Preparing By Reduction (e.g., By Hydrogenation, Etc.) Patents (Class 568/814)
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Patent number: 4990690Abstract: 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: GrantFiled: May 11, 1989Date of Patent: February 5, 1991Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Yuji Onda, Fumisada Kosuge, Masaru Tunoda
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Patent number: 4985572Abstract: 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: GrantFiled: November 21, 1988Date of Patent: January 15, 1991Assignees: The British Petroleum Company, p.l.c., BP Chemicals LimitedInventors: Melanie Kitson, Peter S. Williams
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Patent number: 4982016Abstract: 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: GrantFiled: June 6, 1989Date of Patent: January 1, 1991Assignee: Carter-Wallace, Inc.Inventor: Young M. Choi
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Patent number: 4973768Abstract: 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: GrantFiled: March 6, 1989Date of Patent: November 27, 1990Assignee: Rhone-Poulenc SanteInventors: Georges Cordier, Pierre Fouilloux, Jean-Michel Grosselin
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Patent number: 4968668Abstract: 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: GrantFiled: August 7, 1989Date of Patent: November 6, 1990Assignee: Consortium fur Elektrochemische Industrie GmbHInventors: Walter Hafner, Walter Gebauer, Marlies Regiert, Wilhelm Friedrich, Erich Markl
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Patent number: 4957986Abstract: 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: GrantFiled: December 15, 1989Date of Patent: September 18, 1990Assignee: E. I. Du Pont de Nemours and CompanyInventor: Harry N. Cripps
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Patent number: 4943667Abstract: 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: GrantFiled: January 13, 1989Date of Patent: July 24, 1990Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer
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Patent number: 4943652Abstract: 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: GrantFiled: November 14, 1988Date of Patent: July 24, 1990Assignee: Ajinomoto Co., Inc.Inventors: Masanobu Yatagai, Takashi Ohnuki
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Patent number: 4939307Abstract: 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: GrantFiled: February 23, 1989Date of Patent: July 3, 1990Assignee: Shell Oil CompanyInventors: Eit Drent, Willem W. Jager
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Patent number: 4929773Abstract: 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: GrantFiled: September 7, 1988Date of Patent: May 29, 1990Assignee: Hoechst Celanese CorporationInventor: Debra A. Ryan
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Patent number: 4918248Abstract: 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: GrantFiled: May 22, 1989Date of Patent: April 17, 1990Assignee: Kao CorporationInventors: Yasuyuki Hattori, Noriaki Fukuoka, Shigeru Tamura, Kunizo Hashiba, Kiyoshi Tsukada, Makoto Misono
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Patent number: 4912265Abstract: 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: GrantFiled: August 26, 1988Date of Patent: March 27, 1990Assignee: Akzo America Inc.Inventor: Ralph Franklin
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Patent number: 4886919Abstract: 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: GrantFiled: November 25, 1987Date of Patent: December 12, 1989Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventors: Ernesto Vera-Castaneda, John E. Logsdon
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Patent number: 4885409Abstract: 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: GrantFiled: May 4, 1988Date of Patent: December 5, 1989Assignee: Montedison S.p.A.Inventors: Andrea Gardano, Francesco Casagrande, Marco Foa, Guido Petrini, Riccardo Barisone, Lawrence Chapoy
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Patent number: 4880937Abstract: 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: GrantFiled: February 18, 1988Date of Patent: November 14, 1989Assignee: Japan Tobacco, Inc.Inventors: Hajime Matsushita, Makoto Shibagaki, Kyoko Takahashi
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Patent number: 4879389Abstract: 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: GrantFiled: June 25, 1987Date of Patent: November 7, 1989Inventor: Kazuo Achiwa
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Patent number: 4877909Abstract: 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: GrantFiled: February 22, 1988Date of Patent: October 31, 1989Assignee: Japan Tobacco, Inc.Inventors: Sigenobu Mizusaki, Hajime Matsushita, Shigeo Ishiguro, Hiroshi Ichinose, Akira Izumi
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Patent number: 4877908Abstract: 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: GrantFiled: October 13, 1987Date of Patent: October 31, 1989Assignee: NorsolorInventors: Michele Petit, Andre Mortreux, Francis Petit, Gerard Buono
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Patent number: 4868345Abstract: 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: GrantFiled: August 31, 1988Date of Patent: September 19, 1989Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4866181Abstract: A process for preparing optically active alcohols by reducing ketones using mono- or diisopinocampheylhaloboranes as reducing agents.Type: GrantFiled: December 17, 1987Date of Patent: September 12, 1989Assignee: Aldrich-Boranes, Inc.Inventor: Herbert C. Brown
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Patent number: 4783559Abstract: 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: GrantFiled: March 25, 1987Date of Patent: November 8, 1988Assignee: Japan Tobacco Inc.Inventors: Hajime Matsushita, Kyoko Takahashi, Makoto Shibagaki
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Patent number: 4731488Abstract: 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: GrantFiled: June 6, 1986Date of Patent: March 15, 1988Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.Inventors: Yuuji Shimasaki, Youichi Hino, Michio Ueshima
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Patent number: 4720597Abstract: 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: GrantFiled: October 24, 1986Date of Patent: January 19, 1988Assignee: Huels AktiengesellschaftInventors: Werner Otte, Rudolf Nehring
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Patent number: 4650898Abstract: 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: GrantFiled: December 14, 1984Date of Patent: March 17, 1987Assignee: International Flavors & Fragrances Inc.Inventor: John B. Hall
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Patent number: 4628130Abstract: 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: GrantFiled: August 8, 1985Date of Patent: December 9, 1986Assignee: Institut Francais du PetroleInventors: Jean-Paul Bournonville, Jean-Pierre Candy, Gil Mabilon
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Patent number: 4625049Abstract: 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: GrantFiled: June 30, 1982Date of Patent: November 25, 1986Assignee: Chevron Research CompanyInventor: Steven P. Current
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Patent number: 4598058Abstract: 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: GrantFiled: January 31, 1985Date of Patent: July 1, 1986Assignee: BASF AktiengesellschaftInventors: Gerhard Frank, Gerald Neubauer, Paul Duffner, Hans J. Wilfinger
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Patent number: 4548810Abstract: 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: GrantFiled: May 8, 1981Date of Patent: October 22, 1985Inventor: Albert Zofchak
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Patent number: 4546208Abstract: 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: GrantFiled: March 14, 1984Date of Patent: October 8, 1985Assignee: International Flavors & Fragrances Inc.Inventors: Wilhelmus J. Wiegers, Mark A. Sprecker
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Patent number: 4511743Abstract: 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: GrantFiled: November 4, 1983Date of Patent: April 16, 1985Assignee: Institut Francais du PetroleInventors: Claude Seite, Dominique Commereuc, Yves Chauvin
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Patent number: 4507510Abstract: 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: GrantFiled: December 28, 1983Date of Patent: March 26, 1985Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Shigeo Yoshinaka, Tsukasa Toki, Tomoji Tsuji, Seiji Uchiyama
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Patent number: 4493801Abstract: 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: GrantFiled: November 2, 1981Date of Patent: January 15, 1985Assignee: BASF AktiengesellschaftInventors: Franz Merger, Gerhard Nestler
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Patent number: 4486607Abstract: 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: GrantFiled: July 12, 1982Date of Patent: December 4, 1984Assignee: Bush Boake Allen LimitedInventor: David Webb
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Patent number: 4482760Abstract: 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: GrantFiled: November 16, 1983Date of Patent: November 13, 1984Assignee: Degussa AktiengesellschaftInventors: Axel Kleemann, Klaus Deller, Karlheinz Drauz, Bernd Lehmann
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Patent number: 4480115Abstract: 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: GrantFiled: March 17, 1983Date of Patent: October 30, 1984Assignee: Celanese CorporationInventor: James L. McGinnis
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Catalyzed hydrogenation of terephthalic acid to p-hydroxymethylbenzoic acid using a rhenium catalyst
Patent number: 4448987Abstract: 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: GrantFiled: November 30, 1982Date of Patent: May 15, 1984Assignee: Standard Oil Company (Indiana)Inventor: Lawrence D. Lillwitz -
Patent number: 4440936Abstract: 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: GrantFiled: January 18, 1982Date of Patent: April 3, 1984Assignee: The Procter & Gamble CompanyInventor: Dennis P. Riley
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Patent number: 4431835Abstract: 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: GrantFiled: July 6, 1981Date of Patent: February 14, 1984Assignee: Rhone-Poulenc IndustriesInventors: Jean Gauthier-Lafaye, Robert Perron
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Patent number: 4430506Abstract: 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: GrantFiled: July 6, 1981Date of Patent: February 7, 1984Assignee: Rhone-Poulenc IndustriesInventors: Jean Gauthier-Lafaye, Robert Perron
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Patent number: 4412958Abstract: 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: GrantFiled: August 5, 1982Date of Patent: November 1, 1983Assignee: Pfizer Inc.Inventors: Berkeley W. Cue, Jr., Bernard S. Moore
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Patent number: 4405819Abstract: 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: GrantFiled: May 3, 1982Date of Patent: September 20, 1983Assignee: Conoco Inc.Inventor: Louis R. Duckwall, Jr.
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Patent number: 4400566Abstract: 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: GrantFiled: March 24, 1982Date of Patent: August 23, 1983Assignee: Union Carbide CorporationInventor: Ismael Colon
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Patent number: 4386219Abstract: 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: GrantFiled: February 2, 1982Date of Patent: May 31, 1983Assignee: BASF AktiengesellschaftInventors: Franz Merger, Ernest Miesen, Franz J. Broecker, Wolfgang Schroeder, Karl Baer, Juergen Paetsch, Leopold Hupfer
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Patent number: 4350825Abstract: 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: GrantFiled: May 30, 1980Date of Patent: September 21, 1982Assignee: Exxon Research & Engineering Co.Inventor: I-Der Huang
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Patent number: 4346240Abstract: 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: GrantFiled: September 29, 1981Date of Patent: August 24, 1982Assignee: Allied CorporationInventors: Roger A. Grey, Guido P. Pez
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Patent number: 4322567Abstract: 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: GrantFiled: May 22, 1980Date of Patent: March 30, 1982Assignee: Mitsui Petrochemical Industries Ltd.Inventors: Fujihisa Matsunaga, Norio Ohno, Hirohiko Nambu
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Patent number: 4317918Abstract: 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: GrantFiled: November 3, 1980Date of Patent: March 2, 1982Assignee: Sumitomo Chemical Co., Ltd.Inventors: Tetsuo Takano, Gohu Suzukamo, Masaru Ishino, Kiyoshi Ikimi
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Patent number: 4313018Abstract: 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: GrantFiled: April 7, 1978Date of Patent: January 26, 1982Assignee: Western Kentucky UniversityInventors: Norman L. Holy, William A. Logan, Karl D. Stein
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Patent number: 4307248Abstract: 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: GrantFiled: November 28, 1980Date of Patent: December 22, 1981Assignee: Exxon Research & Engineering Co.Inventors: Allan E. Barnett, Albert P. Halluin
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Patent number: 4298750Abstract: 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: GrantFiled: February 19, 1980Date of Patent: November 3, 1981Assignee: Aldrich-Boranes, Inc.Inventor: Herbert C. Brown