With Additional Nonhydrocarbon Agent Patents (Class 585/728)
  • 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: 8865960
    Abstract: Methods for starting and operating ionic liquid catalyzed hydrocarbon conversion processes and systems to provide maximum process efficiency, system reliability and equipment longevity may include: purging air and free water from at least a portion of the system; introducing at least one reactant into the at least a portion of the system; and re-circulating the at least one reactant through the at least a portion of the system, via at least one feed dryer unit, until the at least one reactant exiting the at least a portion of the system has a water content at or below a threshold value, prior to the introduction of an ionic liquid catalyst and/or additional reactant(s) and feeds into the system.
    Type: Grant
    Filed: June 28, 2010
    Date of Patent: October 21, 2014
    Assignee: Chevron U.S.A. Inc.
    Inventors: Hye-Kyung Timken, Howard S. Lacheen, Shawn S. Winter
  • Patent number: 8729329
    Abstract: A process, comprising: a) introducing an acidic ionic liquid to a reactor comprising a solid support; b) feeding to the reactor a feed stream comprising a Brønsted acid and a hydrocarbon mixture comprising: i. at least one alkylatable hydrocarbon, and ii. at least one alkylating agent; and c) collecting one or more liquid hydrocarbon products in an effluent from the reactor, wherein the one or more liquid hydrocarbon products are oligomer products, alkylate products, or mixtures thereof, made from the alkylatable hydrocarbon. Also, a process, comprising: a) introducing an acidic ionic liquid to a reactor comprising a solid support; b) feeding to the reactor a feed stream comprising a Brønsted acid and a hydrocarbon mixture; c) cooling the reactor by evaporating a volatile hydrocarbon from a reaction zone in the reactor; and d) collecting one or more liquid hydrocarbon products made from the hydrocarbon mixture.
    Type: Grant
    Filed: June 28, 2010
    Date of Patent: May 20, 2014
    Assignee: Chevron U.S.A. Inc.
    Inventors: Sven Ivar Hommeltoft, Zhen Zhou
  • Patent number: 8497404
    Abstract: Processes for upgrading Fischer-Tropsch condensate olefins by alkylation of hydrocrackate involves providing an olefin enriched condensate stream and further providing a Fischer-Tropsch derived hydrocarbon stream comprising wax, hydrocracking the latter Fischer-Tropsch hydrocarbon stream to provide a distillate enriched hydrocracked product comprising isoparaffins, and alkylating the olefins with the isoparaffins in an alkylation zone to provide an alkylate product. The alkylate product is fed to a distillation unit together with the hydrocracked product, while a naphtha containing fraction from the distillation unit is fed to the alkylation zone together with the olefin enriched hydrocarbon stream.
    Type: Grant
    Filed: February 12, 2013
    Date of Patent: July 30, 2013
    Assignee: Chevron U.S.A. Inc.
    Inventors: Sven Ivar Hommeltoft, Bi-Zeng Zhan
  • Patent number: 8436221
    Abstract: Processes for upgrading Fischer-Tropsch condensate olefins by alkylation of hydrocrackate may involve providing an olefin enriched condensate stream and further providing a Fischer-Tropsch derived hydrocarbon stream comprising wax, hydrocracking the latter Fischer-Tropsch hydrocarbon stream to provide a distillate enriched hydrocracked product comprising isoparaffins, and alkylating the olefins with the isoparaffins in an alkylation zone to provide an alkylate product. The alkylate product may be fed to a distillation unit together with the hydrocracked product, while a naphtha containing fraction from the distillation unit may be fed to the alkylation zone together with the olefin enriched hydrocarbon stream.
    Type: Grant
    Filed: December 22, 2010
    Date of Patent: May 7, 2013
    Assignee: Chevron U.S.A. Inc.
    Inventors: Sven Ivar Hommeltoft, Bi-Zeng Zhan
  • 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: 8293962
    Abstract: A process for producing a gasoline blending component and a middle distillate, comprising adjusting a level of a halide containing additive provided to an ionic liquid alkylation reactor to shift selectivity towards heavier products, and recovering a low volatility gasoline blending component and the middle distillate.
    Type: Grant
    Filed: April 10, 2012
    Date of Patent: October 23, 2012
    Assignee: Chevron U.S.A. Inc.
    Inventors: Sven Ivar Hommeltoft, Stephen Joseph Miller, Ajit Ramchandra Pradhan
  • Publication number: 20120226086
    Abstract: A process for producing a gasoline blending component and a middle distillate, comprising adjusting a level of a halide containing additive provided to an ionic liquid alkylation reactor to shift selectivity towards heavier products, and recovering a low volatility gasoline blending component and the middle distillate.
    Type: Application
    Filed: April 10, 2012
    Publication date: September 6, 2012
    Applicant: Chevron U.S.A. Inc.
    Inventors: Sven Ivar Hommeltoft, Stephen Joseph Miller, Ajit Ramchandra Pradhan
  • Patent number: 8252968
    Abstract: A process for producing a low volatility gasoline blending component and a middle distillate, comprising alkylating a hydrocarbon stream comprising at least one olefin having from 2 to 4 carbon atoms and at least one paraffin having from 4 to 6 carbon atoms with an ionic liquid catalyst and an unsupported halide containing additive, and separating the alkylate into at least the low volatility gasoline blending component and the middle distillate, wherein the middle distillate is a fuel suitable for use as a jet fuel or jet fuel blending component. Also, a process for producing a gasoline blending component and a middle distillate, comprising adjusting a level of a halide containing additive provided to an ionic liquid alkylation reactor to shift selectivity towards heavier products, and recovering a low volatility gasoline blending component and the middle distillate. Also, processes comprising alkylating isobutane with butene over specific chloroaluminate ionic liquids.
    Type: Grant
    Filed: February 25, 2011
    Date of Patent: August 28, 2012
    Assignee: Chevron U.S.A. Inc.
    Inventors: Sven Ivar Hommeltoft, Stephen J. Miller, Ajit Ramchandra Pradhan
  • Patent number: 8198500
    Abstract: A process comprising contacting an olefin feed from a Fischer-Tropsch condensate with an isoparaffin, an acidic chloroaluminate ionic liquid catalyst, and a Brönsted acid; whereby a base oil is produced by concurrent oligomerization and alkylation.
    Type: Grant
    Filed: November 4, 2011
    Date of Patent: June 12, 2012
    Assignee: Chevron U.S.A. Inc.
    Inventors: Saleh Elomari, Russell Roland Krug, Stephen Joseph Miller
  • Patent number: 8198494
    Abstract: A process for producing alkylate comprising contacting a first hydrocarbon stream comprising at least one olefin having from 2 to 6 carbon atoms which contains 1-butene with an isomerization catalyst under conditions favoring the isomerization of 1-butene to 2-butene so the isomerized stream contains a greater concentration of 2-butene than the first hydrocarbon stream and contacting the isomerized stream and a second hydrocarbon stream comprising at least one isoparaffin having from 4 to 6 carbon atoms with an acidic ionic liquid catalyst under alkylation conditions to produce an alkylate stream, wherein the alkylate stream has a RON that is increased from 5 to 32 numbers compared to a comparison alkylate stream made from the first hydrocarbon stream without the step of contacting with the isomerization catalyst.
    Type: Grant
    Filed: February 21, 2011
    Date of Patent: June 12, 2012
    Assignee: Chevron U.S.A. Inc.
    Inventors: Saleh Elomari, Hye Kyung C. Tlmken
  • 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
  • Publication number: 20110319695
    Abstract: A process, comprising: a) introducing an acidic ionic liquid to a reactor comprising a solid support; b) feeding to the reactor a feed stream comprising a Brønsted acid and a hydrocarbon mixture comprising: i. at least one alkylatable hydrocarbon, and ii. at least one alkylating agent; and c) collecting one or more liquid hydrocarbon products in an effluent from the reactor, wherein the one or more liquid hydrocarbon products are oligomer products, alkylate products, or mixtures thereof, made from the alkylatable hydrocarbon. Also, a process, comprising: a) introducing an acidic ionic liquid to a reactor comprising a solid support; b) feeding to the reactor a feed stream comprising a Brønsted acid and a hydrocarbon mixture; c) cooling the reactor by evaporating a volatile hydrocarbon from a reaction zone in the reactor; and d) collecting one or more liquid hydrocarbon products made from the hydrocarbon mixture.
    Type: Application
    Filed: June 28, 2010
    Publication date: December 29, 2011
    Inventors: Sven Ivar Hommeltoft, Zhen Zhou
  • 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
  • Publication number: 20110105820
    Abstract: Methods and compositions for stabilizing the activity of catalytic compositions during catalytic processes, such as alkylation. A catalytic composition comprising a partially deactivated ionic liquid catalyst may be regenerated by reaction with a metal to form reactivated catalyst and an inorganic catalyst precursor; and the catalytic composition may be amended in-process by addition of an organic catalyst precursor for reaction with the inorganic catalyst precursor to form fresh ionic liquid catalyst. The organic catalyst precursor may be protected from water, e.g., during handling, by hydrophobic material(s).
    Type: Application
    Filed: November 3, 2009
    Publication date: May 5, 2011
    Inventor: Thomas V. Harris
  • Patent number: 7923594
    Abstract: An alkylation process, comprising providing an isoparaffin feed that comprises at least 20 wt % C5+, providing a hydrocarbon stream that comprises at least 20 wt % C5+ olefins, and contacting the isoparaffin feed and the hydrocarbon stream with an ionic liquid catalyst under alkylation conditions wherein a middle distillate is produced. The middle distillate has less than 10 ppm sulfur and less than 3 wt % olefin. An alkylation process comprising contacting a naphtha with a low RON and a hydrocarbon stream comprising C5 olefins to an ionic liquid alkylation reactor under alkylation conditions, and recovering a middle distillate comprising less than 3 wt % olefin. A refinery process, comprising a hydrocracker that produces C5+ isoparaffin, a FC cracker that produces a hydrocarbon stream comprising a C5+ olefin, and an ionic liquid alkylation reactor that produces a high yield of middle distillate.
    Type: Grant
    Filed: July 31, 2008
    Date of Patent: April 12, 2011
    Assignee: Chevron U.S.A. Inc.
    Inventor: Sven Ivar Hommeltoft
  • Patent number: 7923593
    Abstract: A process for producing a middle distillate or a middle distillate blending component, comprising contacting a feed comprising an olefin, an isoparaffin, and less than 5 wt % oligomerized olefin, in an ionic liquid alkylation zone with an acidic haloaluminate ionic liquid, at alkylation conditions; and recovering an effluent comprising an alkylated product that has greater than 35 vol % C10+ and less than 1 vol % C55+. Also processes for producing a middle distillate by alkylating isobutane and butene in the presence of defined chloroaluminate ionic liquid catalysts, wherein a separating step separates the middle distillate and wherein the middle distillate is from 20 wt % or higher of the total alkylate product. Also a process for producing middle distillate with FC cracker feed comprising olefins. A separated middle distillate has greater than 30 vol % C10+, less than 1 vol % C55+, and a cloud point less than ?50° C.
    Type: Grant
    Filed: July 31, 2008
    Date of Patent: April 12, 2011
    Assignee: Chevron U.S.A. Inc.
    Inventors: Sven Ivar Hommeltoft, Stephen J. Miller, Ajit Pradhan
  • Patent number: 7919663
    Abstract: A process for producing a low volatility gasoline blending component and a middle distillate, comprising alkylating a hydrocarbon stream comprising at least one olefin having from 2 to 6 carbon atoms and at least one paraffin having from 4 to 6 carbon atoms with an ionic liquid catalyst and an unsupported halide containing additive, and separating the alkylate into at least the low volatility gasoline blending component and the middle distillate, wherein the middle distillate is a fuel suitable for use as a jet fuel or jet fuel blending component. Also, a process for producing a gasoline blending component and a middle distillate, comprising adjusting a level of a halide containing additive provided to an ionic liquid alkylation reactor to shift selectivity towards heavier products, and recovering a low volatility gasoline blending component and the middle distillate. Also, processes comprising alkylating isobutane with butene over specific chloroaluminate ionic liquids.
    Type: Grant
    Filed: July 31, 2008
    Date of Patent: April 5, 2011
    Assignee: Chevron U.S.A. Inc.
    Inventors: Sven Ivar Hommeltoft, Stephen J. Miller, Ajit Pradhan
  • Patent number: 7919664
    Abstract: A process for producing a jet fuel, comprising contacting an olefin and an isoparaffin with an unsupported catalyst system comprising an ionic liquid catalyst and a halide containing additive in an alkylation zone under alkylation conditions to make an alkylate product, and recovering the jet fuel from the alkylate product, wherein the jet fuel meets the boiling point, flash point, smoke point, heat of combustion, and freeze point requirements for Jet A-1 fuel. Also a process for producing a jet fuel, comprising providing a feed produced in a FC cracker comprising olefins, mixing the feed with an isoparaffin, alkylating the mixed feed in an ionic liquid alkylation zone, and separating the jet fuel from the alkylated product. We also provide a process comprising alkylating isobutane and butene in the presence of specific chloroaluminate ionic liquid catalysts, to produce a jet fuel.
    Type: Grant
    Filed: July 31, 2008
    Date of Patent: April 5, 2011
    Assignee: Chevron U.S.A. Inc.
    Inventors: Sven Ivar Hommeltoft, Stephen J. Miller, Ajit Pradhan
  • Patent number: 7915468
    Abstract: A process for producing alkylate comprising contacting a first hydrocarbon stream comprising at least one olefin having from 2 to 6 carbon atoms which contains 1-butene with an isomerization catalyst under conditions favoring the isomerization of 1-butene to 2-butene so the isomerized stream contains a greater concentration of 2-butene than the first hydrocarbon stream and contacting the isomerized stream and a second hydrocarbon stream comprising at least one isoparaffin having from 3 to 6 carbon atoms with an acidic ionic liquid catalyst under alkylation conditions to produce an alkylate stream is disclosed.
    Type: Grant
    Filed: April 3, 2009
    Date of Patent: March 29, 2011
    Assignee: Chevron U.S.A. Inc.
    Inventors: Hye-Kyung C. Timken, Saleh Elomari
  • Patent number: 7902419
    Abstract: An alkylation process comprising contacting a first hydrocarbon feed comprising at least one olefin having from 2 to 6 carbon atoms and a second hydrocarbon feed comprising at least one isoparaffin having from 3 to 6 carbon atoms with a halide-based acidic ionic liquid catalyst under alkylation conditions to produce an alkylate containing an organic halide and contacting at least a portion of the alkylate with a hydrotreating catalyst in the presence of hydrogen under hydrotreating conditions to reduce the concentration of the organic halide in the alkylate is disclosed.
    Type: Grant
    Filed: March 31, 2009
    Date of Patent: March 8, 2011
    Assignee: Chevron U.S.A. Inc
    Inventors: Michael S. Driver, Gunther H. Dieckmann
  • Patent number: 7732654
    Abstract: We provide a process for making a fuel or lubricant component, comprising: performing alkylation and oligomerization by contacting a stream comprising one or more olefins and one or more isoparaffins, wherein a molar ratio of the one or more olefins to the one or more isoparaffins in the stream is at least 0.8, an acidic chloroaluminate ionic liquid catalyst, and a halohalide; and recovering the fuel or lubricant component having a Bromine Number of less than 4. We provide a process comprising performing concurrent alkylation and oligomerization. We also provide a process for making a lubricant component having a kinematic viscosity at 100° C. of at least 6.9 mm2/s, a VI of at least 134, a cloud point less than or equal to ?28° C., and a Bromine Number of less than or equal to 6.1.
    Type: Grant
    Filed: June 9, 2009
    Date of Patent: June 8, 2010
    Assignee: Chevron U.S.A. Inc.
    Inventors: Saleh Elomari, Russell R. Krug
  • Patent number: 7723556
    Abstract: We provide a process for making a base oil, comprising: a) selecting an olefin feed produced by thermal cracking of a waxy feed; b) oligomerizing the olefin feed in an ionic liquid oligomerization zone at a set of oligomerization conditions to form an oligomer; and c) alkylating the oligomer in the presence of an isoparaffin, in an ionic liquid alkylation zone, at a set of alkylation conditions to form an alkylated oligomeric product having a kinematic viscosity at 100° C. of 6.9 mm2/s or greater, a VI of at least 134, and a Bromine Number of less than 4. We provide a process to make base oil from an olefin feed produced in a FCC unit. We also provide a process to make two or more viscosity grades of base oil from an olefin feed produced by thermal cracking of a waxy feed.
    Type: Grant
    Filed: July 6, 2009
    Date of Patent: May 25, 2010
    Assignee: Chevron U.S.A. Inc.
    Inventors: Saleh Elomari, Russell R. Krug, Stephen J. Miller
  • Patent number: 7576252
    Abstract: A process and method for making a superior lubricant or distillate fuel component by the oligomerization/alkylation of a mixture comprising olefins and isoparaffins to produce an alkylated (“capped”) olefin oligomer using an acidic chloroaluminate ionic liquid catalyst system. Preferably the ionic liquid catalyst system comprises a Brönsted acid.
    Type: Grant
    Filed: December 20, 2005
    Date of Patent: August 18, 2009
    Assignee: Chevron U.S.A. Inc.
    Inventors: Saleh Elomari, Russell Krug
  • 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: 7553999
    Abstract: A process for producing alkylate comprising contacting a first hydrocarbon stream comprising at least one olefin having from 2 to 6 carbon atoms which contains 1-butene with an isomerization catalyst under conditions favoring the isomerization of 1-butene to 2-butene so the isomerized stream contains a greater concentration of 2-butene than the first hydrocarbon stream and contacting the isomerized stream and a second hydrocarbon stream comprising at least one isoparaffin having from 3 to 6 carbon atoms with an acidic ionic liquid catalyst under alkylation conditions to produce an alkylate stream is disclosed.
    Type: Grant
    Filed: December 14, 2006
    Date of Patent: June 30, 2009
    Assignee: Chevron U.S.A. Inc.
    Inventors: Saleh Elomari, Hye-Kyung Timken
  • Patent number: 7538256
    Abstract: An alkylation process comprising contacting a first hydrocarbon feed comprising at least one olefin having from 2 to 6 carbon atoms and a second hydrocarbon feed comprising at least one isoparaffin having from 3 to 6 carbon atoms with a halide-based acidic ionic liquid catalyst under alkylation conditions to produce an alkylate containing an organic halide and contacting at least a portion of the alkylate with a hydrotreating catalyst in the presence of hydrogen under hydrotreating conditions to reduce the concentration of the organic halide is disclosed.
    Type: Grant
    Filed: December 12, 2006
    Date of Patent: May 26, 2009
    Assignee: Chevron U.S.A., Inc.
    Inventors: Michael S. Driver, Gunther Dieckmann
  • Patent number: 7531707
    Abstract: A process for the production of a high quality gasoline blending components from refinery process streams by the alkylation of light isoparaffins with olefins using an ionic liquid catalyst is disclosed. The alkylation process comprises contacting a hydrocarbon mixture comprising at least one olefin having from 2 to 6 carbon atoms and at least one isoparaffin having from 3 to 6 carbon atoms under alkylation conditions, said catalyst comprising a mixture of at least one acidic ionic liquid and at least one alkyl halide. The alkylhalide by reacting to at least a portion of the olefin with a hydrogen halide.
    Type: Grant
    Filed: December 13, 2006
    Date of Patent: May 12, 2009
    Assignee: Chevron U.S.A., Inc
    Inventors: Thomas V. Harris, Michael Driver, Saleh Elomari, Hye-Kyung C. Timken
  • Patent number: 7495144
    Abstract: A process for the production of a high quality gasoline blending components from refinery process streams by the alkylation of light isoparaffins with olefins using an ionic liquid catalyst is disclosed. The alkylation process comprises contacting a hydrocarbon mixture comprising at least one olefin having from 2 to 6 carbon atoms and at least one isoparaffin having from 3 to 6 carbon atoms under alkylation conditions, said catalyst comprising a mixture of at least one acidic ionic liquid and at least one alkyl halide.
    Type: Grant
    Filed: March 24, 2006
    Date of Patent: February 24, 2009
    Assignee: Chevron U.S.A. Inc.
    Inventor: Saleh Elomari
  • Patent number: 7432409
    Abstract: A process for the production of a high quality gasoline blending components from refinery process streams by the alkylation of light isoparaffins with olefins using an ionic liquid catalyst is disclosed. The process includes reacting a refinery stream containing isopentane and/or isobutane with a refinery stream containing ethylene and/or propylene and butylenes under alkylation conditions in the presence of a chloroaluminate ionic liquid catalyst comprising a hydrocarbyl substituted pyridinium chloroaluminate or a hydrocarbyl substituted imidazolium chloroaluminate of the general formulas A and B, respectively. Where R?H, methlyl, ethyl, propyl, butyl, pentyl or hexyl group and X is a chloroaluminate, and R1 and R2=H, methyl, ethyl, propyl, butyl, pentyl or hexyl group and where R1 and R2 may or may not be the same.
    Type: Grant
    Filed: December 21, 2004
    Date of Patent: October 7, 2008
    Assignee: Chevron U.S.A. Inc.
    Inventors: Saleh Elomari, Steve Trumbull, Hye Kyung C. Timken, Robert Cleverdon
  • Patent number: 6695965
    Abstract: A wax blending process is disclosed which retains the desirable properties of a Fischer-Tropsch wax, while adjusting the hardness of the wax to within to a desired range. The invention utilizes a synergistic effect between hard virgin Fischer-Tropsch wax and softer mildly isomerized Fischer-Tropsch wax in a blending process which allows the artisan to adjust the hardness of a wax product to within desired ranges. The process involves passing a Fischer-Tropsch wax over a hydroisomerization catalyst under predetermined conditions including relatively mild temperatures such that chemical conversions (e.g., hydrogenation and mild isomerization) take place while less than 10% boiling point conversion (hydrocracking) occurs, thus preserving overall isomerized wax yield.
    Type: Grant
    Filed: April 4, 2000
    Date of Patent: February 24, 2004
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Robert J. Wittenbrink, Daniel Francis Ryan
  • Patent number: 6103947
    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: December 22, 1998
    Date of Patent: August 15, 2000
    Assignee: UOP LLC
    Inventor: Paul T. Barger
  • 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: 5763729
    Abstract: Although olefins commonly are used to alkylate alkanes using various solid acid catalysts, the process is severely hampered by short catalyst lifetimes attending substantial olefin oligomerization. This problem can be avoided by using an alkyl chloride as the alkylating agent. Thus, alkylation of isobutane by olefin in the presence of a modified, AlCl.sub.3 -type Friedel-Crafts catalyst at 30.degree.C falls to about 77% in four hours, whereas alkylation with sec-butyl chloride at the same conditions fell to 88% over 30 hours.
    Type: Grant
    Filed: August 8, 1996
    Date of Patent: June 9, 1998
    Assignee: UOP
    Inventor: Paul T. Barger
  • Patent number: 5750455
    Abstract: The invention concerns a catalytic composition resulting from mixing at least one aluminum halide, at least one quaternary ammonium halide and/or at least one amine halohydrate and at least one cuprous compound, preferable a halide. The invention also concerns a process for the alkylation of isoparaffins by olefins with that composition.
    Type: Grant
    Filed: October 24, 1995
    Date of Patent: May 12, 1998
    Assignee: Institut Francais Du Petrole
    Inventors: Yves Chauvin, Andre Hirschauer, Helene Olivier
  • Patent number: 5744682
    Abstract: A novel catalyst for alkylating an alkene with an alkane to give an alkylate product has been developed. The catalyst comprises a refractory inorganic oxide on which is dispersed a Group VIII metal, a metal cation and the reaction product of a metal halide and bound surface hydroxyl groups of the refractory inorganic oxide. The catalyst is characterized in that the Group VIII metal is concentrated in an outer layer of the catalyst particle.
    Type: Grant
    Filed: May 30, 1995
    Date of Patent: April 28, 1998
    Assignee: UOP
    Inventors: Thomas K. McBride, Jr., Maureen L. Bricker, Karl Z. Steigleder
  • Patent number: 5731256
    Abstract: The present invention concerns a catalyst comprising a porous organic or mineral support, preferably silica, and an acidic phase containing B(OSO.sub.2 CF.sub.3).sub.3 and at least one acid selected from the group formed by sulphuric acid (H.sub.2 SO.sub.4) and trifluoromethane sulphonic acid (CF.sub.3 SO.sub.3 H), the support having been impregnated by said acidic phase, said catalyst being such that it is constituted essentially by particles with an average diameter of between 0.1 and 150 .mu.m, such that the support, prior to its impregnation with said acidic phase, has a total pore volume of between 0.5 and 6 cm.sup.3 per gram and said catalyst being characterized in that said acidic phase contains:between 0.1 and 70% by weight of B(OSO.sub.2 CF.sub.3).sub.3 ;between 0 and 90% by weight of H.sub.2 SO.sub.4 ;between 0 and 90% by weight of CF.sub.3 SO.sub.3 H.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: March 24, 1998
    Assignee: Institut Francais du Petrole
    Inventors: Eric Benazzi, Jean-Fran.cedilla.ois Joly, Christian Marcilly
  • Patent number: 5728911
    Abstract: A copolymer having an RSV less than 0.6 and a process for its preparation in which ethylene, at least one other 1-alkene and, optionally, an aliphatic or alicyclic polyunsaturated monomer are polymerized in the presence of a catalyst system containing (1) a compound of vanadium, (2) at least one alkyl aluminum halide, (3) an .alpha.-halo, ketoaromatic promoter and (4) a chain transfer agent in which the molar ratio of alkyl groups of the alkyl aluminum halide to halogen atoms is at least 1.5.
    Type: Grant
    Filed: November 27, 1995
    Date of Patent: March 17, 1998
    Assignee: DSM Copolymer, Inc.
    Inventor: James R. Hall
  • Patent number: 5481054
    Abstract: Immobilized Lewis Acid catalyst comprising polymer having at least one Lewis Acid immobilized within the structure therein, said polymer having monomer units represented by the structural formula:--[A].sub.a --[B].sub.b --[C].sub.c --whereina represents about 1 to about 99 mole %b represents about 0 to about 50 mole %c represents about 1 to about 99 mole %a+b+c is preferably about 100%; ##STR1## C is selected from the group consisting of: ##STR2## (III) combinations thereof, wherein D is OH, halide, OR.sup.4, NH.sub.2, NHR.sup.3, OM', or OM";E is the residue of the reaction of at least one Lewis Acid with the D substituent of monomer unit B;R.sup.1 represents proton, C.sub.1 -C.sub.24 alkyl group, or C.sub.3 -C.sub.24 cycloalkyl;R.sup.2 represents C.sub.1 -C.sub.24 alkylene group, C.sub.3 -C.sub.24 cycloalkylene, C.sub.6 -C.sub.18 arylene, or C.sub.7 -C.sub.30 alkylarylene;R.sup.3 represents C.sub.1 -C.sub.24 alkyl, C.sub.3 -C.sub.24 cycloalkyl, C.sub.1 -C.sub.24 aryl, or C.sub.7 -C.sub.30 alkylaryl;R.sup.
    Type: Grant
    Filed: March 3, 1995
    Date of Patent: January 2, 1996
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Tze-Chiang Chung, Frank J. Chen, Jon E. Stanat, Alok Kumar
  • Patent number: 5365010
    Abstract: This invention is a process for the regeneration of a catalyst system component comprising certain transition aluminas promoted with a Lewis acid (preferably BF.sub.3) which have been used in the alkylation of isoparaffin with olefins. The process involves the calcination of the catalyst system component to volatilize and to oxidize the reaction product residue adhering to the solid catalyst. The process may include recovery and recycle of the involved Lewis acid.
    Type: Grant
    Filed: June 20, 1991
    Date of Patent: November 15, 1994
    Assignee: Catalytica, Inc.
    Inventors: Pradip Rao, David L. King, Michael D. Cooper, Jerome E. Say
  • Patent number: 5326923
    Abstract: This invention is a process for the regeneration of solid acidic hydrocarbon conversion catalysts, but particularly certain transition aluminas and zeolites promoted with Lewis acids (preferably BF.sub.3) which have been used in the alkylation of isoparaffins with olefins. The process involves the removal of some portion of the reaction product residue adhering to the solid catalyst by contact with a solvent to partially recover the catalyst's initial activity.
    Type: Grant
    Filed: November 22, 1991
    Date of Patent: July 5, 1994
    Assignee: Catalytica, Inc.
    Inventors: Michael D. Cooper, Pradip Rao, David L. King, Ronald R. Lopez
  • Patent number: 5276242
    Abstract: In one embodiment of this invention, a process for alkylating C.sub.3 -C.sub.6 alkanes (paraffins) with C.sub.3 -C.sub.6 alkenes (monoolefins) employs a catalyst composition which has been prepared by heating a mixture consisting essentially of aluminum chloride, at least one metal sulfate (CuSO.sub.4, FeSO.sub.4, NiSO.sub.4, MgSO.sub.4, CaSO.sub.4 or combinations thereof), at least one inorganic refractory support material (alumina, silica, silica-alumina, aluminum phosphate, aluminum phosphate/oxide or combinations thereof), and at least one chlorinated hydrocarbon (preferably carbon tetrachloride). In another embodiment of this invention, a process for alkylating C.sub.3 -C.sub.6 alkanes with C.sub.3 -C.sub.6 alkenes employs a catalyst which has been prepared by heating a mixture consisting essentially of aluminum chloride, aluminum phosphate, silica, and at least one chlorinated hydrocarbon (preferably carbon tetrachloride).
    Type: Grant
    Filed: April 20, 1993
    Date of Patent: January 4, 1994
    Assignee: Phillips Petroleum Company
    Inventor: An-hsiang Wu
  • Patent number: 5157197
    Abstract: This invention is a process for the alkylation of isoparaffin with olefins using a catalyst system comprising certain transition aluminas promoted with a Lewis acid (preferably BF.sub.3), and free Lewis acid. The product alkylate is a complex mixture of branched paraffins suitable for use as a high octane blending component for motor fuels.
    Type: Grant
    Filed: May 7, 1991
    Date of Patent: October 20, 1992
    Assignee: Catalytica, Inc.
    Inventors: Michael D. Cooper, David L. King, William A. Sanderson
  • Patent number: 5120895
    Abstract: A process and apparatus are disclosed for acid continuous alkylation of a hydrocarbon-containing feedstream in which the inventory of acid is reduced. The apparatus used combines a reactor, settler and heat exchanger in a single vessel. The acid phase flows out of the reactor only for acid makeup, to account for acid consumption, and regeneration.
    Type: Grant
    Filed: March 4, 1991
    Date of Patent: June 9, 1992
    Assignee: Mobil Oil Corp.
    Inventors: Jonathan E. Child, Tomas R. Melli
  • Patent number: 4992616
    Abstract: The quality of alkylate resulting from the alkylation of isoparaffin with olefin in the presence of an alkylation catalyst comprising a large pore zeolite, e.g., zeolite Beta, and a Lewis acid, e.g., BF.sub.3, is significantly improved by the presence of added water in the alkylation reaction zone.
    Type: Grant
    Filed: October 17, 1989
    Date of Patent: February 12, 1991
    Assignee: Mobil Oil Corporation
    Inventors: Tai-Sheng Chou, Albin Huss, Jr., Clinton R. Kennedy
  • Patent number: 4956518
    Abstract: An improved continuous process for alkylation of isoparaffins with olefins to yield a product which includes a large proportion of highly branced paraffins for making gasoline having improved octane is taught. The improved process comprises contacting isoparaffins and olefins with a composite catalyst comprising a Lewis acid and a non-zeolitic inorganic oxide in the presence of a controlled amount of water. The process results in reduced catalyst aging and obviates environmental problems associated with prior art processes.
    Type: Grant
    Filed: July 11, 1989
    Date of Patent: September 11, 1990
    Assignee: Mobil Oil Corp.
    Inventors: Jonathan E. Child, Tai-Sheng Chou, Albin Huss, Jr., Clinton R. Kennedy, Francis P. Ragonese, Samuel A. Tabak