Catalyst Utilized Patents (Class 568/881)
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Patent number: 6288288Abstract: A process for preparing saturated alcohols comprising effecting an aldol condensation of alkyl methyl ketones of 6 to 8 carbon atoms which are branched at the &bgr;-carbon atom with aldehydes of 4 to 15 carbon atoms which are branched at the &agr;-carbon atom to form &agr;,&bgr;-unsaturated ketones and subsequent hydrogenation of the &agr;,&bgr;-unsaturated ketones to obtain alcohols, wherein the aldol condensation is carried out at a temperature of 60 to 130° C. in the presence of a 30-55% strength aqueous solution of an alkali metal hydroxide resulting in very low by-product formation.Type: GrantFiled: November 25, 1998Date of Patent: September 11, 2001Assignee: Celanese GmbHInventor: Helmut Springer
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Patent number: 6278030Abstract: An improved process for preparing alcohols by the Oxo process. More particularly this invention relates to an improvement in the hydrogenation step of the Oxo process characterized in the use of certain bulk multimetallic hydrogenation catalysts comprised of at least one Group VIII non-noble metal and at least two Group VIB metals.Type: GrantFiled: January 14, 2000Date of Patent: August 21, 2001Assignee: Exxon Chemical Patents, Inc.Inventors: Jose Manuel Vargas, Kenneth Lloyd Riley
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Patent number: 6245952Abstract: The present invention relates to a process for the preparation of alcohols by reduction of the carbonyl function in substrates belonging to the class of aldehydes, ketones, esters or lactones, which substrates may contain unsaturated functions other than carbonyl. This process includes the steps of reacting the carbonyl substrate with stoichiometric amounts of a silane in the presence of catalytic amounts of an active zinc compound which is monomeric and not a hydride, hydrolyzing the thus-obtained siloxane with a basic agent, and separating and purifying, if necessary, the thus-obtained alcohol. The catalytically active compound is generally obtained by the reaction of an oligomeric or polymeric precursor compound of zinc with a complexing agent.Type: GrantFiled: March 1, 1999Date of Patent: June 12, 2001Assignee: Firmenich SAInventor: Hubert Mimoun
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Patent number: 6239318Abstract: The invention relates to a process for the selective hydrogenation of reaction mixtures from the hydroformylation of C5 to C24 olefins using hydrogen and a supported catalyst which, as active components, comprises copper, nickel and chromium.Type: GrantFiled: September 15, 1999Date of Patent: May 29, 2001Assignee: Oxeno Olefinchemie GmbHInventors: Joachim Schuler, Alfred Kaizik, Bernhard Scholz, Wilfried Bueschken, Wilhelm Droste
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Patent number: 6218585Abstract: A method of increasing enantioselectivity in a reduction reaction of a prochiral substrate with a borane reagent including a borohydride species (for example, a borohydride stabilized borane-tetrahydrofuran complex) catalyzed by a chiral catalyst includes the step of maintaining the concentration of borohydride species in the borane reagent below approximately 0.005 M during the reduction of the prochiral substrate. A method of increasing enantioselectivity in a reduction reaction of a prochiral substrate with a borane reagent including a borohydride species that is catalyzed by a chiral catalyst includes the step of reducing the detrimental effect the borohydride species has on enantioselectivity by adding a Lewis acid. For example, the prochiral substrate can be a ketone and the chiral catalyst can be a chiral oxazaborolidine.Type: GrantFiled: April 20, 2000Date of Patent: April 17, 2001Assignee: Mine Safety Appliances CompanyInventors: Karl Matos, Joseph A. Corella, II, Elizabeth R. Burkhardt, Shawn M. Nettles
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Patent number: 6211419Abstract: A method for operating an epoxide containing system which contains a catalyst is disclosed. The method comprises feeding carbon dioxide to the epoxide containing system at an amount of from 0.01 to 5.0 weight percent; and maintaining the epoxide containing system at a temperature of from 100° C. to 150° C. The catalyst has a half life of at least 40 days at 120° C. The present invention allows anion exchange resins in the bicarbonate form to be used for the hydrolysis of ethylene oxide at temperatures exceeding 100° C. The rate of catalyst swelling is minimized and lifetime of the catalyst enhanced.Type: GrantFiled: April 24, 2000Date of Patent: April 3, 2001Assignee: The Dow Chemical CompanyInventors: Gary R. Strickler, Von G. Landon, Guo-Shuh John Lee
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Patent number: 6207865Abstract: A carbonyl compound or a mixture of two or more carbonyl compounds is catalytically hydrogenated in the presence of a Raney copper catalyst in the form of nuggets.Type: GrantFiled: January 11, 2000Date of Patent: March 27, 2001Assignee: BASF AktiengesellschaftInventors: Boris Breitscheidel, Marc Walter, Detlef Kratz, Gerhard Schulz, Manfred Sauerwald
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Patent number: 6191323Abstract: A process for the reduction of ketones or aldehydes to alcohols has been developed. The process involves contacting the ketone or aldehyde with a primary or secondary alcohol and a catalyst at reduction conditions. The catalyst is a molecular sieve having the empirical formula: (MwSnxTiySi1-x-y-zGez)O2 where M is a trivalent metal such as aluminum or boron. These molecular sieves have a microporous three dimensional framework structure of at least SiO2 and SnO2 tetrahedral units, a crystallographically regular pore system and the characteristic x-ray diffraction pattern of zeolite beta.Type: GrantFiled: April 25, 2000Date of Patent: February 20, 2001Assignee: UOP LLCInventors: Laszlo T. Nemeth, Avelino Corma Canos, Susana Valencia Valencia, Jaime G. Moscoso, Marcelo Eduardo Domine
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Patent number: 6156933Abstract: Process for the selective hydrogenation of alphatic or aromatic substrates under supercritical or near critical conditions. Hydrogenation is effected using a heterogeneous catalyst in a continuous flow reactor containing a supercritical or near critical reaction medium and selectively of product formation is achieved by varying one or more of the temperature, pressure, catalyst and flow rate.Type: GrantFiled: February 18, 1999Date of Patent: December 5, 2000Assignees: Degussa-Huls AG, Thomas Swan & Co. Ltd.Inventors: Martyn Poliakoff, Thomas M. Swan, Thomas Tacke, Martin G. Hitzler, Stephen K. Ross, Stefan Wieland
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Patent number: 6156940Abstract: The present invention relates to a process for producing optically active halomethyl phenyl carbinols of the formula (1), comprising reducing halomethyl phenyl ketones of the formula (2) using an asymmetric reducing agent obtained from boranes and optically active .alpha.-phenyl-substituted-.beta.-amino alcohols of the formula (3) or optically active .alpha.-non-substituted-.beta.-amino alcohols of the formula (4).The present invention further relates to a process for producing optically active carbinols, comprising reacting a prochiral ketone with, an asymmetric reducing agent obtained from optically active .beta.-amino alcohols of the formula (5), a metal boron hydride and Lewis acid or lower dialkyl sulfuric acid. All of the formulas (1) to (5) are the same as shown in the specification.Type: GrantFiled: April 8, 1998Date of Patent: December 5, 2000Assignees: Sumika Fine Chemicals Company, Limited, Sumitomo Chemical Company, LimitedInventors: Kenji Saito, Norio Kometani, Azusa Fujiwara, Yukio Yoneyoshi, Gohfu Suzukamo
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Patent number: 6150567Abstract: The present invention provides a process for reducing carbonyl compounds to hydroxy compounds, in particular stereoselectively reducing .alpha.-aminohaloketone derivatives, under mild conditions in an easy and simple manner, which comprises reacting a carbonyl compound of the general formula (1) with an organoaluminum compound of the general formula (4) to provide the corresponding alcohol compound of the general formula (5).Type: GrantFiled: December 29, 1997Date of Patent: November 21, 2000Assignee: Kaneka CorporationInventors: Tadashi Sugawa, Tadashi Moroshima, Kenji Inoue, Kazunori Kan
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Patent number: 6124509Abstract: The present invention is a process for the catalytic hydrogenation of ketones and aldehydes to alcohols at low temperatures and pressures using organometallic molybdenum and tungsten complexes. The functional group is selected from groups represented by the formulas R(C.dbd.O)R' and R(C.dbd.O)H, wherein R and R' are selected from hydrogen or any alkyl or aryl group. The active catalyst for the process has the form: [CpM(CO).sub.2 (PR*.sub.3) L].sup.+ A.sup.-, where Cp=.eta..sup.5 -R.sup..tangle-solidup..sub.m C.sub.5 H.sub.5-m and R.sup..tangle-solidup. represents an alkyl group or a halogen (F, Cl, Br, I) or R.sup..tangle-solidup. =OR' (where R'=H, an alkyl group or an aryl group) or R.sup..tangle-solidup. =CO.sub.2 R' (where R'=H, an alkyl group or an aryl group) and m=0 to 5; M represents a molybdenum atom or a tungsten atom; R*.sub.3 represents three hydrocarbon groups selected from a cyclohexyl group (C.sub.6 H.sub.11), a methyl group (CH.sub.3), and a phenyl group (C.sub.6 H.sub.Type: GrantFiled: January 22, 1999Date of Patent: September 26, 2000Assignee: Brookhaven Science AssociatesInventors: Mark Voges, R. Morris Bullock
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Patent number: 6096931Abstract: In a process for preparing alcohols comprising the hydrogenation of aldehydes in the presence of a hydrogenation catalyst in the gas phase, the improvement comprising adding nitrogen-containing bases to the aldehyde to be hydrogenated, whereby the formation of by-products is largely suppressed and isolation of the desired alcohols in high selectivity and correspondingly high yield is made possible.Type: GrantFiled: December 3, 1998Date of Patent: August 1, 2000Assignee: Celanese GmbHInventors: Carl Dieter Frohning, Wolfgang Zgorzelski, Hans Liebern
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Patent number: 6054627Abstract: Disclosed are catalysts in powdered form comprising a major amount of the oxides of a first metal selected from copper or zinc, a second metal selected from chromium, molybdenum, tungsten and vanadium, and optionally, a minor amount of the oxide of a promoter metal selected from the group consisting of manganese, barium, zinc, nickel, cobalt, cadmium, iron and any combination thereof provided that the promoter metal is not zinc if the first metal is zinc, wherein the average particle diameter of the powder is from about 6 to about 20 microns; and the particle surface area is from about 20 to about 70 m.sup.2 /g. Also disclosed is a process for preparing such catalysts and a process for hydrogenating aldehydes, ketones, carboxylic acids and carboxylic acid esters with catalysts of the type described.Type: GrantFiled: May 27, 1992Date of Patent: April 25, 2000Assignee: Engelhard CorporationInventors: Deepak S. Thakur, Eugene Palka, Thomas I. Sullivan, Eugene Nebesh, Brian D. Roberts
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Patent number: 6046127Abstract: Aldehydes, ketones, esters and lactones may be reduced using a reductant system consisting of a silane derivative and a metal hydride to give good yields of the corresponding alcohols. The reductant system used in the method enables preferential reduction of the carbonyl function. In one embodiment, the reductant system consists of polymethylhydroxysilane and a metal hydride, the hydride being prepared in situ or ex situ from a metal salt or complex by means of a reaction with a reducing agent.Type: GrantFiled: July 15, 1998Date of Patent: April 4, 2000Assignee: Firmenich SAInventor: Hubert Mimoun
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Patent number: 6037505Abstract: The anantoselective borane reduction of prochiral ketones to optically pure alcohols is effectively achieved by performing the reduction in the precence of catalytic amounts of the new and valuable oxazaborolidine compounds of formulas (I) and (II). The compounds of formulas (I) and (II) may be isolated and purified prior to use in the reduction reactions or the compounds of formulas (I) and (II) may be generated in situ.Type: GrantFiled: April 26, 1999Date of Patent: March 14, 2000Assignee: Pfizer Inc.Inventor: George Joseph Quallich
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Patent number: 6008419Abstract: A 2,3-dihalopropanol is made by reacting 2,3-dihalopropanal with molecular hydrogen in the presence of a transition metal-containing catalyst, under conditions such that 2,3-dihalopropanol is formed. The reaction is particularly useful, for example, as Step (3) in a process to make epihalohydrin which may be generally prepared by:(1) reacting a 3-carbon hydrocarbon with an oxidizing agent to form acrolein;(2) reacting acrolein with a molecular halogen to form 2,3-dihalopropanal;(3) reducing 2,3-dihalopropanal with molecular hydrogen to form 2,3-dihalopropanol; and(4) cyclizing 2,3-dihalopropanol to make epihalohydrin.The process produces epihalohydrin using only about one mole of halogen per mole of epihalohydrin. It also uses substantially less water than existing processes.Type: GrantFiled: December 19, 1997Date of Patent: December 28, 1999Assignee: The Dow Chemical CompanyInventors: P. J. Thomas, R. Garth Pews, Paul C. Vosejpka, George J. Frycek
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Patent number: 5922921Abstract: Disclosed is the use of a Raney cobalt catalyst in the hydrogenation process for the production of n-butanol.A process for the production of purified n-butanol comprising contacting in a hydrogenation zone n-butyraldehyde and hydrogen with an active porous cobalt catalyst under hydrogenation conditions of temperature and pressure for the production of alcohols from aldehydes, either in the substantial absence of water, or in the presence of water in an amount up to about 6 wt % based on the weight of the liquid hydrogenation reaction product to produce said reaction product comprising n-butanol, and purifying said reaction product by fractional distillation in the presence of about 0.01 to about 6 wt % of water, based on the total weight of feed to the fractionating column.Type: GrantFiled: October 27, 1997Date of Patent: July 13, 1999Assignee: Celanese International CorporationInventors: Jerry D. Unruh, Debra A. Ryan, Shannon L. Dugan
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Patent number: 5874649Abstract: The object of the present invention resides in efficiently providing unsaturated alcohol from an .alpha.,.beta.-unsaturated aldehyde.The present invention provides a process for preparing unsaturated alcohol by selectively reducing the aldehyde group of an .alpha.,.beta.-unsaturated aldehyde in the presence of a primary or a secondary alcohol having 2 to 8 carbon atoms using an aluminum alcoholate to produce an unsaturated alcohol such as compounds represented by the formula (III). ##STR1## (wherein R represents an alkyl group having 1 to 3 carbon atoms) wherein the reaction is carried out with addition of a protonic acid.Type: GrantFiled: November 5, 1997Date of Patent: February 23, 1999Assignee: Kao CorporationInventors: Shigeyoshi Tanaka, Shinji Kotachi, Junji Koshino, Junko Yamamoto
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Patent number: 5874652Abstract: A process for hydrogenating aqueous mixtures of 4-hydroxybutanal and 3-hydroxy-2-methylpropanal is disclosed. The process uses a metallic Pt--Ru catalyst supported on .gamma.-alumina. The process gives improved yields of 2-methyl-1,3-propanediol while minimizing the formation of unwanted by-products such as isobutyl alcohol and tetrahydrofuran.Type: GrantFiled: October 18, 1993Date of Patent: February 23, 1999Assignee: Arco Chemical Technology, L.P.Inventors: Rangasamy Pitchai, Thomas S. Zak
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Patent number: 5866725Abstract: A process for the production of purified n-propanol comprising contacting in a hydrogenation zone propionaldehyde and hydrogen with an active porous cobalt catalyst under hydrogenation conditions of temperature and pressure for the production of alcohols from aldehydes, either in the substantial absence of water, or in the presence of water in an amount up to about 3 wt % based on the weight of the liquid hydrogenation reaction product, to produce said reaction product comprising n-propanol, and purifying said reaction product by fractional distillation in the substantial absence of water, or in the presence of water in an amount up to about 3 wt % based on the total weight of feed to the fractionating column.Type: GrantFiled: December 11, 1997Date of Patent: February 2, 1999Assignee: Celanese International CorporationInventors: Jerry D. Unruh, Debra A. Ryan, Shannon L. Dugan
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Patent number: 5852221Abstract: An optically active .beta.-aminoalkoxyborane complex of the formula (I): ##STR1## wherein R.sup.1 is C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.7 -C.sub.11 aralkyl or C.sub.6 -C.sub.10 aryl, R.sup.2 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.7 cycloalkyl or C.sub.7 -C.sub.11 aralkyl, or R.sup.1 and R.sup.2 together form (CH.sub.2)n wherein n is 3 or 4, and Ar is naphthyl, anthryl or phenanthryl, which may be substituted by from 1 to 3 substituents selected from the group consisting of halogen, nitro, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.7 -C.sub.11 aralkyl, C.sub.6 -C.sub.10 aryl, C.sub.1 -C.sub.6 alkoxy and styrene polymer substituents.Type: GrantFiled: April 29, 1997Date of Patent: December 22, 1998Assignee: Nissan Chemical Industries Ltd.Inventors: Hiroshi Kashihara, Mikio Suzuki, Yoshio Ohara
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Patent number: 5831135Abstract: The present invention relates to a process for the catalytic selective hydrogenation of a polyunsaturated organic compound, wherein the hydrogenation is carried out in a plurality of two or more series-connected loops, wherein each loop involves the use of one reactor, which comprises:(a) feeding the polyunsaturated organic compound and hydrogen to an upper part of a reactor to catalytically hydrogenate said the polyunsaturated organic compound to produce a hydrogenation product,(b) recycling a portion of said hydrogenation product back into said upper part of said reactor,(c) feeding the remainder of said hydrogenation product from said reactor to an upper part of a subsequent reactor wherein the polyunsaturated organic compound is catalytically hydrogenated to produce a subsequent hydrogenation product, and wherein a portion of said subsequent hydrogenation product has been recycled and is fed with said remainder of said hydrogenation product to said upper part of said subsequent reactor,(d) repeating stepType: GrantFiled: October 6, 1997Date of Patent: November 3, 1998Assignee: Huels AktiengesellschaftInventors: Wilfried Bueschken, Juergen Hummel
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Patent number: 5831133Abstract: Aldehydes, ketones, esters and lactones may be reduced using a reductant system consisting of polymethylhydroxysilane (PMHS) and a metal hydride to give good yields of the corresponding alcohols. The reductant system used in the method enables preferential reduction of the carbonyl function.Type: GrantFiled: May 15, 1996Date of Patent: November 3, 1998Assignee: Firmenich SAInventor: Hubert Mimoun
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Patent number: 5763690Abstract: Trimethylolpropane of high purity is efficiently made by mixing the aldol reaction product of formaldehyde and n-butyraldehyde with at least about 20 wt % of a lower alcohol prior to hydrogenation. The alcohol addition also promotes hydrogenolysis of by-product esters at pressures below 3000 psig and allows recovery of high purity product by simple distillation.Type: GrantFiled: August 2, 1996Date of Patent: June 9, 1998Assignee: Aristech Chemical CorporationInventors: Jeffrey S. Salek, Joseph Pugach, Carole L. Elias, Leonard A. Cullo
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Patent number: 5741475Abstract: A catalytic reaction apparatus includes a catalytic reaction vessel containing a catalyst for an exothermic reaction. First and second catalyst regions contain a catalyst and have different catalytic performances from one another. At least two raw materials are introduced in the catalytic reaction vessel and passed through the first and second catalyst regions to react to generate heat. The heat is transferred to a heat medium arranged outside and contacting the catalytic reaction vessel so that distribution of temperature is controlled in the catalytic reaction vessel. The difference in catalytic performance is achieved by controlling concentration of the catalyst or by using different catalyst species.Type: GrantFiled: September 30, 1996Date of Patent: April 21, 1998Assignee: Agency of Industrial Science & TechnologyInventors: Takumi Takashima, Tadayoshi Tanaka, Takahiro Fujii, Takuya Doi
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Patent number: 5728891Abstract: A process for the preparation of 3,3,5-trimethylcyclohexanone by catalytic hydrogenation of isophorone, wherein the hydrogenation is carried out in a plurality of two or more series-connected loops, wherein each loop involves the use of one reactor, which comprises:(a) feeding isophorone and hydrogen to an upper part of a reactor to catalytically hydrogenate said isophorone to produce a hydrogenation product,(b) recycling a portion of said hydrogenation product back into said upper part of said reactor,(c) feeding the remainder of said hydrogenation product from said reactor to an upper part of a subsequent reactor wherein isophorone is catalytically hydrogenated to produce a subsequent hydrogenation product, and wherein a portion of said subsequent hydrogenation product has been recycled and is fed with said remainder of said hydrogenation product to said upper part of said subsequent reactor,(d) repeating step (c) until the subsequent reactor is the last reactor,(e) recovering the remainder of said subsequeType: GrantFiled: June 26, 1996Date of Patent: March 17, 1998Assignee: Huels AktiengesellschaftInventors: Wilfried Bueschken, Juergen Hummel
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Patent number: 5684215Abstract: A process for the preparation of alcohols by reaction of organic carbonyl compounds or mixtures containing them with hydrogen over a supported catalyst containing nickel, aluminum oxide, and zirconium dioxide at elevated temperature and, if appropriate, under elevated pressure. Ketones, aldehydes and derivatives thereof are reacted as the carbonyl compounds at temperatures of 60.degree. to 150.degree. C.Type: GrantFiled: December 28, 1992Date of Patent: November 4, 1997Assignee: Hoechst AktiengesellschaftInventors: Gerhardt Horn, Carl Dieter Frohning
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Patent number: 5675045Abstract: The present invention relates to a process for the catalytic selective hydrogenation of a polyunsaturated organic compound, wherein the hydrogenation is carried out in a plurality of two or more series-connected loops, wherein each loop involves the use of one reactor, which comprises:(a) feeding the polyunsaturated organic compound and hydrogen to an upper part of a reactor to catalytically hydrogenate said the polyunsaturated organic compound to produce a hydrogenation product,(b) recycling a portion of said hydrogenation product back into said upper part of said reactor,(c) feeding the remainder of said hydrogenation product from said reactor to an upper part of a subsequent reactor wherein the polyunsaturated organic compound is catalytically hydrogenated to produce a subsequent hydrogenation product, and wherein a portion of said subsequent hydrogenation product has been recycled and is fed with said remainder of said hydrogenation product to said upper part of said subsequent reactor,(d) repeating stepType: GrantFiled: June 26, 1996Date of Patent: October 7, 1997Assignee: Huels AktiengesellschaftInventors: Wilfried Bueschken, Juergen Hummel
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Patent number: 5650546Abstract: A process for the hydrogenation of organic compounds using water soluble catalyst in a biphasic media by: (A) forming an organo-water dispersion of (i) an organic phase having (a) an organic compound and (b) an organic solvent, and (ii) an aqueous phase having a water soluble group VIII metal catalyst composition and a water soluble ligand; and (B) contacting said dispersion with hydrogen to provide an interfacial reaction between said organic compound and said hydrogen, giving significant enhancement in the rate of reaction to produce saturated organic compound as compared to a reaction carried out in the absence of said water immiscible ligand.Type: GrantFiled: December 16, 1994Date of Patent: July 22, 1997Assignee: Council of Scientific Industrial Resear.Inventors: Raghunath Vitthal Chaudhari, Bhalchandra Mahadeo Bhanage, Sunil Sadashiv Divekar, Raj Madhukar Deshpande
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Patent number: 5600030Abstract: A process for hydrogenation of an aldehyde selected from the group consisting of propanal, n-butanal, and i-butanal comprising contacting said aldehyde with hydrogen in the presence of a hydrogenation catalyst comprising in the reduced state25% to 50% by weight of metallic nickel10% to 35% by weight of nickel oxide4% to 12% by weight of magnesium oxide1% to 5% by weight of sodium oxidethe remainder being a water insoluble support material, wherein the total of said nickel and said nickel oxide is 40% to 70% by weight based on said catalyst, said catalyst having a total BET surface area of 80 to 200 m.sup.2 /g and a total pore volume, determined by mercury porosimetry, of 0,35 to 0.6 ml/g,said total volume consisting of 30% to 60% of said volume from pores having pore radii equal to or less than 40 .ANG., 4% to 10% of said volume from pores having pore radii from more than 40 .ANG. to 300 .ANG., and 30% to 60% of said volume from pores having pore radii from more than 300 .ANG. to 5000 .ANG..Type: GrantFiled: May 9, 1995Date of Patent: February 4, 1997Assignee: Hoechst AktiengesellschaftInventors: Gregor Deckers, Gerhard Diekhaus, Bernd Dorsch, Carl D. Frohning, Gerhardt Horn, Horst B. Horrig
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Patent number: 5583266Abstract: A two-step integrated process for the generation of diisopropyl ether from a crude by-product acetone stream which comprises:a) Hydrogenating said crude acetone over a supported, hydrogenation catalyst to give an isopropanol-rich effluent;b) passing said isopropanol-rich intermediate directly to a second reactor, andc) subject said IPA to dehydration conditions in the presence of hydrogen and a strong acid zeolite catalyst from the group consisting of .beta.-zeolite, optionally modified with one or more metals from Groups IB, VIB, VIIB and VIII of the Periodic Table, and a dealuminized Y-zeolite.Type: GrantFiled: May 2, 1994Date of Patent: December 10, 1996Assignee: Texaco Inc.Inventors: Robert J. Taylor, Jr., Pei-Shing E. Dai, John F. Knifton
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Patent number: 5583270Abstract: Disclosed are the improvements of a process for the preparation of 1,3-butylene glycol, in which the generation of by-products can be decreased, resulting in being capable of productiong 1,3-butylene glycol having high quality (e.g. an odorless, so-called "cosmetic grade") at a high-yield.Type: GrantFiled: June 23, 1994Date of Patent: December 10, 1996Assignee: Daicel Chemical Industries, Ltd.Inventor: Kazuhisa Nishiguchi
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Patent number: 5569792Abstract: A copper oxide/zinc oxide/aluminum oxide catalyst which contains, per 100 parts of copper oxide, 40 to 130 parts zinc oxide, 2 to 50 parts aluminum oxide, and 1 to 4 parts soium oxide. It has a total BET surface area of 50 to 100 m.sup.2 /g, and 75% to 95% of the total surface area is made up by pores having radii of 9 to 1000 nm, and 5% to 25% of the total surface area is made up by pores having radii of less than 9 nm. The catalyst is useful for hydrogenation of various organic compounds.Type: GrantFiled: March 17, 1995Date of Patent: October 29, 1996Assignee: Hoechst AktiengesellschaftInventors: Gregor Deckers, Gerhardt Horn
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Patent number: 5552548Abstract: The borane reduction of prochiral ketones to optically pure alcohols is effectively achieved by the utilization of catalytic amounts of the new and valuable oxazaborolidine catalysts of formula (I).Type: GrantFiled: October 13, 1994Date of Patent: September 3, 1996Assignee: Pfizer Inc.Inventor: George J. Quallich
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Patent number: 5550302Abstract: A method for producing an alcohol, which comprises reacting an aldehyde with hydrogen in a gas phase in the presence of a hydrogenation catalyst to form a corresponding saturated alcohol, wherein a reduced product of a catalyst precursor composition comprising components represented by the following formula (I):Cu(a)--Cr(b)--Zn(c)--Mn(d)--Ba(e)--X(f) (I)wherein X is a transition metal of Group 8 or 4A of thePeriodic Table, and a to f represent the contents of the respective components as converted to their oxides and have the following values:a: 20 to 50 wt %b: 0 to 50 wt %c: 0 to 50 wt %d: 0.1 to 5.0 wt %e: 0.1 to 5.0 wt %f: 0.01 to 3.0 wt %is used as the hydrogenation catalyst.Type: GrantFiled: March 16, 1995Date of Patent: August 27, 1996Assignee: Mitsubishi Chemical CorporationInventors: Tomoyuki Mori, Kouichi Fujita, Hiroki Hinoishi
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Patent number: 5495055Abstract: A deactivated supported ruthenium catalyst which has been used to continuously hydrogenate an aqueous acetone stream is regenerated by contacting with steam at an elevated temperature. Periodic regeneration in this manner serves to maintain a high rate of reaction in a process which converts acetone to isopropanol.Type: GrantFiled: February 13, 1995Date of Patent: February 27, 1996Assignee: Arco Chemical Technology, L.P.Inventor: Michael A. Rueter
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Patent number: 5495054Abstract: A method for the enantioselective reduction of prochiral ketones using catalytic amounts of tetrahydroindeno[1,2-d][1,3,2] oxazaboroles of formula II is disclosed. ##STR1## The oxazaboroles can be generated in situ from the corresponding cis-1-amino-2-indanols or imino indanols (III) ##STR2## Novel compounds of formulas II and III are also disclosed.Type: GrantFiled: May 31, 1994Date of Patent: February 27, 1996Assignee: Sepracor, Inc.Inventors: Yun Gao, Yaping Hong, Charles M. Zepp
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Patent number: 5491266Abstract: This invention relates to asymmetric syntheses in which a prochiral or chiral compound is contacted in the presence of an optically active metal-ligand complex catalyst to produce an optically active product.Type: GrantFiled: June 20, 1994Date of Patent: February 13, 1996Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: James E. Babin, Gregory T. Whiteker
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Patent number: 5476972Abstract: Disclosed is a one-step method for synthesis of ethers from mixtures of acetone and t-butyl alcohol which comprises reacting an acetone-rich feed over a bifunctional catalyst comprising 5%-45% by weight hydrogenation catalyst on 55%-95% of the total catalyst weight of a support comprising a zeolite and a Group III or IV oxide.Type: GrantFiled: January 28, 1994Date of Patent: December 19, 1995Assignee: Texaco Chemical Inc.Inventors: Pei-Shing E. Dai, Robert J. Taylor, Jr., John F. Knifton, Bobby R. Martin
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Patent number: 5475161Abstract: A process for the preparation of alcohols by reaction of organic carbonyl compounds with hydrogen in two stages at elevated temperature and, optionally, elevated pressure. In the first stage, hydrogen and the carbonyl compounds are fed as a gas to a copper-containing catalyst and reacted to 80 to 99.5 percent of the theoretical conversion. In the second stage, the reaction product of the first stage is fed to a nickel/alumina/zirconium dioxide catalyst as a liquid, along with hydrogen. The carbonyl compounds used include aldehydes and their derivatives and, in particular, aliphatic unsaturated and saturated aldehydes.Type: GrantFiled: January 17, 1992Date of Patent: December 12, 1995Assignee: Hoechst AktiengesellschaftInventors: Gerhardt Horn, Carl D. Frohning, Hans Liebern, Wolfgang Zgorzelski
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Patent number: 5449838Abstract: Disclosed is a two-step process for the generation of isopropyl t-butyl ether from a crude by-product acetone stream which comprises:a) Hydrogenating said crude acetone over a bulk metal, nickel-rich catalyst to give an isopropanol-rich effluent;b) subjecting said isopropanol-rich intermediate to etherification conditions in the presence of a strong acid catalyst selected from:(1) a cationic resin;(2) a .beta.-zeolite;(3) dealuminized Y-zeolites; and(4) metal-modified .beta.-zeolites.Type: GrantFiled: December 30, 1993Date of Patent: September 12, 1995Assignee: Texaco Chemical Inc.Inventors: John F. Knifton, Ernest L. Yeakey, Pei-Shing E. Dai
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Patent number: 5430198Abstract: Disclosed is a two-step process for the generation of diisopropyl ether from a crude by-product acetone stream which comprises:a) Hydrogenating said crude acetone over a bulk-metal, nickel-rich catalyst to give an isopropanol-rich effluent;b) Dehydrating said isopropanol-rich intermediate in the presence of a strong acid zeolite catalyst from the group consisting of .beta.-zeolite, optionally modified with one or more metals from Group IB, VB, VIB, VIIB and VIII of the Periodic Table, and a dealuminized Y-zeolite, wherein the dehydration temperature is from about 80.degree. C. to 200.degree. C.Type: GrantFiled: November 8, 1993Date of Patent: July 4, 1995Assignee: Texaco Chemical Inc.Inventors: John F. Knifton, Pei-Shing E. Dai
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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: 5399793Abstract: The hydrogenation steps and hydrofinishing steps of the cobalt catalyst oxo process for preparation of the alcohols by the hydroformylation of olefin are carried out using a catalyst containing Ni/Mo on alumina or silica alumina prepared by depositing an organic acid solution of Ni and Mo salts on the support, the acid being phosphorous free.Type: GrantFiled: November 29, 1993Date of Patent: March 21, 1995Assignee: Exxon Chemical Patents Inc.Inventors: Jose M. Vargas, Magdiel Agosto, Kenneth L. Riley
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Patent number: 5382716Abstract: Mixtures of isomeric decyl alcohols obtained by hydroformylation of butadiene to produce aldehyde mixtures, condensation of the aldehyde mixtures, isolated from the reaction product, to form an aldol mixture, and isolation and hydrogenation of the aldol mixture. The mixture of isomeric decyl alcohols, esterified using phthalic acid, gives a mixture of isomeric decyl phthalates which are plasticizers having excellent cold properties.Type: GrantFiled: March 23, 1993Date of Patent: January 17, 1995Assignee: Hoechst AktiengesellschaftInventors: Helmut Bahrmann, Wolfgang Greb, Peter Heymanns, Peter Lappe, Jurgen Szameitat, Thomas Muller, Ernst Wiebus
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Patent number: 5354915Abstract: This invention provides an improved process for converting .alpha.,.beta.-olefinically unsaturated aldehydic or ketonic compounds into the corresponding allylic alcohol using an alcohol as a hydrogen donor. This process is conducted in the presence of a supported tetragonal zirconium oxide catalyst or supported HfO.sub.2, V.sub.2 O.sub.5, NbO.sub.5, TiO.sub.2 and Ta.sub.2 O.sub.5 catalysts.Type: GrantFiled: December 21, 1992Date of Patent: October 11, 1994Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Walter T. Reichle
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Patent number: 5347056Abstract: This invention relates to a process for producing .alpha., .beta.-unsaturated alcohol, which uses unsaturated aldehyde as a starting material, and in which only the aldehyde group in the unsaturated aldehyde is selectively hydrogenated by hydrogen transfer reaction, while the carbon-carbon double bond is left as it is. The method is characterized by using a catalyst which contains at least one oxide selected from the group consisting of oxides of yttrium, lanthanum, praseodymium, neodymium and samarium, as a main active ingredient. The catalysts exhibit high activity and selectivity, as well as a long life span.Type: GrantFiled: August 4, 1993Date of Patent: September 13, 1994Assignee: Mitsubishi Petrochemical Company, Ltd.Inventors: Yoshihisa Watanabe, Mitsuhiko Kurashige
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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