Preparing By Reduction (e.g., By Hydrogenation, Etc.) Patents (Class 568/814)
  • Patent number: 4990690
    Abstract: An industrially meritorious process for preparing aromatic polyhydric alcohol is disclosed. The process can give an extremely high conversion rate of raw material, i.e., aromatic carboxylic acid ester, and an extremely high selectivity to the objective compound. The process comprises catalytic hydrocracking of an aromatic carboxylic acid ester in which an improvement resides in the fact that an ester represented by the general formula Ar(COOR).sub.m, (CH.sub.2 OH).sub.n, (wherein Ar means an aromatic group, R is independently selected from normal and branched alkyl groups having at least 6 carbon atoms, m' means an integer of at least 1, n' means zero or a positive integer and m'+n' satisifies the relationship m'+n'.gtoreq.2) is used as raw material. An aromatic polyhydric alcohol is a very useful material, especially as a raw material for the preparation of polymeric substances having high heat resistance.
    Type: Grant
    Filed: May 11, 1989
    Date of Patent: February 5, 1991
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Yuji Onda, Fumisada Kosuge, Masaru Tunoda
  • Patent number: 4985572
    Abstract: An alcohol and/or a carboxylic acid ester is produced from a carboxylic acid or anhydride thereof by reacting the acid or anhyride with hydrogen at elevated temperature in the presence as catalyst of a composition comprising an alloy of (i) at least one noble metal of Group VIII of the Periodic Table and (ii) at least one metal capable of alloying with the Group VIII noble metal, optionally including a support and at least one of the metals rhenium, tungsten or molybdenum. The process is particularly applicable to the hydrogenation of monobasic acids, for example acetic acid, and the hydrogenation of maleic acid or maleic anhydride to gamma-butyrolactone.
    Type: Grant
    Filed: November 21, 1988
    Date of Patent: January 15, 1991
    Assignees: The British Petroleum Company, p.l.c., BP Chemicals Limited
    Inventors: Melanie Kitson, Peter S. Williams
  • Patent number: 4982016
    Abstract: Synthesis of 2-phenyl-1,3-propanediol by the selective reduction of diethyl phenylmalonate with metal hydrides in solution with heterocyclic ethers are disclosed.
    Type: Grant
    Filed: June 6, 1989
    Date of Patent: January 1, 1991
    Assignee: Carter-Wallace, Inc.
    Inventor: Young M. Choi
  • Patent number: 4973768
    Abstract: Unsaturated alcohols are prepared by hydrogenation of the corresponding carbonyl compounds in the presence of a platinum-cobalt bi-metallic catalyst having an alloy structure.
    Type: Grant
    Filed: March 6, 1989
    Date of Patent: November 27, 1990
    Assignee: Rhone-Poulenc Sante
    Inventors: Georges Cordier, Pierre Fouilloux, Jean-Michel Grosselin
  • Patent number: 4968668
    Abstract: 2-Methyl-3-(3-methylphenyl)-propan-1-ol, 2-methyl-3-(3,5-dimethylphenyl)-propan-1-ol, 1-(3-methylphenyl)-2-methylbutan-3-ol and 1-(3,5-dimethylphenyl)-2-methylbutan-3-ol, their preparation and use as fragrances.
    Type: Grant
    Filed: August 7, 1989
    Date of Patent: November 6, 1990
    Assignee: Consortium fur Elektrochemische Industrie GmbH
    Inventors: Walter Hafner, Walter Gebauer, Marlies Regiert, Wilhelm Friedrich, Erich Markl
  • Patent number: 4957986
    Abstract: Partially fluorinated polyesters are disclosed having increased biodegradability and water repellency. The incorporation of an ester group into the backbone of the partially fluorinated compound permits modification of the compound's physical properties.
    Type: Grant
    Filed: December 15, 1989
    Date of Patent: September 18, 1990
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Harry N. Cripps
  • Patent number: 4943667
    Abstract: Phenylethanols of the formula ##STR1## where R is hydrogen, alkyl of from 1 to 4 carbon atoms, alkoxy of from 1 to 4 carbon atoms, fluorine, trifluoromethyl or trifluoromethoxy, are prepared by reacting epoxides of the formula ##STR2## where R is as defined above, in the presence of hydrogen over zeolites and/or phosphates, doped with hydrogenating metal as catalysts, preferably over zeolites of the pentasil type.
    Type: Grant
    Filed: January 13, 1989
    Date of Patent: July 24, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer
  • Patent number: 4943652
    Abstract: There is disclosed a process for asymmetrically reducing a carbonyl compound, which comprises reducing the carbonyl compound by the use of a reducing agent comprising (i) an optically active tartaric acid or ester thereof and (ii) a metal borohydride, thereby producing an optically active hydroxyl compound. The process can be used for the production of optically active hydroxyesters and alcohols from ketoesters and ketones. These products are useful for the production of medicaments and liquid crystals.
    Type: Grant
    Filed: November 14, 1988
    Date of Patent: July 24, 1990
    Assignee: Ajinomoto Co., Inc.
    Inventors: Masanobu Yatagai, Takashi Ohnuki
  • Patent number: 4939307
    Abstract: A process for hydrogenation of esters of the formula: ##STR1## wherein R.sub.1 represents hydrogen or a hydrocarbyl group, wherein R.sub.2 and R.sub.4 represent a hydrocarbyl group, and wherein R.sub.3 represents a hydrocarbylene group, which process comprises contacting said ester with hydrogen and carbon monoxide in the presence of a catalyst system which comprises:(a) a compound containing a cation of an element selected from Group VIII of the Periodic Table of the Elements,(b) an alcoholate of an alkali metal and/or alkaline earth metal, and(c) an alcohol.
    Type: Grant
    Filed: February 23, 1989
    Date of Patent: July 3, 1990
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Willem W. Jager
  • Patent number: 4929773
    Abstract: A method is provided for the production of 1-(4'-isobutylphenyl)ethanol (IBPE) comprising hydrogenating 4-isobutylacetophenone (IBAP) in the absence of a solvent using as a catalyst a treated activated sponge nickel catalyst, e.g., Raney nickel, obtained by subjecting such a catalyst wetted with a protective liquid composed preponderantly of water to a washing treatment with an organic washing liquid in which the aqueous protective liquid is substantially soluble and which is substantially soluble in IBAP or IBPE, e.g., a lower alkanol such as methanol, ethanol or isopropanol. The catalyst optionally may also be washed with IBAP or IBPE after the wash with the organic washing liquid and before being used in the hydrogenation reaction. The washing treatment results in substantially higher conversions IBAP and increased yields of IBPE with a practical reaction time.
    Type: Grant
    Filed: September 7, 1988
    Date of Patent: May 29, 1990
    Assignee: Hoechst Celanese Corporation
    Inventor: Debra A. Ryan
  • Patent number: 4918248
    Abstract: An alcohol is effective produced by catalytically reducing an organic carboxylic acid ester with hydrogen in the presence of a catalyst obtained by reducing a catalyst precursor comprising (A) copper oxide and (B) titanium oxide and/or titanium hydroxide at a weight ratio of (A) to (B) in the range between 15/85 and 65/35. The component (A) may be alternatively a composite metal oxide comprises copper oxide and up to 20 wt. % of zinc oxide.
    Type: Grant
    Filed: May 22, 1989
    Date of Patent: April 17, 1990
    Assignee: Kao Corporation
    Inventors: Yasuyuki Hattori, Noriaki Fukuoka, Shigeru Tamura, Kunizo Hashiba, Kiyoshi Tsukada, Makoto Misono
  • Patent number: 4912265
    Abstract: A process for the reduction of carbonyl compounds by an alkali or alkaline-earth metal borohydride in the presence of a phase transfer catalyst which is an N-benzyl-N,N-bis (2-hydroxyethyl)cocoammonium halide.
    Type: Grant
    Filed: August 26, 1988
    Date of Patent: March 27, 1990
    Assignee: Akzo America Inc.
    Inventor: Ralph Franklin
  • Patent number: 4886919
    Abstract: A process for the gas phase hydrogenation of unsaturated trisubstituted monoesters to the saturated trisubstituted alcohols using a Zn.sub.a Cu.sub.b X.sub.c Ni.sub.d O.sub.e reduced catalyst.
    Type: Grant
    Filed: November 25, 1987
    Date of Patent: December 12, 1989
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventors: Ernesto Vera-Castaneda, John E. Logsdon
  • Patent number: 4885409
    Abstract: Process for the hydrogenation of bis-phenols by reacting bis-phenols with hydrogen in the presence of a catalytic system consisting of palladium supported on activated carbon.
    Type: Grant
    Filed: May 4, 1988
    Date of Patent: December 5, 1989
    Assignee: Montedison S.p.A.
    Inventors: Andrea Gardano, Francesco Casagrande, Marco Foa, Guido Petrini, Riccardo Barisone, Lawrence Chapoy
  • Patent number: 4880937
    Abstract: An alcohol compound is produced by reducing a carboxylic acid or an ester thereof with an alcohol in the presence of a solid catalyst. The catalyst includes a hydrous metal oxide belonging to Group IV of the Periodic Table.
    Type: Grant
    Filed: February 18, 1988
    Date of Patent: November 14, 1989
    Assignee: Japan Tobacco, Inc.
    Inventors: Hajime Matsushita, Makoto Shibagaki, Kyoko Takahashi
  • Patent number: 4879389
    Abstract: New chiral phosphinopyrrolidine compounds of the general formula: ##STR1## wherein R.sup.1 is a hydrogen atom, --COR, --COOR, --CONHR or --SO.sub.2 --R where R is an alkyl or aryl group, R.sup.2 and R.sup.3 each represents independently an aryl group which may have a substituent or substituents, and R.sup.4 and R.sup.5 each represents independently an aliphatic or cycloaliphatic hydrocarbyl group which may have a substituent or substituents, as well as the use of these compounds as ligand for a metal complex catalyst for asymmetric synthesis of optically active compounds. The new chiral phosphinopyrrolidine compounds are useful ligands which attain both of high optical yield and high reaction efficiency in catalytic asymmetric reduction.
    Type: Grant
    Filed: June 25, 1987
    Date of Patent: November 7, 1989
    Inventor: Kazuo Achiwa
  • Patent number: 4877909
    Abstract: A process for reducing an aldehyde or ketone in the presence of a stable, highly active catalyst which is insoluble in a solvent and which can be recovered easily from the reaction system after completion of the reaction and used repeatedly, characterized in that an aldehyde or ketone having a carbonyl group is reacted with an alcohol in the presence of hydrous zirconium oxide as the catalyst.
    Type: Grant
    Filed: February 22, 1988
    Date of Patent: October 31, 1989
    Assignee: Japan Tobacco, Inc.
    Inventors: Sigenobu Mizusaki, Hajime Matsushita, Shigeo Ishiguro, Hiroshi Ichinose, Akira Izumi
  • Patent number: 4877908
    Abstract: Chiral phosphorus-containing ligands comprising at least one amine radical and at least one dihydrocarbylphosphinoxy radical of the formula W=OP (R).sub.2, in which R is a hydrocarbon radical selected from the group consisting of alkyl, aryl, and cycloalkyl radicals, wherein the ligand is selected from the group consisting of:those of the formula ##STR1## those of the formula ##STR2## those of the formula ##STR3## those of the formula ##STR4## in which formulae: R.sub.1 and R.sub.2 are selected from the group consisting of a hydrogen atom and hydrocarbon radicals;R.sub.3 and R.sub.4, which must be different from one another, are selected from the group consisting of a hydrogen atom and hydrocarbon radicals that may or may not carry at least one functional group selected from the group consisting of the alcohol, thiol, thioether, amine, imine, acid, ester, amide, and ether functional groups; andR.sub.5 and R.sub.
    Type: Grant
    Filed: October 13, 1987
    Date of Patent: October 31, 1989
    Assignee: Norsolor
    Inventors: Michele Petit, Andre Mortreux, Francis Petit, Gerard Buono
  • Patent number: 4868345
    Abstract: A process for the hydrogenation of esters into alcohols which comprises converting esters of the formula ##STR1## wherein R.sub.1 is hydrogen or a hydrocarbyl group and preferably an alkyl group containing 1-20 carbon atoms or an aryl alkyl group containing 1-6 carbon atoms in the alkyl residue, the aryl being preferably phenyl, and R.sub.2 is a hydrocarbyl group as specified hereinbefore for R.sub.1, in the presence of hydrogen and carbon monoxide and a catalyst system, obtainable by combining the following components(a) a hydride of an alkali metal and/or a hydride of an alkaline earth metal,(b) an alcohol or an alkali metal and/or alkaline earth metal alcoholate thereof, and(c) a compound containing a cation of an element of Group VIII of the Periodic Table of the Elements,and allowing these components to react.
    Type: Grant
    Filed: August 31, 1988
    Date of Patent: September 19, 1989
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4866181
    Abstract: A process for preparing optically active alcohols by reducing ketones using mono- or diisopinocampheylhaloboranes as reducing agents.
    Type: Grant
    Filed: December 17, 1987
    Date of Patent: September 12, 1989
    Assignee: Aldrich-Boranes, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4783559
    Abstract: Disclosed is a process of reduction of aldehydes or ketones by means of reaction with alcohols, in the presence of a catalyst, to produce alcohols which correspond to said respective aldehyde or ketone. A solid of partially dehydrated one or more metal hydroxides whose metal is selected from the group consists of titanium, tin, ion, aluminium, cerium, and niobium is used as the catalyst. This process can be conducted either in a gas phase or in a liquid phase.
    Type: Grant
    Filed: March 25, 1987
    Date of Patent: November 8, 1988
    Assignee: Japan Tobacco Inc.
    Inventors: Hajime Matsushita, Kyoko Takahashi, Makoto Shibagaki
  • Patent number: 4731488
    Abstract: A catalyst for vapor-phase hydrogen transfer reaction between a carbonyl compound having an alkenyl or aryl group and a primary or secondary alcohol, said catalyst having a composition represented by the following general formulaMg.sub.a X.sub.b Y.sub.c O.sub.dwherein X represents at least one element selected from the group consisting of boron, aluminum, silicon, phosphorus, titanium, vanadium, iron, yttrium, zirconium, niobium, tin, antimony, lead, bismuth, lanthanum and cerium, Y represents at least one element selected from the group consisting of alkali metals and alkaline earth metals excepting magnesium, O represents oxygen, and a, b, c and d represent the atomic ratios of the individual elements, and when a is 1, b represents a number of 0.01 to 0.5, c represents a number of 0 to 0.5, and d is a number determined by the atomic valences and atomic ratios of the individual elements.
    Type: Grant
    Filed: June 6, 1986
    Date of Patent: March 15, 1988
    Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.
    Inventors: Yuuji Shimasaki, Youichi Hino, Michio Ueshima
  • Patent number: 4720597
    Abstract: For the selective production of hydroxymethylcyclopropane, cyclopropanecarboxylic acid esters are hydrogenated in the presence of a Zn chromite catalyst in the sump phase or trickling phase under a hydrogen pressure of 200-320 bar and at temperatures of 200.degree.-350.degree. C. Preferably, cyclopropanecarboxylic acid esters are used, the alcohol component of which contains 1-10, especially 1-8 carbon atoms.
    Type: Grant
    Filed: October 24, 1986
    Date of Patent: January 19, 1988
    Assignee: Huels Aktiengesellschaft
    Inventors: Werner Otte, Rudolf Nehring
  • Patent number: 4650898
    Abstract: Described are 2-methyl-4-phenyl-1-pentanol derivatives defined according to the structure: ##STR1## wherein R represents hydrogen or acetyl and uses thereof in augmenting or enhancing the aroma or taste of consumable materials including perfume compositions, colognes, perfumed articles, foodstuffs, chewing gums, medicinal products and chewing tobaccos.
    Type: Grant
    Filed: December 14, 1984
    Date of Patent: March 17, 1987
    Assignee: International Flavors & Fragrances Inc.
    Inventor: John B. Hall
  • Patent number: 4628130
    Abstract: The invention has as an object the production of alcohols by hydrogenolysis of carboxylic acid esters, under hydrogen pressure, in the presence of a catalyst resulting from the incorporation of at least one compound of at least one metal from the group consisting of germanium, tin and lead to Raney nickel or to a nickel-containing carrier. The reaction is preferably conducted at a temperature from 180.degree. to 330.degree. C. and under a pressure from 1 to 10 MPa.
    Type: Grant
    Filed: August 8, 1985
    Date of Patent: December 9, 1986
    Assignee: Institut Francais du Petrole
    Inventors: Jean-Paul Bournonville, Jean-Pierre Candy, Gil Mabilon
  • Patent number: 4625049
    Abstract: A process for the preparation of carboxylic acids, alcohols, aldehydes or the secondary products thereof which comprises reacting an alcohol having from one to about twenty carbon atoms with hydrogen and carbon monoxide in the presence of a heterogeneous sulfided catalyst comprising nickel in admixture with a co-catalyst selected from the elements of Groups V-B, VI-B and the Actinide series of the Periodic Table.
    Type: Grant
    Filed: June 30, 1982
    Date of Patent: November 25, 1986
    Assignee: Chevron Research Company
    Inventor: Steven P. Current
  • Patent number: 4598058
    Abstract: Molded catalyst materials contain metallic cobalt and/or nickel particles and a lubricant, the said particles being obtained by reduction of cobalt oxide and/or nickel oxide particles containing less than 0.1% by weight of alkali metal oxides and/or alkaline earth metal oxides at .ltoreq.500.degree. C., and the molded catalyst material having an indentation hardness greater than 300 kp/cm.sup.2.
    Type: Grant
    Filed: January 31, 1985
    Date of Patent: July 1, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Frank, Gerald Neubauer, Paul Duffner, Hans J. Wilfinger
  • Patent number: 4548810
    Abstract: Compositions obtained by reacting a tertiary amine having at least one long-chain group with a long-chain acid are disclosed. The compositions are useful in non-irritating skin or hair-contacting compositions, such as shaving creams, hair conditioners, skin conditioners, and aftershave. The compositions are also useful in non-irritating soap and dishwashing compositions. The compositions provide a combination of properties such as long-lasting slip, lubrication, emolliency, softening, and conditioning.
    Type: Grant
    Filed: May 8, 1981
    Date of Patent: October 22, 1985
    Inventor: Albert Zofchak
  • Patent number: 4546208
    Abstract: Described is a method for producing the compound defined according to the structure: ##STR1## as well as optical isomers thereof having the structures: ##STR2## as well as uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles such as perfumed polymers and solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions and fabric softener articles. Also described are processes and compositions for use in perfume aroma augmenting, enhancing, modifying and altering compositions and as perfume, cologne and perfumed article aroma imparting compositions of mixtures of the compound having the structure: ##STR3## taken further together with one or more butanoyl cyclohexane derivatives and/or 3-methyl-1-phenyl-pentanol-5. The process for preparing the compound having the structure: ##STR4## involves a one-step reaction wherein the compound having the structure: ##STR5## is hydrogenated in the presence of acid.
    Type: Grant
    Filed: March 14, 1984
    Date of Patent: October 8, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Wilhelmus J. Wiegers, Mark A. Sprecker
  • Patent number: 4511743
    Abstract: Process for the homologation of an alcohol wherein a ketal of the alcohol is reacted with hydrogen and carbon monoxide in the presence of a cobalt carbonyl complex and the resultant product is hydrolyzed to yield the aldehyde with one more carbon atom.
    Type: Grant
    Filed: November 4, 1983
    Date of Patent: April 16, 1985
    Assignee: Institut Francais du Petrole
    Inventors: Claude Seite, Dominique Commereuc, Yves Chauvin
  • Patent number: 4507510
    Abstract: Xylyleneglycol is produced by diazotization reaction of xylylenediamine in the presence of more than 5 parts by weight of water per 1 part of xylylenediamine, while maintaining the PH of the reaction mixture in the range of 1.5 to 5.0.
    Type: Grant
    Filed: December 28, 1983
    Date of Patent: March 26, 1985
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Shigeo Yoshinaka, Tsukasa Toki, Tomoji Tsuji, Seiji Uchiyama
  • Patent number: 4493801
    Abstract: Tertiary alcohols are prepared by oxidizing tertiary aldehydes with oxygen at elevated temperatures.The tertiary alcohols prepared in this way are valuable and versatile intermediates for dyes, drugs and crop protection agents and are used, for example, in the preparation of agrochemicals.
    Type: Grant
    Filed: November 2, 1981
    Date of Patent: January 15, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Gerhard Nestler
  • Patent number: 4486607
    Abstract: The invention relates to a process for the production of 3 (alkyl phenyl) propanals; certain of which are known to be valuable in the perfumery industry. The process enables this group of chemicals to be produced more easily as compared to known processes for their production. In a preferred embodiment in one step of the process the alkylation of the 3 phenyl propanol is carried out under controlled conditions so as to favor the production of para isomer of the product.
    Type: Grant
    Filed: July 12, 1982
    Date of Patent: December 4, 1984
    Assignee: Bush Boake Allen Limited
    Inventor: David Webb
  • Patent number: 4482760
    Abstract: 1,2-Diols of the formula: ##STR1## where R.sub.1 and R.sub.2 are hydrogen, alkyl of 1 to 10 carbon atoms or such as alkyl substituted by a halogen, a hydroxy group, a phenyl group, a methoxy group, or an ethoxy group, a phenyl group or a furyl group or R.sub.1 and R.sub.2 together form an alkylene group of 2 to 7 carbon atoms are formed by hydrogenating a correspondingly substituted cyanohydrin in an aqueous medium first in the presence of a hydrogenation catalyst and an acid at a temperature between -20.degree. and +25.degree. C. and a hydrogen pressure of less than 10 bar until per mole of cyanohydrin employed there is taken up one mole of hydrogen and then the hydrogenation continued to the end of the absorption of hydrogen in the presence of metallic nickel at a temperature between 30.degree. and 100.degree. C. and a hydrogen pressure between 10 and 150 bar.
    Type: Grant
    Filed: November 16, 1983
    Date of Patent: November 13, 1984
    Assignee: Degussa Aktiengesellschaft
    Inventors: Axel Kleemann, Klaus Deller, Karlheinz Drauz, Bernd Lehmann
  • Patent number: 4480115
    Abstract: This invention provides an improved process for direct hydrogenation of a carboxylic acid to its corresponding alcohol with synthesis gas in the presence of a homogeneous catalyst comprising a ruthenium compound and a Lewis Acid metal halide.
    Type: Grant
    Filed: March 17, 1983
    Date of Patent: October 30, 1984
    Assignee: Celanese Corporation
    Inventor: James L. McGinnis
  • Patent number: 4448987
    Abstract: A process is disclosed for preparation of hydroxymethyl aryl monocarboxylic acid compounds by reduction of arylene dicarboxylic acid compounds in the presence of a rhenium catalyst and an aqueous solvent.
    Type: Grant
    Filed: November 30, 1982
    Date of Patent: May 15, 1984
    Assignee: Standard Oil Company (Indiana)
    Inventor: Lawrence D. Lillwitz
  • Patent number: 4440936
    Abstract: The chiral phosphine ligand (R)-1,2-bis(diphenylphosphino)-1-cyclohexylethane, when complexed to Rh(I), functions as a superior chiral hydrogenation catalyst. The chiral phosphine ligand is more stereochemically rigid than previous compounds; consequently, virtually optically pure materials can be produced from the chiral hydrogenation of prochiral compounds using the catalyst of this invention. This catalyst is especially useful in the chiral hydrogenation of alpha-acylamido acrylic acids.
    Type: Grant
    Filed: January 18, 1982
    Date of Patent: April 3, 1984
    Assignee: The Procter & Gamble Company
    Inventor: Dennis P. Riley
  • Patent number: 4431835
    Abstract: Alkyl carboxylates are hydrocarbonylated and/or carbonylated with carbon monoxide and hydrogen, in an aqueous medium, and in the presence of a catalytically effective amount of a catalyst system comprising (i) ruthenium, (ii) cobalt, (iii) at least one iodine-containing promoter, and (iv) chromium. The subject hydrocarbonylation/carbonylation is admirably well suited, e.g., for the preparation of acetaldehyde, ethanol, ethyl acetate and acetic acid, especially from a methyl carboxylate.
    Type: Grant
    Filed: July 6, 1981
    Date of Patent: February 14, 1984
    Assignee: Rhone-Poulenc Industries
    Inventors: Jean Gauthier-Lafaye, Robert Perron
  • Patent number: 4430506
    Abstract: Alkyl carboxylates are hydrocarbonylated and/or carbonylated with carbon monoxide and hydrogen, in an aqueous medium, and in the presence of a catalytically effective amount of a catalyst system comprising (i) ruthenium, (ii) cobalt, (iii) at least one iodine-containing promoter, and (iv) vanadium. The subject hydrocarbonylation/carbonylation is admirably well suited, e.g., for the preparation of acetaldehyde, ethanol, ethyl acetate and acetic acid, especially from a methyl carboxylate.
    Type: Grant
    Filed: July 6, 1981
    Date of Patent: February 7, 1984
    Assignee: Rhone-Poulenc Industries
    Inventors: Jean Gauthier-Lafaye, Robert Perron
  • Patent number: 4412958
    Abstract: 5-Phenyl-2S-pentanol is synthesized stereospecifically from S ethyl lactate. The method provides easily purified 5-phenyl-2S-pentanol useful in the synthesis of central nervous system active (CNS) agents such as levonantradol.
    Type: Grant
    Filed: August 5, 1982
    Date of Patent: November 1, 1983
    Assignee: Pfizer Inc.
    Inventors: Berkeley W. Cue, Jr., Bernard S. Moore
  • Patent number: 4405819
    Abstract: An improved process is provided for the production of alcohols from carboxylic acids using the reaction of carboxylic acids with alcohols in the presence of hydrogen and carbon monoxide to form esters which are subsequently hydrogenated over a suitable hydrogenation catalyst. The invention is useful because the temperature and pressure conditions are reduced from current commercial processes while hydrogenation catalyst activity and lifetime are promoted by the removal of catalyst poisons such as water.
    Type: Grant
    Filed: May 3, 1982
    Date of Patent: September 20, 1983
    Assignee: Conoco Inc.
    Inventor: Louis R. Duckwall, Jr.
  • Patent number: 4400566
    Abstract: Organic halides are reduced to a dechlorinated products with a catalyst mixture consisting essentially of a nickel compound, a triarylphosphine and a halide ion, in the presence of reducing means for maintaining nickel in the zero valent state.
    Type: Grant
    Filed: March 24, 1982
    Date of Patent: August 23, 1983
    Assignee: Union Carbide Corporation
    Inventor: Ismael Colon
  • Patent number: 4386219
    Abstract: Hydrogenation catalysts, which have a specific surface area of from 50 to 150 square meters per gram, solely or partially contain crystals having a spinel structure and copper in the form of copper oxide, and have been obtained by precipitating copper and aluminum in a ratio of from 0.25 to 3 atoms of copper per atom of aluminum from their compounds in the presence of a carbonate at a pH of from 4.5 to 9 and calcining the resulting precipitate at from 300.degree. to 800.degree. C., for the catalytic preparation of propanediols by hydrogenating hydroxypropionaldehydes at not more than 300 bar pressure and from 50.degree. to 200.degree. C., and processes for the preparation of propanediols by the use of such catalysts.The propanediols obtainable by the process of the invention, in particular 2,2-dimethylpropane-1,3-diol, are valuable starting materials for the preparation of lubricants, plastics, surface coatings and synthetic resins, for example corresponding polyesters.
    Type: Grant
    Filed: February 2, 1982
    Date of Patent: May 31, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Ernest Miesen, Franz J. Broecker, Wolfgang Schroeder, Karl Baer, Juergen Paetsch, Leopold Hupfer
  • Patent number: 4350825
    Abstract: A method to synthesize styrene from toluene by: (a) oxidizing toluene to form oxygenated toluene derivatives; (b) carbonylating said oxygenated products in the presence of a carbonylation catalyst and preferably a halogen promoter to produce phenylacetic acid; (c) hydrogenating said phenylacetic acid to synthesize phenylethyl alcohol; and (d) dehydrating said phenylethyl alcohol to obtain a high yield of styrene.
    Type: Grant
    Filed: May 30, 1980
    Date of Patent: September 21, 1982
    Assignee: Exxon Research & Engineering Co.
    Inventor: I-Der Huang
  • Patent number: 4346240
    Abstract: A novel class of heterogeneous catalysts, containing Group VIII transition metals in combination with alkali organic compounds is prepared, such as potassium naphthalene on ruthenium on carbon. The catalysts are useful as heterogeneous catalysts in the hydrogenation of carboxylic acid esters. A process for producing the materials is described. The catalysts permit the process of the hydrogenation of carboxylic acid esters to primary alcohols to be conducted with the ester in the liquid phase at a temperature not exceeding about 150.degree. C. with high selectivity. Catalysts of Group VIII transition metals and alkali metal on carbon are also useful in such processes.
    Type: Grant
    Filed: September 29, 1981
    Date of Patent: August 24, 1982
    Assignee: Allied Corporation
    Inventors: Roger A. Grey, Guido P. Pez
  • Patent number: 4322567
    Abstract: In a process for producing an aromatic alcohol by catalytic hydrogenation of at least one tertiary peroxide selected from the group consisting of tertiary aromatic hydroperoxides and tertiary aromatic peroxides in the presence of a palladium catalyst in a lower aliphatic alcohol solvent to form the corresponding alcohol; the improvement wherein said catalyst has a palladium metal surface area, determined by the CO chemisorption method, of up to about 200 m.sup.2 /g.multidot.Pd.
    Type: Grant
    Filed: May 22, 1980
    Date of Patent: March 30, 1982
    Assignee: Mitsui Petrochemical Industries Ltd.
    Inventors: Fujihisa Matsunaga, Norio Ohno, Hirohiko Nambu
  • Patent number: 4317918
    Abstract: An alcohol is produced in a high selectivity with a good yield from the corresponding carboxylic acid by reducing the latter with hydrogen in the presence of a rhenium catalyst in the coexistence of an organic base. An arylacetic acid, which is included in the starting carboxylic acid, can be produced in an excellent yield from the corresponding aryl aldehyde by reacting the latter with carbon monoxide and water in the presence of rhodium or its compound and hydrogen iodide.
    Type: Grant
    Filed: November 3, 1980
    Date of Patent: March 2, 1982
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Tetsuo Takano, Gohu Suzukamo, Masaru Ishino, Kiyoshi Ikimi
  • Patent number: 4313018
    Abstract: Anthranilic acid has been anchored to polystyrene, and rhodium, palladium, platinum and ruthenium complexes of this modified polystyrene have been prepared. These catalysts will reduce a variety of olefinic and aromatic hydrocarbons, and also nitrile, nitro and carbonyl functional groups, said carbonyl groups being present in either ketones or aldehydes.
    Type: Grant
    Filed: April 7, 1978
    Date of Patent: January 26, 1982
    Assignee: Western Kentucky University
    Inventors: Norman L. Holy, William A. Logan, Karl D. Stein
  • Patent number: 4307248
    Abstract: Supported coprecipitated catalysts comprised of one or more metals of Group VIII, one or more metals of Group IIA, and aluminum are used for hydrogenating hydrogenatable organic compounds. The catalysts are produced by preparing, under agitation; an aqueous mixture containing ions of Group VIII, Group IIA, and aluminum, as well as solid porous particles to form a coprecipitate of the metal ions and aluminum ions with the solid porous support particles; heating the aqueous reaction mixture; and adding precipitating agent to precipitate the metal ions and aluminum ions onto the solid support.
    Type: Grant
    Filed: November 28, 1980
    Date of Patent: December 22, 1981
    Assignee: Exxon Research & Engineering Co.
    Inventors: Allan E. Barnett, Albert P. Halluin
  • Patent number: 4298750
    Abstract: The novel borane-1,4-thioxane is synthesized by adding the calculated quantity of diborane to 1,4-thioxane. It is a stable liquid at 25.degree. C. The neat liquid is approximately 8.0 M in borane. The product, in spite of the additional oxygen atom in the ring, exhibits the desirable hydroborating and reducing action of borane-methyl sulfide. However, it possesses a major advantage over the latter in that the donor component, 1,4-thioxane, in contrast to methyl sulfide, is readily soluble in water and can be washed out of typical reaction mixtures. This greatly facilitates the synthetic applications of borane-1,4-thioxane over borane-methyl sulfide.
    Type: Grant
    Filed: February 19, 1980
    Date of Patent: November 3, 1981
    Assignee: Aldrich-Boranes, Inc.
    Inventor: Herbert C. Brown