By Isomerization Patents (Class 585/477)
  • Patent number: 4620054
    Abstract: This invention relates to acid catalysis of organic compound feedstock, e.g. isomerization of xylenes, over catalyst material treated in a special way for increasing the acid catalytic activity thereof. In particular, a novel catalyst activation process is followed to enhance the alpha value of high-silica zeolite catalyst by contact with an ammoniacal solution of an alkali metal aluminate under appropriate conditions of time, temperature and pH.
    Type: Grant
    Filed: October 15, 1985
    Date of Patent: October 28, 1986
    Assignee: Mobil Oil Corporation
    Inventors: Clarence D. Chang, Joseph N. Miale
  • Patent number: 4547606
    Abstract: Resorcinol is prepared in high yield and purity by an improved process through superacid (such as perfluorinated alkanesulfonic acids of one to eighteen carbon atoms or polymeric perfluorinated resinsulfonic acids, such as acidified Nafion-H, catalyzed cleavage rearrangement reaction of meta-bis(2-hydroperoxy-2-propyl)benzene (meta-diisopropylbenzene dihydroperoxide). Part of the process is the preparation of needed meta-diisopropylbenzene in high purity (98-100%) substantially free of other isomers by treating any mixture of diisopropylbenzenes with an excess of anhydrous hydrogen fluoride or a perfluorinated alkanesulfonic acid of one to eighteen carbon atoms and a Lewis acid fluoride, or by alkylating (transalkylating) cumene with a propyl alkylating agent in the aforementioned superacid systems.
    Type: Grant
    Filed: February 6, 1984
    Date of Patent: October 15, 1985
    Assignee: PCUK Produits Chimiques Ugine Kuhlmann
    Inventor: George A. Olah
  • Patent number: 4522708
    Abstract: The present invention relates to catalysts for reforming petroleum products in mass form or supported for example, on aluminium or active carbon, the active part of which consists of tungsten and molybdenum carbides corresponding to the general formula:(Mox W.sub.1-x)y Czwherein0<x<11.ltoreq.y.ltoreq.20.8.ltoreq.z.ltoreq.1Nitridation prior to their use in a mixture H.sub.2 +N.sub.2 substantially increases the activity and selectivity thereof.These catalysts are not very sensitive to contamination by sulphur products.
    Type: Grant
    Filed: March 15, 1984
    Date of Patent: June 11, 1985
    Assignee: Eruotungstene-Poudres
    Inventors: Lucien Leclercq, Marcelle Provost
  • Patent number: 4440957
    Abstract: Process of preparing .beta.-isopropylnaphthalene substantially free of corresponding .alpha.-isomer, in yields amounting to 90% and more by a continuous two-stage process comprising (1) alkylating naphthalene with propylene at a temperature of about 150.degree.-280.degree. C. under a pressure of 5 to 30 atm in the presence of a phosphoric acid catalyst supported on a SiO.sub.2 carrier and using a mol ratio of 1/5 to 1/20 mol propylene to 1 mol naphthalene to isopropylate 45 to 65% of the naphthalene and form a mixture of .alpha.- and .beta.-isopropylnaphthalene and then without separating off the unreacted naphthalene, (2) heating the isomeric mixture from stage (1) in the presence of a phosphoric acid catalyst supported on SiO.sub.2, to a temperature of 180.degree.-280.degree. C. under an inert gas pressure of 5 to 30 atm until no further .beta.-isopropylnaphthalene is formed and recovering said .beta.-isopropylnaphthalene from the isomerization mixture.
    Type: Grant
    Filed: August 3, 1981
    Date of Patent: April 3, 1984
    Assignee: Bergwerksverband GmbH
    Inventors: Kurt Handrick, Georg Kolling, Paul Kiedel
  • Patent number: 4431857
    Abstract: Incorporation of above about 50 ppm water into feed of a hydrocarbon conversion process using an AMS-1B crystalline borosilicate-based catalyst alters the product distribution produced in such process.
    Type: Grant
    Filed: August 2, 1982
    Date of Patent: February 14, 1984
    Assignee: Standard Oil Company (Indiana)
    Inventor: Allen I. Feinstein
  • Patent number: 4385194
    Abstract: A method is disclosed for promoting isomerization of sym-octahydrophenanthrene (s-OHP) to sym-octahydroanthracene (s-OHA) in the presence of a catalyst provided by aluminum chloride or aluminum bromide, or a mixture of these two compounds. The rate of isomerization is increased by having the reaction run in the presence of an aralkyl halide such as benzyl chloride.
    Type: Grant
    Filed: March 5, 1982
    Date of Patent: May 24, 1983
    Assignee: Koppers Company, Inc.
    Inventor: William T. Gormley
  • Patent number: 4384156
    Abstract: A method is disclosed for promoting isomerization of sym-octahydrophenanthrene (s-OHP) to sym-octahydroanthracene (s-OHA) in the presence of a catalyst provided by aluminum chloride or aluminum bromide, or a mixture of these two compounds. The rate of isomerization is increased by having the reaction run in the presence of an aroyl halide, such as benzoyl chloride or isophthaloyl chloride.
    Type: Grant
    Filed: March 5, 1982
    Date of Patent: May 17, 1983
    Assignee: Koppers Company, Inc.
    Inventor: William T. Gormley
  • Patent number: 4376223
    Abstract: A method is disclosed for promoting isomerization of sym-octahydrophenanthrene (s-OHP) to sym-octahydroanthracene (s-OHA) in the presence of a catalyst provided by aluminum chloride or aluminum bromide, or a mixture of these two compounds. The rate of isomerization is increased by having the reaction run in the presence of an aryl phenone such as benzophenone.
    Type: Grant
    Filed: April 26, 1982
    Date of Patent: March 8, 1983
    Assignee: Koppers Company, Inc.
    Inventor: William T. Gormley
  • Patent number: 4376224
    Abstract: A method is disclosed for promoting isomerization of sym-octahydrophenanthrene (s-OHP) to sym-octahydroanthracene (s-OHA) in the presence of a catalyst provided by aluminum chloride or aluminum bromide, or a mixture of these two compounds. The rate of isomerization is increased by having the reaction run in the presence of an acyl peroxide such as benzoyl peroxide or lauroyl peroxide.
    Type: Grant
    Filed: April 26, 1982
    Date of Patent: March 8, 1983
    Assignee: Koppers Company, Inc.
    Inventor: William T. Gormley
  • Patent number: 4367360
    Abstract: A method is disclosed for extracting sym-octahydroanthracene (s-OHA) from a product isomer mixture formed by the aluminum chloride catalyzed isomerization of sym-octahydrophenanthrene (s-OHP). Isolation of the s-OHA product isomer is accomplished by contacting the reaction product mixture with a specified liquid hydrocarbon solvent into which the s-OHA product isomer and unconverted s-OHP isomer dissolve and separate from a residue. The undissolved residue comprises a complex made up of aluminum chloride catalyst and small amounts of the s-OHA and s-OHP isomers. This catalyst complex may be recycled into a fresh starting mixture of s-OHP isomer for catalysis of a subsequent s-OHP isomerization reaction.
    Type: Grant
    Filed: September 18, 1981
    Date of Patent: January 4, 1983
    Assignee: Koppers Company, Inc.
    Inventor: William T. Gormley
  • Patent number: 4367137
    Abstract: Hydrocarbons are converted by contacting them at hydrocarbon conversion conditions with an acidic multimetallic catalytic composite comprising a combination of catalytically effective amounts of a platinum group component, a cobalt component, a tin component, a phosphorus component and a halogen component with a porous carrier material. The platinum group, cobalt, tin, phosphorus and halogen components are present in the multimetallic catalyst in amounts respectively, calculated on an elemental basis, corresponding to about 0.01 to about 2 wt. % platinum group metal, about 0.05 to about 5 wt. % cobalt, about 0.01 to about 5 wt. % tin, about 0.01 to about 5 wt. % phosphorus and about 0.1 to about 3.5 wt. % halogen. A specific example of the type of hydrocarbon conversion process disclosed is a process for the catalytic reforming of a low-octane gasoline fraction wherein the gasoline fraction and a hydrogen stream are contacted with the acidic multimetallic catalyst disclosed herein at reforming conditions.
    Type: Grant
    Filed: November 23, 1981
    Date of Patent: January 4, 1983
    Assignee: UOP Inc.
    Inventors: George J. Antos, Tai-Hsiang Chao
  • Patent number: 4347397
    Abstract: A novel process for the reduction of durene produced in a methanol to gasoline conversion process is disclosed wherein either the total effluent from said process or a bottoms fraction containing durene is contacted with an isomerization catalyst at elevated temperatures in order to convert said durene.
    Type: Grant
    Filed: April 27, 1981
    Date of Patent: August 31, 1982
    Assignee: Mobil Oil Corporation
    Inventors: Francis G. Dwyer, Albin Huss, Jr.
  • Patent number: 4347398
    Abstract: Charge hydrocarbon stream containing diisopropyl toluene isomers is catalytically treated to recover product stream containing increased proportions of 1-methyl-3,5-diisopropyl benzene.
    Type: Grant
    Filed: July 13, 1980
    Date of Patent: August 31, 1982
    Assignee: Texaco Inc.
    Inventors: John M. Crone, Jr., Robert M. Suggitt
  • Patent number: 4343958
    Abstract: A process for the isomerization of acyclic hydrocarbons and alkylaromatic hydrocarbons is disclosed. The mixed-phase feed stream is heated and the liquid-phase portion of the feed stream is simultaneously vaporized by indirect heat exchange against the effluent of the reaction zone. Prior to this exchange, the effluent of the isomerization zone is heated in a fired heater to a temperature above that employed in the reaction zone. The inventive concept eliminates the need to pass mixed-phase feed streams through fired multi-pass heaters.
    Type: Grant
    Filed: April 28, 1981
    Date of Patent: August 10, 1982
    Assignee: UOP Inc.
    Inventor: Steve A. Gewartowski
  • Patent number: 4314091
    Abstract: Charge hydrocarbon stream containing diisopropyl toluene isomers is catalytically treated to recover product stream containing increased proportions of 1-methyl-3,5-diisopropyl benzene.
    Type: Grant
    Filed: March 31, 1980
    Date of Patent: February 2, 1982
    Assignee: Texaco Inc.
    Inventors: John M. Crone, Jr., Robert M. Suggitt
  • Patent number: 4313021
    Abstract: A process for the conversion of aromatic hydrocarbons, e.g., reacting an alkylating agent, preferably an olefin, with an aromatic hydrocarbon. The process uses a novel catalyst prepared by subjecting alumina to an anhydrous tetravalent titanium fluoride complex of an organic compound selected from the group of organic compounds containing at least one methoxy group per molecule of organic compounds having at least one electron donor atom and double bond per molecule, and heat treating the resulting impregnated alumina in an inert atmosphere.
    Type: Grant
    Filed: October 6, 1980
    Date of Patent: January 26, 1982
    Assignee: UOP Inc.
    Inventor: Ji-Yong Ryu
  • Patent number: 4268377
    Abstract: Hydrocarbons are converted by contacting them at hydrocarbon conversion conditions with a novel activated multimetallic catalytic composite comprising a combination of a catalytically effective amount of a pyrolyzed ruthenium carbonyl component with a porous carrier material containing a uniform dispersion of a catalytically effective amount of a platinum group component, which is maintained in the elemental metallic state during the incorporation and pyrolysis of the ruthenium carbonyl component, and of a rhenium component. In a highly preferred embodiment, this novel catalytic composite also contains a catalytically effective amount of a halogen component. The platinum group component, pyrolyzed ruthenium carbonyl component, rhenium component and optional halogen component are preferably present in the multimetallic catalytic composite in amounts, calculated on an elemental basis, corresponding to about 0.01 to about 2 wt. % of the uniformly dispersed platinum group metal, about 0.01 to about 2 wt.
    Type: Grant
    Filed: October 5, 1979
    Date of Patent: May 19, 1981
    Assignee: UOP Inc.
    Inventor: George J. Antos
  • Patent number: 4260842
    Abstract: It has been found that catalysts comprising zirconium hydrides, hydride alkyls and dihydrides bonded to metal or metalloid oxides in particular zirconium hydride bonded to silica, when contacted with olefins under mild conditions rapidly cause isomerization to thermodynamic mixtures.
    Type: Grant
    Filed: November 7, 1979
    Date of Patent: April 7, 1981
    Assignee: The Trustees of Princeton University
    Inventors: Jeffrey Schwartz, Michael D. Ward
  • Patent number: 4255606
    Abstract: An isomerization process for the production of desired isomers of aromatic hydrocarbons containing eight carbon atoms per molecule, i.e., para-xylene and ortho-xylene, from a mixture of aromatic hydrocarbons containing eight carbon atoms per molecule wherein yields of the desired carbon, are increased by incorporating an aliphatic hydrocarbon, e.g., n-pentane, in the feedstock for the process.
    Type: Grant
    Filed: November 28, 1979
    Date of Patent: March 10, 1981
    Assignee: Engelhard Minerals & Chemicals Corporation
    Inventor: Harold F. Tse
  • Patent number: 4243827
    Abstract: A process for the conversion of aromatic hydrocarbons, e.g., reacting an alkylating agent, preferably an olefin, with an aromatic hydrocarbon. The process uses a novel catalyst prepared by subjecting alumina to an anhydrous tetravalent titanium flouride complex of an organic compound selected from the group of organic compounds containing at least one methoxy group per molecule or organic compounds having at least one electron donor atom and double bond per molecule, and heat treating the resulting impregnated alumina in an inert atmosphere.
    Type: Grant
    Filed: April 6, 1979
    Date of Patent: January 6, 1981
    Assignee: UOP Inc.
    Inventor: Ji-Yong Ryu
  • Patent number: 4202996
    Abstract: Isomerizable hydrocarbons including paraffins, cycloparaffins, olefins and alkyl aromatics are isomerized by contacting the hydrocarbon at isomerization conditions with a catalytic composite comprising a combination of a nickel component, a molybdenum component and a platinum component with a zeolitic carrier material wherein said platinum component is present in an amount sufficient to result in the composite containing, on an elemental basis, about 0.2 to about 0.5 percent by weight platinum.
    Type: Grant
    Filed: December 26, 1978
    Date of Patent: May 13, 1980
    Assignee: UOP Inc.
    Inventor: Lee Hilfman
  • Patent number: 4188308
    Abstract: This invention relates to a method for preparing an acid catalyst which comprises contacting a copolymer of perflurovinyl ether and tetrafluoroethylene containing pendant sulfonate groups with a strong acid having a pKa of less than 1 to convert said sulfonate groups into sulfonic acid groups, removing the excess strong acid and salt formed from such conversion, preferably by washing said sulfonic acid group containing polymer with a solvent in which said salt and said acid are soluble, and removing said solvent from said sulfonic acid group containing polymer. Preferably the strong acid is nitric acid, e.g., aqueous nitric acid, and said solvent is aqueous. The excess solvent may be removed by drying at a temperature of from 50 to 200 degrees C., preferably at reduced pressures. The use of the catalyst prepared by this method for isomerization of hydrocarbons, e.g., xylene, and dealkylation of alkylbenzenes, e.g., diethylbenzene and diisopropylbenzene are also claimed.
    Type: Grant
    Filed: May 10, 1978
    Date of Patent: February 12, 1980
    Assignee: Varen Technology
    Inventor: Ronald J. Vaughan
  • Patent number: 4183804
    Abstract: Hydrocarbons are converted by contacting them at hydrocarbon conversion conditions with a novel activated multimetallic catalytic composite comprising a combination of a catalytically effective amount of a pyrolyzed ruthenium carbonyl component with a porous carrier material containing a uniform dispersion of a catalytically effective amount of a platinum group component which is maintained in the elemental metallic state. In a highly preferred embodiment, this novel catalytic composite also contains a catalytically effective amount of a halogen component. The platinum group component, pyrolyzed ruthenium carbonyl component and optional halogen component are preferably present in the multimetallic catalytic composite in amounts, calculated on an elemental basis, corresponding to about 0.01 to about 2 wt. % of the uniformly dispersed platinum group metal, about 0.01 to about 2 wt. % of carbonyl-derived ruthenium and about 0.1 to about 3.5 wt. % of halogen.
    Type: Grant
    Filed: November 4, 1977
    Date of Patent: January 15, 1980
    Assignee: UOP Inc.
    Inventor: George J. Antos
  • Patent number: 4175031
    Abstract: Hydrocarbons are converted by contacting them at hydrocarbon conversion conditions with a novel attenuated superactive multimetallic catalytic composite comprising a combination of a catalytically effective amount of a pyrolyzed rhenium carbonyl component with a porous carrier material containing a uniform dispersion of catalytically effective amounts of a platinum group component, which is maintained in the elemental metallic state, and of an indium component. In a highly preferred embodiment, this novel catalytic composite also contains a catalytically effective amount of a halogen component. The platinum group component, pyrolyzed rhenium carbonyl component, indium component and optional halogen component are preferably present in the multimetallic catalytic composite in amounts, calculated on an elemental basis, corresponding to about 0.01 to about 2 wt.% platinum group metal, about 0.01 to about 5 wt.% rhenium, about 0.01 to about 5% indium and about 0.1 to about 3.5 wt.% halogen.
    Type: Grant
    Filed: June 30, 1978
    Date of Patent: November 20, 1979
    Assignee: UOP Inc.
    Inventor: George J. Antos