Catalyst Utilized Patents (Class 568/881)
  • Patent number: 6288288
    Abstract: 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: Grant
    Filed: November 25, 1998
    Date of Patent: September 11, 2001
    Assignee: Celanese GmbH
    Inventor: Helmut Springer
  • Patent number: 6278030
    Abstract: 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: Grant
    Filed: January 14, 2000
    Date of Patent: August 21, 2001
    Assignee: Exxon Chemical Patents, Inc.
    Inventors: Jose Manuel Vargas, Kenneth Lloyd Riley
  • Patent number: 6245952
    Abstract: 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: Grant
    Filed: March 1, 1999
    Date of Patent: June 12, 2001
    Assignee: Firmenich SA
    Inventor: Hubert Mimoun
  • Patent number: 6239318
    Abstract: 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: Grant
    Filed: September 15, 1999
    Date of Patent: May 29, 2001
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Joachim Schuler, Alfred Kaizik, Bernhard Scholz, Wilfried Bueschken, Wilhelm Droste
  • Patent number: 6218585
    Abstract: 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: Grant
    Filed: April 20, 2000
    Date of Patent: April 17, 2001
    Assignee: Mine Safety Appliances Company
    Inventors: Karl Matos, Joseph A. Corella, II, Elizabeth R. Burkhardt, Shawn M. Nettles
  • Patent number: 6211419
    Abstract: 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: Grant
    Filed: April 24, 2000
    Date of Patent: April 3, 2001
    Assignee: The Dow Chemical Company
    Inventors: Gary R. Strickler, Von G. Landon, Guo-Shuh John Lee
  • Patent number: 6207865
    Abstract: 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: Grant
    Filed: January 11, 2000
    Date of Patent: March 27, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Boris Breitscheidel, Marc Walter, Detlef Kratz, Gerhard Schulz, Manfred Sauerwald
  • Patent number: 6191323
    Abstract: 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: Grant
    Filed: April 25, 2000
    Date of Patent: February 20, 2001
    Assignee: UOP LLC
    Inventors: Laszlo T. Nemeth, Avelino Corma Canos, Susana Valencia Valencia, Jaime G. Moscoso, Marcelo Eduardo Domine
  • Patent number: 6156933
    Abstract: 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: Grant
    Filed: February 18, 1999
    Date of Patent: December 5, 2000
    Assignees: Degussa-Huls AG, Thomas Swan & Co. Ltd.
    Inventors: Martyn Poliakoff, Thomas M. Swan, Thomas Tacke, Martin G. Hitzler, Stephen K. Ross, Stefan Wieland
  • Patent number: 6156940
    Abstract: 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: Grant
    Filed: April 8, 1998
    Date of Patent: December 5, 2000
    Assignees: Sumika Fine Chemicals Company, Limited, Sumitomo Chemical Company, Limited
    Inventors: Kenji Saito, Norio Kometani, Azusa Fujiwara, Yukio Yoneyoshi, Gohfu Suzukamo
  • Patent number: 6150567
    Abstract: 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: Grant
    Filed: December 29, 1997
    Date of Patent: November 21, 2000
    Assignee: Kaneka Corporation
    Inventors: Tadashi Sugawa, Tadashi Moroshima, Kenji Inoue, Kazunori Kan
  • Patent number: 6124509
    Abstract: 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: Grant
    Filed: January 22, 1999
    Date of Patent: September 26, 2000
    Assignee: Brookhaven Science Associates
    Inventors: Mark Voges, R. Morris Bullock
  • Patent number: 6096931
    Abstract: 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: Grant
    Filed: December 3, 1998
    Date of Patent: August 1, 2000
    Assignee: Celanese GmbH
    Inventors: Carl Dieter Frohning, Wolfgang Zgorzelski, Hans Liebern
  • Patent number: 6054627
    Abstract: 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: Grant
    Filed: May 27, 1992
    Date of Patent: April 25, 2000
    Assignee: Engelhard Corporation
    Inventors: Deepak S. Thakur, Eugene Palka, Thomas I. Sullivan, Eugene Nebesh, Brian D. Roberts
  • Patent number: 6046127
    Abstract: 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: Grant
    Filed: July 15, 1998
    Date of Patent: April 4, 2000
    Assignee: Firmenich SA
    Inventor: Hubert Mimoun
  • Patent number: 6037505
    Abstract: 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: Grant
    Filed: April 26, 1999
    Date of Patent: March 14, 2000
    Assignee: Pfizer Inc.
    Inventor: George Joseph Quallich
  • Patent number: 6008419
    Abstract: 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: Grant
    Filed: December 19, 1997
    Date of Patent: December 28, 1999
    Assignee: The Dow Chemical Company
    Inventors: P. J. Thomas, R. Garth Pews, Paul C. Vosejpka, George J. Frycek
  • Patent number: 5922921
    Abstract: 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: Grant
    Filed: October 27, 1997
    Date of Patent: July 13, 1999
    Assignee: Celanese International Corporation
    Inventors: Jerry D. Unruh, Debra A. Ryan, Shannon L. Dugan
  • Patent number: 5874649
    Abstract: 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: Grant
    Filed: November 5, 1997
    Date of Patent: February 23, 1999
    Assignee: Kao Corporation
    Inventors: Shigeyoshi Tanaka, Shinji Kotachi, Junji Koshino, Junko Yamamoto
  • Patent number: 5874652
    Abstract: 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: Grant
    Filed: October 18, 1993
    Date of Patent: February 23, 1999
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Rangasamy Pitchai, Thomas S. Zak
  • Patent number: 5866725
    Abstract: 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: Grant
    Filed: December 11, 1997
    Date of Patent: February 2, 1999
    Assignee: Celanese International Corporation
    Inventors: Jerry D. Unruh, Debra A. Ryan, Shannon L. Dugan
  • Patent number: 5852221
    Abstract: 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: Grant
    Filed: April 29, 1997
    Date of Patent: December 22, 1998
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Hiroshi Kashihara, Mikio Suzuki, Yoshio Ohara
  • Patent number: 5831135
    Abstract: 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 step
    Type: Grant
    Filed: October 6, 1997
    Date of Patent: November 3, 1998
    Assignee: Huels Aktiengesellschaft
    Inventors: Wilfried Bueschken, Juergen Hummel
  • Patent number: 5831133
    Abstract: 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: Grant
    Filed: May 15, 1996
    Date of Patent: November 3, 1998
    Assignee: Firmenich SA
    Inventor: Hubert Mimoun
  • Patent number: 5763690
    Abstract: 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: Grant
    Filed: August 2, 1996
    Date of Patent: June 9, 1998
    Assignee: Aristech Chemical Corporation
    Inventors: Jeffrey S. Salek, Joseph Pugach, Carole L. Elias, Leonard A. Cullo
  • Patent number: 5741475
    Abstract: 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: Grant
    Filed: September 30, 1996
    Date of Patent: April 21, 1998
    Assignee: Agency of Industrial Science & Technology
    Inventors: Takumi Takashima, Tadayoshi Tanaka, Takahiro Fujii, Takuya Doi
  • Patent number: 5728891
    Abstract: 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 subseque
    Type: Grant
    Filed: June 26, 1996
    Date of Patent: March 17, 1998
    Assignee: Huels Aktiengesellschaft
    Inventors: Wilfried Bueschken, Juergen Hummel
  • Patent number: 5684215
    Abstract: 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: Grant
    Filed: December 28, 1992
    Date of Patent: November 4, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhardt Horn, Carl Dieter Frohning
  • Patent number: 5675045
    Abstract: 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 step
    Type: Grant
    Filed: June 26, 1996
    Date of Patent: October 7, 1997
    Assignee: Huels Aktiengesellschaft
    Inventors: Wilfried Bueschken, Juergen Hummel
  • Patent number: 5650546
    Abstract: 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: Grant
    Filed: December 16, 1994
    Date of Patent: July 22, 1997
    Assignee: Council of Scientific Industrial Resear.
    Inventors: Raghunath Vitthal Chaudhari, Bhalchandra Mahadeo Bhanage, Sunil Sadashiv Divekar, Raj Madhukar Deshpande
  • Patent number: 5600030
    Abstract: 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: Grant
    Filed: May 9, 1995
    Date of Patent: February 4, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gregor Deckers, Gerhard Diekhaus, Bernd Dorsch, Carl D. Frohning, Gerhardt Horn, Horst B. Horrig
  • Patent number: 5583266
    Abstract: 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: Grant
    Filed: May 2, 1994
    Date of Patent: December 10, 1996
    Assignee: Texaco Inc.
    Inventors: Robert J. Taylor, Jr., Pei-Shing E. Dai, John F. Knifton
  • Patent number: 5583270
    Abstract: 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: Grant
    Filed: June 23, 1994
    Date of Patent: December 10, 1996
    Assignee: Daicel Chemical Industries, Ltd.
    Inventor: Kazuhisa Nishiguchi
  • Patent number: 5569792
    Abstract: 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: Grant
    Filed: March 17, 1995
    Date of Patent: October 29, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gregor Deckers, Gerhardt Horn
  • Patent number: 5552548
    Abstract: 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: Grant
    Filed: October 13, 1994
    Date of Patent: September 3, 1996
    Assignee: Pfizer Inc.
    Inventor: George J. Quallich
  • Patent number: 5550302
    Abstract: 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: Grant
    Filed: March 16, 1995
    Date of Patent: August 27, 1996
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Tomoyuki Mori, Kouichi Fujita, Hiroki Hinoishi
  • Patent number: 5495055
    Abstract: 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: Grant
    Filed: February 13, 1995
    Date of Patent: February 27, 1996
    Assignee: Arco Chemical Technology, L.P.
    Inventor: Michael A. Rueter
  • Patent number: 5495054
    Abstract: 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: Grant
    Filed: May 31, 1994
    Date of Patent: February 27, 1996
    Assignee: Sepracor, Inc.
    Inventors: Yun Gao, Yaping Hong, Charles M. Zepp
  • Patent number: 5491266
    Abstract: 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: Grant
    Filed: June 20, 1994
    Date of Patent: February 13, 1996
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: James E. Babin, Gregory T. Whiteker
  • Patent number: 5476972
    Abstract: 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: Grant
    Filed: January 28, 1994
    Date of Patent: December 19, 1995
    Assignee: Texaco Chemical Inc.
    Inventors: Pei-Shing E. Dai, Robert J. Taylor, Jr., John F. Knifton, Bobby R. Martin
  • Patent number: 5475161
    Abstract: 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: Grant
    Filed: January 17, 1992
    Date of Patent: December 12, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhardt Horn, Carl D. Frohning, Hans Liebern, Wolfgang Zgorzelski
  • Patent number: 5449838
    Abstract: 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: Grant
    Filed: December 30, 1993
    Date of Patent: September 12, 1995
    Assignee: Texaco Chemical Inc.
    Inventors: John F. Knifton, Ernest L. Yeakey, Pei-Shing E. Dai
  • Patent number: 5430198
    Abstract: 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: Grant
    Filed: November 8, 1993
    Date of Patent: July 4, 1995
    Assignee: Texaco Chemical Inc.
    Inventors: John F. Knifton, Pei-Shing E. Dai
  • Patent number: 5406004
    Abstract: 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 compou
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: April 11, 1995
    Assignee: Eastman Chemical Company
    Inventors: Philip H. D. Eastland, John Scarlett, Michael W. M. Tuck, Michael A. Wood
  • Patent number: 5403962
    Abstract: 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: Grant
    Filed: May 31, 1994
    Date of Patent: April 4, 1995
    Assignee: Sud-Chemie AG
    Inventors: Michael Schneider, Karl Kochloefl, Gerd Maletz
  • Patent number: 5399793
    Abstract: 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: Grant
    Filed: November 29, 1993
    Date of Patent: March 21, 1995
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Jose M. Vargas, Magdiel Agosto, Kenneth L. Riley
  • Patent number: 5382716
    Abstract: 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: Grant
    Filed: March 23, 1993
    Date of Patent: January 17, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Bahrmann, Wolfgang Greb, Peter Heymanns, Peter Lappe, Jurgen Szameitat, Thomas Muller, Ernst Wiebus
  • Patent number: 5354915
    Abstract: 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: Grant
    Filed: December 21, 1992
    Date of Patent: October 11, 1994
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Walter T. Reichle
  • Patent number: 5347056
    Abstract: 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: Grant
    Filed: August 4, 1993
    Date of Patent: September 13, 1994
    Assignee: Mitsubishi Petrochemical Company, Ltd.
    Inventors: Yoshihisa Watanabe, Mitsuhiko Kurashige
  • Patent number: 5345005
    Abstract: 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: Grant
    Filed: September 18, 1992
    Date of Patent: September 6, 1994
    Assignee: Engelhard Corporation
    Inventors: Deepak S. Thakur, Brian L. Roberts, Thomas J. Sullivan, Anita L. Vichek