Al Halide Patents (Class 585/727)
  • Patent number: 11083761
    Abstract: This invention provides for a dry preserved formulation of Lactobacillus suitable for administration to people as a pro-biotic or live biotherapeutic treatment where the formulation is stable, has high potency, and contains no animal-derived excipients.
    Type: Grant
    Filed: March 20, 2020
    Date of Patent: August 10, 2021
    Assignee: Osel, Inc.
    Inventors: Thomas P. Parks, Angela Marcobal
  • 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: 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: 8487154
    Abstract: A process comprising adjusting a level of conjunct polymers in an ionic liquid catalyst between a low level that favors production of C5+ products boiling at 137.8° C. or below and a higher level that favors production of both C5+ products boiling at 137.8° C. or below and C5+ products boiling above 137.8° C.; wherein the adjusting is done in response to market demand. A process unit, comprising a reactor that operates with an ionic liquid catalyst comprising a low level or a higher level of conjunct polymers, and the alkylation reactor is switched between operating with the low and the higher levels in response to market demand. A process unit, comprising a reactor that operates in an alkylate mode and a distillate mode, and a catalyst regenerator that operates with varying severity to adjust the level of conjunct polymers in response to demand for gasoline or distillate.
    Type: Grant
    Filed: March 17, 2010
    Date of Patent: July 16, 2013
    Assignee: Chevron U.S.A. Inc.
    Inventors: Hye-Kyung Timken, Shawn Winter, Howard S. Lacheen, Sven Ivar Hommeltoft
  • Patent number: 8461408
    Abstract: A method for alkylating a hydrocarbon comprising at least one isoparaffin and at least one olefin that includes introducing a liquid catalyst and the hydrocarbon into a high shear device; processing the liquid catalyst and the hydrocarbon in the high shear device to form an emulsion comprising droplets of hydrocarbon dispersed in the liquid catalyst; introducing the emulsion into a vessel operating under suitable alkylation conditions whereby at least a portion of the isoparaffin is alkylated with the olefin to form alkylate, wherein suitable alkylation conditions comprise a bulk reaction temperature of from about 38° C. to about 90° C. and a bulk reaction pressure in the range of from about 1379 kPa to about 34 MPa; and removing a product stream comprising alkylate from the vessel.
    Type: Grant
    Filed: August 15, 2012
    Date of Patent: June 11, 2013
    Assignee: H R D Coporation
    Inventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
  • Patent number: 8455708
    Abstract: A process for producing hydrocarbon products, comprising: a) operating a process unit in an alkylate mode wherein greater than 50 wt % of a C5+ hydrocarbon stream from the process unit boils at 137.8° C. or below, b) adjusting one or more process conditions in the process unit, and c) after the adjusting step, operating the process unit in a distillate mode wherein greater than 50 wt % of the C5+ hydrocarbon stream from the process unit boils above 137.8° C. Also, a process unit, comprising: a) an alkylation reactor; and b) a control system that enables the alkylation reactor to be operated in the alkylate mode and in the distillate mode; wherein the alkylation reactor can switch back and forth from operating in the alkylate mode to the distillate mode.
    Type: Grant
    Filed: March 17, 2010
    Date of Patent: June 4, 2013
    Assignee: Chevron U.S.A. Inc.
    Inventors: Hye-Kyung Timken, Shawn Winter, Howard S. Lacheen, Sven Ivar Hommeltoft
  • 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
  • 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: 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: 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: 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
  • Publication number: 20110184219
    Abstract: A process for determining ionic liquid catalyst deactivation including (a) collecting at least one sample of an ionic liquid catalyst; (b) hydrolyzing the at least one sample to provide at least one hydrolyzed sample; (c) titrating the at least one hydrolyzed sample with a basic reagent to determine a volume of the basic reagent necessary to neutralize a Lewis acid species of the ionic liquid catalyst; and (d) calculating the acid content of the at least one sample from the volume of basic reagent determined in step (c) is described. Processes incorporating such a process for determining ionic liquid catalyst deactivation are also described. These processes are an alkylation process, a process for controlling ionic liquid catalyst activity in a reaction producing by-product conjunct polymers, and a continuous process for maintaining the acid content of an ionic liquid catalyst at a target acid content in a reaction producing by-product conjunct polymers.
    Type: Application
    Filed: January 18, 2011
    Publication date: July 28, 2011
    Inventors: Hye Kyung Timken, Annie T. Pathiparampil
  • 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: 20110105811
    Abstract: A process to produce an alkylate distillate blending component in one embodiment comprising: providing at least one olefinic C5+ product which was produced by conversion of synthesis gas in a Fischer Tropsch process; and alkylating the olefinic C5+ product in the presence of an acidic ionic liquid alkylation catalyst with hydrocarbons selected from the group consisting of isoparaffins, cycloparaffins, and their mixtures to form an alkylate distillate blending component is described.
    Type: Application
    Filed: October 30, 2009
    Publication date: May 5, 2011
    Inventors: Dennis J. O'Rear, Sven Ivar Hommeltoft, Steve S. Mathur, Jerome F. Mayor, Hye-Kyung Timken
  • 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: 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: 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: 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: 7750197
    Abstract: The invention relates to a process for alkylating a hydrocarbon feed which comprises contacting the hydrocarbon feed to be alkylated with an alkylation agent in the presence of a catalyst comprising a solid acid, a hydrogenation metal, and 1.5-6 wt % of water, measured as the loss on ignition at 600° C. The presence of 1.5-6 wt % of water results in a higher activity and a higher alkylate quality compared with a comparable but drier catalyst.
    Type: Grant
    Filed: January 26, 2005
    Date of Patent: July 6, 2010
    Assignee: Albemarle Netherlands B.V.
    Inventors: Emanuel Hermanus Van Broekhoven, Jan Sant, Stephan Zuijdendorp, Niels Winkler
  • 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: 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: 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: 7572944
    Abstract: A process for making and a composition of a superior lubricant or lubricant component by the oligomerization of a mixture comprising olefins and isoparaffins to produce an alkylated (“capped”) olefin oligomer having a very high VI and a low cloud point. The process preferably uses 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 11, 2009
    Assignee: Chevron U.S.A. Inc.
    Inventors: Saleh Elomari, Russell Krug
  • Patent number: 7572943
    Abstract: A process and method for making a superior lubricant or distillate fuel component by the oligomerization of a mixture comprising olefins to form an oligomer and the alkylation of the oligomer with isoparaffins to produce an alkylated (“capped”) olefin oligomer preferably 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 11, 2009
    Assignee: Chevron U.S.A. Inc.
    Inventors: Saleh Elomari, Russell Krug, Thomas V. Harris, Michael S. Driver
  • 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: 7294420
    Abstract: A method of producing hydrogen for a fuel cell from a hydrocarbon fuel composition, by providing a hydrocarbon fuel composition, which is obtained by contacting a liquid hydrocarbon feed comprising an alkylating agent with an acidic catalyst, under conditions effective to alkylate at least a portion of the hydrocarbon feed; converting the hydrocarbon fuel composition into hydrogen; and optionally, introducing the hydrogen produced into a fuel cell. In a preferred embodiment the liquid hydrocarbon feed further comprises sulphur-containing impurities, at least a portion of which are alkylated during the alkylation step.
    Type: Grant
    Filed: August 28, 2002
    Date of Patent: November 13, 2007
    Assignee: BP P.L.C.
    Inventor: Michael Graham Hodges
  • Publication number: 20040082827
    Abstract: A process for converting n-butane and ethylene to a product by contact with a catalyst containing a Group VIII metal, a halogen, and a support, in the presence of a Lewis Acid, and optionally in the presence of hydrogen, is disclosed.
    Type: Application
    Filed: October 25, 2002
    Publication date: April 29, 2004
    Inventor: Bruce B. Randolph
  • Patent number: 6392114
    Abstract: An alkylating agent alkylates an alkylation substrate in a solid catalyst alkylation process in which an alkylation reactor produces a reaction effluent and a catalyst regeneration zone produces a hydrogen-containing regeneration effluent. The alkylation effluent passes to an alkylate fractionation zone, while the regeneration effluent passes to a hydrogen fractionation zone to remove hydrogen and produce a hydrogen-depleted stream that passes to the alkylate fractionation zone. The process recycles hydrogen, and can recycle halogen-containing species as well, within the process while preventing admixture of hydrogen with the alkylating agent. This invention is particularly applicable to alkylation processes that use an olefinic alkylating agent.
    Type: Grant
    Filed: December 30, 1999
    Date of Patent: May 21, 2002
    Assignee: UOP LLC
    Inventors: Dale J. Shields, Paul A. Sechrist
  • Patent number: 6337297
    Abstract: A catalyst for trimerization of ethylene is disclosed which comprises (a) a chromium complex having a neutral multidentate ligand having a tripod structure, represented by the formula, ACrJnQ3-n wherein A is a neutral multidentate ligand having a tripod structure, J is a carbonyl ligand or halogen, n is an integer of 0-3, and Q is at least one member selected from hydrogen, a C1-C10 hydrocarbon group, a C1-C10 carboxylate group, a C3-C10 diketonato group, an amide group, an imide group, an C1-C10 alkoxide group, a C1-C10 thioalkoxide group, an C6-C15 arene ligand, an C2-C10 alkene ligand, an C2-C15 alkyne ligand, an amine ligand, an imine ligand, an isonitrile ligand, a phosphine ligand, a phosphine oxide ligand, a phosphite ligand, an ether ligand, a sulfide ligand, a sulfone ligand and a sulfoxide ligand, and (b) a metal alkyl compound.
    Type: Grant
    Filed: December 9, 1999
    Date of Patent: January 8, 2002
    Assignee: Tosoh Corporation
    Inventors: Hideyuki Mimura, Motohiro Oguri, Toshihide Yamamoto, Hideyuki Murakita, Hisanori Okada, Toru Yoshida
  • 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: 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: 5600055
    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: ##STR1## wherein a 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%; ##STR2## C is selected from the group consisting of: ##STR3## (III) combinations thereof. 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 alkyl group, C.sub.3 -C.sub.24 cycloalkyl, C.sub.6 -C.sub.18 aryl, or C.sub.7 -C.sub.30 alkylaryl;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.4 represents C.sub.1 -C.sub.24 alkyl, C.sub.3 -C.
    Type: Grant
    Filed: May 8, 1995
    Date of Patent: February 4, 1997
    Assignee: Exxon Chemical Patents Inc
    Inventors: Tze-Chiang Chung, Frank J.-Y. Chen, Jon E. Stanat, Alok Kumar