Catalyst Utilized Patents (Class 568/881)
  • Patent number: 5345004
    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 producing 1,3-butylene glycol having high quality (e.g. an odorless, so-called "cosmetic grade") at a high-yield.
    Type: Grant
    Filed: December 8, 1993
    Date of Patent: September 6, 1994
    Assignee: Daicel Chemical Industries, Ltd.
    Inventor: Kazuhisa Nishiguchi
  • Patent number: 5306848
    Abstract: The hydrogenation steps and hydrofinishing steps of the cobalt catalyst oxo process for the preparation of alcohols by the hydroformylation of olefin are carried out using a trimetallic catalyst composed of metal oxides, particularly nickel oxide, molybdenum oxide and cobalt oxide supported on alumina or an alumina-silica in sulfided and non-sulfided form.
    Type: Grant
    Filed: October 16, 1992
    Date of Patent: April 26, 1994
    Assignee: Exxon Chemical Patents Inc.
    Inventor: Jose M. Vargas
  • Patent number: 5300708
    Abstract: A process for the catalytic hydrogenation of organic compounds in the gas phase. The reaction product-containing circulating gas leaving the hydrogenation reactor is compressed without prior cooling, and is then used to heat the starting materials in a superheater to the reaction temperature. The circulating gas stream is further cooled in a hot-gas heat exchanger by cold reactants in a counter-current manner; as a result, substantially all the reaction product condenses out leaving recycle gas. After addition of fresh gas and starting material, the recycle gas is returned via a purification column to the hydrogenation reactor.
    Type: Grant
    Filed: June 23, 1993
    Date of Patent: April 5, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Hofs, Thomas Muller
  • Patent number: 5258558
    Abstract: Solid solutions of magnesium oxide-aluminum oxide related to hydrotalcite and what previously has been referred to as synthetic hydrotalcites, have been prepared with a surface area in excess of 250 m.sup.2 /g, especially at low Mg/Al atom ratios. Such high surface area materials are found to be quite effective in the aldol condensation of aldehydes, and in particular in the conversion of n-butyraldehyde to 2-ethyl-2-hexenal in high yield and with good selectivity in a liquid phase reaction at temperatures under about 200.degree. C.
    Type: Grant
    Filed: May 18, 1992
    Date of Patent: November 2, 1993
    Assignee: UOP
    Inventors: Blaise J. Arena, Jennifer S. Holmgren
  • Patent number: 5254758
    Abstract: In a hydrogenation process, an organic feedstock, such as an unsaturated organic compound containing at least one unsaturated linkage selected from >C.dbd.C<, >C.dbd.O, --C.tbd.C--, and --C.tbd.
    Type: Grant
    Filed: February 12, 1992
    Date of Patent: October 19, 1993
    Assignee: Davy McKee (London) Limited
    Inventors: Andrew G. Hiles, Michael W. M. Tuck
  • Patent number: 5243095
    Abstract: 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: Grant
    Filed: April 24, 1992
    Date of Patent: September 7, 1993
    Assignee: Engelhard Corporation
    Inventors: Brian D. Roberts, Deepak S. Thakur, Thomas J. Sullivan, Robert A. Plundo
  • Patent number: 5227544
    Abstract: The present invention provides a process for producing 2-ethylhexanol having a reduced concentration of 2-ethyl-4-methyl pentanol. It may be practiced in its most basic form as a distillation. It may also be practiced as part of a multi-stage continuous process. In either form it begins with a feed stream comprising n-butyraldehyde containing as a contaminant, isobutyraldehyde, complexes of isobutyraldehyde, oligomers of isobutyraldehyde and mixtures thereof, to which is added or introduced, an amount of water effective to hydrolyze the oligomeric contaminants to the monomeric form of isobutyraldehyde during distillation. The water containing aldehyde mixture is introduced to a distillation zone with a residence time and at a temperature sufficient to hydrolyze the oligomeric contaminants to and then distill substantially all of the isobutyraldehyde overhead.
    Type: Grant
    Filed: July 17, 1992
    Date of Patent: July 13, 1993
    Assignee: BASF Corporation
    Inventors: Laurance R. Thurman, James B. Harris
  • Patent number: 5220020
    Abstract: 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: Grant
    Filed: November 14, 1991
    Date of Patent: June 15, 1993
    Assignee: Massachusetts Institute of Technology
    Inventors: Stephen L. Buchwald, Alberto Gutierrez, Scott C. Berk, Kristina A. Kreutzer
  • Patent number: 5214220
    Abstract: The invention relates to a process for the preparation of an alcohol by hydrogenation of an aldehyde at elevated temperature and superatmospheric pressure in the presence of a homogeneous catalytic system comprising a source of a Group VIII metal compound and a bidentate phosphine.
    Type: Grant
    Filed: August 10, 1992
    Date of Patent: May 25, 1993
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 5210337
    Abstract: 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: Grant
    Filed: March 28, 1990
    Date of Patent: May 11, 1993
    Assignee: Hoechst Celanese Corporation
    Inventor: Jerry A. Broussard
  • Patent number: 5191091
    Abstract: 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: Grant
    Filed: January 27, 1992
    Date of Patent: March 2, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Richard W. Wegman, David R. Bryant
  • Patent number: 5185476
    Abstract: 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: Grant
    Filed: September 26, 1991
    Date of Patent: February 9, 1993
    Assignee: Eastman Kodak Company
    Inventor: Bruce L. Gustafson
  • Patent number: 5185478
    Abstract: Neopentyl glycol is made by reacting isobutyraldehyde with paraformaldehyde in the presence of a tertiary amine and cadmium or yttrium oxide; then hydrogenating the resulting reaction mixture containing hydroxypivaldehyde and at least about 20% 3-hydroxy-2,2-dimethylpropylhydroxypivalate.
    Type: Grant
    Filed: April 16, 1992
    Date of Patent: February 9, 1993
    Assignee: Aristech Chemical Corporation
    Inventors: Jeffrey S. Salek, Joseph Pugach
  • Patent number: 5166349
    Type: Grant
    Filed: June 17, 1991
    Date of Patent: November 24, 1992
    Assignee: The British Petroleum Company, p.l.c.
    Inventor: Stephen G. Davies
  • Patent number: 5146012
    Abstract: Neopentyl glycol is made from isobutyraldehyde and paraformaldehyde; the aldol reaction product is directly mixed with a lower alcohol for hydrogenolysis.
    Type: Grant
    Filed: June 28, 1991
    Date of Patent: September 8, 1992
    Assignee: Aristech Chemical Corporation
    Inventors: Jeffrey S. Salek, Joseph Pugach, Carole L. Elias, Leonard A. Cullo
  • Patent number: 5144088
    Abstract: Neopentyl glycol is made by reacting isobutyraldehyde with paraformaldehyde in the presence of a tertiary amine and one or more oxides of elements of Groups IB, IVA, IVB, VA, VB, VIB and VIII of the periodic table; then hydrogenating the resulting hydroxypivaldehyde-containing product.
    Type: Grant
    Filed: April 26, 1991
    Date of Patent: September 1, 1992
    Assignee: Aristech Chemical Corporation
    Inventors: Jeffrey S. Salek, Joseph Pugach
  • Patent number: 5142067
    Abstract: 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: Grant
    Filed: November 5, 1991
    Date of Patent: August 25, 1992
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Richard W. Wegman, David R. Bryant
  • Patent number: 5096688
    Abstract: A two-stage process for converting synthesis gas to higher alcohols includes an alkali metal-containing cobalt synthesis gas conversion catalyst in a first stage and a copper-containing catalyst in a second stage. The process allows great flexibility in selecting the product mix by changing catalyst compositions and process conditions.
    Type: Grant
    Filed: June 13, 1989
    Date of Patent: March 17, 1992
    Assignee: Amoco Corporation
    Inventors: Jeffrey T. Miller, Cecelia A. Radlowski
  • Patent number: 5093535
    Abstract: A liquid phase catalytic hydrogenation process is described in which an organic feedstock, such as an aldehyde containing from 2 to about 20 carbon atoms, is contracted with hydrogen in the presence of a solid hydrogenation catalyst under hydrogenation conditions to produce a hydrogenation product, such as the corresponding alcohol containing from 2 to about 20 carbon atoms, which process comprises passing a feed solution of the organic feedstock in an inert diluent therefor downwardly in co-current with a hydrogen-containing gas through a hydrogenation zone containing a bed of a particulate hydrogenation catalyst whose particles substantially all lie in the range of from about 1.
    Type: Grant
    Filed: June 4, 1990
    Date of Patent: March 3, 1992
    Assignee: Davy McKee (London) Limited
    Inventors: George E. Harrison, Alan J. Dennis
  • Patent number: 5093534
    Abstract: A process for the preparation of saturated alcohols from aldehydes is disclosed. The hydrogenation of saturated and unsaturated aldehydes to alcohols can be carried out over catalysts containing cooper and nickel. In the present process, the selectivity of the alcohol preparation is further improved by a combination of an alkaline copper catalyst and a nickel-containing catalyst whose carrier material has acidic centers of a certain acid strength H.sub.o.
    Type: Grant
    Filed: June 28, 1991
    Date of Patent: March 3, 1992
    Assignee: Huels Aktiengesellschaft
    Inventors: Gerhard Ludwig, Lothar Fischer, Dieter Hess
  • Patent number: 5081321
    Abstract: Isopropanol is prepared through catalytic hydrogenation of acetone by feeding hydrogen gas and acetone liquid into a reactor having a fixed catalyst bed from its top to form a cocurrent gas/liquid downflow while maintaining the catalyst bed in a trickle bed state. This process can produce isopropanol at a high reaction rate in high yields using a simple reactor.
    Type: Grant
    Filed: January 12, 1990
    Date of Patent: January 14, 1992
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Hiroshi Fukuhara, Fujihisa Matsunaga, Yasunori Shibuta, Toshihiro Tachi
  • Patent number: 5059718
    Abstract: Improved oxo process for preparing higher alcohols by hydrolyzing prior to hydrogenation a demetalled hydroformylation reaction product in the presence of an alumina catalyst having a surface area between 40 to about 60 m.sup.2 /g.
    Type: Grant
    Filed: September 24, 1990
    Date of Patent: October 22, 1991
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Vargas, Jose M., Jean A. Hanin, John C. Reisch
  • Patent number: 5004845
    Abstract: Aliphatic aldehydes are hydrogenated to alcohols containing by product ester which ester is removed and separately hydrogenated to provide additional product.
    Type: Grant
    Filed: June 27, 1988
    Date of Patent: April 2, 1991
    Assignee: Davy McKee (London) Limited
    Inventors: Michael W. Bradley, Norman Harris, Keith Turner
  • Patent number: 4985567
    Abstract: New chiral phosphinopyrrolidine compounds of the general formula: ##STR1## wherein R.sup.1 is hydrogen or --COA.sup.1, --COOA.sup.2, --CONHA.sup.3, --SO.sub.2 A.sup.4 or --PO(A.sup.5).sub.2, A.sup.1, A.sup.2, A.sup.3, A.sup.4 and A.sup.5 each represents independently alkyl or aryl, R.sup.2 is phenyl, di(lower-alkyl)aminophenyl, lower-alkoxyphenyl or 3,5-dimethyl-4-methoxyphenyl, and R.sup.3 is phenyl, lower-alkylphenyl, di(lower-alkyl)aminophenyl, lower-alkoxyphenyl or 3,5-dimethyl-4-methoxyphenyl, with the proviso that R.sup.2 and R.sup.3 may not simultaneously by phenyl, p-di(lower-alkyl)-aminophenyl or p-lower-alkoxyphenyl, as well as the use of these compounds as ligand for a metal complex catalyst for asymmetric synthesis of optically active compounds. The new chiral phosphinopyrrolidine compounds are useful ligands which attain both of high optical yield and high reaction efficiency in catalytic asymmetric reduction.
    Type: Grant
    Filed: March 6, 1989
    Date of Patent: January 15, 1991
    Assignees: Kazuo Achiwa, Fuji Yakuhin Kogyo Kabushiki Kaisha
    Inventors: Kazuo Achiwa, Hideo Takeda
  • Patent number: 4968849
    Abstract: A process for preparing 2-ethylhexanol by the liquid-phase catalytic hydrogenation of 2-ethylhexenal and a catalyst for preforming this catalytic hydrogenation are disclosed.
    Type: Grant
    Filed: December 2, 1988
    Date of Patent: November 6, 1990
    Assignee: Huels Aktiengesellschaft
    Inventors: Hans-Gerd Lueken, Uwe Tanger, Wilhelm Droste, Gernard Ludwig, Dietmar Gubisch
  • Patent number: 4960960
    Abstract: Hydrogen is supplied first to a last hydrogenation zone, and gases recovered from the last hydrogenation zone are passed to the first hydrogenation zone of a continuous multi-zone liquid phase process for hydrogenating an organic compound to a corresponding hydrogenation product. The organic compound, with a suitable diluent or recycle hydrogenation product, flows successively through the zones beginning with the first and ending with the last hydrogenation zone to undergo hydrogenation with the hydrogenation product being recovered from the last hydrogenation zone.
    Type: Grant
    Filed: October 5, 1988
    Date of Patent: October 2, 1990
    Assignee: Davy McKee (London) Limited
    Inventors: George E. Harrison, John R. Hensman
  • Patent number: 4943667
    Abstract: Phenylethanols of the formula ##STR1## where R is hydrogen, alkyl of from 1 to 4 carbon atoms, alkoxy of from 1 to 4 carbon atoms, fluorine, trifluoromethyl or trifluoromethoxy, are prepared by reacting epoxides of the formula ##STR2## where R is as defined above, in the presence of hydrogen over zeolites and/or phosphates, doped with hydrogenating metal as catalysts, preferably over zeolites of the pentasil type.
    Type: Grant
    Filed: January 13, 1989
    Date of Patent: July 24, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer
  • Patent number: 4943635
    Abstract: Chiral 1,3,2-oxazaborolidines and tetrahydro-1,3,2-oxazaborines are effective catalysts for the borane reduction of prochiral ketones to optically active alcohols.
    Type: Grant
    Filed: July 29, 1988
    Date of Patent: July 24, 1990
    Assignee: President & Fellows of Harvard College
    Inventor: Elias J. Corey
  • Patent number: 4885410
    Abstract: The invention relates to a novel supported catalyst comprising a combination of metals with nickel as component (a), a metal having an atomic number greater than 43 from Groups VIIB and VIII of the Periodic Table as component (b) and rhenium as component (c) in a weight ratio of (a):(b):(c) of about 10-90:0.05-5:0.03-10 and to the use of the catalyst for high pressure hydrogenation reactions, particularly for the hydrogenation of butanediol product containing aldehyde, butynediol and color forming impurities.
    Type: Grant
    Filed: August 17, 1988
    Date of Patent: December 5, 1989
    Assignee: GAF Corporation
    Inventor: Waldo De Thomas
  • Patent number: 4879389
    Abstract: New chiral phosphinopyrrolidine compounds of the general formula: ##STR1## wherein R.sup.1 is a hydrogen atom, --COR, --COOR, --CONHR or --SO.sub.2 --R where R is an alkyl or aryl group, R.sup.2 and R.sup.3 each represents independently an aryl group which may have a substituent or substituents, and R.sup.4 and R.sup.5 each represents independently an aliphatic or cycloaliphatic hydrocarbyl group which may have a substituent or substituents, as well as the use of these compounds as ligand for a metal complex catalyst for asymmetric synthesis of optically active compounds. The new chiral phosphinopyrrolidine compounds are useful ligands which attain both of high optical yield and high reaction efficiency in catalytic asymmetric reduction.
    Type: Grant
    Filed: June 25, 1987
    Date of Patent: November 7, 1989
    Inventor: Kazuo Achiwa
  • Patent number: 4876402
    Abstract: An improved vapor phase catalytic hydrogenation of aldehydes to the corresponding alcohols wherein the improvement comprises employing a copper oxide-zinc oxide catalyst impregnated with a selectivity enhancer selected from the group consisting of an alkali-metal, transition metal and mixtures thereof.
    Type: Grant
    Filed: April 26, 1988
    Date of Patent: October 24, 1989
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventors: John E. Logsdon, Richard A. Loke, Jay S. Merriam, Richard W. Voight
  • Patent number: 4855515
    Abstract: A method for producing neopentyl glycol is described using tertiaryamines as a catalyst for the condensation of isobutyraldehyde and formaldehyde followed by hydrogenation of the resulting reaction mixture using a manganese oxide promoted copper chromite catalyst.
    Type: Grant
    Filed: August 12, 1987
    Date of Patent: August 8, 1989
    Assignee: Eastman Kodak Company
    Inventors: Don L. Morris, Billy W. Palmer, Thomas W. McAninch
  • Patent number: 4837368
    Abstract: Process for the hydrogenation of carbonyl-containing compouds at mild conditions of temperature and pressure to produce alcohols or amines is disclosed, employing catalysts comprising palladium and zinc on an inorganic support. A method for the preparation of these supported catalysts which are useful for the desired reductive conversion is also disclosed.
    Type: Grant
    Filed: February 1, 1988
    Date of Patent: June 6, 1989
    Assignee: Eastman Kodak Company
    Inventors: Bruce L. Gustafson, Paul S. Wehner
  • Patent number: 4762817
    Abstract: An aldehyde hydrogenation catalyst consisting essentially of a mixture of copper and zinc oxide impregnated with a minor selectivity improving amount of a selectvity enhancer comprising the combination of an alkali metal selectivity enhancer selected from the group consisting of sodium, potassium, lithium, cesium, and mixtures thereof and a transition metal selectivity enhancer selected from the group consisting of nickel, cobalt, and mixtures thereof.
    Type: Grant
    Filed: November 3, 1986
    Date of Patent: August 9, 1988
    Assignee: Union Carbide Corporation
    Inventors: John E. Logsdon, Richard A. Loke, Jay S. Merriam, Richard W. Voight
  • Patent number: 4756840
    Abstract: Described is the novel compound genus, the beta-alkylidene phenethyl alcohols of our invention, defined according to the generic structure: ##STR1## (wherein R.sub.1 represents hydrogen or methyl, useful in augmenting or enhancing the aroma of consumable materials including perfumes, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener articles, fabric softener compositions, cosmetic powders and hair preparations).
    Type: Grant
    Filed: September 3, 1987
    Date of Patent: July 12, 1988
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko
  • Patent number: 4731488
    Abstract: A catalyst for vapor-phase hydrogen transfer reaction between a carbonyl compound having an alkenyl or aryl group and a primary or secondary alcohol, said catalyst having a composition represented by the following general formulaMg.sub.a X.sub.b Y.sub.c O.sub.dwherein X represents at least one element selected from the group consisting of boron, aluminum, silicon, phosphorus, titanium, vanadium, iron, yttrium, zirconium, niobium, tin, antimony, lead, bismuth, lanthanum and cerium, Y represents at least one element selected from the group consisting of alkali metals and alkaline earth metals excepting magnesium, O represents oxygen, and a, b, c and d represent the atomic ratios of the individual elements, and when a is 1, b represents a number of 0.01 to 0.5, c represents a number of 0 to 0.5, and d is a number determined by the atomic valences and atomic ratios of the individual elements.
    Type: Grant
    Filed: June 6, 1986
    Date of Patent: March 15, 1988
    Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.
    Inventors: Yuuji Shimasaki, Youichi Hino, Michio Ueshima
  • Patent number: 4728671
    Abstract: The present invention relates to a process for producing alcohols comprising hydrogenating compounds selected from the group consisting of acids, esters and aldehydes under sufficient hydrogen pressure and temperature in the presence of a catalyst comprising a copper chromite first component and a second component consisting essentially of copper deposited on a support.
    Type: Grant
    Filed: April 25, 1985
    Date of Patent: March 1, 1988
    Assignee: Oleofina, S.A.
    Inventor: Herve Hinnekens
  • Patent number: 4709105
    Abstract: Preparation of C.sub.3 - to C.sub.25 -alkanols by catalytic hydrogenation of corresponding crude C.sub.3 - to C.sub.25 -alkanols, as obtained in the cobalt-catalyzed hydroformylation of C.sub.2 - to C.sub.24 -olefins, by partial 80-95% hydrogenation conversion in a first stage using a silica supported nickel and molybdenum oxide catalyst and then completing the conversion in a second stage using a cobalt catalyst containing copper, manganese, molybdenum and,optionally other activating additives. The process is especially adapted to the economic preparation of C.sub.9 -C.sub.11 - and C.sub.13 -C.sub.15 -alkanols which are used to prepare high-grade plasticizer esters.
    Type: Grant
    Filed: November 19, 1986
    Date of Patent: November 24, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Armin V. Grenacher, Max Strohmeyer, Herwig Hoffmann, Heinrich Elliehausen
  • Patent number: 4704480
    Abstract: A novel process is described for the production of aliphatic ketones and an optional consequetive production of the corresponding carbinols. The starting reactants comprise ketones or aldehydes or compounds capable of converting to these in situ, such as alcohols. The reaction takes place in the presence of hydrogen in a selective temperature range, utilizing a catalyst comprising copper oxide.
    Type: Grant
    Filed: August 4, 1986
    Date of Patent: November 3, 1987
    Assignee: Allied Corporation
    Inventors: Fred J. Gefri, Divakaran Masilamani, Andiappan K. S. Murthy
  • Patent number: 4684720
    Abstract: In the preparation of a mixture of .alpha.-D-glucopyranosido-1,6-mannitol and .alpha.-D-glucopyranoside-1,6-sorbitol by catalytically hydrogenating .alpha.-D-glucopyranosido-1,6-fructose in aqueous solution with hydrogen under increased pressure and at elevated temperature, the improvement which comprises effecting the hydrogenation continuously over a fixed bed of support-free shaped pieces of elements of sub-group 8 of the periodic table, which serve as the hydrogenation catalyst. The product can be directly used as a sweetener, without purification. The catalyst life is extremely long.
    Type: Grant
    Filed: January 18, 1985
    Date of Patent: August 4, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Darsow, Wolfgang Biedermann
  • Patent number: 4628129
    Abstract: A process for the preparation of ethylene glycol by the catalytic hydrogenation of at least one of di(lower alkyl) oxalate and lower alkyl glycolate in the presence of a hydrogenation catalyst comprising a carrier, which catalyst is suitable for the hydrogenation of alkyl oxalate and alkyl glycolate to ethylene glycol, wherein the carrier has a leachable iron content not greater than about 0.03%, by weight of the carrier.
    Type: Grant
    Filed: February 4, 1985
    Date of Patent: December 9, 1986
    Assignee: Union Carbide Corporation
    Inventor: William J. Bartley
  • Patent number: 4628128
    Abstract: A process for the preparation of ethylene glycol by the vapor phase catalytic hydrogenation of at least one of di(lower alkyl) oxalate and lower alkyl glycolate in the presence of a hydrogenation catalyst comprising a carrier, which catalyst is suitable for the hydrogenation of alkyl oxalate and alkyl glycolate to ethylene glycol, the improvement lies within the preparation of the catalyst by employment of catalysts comprising carriers having specific ranges of physical parameters, including average pore diameter and pore volume, which parameters are interrelated by a relative activity index.
    Type: Grant
    Filed: February 4, 1985
    Date of Patent: December 9, 1986
    Assignee: Union Carbide Corporation
    Inventor: William J. Bartley
  • Patent number: 4626604
    Abstract: A continuous multi-stage hydrogenation process is described.This is effected in at least three catalytic stages connected in series. All stages up to and including the penultimate stage are operated adiabatically and in the vapor phase. Aldehyde (or other unsaturated organic compound) is fed to all stages up to and including the penultimate stage. The rate of supply of the aldehyde or other unsaturated organic compound to the penultimate stage is controlled in relation to the catalyst volume in the penultimate catalytic stage so that the degree of hydrogenation in that stage is less than 100%. The remaining chemically unsaturated material in the product mixture from the penultimate stage is hydrogenated, after cooling that product mixture, in the final catalytic stage to produce a substantially completely hydrogenated product mixture. In this way the dwell time of the reactants and product(s) at "hot spot" temperatures is minimized, thus reducing byproduct formation.
    Type: Grant
    Filed: September 11, 1985
    Date of Patent: December 2, 1986
    Assignee: Davy McKee (London) Limited
    Inventors: Andrew G. Hiles, John E. Logsdon
  • Patent number: 4613707
    Abstract: The reduction of organic compounds to the corresponding hydroxy compounds which comprises contacting a suitable organic compound selected from the group consisting of organic carboxylic acid compounds, aldehydes and ketones with a reducing agent in the presence of a catalyst comprising at least one member selected from the group consisting of copper aluminum borate and zero valent copper on an aluminum borate support.
    Type: Grant
    Filed: March 11, 1985
    Date of Patent: September 23, 1986
    Assignee: Standard Oil Company (Indiana)
    Inventors: Jay K. Kouba, Alex Zletz
  • Patent number: 4599453
    Abstract: A process for the single-stage production in the liquid or gaseous phase, of higher aliphatic ketones starting from ketones of lower molecular weight, characterized in that the starting ketones are reacted with carbon monoxide in the presence of a catalyst in the form of cooper supported on a metal oxide.The catalyst is prepared by depositing on the metal oxide the product obtained from hydrolyzing a cuprammonium solution, then calcining the solid system obtained in air and reducing the calcined product by means of hydrogen.
    Type: Grant
    Filed: February 25, 1985
    Date of Patent: July 8, 1986
    Assignee: Consiglio Nazionale Delle Ricerche
    Inventors: Carlo Fragale, Michele Gargano, Michele Rossi
  • Patent number: 4598058
    Abstract: Molded catalyst materials contain metallic cobalt and/or nickel particles and a lubricant, the said particles being obtained by reduction of cobalt oxide and/or nickel oxide particles containing less than 0.1% by weight of alkali metal oxides and/or alkaline earth metal oxides at .ltoreq.500.degree. C., and the molded catalyst material having an indentation hardness greater than 300 kp/cm.sup.2.
    Type: Grant
    Filed: January 31, 1985
    Date of Patent: July 1, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Frank, Gerald Neubauer, Paul Duffner, Hans J. Wilfinger
  • Patent number: 4568780
    Abstract: This invention relates to the manufacture of ethylene glycol and more particularly to a low pressure process for making ethylene glycol comprising reacting synthesis gas, i.e. a mixture of carbon monoxide and hydrogen, plus 1,3-dioxolane in the presence of a homogenous liquid catalyst containing an effective amount of cobalt-containing compound and a silane or germane-containing promoter dispersed in a hydrocarbon solvent at a temperature of at least 50.degree. C. and a pressure of at least 500 psi, where the particular solvents used allow the desired product to be separated from the reaction mixture by phase separation.
    Type: Grant
    Filed: October 22, 1984
    Date of Patent: February 4, 1986
    Assignee: Texaco Inc.
    Inventor: John F. Knifton
  • Patent number: 4565896
    Abstract: This invention relates to the manufacture of ethylene glcyol and more particularly to a low pressure process for making ethylene glycol comprising reacting synthesis gas, i.e. a mixture of carbon monoxide and hydrogen, plus formaldehyde in the presence of a homogeneous liquid catalyst containing an effective amount of cobalt-containing compound and a silicon or germanium-containing promoter and a solvent at a temperature of at least 50.degree. C. and a pressure of at least 500 psi wherein said ethylene glycol product separates as a separate liquid phase from the solvent.
    Type: Grant
    Filed: October 22, 1984
    Date of Patent: January 21, 1986
    Assignee: Texaco Inc.
    Inventors: John F. Knifton, Roger G. Duranleau
  • Patent number: 4536347
    Abstract: Ruthenium-on-charcoal and ruthenium-on-carbon black catalysts, containing from 0.1 to 5% by weight of iron, for the preparation of olefinically unsaturated alcohols by selective hydrogenation of the corresponding .alpha., .beta.-unsaturated carbonyl compounds in the liquid phase are prepared by modifying the catalyst with iron only after it has been impregnated with the ruthenium compound, and reducing the catalyst with hydrogen at from 400.degree. to 600.degree. C., with thorough mixing.The catalysts according to the invention are particularly useful for improving the industrially difficult hydrogenation of citral to give the soughtafter fragrances geraniol and nerol.
    Type: Grant
    Filed: March 19, 1984
    Date of Patent: August 20, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Horner, Matthias Irgang
  • Patent number: 4532351
    Abstract: Supported catalysts comprised of one or more metals of Group VIII, optionally one or more metals from Group IB and IIA, aluminum and silicate are used for hydrogenating hydrogenatable organic compounds. The catalysts can be produced by coprecipitating metal ions from Group VIII, optionally metal ions from Groups IB and IIA, aluminum ions, and silicate ions, in the presence of solid porous particles.
    Type: Grant
    Filed: June 16, 1982
    Date of Patent: July 30, 1985
    Assignee: Exxon Research and Engineering Co.
    Inventors: Allan E. Barnett, Albert P. Halluin