Patents Assigned to Sun Company, Inc (R&M)
  • Patent number: 5861536
    Abstract: The present invention comprises a process for catalytic oxidative ammination of aromatic hydrocarbons which comprising contacting aromatic feedstock with oxidant, such as molecular oxygen, under suitable reaction conditions, in the presence of a catalyst comprising three essential components: a support; transition metal; and a mono- or binucleating ligand. In one embodiment of the invention the ligand comprises at least one nitro or nitroso group. In another embodiment, the ligand comprises a multidentate, chelating binuclear compound. The process is particularly suited, for example, to the one-step conversion of benzene to aniline.
    Type: Grant
    Filed: July 31, 1997
    Date of Patent: January 19, 1999
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Vincent A. Durante, Tilak P. Wijesekera, Swati Karmakar
  • Patent number: 5817881
    Abstract: Alkanes are catalytically oxidized in air or oxygen using iron-substituted polyoxoanions (POAs) of the formula:H.sub.e-z ?(n-C.sub.4 H.sub.9).sub.4 N!.sub.z (XM.sub.11 M'O.sub.39).sup.-eThe M' (e.g., iron(III)/iron(II)) reduction potential of the POAs is affected by selection of the central atom X and the framework metal M, and by the number of tetrabutyl-ammonium groups. Decreased Fe(III)/Fe(II) reduction potential has been found to correlate to increased oxidation activity.
    Type: Grant
    Filed: July 30, 1997
    Date of Patent: October 6, 1998
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Paul E. Ellis, James E. Lyons, Harry K. Myers, Jr., Shahid N. Shaikh
  • Patent number: 5780383
    Abstract: The invention is a solid catalyst having acid strength H.sub.o less than -18. Such catalysts are characterized by the ability to react with very weak bases, such as butane, at relatively low temperatures, for example temperatures in the range from 20.degree. to 200.degree. C. The catalysts have exceptionally high activity for various hydrocarbon conversion processes, for example, because of their exceptionally high acid strength.
    Type: Grant
    Filed: December 10, 1992
    Date of Patent: July 14, 1998
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Elmer J. Hollstein, James T. Wei, Chao-Yang Hsu
  • Patent number: 5770728
    Abstract: Transition metal complexes of meso-haloalkylporphyrins, wherein the haloalkyl groups contain 2 to 8 carbon atoms have been found to be highly effective catalysts for oxidation of alkanes and for the decomposition of hydroperoxides.
    Type: Grant
    Filed: December 19, 1996
    Date of Patent: June 23, 1998
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Tilak Wijesekera, James E. Lyons, Paul E. Ellis, Jr., Manoj V. Bhinde
  • Patent number: 5767272
    Abstract: Transition metal complexes of meso-haloalkylporphyrins, wherein the haloalkyl groups contain 2 to 8 carbon atoms have been found to be highly effective catalysts for oxidation of alkanes and for the decomposition of hydroperoxides. Also disclosed is a process for the preparation of meso-halocarbyl-porphyrins which comprises contacting a halocarbyl dipyrromethane with a halocarbyl-substituted aldehyde in the presence of an acid granular solid catalyst. Also disclosed is a process for the preparation of meso-halocarbyl-porphyrins which comprises contacting a halocarbyl dipyrromethane with a halocarbyl-substituted aldehyde in the presence of an acid granular solic catalyst.
    Type: Grant
    Filed: December 19, 1996
    Date of Patent: June 16, 1998
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Tilak Wijesekera, James E. Lyons, Paul E. Ellis, Jr., Manoj V. Bhinde
  • Patent number: 5733518
    Abstract: The invention comprises a process for selectively oxidizing hydrogen in a mixture with other gaseous materials by contacting the hydrogen containing gas under oxidation conditions with a catalyst comprising a phosphate of a metal wherein the metal is selected from the group consisting of germanium, tin, lead, arsenic, antimony and bismuth.
    Type: Grant
    Filed: July 10, 1996
    Date of Patent: March 31, 1998
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Vincent A. Durante, Daniel E. Resasco, Darrell W. Walker, Gary L. Haller, Eugene L. Coggins
  • Patent number: 5723677
    Abstract: The invention comprises a method for the oxidation of alkanes to alcohols and for decomposition of hydroperoxides to alcohols utilizing new compositions of matter, which are metal complexes of porphyrins. Preferred complexes have hydrogen, haloalkyl or haloaryl groups in meso positions, two of the opposed meso atoms or groups being hydrogen or haloaryl, and two of the opposed meso atoms or groups being hydrogen or haloalkyl, but not all four of the meso atoms or groups being hydrogen. Other preferred complexes are ones in which all four of the meso positions are substituted with haloalkyl groups and the beta positions are substituted with halogen atoms. A new method of synthesizing porphyrinogens is also disclosed.
    Type: Grant
    Filed: June 27, 1996
    Date of Patent: March 3, 1998
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Tilak Wijesekera, James E. Lyons, Paul E. Ellis, Jr.
  • Patent number: 5723697
    Abstract: The presence of a base in the reaction mixture in a metal-ligand catalyzed partial oxidation of alkanes results in sustained catalyst activity, and in greater percent conversion as compared with oxidation in the absence of base, while maintaining satisfactory selectivity for the desired oxidation, for example the oxidation of isobutane to isobutanol.
    Type: Grant
    Filed: December 29, 1995
    Date of Patent: March 3, 1998
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Manoj V. Bhinde, Thomas W. Bierl
  • Patent number: 5705685
    Abstract: Alkanes are converted to unsaturated carboxylic acids by contacting an alkane with an oxidizing agent and a heteropolyacid or polyoxoanion comprising (1) at least 9 atoms of a first framework metal or metals comprising molybdenum, tungsten or vanadium or combinations thereof and (2) 1 to 3 atoms of a second framework metal or metals comprising zinc or a transition metal different from the first framework metal.
    Type: Grant
    Filed: October 31, 1995
    Date of Patent: January 6, 1998
    Assignee: Sun Company, Inc. (R&M)
    Inventors: James E. Lyons, Paul E. Ellis, Jr., Swati Karmakar, Shahid N. Shaikh
  • Patent number: 5672778
    Abstract: The invention comprises a method for the catalytic conversion of alkanes and alkylhydroperoxides to oxygenates, particularly alcohols, comprising the oxidation of alkanes to yield alkylhydroperoxides, alcohols, other reaction products and unreacted alkane, and the decomposition of said alkylhydroperoxides to form alcohols and oxygen. Decomposition of the alkylhydroperoxide in the presence of unreacted alkane increases the yield of alcohol. The process further comprises drying of the reaction mixture comprising alkylhydroperoxide. Suitable catalysts for the process of the invention comprise metal containing catalysts, including metal organic ligand catalysts such as unsubstituted and substituted metal complexes of porphyrins, phthalocyanines and acetylacetonates.
    Type: Grant
    Filed: August 26, 1996
    Date of Patent: September 30, 1997
    Assignee: Sun Company, Inc. (R & M)
    Inventors: James E. Lyons, Paul E. Ellis, Jr., Manoj V. Bhinde
  • Patent number: 5663328
    Abstract: The invention provides novel catalyst compositions, useful in the oxidation of hydrocarbons with air or oxygen to form hydroxy-group containing compounds and in the decomposition of hydroperoxides to form hydroxy-group containing compounds. The catalysts comprise transition metal complexes of a porphyrin ring having 1 to 12 halogen substituents on the porphyrin ring, at least one of said halogens being in a meso position and/or the catalyst containing no aryl group in a meso position. The compositions are prepared by halogenating a transition metal complex of a porphyrin.
    Type: Grant
    Filed: June 27, 1996
    Date of Patent: September 2, 1997
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Paul E. Ellis, Jr., James E. Lyons
  • Patent number: 5659029
    Abstract: A hydroxyl-containing pyrrolic compound having a hydroxyl group or a hydroxyl-containing group in the 2-position, optionally substituted in the beta positions, is condensed in an acidified two immiscible phase solvent system to produce excellent yields of the corresponding porphyrin or metal porphyrin.
    Type: Grant
    Filed: December 22, 1995
    Date of Patent: August 19, 1997
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Paul E. Ellis, Jr., Wayne A. Langdale
  • Patent number: 5648590
    Abstract: Acyclic hydrocarbons having 4 to 7 carbon atoms per molecule are isomerized in the liquid phase by contact with a solid superacid catalyst comprising sulfated oxide or hydroxide of a metal selected from the group consisting of Group III and Group IV metals, to obtain high octane number blending components for motor fuel and/or valuable chemical and fuel intermediates.
    Type: Grant
    Filed: August 17, 1994
    Date of Patent: July 15, 1997
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Chao-Yang Hsu, Vasant K. Patel, David H. Vahlsing, James T. Wei, Harry K. Myers, Jr.
  • Patent number: 5629257
    Abstract: A sulfated solid catalyst is provided which comprises (1) oxide or hydroxide of Group III or Group IV element, e.g. zirconium, and (2) a first metal comprising a metal or combination of metals selected from the group consisting of platinum, palladium, nickel, platinum and rhenium, and platinum and tin. The catalyst may further comprise (3) a second metal selected from the group consisting of Group VIII elements, e.g. iron. One embodiment of the invention further comprises (4) a third metal selected from the group consisting of Group V, VI and VII elements, e.g. manganese. The catalyst of the invention is useful for the isomerization of normal alkanes having 4 to 40 carbon atoms per molecule, for the naphtha upgrading of a hydrocarbon feedstock and for the hydrocracking of a hydrocarbon feedstock.
    Type: Grant
    Filed: January 21, 1994
    Date of Patent: May 13, 1997
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Benjamin S. Umansky, Manoj V. Bhinde, Chao-Yang Hsu, Chen-Shi Huang
  • Patent number: 5608054
    Abstract: Transition metal complexes of meso-haloalkylporphyrins, wherein the haloalkyl groups contain 2 to 8 carbon atoms have been found to be highly effective catalysts for oxidation of alkanes and for the decomposition of hydroperoxides.
    Type: Grant
    Filed: March 17, 1995
    Date of Patent: March 4, 1997
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Tilak Wijesekera, James E. Lyons, Paul E. Ellis, Jr., Manoj V. Bhinde
  • Patent number: 5571908
    Abstract: The invention comprises new compositions of matter, which are iron, manganese, cobalt or ruthenium complexes of porphyrins having hydrogen, haloalkyl or haloaryl groups in meso positions, two of the opposed meso atoms or groups being hydrogen or haloaryl, and two of the opposed meso atoms or groups being hydrogen or haloalkyl, but not all four of the meso atoms or groups being hydrogen. The invention also comprises new compositions of matter in which all four of the meso positions are substituted with haloalkyl groups and the beta positions are substituted with halogen atoms. A new method of synthesizing porphyrinogens is also provided.The novel compositions and others made according to the process of the invention are useful as hydrocarbon conversion catalysts; for example, for the oxidation of alkanes and the decomposition of hydroperoxides.
    Type: Grant
    Filed: December 29, 1993
    Date of Patent: November 5, 1996
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Tilak Wijesekera, James E. Lyons, Paul E. Ellis, Jr.
  • Patent number: 5550301
    Abstract: Organic hydroperoxides are decomposed by drying a reaction mixture containing the organic hydroperoxide and an organic solvent such that said dried reaction mixture comprises approximately 1 weight percent or less of water and contacting the dried reaction mixture with a metal organic ligand catalyst under hydroperoxide decomposition conditions. An organic co-solvent for the hydroperoxide may also be used. Particularly effective catalysts are cobalt acetylacetonates and ruthenium acetylacetonates and combinations thereof.
    Type: Grant
    Filed: March 3, 1995
    Date of Patent: August 27, 1996
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Manoj V. Bhinde, James E. Lyons, Paul E. Ellis, Jr.
  • Patent number: 5540833
    Abstract: New compositions of matter comprise a metal from the group consisting of platinum, rhodium and palladium, a metal from the first row of Group VIII of the Periodic Table and a nonacidic L-zeolite. A preferred composition is Pt--Ni/KL-zeolite. Such catalysts are prepared by coimpregnation of the zeolite with the metals. Methods of using the catalysts in reforming, aromatization or dehydrogenation are provided.
    Type: Grant
    Filed: January 31, 1994
    Date of Patent: July 30, 1996
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Gustavo Larsen, Gary L. Haller, Daniel E. Resasco, Vincent A. Durante
  • Patent number: 5516964
    Abstract: An isomerization process is provided which process utilizes a sulfated solid catalyst comprising (1) oxide or hydroxide of Group III or Group IV element, e.g. zirconium, and (2) a first metal comprising a metal or combination of metals selected from the group consisting of platinum, palladium, nickel, platinum and rhenium, and platinum and tin. The sulfated support is calcined prior to incorporation of the first metal and subsequent to said incorporation. The catalyst may further comprise (3) a second metal selected from the group consisting of Group VIII elements, e.g. iron. One embodiment of the invention further comprises (4) a third metal selected from the group consisting of Group V, VI and VII elements, e.g. manganese. Said second and third metals are added prior to the first calcination.
    Type: Grant
    Filed: January 21, 1994
    Date of Patent: May 14, 1996
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Benjamin S. Umansky, Manoj V. Bhinde, Chao-Yang Hsu
  • Patent number: 5510558
    Abstract: Oxidative dehydrogenation of alkanes and alkylaromatic hydrocarbons is achieved by contact with an active carbon catalyst. In various aspects of the invention, the oxidative dehydrogenation is performed at a pressure above about 100 psia, and/or at a temperature in the range from about 500.degree. C. to about 800.degree. C., and/or the active carbon catalyst contains a metal, for example, molybdenum.
    Type: Grant
    Filed: December 29, 1993
    Date of Patent: April 23, 1996
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Benjamin S. Umansky, Kevin A. Boyer, Chao-Yang Hsu