Hydrocarbon Is Aromatic Patents (Class 585/266)
  • Patent number: 5475172
    Abstract: Di-addended and tetra-addended Buckminster fullerenes are synthesized through the use of novel organoborane intermediates. The C.sub.60, C.sub.70, or higher fullerene is reacted with a borane such as BH.sub.3 in a solvent such as toluene to form an organoborane intermediate. Reaction of the organoborane such as hydrolysis with water or alcohol results in the product di-addended and tetra-addended fullerene in up to 30% yields. Dihydrofullerenes and tetrahydrofullerenes are produced by the process of the invention.
    Type: Grant
    Filed: December 1, 1993
    Date of Patent: December 12, 1995
    Assignee: Sandia Corporation
    Inventors: Paul A. Cahill, Craig C. Henderson
  • Patent number: 5472595
    Abstract: A process for treating a charge hydrocarbon oil containing undesired aromatic components, sulfur and nitrogen compounds, which comprisesmaintaining a bed of a sulfided catalyst comprising 0.1 to 15% by weight of nickel; and from 1 to 50% by weight of tungsten and 0.01 to 10% by weight of phosphorus, on an activated carbon support, andpassing a charge hydrocarbon feed in the presence of hydrogen into contact with said catalyst at hydrotreating conditions, thereby effecting hydrodearomatization, hydrodesulfurization and hydrodenitrogenation of said charge hydrocarbon feed containing undesired aromatic components, sulfur and nitrogen, and forming a product stream of hydrocarbon containing a lesser quantity of undesired aromatic components, sulfur and nitrogen; andrecovering said product stream of hydrocarbon containing a lesser quantity of undesired aromatic components, sulfur and nitrogen.
    Type: Grant
    Filed: August 9, 1994
    Date of Patent: December 5, 1995
    Assignee: Texaco Inc.
    Inventors: Chakka Sudhakar, Frank Dolfinger, Jr., Max R. Cesar, Mahendra S. Patel
  • Patent number: 5462651
    Abstract: A process for simultaneous hydrodearomatization, hydrodesulfurization and hydrodenitrogenation of a charge hydrocarbon oil containing undesired aromatic components, sulfur and nitrogen compounds, which comprises:maintaining a bed of a sulfided metal catalyst comprising one or more metals of non-noble Group VIII, at least one metal selected from tungsten and molybdenum on a novel "phosphorus treated carbon" support, the "phosphorus treated carbon" support being comprised of phosphorus bound to the carbon surface predominantly as polyphosphate species characterized by peaks between -5 and -30 ppm in the solid-state magic angle spinning .sup.31 P nuclear magnetic resonance spectrum;passing a charge hydrocarbon feed in the presence of hydrogen into contact with said catalyst at hydrotreating conditions, thereby effecting hydrodearomatization, and simultaneously effecting hydrodesulfurization and hydrodenitrogenation.
    Type: Grant
    Filed: August 9, 1994
    Date of Patent: October 31, 1995
    Assignee: Texaco Inc.
    Inventors: Chakka Sudhakar, Frank Dolfinger, Jr., Max R. Cesar, Mahendra S. Patel, Paul O. Fritz
  • 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: 5457252
    Abstract: A novel catalyst has been provided for the selective hydrogenation of benzene in gasoline. The catalyst mixture comprises a water-soluble, organo-metallic, selective benzene hydrogenation catalyst comprising catalytically-active mixture of (A) M[L].sub.x [X].sub.y wherein M is a metal selected from the group consisting of Cr, Fe, Co, Ni, Mo, Ru, Rh, Pd, Ta, W, Re, Os, Ir, Pt, La and Ce; L is an aromatic hydrocarbon, e.g., benzene, diphenyl, etc., or a diaromatic hydrocarbon, e.g., naphthalene; X is a halogen; x is an integer from 1 to 10 inclusive; and y is an integer from 1 to 10 inclusive; and (B) tris(triphenylphosphine)rhodium(I)halide or tris(triphenylphosphine)ruthenium(I)halide. In use the process comprises admixing the gasoline with water. The above-identified water-soluble, organo-metallic selective benzene hydrogenation catalyst mixture is then added. A catalytic hydrogenation is then carried out in a hydrogenation zone at a temperature of about 150.degree. to about 245.degree. C.
    Type: Grant
    Filed: September 2, 1993
    Date of Patent: October 10, 1995
    Assignee: Her Majesty the Queen in right of Canada, as represented by the Minister of Energy, Mines & Resources
    Inventors: Udai S. Gill, Craig W. Fairbridge, Brian A. Farnand, Esteban C. Castellanos
  • Patent number: 5453552
    Abstract: An advantageous integration of benzene saturation for a light paraffin containing feedstock in a light paraffin isomerization and adsorption system maintains isomerization conversion while reducing benzene levels. The process improves the efficiency of the isomerization and saturation zones by saturating benzene from a light paraffin containing stream and adsorbing normal hydrocarbons from the saturation zone effluent stream together with normal hydrocarbons from an isomerization zone effluent. The isomerization zone effluent comprises converted hydrocarbons from a light paraffin containing feedstream having a relatively low benzene concentration.
    Type: Grant
    Filed: August 20, 1993
    Date of Patent: September 26, 1995
    Assignee: UOP
    Inventors: Lynn H. Rice, Robert S. Haizmann, Mark S. Turowicz
  • Patent number: 5451312
    Abstract: This invention provides a process for producing a distillate boiling-range hydrocarbon product which comprises hydrotreating a hydrodesulfurized aromatic, substantially dealkylated hydrocarbon feed produced by the catalytic cracking of a hydrocarbon fraction, the feed having an initial boiling point of at least 300.degree. F., an aromatic content of at least about 30 weight percent, a hydrogen content not more than about 12 weight percent and a sulfur content of not more than 5000 ppmw, in the presence of a catalyst comprising an inorganic, non-layered, porous, crystalline phase material having pores with diameters of at least about 13 .ANG. and exhibiting, after calcination, an X-ray diffraction pattern with at least one peak with a relative intensity of 100 at a d-spacing greater than about 18 .ANG.
    Type: Grant
    Filed: October 26, 1993
    Date of Patent: September 19, 1995
    Assignee: Mobil Oil Corporation
    Inventors: Minas R. Apelian, Thomas F. Degnan, Stuart S. Shih
  • Patent number: 5449847
    Abstract: There is provided a process for preparing tercyclohexane by reacting benzene with hydrogen. The process involves the use of a catalyst comprising an acidic solid and a hydrogenation component. The acidic solid may comprise a Group IVB metal oxide, such as zirconia, modified with an oxyanion of a Group VIB metal, such as tungsten. The hydrogenation component may comprise platinum.
    Type: Grant
    Filed: April 18, 1994
    Date of Patent: September 12, 1995
    Assignee: Mobil Oil Corporation
    Inventors: Clarence D. Chang, Scott Han, John D. Lutner, Jose G. Santiesteban
  • Patent number: 5449452
    Abstract: A naphtha or a middle distillate hydrocarbon is hydrodearomatized by hydrotreating in the presence of a catalyst containing boron, non-noble Group VIII metal, and Group VIB metal on a carbon support.
    Type: Grant
    Filed: September 20, 1993
    Date of Patent: September 12, 1995
    Inventors: Chakka Sudhakar, Frank Dolfinger, Jr., Max R. Cesar, Jeffrey G. Weissman
  • Patent number: 5442119
    Abstract: A catalytic asymmetric reduction process, which, by hydrogenating trisubstituted olefins, yields a corresponding organic compound having a high level of enantiomeric purity is disclosed. The reduction process utilizes a chiral metal catalyst that includes a metal or metal complex that is selected from groups 3, 4, 5, or 6, lanthanides and actinides. Moreover, the process uses hydrogen as the stoichiometric reducing agent and may be carried out at pressures ranging from about 1 to 200 atmospheres.
    Type: Grant
    Filed: July 12, 1993
    Date of Patent: August 15, 1995
    Assignee: Massachusetts Institute of Technology
    Inventors: Stephen L. Buchwald, Richard D. Broene
  • Patent number: 5435907
    Abstract: A naphtha or a middle distillate hydrocarbon is dehydroaromatized by hydrotreating in the presence of a catalyst containing non-noble Group VIII metal and Group VI-B metal on carbon.
    Type: Grant
    Filed: January 31, 1994
    Date of Patent: July 25, 1995
    Assignee: Texaco Inc.
    Inventors: Chakka Sudhakar, Frank Dolfinger, Jr., Dennis J. Pao, John Hazen
  • Patent number: 5420371
    Abstract: A process is described for carrying out the dehydrogenation or hydrogenation, including hydrogenolysis, of a hydrocarbon in the presence of one or more soluble fullerene catalysts which have been dissolved in the hydrocarbon (when the hydrocarbon is a liquid capable of dissolving the fullerene catalyst) or dissolved in a solvent which is also a solvent for the hydrocarbon (when the hydrocarbon either is not a liquid or is not a liquid which is a solvent for the fullerene catalyst). The use of a liquid catalyst, i.e., a dissolved fullerene catalyst, inhibits coking reactions to thereby inhibit formation of coke on a solid catalyst or catalyst support by elimination of nucleation points or growth regions for such coke formation.
    Type: Grant
    Filed: March 18, 1994
    Date of Patent: May 30, 1995
    Assignee: SRI International
    Inventors: Ripudaman Malhotra, Doris S. Tse, Donald F. McMillen
  • Patent number: 5384059
    Abstract: Mixtures consisting essentially of cyclohexylbiphenyls, dicyclohexylbenzenes, phenylbicyclohexyls and tercyclohexyls are outstandingly suitable as heat transfer media. The mixtures can be prepared from biphenyl and cyclohexanol in the presence of bleaching earths and subsequent hydrogenation.
    Type: Grant
    Filed: August 20, 1993
    Date of Patent: January 24, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Alfons Klein, Rudolf Kron, Helmut Fiege, Klaus-Christian Paetz
  • Patent number: 5350425
    Abstract: A process for reducing vat dyes, such as indigo, into their leuco form by placing a metal, such as aluminum, in water in the presence of a reduction facilitator to form a first solution after which a vat dye having the general structure O.dbd.C(--C.dbd.C--).sub.N C.dbd.O where N=1, 2 or 4 is mixed with the first solution to form a dye solution where substantially all of the vat dye is reduced to its soluble leuco form having the general structure HO--C.dbd.(C--C).sub.N .dbd.C--OH. The process includes dyeing fabric in the dye solution. the reduction facilitator may be a base, for example that produced hydroxide ions in water, and the first solution as well as the dye solution can be a basic solution. The soluble leuco can be isolated from the dye solution and dissolved in a non-aqueous solution. Prior to mixing the vat dye in water, it may first be dissolved in a solvent miscible with water.
    Type: Grant
    Filed: August 9, 1993
    Date of Patent: September 27, 1994
    Inventor: David R. Carver
  • Patent number: 5346612
    Abstract: A process and catalyst are provided for the hydrogenation of a hydrocarbon feedstock consisting essentially of hydrocarbon boiling between about 150.degree. F. and 700.degree. F. at atmospheric pressure. The process comprises reacting the feedstock with hydrogen at hydrogenation conditions in the presence of a catalyst comprising hydrogenation metals and a support comprising beta zeolite. The hydrogenation metals comprise from about 0.1 percent by weight to about 2.0 percent by weight each of palladium and platinum measured as a percentage of the catalyst. The beta zeolite comprises from about 1 ppm by weight to about 3.0 percent by weight sodium calculated as a percentage of said beta zeolite.
    Type: Grant
    Filed: February 19, 1993
    Date of Patent: September 13, 1994
    Assignee: Amoco Corporation
    Inventors: Simon G. Kukes, Frederick T. Clark, P. Donald Hopkins
  • Patent number: 5334790
    Abstract: This is a catalyst and a process for partially hydrogenating polycyclic and monocyclic aromatic hydrocarbons such as benzene, naphthalenes, biphenyls, and alkylbenzenes to produce the corresponding cycloolefins. The catalyst is a hydrogenation catalyst comprising ruthenium on a composite support. It is a process in which the product cycloolefin is produced in high yield and with high selectivity.
    Type: Grant
    Filed: February 26, 1992
    Date of Patent: August 2, 1994
    Assignee: Catalytica
    Inventors: Michael A. Richard, Jacques De Deken, David K. Yee
  • 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: 5273686
    Abstract: Organic-solvent soluble magnesium hydrides or formulas ##STR1## are prepared by catalytically hydrogenating finely powdered magnesium, optionally in the presence of a magnesium halide, in an organic solvent in the presence of their MgH.sub.2 -free counterparts in whichQ is an alkyl, alkenyl, alkoxy, dialkylamino, aralkyl, aryl or diarylamino group, each with up to 18 carbon atoms,R is an alkenyl, aralkyl or aryl group, each with up to 18 carbon atoms,X is chlorine, bromine, or iodine, ##STR2## is a chelating ligand, E is --CH.sub.2, --N(R)-- or --O--,is an alkylene radical of the formula --(CH.sub.2).sub.p,D is a dialkylamino, diarylamino or alkoxy group, each with up to 18 carbon atoms,M is aluminum or boron,m is 1, 2, or 3, and1<n.ltoreq.50.
    Type: Grant
    Filed: August 28, 1991
    Date of Patent: December 28, 1993
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Borislav Bogdanovic, Manfred Schwickardi
  • Patent number: 5264641
    Abstract: There is provided a method for hydrogenating aromatics with a catalyst comprising a crystalline ultra-large pore oxide material. The catalyst also comprises a hydrogenation metal, such as palladium. The process may be used to saturate benzene to form cyclohexane.
    Type: Grant
    Filed: December 14, 1992
    Date of Patent: November 23, 1993
    Assignee: Mobil Oil Corp.
    Inventors: William S. Borghard, Cynthia T. Chu, Thomas F. Degnan, Stuart S. Shih
  • Patent number: 5254763
    Abstract: A novel process is provided for the selective hydrogenation of benzene in a solution of gasoline and other aromatic organic compounds. The process includes the steps of carrying out the catalytic hydrogenation in a hydrogenation zone at a temperature of about 45.degree. to about 250.degree. C. at a pressure of about 200 psi to about 500 psi in a biphasic system of aqueous and organic liquids the hydrogenation catalyst being water-soluble. The organic liquid is removed from the hydrogenation zone. At least a catalytic amount of the catalyst is retained in the hydrogenation zone. The catalyst above described is also a facet of this invention.
    Type: Grant
    Filed: December 2, 1991
    Date of Patent: October 19, 1993
    Inventors: Udai S. Gill, Craig W. Fairbridge, Brian A. Farnand
  • Patent number: 5245093
    Abstract: A process for reacting a fluid phase (gaseous and/or liquid phase) in contact with a solid phase in a reaction zone, wherein the improvement in said process comprises reacting the fluid phase in contact with the solid phase in a horizontally-oriented fluidized bed vessel. The vessel includes at least two compartments or stages, and includes means for vibrating the vessel. The process of the present invention enables one to effect fluidization of the solid phase independently of the flow rate or velocity of the fluid phase, thus enabling proper contact time of the fluid phase with the solid phase and minimizing the amount of fluid phase reactant to be recycled.
    Type: Grant
    Filed: January 26, 1989
    Date of Patent: September 14, 1993
    Assignee: ABB Lummus Crest Inc.
    Inventor: George Ember
  • Patent number: 5197823
    Abstract: A method and apparatus for treating polychlorinated biphenyl (PCB) contaminated soil includes providing a contaminated soil having PCBs therein and treating the soil with elemental zinc powder. The elemental zinc powder reacts with the PCBs in the contaminated soil to at least partially dechlorinate the PCB component of the soil. Also provide are means for treating the PCB contaminated soil including grinding means for achieving a preferred size range for the soil and mixing means to provide intimate contact between the contaminated soil and elemental zinc powder. The method may be practice in-situ such that the PCB contaminated soil is treated at a soil site containing the PCB contaminants.
    Type: Grant
    Filed: August 10, 1992
    Date of Patent: March 30, 1993
    Assignee: Reynolds Metals Company
    Inventors: Eule R. Cutshall, Gregory Felling, Sheila D. Scott, Gary S. Tittle
  • 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: 5171910
    Abstract: The present invention provides a catalyst for hydrogenation of aromatic compounds, which comprises a hydrophilic support material; and a stationary aqueous acid phase supported by the hydrophilic support material, the aqueous acid having a transition metal catalyst dissolved therein, Preferably, the solid hydrophilic support material is an acidic material, such as an acid-treated clay.The foregoing catalyst is particularly useful in hydrogenating aromatic hydrocarbons.
    Type: Grant
    Filed: October 11, 1991
    Date of Patent: December 15, 1992
    Assignee: Exxon Research and Engineering Company
    Inventors: Istvan T. Horvath, Raymond A. Cook
  • Patent number: 5157179
    Abstract: A method for producing a cycloolefin which comprises partially hydrogenating an aromatic hydrocarbon with hydrogen in a liquid phase in the presence of water and a catalyst having as main component ruthenium supported on a carrier, to form the corresponding cycloolefin, wherein an oxide with the total pore volume of pores having radii of from 20 to 100,000 .ANG. being from 0.3 to 10 cc/g and with the volume of pores having radii of from 20 to 200 .ANG. constituting at most 15% of the total pore volume, is used as the carrier for the catalyst.
    Type: Grant
    Filed: July 5, 1991
    Date of Patent: October 20, 1992
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Tohru Setoyama, Takahiko Takewaki, Takao Maki
  • Patent number: 5095160
    Abstract: Benzene is converted to toluene in the presence of free hydrogen and a supported nickel metal catalyst.
    Type: Grant
    Filed: June 24, 1991
    Date of Patent: March 10, 1992
    Assignee: Phillips Petroleum Company
    Inventors: Filippo Penella, Marvin M. Johnson
  • 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: 4973785
    Abstract: Crystalline molecular sieves having three-dimensional microporous framework structures of ELO.sub.2, AlO.sub.2, SiO.sub.2 and PO.sub.2 framework oxide units are disclosed. The molecular sieves have an empirical chemical composition on an anhydrous basis expressed by the formula:mR: (EL.sub.w Al.sub.x P.sub.y Si.sub.z)O.sub.2wherein "R" represents at least one organic templating agent present in the intracrystalline pore system; "m" represents the molar amount of "R" present per mole of (EL.sub.w Al.sub.x P.sub.y Si.sub.z)O.sub.2 ; "EL" represents at least one element capable of forming a framework oxide unit; and "w", "x", "y" and "z" represent the mole fractions of element(s) "EL", aluminum, phosphorus and silicon, respectively, present as framework oxides. Their use as adsorbents, catalysts, etc. is also disclosed.
    Type: Grant
    Filed: April 18, 1988
    Date of Patent: November 27, 1990
    Assignee: UOP
    Inventors: Brent M. T. Lok, Bonita K. Marcus, Lawrence D. Vail, Edith M. Flanigen, Robert L. Patton, Stephen T. Wilson
  • 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: 4931165
    Abstract: A catalytic hydrocracking process which comprises: (a) contacting a hydrocarbonaceous feedstock having a propensity to form heavy polynuclear aromatic compounds and a liquid recycle stream in a hydrocracking zone to convert a substantial portion of the hydrocarbonaceous components in the feedstock to lower boiling products; (b) recovering a hydrocarbon effluent from the hydrocracking zone and partially condensing the hydrocarbon effluent from the hydrocracking zone and separating the same into a lower boiling hydrocarbon product stream and an unconverted hydrocarbon stream having at least a portion boiling above about 400.degree. F. (204.degree. C.
    Type: Grant
    Filed: May 4, 1989
    Date of Patent: June 5, 1990
    Assignee: UOP
    Inventor: Tom N. Kalnes
  • Patent number: 4910356
    Abstract: Compositions containing sulfuric acid and one or more of certain chalcogen-containing compounds in which the chalcogen compound/H.sub.2 SO.sub.4 molar ratio is below 2 contain the mono-adduct of sulfuric acid which is catalytically active for promoting organic chemical reactions. Suitable chalcogen-containing compounds have the empirical formula ##STR1## wherein X is a chalcogen, each of R.sub.1 and R.sub.2 is independently selected from hydrogen, NR.sub.3 R.sub.4, and NR.sub.5, at least one of R.sub.1 and R.sub.2 is other than hydrogen, each of R.sub.3 and R.sub.4 is hydrogen or a monovalent organic radical, and R.sub.5 is a divalent organic radical. Such compositions are useful for catalyzing organic reactions such as oxidation, oxidative addition, reduction, reductive addition, esterification, transesterification, hydrogenation, isomerication (including racemization of optical isomers), alkylation, polymerization, demetallization of organometallics, nitration, Friedel-Crafts reactions, and hydrolysis.
    Type: Grant
    Filed: January 29, 1988
    Date of Patent: March 20, 1990
    Assignee: Union Oil Company of California
    Inventor: Donald C. Young
  • Patent number: 4882038
    Abstract: Crystalline molecular sieves having a three-dimensional microporous framework structures of MgO.sub.2, AlO.sub.2, SiO.sub.2 and PO.sub.2 tetrahedral units are disclosed. These molecular sieves have an empirical chemical composition on an anhydrous basis expressed by the formula:mR: (Mg.sub.w Al.sub.x P.sub.y Si.sub.z)O.sub.2wherein "R" represents at least one organic templating agent present in the intracrystalline pore system; "m" represents the molar amount of "R" present per mole of (Mg.sub.w Al.sub.x P.sub.y Si.sub.z)O.sub.2 ; and "w", "x", "y" and "z" represent the mole fractions of magnesium, aluminum, phosphorus and silicon, respectively, present as tetrahedral oxides. Their use as adsorbents, catalysts, etc. is disclosed.
    Type: Grant
    Filed: February 16, 1988
    Date of Patent: November 21, 1989
    Assignee: UOP
    Inventors: Brent M. T. Lok, Lawrence D. Vail, Edith M. Flanigen
  • Patent number: 4869805
    Abstract: Titanium-aluminum-silicon-oxide molecular sieves are disclosed having use as molecular sieves and as catalyst compositions in hydrocarbon conversion and other processes. The molecular sieves have a unit empirical formula on an anhydrous basis ofmR: (Ti.sub.x Al.sub.y Si.sub.z)O.sub.2wherein "R" represents at least one organic+emplating agent; "m" represents the moles of "R" present per mole of (Ti.sub.x Al.sub.y Si.sub.z)O.sub.2 ; and "x", "y" and "z" represent the mole fractions of titanium, aluminum and silicon, respectively, present as tetrahedral oxides.
    Type: Grant
    Filed: July 22, 1988
    Date of Patent: September 26, 1989
    Assignee: UOP
    Inventors: Brent M. T. Lok, Bonita K. Marcus, Edith M. Flanigen
  • Patent number: 4849093
    Abstract: In the catalytic processing of aromatic hydrocarbon compounds, a hydrocarbon oil is successively contacted at aromatic saturation conditions with a catalyst in a first reaction zone and contacted at a lower temperature with a second portion of the catalyst in the same reactor or in multiple reactors.
    Type: Grant
    Filed: February 2, 1987
    Date of Patent: July 18, 1989
    Assignee: Union Oil Company of California
    Inventors: Dennis A. Vauk, Milan Skripek
  • Patent number: 4795840
    Abstract: The present invention provides a method for preparing a hydrocarbon mixture solvent comprising 1 to 15 wt % of alkyl tetralins and 0 to 10 wt % of aromatic hydrocarbons and having a boiling point of 160.degree. to 300.degree. C., the solvent being substantially free from naphthalene and biphenyl; the method being characterized by comprising the steps of subjecting a kerosene fraction having a boiling point of 150.degree. to 300.degree. C. to a nucleus hydrogenation treatment at a temperature of 100.degree. to 300.degree. C. at a pressure of 30 to 100 kg/cm.sup.2 in the presence of a metallic catalyst for nucleus hydrogenation of aromatic nuclei; separating and removing at least a part of n-paraffins in the kerosene therefrom by the use of a molecular sieve made from a synthesized zeolite having pores of 5 .ANG. in diameter in order to obtain a residual oil; and subjecting the latter to a rectification.
    Type: Grant
    Filed: July 2, 1987
    Date of Patent: January 3, 1989
    Assignee: Nippon Petrochemicals Co., Ltd.
    Inventors: Michiaki Torii, Seiji Hirooka
  • Patent number: 4783565
    Abstract: A cis-isomer of perhydroacenaphthene is selectively prepared through hydrogenation of acenaphthene by effecting hydrogenation of 80.degree. to 200.degree. C. in the presence of a Ru and/or Rh based catalyst. A cis-isomer having the highest boiling point is obtained as a major product.
    Type: Grant
    Filed: May 4, 1987
    Date of Patent: November 8, 1988
    Assignee: Kawasaki Steel Corporation
    Inventors: Yoshihiro Naruse, Toshihide Suzuki
  • Patent number: 4734534
    Abstract: Novel alumina-supported nickel boride catalysts prepared by the borohydride promoted reduction of nickel arsenate are described. Method of catalyst preparation and process for hydrogenation of acetylenic and diolefinic compounds employing the invention catalysts are also described.
    Type: Grant
    Filed: February 5, 1986
    Date of Patent: March 29, 1988
    Assignee: Phillips Petroleum Company
    Inventor: Ted H. Cymbaluk
  • Patent number: 4734536
    Abstract: A process for producing a cycloolefin in high selectivity and yield by partial hydrogenation of a monocyclic armoatic hydrocarbon with hydrogen is disclosed. In this process, the hydrogenation reaction is carried out under a neutral or acidic condition in the presence of:(i) a particulate hydrogenating catalyst mainly comprising metallic ruthenium having an average crystallite size of 200 .ANG. or less,(ii) at least one zinc compound as a promoter,(iii) at least one additive selected from the group consisting of oxides, hydroxides and hydrates thereof Zr, Hf, Ti, Nb, Ta, Cr, Fe, Co, Al, Ga and Si, and(iv) water.
    Type: Grant
    Filed: October 2, 1986
    Date of Patent: March 29, 1988
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Hajime Nagahara, Mitsuo Konishi
  • Patent number: 4696733
    Abstract: A process is disclosed for hydrogenating or partially hydrogenating polynuclear aromatics by contacting them with manganese nodules in the presence of hydrogen at elevated temperatures. The resulting partially hydrogenated products are useful as hydrogen donors in processes such as thermal cracking.
    Type: Grant
    Filed: September 17, 1984
    Date of Patent: September 29, 1987
    Assignee: Mobil Oil Corporation
    Inventor: Ying-Yen P. Tsao
  • Patent number: 4678861
    Abstract: A process for producing a cycloolefin which comprises partially hydrogenating a monocyclic aromatic hydrocarbon in the presence of a ruthenium catalyst composed of a rare earth element compound solid carrier and a ruthenium component supported thereon. The resulting cycloolefin is obtained in high yield and high selectivity and the catalyst can be repeatedly used for a prolonged period of time.
    Type: Grant
    Filed: October 23, 1985
    Date of Patent: July 7, 1987
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Osamu Mitsui, Yohei Fukuoka
  • Patent number: 4665274
    Abstract: A method for producing cycloolefins, useful as an intermediate for lysine, caprolactam, adipic acid etc., by the partial hydrogenation of corresponding aromatic hydrocarbons with a hydrogen gas in the presence of water and a catalyst comprising barium sulfate as a carrier and ruthenium and one or more metals selected from the group consisting of iron, cobalt, silver and copper supported on the carrier, characterized by incorporating one or more metal oxides selected from the group consisting of silicon dioxide, titanium dioxide and aluminum oxide in the reaction system.
    Type: Grant
    Filed: August 27, 1986
    Date of Patent: May 12, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroshi Ichihashi, Hiroshi Yoshioka
  • Patent number: 4645849
    Abstract: A method for hydrogenating olefins and alkynes is provided wherein the unsaturated hydrocarbon is reacted under mild conditions in the presence of a cyclometallated transition metal catalyst which shows greater resistance to degradation caused by oxidation.
    Type: Grant
    Filed: January 22, 1985
    Date of Patent: February 24, 1987
    Assignee: General Electric Company
    Inventor: Larry N. Lewis
  • 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: 4610779
    Abstract: A process for the hydrogenation of aromatic hydrocarbons contained in hydrocarbonaceous oil feed comprising at least about 15 wppm organic nitrogen compounds is provided in which the feed is contacted with hydrogen in a substantially sulfur-free environment in the presence of a catalyst comprising a Group VIII noble metal component, such as palladium, a Y-type crystalline aluminosilicate zeolite and a support such as alumina. When the hydrogenation activity of the catalyst decreases, the partially deactivated catalyst is stripped with hydrogen periodically to increase the hydrogenation activity of the catalyst.
    Type: Grant
    Filed: October 5, 1984
    Date of Patent: September 9, 1986
    Assignee: Exxon Research and Engineering Co.
    Inventors: Gerald E. Markley, James C. Spry, Jr.
  • Patent number: 4605490
    Abstract: A noble metal-containing zeolitic catalyst having cracking activity and hydrogenation activity is pretreated by contacting the catalyst with a nitrogen-containing compound to decrease the cracking activity of the catalyst followed by treatment with hydrogen to recover the hydrogenation activity of the catalyst. The pretreated catalyst is used in a process for the hydrogenation of aromatic hydrocarbons.
    Type: Grant
    Filed: October 5, 1984
    Date of Patent: August 12, 1986
    Assignee: Exxon Research and Engineering Co.
    Inventors: George J. Balinsky, Omer Biceroglu, Joe S. Lin
  • Patent number: 4575572
    Abstract: A method for producing cycloolefins useful as an intermediate material for lysine, caprolactam, adipic acid, medicines, agricultural chemicals, dyes and the like, which comprises partial hydrogenation of aromatic hydrocarbons with hydrogen gas in the presence of a catalyst composed of barium sulfate which is a carrier as well as ruthenium and at least one metal selected from the group consisting of iron, cobalt, silver and copper supported on said barium sulfate, and water.
    Type: Grant
    Filed: July 11, 1985
    Date of Patent: March 11, 1986
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroshi Ichihashi, Hiroshi Yoshioka
  • Patent number: 4560816
    Abstract: Titanium-iron alloys, conditioned or activated to be reversible hydride formers, function as catalysts to promote gas phase hydrogenation and, dehydrogenation reactions. In the hydride form in the presence of hydrogen, the alloys catalyze hydrogenation of C.tbd.C, C.dbd.C, C.tbd.O, C.dbd.O, C.dbd.N, C.tbd.N, N.dbd.O, N.dbd.N and N.tbd.N bonds. Of particular utility is the synthesis of ammonia from a hydrogen-nitrogen mixture at relatively low temperature and pressure. In the unhydrided or metallic form the alloys dehydrogenate C--C, C.dbd.C, C--H and C--N bonds where hydrogen is attached to these groups. Of particular utility is the dehydrogenation of ethane to form ethylene at relatively low temperature and where increased pressure increases the percentage of ethane converted to ethylene.
    Type: Grant
    Filed: October 27, 1983
    Date of Patent: December 24, 1985
    Assignee: University of South Carolina
    Inventor: Milton W. Davis, Jr.
  • Patent number: 4533760
    Abstract: Olefins are produced by contacting an organic compound having at least one benzene ring with calcium metal, ethylenediamine, a low molecular weight aliphatic alcohol, and optionally a low molecular weight aliphatic primary amine, and/or an inert, abrasive particulate substance. The reduction is conducted at temperatures ranging from about -10.degree. C. to about 30.degree. C. or somewhat higher. Substantially all of the organic compounds are converted to corresponding cyclic olefins, primarily diolefins.
    Type: Grant
    Filed: August 23, 1984
    Date of Patent: August 6, 1985
    Assignee: Purdue Research Foundation
    Inventors: Robert A. Benkeser, James A. Laugal, Angela Rappa
  • Patent number: 4533752
    Abstract: Olefins are produced by containing an organic compound having at least one benzene ring with ethylenediamine and calcium metal, the calcium metal being used in large excess or alternatively in conjunction with an inert abrasive particulate substance. Substantially all of the organic compounds are converted to corresponding cyclic olefins, largely mono-olefins.
    Type: Grant
    Filed: August 23, 1984
    Date of Patent: August 6, 1985
    Assignee: Purdue Research Foundation
    Inventors: Robert A. Benkeser, James A. Laugal, Angela Rappa
  • Patent number: 4469590
    Abstract: A process for the hydrogenation of aromatic hydrocarbons contained in a hydrocarbonaceous oil feed is provided in which the feed is contacted with hydrogen in a substantially sulfur-free environment in the presence of a catalyst comprising a Group VIII noble metal component, such as palladium, deposited on a steamed support such as steamed tungsten oxide composited with alumina.
    Type: Grant
    Filed: June 17, 1983
    Date of Patent: September 4, 1984
    Assignee: Exxon Research and Engineering Co.
    Inventors: Robert C. Schucker, Kenneth S. Wheelock