Of Compound Containing A -coo- Group Patents (Class 568/864)
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Patent number: 5536888Abstract: A diol compound, for example, hexanediol, is produced with a high efficiency by esterifying a carboxylic acid mixture, collected from a reaction product mixture of a liquid phase oxidation of cyclohexane, with an esterifying agent and hydrogenate-decomposing the resultant esterification product mixture with hydrogen.Type: GrantFiled: December 27, 1994Date of Patent: July 16, 1996Assignee: UBE Industries, Ltd.Inventors: Yasushi Shiomi, Hiroyuki Fukushima, Toshihiko Sumida, Shinichi Furusaki
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Patent number: 5536854Abstract: 2-Methyl-1,4-butanediol and 3-methyltetrahydrofuran are prepared by reacting a compound of the general formula I or II ##STR1## where R.sup.1 and R.sup.2 are each hydrogen or C.sub.1 -C.sub.8 -alkyl and the formyl group of II may also be present as acetal with a C.sub.1 -C.sub.8 -alkanol, is reacted with hydrogen in the presence of copper or of a metal of groups 7 to 10 of the Periodical Table of elements or of a compound of these metals.Type: GrantFiled: January 26, 1995Date of Patent: July 16, 1996Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Weyer, Rolf Fischer, Franz Merger, Juergen Frank, Jochem Henkelmann, Hardo Siegel, Thomas Ruehl
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Patent number: 5508394Abstract: Esters of citric acid or acetylcitric anhydride with compounds of at least 3 OH groups selected from the group consisting of polyglycerol, sugarcarboxylic acids, alkyl glucosides, derivatives of oligosaccharides, aminosorbitol, aminodisorbitol, glucosamine, triethanolamine and trishydroxyethylmelamine, each OH group of the alcohol component of the esters being esterified on average with from 0.15 to 1 molecule of citric acid or acetylcitric anhydride, are useful as additives in low-phosphate or phosphate-free detergents.Type: GrantFiled: September 16, 1993Date of Patent: April 16, 1996Assignee: BASF AktiengesellschaftInventors: Elisabeth Kappes, Alfred Oftring, Richard Baur, Alexander Kud, Dieter Boeckh, Heinrich Hartmann, Volker Schwendemann
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Patent number: 5481048Abstract: A copper-containing hydrogenation reaction catalyst is prepared by reducing a precursor of a copper-containing catalyst usable in hydrogenation reaction with hydrogen gas or a mixture of hydrogen and an inert gas by liquid phase reduction in a stream of a solvent in the temperature range of from 50.degree. to 140.degree. C. An alcohol is produced using the catalyst thus obtained in a fixed bed continuous reaction system.Type: GrantFiled: December 13, 1994Date of Patent: January 2, 1996Assignee: Kao CorporationInventors: Kiyoshi Tsukada, Yasuyuki Hattori, Taku Mimura
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Patent number: 5478789Abstract: A hydrogenation reaction catalyst precursor of the present invention comprises a catalyst carrier (A) and a metal oxide composition (B) carried on or mixed with the catalyst carrier (A) at a weight ratio of (B)/(A)=15/85 to 65/35; the catalyst carrier (A) comprising a carrier base material of silica, etc. and a coating of titanium oxide and/or titanium hydroxide, the metal oxide composition (B) comprising copper oxide, zinc oxide, and at least one oxide of a metal selected from the group consisting of an element of group IIa of the periodic table, an element of group IIIb of the table, a lanthanide element, and an actinide element at a weight ratio of 100/(0 to 25)/(0 to 25). A hydrogenation reaction catalyst with a high catalytic activity and a high reaction selectivity is obtained by reduction of the hydrogenation reaction catalyst precursor.Type: GrantFiled: October 4, 1994Date of Patent: December 26, 1995Assignee: Kao CorporationInventors: Yasuyuki Hattori, Kiyoshi Tsukada
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Patent number: 5475160Abstract: This invention relates to a process for the direct hydrogenation of triglycerides which comprises contacting and reacting one or more triglyceride with hydrogen under liquid phase hydrogenation conditions in the presence of a catalyst comprising a copper compound, a zinc compound, at least one rare earth compound, and, optionally, a compound selected from the group consisting of aluminum, zirconium, magnesium, and mixtures thereof.Type: GrantFiled: November 7, 1994Date of Patent: December 12, 1995Assignee: Shell Oil CompanyInventors: David M. Singleton, Brendan D. Murray
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Patent number: 5475159Abstract: This invention relates to a process for the direct hydrogenation of methyl esters which comprises contacting and reacting one or more detergent range methyl esters with hydrogen under predominantly liquid phase hydrogenation conditions in the presence of a catalyst comprising a copper compound, a zinc compound, and at least one compound selected from the group consisting of aluminum, zirconium, magnesium, a rare earth and mixtures thereof.Type: GrantFiled: November 7, 1994Date of Patent: December 12, 1995Assignee: Shell Oil CompanyInventors: David M. Singleton, Brendan D. Murray
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Patent number: 5463143Abstract: This invention relates to a process for the direct hydrogenation of wax esters which comprises contacting and reacting a wax ester with hydrogen under liquid phase hydrogenation conditions in the presence of a catalyst comprising a copper compound, a zinc compound, and at least one rare earth compound.Type: GrantFiled: November 7, 1994Date of Patent: October 31, 1995Assignee: Shell Oil CompanyInventors: David M. Singleton, Brendan D. Murray
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Patent number: 5426246Abstract: Disclosed are a catalyst for directly reducing a carboxylic acid, the catalyst comprising a tin compound and a ruthenium compound supported on a carrier, the catalyst being prepared by the steps of calcining the tin compound in the presence of oxygen after deposition of the tin compound alone on the carrier, and activating the obtained product after deposition of the ruthenium compound on said carrier, a process for preparing the catalyst, and a process for preparing an alcohol compound using the catalyst.Type: GrantFiled: July 26, 1994Date of Patent: June 20, 1995Assignee: Arakawa Chemical Industries, Ltd.Inventors: Eiji Nagahara, Yasushi Itoi
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Patent number: 5414159Abstract: A process is described for the production of cyclohexanedimethanol by hydrogenation of a dialkyl cyclohexanedicarboxylate which comprises the steps of:(a) providing a hydrogenation zone containing a charge of a granular reduced manganese promoted copper catalyst;(b) forming a vaporous feed stream of a hydrogenatable material comprising a dialkyl cyclohexanedicarboxylate and from about 0.1 wt % up to about 15 wt % of an acidic material at a feed temperature which is in the range of from about 150.degree. C. to about 350.degree. C. and which is above the dew point of the feed stream and at a feed pressure which is in the range of from about 150 psia (about 10.34 bar) up to about 2000 psia (about 137.Type: GrantFiled: December 30, 1993Date of Patent: May 9, 1995Assignee: Eastman Chemical CompanyInventors: Paul Appleton, Michael A. Wood
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Patent number: 5406004Abstract: A process is described for the production of a hydroxylic compound selected from alcohols and diols by hydrogenation of a corresponding hydrogenatable material selected from monoesters of carboxylic acids, monoesters of dicarboxylic acids, diesters of dicarboxylic acids, lactones, and mixtures of two or more thereof which comprises:(a) providing a hydrogenation zone containing a charge of a granular heterogeneous ester hydrogenation catalyst;(b) supplying to the hydrogenation zone a vaporous feed stream containing hydrogen and a hydrogenatable material selected from monoesters of carboxylic acids, monoesters of dicarboxylic acids, diesters of dicarboxylic acids, lactones, and mixtures of two or more thereof, at an inlet temperature which is above the dew point of the mixture;(c) maintaining the hydrogenation zone under temperature and pressure conditions which are conducive to effecting hydrogenation of esters;(d) recovering from the hydrogenation zone a two phase product stream containing a hydroxylic compouType: GrantFiled: December 30, 1993Date of Patent: April 11, 1995Assignee: Eastman Chemical CompanyInventors: Philip H. D. Eastland, John Scarlett, Michael W. M. Tuck, Michael A. Wood
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Patent number: 5403962Abstract: The invention describes a chromium-free catalyst for hydrogenation of organic compounds, especially organic compounds containing the carbonyl function, such as aldehydes, ketones, or carboxylic acids or their esters, to the corresponding alcohols wherein the catalysts is characterized by the following features:its oxide form corresponds to the compositionCu.sub.a Al.sub.b Zr.sub.c Mn.sub.d O.sub.xwherein the following relations apply:for the first embodiment:a>O; b>O; c.gtoreq.O; d>O; a>b/2; b>a/4; a>c; a>d;and for the second embodiment:a>O; b=a/40 to a/4; c.gtoreq.O; d>O; a>c; a=0.5 d to 0.95 dand x is the number of oxygen ions needed per formula unit for electrical neutrality.Type: GrantFiled: May 31, 1994Date of Patent: April 4, 1995Assignee: Sud-Chemie AGInventors: Michael Schneider, Karl Kochloefl, Gerd Maletz
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Patent number: 5399792Abstract: Unsaturated fatty alcohols with 6 to 22 C atoms can be produced by directly hydrating deacidified and/or non-deacidified glyceride oils containing monounsaturated and/or polyunsaturated, straight chain and/or branched-chain fatty acids having 6 to 22 C atoms in the fatty acid residue, by applying a 30 to 100-fold excess of hydrogen in a pressure range from 50 to 300 bars, at temperatures from 200.degree. to 400.degree. C., to zinc-chrome-catalysts of the spinel type, while largely preserving the olefinic double bonds and with formation of propane and 1,2-propylene glycol.Type: GrantFiled: May 6, 1994Date of Patent: March 21, 1995Assignee: Henkel Kommanditgesellschaft auf AktienInventor: Guenther Demmering
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Patent number: 5395987Abstract: A continuous process is described for the production of 1,4-cyclohexanedimethanol (CHDM) having a desired or predetermined trans-:cis- isomer ratio by catalytic hydrogenation of a dialkyl 1,4-cyclohexanedicarboxylate in the presence of an ester hydrogenation catalyst. The process is capable of being operated for an extended period of time during which the hydrogenation catalyst declines in catalytic activity and comprises feeding a vaporous mixture of the dialkyl 1,4-cyclohexanedicarboxylate and hydrogen to a hydrogenation zone containing the hydrogenation catalyst and recovering CHDM product. The degree of conversion of the dialkyl 1,4-cyclohexanedicarboxylate at a particular combination of temperature and pressure is related to the trans-:cis- isomer ratio of the CHDM product and may be varied by adjusting at least one feed condition selected from (i) the dialkyl 1,4-cyclohexanedicarboxylate feed rate and (ii) the hydrogen-containing gas:dialkyl 1,4-cyclohexanedicarboxylate molar ratio.Type: GrantFiled: December 30, 1993Date of Patent: March 7, 1995Assignee: Eastman Chemical CompanyInventors: Colin Rathmell, Richard C. Spratt, Michael W. M. Tuck
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Patent number: 5395990Abstract: A process is described for the production of a hydroxylic compound selected from alcohols and diols by hydrogenation of a hydrogenatable material selected from monoesters of carboxylic acids, monoesters of dicarboxylic acids, diesters of dicarboxylic acids, aldehydes, olefinically unsaturated aldehydes, and mixtures of two or more thereof, which process comprises the steps of:(a) providing a hydrogenation zone containing a charge of a granular hydrogenation catalyst which has a total surface area of at least about 15 m.sup.Type: GrantFiled: December 30, 1993Date of Patent: March 7, 1995Assignee: Eastman Chemical CompanyInventor: John Scarlett
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Patent number: 5395991Abstract: A hydrogenation process is described for the production of a hydroxylic compound selected from alcohols and diols by hydrogenation of a corresponding unsaturated organic compound selected from esters, diesters and lactones which involves use of two hydrogenation zones (11, 36), each containing a charge of a hydrogenation catalyst (12, 37). In a first phase of operation one of the hydrogenation zones (36 or 11) is in standby condition and a stream of hot hydrogen-containing gas is passed therethrough. Meanwhile a vaporous feed stream comprising a hydrogen-containing gas and the unsaturated organic compound to be hydrogenated, e.g. dimethyl 1,4-cyclohexanedicarboxylate, is fed to the active zone (11 or 36). This feed stream can include the gas stream from the first mentioned hydrogenation zone (36 or 11).Type: GrantFiled: December 30, 1993Date of Patent: March 7, 1995Assignee: Eastman Chemical CompanyInventors: John Scarlett, Michael W. M. Tuck, Michael A. Wood
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Patent number: 5391771Abstract: A process for the preparation of propane-1,2,3-tricarboxylic acid, tetrahydrofurfurylacetic acid and the C.sub.1 - to C.sub.20 -alkyl or C.sub.7 - to C.sub.12 -aralkyl esters thereof, propane-1,2,3-trimethanol, 3-methyltetrahydrofuran, 3-(2'-hydroxyethyl)tetrahydrofuran, 4-hydroxymethyltetrahydropyran, 2-methyl-.gamma.-butyrolactone and/or 3-methyl-.gamma.-butyrolactone, comprises reacting citric acid or the C.sub.1 - to C.sub.20 -alkyl or C.sub.7 - to C.sub.12 -aralkyl esters thereof on hydrogenation catalysts in non-aqueous solvents at from 50.degree. to 400.degree. C. and at from 1 to 400 bar.Type: GrantFiled: September 30, 1993Date of Patent: February 21, 1995Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Weyer, Rolf Fischer, Christoph Sigwart
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Patent number: 5387753Abstract: A process is described for reactivating an at least partially deactivated copper-containing ester hydrogenation catalyst which has undergone deactivation through use in hydrogenation of an unsaturated organic compound selected from esters of C.sub.8 to C.sub.22 monocarboxylic acids, diesters of dicarboxylic acids, and lactones, to yield a corresponding hydroxylic compound selected from alcohols and diols which comprises contacting the at least partially deactivated copper-containing catalyst at an effective reactivation temperature and for an effective period of time with a stream of hydrogen-containing gas which is substantially free from the unsaturated organic compound thereby to reactivate the at least partially deactivated copper-containing catalyst.Type: GrantFiled: December 30, 1993Date of Patent: February 7, 1995Assignee: Eastman Chemical CompanyInventors: John Scarlett, Michael W. M. Tuck, Michael A. Wood
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Patent number: 5364986Abstract: C.sub.8-22 fatty alcohols are produced by a process which comprises contacting a triglyceride with hydrogen in the presence of a copper-zinc catalyst and in a reaction zone. The hydrogen pressure in the reaction zone is from about 200 to about 280 bar, the temperature of the entrance of the reaction zone is from about 200.degree. C. to about 230.degree. C., and the temperature of the exit of the reaction zone is from about 190.degree. C. to about 220.degree. C. The amount of 1,2-propanediol formed is optimized by the lower temperature of the exit portion of the reaction zone.Type: GrantFiled: November 10, 1993Date of Patent: November 15, 1994Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Guenther Demmering, Stephan Heck, Lothar Friesenhagen
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Patent number: 5345005Abstract: In one embodiment, the invention relates to a catalyst in powdered form which comprises a major amount of the oxides of copper and zinc, and a minor amount of aluminum oxide wherein the pore volume of pores of said catalysts having a diameter between about 120 and about 1000 .ANG. is at least about 40% of the total pore volume. In another embodiment, the invention relates to a process for preparing hydrogenation catalysts comprising the oxides of copper, zinc and aluminum which comprises the steps of(A) preparing a first aqueous solution containing at least one water-soluble copper salt and at least one water-soluble zinc salt;(B) preparing a second solution containing at least one water-soluble basic aluminum salt and at least one alkaline precipitating agent;(C) mixing the first and second solutions whereby an insoluble solid is formed;(D) recovering the insoluble solid.Type: GrantFiled: September 18, 1992Date of Patent: September 6, 1994Assignee: Engelhard CorporationInventors: Deepak S. Thakur, Brian L. Roberts, Thomas J. Sullivan, Anita L. Vichek
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Patent number: 5342488Abstract: A process for the separation of 1,4-butanediol from mixtures obtained by the catalytic hydrogenation of maleates, fumarates, and/or succinates, which also contain tetrahydrofuran, water, C.sub.1 -C.sub.4 alcohols, succinic diesters, hydroxybutyrates, alkylhydroxyalkyl succinates, gamma-butyrolactone and butyrates, in addition to 1,4-butanediol, comprising the following steps:a) separating, in a first column having an actual number of plates of from 20 to 70 and operated at a top pressure of from 50 to 1100 mbar and preferably from 50 to 500 mbar and a top temperature of from 40.degree. to 120.degree. C., alcohol, water and tetrahydrofuran, as overhead product,b) feeding the bottom product of the first column into a second column having an actual number of plates of from 30 to 90 and withdrawing the overhead product consisting of alcohol and butyrate and obtained at a top pressure of from 45 to 250 mbar and a top temperature of from 45.degree. to 120.degree. C.Type: GrantFiled: February 17, 1993Date of Patent: August 30, 1994Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Gosch, Harald Rust, Rolf Fischer, Claus Hechler, Rolf Pinkos
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Patent number: 5334779Abstract: Disclosed are catalyst compositions comprised of the oxides of copper, zinc, and a third element selected from the group consisting of aluminum, magnesium, zirconium, and mixtures thereof, and the use of such catalyst compositions in the hydrogenation of carbonyl compounds such as carboxylate esters to obtain the alcohol corresponding to the acid residue of the ester.Type: GrantFiled: June 1, 1993Date of Patent: August 2, 1994Assignee: Eastman Kodak CompanyInventor: Yeong-Jen Kuo
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Patent number: 5326889Abstract: There is disclosed a process for the production of 1,4-butanediol and tetrahydrofuran by the catalytic hydrogenation in the gas phase of .gamma.-butyrolactone using a solid catalyst comprising copper and silicon, copper, chromium, and manganese or copper, chromium, manganese and barium.Type: GrantFiled: November 4, 1992Date of Patent: July 5, 1994Assignee: Tonen CorporationInventors: Sadakatsu Suzuki, Tatsumi Ichiki, Hiroshi Ueno
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Patent number: 5250713Abstract: A process for producing desulfurized fats and oils or fatty acid esters is disclosed, which comprises treating fats and oils or fatty acid esters under hydrogen or a mixture of hydrogen and an inert gas atmosphere at a pressure of from 0.1 to 500 kg/cm.sup.2 in the absolute pressure at a temperature of from 100.degree. to 350.degree. C. in the presence of a catalyst of the following formula (I):Cu.multidot.X.sub.x .multidot.Y.sub.y .multidot.O.sub.z (I)wherein all symbols are defined in the disclosure. A process for producing an alcohols using desulfurized fats and oils or fatty acid esters is also disclosed. According to the process for producing an alcohol of the present invention, an alcohol of a high purity and good qualities can efficiently and effectively be produced.Type: GrantFiled: March 11, 1992Date of Patent: October 5, 1993Assignee: Kao CorporationInventors: Hiroyuki Tamura, Yasuyuki Hattori, Kunizo Hashiba, Osamu Tabata, Kiyoshi Tsukada, Noriaki Fukuoka
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Patent number: 5243095Abstract: In one embodiment, the invention relates to a catalyst in powdered form comprising the oxides of copper, iron, aluminum and manganese wherein the atomic ratio of copper to iron is at least 1:1. In another embodiment, the invention relates to a process for preparing such hydrogenation catalysts which comprises the steps of(A) preparing a first aqueous solution containing at least one water-soluble copper salt, at least one water-soluble iron salt, and at least one water-soluble manganese salt;(B) preparing a second solution containing at least one water-soluble basic aluminum salt and at least one alkaline precipitating agent;(C) mixing the first and second solutions wherein an insoluble solid is formed;(D) recovering the soluble solid; and(E) calcining the recovered solid to form the desired catalyst.The invention also relates to a process for hydrogenating aldehydes, ketones, carboxylic acids and carboxylic acid esters.Type: GrantFiled: April 24, 1992Date of Patent: September 7, 1993Assignee: Engelhard CorporationInventors: Brian D. Roberts, Deepak S. Thakur, Thomas J. Sullivan, Robert A. Plundo
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Patent number: 5233099Abstract: A process for producing an alcohol by continuously passing a fatty acid ester, a fatty acid triglyceride or a fatty acid through a hydrogenation catalyst to thereby produce the aimed alcohol through catalytic reduction is disclosed, wherein the employed reactor is a fixed bed reactor in which the liquid phase and the gas phase are continuously passed together in descending parallel flows through the hydrogenation catalyst fixed in the reactor; and at least one cooling mean for cooling the reaction system is provided at a position in the vertical direction of the reactor. According to the process of the present invention with the use of a fixed bed reactor, an alcohol, which has extremely high qualities and a high purity and is contaminated with little hydrocarbon and aldehyde by-products, can be produced. The process of the present invention further makes it possible to omit the post-treatment for eliminating the by-products.Type: GrantFiled: December 24, 1991Date of Patent: August 3, 1993Assignee: Kao CorporationInventors: Osamu Tabata, Kunizo Hashiba, Takahiro Kawakami
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Patent number: 5233100Abstract: A process for producing an alcohol from a fatty acid ester, a fatty acid triglyceride or a fatty acid by continuously catalytically reducing the starting material in the presence of a hydrogenation catalyst is disclosed. In the process of the present invention, two reactors (i.e., the main reactor located upstream and the after reactor located downstream) being located in series are employed. In the process of the present invention, two reactors are employed and the temperatures thereof are individually controlled, whereby the conversion ratio is elevated while suppressing the formation of hydrocarbon and aldehyde by-products. Thus, an alcohol of extremely high quality and high purity can be produced. Further, the process of the present invention makes it possible to omit any post-treatment for eliminating the by-products. Furthermore, the active life of the hydrogenation catalyst can be remarkably prolonged by using three reactors (i.e., the guard reactor, the main reactor and the after reactor).Type: GrantFiled: December 27, 1991Date of Patent: August 3, 1993Assignee: Kao CorporationInventors: Osamu Tabata, Atsuhito Mori, Takahiro Kawakami, Kunizo Hashiba, Kiyoshi Tsukada
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Patent number: 5220020Abstract: A process is provided whereby organic carbonyl substrates, including esters, lactones, ketones, amides and imides are reduced in a reaction with a silane reducing reagent and a catalyst. Exemplary catalysts include metal alkoxides and metal aryloxides.Type: GrantFiled: November 14, 1991Date of Patent: June 15, 1993Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Alberto Gutierrez, Scott C. Berk, Kristina A. Kreutzer
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Patent number: 5210337Abstract: Rhenium has been found to be formaldehyde resistant catalyst and is thus useful in the catalytic hydrogenation of carbonyls, acetals and esters to alcohols when the reaction medium contains formaldehyde as a reactant or impurity. Also, rhenium is a useful catalyst in the hydrogenolysis of acylic acetals to alcohols.Type: GrantFiled: March 28, 1990Date of Patent: May 11, 1993Assignee: Hoechst Celanese CorporationInventor: Jerry A. Broussard
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Patent number: 5196602Abstract: Maleic anhydride is hydrogenated to produce 1,4-butanediol in a two-stage process. In the first stage maleic anhydride and/or maleic acid contacted with hydrogen at a temperature of about 100.degree. C. to about 350.degree. C. in the presence of a suitable hydrogenation catalyst to produce succinic anhydride and/or gamma-butyrolactone. In the second stage, the succinic anhydride and/or gamma-butyrolactone and hydrogen are contacted at a temperature of about 180.degree. C. to about 350.degree. C. in the presence of a ruthenium-containing hydrogenation catalyst to produce 1,4-butanediol.Type: GrantFiled: December 30, 1991Date of Patent: March 23, 1993Assignee: The Standard Oil CompanyInventors: John R. Budge, Thomas G. Attig, Anne M. Graham
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Patent number: 5196601Abstract: Disclosed herein is a process for producing an alcohol or an amine by reducing a compound having a formyl, keto, nitro, oxirane, ester, nitrile, amide or halogenated carboxyl group with an alkali metal boro-hydride in the presence of a compound having a hydroxyl group and ether linkage. According to the present invention, a functional group having a great steric hindrance can be reduced, and a corresponding alcohol or amine can efficiently be produced under very mild conditions on an industrial scale.Type: GrantFiled: June 17, 1992Date of Patent: March 23, 1993Assignee: Kao CorporationInventors: Tomohito Kitsuki, Yoshiaki Fujikura
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Patent number: 5191091Abstract: A process for hydrogenating bound oxygen-containing organic feeds into their corresponding alcohols by contact with a coprecipitated copper-aluminum catalyst that has been activated by contact with reducing gas at a temperature that gradually increases.Type: GrantFiled: January 27, 1992Date of Patent: March 2, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Richard W. Wegman, David R. Bryant
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Patent number: 5185476Abstract: Disclosed are novel catalysts useful for the hydrogenation of carbonyl-containing compounds at mild conditions of temperature and pressure to produce alcohols or amines is disclosed. The catalysts comprise palladium and zinc on a catalyst support material and are obtained by the steps of:(a) providing a catalyst support material on which is deposited zero-valent palladium in a uniformly and highly dispersed form;(b) contacting the palladium-bearing support material of (a) with zinc or a reducible compound thereof; and, preferably,(c) heating the palladium- and zinc-bearing support of (b) at a temperature of about 200.degree. to 400.degree. C. in the presence of an oxygen-containing gas.Type: GrantFiled: September 26, 1991Date of Patent: February 9, 1993Assignee: Eastman Kodak CompanyInventor: Bruce L. Gustafson
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Patent number: 5180858Abstract: The invention relates to a process for the catalytic hydrogenation of liquid saturated and unsaturated C.sub.6-24 fatty acid methyl esters for the production of saturated fatty alcohols and methanol in the presence of gaseous hydrogen and hydrogenation catalysts under pressures of 50 to 300 bar and at temperatures in the range from 160.degree. to 250.degree. C., characterized in that the hydrogenation reaction is carried out in a tube bundle reactor in which isothermal conditions are established by a cooling or heating fluid, the liquid phase and gas phase being passed together as a co-current trickle phase over catalyst packings in the individual tubes of the reactor without any back-mixing, and in that the load per unit volume of the reaction is between 0.2 and 2.5 liters starting material per liter reactor volume per hour and the load per unit area of each individual tube of the reactor is between 1.5 and 24 m.sup.3 starting material per m.sub.Type: GrantFiled: October 24, 1991Date of Patent: January 19, 1993Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Theo Fleckenstein, Gerd Goebel, Franz-Josef Carduck, Guenther Demmering, Hans-Peter Kubersky
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Patent number: 5142067Abstract: A process for hydrogenating feeds into their corresponding alcohols by contact with a coprecipitated catalyst comprising copper, aluminum, and a metal (X) selected from the group consisting of magnesium, zinc, titanium, zirconium, tin, nickel, cobalt and mixtures thereof; that has been reduced with an increasing temperature during the reduction.Type: GrantFiled: November 5, 1991Date of Patent: August 25, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Richard W. Wegman, David R. Bryant
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Patent number: 5118883Abstract: A process is described for the preparation of propylene glycol and ethylene glycol from formaldehyde, the first step involving conversion of the formaldehyde into a mixture of polyhydroxyl compounds in a conventional manner in an alkaline medium by self-condensation and the second step involving catalytic hydrogenolysis of this mixture with a hydrogen consumption of at least 0.5 mol of hydrogen per mol of formaldehyde employed for forming the polyhydroxyl compounds.Type: GrantFiled: July 10, 1991Date of Patent: June 2, 1992Assignee: BASF AktiengesellschaftInventors: Eugen Gehrer, Wolfgang Harder
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Patent number: 5099038Abstract: There is disclosed a process for the production of 1,4-butanediol and tetrahydrofuran by the catalytic hydrogenation in the gas phase of .gamma.-butyrolactone using a solid catalyst comprising copper and silicon, copper, chromium, and manganese or copper, chromium, manganese and barium.Type: GrantFiled: November 21, 1990Date of Patent: March 24, 1992Assignee: Tonen CorporationInventors: Sadakatsu Suzuki, Tatsumi Ichiki, Hiroshi Ueno
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Patent number: 5091559Abstract: A process is disclosed for forming alkyl 4-oxobutyrates and its acetals which comprises reacting under anhydrous conditions acrolein or its acetals with carbon monoxide and an alcohol of the formula R OH wherein R is lower alkyl in the presence of a catalytically effective amount of a catalyst comprising palladium metal which is either unsupported or supported on an inert carrier and a promoting effective amount of hydrogen halide. An intermediate in the process, i.e., .beta.-halopropionaldehyde or acetal thereof can also be used in forming alkyl 4-oxobutyrates and acetals thereof by reacting under anhydrous conditions said .beta.-halopropionaldehyde or its acetals with carbon monoxide and an alcohol of the formula ROH wherein R is lower alkyl in the presence of a catalytically effective amount of a catalyst comprising palladium metal which is either unsupported or supported on an inert carrier.Type: GrantFiled: February 8, 1988Date of Patent: February 25, 1992Assignee: Quantum Chemical CorporationInventors: Jawad H. Murib, William D. Baugh
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Patent number: 5077442Abstract: A method for producing 1,4-butanediol by hydrogenating succinic anhydride, succinic acid or .gamma.-butyrolactone in the presence of a catalyst, wherein the hydrogenation reaction is conducted in a liquid phase using as the catalyst a ruthenium type catalyst comprising ruthenium, an organic phosphine and a phosphorus compound of the following formula (1): ##STR1## wherein each of X and Y is an atom or a group selected from the group consisting of a hydrogen atom, a hydroxyl group, a halogen atom, an alkoxy group, an alkyl group and an aryl group.Type: GrantFiled: April 11, 1991Date of Patent: December 31, 1991Assignee: Mitsubishi Kasei CorporationInventors: Yoshinori Hara, Hiroko Inagaki
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Patent number: 5076896Abstract: A process for the separation of propylene glycol from a mixture of low-boiling fatty alcohols and propylene glycol which comprises extracting the mixture with water to produce a water-propylene glycol mixture and fractionating the water-propylene glycol mixture to produce propylene glycol that is substantially anhydrous and an apparatus for carrying out the process.Type: GrantFiled: June 13, 1989Date of Patent: December 31, 1991Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Franz-Josef Carduck, Lutz Jeromin, Gerd Geobel, Wilhelm Johannisbauer, Georg Fieg, Theo Fleckenstein
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Patent number: 5073650Abstract: A process for the preparation of 1,4-butanediol by catalytically hydrogenating maleic anhydride in the presence of an alcohol, at elevated temperature and elevated pressure and with the aid of a cobalt-containing catalyst comprises partially hydrogenating the reaction mixture in a first hydrogenation step at from 100.degree. to 200.degree. C. and at from 30 to 200 bar and subsequently post-hydrogenating the product of this first hydrogenation step, without further work-up at higher temperature and pressure than in the first hydrogenation step, in a second hydrogenation step at from 200.degree. to 300.degree. C. and at from 200 to 350 bar.Type: GrantFiled: March 20, 1991Date of Patent: December 17, 1991Assignee: BASF AktiengesellschaftInventors: Uwe Stabel, Hans-Juergen Gosch, Rolf Fischer, Wolfgang Harder, Claus Hechler
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Patent number: 5037996Abstract: A process of producing 1,4-butanediol by catalytically hydrogenating maleic acid anhydride and/or succinic acid anhydride in a gas phase and in the presence of a catalyst.Type: GrantFiled: July 16, 1990Date of Patent: August 6, 1991Assignee: Tonen CorporationInventors: Sadakatsu Suzuki, Hiroyuki Inagaki, Hiroshi Ueno
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Patent number: 5030771Abstract: A method of producing aliphatic and cycloaliphatic diols by catalytic hydrogenation of dicarboxylic acid esters by the use of a copper chromite catalyst in which the copper content (calculated as CuO) is 40-47 wt. %, and the chromium content (calculated as Cr.sub.2 O.sub.3) is 40-47 wt. %, and barium is also present in the amount of up to 10 wt. % (calculated as BaO) under mild temperature and pressure conditions is disclosed. The method produces diols without the formation of high boiling materials and does not require purification of the product diols by overhead distillation.Type: GrantFiled: December 20, 1989Date of Patent: July 9, 1991Assignee: Huels AktiengesellschaftInventors: Werner Fuhrmann, Gunther Bub, Manfred zur Hausen
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Patent number: 5030773Abstract: A process for the production of butanediol from the hydrogenation of .gamma.-butyrolactone is provided. The process involves passing vaporized .gamma.-butyrolactone, water and hydrogen over a copper zinc catalyst. The incorporation of water with the .gamma.-butyrolactone and hydrogen results in increased productivity of butanediol.Type: GrantFiled: July 25, 1990Date of Patent: July 9, 1991Assignee: General Electric CompanyInventors: Norman E. Johnson, Richard T. Miskinis, Richard A. Shafer
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Patent number: 5030328Abstract: A method of separating .gamma.-butyrolactone from a mixture containing ethanol, tetrahydrofuran, water, n-butanol, 1,4-butanediol, diethyl succinate and .gamma.-butyrolactone, by distillation in vacuum columns.Type: GrantFiled: November 5, 1990Date of Patent: July 9, 1991Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Peter Stops, Erwin Brunner, Rudolf Weigand
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Patent number: 5025113Abstract: A tertiary butyl hydroperoxide feedstock, such as one prepared from the reaction product formed by the reaction of isobutane with molecular oxygen and which feedstock comprises tertiary butyl hydroperoxide dissolved in tertiary butyl alcohol, is charged to a catalytic decomposition zone where the tertiary butyl hydroperoxide is catalytically decomposed in the presence of a soluble catalyst system to provide a decomposition reaction product characterized by a high conversion rate and a high selectivity of tertiary butyl hydroperoxide to tertiary butyl alcohol, the catalyst system being composed of a soluble iron compound and a soluble ruthenium compound.Type: GrantFiled: January 29, 1990Date of Patent: June 18, 1991Assignee: Texaco Chemical CompanyInventors: John R. Sanderson, John F. Knifton
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Patent number: 4982020Abstract: In the direct catalytic hydrogenation of glyceride oils, the glyceride oils are continuously reacted with hydrogen under pressures of from 20 to 300 bar and at temperatures of from 160.degree. to 250.degree. C. with molar ratios of hydrogen to fatty acid residues in the glyceride oil substrate of from 10:1 to 500:1, the reaction being carried out over catalysts which contain from 30 to 40% by weight copper, from 23 to 30% by weight chromium, from 1 to 7% by weight barium (% by weight, based in each case on oxidic catalyst mass) and, if desired, other transition metals in the form of their oxides and which, after calcination of the components forming the catalyst mass, are converted into shaped particulate and/or granulated elements with from 1 to 10% by weight, based on oxidic catalyst, of at least one binder, and which have been activated with hydrogen or a hydrogen-containing gas mixture.Type: GrantFiled: December 20, 1989Date of Patent: January 1, 1991Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Franz-Josef Carduck, Jurgen Falbe, Theo Fleckenstein, Joachim Pohl
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Patent number: 4977284Abstract: A process of producing 1,4-butanediol and tetrahydrofuran by catalytically hydrogenating maleic acid anhydride and/or succinic acid anhydride in a gas phase and in the presence of a catalyst.Type: GrantFiled: December 13, 1989Date of Patent: December 11, 1990Assignee: Tonen CorporationInventors: Sadakatsu Suzuki, Hiroyuki Inagaki, Hiroshi Ueno
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Patent number: 4973769Abstract: 1,2,4-Butanetriol is prepared by catalytic hydrogenation of malic esters over a copper-containing catalyst by passing the esters over the fixed-bed catalyst at from 130.degree. to 190.degree. C. under hydrogen partial pressures of from 100 to 300 bar while substantially avoiding the formation of a gas phase.Type: GrantFiled: February 3, 1989Date of Patent: November 27, 1990Assignee: BASF AktiengesellschaftInventors: Herbert Mueller, Walter Mesch, Klaus Broellos
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Patent number: 4973717Abstract: An alcohol and/or an ether is produced from a carboxylic acid ester by reacting the ester 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 of the Elements and (ii) at least one metal capable of alloying with the aforesaid Group VIII noble metal.Type: GrantFiled: December 1, 1989Date of Patent: November 27, 1990Assignee: BP Chemicals LimitedInventor: Peter S. Williams