabric softener, said process being characterized in that said detergent and/or said fabric softener contains a compound of formula ##STR1## wherein a. R represents a radical derived from an fragrant alcohol of formula ROH and Y represents a C.sub.7 to C.sub.24 linear or branched, saturated or unsaturated alkyl radical, or a --(CH.sub.2).sub.n COOR group wherein R is defined as above and n is an integer from 0 to 6; or p1 b. Y represents a C.sub.7 to C.sub.24 linear or branched, saturated or unsaturated alkyl radical and R represents a group of formula ##STR2## wherein, either R.sup.1 represents hydrogen and R.sup.2 represents an alkylidene radical derived from a fragrant aldehyde of formula ##STR3## or R.sup.2 represents an alkylidene radical and R.sup.1 an alkyl radical, R.sup.1 and R.sup.
    Type: Grant
    Filed: August 22, 1996
    Date of Patent: March 10, 1998
    Assignee: Firmenich S.A.
    Inventors: Walter Paget, Daniel Reichlin, Roger Leslie Snowden, Eric C. Walborsky, Christian Vial
  • Patent number: 5679837
    Abstract: The present invention relates to:(1) a novel catalyst which has a high catalytic activity, is useful in the production of acetic acid and/or methyl acetate from methanol, and is obtained through ion exchange of an anion of an anion exchanger with an anion of an Ru--Sn hetero-polynuclear compound;(2) a novel catalyst which has a high catalytic activity, is useful in the production of acetic acid and/or methyl acetate from methanol, and is obtained through ion exchange of a cation of a cation exchanger with a Ru complex and treatment with a Sn compound;(3) a process for producing acetic acid and/or methyl acetate from methanol through a one-stage reaction in a gas phase wherein the catalytic activity is maintained throughout the reaction; and(4) a process for producing acetic acid and/or methyl acetate in the presence of a highly active catalyst, for example, the catalyst specified in (1) or (2), at a high reaction rate.
    Type: Grant
    Filed: February 23, 1996
    Date of Patent: October 21, 1997
    Assignee: Daicel Chemical Industries, Ltd.
    Inventor: Sumio Shinoda
  • Patent number: 5679831
    Abstract: Process for the preparation of a terminal ester by carbonylation of an internally unsaturated organic compound in the presence of an alcohol, carbon monoxide, palladium, an acid with a pK.sub.a of less than 2 (measured at 18.degree. C. in an aqueous solution) and a bidentate organic phosphorus, antimony or arsenic ligand compound having a bridging group, wherein the bridging group comprises a bis(.eta.-cyclopentadienyl) coordination group of a transition metal.
    Type: Grant
    Filed: January 5, 1995
    Date of Patent: October 21, 1997
    Assignees: DSM N.V., E. I. Du Pont de Nemours and Company
    Inventor: Otto E. Sielcken
  • Patent number: 5670695
    Abstract: The present invention relates to a process for the preparation of 1,8-diacetoxy-3-carboxyanthraquinone, also known as diacerein, via aloin acetylation, oxidation of the acetylated product, and purification of the raw diacerein obtained by means of crystallization from 2-methoxyethanol or N,N-dimethylacetamide and optionally by dissolution of the corresponding salt with triethylamine in methylene chloride, followed by removal of the insoluble residue.
    Type: Grant
    Filed: January 23, 1995
    Date of Patent: September 23, 1997
    Assignee: Laboratoire Medidom S.A.
    Inventor: Guido Di Napoli
  • Patent number: 5659073
    Abstract: Disclosed is a method of making a glycol ether acetate. Acetic acid is reacted with a glycol ether at a molar ratio of about 1.1 to about 2, in a mixture with a catalyst and an azeotropic agent which can be either butyl acetate or dibutyl ether. The mixture is heated to a temperature and pressure sufficient to vaporize an azeotrope of water and the azeotropic agent. In another embodiment of the invention, a glycol ether acetate is made by preparing a reaction mixture of acetic acid and a glycol ether in a molar ratio of about 1.1 to about 1.2, about 5 to about 25 wt % n-butanol, an additional amount of acetic acid stoichiometric with the amount of n-butanol, and a catalyst. The reaction mixture is heated to form a glycol ether acetate, water, and butyl acetate. The azeotrope, excess acetic acid, butyl acetate, and glycol ether are successively removed by distillation.
    Type: Grant
    Filed: July 7, 1995
    Date of Patent: August 19, 1997
    Inventor: Jian Steven Qi
  • Patent number: 5618972
    Abstract: A two-stage process for effecting a chemical reaction has been developed. The reactants are contacted with a first stage fixed catalyst bed containing a solid catalyst or mixture of catalysts effective to catalyze the reaction and form a mixture of reactants and products. This reaction mixture and a desorbent are then contacted with a second stage simulated moving bed containing a solid or a mixture of solids effective to catalyze the reaction and to selectively adsorb at least one component from the reaction mixture. At least one product-containing stream is formed and collected. The process may be conducted in the liquid phase or in the vapor phase.
    Type: Grant
    Filed: February 27, 1995
    Date of Patent: April 8, 1997
    Assignee: UOP
    Inventors: Gregory A. Funk, Hemant W. Dandekar, Simon H. Hobbs
  • Patent number: 5563289
    Abstract: The present invention provides a unique and novel way of producing an acetoxystyrene. In this new process which comprises a single step, a mixture of (a) a carbinol, (b) an acetylating agent, and (c) an acid catalyst is dehydrated under suitable dehydration conditions of temperature and pressure to form said acetoxystyrene.
    Type: Grant
    Filed: October 13, 1995
    Date of Patent: October 8, 1996
    Assignee: Hoechst Celanese Corporation
    Inventors: James R. Sounik, Keith M. Russ
  • Patent number: 5527949
    Abstract: A method for making an amine includes the steps of heating a reaction mixture including a nitrile, an acid, water and a substrate compound capable of generating a carbonium ion by reaction with the acid to generate a first reaction intermediate; treating the first reaction intermediate with an acid in the presence of a primary alkanol to form a second reaction intermediate and an alkyl ester; separating the alkyl ester from the second reaction intermediate; and treating the second reaction intermediate with a base to form the amine.
    Type: Grant
    Filed: August 23, 1994
    Date of Patent: June 18, 1996
    Assignee: Rohm and Haas Company
    Inventors: Sudhir K. Agarwal, Rajiv M. Banavali, Bharati D. Chheda, Samuel F. Reed, Jr.
  • Patent number: 5463108
    Abstract: The present invention provides a unique and novel way of producing 4-acetoxystyrene. In this new process, 4-hydroxystyrene is acetylated, in the presence of an acetylation agent, under suitable conditions of temperature and pressure and for a sufficient period of time to form acetoxystyrene.
    Type: Grant
    Filed: December 19, 1994
    Date of Patent: October 31, 1995
    Assignee: Hoechst Celanese Corporation
    Inventors: James R. Sounik, William W. Wilkison, III, Keith M. Russ, Lynn Massarelli
  • Patent number: 5449793
    Abstract: A novel optically active erythro-1-alkanoyloxy-2,4-O-isopropylidene-2,4-dihydroxy-5-substituted pentane expressed by the formula ##STR1## wherein R.sup.1 represents a halogen atom or cyano group and R.sup.2 represents an alkyl group of 1 to 6 carbon atoms, and a process for producing the above compound are provided, the compound being preferably usable as an intermediate for preparing a HMG-CoA reductase inhibitor and the process being practiced under mild conditions and with a high yield.
    Type: Grant
    Filed: May 12, 1994
    Date of Patent: September 12, 1995
    Assignee: Chisso Corporation
    Inventors: Kazutoshi Miyazawa, Teruyo Sugiura, Yasuyuki Koizumi, Naoyuki Yoshida
  • Patent number: 5410072
    Abstract: Isomeric mixtures of pentanoic acids are prepared by subjecting butene-1/butene-2 mixtures to hydroformylation to form aldehyde mixtures, followed by oxidation of the aldehyde mixtures which have been separated off from the reaction product. The hydroformylation is carried out in a heterogeneous system in the presence of rhodium catalysts which are dissolved in water. The mixture of isomeric 5 carbon monocarboxylic acids produced, when esterified with polyhydric alcohols, yields mixtures of isomeric esters which are useful as lubricants for refrigerant compressors operated with chlorine-free, at least partly fluorinated hydrocarbons as the refrigerant.
    Type: Grant
    Filed: September 23, 1994
    Date of Patent: April 25, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Bahrmann, Wolfgang Greb, Georg Dambkes, Peter Heymanns, Heinz Kalbfell, Peter Lappe, Helmut Springer, Eberhard von Mulmann, Jurgen Weber, Ernst Wiebus, Carl D. Frohning, Harald Kappesser
  • Patent number: 5405991
    Abstract: A process for preparing carboxylic esters from carboxylic acid halides or carboxylic anhydrides by reacting one of these starting materials with an alcohol under the catalytic action of "onium" or metal salts of carboxylic acids to obtain high yields of products in anhydrous form in a technically simple manner. The process is especially well suited for preparing 1,1,1-trifluoroethyl trifluoroacetate.
    Type: Grant
    Filed: April 26, 1994
    Date of Patent: April 11, 1995
    Inventors: Heinz-Rudi Feist, Wilhelm Pohlmeyer, Joachim Frehse, Werner Rudolph, Max Braun, Kerstin Eichholz
  • Patent number: 5399745
    Abstract: There are disclosed a process for producing methyl formate by dehydrogenating methanol in liquid phase in the presence of a solid catalyst and a process according thereto wherein a gas (N.sub.2, H.sub.2, CO, etc.) is continuously blown into the liquid phase from outside, and the gas along with the reaction product are continuously withdrawn outside the reaction system from the gaseous phase directly or through a cooler. By virtue of the liquid-phase reaction in the above process, as compared with the conventional gaseous phase reaction, the reaction temperature can be lowered, the reaction gas rich in the objective methyl formate rather than methanol is obtained by continuously withdrawing the resultant methyl formate outside the reaction system and accordingly, a single pass yield higher than that at the thermodynamical equilibrium-value is assured, whereby energy saving is made possible.
    Type: Grant
    Filed: April 7, 1994
    Date of Patent: March 21, 1995
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Mikio Yoneoka, Takeo Ikarashi, Kumiko Watabe, Kenji Nakamura
  • Patent number: 5393919
    Abstract: The present invention relates to:(1) a novel catalyst which has a high catalytic activity, is useful in the production of acetic acid and/or methyl acetate from methanol, and is obtained through ion exchange of an anion of an anion exchanger with an anion of an Ru--Sn hetero-polynuclear compound;(2) a process for producing acetic acid and/or methyl acetate from methanol through a one-stage reaction in a gas phase wherein the catalytic activity is maintained throughout the reaction; and(3) a process for producing acetic acid and/or methyl acetate in the presence of a highly active catalyst, for example, the catalyst specified in (1), at a high reaction rate.
    Type: Grant
    Filed: March 9, 1994
    Date of Patent: February 28, 1995
    Assignee: Daicel Chemical Industries, Ltd.
    Inventor: Sumio Shinoda
  • Patent number: 5334751
    Abstract: Disclosed is a process for making ethyl acetate which comprises reacting in a reaction zone ethyanol and molecular oxygen in the presence of a solid catalyst containing the elements and proportions indicated by the empirical formulaPd.sub.a M.sub.b TiP.sub.c O.sub.x (formula 1)where M is selected from Cd, Au, Zn, Tl, alkali metals and alkalineearth metals,a is from 0.0005 to 0.2b is from zero to 3ac is 0.5 to 2.5, andx is a value sufficient to satisfy the valence requirements ofthe other elements present, andwherein said catalyst contains crystalline TiP.sub.2 O.sub.7.
    Type: Grant
    Filed: April 28, 1992
    Date of Patent: August 2, 1994
    Assignee: The Standard Oil Company
    Inventors: Michael F. Lemanski, Joseph B. Hazen, Patricia R. Blum
  • Patent number: 5274175
    Abstract: A method for producing 4-acetoxystyrene by heating 4-acetoxyphenylmethylcarbinol, with an acid catalyst, at a temperature of from about 85.degree. C. to about 300.degree. C. under a pressure of from about 0.1 mm HgA to about 760 mm HgA for from about 0.2 minutes to about 10 minutes. The process also provides for the solventless (neat) hydrogenation of 4-acetoxyacetophenone to produce 4-acetoxyphenylmethylcarbinol. The reaction proceeds by heating at 54.degree. C. to 120.degree. C. with an excess of hydrogen in the presence of a Pd/C or activated nickel such as Raney Nickel catalyst in the absence of a solvent. The 4-acetoxyphenylmethylcarbinol may then be dehydrated to 4-acetoxystyrene. The later may be polymerized to poly(4-acetoxystyrene) and hydrolyzed to poly(4-hydroxystyrene).
    Type: Grant
    Filed: June 10, 1993
    Date of Patent: December 28, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: Bakulesh N. Shah, Dung Q. Tran, Donna L. Keene
  • Patent number: 5245074
    Abstract: A method for producing 4-acetoxystyrene by heating 4-acetoxyphenylmethylcarbinol, with an acid catalyst, at a temperature of from about 85.degree. C. to about 300.degree. C. under a pressure of from about 0.1 mm HgA to about 760 mm HgA for from about 0.2 minutes to about 10 minutes. The process also provides for the solventless (neat) hydrogenation of 4-acetoxyacetophenone to produce 4-acetoxyphenylmethylcarbinol. The reaction proceeds by heating at 54.degree. C. to 120.degree. C. with an excess of hydrogen in the presence of a Pd/C or activated nickel such as Raney Nickel catalyst in the absence of a solvent. The 4-acetoxyphenylmethylcarbinol may then be dehydrated to 4-acetoxystyrene. The later may be polymerized to poly(4-acetoxystyrene) and hydrolyzed to poly(4-hydroxystyrene).
    Type: Grant
    Filed: May 21, 1992
    Date of Patent: September 14, 1993
    Inventors: Bakulesh N. Shah, Dung Q. Tran, Donna L. Keene
  • Patent number: 5218134
    Abstract: Esters are prepared directly from 2-substituted alcohols, such as Guerbet alcohols, by dehydrogenating and esterifying the alcohol at 170.degree. C.-240.degree. C. in the presence of a catalyst system comprising (i) platinum on activated carbon, zinc oxide or zinc C.sub.2 -C.sub.20 carboxylate and (ii) NaOH, KOH or LiOH. Mixed esters may also be prepared from appropriate mixtures of 2-substituted alcohols.
    Type: Grant
    Filed: September 23, 1992
    Date of Patent: June 8, 1993
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Roy L. Pruett, Edmund J. Mozeleski
  • Patent number: 5194675
    Abstract: Methyl formate is prepared by converting methanol over a copper-containing catalyst at elevated temperatures and in the gas phase by a process in which the catalyst used contains from 30 to 80% by weight of copper, calculated as CuO, as well as from 20 to 70% by weight of a magnesium silicate, calculated as MgO plus SiO.sub.2, which has a molar ratio of MgO/SiO.sub.2 of from 0.3 to 1.5, and may additionally be doped with the metals zinc, chromium and/or barium, each in an amount of not more than 1.5% by weight, calculated as ZnO, Cr.sub.2 O.sub.3 and BaO.
    Type: Grant
    Filed: January 9, 1992
    Date of Patent: March 16, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Joerg, Franz-Josef Mueller, Matthias Irgang, Laszlo Marosi, Gerhard Borchert
  • Patent number: 5151546
    Abstract: A method for producing 4-acetoxystyrene by heating 4-acetoxyphenylmethylcarbinol, with an acid catalyst, at a temperature of from about 85.degree. C. to about 300.degree. C. under a pressure of from about 0.1 mm HgA to about 760 mm HgA for from about 0.2 minutes to about 10 minutes. The process also provides for the solventless (neat) hydrogenation of 4-acetoxyacetophenone to produce 4-acetoxyphenylmethylcarbinol. The reaction proceeds by heating at 54.degree. C. to 120.degree. C. with an excess of hydrogen in the presence of a Pd/C or activated nickel such as Raney Nickel catalyst in the absence of a solvent. The 4-acetoxyphenylmethylcarbinol may then be dehydrated to 4-acetoxystyrene. The later may be polymerized to poly(4-acetoxystyrene) and hydrolyzed to poly(4-hydroxystyrene).
    Type: Grant
    Filed: October 15, 1990
    Date of Patent: September 29, 1992
    Assignee: Hoechst Celanese Corporation
    Inventors: Bakulesh N. Shah, Dung Q. Tran, Donna L. Keene
  • Patent number: 5144062
    Abstract: A process for the preparation of methyl formate by the vapor phase dehydrogenation of methanol in the presence of a catalyst composed of copper oxide, a chromium oxide and a sodium compound is described.
    Type: Grant
    Filed: September 7, 1990
    Date of Patent: September 1, 1992
    Assignee: Dairen Chemical Corporation
    Inventors: Shien-Chang Chen, Wan-Jy Cheng, Fu-Shen Lin, Fu-Juh Huang
  • Patent number: 5072025
    Abstract: 3-substituted-4-hydroxy- and 4-acetoxystyrene compounds, especially 3,5-di(methyl, bromo or chloro)-4-acetoxystyrene as well as a process for its preparation. 2,6-dimethylphenol is acylated with acetic anhydride and HF catalyzed to produce 3,5-dimethyl-4-hydroxy-acetophenone. After subsequent esterification with acetic anhydride and catalyzed hydrogenation to form 1-(3',5'-dimethyl-4'-acetoxyphenyl)ethanol, this intermediate is then dehydrated with an acid and a polymerization inhibitor to produce 3,5-dimethyl-4-acetoxystyrene.
    Type: Grant
    Filed: July 26, 1990
    Date of Patent: December 10, 1991
    Assignee: Hoechst Celanese Corporation
    Inventors: Richard Vicari, Mohammad Aslam, Wilson B. Ray, Kenneth G. Davenport, Ralph Dammel, Juergen Lingnau, Karl-Friedrich Doessel
  • Patent number: 5041614
    Abstract: A method for the preparation of 4-acetoxystyrene is disclosed. The method comprises heating 4'-acetoxyphenylmethylcarbinol in the presence of a suitable acid anhydride and a suitable dehydration catalyst in a continuous feed reaction mode to make the 4-acetoxystyrene.
    Type: Grant
    Filed: July 3, 1990
    Date of Patent: August 20, 1991
    Assignee: Hoechst Celanese Corporation
    Inventors: Mohammad Aslam, Charles B. Hilton
  • Patent number: 4965400
    Abstract: 3-substituted-4-hydroxy- and 4-acetoxystyrene compounds, especially 3,5-di(methyl, bromo or chloro)-4-acetoxystyrene as well as a process for its preparation. 2,6-dimethylphenol is acylated with acetic anhydride and HF catalyzed to produce 3,5-dimethyl-4-hydroxy-acetophenone. After subsequent esterification with acetic anhydride and catalyzed hydrogenation to form 1-(3',5'-dimethyl-4'-acetoxyphenyl)ethanol, this intermediate is then dehydrated with an acid and a polymerization inhibitor to produce 3,5-dimethyl-4-acetoxystyrene.
    Type: Grant
    Filed: August 2, 1988
    Date of Patent: October 23, 1990
    Inventors: Richard Vicari, Mohammad Aslam, Wilson B. Ray, Kenneth G. Davenport, Ralph Dammel, Juergen Lingnau, Karl-Friedrich Doessel
  • Patent number: 4939292
    Abstract: Esters are prepared by contacting, under suitable reaction conditions, a feed stream comprising a primary alcohol of 1-4 carbon atoms per molecule (preferably methanol, ethanol) and carbon monoxide with a catalyst composition comprising (a) copper or a copper compound (preferably CuO), (b) zinc oxide, (c) at least one metal or compound of at least one metal selected from the group consisting of cobalt, ruthenium, iridium, platinum, molybdenum, and rhenium (preferably cobalt and/or rhenium) and, optionally, (d) alumina.
    Type: Grant
    Filed: October 2, 1985
    Date of Patent: July 3, 1990
    Assignee: Phillips Petroleum Company
    Inventors: David J. Elliott, Filippo Pennella
  • Patent number: 4935538
    Abstract: The process for the production of high molecular weight oxygenates by condensing low molecular weight oxygenates in the presence of CO and a catalyst having the general formula A.sub.a CuM.sub.c X.sub.d O.sub.x. In addition, a novel condensation catalyst comprising A.sub.a CuM.sub.c Bi.sub.d O.sub.x is disclosed for use in this process.
    Type: Grant
    Filed: April 23, 1987
    Date of Patent: June 19, 1990
    Assignee: The Standard Oil Company
    Inventors: John R. Budge, Senja V. Compton
  • Patent number: 4906772
    Abstract: A process is disclosed for the co-production of aliphatic monocarboxylic acids and polycarboxylic aromatic acids in high selectivity, conversion and yield. The aliphatic monocarboxylic acid can serve as a component of the solvent for the process.
    Type: Grant
    Filed: December 2, 1988
    Date of Patent: March 6, 1990
    Assignee: Amoco Corporation
    Inventors: Calvin T. Chew, Rosemary F. McMahon, Kristi A. Fjare, Wayne P. Schammel
  • Patent number: 4851569
    Abstract: Methyl formate is produced continuously by reacting methanol in the liquid phase with molecular oxygen in the presence as catalyst of a soluble chromium compound which can be deliberately added or can result from corrosion of a reaction vessel fabricated in stainless steel or other chromium-containing metal alloy. Initiation of the oxidation can be accomplished by feeding a material more susceptible to oxidation than methanol, either with or without methanol, and optionally in the presence of a soluble chromium compound.
    Type: Grant
    Filed: June 4, 1985
    Date of Patent: July 25, 1989
    Assignee: BP Chemicals Limited
    Inventors: David J. Drury, John Pennington
  • Patent number: 4778923
    Abstract: Methyl formate is prepared from methanol by contacting the methanol at elevated temperature with a platinum group metal catalyst in the absence of an added hydrogen acceptor.
    Type: Grant
    Filed: September 2, 1986
    Date of Patent: October 18, 1988
    Assignee: BP Chemicals Limited
    Inventors: Richard P. Aplin, Peter M. Maitlis, Thomas A. Smith
  • Patent number: 4480122
    Abstract: A process for producing methyl formate is described by the dehydrogenation of methanol over a catalyst produced by reducing a precursor comprising copper oxide and a spinel structure support comprising the oxides of zinc and aluminum, said precursor containing 10 to 80 percent copper.
    Type: Grant
    Filed: September 27, 1982
    Date of Patent: October 30, 1984
    Assignee: Celanese Corporation
    Inventors: Theodore Horlenko, Adolfo Aguilo
  • Patent number: 4436835
    Abstract: Disclosed is a process for the preparation of a catalyst for the synthesis of methyl formate by dehydrogenating methanol in the gaseous phase, said process being characterized in that (A) at least one phosphate selected from the group consisting of copper phosphates, zinc phosphates and aluminum phosphates, and (B) at least one chloride selected from the group consisting of copper chlorides, zinc chloride, aluminum chloride, alkali metal chlorides and alkaline earth metal chlorides and/or (C) at least one compound selected from the group consisting of alkali metal compounds (exclusive of halides) and alkaline earth metal compounds (exclusive of halides) are added to copper oxide, zinc oxide and aluminum oxide.The catalyst obtained according to this process has a high activity for preparing methyl formate by dehydrogenating methanol in the gaseous phase, and this catalyst is excellent in the heat resistance and durability and has a high mechanical strength.
    Type: Grant
    Filed: March 22, 1983
    Date of Patent: March 13, 1984
    Assignee: Mitsubishi Gas Chemical Company Inc.
    Inventors: Shigeru Horie, Yasuo Yamamoto, Takeo Ikarashi
  • Patent number: 4319037
    Abstract: A process for producing methyl formate which comprises dehydrogenating methanol in vapor phase in the presence as a catalyst of copper and at least one element selected from the group consisting of elements of Group IIIA (including the rare earths) of the periodic table, of Group IVA and of the actinides is disclosed.
    Type: Grant
    Filed: August 31, 1978
    Date of Patent: March 9, 1982
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventor: Mikio Yoneoka
  • Patent number: 4232171
    Abstract: A process for producing methyl formate which comprises dehydrogenating methanol in the vapor phase in the presence of a catalyst containing copper and a cement is disclosed.
    Type: Grant
    Filed: April 10, 1979
    Date of Patent: November 4, 1980
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Mikio Yoneoka, Minoru Osugi, Takeo Ikarashi
  • Patent number: 4220803
    Abstract: A process for producing acetic acid and acetaldehyde from ethanol which comprises contacting a mixture of ethanol and oxygen with a supported copper oxide catalyst essentially free of barium, the mole ratio of oxygen to ethanol being from about 0.1 to about 0.5.
    Type: Grant
    Filed: June 27, 1978
    Date of Patent: September 2, 1980
    Assignee: Union Carbide Corporation
    Inventors: Arthur E. Marcinkowsky, Joseph P. Henry
  • Patent number: 4149009
    Abstract: A process for producing methyl formate which comprises dehydrogenating methanol in vapor phase in the presence as a catalyst of copper, zirconium and zinc and optionally aluminum is disclosed.
    Type: Grant
    Filed: November 21, 1977
    Date of Patent: April 10, 1979
    Assignee: Mitsubishi Gas Chemical Co., Inc.
    Inventors: Mikio Yoneoka, Minoru Osugi
  • Patent number: 4126748
    Abstract: In an improved process for the production of carboxylic acid esters by catalytic oxidation of alcohols in the liquid phase, primary alcohols of 1-4 carbon atoms are oxidized with molecular oxygen at temperatures of about 100.degree.-250.degree. C. in the presence of catalytic amounts of a compound of Co, Mn, Cr, or Fe, and an acid having a first dissociation constant K.sub.1 greater than 10.sup.-3, dissolved in the reaction mixture.
    Type: Grant
    Filed: March 25, 1977
    Date of Patent: November 21, 1978
    Assignee: Chemische Werke Huels, A.G.
    Inventors: Bernhard Scholz, Fritz Obenaus, Gerhard Franz, Hans-Jurgen Erberich, Heinz-Otto Reitemeyer