With Additional Nonhydrocarbon Agent Patents (Class 585/724)
  • Patent number: 11390820
    Abstract: Naphtha boiling range compositions are provided that are formed from crude oils with unexpected combinations of high naphthenes to aromatics weight and/or volume ratio and a low sulfur content. The resulting naphtha boiling range fractions can have a high naphthenes to aromatics weight ratio, a low but substantial content of aromatics, and a low sulfur content. In some aspects, the fractions can be used as fuels and/or fuel blending products after fractionation with minimal further refinery processing. In other aspects, the amount of additional refinery processing, such as hydrotreatment, catalytic reforming and/or isomerization, can be reduced or minimized. By reducing, minimizing, or avoiding the amount of hydroprocessing needed to meet fuel and/or fuel blending product specifications, the fractions derived from the high naphthenes to aromatics ratio and low sulfur crudes can provide fuels and/or fuel blending products having a reduced or minimized carbon intensity.
    Type: Grant
    Filed: May 20, 2021
    Date of Patent: July 19, 2022
    Assignee: ExxonMobil Technology and Engineering Company
    Inventors: Matthew H. Lindner, Scott K. Berkhous, Mike T. Noorman, Gregory K. Lilik, Shifang Luo, Ian J. Laurenzi, Jasmina Poturovic
  • Patent number: 10702858
    Abstract: Some embodiments of the invention include inventive catalysts (e.g., compounds of Formula (I) or (Ia)). Other embodiments include compositions comprising the inventive catalysts. Some embodiments include methods of using the inventive catalysts (e.g., in hydrofluorination of an organic compound). Further embodiments include methods for making the inventive catalysts. Additional embodiments of the invention are also discussed herein.
    Type: Grant
    Filed: December 10, 2018
    Date of Patent: July 7, 2020
    Assignee: UNIVERSITY OF LOUISVILLE RESEARCH FOUNDATION, INC.
    Inventors: Bo Xu, Zhichao Lu, Gerald B. Hammond
  • 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: 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: 8507396
    Abstract: A process for regenerating a used acidic catalyst which has been deactivated by conjunct polymers by removing the conjunct polymers so as to increase the activity of the catalyst is disclosed. Methods for removing the conjunct polymers include addition of a basic reagent and alkylation. The methods are applicable to all acidic catalysts and are described with reference to certain ionic liquid catalysts.
    Type: Grant
    Filed: April 20, 2010
    Date of Patent: August 13, 2013
    Assignee: Chevron U.S.A. Inc.
    Inventors: Saleh Elomari, Thomas V. Harris
  • 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: 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: 8124823
    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 has a NMR branching index greater than 60 and 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.
    Type: Grant
    Filed: February 8, 2011
    Date of Patent: February 28, 2012
    Assignee: Chevron U.S.A. Inc.
    Inventors: Sven Ivar Hommeltoft, Stephen J. Miller, Ajit R. Pradhan
  • 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: 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: 7847142
    Abstract: The regeneration of HF alkylation acid in an alkylation unit is improved by withdrawing a vapor stream from the HF regenerator tower and condensing the stream to form a liquid fraction which is accumulated in a side distillation zone; the collected liquid fraction, comprising HF acid, water and some stripping medium is distilled in a batch or continuous type operation to drive off the HF acid (along with stripping medium) and the vapor is returned to the regenerator-stripper vessel. The distillation of the sidedraw liquid is continued until the composition of the liquid attains the azeotropic value or as near to that value as desired. The azeotrope, comprising water and acid can then be dropped out of the distillation vessel for disposal by neutralization in the conventional way.
    Type: Grant
    Filed: July 27, 2007
    Date of Patent: December 7, 2010
    Assignee: ExxonMobil Research & Engineering Company
    Inventors: Jeffrey M. Fitt, Curtis A. Lawrence, Richard M. Janclaes, Brett Keegan Johnson, Michael W. Boyea, Nicholas Steiner Conley
  • Patent number: 7803979
    Abstract: A method is disclosed for removing water from an alkylation process system using a water removal column to remove water from a re-run column (catalyst regeneration column) overhead stream.
    Type: Grant
    Filed: February 28, 2007
    Date of Patent: September 28, 2010
    Assignee: UOP LLC
    Inventors: Robert M. Gray, Keith W. Hovis
  • Patent number: 7732363
    Abstract: A process for regenerating a used acidic catalyst which has been deactivated by conjunct polymers by removing the conjunct polymers so as to increase the activity of the catalyst is disclosed. Methods for removing the conjunct polymers include hydrogenation, addition of a basic reagent and alkylation. The methods are applicable to all acidic catalysts and are described with reference to certain ionic liquid catalysts.
    Type: Grant
    Filed: December 20, 2005
    Date of Patent: June 8, 2010
    Assignee: Chevron U.S.A. Inc.
    Inventors: Saleh Elomari, Thomas V. Harris
  • Patent number: 7678957
    Abstract: A system and/or process for alkylating hydrocarbons which includes an improved method of safely handling alkylation catalyst is disclosed. The process includes passing the alkylation catalyst from a settler vessel to a catalyst receiving vessel, via a catalyst cooler, for containment therein in the presence of a condensible gas. Also disclosed is a method for controlling the pressure in the catalyst receiving vessel by controlling the rate of removal of vapors.
    Type: Grant
    Filed: March 31, 2005
    Date of Patent: March 16, 2010
    Assignee: UOP LLC
    Inventors: Keith W. Hovis, Khalid Iqbal, Mark R. Cragun
  • 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: 7528289
    Abstract: A novel alkylation catalyst is described which is used in processes for alkylating olefin hydrocarbons with isoparaffin hydrocarbons to produce high octane alkylate products suitable for use as a blending component of gasoline motor fuel. The novel catalyst comprises a mixture of a hydrogen halide and a sulfone. The novel alkylation catalyst is utilized in a novel process for alkylating olefin hydrocarbons with isoparaffin hydrocarbons.
    Type: Grant
    Filed: November 22, 1993
    Date of Patent: May 5, 2009
    Assignee: Phillips Petroleum Company
    Inventors: Ronald G. Abbott, Ralph P. Williams, Marvin M. Johnson, John W. Vanderveen
  • 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: 7446238
    Abstract: A system and/or process for decreasing the level of at least one organic fluoride present in a hydrocarbon phase contained in an alkylation settler by contacting the hydrocarbon phase with an HF containing stream, containing greater than about 80 wt. % and less than about 94 wt. % HF, in the intermediate portion of the settler which contains at least one tray system, with each tray system comprising a perforated tray defining a plurality of perforations and a layer of packing below the perforated tray, are disclosed.
    Type: Grant
    Filed: January 31, 2005
    Date of Patent: November 4, 2008
    Assignee: UOP LLC
    Inventors: Keith W. Hovis, Bruce B. Randolph
  • Patent number: 7371918
    Abstract: A system and/or process for increasing the isobutane to olefin ratio in an alkylation process/system is disclosed. The system and/or process includes provisions for charging a portion of the settler effluent as a feed to at least one reaction zone downflow from the first reaction zone of a multi-zone alkylation reactor along with a portion of the olefin feed to the multi-zone alkylation reactor.
    Type: Grant
    Filed: December 15, 2004
    Date of Patent: May 13, 2008
    Assignee: UOP LLC
    Inventors: Robert M. Gray, Keith W. Hovis
  • Patent number: 7038099
    Abstract: A method of alkylating aliphatic or aromatic hydrocarbons with olefins using solid hydrogen fluoride-equivalent catalysts is described. Preferred catalysts comprise solid polymeric onium polyhydrogen fluoride complexes.
    Type: Grant
    Filed: November 26, 2003
    Date of Patent: May 2, 2006
    Inventor: George A Olah
  • Publication number: 20030130553
    Abstract: A system and/or process for removing water from an alkylation catalyst mixture of an alkylation process is disclosed. The process includes passing an alkylation reaction zone effluent to a settler for separation into a hydrocarbon phase and a catalyst mixture phase; passing at least a portion of the hydrocarbon phase, as a settler effluent stream containing alkylate, water, HF and volatility reducing additive, to a first separator; removing and condensing a first overhead stream from the first separator thereby forming an HF/water stream; passing the HF/water stream to a second separator for separation into a modified HF stream containing HF and volatility reducing additive and into an HF/water azeotrope stream containing HF and water; using the modified HF stream as a part of the alkylation catalyst mixture and; removing water from the system by removing the HF/water azeotrope stream from the second separator.
    Type: Application
    Filed: February 21, 2003
    Publication date: July 10, 2003
    Applicant: ConocoPhillips Company
    Inventors: Bruce B. Randolph, Curtis B. Wood, Martyn E. Pfile
  • Patent number: 6552241
    Abstract: A system and/or process for removing water from an alkylation catalyst mixture of an alkylation process is disclosed. The process includes passing an alkylation reaction zone effluent to a settler for separation into a hydrocarbon phase and a catalyst mixture phase; passing at least a portion of the hydrocarbon phase, as a settler effluent stream containing alkylate, water, HF and volatility reducing additive, to a first separator; removing and condensing a first overhead stream from the first separator thereby forming an HF/water stream; passing the HF/water stream to a second separator for separation into a modified HF stream containing HF and volatility reducing additive and into an HF/water azeotrope stream containing HF and water; using the modified HF stream as a part of the alkylation catalyst mixture and; removing water from the system by removing the HF/water azeotrope stream from the second separator.
    Type: Grant
    Filed: October 31, 2000
    Date of Patent: April 22, 2003
    Assignee: ConocoPhillips Company
    Inventors: Bruce B. Randolph, Curtis B. Wood, Martyn E. Pfile
  • Patent number: 6426441
    Abstract: A system and/or process for decreasing the level of at least one organic fluoride present in a hydrocarbon mixture by first passing the hydrocarbon mixture to an eductor and educting into the hydrocarbon mixture a catalyst comprising a volatility reducing additive and hydrofluoric acid to produce a hydrocarbon-catalyst mixture, permitting the hydrocarbon-catalyst mixture to undergo a phase separation to produce a hydrocarbon phase having a lower concentration of at least one organic fluoride than the hydrocarbon mixture and to produce a catalyst phase, and withdrawing at least a portion of the hydrocarbon phase to thereby form a hydrocarbon product stream, are disclosed. In an alternative embodiment, a system and/or process for controlling the concentration of at least one organic fluoride and/or the RON of the hydrocarbon mixture by adjusting the amount of volatility reducing additive present in the catalyst are disclosed.
    Type: Grant
    Filed: July 10, 2000
    Date of Patent: July 30, 2002
    Assignee: Phillips Petroleum Company
    Inventors: Bruce B. Randolph, Kenneth Charles Hoover
  • Patent number: 6018088
    Abstract: A method is disclosed for producing branched aliphatic ketones in hydrocarbon mixtures from isoalkanes by a superacid catalyzed formylation-rearrangement reaction. The method can be used to simultaneously isomerize, if necessary, and formylate hydrocarbons in complex hydrocarbon mixtures such as refinery streams, alkylate mixtures, and natural gas liquids. Natural gas liquids of low octane number are upgraded and oxygenated by adding to the natural gas liquids or reactively producing in the liquids branched aliphatic ketones.
    Type: Grant
    Filed: April 29, 1998
    Date of Patent: January 25, 2000
    Inventor: George A. Olah
  • Patent number: 5948947
    Abstract: An HF-agent complex, such as HF-pyridine complex where the complexing agent is pyridine, is recovered and recycled from a by-product stream containing ASO, and ASO is rejected from the by-product stream, in an alkylation process using the complex.
    Type: Grant
    Filed: September 10, 1997
    Date of Patent: September 7, 1999
    Assignee: Uop LLC
    Inventor: James F. Himes
  • Patent number: 5877382
    Abstract: Disclosed is a process for removing acid soluble oils, produced as an undesirable by-product of an HF (catalyzed alkylation reaction, from a fluid containing a sulfone compound. The process includes the use of hydrocarbons to remove ASO from the sulfone-containing fluid.
    Type: Grant
    Filed: May 17, 1995
    Date of Patent: March 2, 1999
    Assignee: Phillips Petroleum Company
    Inventor: Alan D. Eastman
  • Patent number: 5811627
    Abstract: Improved acid catalyzed alkylation reactions occur for the addition of a hydrocarbyl reactant to an alkene, by the optimized addition of an oxidizing agent, such as a peroxide, molecular oxygen, ozone, peracid, and one or more of the peroxide, molecular oxygen, ozone, or peracid mixed with at least one material selected from the group consisting of the hydrocarbyl reactant, and the alkene. The hydrocarbyl reactant contains at least one tertiary carbon atom attached to hydrogen, such as isobutane. The alkene is preferably an alkene of at least 2 carbon atoms. Suitable peroxides are found in the group consisting of: tert-butyl peroxyneopentanoate ((CH.sub.3).sub.3 C--O--OCO--C(CH.sub.3).sub.3); acetyl peroxide (CH.sub.3 CO--O--OCOCH.sub.3); di-tert-butyl peroxide ((CH.sub.3).sub.3 C--O--O--C(CH.sub.3).sub.3); hydrogen peroxide (H.sub.2 O.sub.2) and peracids of carboxylic acid having up to 10 carbon atoms, and a general chemical formula C.sub.n H.sub.2n O.sub.3, where n has values in the range 2-10.
    Type: Grant
    Filed: September 13, 1996
    Date of Patent: September 22, 1998
    Inventor: Stanley M. Welsh
  • Patent number: 5792896
    Abstract: An alkylation process for reacting alkylatable hydrocarbons in the presence of a sulfolane and hydrofluoric acid catalyst within a natural circulation reaction and circulation system.
    Type: Grant
    Filed: March 4, 1997
    Date of Patent: August 11, 1998
    Assignee: Phillips Petroleum Company
    Inventors: Bruce B. Randolph, Richard L. Anderson, Harvey D. Hensley
  • Patent number: 5767335
    Abstract: Disclosed is an alkylation process which utilizes a mixture of sulfone and hydrogen fluoride as an alkylation catalyst. The process provides for the removal of light ASO from the alkylation catalyst that accumulates therein as a result of the inability to remove the light ASO produced as a by-product of the alkylation reaction.
    Type: Grant
    Filed: December 18, 1995
    Date of Patent: June 16, 1998
    Assignee: Phillips Petroleum Company
    Inventors: Richard L. Anderson, Keith W. Hovis
  • Patent number: 5763728
    Abstract: An HF-agent complex, such as HF-pyridine complex where the complexing agent is pyridine, is recovered and recycled from a by-product containing stream in an alkylation process using the complex by (a) selectively removing a portion of the HF from the by-product stream to produce an HF-depleted stream having a molar ratio of HF per Lewis base site of the complexing agent of 3:1 to 5:1, (b) separating the resulting HF-depleted stream into a hydrocarbon phase enriched in ASO and an acid phase depleted in ASO and containing a substantial portion of the complex, and (c) recycling the acid phase to the hydrocarbon alkylation step.
    Type: Grant
    Filed: September 25, 1995
    Date of Patent: June 9, 1998
    Assignee: UOP
    Inventors: Joseph A. Kocal, Harold U. Hammershaimb, Robert J. Cornish, Terry L. Marker, James F. Himes
  • Patent number: 5759937
    Abstract: Disclosed is an alkylation process which utilizes a mixture of sulfone and hydrogen fluoride as an alkylation catalyst. The process provides for the removal of ASO and water from the alkylation catalyst that accumulates therein while minimizing the loss of sulfone and HF with the ASO and water removed.
    Type: Grant
    Filed: October 2, 1996
    Date of Patent: June 2, 1998
    Assignee: Phillips Petroleum Company
    Inventors: Keith W. Hovis, Richard L. Anderson
  • Patent number: 5723715
    Abstract: A novel alkylation catalyst is described which is used in processes for alkylating olefin hydrocarbons with isoparaffin hydrocarbons to produce high octane alkylate products suitable for use as a blending component of gasoline motor fuel. The novel catalyst comprises a mixture of a hydrogen halide, a sulfone and a promoter. The novel alkylation catalyst is utilized in a novel process for alkylating olefin hydrocarbons with isoparaffin hydrocarbons.
    Type: Grant
    Filed: May 30, 1995
    Date of Patent: March 3, 1998
    Inventors: Bruce B. Randolph, Ronald G. Abbott
  • Patent number: 5689030
    Abstract: A method for prolonging the life of a defluorinator material contained within an alkylation process product stream defluorination zone used to remove organic fluorides from a product stream produced by an alkylation process that utilizes an alkylation catalyst containing HF and sulfone. The life of the defluorinator material is extended by reducing the amount of organic fluorides produced in the alkylation process through the addition of trifluoromethanesulfonic acid to the HF/sulfone alkylation catalyst.
    Type: Grant
    Filed: March 6, 1996
    Date of Patent: November 18, 1997
    Assignee: Phillips Petroleum Company
    Inventor: Bruce B. Randolph
  • Patent number: 5663474
    Abstract: This invention relates to catalysts for alkylation reactions and their preparation. More particularly, the invention relates to an alkylation process using a hydrogen fluoride-containing alkylation catalyst, which catalyst may be safely and easily handled, transported, and stored.
    Type: Grant
    Filed: March 7, 1996
    Date of Patent: September 2, 1997
    Assignee: AlliedSignal Inc.
    Inventors: Hang Thanh Pham, Robert Pratt, Charles Lewis Redmon, John James Thompson, Michael Van Der Puy, Rajiv Ratna Singh, William James Hague, Harold John Kieta, Matthew Hermes Luly, Jeffrey Warren McKown
  • Patent number: 5654251
    Abstract: A novel alkylation catalyst is described which is used in processes for alkylating olefin hydrocarbons with isoparaffin hydrocarbons to produce high octane alkylate products suitable for use as a blending component of gasoline motor fuel. The novel catalyst comprises a mixture of a hydrogen halide and a sulfone. The novel alkylation catalyst is utilized in a novel process for alkylating olefin hydrocarbons with isoparaffin hydrocarbons.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: August 5, 1997
    Assignee: Phillips Petroleum Company
    Inventors: Ronald G. Abbott, Ralph P. Williams, Marvin M. Johnson, John W. Vanderveen
  • Patent number: 5648588
    Abstract: Disclosed is a process for separating sulfone and hydrogen fluoride from hydrocarbon streams containing a concentration of such compounds. An extraction solvent laden with sulfone and HF is contacted with a reversible base in order to remove the HF therefrom. The thus-treated extract stream is separated into a water stream that can be reused as the water extractant and a sulfone stream that is suitably free of HF.
    Type: Grant
    Filed: December 8, 1995
    Date of Patent: July 15, 1997
    Assignee: Phillips Petroleum Company
    Inventors: Richard L. Anderson, Bruce B. Randolph
  • Patent number: 5648587
    Abstract: Disclosed is a process for separating sulfone from a hydrocarbon stream containing a small concentration sulfone by using water as an extraction solvent. The extraction solvent, laden with the removed sulfone, is further processed to separate the extraction solvent and water to thereby produce a sulfone product suitable for reused in an alkylation process or for sale as a dry sulfone end-product.
    Type: Grant
    Filed: December 4, 1995
    Date of Patent: July 15, 1997
    Assignee: Phillips Petroleum Company
    Inventors: Keith W. Hovis, Richard L. Anderson
  • Patent number: 5646086
    Abstract: 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), said support having been impregnated with said acidic phase and said support prior to impregnation having a total pore volume of 0.1-0.6 cm.sup.3 /g, said catalyst being essentially constituted by particles with an average diameter of between 0.1 and 30 .mu.m, 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.is suitable for the catalytic alkylation of isobutane and/or isopentane in the presence of at least one olefin containing 2 to 6 carbon atoms per molecule, preferably 3 to 6 carbon atoms per molecule.
    Type: Grant
    Filed: May 4, 1995
    Date of Patent: July 8, 1997
    Assignee: Institut Francais Du Petrole
    Inventors: Eric Benazzi, Jean-Fran.cedilla.ois Joly, Christian Marcilly
  • Patent number: 5639932
    Abstract: A novel alkylation catalyst is described which is used in processes for alkylating olefin hydrocarbons with isoparaffin hydrocarbons to produce high octane alkylate products suitable for use as blending components of gasoline motor fuel. The novel catalyst comprises a mixture of a hydrogen halide, a sulfone and water and has suitable corrosion properties which permit its utilization in alkylation process systems. The novel alkylation catalyst is utilized in a novel process for alkylating olefin hydrocarbons with isoparaffin hydrocarbons.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: June 17, 1997
    Assignee: Phillips Petroleum Company
    Inventors: Ronald G. Abbott, Bruce B. Randolph
  • Patent number: 5629466
    Abstract: A method for removing from a gasoline pool and alkylating amylenes in the presence of a hydrogen fluoride catalyst while suppressing or inhibiting the production of synthetic isopentane during the alkylation of such amylenes by the addition of sulfone to the hydrogen fluoride catalyst.
    Type: Grant
    Filed: March 23, 1995
    Date of Patent: May 13, 1997
    Assignee: Phillips Petroleum Company
    Inventor: Bruce B. Randolph
  • 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
  • Patent number: 5569807
    Abstract: A novel alkylation catalyst is described which is used in processes for alkylating olefin hydrocarbons with isoparaffin hydrocarbons to produce high octane alkylate products suitable for use as blending components of gasoline motor fuel. The novel catalyst comprises a mixture of a hydrogen halide, a sulfone and water and has suitable corrosion properties which permit its utilization in alkylation process systems. The novel alkylation catalyst is utilized in a novel process for alkylating olefin hydrocarbons with isoparaffin hydrocarbons.
    Type: Grant
    Filed: May 1, 1992
    Date of Patent: October 29, 1996
    Assignee: Phillips Petroleum Company
    Inventors: Ronald G. Abbott, Bruce B. Randolph
  • Patent number: 5557028
    Abstract: Improved acid catalyzed alkylation reactions occur for the addition of a hydrocarbyl reactant to an alkene, by the optimized addition of an oxidizing agent, such as a peroxide, molecular oxygen, ozone, peracid, and one or more of the peroxide, molecular oxygen, ozone, or peracid mixed with at least one material selected from the group consisting of the hydrocarbyl reactant, and the alkene. The hydrocarbyl species contains at least one tertiary carbon atom attached to hydrogen, such as isobutane. The alkene is preferably 1- or 2-butene. Suitable peroxides are found in the group consisting of: tert-butyl peroxyneopentanoate ((CH.sub.3).sub.3 C--O--OCO--C(CH.sub.3).sub.3); acetyl peroxide (CH.sub.3 CO--O--O--COCH.sub.3); di-tert-butyl peroxide ((CH.sub.3).sub.3 C--O--O--C(CH.sub.3).sub.3); hydrogen peroxide (H.sub.2 O.sub.2) and peracids of carboxylic acid having up to 10 carbon atoms, and a general chemical formula C.sub.n H.sub.2n O.sub.3, where n has values in the range 2-10.
    Type: Grant
    Filed: March 31, 1995
    Date of Patent: September 17, 1996
    Inventor: Stanely M. Welsh