Group Viii Metal With Additional Nonhydrocarbon Agent Or Complexed With Hydrocarbon Patents (Class 585/277)
  • Patent number: 5587348
    Abstract: A catalyst composition comprises palladium, at least one chemically bound alkali metal (preferably potassium), chemically bound fluorine and an inorganic support material (preferably alumina), wherein the atomic ratio of fluorine to alkali metals about 1.3:1 to about 4:1. Preferably, silver is also present in the catalyst composition. The above-described catalyst is employed as a catalyst in the selective hydrogenation of C.sub.2 -C.sub.10 alkynes (preferably acetylene) to the corresponding alkenes in the presence of sulfur impurities.
    Type: Grant
    Filed: April 19, 1995
    Date of Patent: December 24, 1996
    Assignee: Phillips Petroleum Company
    Inventors: Scott H. Brown, Stan A. Zisman, James B. Kimble
  • Patent number: 5583274
    Abstract: C.sub.2 -C.sub.6 alkynes (preferably acetylene) contained in feeds which also contain sulfur impurities are hydrogenated to the corresponding alkenes in the presence of a supported palladium catalyst which has been promoted with alkali metal fluoride (preferably potassium fluoride).
    Type: Grant
    Filed: January 20, 1995
    Date of Patent: December 10, 1996
    Assignee: Phillips Petroleum Company
    Inventors: Tin-Tack P. Cheung, Marvin M. Johnson
  • Patent number: 5569803
    Abstract: A method for producing a cycloolefin, which comprises partially hydrogenating a monocyclic aromatic hydrocarbon in the presence of water and a ruthenium catalyst supported on silica modified by zirconium oxide.
    Type: Grant
    Filed: December 23, 1994
    Date of Patent: October 29, 1996
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Takahiko Takewaki, Naoko Fujita, Toshiharu Yokoyama, Takao Maki
  • Patent number: 5563308
    Abstract: Compounds of formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.8 alkyl, phenyl or phenyl which is substituted by 1 to 3 C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy groups; R.sub.2 and R.sub.3 are each independently of the other typically C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl, phenyl, or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.5 -C.sub.12 cycloalkyl, or phenyl which is substituted by one to three identical or different members selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen;R.sub.10 and R.sub.11 are identical and are typically C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl, C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.5 -C.sub.12 cycloalkyl or phenyl which is substituted by 1 to 3 identical or different members selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen; or R.sub.10 and R.sub.11 are different and are C.sub.1 -C.sub.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: October 8, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Felix Spindler, Amina Wirth-Tijani, Heidi Landert
  • Patent number: 5563309
    Abstract: Compounds of formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.8 alkyl, phenyl or phenyl which is substituted by 1 to 3 C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy groups; R.sub.2 and R.sub.3 are identical and are C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.5 -C.sub.12 cycloalkyl, or phenyl which is substituted by one to three identical or different members selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy,--SiR.sub.4 R.sub.5 R.sub.6, halogen, --SO.sub.3 M,--CO.sub.2 M,--PO.sub.3 M,--NR.sub.7 R.sub.8 and --[.sup..sym. NR.sub.7 R.sub.8 R.sub.9 ]X.sup..crclbar. ; or R.sub.1 and R.sub.3 are different and are C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl, C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.5 -C.sub.12 cycloalkyl, phenyl or phenyl which is substituted by one to three identical or different members selected from the group consisting of C.sub.1 -C.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: October 8, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Antonio Togni, Felix Spindler, Nadia Zanetti, Amina Tijani
  • Patent number: 5545784
    Abstract: Molecular sieves are modified by an ion exchange process where metal cations are introduced into the molecular sieves by means of solid state ion exchange. The solid state ion exchange can be carried out as follows: a weighed amount of calcined and activated zeolite is intimately mixed with a precalculated amount of PtCl.sub.2, PdCl.sub.2, RhCl.sub.3, CuCl.sub.2, V.sub.2 O.sub.5 or another compound of the noble metals (e.g., corresponding halides or oxides), the solids mixture is then heated in a current of inert gas (e.g., a current of helium gas or of nitrogen) to temperatures of 400.degree. to 600.degree. C., then cooled down to room temperature and subsequently reduced in a current of hydrogen for 10 to 14 hours at 280.degree. to 350.degree. C. in order to produce small metal clusters from the cationically introduced metal.
    Type: Grant
    Filed: April 11, 1995
    Date of Patent: August 13, 1996
    Assignee: Degussa Aktiengesellschaft
    Inventors: Jens Weitkamp, Stefan Ernst, Thomas Bock, Thomas Kromminga, Akos Kiss, Peter Kleinschmit
  • Patent number: 5510503
    Abstract: The invention relates to novel enantiomerically pure bisphosphines of the general formula (I) ##STR1## in which R, R.sup.1 and R.sup.2 have the meanings given in the description, a process for the preparation thereof and the use thereof in metal complexes as catalysts for asymmetric hydrogenations.
    Type: Grant
    Filed: September 2, 1994
    Date of Patent: April 23, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Christian Laue, Georg Schroder, Dieter Arlt, Rolf Grosser
  • Patent number: 5498584
    Abstract: Disclosed in a process for the homogeneous, catalytic hydrogenation of epoxyalkenes and epoxycyclo-alkenes, especially conjugated .gamma.,.delta.-epoxyalkenes and epoxycycloalkenes, to the corresponding epoxyalkanes and epoxycycloalkanes using a solution of a complex rhodium catalyst whereby the olefinic unsaturation is hydrogenated without significant hydrogenolysis of the conjugated epoxy group.
    Type: Grant
    Filed: September 23, 1994
    Date of Patent: March 12, 1996
    Assignee: Eastman Chemical Company
    Inventor: Thomas A. Puckette
  • Patent number: 5457251
    Abstract: Disclosed is a method for partially hydrogenating a monocyclic aromatic hydrocarbon to produce a cycloolefin, comprising reacting a monocyclic aromatic hydrocarbon with hydrogen in the presence of a particulate hydrogenation catalyst comprised mainly of metallic ruthenium, in a reaction system comprising a continuous aqueous phase having the particulate hydrogenation catalyst suspended therein, an oil phase containing the monocyclic aromatic hydrocarbon, and a gaseous phase comprising hydrogen gas, while applying a shearing force to the reaction system at a specific maximum shear rate. By the method of the present invention, not only can a cycloolefin be produced at high selectivity and in high yield, but also the catalytic activity can be stably maintained at a high level for a prolonged period of time.
    Type: Grant
    Filed: January 21, 1993
    Date of Patent: October 10, 1995
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Kunihiko Yamashita, Hideaki Obana, Issei Katsuta
  • Patent number: 5417844
    Abstract: The invention relates to a process for the selective hydrogenation of diolefins in steam cracking petrol in the presence of a nickel catalyst and is characterized in that prior to the use of the catalyst, a suphur-containing organic compound is incorporated into the catalyst outside of the reactor.
    Type: Grant
    Filed: November 18, 1992
    Date of Patent: May 23, 1995
    Assignee: Institut Francais du Petrole
    Inventors: Jean-Paul Boitiaux, Patrick Sarrazin
  • Patent number: 5414170
    Abstract: The present invention provides an improved process for selectively hydrogenating acetylenes in an olefin plant process stream by selectively hydrogenating the acetylenes downstream of a front end depropanizer and upstream of further separation zones such as a demethanizer and/or de-ethanizer.
    Type: Grant
    Filed: May 12, 1993
    Date of Patent: May 9, 1995
    Assignee: Stone & Webster Engineering Corporation
    Inventors: Richard H. McCue, Edna B. Hicks
  • Patent number: 5406012
    Abstract: A composition comprising a crystalline aluminumphosphate material having a three-dimensional microporous crystal framework structure whose chemical composition expressed in terms of mole ratios of oxides isAl.sub.2 O.sub.3 : 1.0.+-.0.2 P.sub.2 O.sub.5 ;and which is further defined as having an x-ray powder diffraction pattern characterized by d spacings at less than about 40 degrees two-theta as measured using copper K-alpha radiation that are substantially as shown in the Table and a metal in an amount of up to about 25 percent by weight is disclosed. The composition can be prepared by impregnating the crystalline aluminumphosphate material with the metal in an amount of up to about 25 percent by weight. The resultant heterocatalyst system can be used to shape-selectively hydrogenate an unsaturated organic compound, such as, for example an olefin, aldehyde or ketone.
    Type: Grant
    Filed: May 23, 1989
    Date of Patent: April 11, 1995
    Assignee: The Dow Chemical Company
    Inventor: Mark E. Davis
  • Patent number: 5382729
    Abstract: Compounds of formula I ##STR1## wherein R.sub.1 denotes identical or different radicals and is linear or branched C.sub.1 -C.sub.12 alkyl, unsubstituted C.sub.5 -C.sub.6 cycloalkyl or C.sub.5 -C.sub.6 cycloalkyl which is substituted by C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, or is phenyl or benzyl, or both substituents R.sub.1 of a group (R.sub.1).sub.2 P are o,o-diphenylene, R.sub.2 is hydrogen, linear or branched C.sub.1 -C.sub.12 alkyl, phenyl or benzyl, R.sub.3 is C.sub.1 -C.sub.12 alkylene, R.sub.4 is C.sub.2 -C.sub.18 alkylene, phenylene or benzylene, and R.sub.5 is C.sub.1 -C.sub.6 alkyl or phenyl, can be applied to solid carriers, such as silica gel or aerosils, and complexed with rhodium or iridium compounds. These materials are heterogeneous and separable catalysts for the assymetrical hydrogenation of prochiral compounds containing carbon double bonds or carbon/hetero atom double bonds, for example ketones and imines.
    Type: Grant
    Filed: February 16, 1994
    Date of Patent: January 17, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Benoit Pugin, Felix Spindler, Manfred Muller
  • Patent number: 5378767
    Abstract: A method for hydrogenating unsaturated low molecular weight polymers, preferably polydiene monool, diol and polyol polymers, which comprises contacting the polymers under hydrogenation conditions with hydrogen in the presence of a fixed bed heterogeneous catalyst which is comprised of platinum, palladium or a mixture of the two supported on an alpha alumina support.
    Type: Grant
    Filed: June 18, 1993
    Date of Patent: January 3, 1995
    Assignee: Shell Oil Company
    Inventor: Stephen N. Massie
  • Patent number: 5347027
    Abstract: The present invention provides an electroless process for making a catalyst in a liquid or gaseous medium comprising contacting a base metal with a chemical cleaning agent and simultaneously or sequentially treating said base metal under reducing conditions with a noble metal-containing material, the catalyst prepared using the process, and a method of using the catalyst.
    Type: Grant
    Filed: April 22, 1993
    Date of Patent: September 13, 1994
    Assignee: OSi Specialties, Inc.
    Inventors: James S. Ritscher, Wei T. Yang, George M. Omietanski, Robert L. Ocheltree, Earl E. Malson
  • Patent number: 5334791
    Abstract: A process is provided for hydrogenating a non-aromatic unsaturated hydrocarbon, comprising reacting the hydrocarbon with a catalyst precursor which includes a source of a group VIIIB transition metal from the second or third rows of the periodic table and a heterobifunctional ligand constructed with a phosphine center and an imine nitrogen center, in the presence of hydrogen and a promoter selected from secondary or tertiary acyclic alkyl amines in a suitable solvent which solubilizes the hydrocarbon, the catalyst precursor, the hydrogen, and the promoter.
    Type: Grant
    Filed: May 22, 1992
    Date of Patent: August 2, 1994
    Assignee: Ligands Inc.
    Inventors: Ronald G. Cavell, David J. Law, Robert W. Reed
  • Patent number: 5321176
    Abstract: Hydrogenation of a polyene to a monoene using a ruthenium catalyst that is promoted with water.
    Type: Grant
    Filed: December 22, 1992
    Date of Patent: June 14, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Kathryn M. Sanchez
  • Patent number: 5306853
    Abstract: Compounds of formula II ##STR1## wherein the groups (R.sub.1).sub.2 P(CH.sub.2).sub.m bzw.n are in o- or m-position to each other and the substituents R.sub.1 are identical or different radicals, m and n are each independently of the other 0 or 1, R.sub.1 is linear or branched C.sub.1 -C.sub.12 alkyl, unsubstituted C.sub.5 -C.sub.6 cycloalkyl or C.sub.5 -C.sub.6 cycloalkyl which is substituted by C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, or is phenyl or benzyl, or both substituents R.sub.1 in a group (R.sub.1).sub.2 P together are o,o'-diphenylene, --R.sub.2 --X-- is a bond or --(C.sub.x H.sub.2x --O).sub.y --, or X-- is O-- and R.sub.2 is C.sub.1 -C.sub.6 alkylene, x is an integer from 2 to 6 and y is an integer from 2 to 6, R.sub.3 is C.sub.2 -C.sub.18 alkylene, phenylene or benzylene, and R.sub.4 is C.sub.1 -C.sub.6 alkyl or phenyl, can be applied to solid carriers, such as silica gel or aerosils, and complexed with rhodium or iridium compounds.
    Type: Grant
    Filed: June 17, 1993
    Date of Patent: April 26, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Benoit Pugin, Manfred Muller, Felix Spindler
  • Patent number: 5300716
    Abstract: A process for the preparation of a polyunsaturated olefinic compound, i.e. undeca-1,3,5-triene, in its (3E,5Z) isomeric form, consisting of four consecutive steps starting from deca-1,4-diyne, is disclosed.Said process has the advantage of making it possible to obtain the desired isomer in its essentially pure form.
    Type: Grant
    Filed: September 6, 1991
    Date of Patent: April 5, 1994
    Assignee: Firmenich SA
    Inventor: Christian Chapuis
  • Patent number: 5268521
    Abstract: Disclosed herein is a catalyst for especially for selective hydrogenation among a carbon-carbon double bond, a carbonyl group and an aromatic unsaturated ring such as benzene. The catalyst comprising platinum and zeolite can be employed for selectively hydrogenating the carbon-carbon double bond and the carbonyl group of an organic compound without the hydrogenation of the aromatic unsaturated. The catalyst comprising the platinum supported on a support which comprises powders of an inorganic component to which is supported polyethylene glycol or an ethylvinylbenzene-divinylbenzene copolymer can be employed for selectively hydrogenating the carbon-carbon double bond of an organic compound without the hydrogenation of the carbonyl group and the aromatic unsaturated ring.
    Type: Grant
    Filed: November 22, 1991
    Date of Patent: December 7, 1993
    Assignee: Tanaka Kikinzoku Kogyo K.K.
    Inventors: Kenji Tamaru, Kikuo Shoji, Kazuki Noda
  • Patent number: 5254714
    Abstract: A process is disclosed for the enantioselective hydrogenation of olefins of the formula: ##STR1## where R is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, Z is ##STR2## where R' is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, --CN, C(NH)OR" where R" is C.sub.1 to C.sub.6 linear or branched alkyl, or --C(O)NH.sub.2 ; and Ar is phenyl or naphthyl unsubstituted or substituted with benzoyl or substituted benzoyl, C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched alkoxy, halo, or carboxylic acid or C.sub.1 to C.sub.6 linear or branched alkyl ester thereof, which comprises contacting said aromatic-substituted olefin with a catalytically effective amount of a ruthenium phosphite complex.
    Type: Grant
    Filed: October 10, 1991
    Date of Patent: October 19, 1993
    Assignee: Ethyl Corporation
    Inventor: Merrikh Ramezanian
  • Patent number: 5233110
    Abstract: A process for the preparation of cyclooctene which comprises irradiating 1,5-cyclooctadiene with light in the presence of a photodehydrogenation catalyst, acetone and an alcohol to partially hydrogenate the 1,5-cyclooctadiene.
    Type: Grant
    Filed: February 28, 1992
    Date of Patent: August 3, 1993
    Assignee: Agency of Industrial Science & Technology
    Inventors: Taka-aki Hanaoka, Yoshihiro Sugi, Takehiko Matsuzaki, Kazuhiko Takeuchi, Hironori Arakawa
  • Patent number: 5210349
    Abstract: Cyclic polyenes are selectively hydrogenated to cyclic monoenes under suitable hydrogenation conditions in the presence of an activated ruthenium catalyst complexes. The ruthenium catalyst complex is activated by hydrogenating a minimal amount of cyclic polyene under suitable hydrogenation conditions.
    Type: Grant
    Filed: March 4, 1992
    Date of Patent: May 11, 1993
    Assignee: Phillips Petroleum Company
    Inventors: Michael S. Matson, Harold J. Swindell
  • Patent number: 5210348
    Abstract: A substantially benzene-free product suitable for gasoline blending is formed from a benzene-containing refinery stream. At least about 30% of the benzene initially present in the stream is catalytically alkylated with C.sub.2 -C.sub.4 olefins to form alkylated products. Most preferably, the alkylation zone is present in the distillation column and the alkylated products drop to the lower portion of the column and are recovered with the heavy fraction. Alternatively, the alkylation zone is downstream of the distillation column and a secondary distillation column removes the heavier alkylated products. The remaining light fraction is hydrogenated to convert substantially all of the remaining non-alkylated benzene to cyclohexane and is isomerized to boost the octane of C.sub.5 -C.sub.7 paraffins, preferably in a single reactor.
    Type: Grant
    Filed: May 23, 1991
    Date of Patent: May 11, 1993
    Assignee: Chevron Research and Technology Company
    Inventors: C. Richard Hsieh, Richard C. Robinson
  • Patent number: 5189233
    Abstract: Disclosed is an improvement in a process for production of cyclohexane by liquid phase hydrogenation of benzene wherein no diluent is necessary, which comprises contacting benzene and hydrogen in the presence of a mixed catalyst bed comprising a first catalyst which is a less active hydrogenation catalyst selected from elements of Group VIII of the Periodic Table and a second, more active catalyst, comprising a Group VIII metal supported on an oxide, such as, for example, alumina, silica or titania at a temperature of about 40.degree. C. to about 300.degree. C. and pressure sufficient to keep the benzene liquid at the chosen reaction temperature.
    Type: Grant
    Filed: August 23, 1991
    Date of Patent: February 23, 1993
    Assignee: Texaco Chemical Company
    Inventors: John M. Larkin, James H. Templeton, Donald H. Champion
  • Patent number: 5180870
    Abstract: Hydrogenation of a polyene to a monoene using a ruthenium catalyst that is promoted with a sterically-hindered tertiary amine.
    Type: Grant
    Filed: October 23, 1991
    Date of Patent: January 19, 1993
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Rocco A. Paciello
  • Patent number: 5177278
    Abstract: Partial hydrogenation of 1,5,9-cyclododecatriene to form cyclododecene using ruthenium catalyst and a solvent selected from the group consisting of esters and ethers having a boiling point higher than 245 degrees C.
    Type: Grant
    Filed: October 23, 1991
    Date of Patent: January 5, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Kathryn M. Sanchez
  • Patent number: 5171907
    Abstract: A cobalt carbonyl phosphine complex useful for hydrogenation of cyclic polyenes to corresponding cyclic monoenes is prepared by reaction of dicobalt carbonyl and a phosphine compound in at least one non-oxygenated aliphatic solvent. Selective hydrogenation of the cyclic polyenes comprises an induction period during which the polyenes are contacted with the cobalt carbonyl complex catlayst under hydrogen pressure followed by decreasing the reaction temperature and pressure for a period of time sufficient to complete the hydrogenation.
    Type: Grant
    Filed: July 1, 1991
    Date of Patent: December 15, 1992
    Assignee: Phillips Petroleum Company
    Inventors: Michael S. Matson, Stan A. Zisman
  • Patent number: 5149893
    Abstract: A catalytic hydrogenation process comprising contacting a catalyst effective to promote a hydrogenation reaction with a feed stream comprising gaseous hydrogen and an unsaturated hydrocarbon thereby hydrogenating at least some of said unsaturated hydrocarbon, said catalyst being prepared from a precursor comprising a calcium aluminate cement and at least one oxide of a metal selected from nickel and cobalt by reduction of said metal oxide, and wherein said precursor contains 10 to 70% by weight of said metal oxide (expressed as the divalent oxide, MO) and has a porosity in the range 25 to 50%, in which at least 30% of the pore volume is in the form of pores of size in the range 15 to 35 nm and less than 40% of the pore volume is in the form of pores of diameter greater than 35 nm.
    Type: Grant
    Filed: June 6, 1991
    Date of Patent: September 22, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Frank King, Martin E. Fakley
  • Patent number: 5138111
    Abstract: An eta phase composition in powder form, prepared in the absence of sulfur or sulfur bearing compounds, having a surface area greater than about 2m.sup.2 /g and consisting of X.sub.6 Y.sub.6 Z.sub.a wherein X is at least one element selected from the group consiting of Mo and W, Y is at least one element selected from the group consisting of Fe, Co. Ni, Mo and W, Z is at least one element selected from the group consisting of C, N and combinations thereof such that when Z is N, a is greater than or equal to 1 but less than or equal to 2 and when Z is C, a is greater than 1 but less than or equal to 2 except when Z is C and Y is Fe, then a is greater than or equal to 1 but less than or equal to 2. The eta phase may be a carbide, nitride or carbonitride. A method for producing the eta-phase composition includes providing a precursor compound including at least two eta-phase forming metals, and a ligand containing carbon, nitrogen or combinations thereof.
    Type: Grant
    Filed: September 16, 1991
    Date of Patent: August 11, 1992
    Assignee: Exxon Research and Engineering Company
    Inventors: Edwin L. Kugler, Larry E. McCandlish, Allan J. Jacobson, Russell R. Chianelli
  • Patent number: 5132270
    Abstract: Deactivated hydrogenation catalysts of ruthenium metal deposited on an aluminum oxide support are regenerated by treatment with ultrasound.
    Type: Grant
    Filed: July 5, 1991
    Date of Patent: July 21, 1992
    Assignee: Huels Aktiengesellschaft
    Inventors: Gerhard Wachholz, Gerhard Thelen, Heinz-Werner Voges
  • Patent number: 5118837
    Abstract: A modified ruthenium catalyst can be used to selectively hydrogenate an olefinic double bond in the presence of another olefinic double bond in the same or in a different molecule. Modifiers are selected from compounds containing trivalent nitrogen, trivalent phosphorus and divalent sulfur.
    Type: Grant
    Filed: February 12, 1987
    Date of Patent: June 2, 1992
    Assignee: Givaudan Corporation
    Inventors: Alan J. Chalk, Laszlo V. Wertheimer
  • Patent number: 5081083
    Abstract: Alternate, successive high temperature oxidation and reduction treatments, in either order, of intermetallic alloy hydrogenation and intermetallic alloy oxidation catalysts unexpectedly improves the impurity poisoning resistance, regeneration capacity and/or activity of the catalysts. The particular alloy, and the final high temperature treatment given alloy (oxidation or reduction) will be chosen to correspond to the function of the catalyst (oxidation or hydrogenation).
    Type: Grant
    Filed: February 12, 1990
    Date of Patent: January 14, 1992
    Assignee: The United States of America as represented by the Secretary of the Department of Energy
    Inventor: Randy B. Wright
  • Patent number: 5072069
    Abstract: The invention relates to cycloolefinic complexes of platinum, processes for preparing the same from platinum(II) compounds and cyclolefins having at least 12 ring carbon atoms and at least two aliphatic non-cumulated carbon-carbon double bonds and their use as a catalyst for the addition of Si-bonded hydrogen to an aliphatic multiple bond.
    Type: Grant
    Filed: February 27, 1990
    Date of Patent: December 10, 1991
    Assignee: Consortium Fur Elektrochemische Ind.
    Inventors: Guido Wenski, Ludwig Maier, Hans-Jurgen Eberle
  • Patent number: 5030779
    Abstract: A hydrogenation catalyst prepared by combining one or more Group VIII metal compounds with one or more alkylalumoxanes and one or more alkyls or hydrides of a metal selected from the group consisting of the Group Ia, IIa, and IIa metals and a hyrogenation process wherein said catalyst is used to hydrogenate compounds containing ethylenic and/or aromatic unsaturation. Preferably, the one or more Group VIII metal compounds will be contacted sequentially with the one or more alkylalumoxanes and the one or more alkyls or hydrides, first with the one or more alkylalumoxanes and then with one or more alkyls and/or hydrides. The one or more Group VIII metal compounds is selected from the group of compounds consisting of carboxylates, chelates, alkoxides, salts of acids containing sulfur, salts of partial esters of acids containing sulfur and salts of aliphatic and aromatic sulfonic acids. Nickel and cobalt compounds are preferred for use in the hydrogenation catalysts.
    Type: Grant
    Filed: August 29, 1990
    Date of Patent: July 9, 1991
    Assignee: Shell Oil Company
    Inventors: Ronald J. Hoxmeier, Lynn H. Slaugh
  • Patent number: 4995963
    Abstract: A crystalline, galliosilicate molecular sieve having the zeolite L type structure and the following composition expressed in terms of oxide mole ratios in the anhydrous state:Ga.sub.2 O.sub.3 :xSiO.sub.2 :yM.sub.2 O:zK.sub.2 Owhere M is an alkali metal other than potassium, preferably sodium, x equals at least 3.0, preferably 4 to 10, y equals 0 to 0.9, z equals 0.1 to 1.0, and y+z equals about 1.0. The crystalline, galliosilicate molecular sieve of the invention may be employed, after reducing its alkali metal content, as a component of a catalyst which can be used in a variety of chemical conversion processes, preferably hydrocarbon conversion processes, and most preferably hydrocracking and isomerization processes.
    Type: Grant
    Filed: January 16, 1990
    Date of Patent: February 26, 1991
    Assignee: Union Oil Company of California
    Inventor: Mario L. Occelli
  • Patent number: 4990710
    Abstract: Group VIII metal modified non-acidic tin containing microporous crystalline materials which in catalysis exhibit high selectively for dehydrogenation and dehydrocyclization are described.
    Type: Grant
    Filed: June 24, 1988
    Date of Patent: February 5, 1991
    Assignee: Mobil Oil Corporation
    Inventors: Ralph M. Dessau, Ernest W. Valyocsik, James C. Vartuli
  • 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: 4982028
    Abstract: Non-acid microporous crystalline indium containing materials are combined with Group VIII metal such as platinum to produce catalysts which exhibit high selectivity for dehydrocyclization of C.sub.5.sup.+ paraffins and which exhibit little, if any, cracking activity for hexane and heptane.
    Type: Grant
    Filed: September 5, 1989
    Date of Patent: January 1, 1991
    Assignee: Mobil Oil Corporation
    Inventors: Ralph M. Dessau, Ernest W. Valyocsik
  • Patent number: 4980331
    Abstract: A hydrogenation catalyst prepared by combining one or more Group VIII metal compounds with one or more alkylalumoxanes and one or more alkyls or hydrides of a metal selected from the group consisting of the Group Ia, IIa, and IIa metals and a hydrogenation process wherein said catalyst is used to hydrogenate compounds containing ethylenic and/or aromatic unsaturation. Preferably, the one or more Group VIII metal compounds will be contacted sequentially with the one or more alkylalumoxanes and the one or more alkyls or hydrides, first with the one or more alkylalumoxanes and then with the one or more alkyls and/or hydrides. The one or more Group VIII metal compounds is selected from the group of compounds consisting of carboxylates, chelates, alkoxides, salts of acids containing sulfur, salts of partial esters of acids containing sulfur and salts of aliphatic and aromatic sulfonic acids. Nickel and cobalt compounds are preferred for use in the hydrogenation catalysts.
    Type: Grant
    Filed: June 8, 1989
    Date of Patent: December 25, 1990
    Assignee: Shell Oil Company
    Inventors: Ronald J. Hoxmeier, Lynn H. Slaugh
  • Patent number: 4967031
    Abstract: A process for the non-catalytic hydrogenation of organic compounds, which contain at least one reducible functional group, which comprises reacting the organic compound, a hydride complex, preferably a transition metal hydride complex or an organosilane, and a strong acid in a liquid phase.
    Type: Grant
    Filed: December 13, 1989
    Date of Patent: October 30, 1990
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventor: R. Morris Bullock
  • Patent number: 4950386
    Abstract: It has now been discovered that hydrocarbon feeds containing a polycyclic aromatic compound or mixtures thereof can be selectively hydrogenated by contacting the feed with a transition metal catalyst and hydrogen in the presence of an acid to provide a hydrocarbon mixture in which the aromatic content consists substantially of mono- and di-aromatic compounds. Useful acids include Lewis acids and acids having a pKa in the range of 0 to about -10.
    Type: Grant
    Filed: August 15, 1988
    Date of Patent: August 21, 1990
    Assignee: Exxon Research and Engineering Company
    Inventor: Manuel A. Francisco
  • Patent number: 4950820
    Abstract: Olefinic hydrocarbons present in mixtures containing tert.-alkyl alkyl ethers and, if appropriate, other saturated aliphatic or aromatic hydrocarbons can be hydrogenated with substantial preservation of the ethers if the catalyst used has an active component for hydrogenation on a catalyst support having a specific surface area of more than 50 m.sup.2 /g and a pore diameter of, in the main, <1,000 nm.
    Type: Grant
    Filed: July 14, 1986
    Date of Patent: August 21, 1990
    Assignee: EC Erdolchemie GmbH
    Inventors: Bernhard Schleppinghoff, Horst Reinhardt, Hans-Joachim Kramer
  • Patent number: 4895994
    Abstract: Catalysts made by the Raney process (e.g., Raney process nickel) pelletized in matrix of polymer and plasticizer are activated by either (a) removal of plasticizer (e.g., by solvent extraction) followed by leaching out Al with caustic solution, leaving an active catalyst made by the Raney process in a polymer matrix; or (b) removal of plasticizer, then calcining to remove polymer, followed by leaching with caustic. The activated catalyst pellets have sufficient strength and attrition resistance for efficient use in fixed beds and packed columns for superior hydrogenation of toluene, heptene, butyraldehyde, and other conventional feedstockers used with catalysts made by the Raney process.
    Type: Grant
    Filed: October 18, 1988
    Date of Patent: January 23, 1990
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Wu-Cheng Cheng, Christian B. Lundsager, Robert M. Spotnitz
  • 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: 4874504
    Abstract: A method is disclosed which provides improved control over the noble-metal exchange of zeolite catalyst by using bulky organic bases to control pH during the metal loading step.
    Type: Grant
    Filed: March 20, 1989
    Date of Patent: October 17, 1989
    Assignee: Mobil Oil Corporation
    Inventors: Roland von Ballmoos, Francis X. Ryan
  • Patent number: 4804796
    Abstract: Improved, heterogeneous, refractory catalysts are in the form of gas-impervious, hollow, thin-walled spheres (10) suitable formed of a shell (12) of refractory such as alumina having a cavity (14) containing a gas at a pressure greater than atmospheric pressure. The wall material may be itself catalytic or a catalytically active material coated onto the sphere as a layer (16), suitably platinum or iron, which may be further coated with a layer (18) of activator or promoter. The density of the spheres (30) can be uniformly controlled to a preselected value within .+-.10 percent of the density of the fluid reactant such that the spheres either remain suspended or slowly fall or rise through the liquid reactant.
    Type: Grant
    Filed: April 8, 1987
    Date of Patent: February 14, 1989
    Assignee: California Institute of Technology
    Inventors: Taylor G. Wang, Daniel D. Elleman, Mark C. Lee, James M. Kendall, Jr.
  • Patent number: 4792625
    Abstract: The invention provides a process for reducing substantially water insoluble organic compounds containing reducible groups comprising contacting these compounds with an aqueous solution of a formic acid salt in the presence of a hydrogenation catalyst and in the substantial absence of a phase transfer catalyst.
    Type: Grant
    Filed: July 9, 1987
    Date of Patent: December 20, 1988
    Assignee: Yissum Research Development Company
    Inventors: Harold Wiener, Shmuel Vandel, Yoel Sasson
  • Patent number: 4755627
    Abstract: Diisopropenylbenzene is a monomer that can be used in the preparation of many useful polymers and is also a chemical intermediate that can be employed in a number of chemical processes. Diisopropenylbenzene is normally synthesized by the dehydrogenation of diisopropylbenzene. Unfortunately in this dehydrogenation process a number of olefinic impurities are produced as by-products. This invention discloses a process for the separation of diisopropenylbenzene from these impurities and for recycling some of the impurities.
    Type: Grant
    Filed: November 24, 1986
    Date of Patent: July 5, 1988
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Howard A. Colvin, Ronald D. Fiedler, Joel Muse, Jr., Donald E. Smith
  • Patent number: 4751344
    Abstract: Saturated hydrocarbon is transformed catalytically into olefinic hydrocarbon of corresponding skeletal configuration by reacting the saturated hydrocarbon with a suitable alkene cyclopentadienyl or alkene arene transition metal molecular complex, such as bis(ethylene)pentamethylcyclopentadienyliridium, bis(ethylene)pentamethylcyclopentadienylrhodium and bis(ethylene)hexamethylbenzene osmium in the presence of free alkene as hydrogen acceptor. The reaction may be performed photochemically under irradiation with ultraviolet light or it may be performed thermolytically under application of heat. The catalyst may be charged to the reaction as a preformed alkene cyclopentadienyl or alkene arene transition metal molecular complex or the catalyst may be formed in situ in the reaction mixture via displacement of ligand from a suitable transition metal complex containing the displaceable ligand, such as dicarbonylpentamethylcyclopentadienyliridium or cyclooctadienepentamethylcyclopentadienyliridium.
    Type: Grant
    Filed: April 16, 1987
    Date of Patent: June 14, 1988
    Assignee: Ethyl Corporation
    Inventor: Howard W. Walker