H Halide Patents (Class 585/729)
  • Patent number: 8927800
    Abstract: We provide a method for making hydrocarbon products with reduced organic halide contamination, comprising: a. separating an effluent from an ionic liquid catalyzed hydrocarbon conversion reaction into: i. a hydrocarbon fraction comprising an organic halide contaminant and from greater than zero to less than 5000 wppm olefins; and ii. a used ionic liquid catalyst fraction comprising a used ionic liquid catalyst; and b. contacting the hydrocarbon fraction with an aromatic hydrocarbon reagent and an ionic liquid catalyst to reduce a level of the organic halide contaminant to from greater than zero to 20 wppm in a finished hydrocarbon product.
    Type: Grant
    Filed: December 14, 2012
    Date of Patent: January 6, 2015
    Assignee: Chevron U.S.A. Inc.
    Inventors: Cedrick Mahieux, Sven Ivar Hommeltoft
  • Patent number: 8884091
    Abstract: We provide an integrated process to produce alkylate gasoline, comprising: a. alkylating a mixture of hydrocarbons using a chloride-containing ionic liquid catalyst in an alkylation reactor to produce an alkylate gasoline comprising a chloride contaminant; b. hydro-regenerating the chloride-containing ionic liquid catalyst in a hydrogenation reactor; c. hydro-dechlorinating the alkylate gasoline comprising the chloride contaminant in a dechlorination reactor at a dechlorination pressure from 0 to 1000 psig of a hydrogenation pressure used in the hydrogenation reactor, to produce a dechlorinated alkylate gasoline; and d. feeding an off-gas, comprising 70 to 99.9 vol % hydrogen, from the dechlorination reactor to the hydrogenation reactor. We also provide an integrated alkylation process unit for conducting this process.
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: November 11, 2014
    Assignee: Chevron U.S.A. Inc.
    Inventors: Bi-Zeng Zhan, Thomas Van Harris, Hye Kyung Cho Timken
  • Patent number: 8674159
    Abstract: A process comprising: contacting a blend of hydrocarbons under hydroconversion conditions in a hydroconversion zone with a mixture of an acidic ionic liquid catalyst and at least one alkyl halide comprising at least 55 wt % halide and having a boiling point of 70° C. or higher. An alkylation process comprising: contacting a blend of hydrocarbons under alkylation conditions with a mixture of an acidic ionic liquid catalyst that is a chloroaluminate and at least one alkyl halide comprising 1,1,1-trichloroethane, tetrachloroethylene, or a mixture thereof; wherein greater than 99.9 wt % of an at least one olefin in the blend of hydrocarbons is alkylated. Also, a hydroconversion process comprising drying the alkyl halide.
    Type: Grant
    Filed: May 19, 2009
    Date of Patent: March 18, 2014
    Assignee: Chevron U.S.A. Inc.
    Inventor: Sven Ivar Hommeltoft
  • Patent number: 8323478
    Abstract: A process, comprising: a. taking a sample from a continuous alkylation reactor process; b. measuring a content of a halide in the sample; and c. within 45 minutes from the taking a sample, adjusting a flow of a halide containing additive comprising the halide to control a ratio of a yield of an alkylate gasoline and a yield of a middle distillate. Also a process, comprising: a. taking a sample from an effluent of an alkylation reactor in an alkylation reactor process; b. measuring a content of a halide in the sample; and c. in response to the measured content of the halide, adjusting a flow of a halide containing additive to a predetermined range that has been selected to obtain a ratio of a yield of an alkylate gasoline and a yield of a middle distillate from 0.31 to 4.0 in a product from the alkylation reactor.
    Type: Grant
    Filed: July 21, 2011
    Date of Patent: December 4, 2012
    Assignee: Chevron U.S.A. Inc.
    Inventors: Sven Ivar Hommeltoft, Howard S. Lacheen
  • Patent number: 8198499
    Abstract: A process for a liquid/liquid reaction employs a nozzle dispersion whereby liquid reactants and liquid catalyst are injected through at least one nozzle into a reaction zone to effect a reaction. The reaction can be alkylation of at least one isoparaffin with at least one olefin in the presence of an ionic liquid catalyst. The at least one nozzle provides intimate contact between the phases for greater product control and reaction control.
    Type: Grant
    Filed: December 28, 2007
    Date of Patent: June 12, 2012
    Assignee: Chevron U.S.A. Inc.
    Inventors: Huping Luo, Abdenour Kemoun, Hye-Kyung Timken
  • Patent number: 8183425
    Abstract: Provided is a process for producing low volatility, high quality gasoline blending components from a number of isoparaffin feed streams, olefin feed streams, and ionic liquid catalyst streams. The process entails providing an isoparaffin feed stream comprising isoparaffins, an olefin feed stream comprising olefins, and a catalyst stream comprising ionic liquid catalyst, and subsequently splitting at least the reactive olefin feed stream for feeding into the reaction zone at different locations.
    Type: Grant
    Filed: December 28, 2007
    Date of Patent: May 22, 2012
    Assignee: Chevron U.S.A. Inc.
    Inventors: Huping Luo, Abdenour Kemoun, Hye-Kyung Timken
  • Patent number: 8142725
    Abstract: An apparatus comprising: a) an alkylation reactor holding an ionic liquid catalyst and a reactant mixture, b) a means for measuring levels of a halide in an effluent from the alkylation reactor, and c) a control system that receives a signal in response to the measuring and communicates changes in an operating condition that influences the yield of products from the reactant mixture. The control system is responsive to deviations outside a predetermined range of halide level that has been selected to obtain a ratio of a yield of an alkylate gasoline and a yield of a middle distillate from 0.31 to 4.0 in the product from the alkylation reactor.
    Type: Grant
    Filed: July 8, 2011
    Date of Patent: March 27, 2012
    Assignee: Chevron U.S.A. Inc.
    Inventors: Sven Ivar Hommeltoft, Howard S. Lacheen
  • Patent number: 8070939
    Abstract: A process comprising: a) taking a sample from a continuous reactor process, b)measuring a content of a halide in the sample, and c) in response to the measured content of the halide, adjusting a flow of a halide containing additive comprising the halide to control the process. Also, an apparatus comprising: a) a reactor holding an ionic liquid catalyst and a reactant mixture, b) a means for measuring levels of a halide in an effluent from the reactor, and c) a control system that receives a signal in response to the measuring and communicates changes in an operating condition that influences the yield of a product in the reactant mixture.
    Type: Grant
    Filed: September 18, 2008
    Date of Patent: December 6, 2011
    Assignee: Chevron U.S.A. Inc.
    Inventors: Sven Ivar Hommeltoft, Howard S. Lacheen
  • Patent number: 7956230
    Abstract: A method for reducing halide concentration in a hydrocarbon product made by a hydrocarbon conversion process using an ionic liquid catalyst comprising a halogen-containing an acidic ionic liquid comprising: (i) separating at least a portion of the hydrocarbon product from the ionic liquid catalyst used in the hydrocarbon conversion process from the hydrocarbon product; (ii) contacting at least a portion of the separated hydrocarbon product with an ionic liquid catalyst having the same formula as the ionic liquid catalyst used in the hydrocarbon conversion process; (iii) separating at least a portion of the hydrocarbon product from the ionic liquid catalyst of step (ii); and (iv) recovering at least a portion of the separated hydrocarbon product of step (iii) having a halide concentration less than the halide concentration of the hydrocarbon product of step (i) is disclosed.
    Type: Grant
    Filed: December 21, 2007
    Date of Patent: June 7, 2011
    Assignee: Chevron U.S.A. Inc.
    Inventors: Hye-Kyung C. Timken, Michael S. Driver, Thomas V. Harris
  • Patent number: 7674945
    Abstract: The present invention discloses a process for alkylation of an aromatic hydrocarbon or isoalkane with an olefin over the catalysis of a solid acid, comprising contacting a reaction material containing an aromatic hydrocarbon or C4-C6 isoalkane, C2-C18 monoolefin and a compound containing a strongly electronegative element as promoter with a solid acid catalyst to carry out the alkylation, characterized in that the solid acid catalyst is contacted with a compound having a strongly electronegative element prior to its contact with the reaction material. Said process not only greatly increases the selectivity of the target product of the alkylation but also improves stability of the solid acid catalyst.
    Type: Grant
    Filed: January 19, 2005
    Date of Patent: March 9, 2010
    Assignee: China Petroleum & Chemical Corporation
    Inventors: Yigong He, Zheng Man
  • Patent number: 7569740
    Abstract: A process and method for making a superior lubricant or distillate fuel component by the alkylation of C5+ olefins with isoparaffins to produce a “capped” (alkylated) olefin using an acidic chloroaluminate ionic liquid catalyst system. Preferably the catalyst system includes a Brönsted acid.
    Type: Grant
    Filed: December 20, 2005
    Date of Patent: August 4, 2009
    Assignee: Chevron U.S.A. Inc.
    Inventor: Saleh Elomari
  • Patent number: 5895831
    Abstract: A process for the production of motor fuel alkylate by reacting an alkene hydrocarbon, an alkane hydrocarbon and a hydrogen halide with a solid alkylation catalyst disposed in swing beds. The spent solid alkylation catalyst is regenerated in a highly integrated flow scheme associated with the alkylate recovery.
    Type: Grant
    Filed: December 4, 1996
    Date of Patent: April 20, 1999
    Assignee: UOP LLC
    Inventors: Robert S. Brasier, Paul A. Sechrist, Dale J. Shields
  • Patent number: 5866747
    Abstract: Although alkenes commonly are used to alkylate alkanes using various solid acid catalysts, the process is severely hampered by short catalyst lifetimes attending substantial alkene oligomerization. This problem can be avoided by using an alkene-alkyl chloride mixture as the alkylating agent. Thus, alkylation of isobutane by a butyl chloride/butene mixture at a molar ratio of 1:3 in the presence of an AlCl.sub.3 -type Friedel-Crafts catalyst at 30.degree. C. maintains at least an 80% conversion of (alkene and alkyl chloride) for almost twice as long as is the case for a 1:19 molar ratio of butyl chloride/butene.
    Type: Grant
    Filed: June 2, 1997
    Date of Patent: February 2, 1999
    Assignee: UOP LLC
    Inventor: Paul T. Barger
  • Patent number: 5849977
    Abstract: A process for the alkylation of alkenes having from 2 to 6 carbon atoms with an alkane having from 4 to 6 carbon atoms to afford an alkylate comprises reacting in the liquid phase the alkene and alkane under alkylation conditions in the presence of a novel catalyst comprising: a) a refractory inorganic oxide, b) the reaction product of a first metal halide and bound surface hydroxyl groups of the refractory inorganic oxide, c) a second metal cation, and d) optionally a zerovalent third metal. The refractory inorganic oxide is selected form the group consisting of alumina, titania, zirconia, chromia, silica, boria, silica-alumina, and combinations thereof and the first metal halide is a fluoride, chloride, or bromide of aluminum or boron. The second metal cation is selected from the group consisting of: monovalent metal cations in an amount from 0.0026 up to about 0.20 gram atoms per 100 grams refractory inorganic oxide for lithium, potassium, cesium, rubidium, silver, and copper, and from 0.012 to about 0.
    Type: Grant
    Filed: April 10, 1996
    Date of Patent: December 15, 1998
    Assignee: UOP
    Inventors: Joseph A. Kocal, Anil R. Oroskar
  • Patent number: 5406018
    Abstract: A discrete catalyst and processes for the isomerization of alkanes and the alkylation of isoalkanes under homogenous fluid conditions. The catalyst is formed by contacting, under fluid conditions, a homogenous fluid containing a paraffin hydrocarbon having from 4 to 12 carbon atoms with a Lewis acid/protic Bronsted acid pair and a transition metal to produce a discrete catalytic complex that is soluble in the fluid. The discrete catalyst is the reaction product of the acid pair and alkanes and includes hydrocarbon ligands of limited chain length rendering it soluble in the fluid. The catalyst is active for the isomerization of alkanes and olefins, and the alkylation of isoalkanes, under homogenus fluid conditions.
    Type: Grant
    Filed: December 21, 1992
    Date of Patent: April 11, 1995
    Assignee: Kerr-McGee Corporation
    Inventor: Larry G. Sherman
  • Patent number: 4426545
    Abstract: A process is described for paraffin-olefin alkylation under strong acid conditions in which an adamantylalkyl carboxylic acid or sulfonic acid is used to substantially improve the efficiency of reaction.
    Type: Grant
    Filed: March 15, 1983
    Date of Patent: January 17, 1984
    Assignee: Exxon Research and Engineering Co.
    Inventor: George M. Kramer
  • Patent number: 4357481
    Abstract: A process is described for paraffin-olefin alkylation under strong acid conditions in which an adamantane hydrocarbon is used to substantially increase the reaction rate of the alkylation.
    Type: Grant
    Filed: August 31, 1981
    Date of Patent: November 2, 1982
    Assignee: Exxon Research and Engineering Co.
    Inventor: George M. Kramer
  • Patent number: 4357482
    Abstract: A process is described for paraffin-olefin alkylation under strong acid conditions in which an aminoalkyladamantane hydrocarbon is used to substantially improve the reaction.
    Type: Grant
    Filed: August 31, 1981
    Date of Patent: November 2, 1982
    Assignee: Exxon Research and Engineering Co.
    Inventor: George M. Kramer