With Added Oxygen Containing Organic Compound Patents (Class 208/204)
  • Patent number: 10626333
    Abstract: A process and apparatus for sweetening a hydrocarbon stream. The apparatus includes two vessels. In a first extraction vessel, caustic removes mercaptans from the hydrocarbon stream. In a second oxidation vessel, the mercaptans in the rich caustic are converted in disulfides. The lean caustic and disulfides are passed back to the first extraction vessel in which the disulfides are separated into the sweetened hydrocarbon phase. The second vessel may receive a wash oil, such as the sweetened hydrocarbon phase, to remove disulfides from a vented gas stream.
    Type: Grant
    Filed: June 29, 2016
    Date of Patent: April 21, 2020
    Assignee: UOP LLC
    Inventors: July S. Maglente, Luigi Laricchia, Jonathan A. Tertel
  • Patent number: 10550337
    Abstract: A treatment process for remediating a contaminated liquid containing more than 5 ppm hydrogen sulfide (H2S) and substantially without formation of precipitate, includes steps of steps of adding an aqueous solution containing at least one hydroxide compound at a collective concentration of 35-55 wt % to the contaminated liquid to achieve a concentration of 125-5000 ppm of the hydroxide compounds in the contaminated liquid, adding at least one organic acid and to the liquid to achieve a concentration of 0.01-10 ppm in the contaminated liquid, and dispersing the aqueous solution and the at least one organic acid in the contaminated liquid and allowing the aqueous solution and the at least one organic acid to react with the contaminated liquid for a period of time until a concentration of hydrogen sulfide in the contaminated liquid is reduced to ?5 ppm.
    Type: Grant
    Filed: January 22, 2019
    Date of Patent: February 4, 2020
    Assignee: GAPS Technology, LLC.
    Inventors: Cliffton Lee Roe, Linda Schweitzer
  • Patent number: 10336949
    Abstract: A process for the removal of residual sulfur compounds from rich liquid caustic is disclosed where a single column containing two reaction zones catalytically oxidizes mercaptans to disulfide oils. The second reaction zone utilizes a bundle of vertical hanging fibers and is maintained as a gas continuous phase comprising from about 20% to about 100% by volume vapor. This process is especially useful as part of a hydrocarbon desulfurization process flow scheme.
    Type: Grant
    Filed: July 2, 2018
    Date of Patent: July 2, 2019
    Assignee: MERICHEM COMPANY
    Inventor: Jeffrey Bruce Gomach
  • Patent number: 10059889
    Abstract: A process for the removal of residual sulfur compounds from rich liquid caustic is disclosed where a single column containing two reaction zones catalytically oxidizes mercaptans to disulfide oils. The second reaction zone utilizes a bundle of vertical hanging fibers and is maintained as a gas continuous phase comprising from about 20% to about 100% by volume vapor. This process is especially useful as part of a hydrocarbon desulfurization process flow scheme.
    Type: Grant
    Filed: June 22, 2016
    Date of Patent: August 28, 2018
    Assignee: MERICHEM COMPANY
    Inventor: Jeffrey Bruce Gomach
  • Patent number: 9719030
    Abstract: Disclosed herein are scavenging compounds and compositions useful in applications relating to the production, transportation, storage, and separation of crude oil and natural gas. Also disclosed herein are methods of using the compounds and compositions as scavengers, particularly in applications relating to the production, transportation, storage, and separation of crude oil and natural gas.
    Type: Grant
    Filed: June 25, 2014
    Date of Patent: August 1, 2017
    Assignee: Ecolab USA Inc.
    Inventors: Jennifer L. Sorrells, Nestor U. Soriano, Jr.
  • Patent number: 9719029
    Abstract: An oxidative desulfurization process is provided in which gaseous oxidant required for oxidative desulfurization reactions is dissolved in the feedstock upstream of the oxidative desulfurization reactor. Gaseous oxidant is mixed with a generally liquid phase feedstock (and in certain embodiment peroxide precursors are also mixed) in a mixing zone under conditions effective to dissolve the gaseous oxidant in the liquid feedstock. The gaseous oxidant dissolved in the hydrocarbon feedstock provides a gaseous oxidant-enhanced feedstock which is charged to the oxidative desulfurization reaction zone thereby permitting substantially liquid phase operation.
    Type: Grant
    Filed: November 11, 2013
    Date of Patent: August 1, 2017
    Assignee: Saudi Arabian Oil Company
    Inventors: Omer Refa Koseoglu, Abdennour Bourane
  • Patent number: 9708547
    Abstract: Hydrogen sulfide (H2S) and/or mercaptan scavengers are chemicals that remove H2S and/or mercaptans from gas, oil and water. Water-based formulations may be made and used employing scavenging compounds having the formulae: wherein each R1, R2, R3, and R4 are the same or different and are selected from the group consisting of hydrogen, an alkyl, an alkenyl, an aryl, an acyl, a halogen, a hydroxyl, a nitro, an alkyl ester, an aryl ester, an alkyl ether, an aryl ether, a hydroxymethyl, an anhydride group, an amino, and a sulfide. In one non-limiting embodiment the compounds (A) and (B) do not contain nitrogen atoms. Water-based formulations, such as those using a protic solvent with the above compounds, work well as H2S scavengers.
    Type: Grant
    Filed: June 29, 2011
    Date of Patent: July 18, 2017
    Assignee: Baker Hughes Incorporated
    Inventors: Sunder Ramachandran, Vladimir Jovancicevic, Ying H. Tsang, Michael P. Squicciarini, Philippe Prince, Jianzhong Yang, Kyle C. Cattanach
  • Patent number: 9701909
    Abstract: Carbon dioxide is used as a solvent to extract bitumen from oil sands in an anhydrous process that is compatible with existing procedures for upgrading bitumen. The process should provide high yields and meet environmental concerns.
    Type: Grant
    Filed: December 27, 2012
    Date of Patent: July 11, 2017
    Inventor: John E. Stauffer, II
  • Publication number: 20150048006
    Abstract: In a catalytic treatment process, mercaptans in sour hydrocarbon are oxidized to disulfide oils using an aqueous treatment solution containing a chelated polyvalent metal catalyst, alkali metal hydroxide, and the alkali metal salt of at least one alcohol in a non-dispersive mixing apparatus wherein an upgraded hydrocarbon containing the disulfide oils is produced.
    Type: Application
    Filed: November 3, 2014
    Publication date: February 19, 2015
    Inventors: Tiejun Zhang, K. Michael Hardy, V. Keith Turner, Ignacio C. Bincaz, Tom Varadi
  • Publication number: 20140284250
    Abstract: Process of extracting sulphur-containing compounds from a hydrocarbon cut of the gasoline or LPG type by liquid-liquid extraction with a soda solution employing a unit (2) for pretreatment of the feedstock to be treated placed upstream of the extraction unit (4), the soda being introduced into the extraction column (4) in the form of two circuits operating either in parallel, or in series.
    Type: Application
    Filed: October 16, 2012
    Publication date: September 25, 2014
    Applicant: IFP ENERGIES NOUVELLES
    Inventors: Frederic Augier, Arnaud Baudot, Jeremy Gazarian, Damien Leinekugel Le Cocq
  • Publication number: 20110163008
    Abstract: In a catalytic treatment process, mercaptans in sour hydrocarbon are oxidized to disulfide oils using an aqueous treatment solution containing a chelated polyvalent metal catalyst, alkali metal hydroxide, and the alkali metal salt of at least one alcohol in a non-dispersive mixing apparatus wherein an upgraded hydrocarbon containing the disulfide oils is produced.
    Type: Application
    Filed: January 31, 2011
    Publication date: July 7, 2011
    Applicant: MERICHEM COMPANY
    Inventors: Tiejun Zhang, K. Michael Hardy, V. Keith Turner, Ignacio C. Bincaz, Tom Varadi
  • Publication number: 20110127194
    Abstract: In a catalytic treatment process, mercaptans in sour hydrocarbon are oxidized to disulfide oils using an aqueous treatment solution containing a chelated polyvalent metal catalyst, alkali metal hydroxide, and the alkali metal salt of at least one alcohol in a non-dispersive mixing apparatus wherein an upgraded hydrocarbon containing the disulfide oils is produced.
    Type: Application
    Filed: November 30, 2009
    Publication date: June 2, 2011
    Inventors: Tiejun Zhang, K. Michael Hardy, V. Keith Turner, Ignacio C. Bincaz, Tom Varadi
  • Patent number: 7244352
    Abstract: A process for producing a naphtha having a decreased amount of sulfur by selective hydroprocessing a petroleum feedstream comprising cracked naphtha to reduce its sulfur content with minimum loss of octane. The reduced sulfur naphtha stream contains mercaptan sulfur reversion products that are removed preferably by use of an aqueous base solution containing a catalytically effective amount of a phase transfer catalyst.
    Type: Grant
    Filed: February 7, 2003
    Date of Patent: July 17, 2007
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Thomas R. Halbert, Craig A. McKnight, John P. Greeley, Bruce R. Cook, Garland B. Brignac, Mark A. Greaney, Robert C. Welch
  • Patent number: 6755964
    Abstract: A process for fixed bed sweetening of petroleum distillates using halogenating metal phthalocyanine as a catalyst comprising impregnating the catalyst on activated charcoal bed by circulating alcoholic alkaline solution of the catalyst through charcoal bed till colorless bed solution is obtained in the effluent, passing the petroleum distillate through the said catalyst loaded charcoal bed along with air or oxygen at a temperature and pressure with liquid hourly space velocity with continuous or intermittent injection of alkali solution such as sodium hydroxide of concentration to obtain the desired low mercaptan level petroleum distillates. The alkaline solution used is selected from methanolic and ethanolic solution of sodium hydroxide. The halogenated metal phthalocyanine catalyst used is selected from dichloro cobalt phthalocyanine and dibromo cobalt phthalocyanine. The petroleum fraction used is selected from diesel, kerosene and FCC gasoline.
    Type: Grant
    Filed: March 13, 2001
    Date of Patent: June 29, 2004
    Assignee: Council of Scientific & Industrial Research
    Inventors: Brij Bahadur Agrawal, Som Nath Puri, Gautam Das, Bir Sain, Bhagwati Prasad Balodi, Sunil Kumar, Anil Kumar, Pushpa Gupta, Jai Prakash, Onkar Singh Tyagi, Turuga Sundara Rama Prasada Rao, Gur Pratap Rai
  • Patent number: 6709639
    Abstract: An apparatus for the purification of catalytic cracking gasolines containing dienic and/or acetylenic impurities, and mercaptans, said apparatus comprising at least one selective hydrogenation reactor 3 containing at least one fixed catalyst bed, and having at least one line 1 for introducing a feed, at least one effluent outlet line, and a line supplying hydrogen to the reactor, said reactor being followed by at least one stabilization drum 4 connected to said effluent outlet line, the drum having at least one gas outlet line 5 and at least one stabilized effluent outlet line, and said effluent passing into at least one sweetening reactor 8 comprising at least one effluent inlet line 6 and at least one effluent outlet line, said reactor having close thereto at least one oxidizing agent supply line, said apparatus also comprising at least one drum 9 for degassing the effluent from the sweetening reactor 8, said drum 9 having at least one gas outlet line and at least one outlet line 11 for dedienized, stabiliz
    Type: Grant
    Filed: March 9, 2000
    Date of Patent: March 23, 2004
    Assignee: Institut Francais du Petrole
    Inventors: Thierry Chapus, Blaise Didillon, Christian Marcilly, Charles Cameron
  • Publication number: 20040026297
    Abstract: A catalyst is intended for the oxidative demercaptanization (sweetening) of hydrocarbons compositions including petroleum, petroleum distillates, gasolines, kerosenes, jet fuels, diesel fuels and heating oils, natural-gas liquids, etc. It may be used in a fixed-bed or fluidized-bed process. A catalyst consist of an active part and an inert component. The active part contains an oxide of a transition metal of Groups Ib, V-VIIb of the Periodic Table, either Ni or Co oxide, or mixture of oxides of the indicated elements, and transition metal salts, and nitrogen-containing organics. The inert component is an oxide of an element of Groups IIa, III, IV, or Fe oxide, or chemical compound including not less than 95% oxides of indicated elements, or mixture of the above compounds.
    Type: Application
    Filed: June 20, 2003
    Publication date: February 12, 2004
    Inventors: Alexei Konovalov, Vladimir Smirnov, Vladimir Konovalov, Irina Tarkhanova
  • Publication number: 20030188992
    Abstract: A process for decreasing the amount of sulfur in a petroleum stream.
    Type: Application
    Filed: February 7, 2003
    Publication date: October 9, 2003
    Inventors: Thomas R. Halbert, Craig A. McKnight, John P. Greeley, Bruce R. Cook, Garland B. Brignac, Mark A. Greaney, Robert C. Welch
  • Patent number: 6565740
    Abstract: The present invention related to a process for sweetening of LPG light petroleum distillates by liquid liquid extraction using metal phtalocyanine sulphonamide catalyst which comprises extracting the mercaptanes contain in LPG, light petroleum distillate like pentanes, light straight run naphtha by liquid-liquid extraction using an aqueous or alcoholic solution of alkali metal hydroxide of concentration ranging between 1 wt % to 50 wt % in the presence of a metal phthalocyanine sulphonamide catalyst in the concentration ranging from 5-4000 ppmw, at a temperature ranging from 10° C. to 80° C. at a pressure ranging from 1 kg/cm2-50 kg/cm2 in a continuous or batch manner, converting the mercaptanes present in above said extract into corresponding disulphides by passing air, oxygen or any oxygen containing gas at the above same temperature and pressure, regenerating the alkali solution containing catalyst for recycling by separating the upper layer of disulphides from said alkali solution of catalyst.
    Type: Grant
    Filed: March 26, 2001
    Date of Patent: May 20, 2003
    Assignee: Council of Scientific and Industrial Research
    Inventors: Bir Sain, Som Nath Puri, Gautam Das, Bhagwati Prasad Balodi, Sunil Kumar, Anil Kumar, Virendra Kumar Kapoor, Virendra Kumar Bhatia, Turuga Sundara Rama Prasada Rao, Gur Pratap Rai
  • Patent number: 6547959
    Abstract: A method for treating compounds which contain reactive sulfur is disclosed, wherein the treatment produces compounds which contain sulfur in a non reactive form. The method is based on the use of an oxidizing compound selected from the group consisting of water soluble inorganic persulfates, water soluble inorganic and organic adducts of hydrogen peroxide and mixtures thereof. The method is particularly useful in preventing stress corrosion cracking of stainless steel and in preventing auto-ignition of pyrophoric iron sulfide.
    Type: Grant
    Filed: September 19, 2000
    Date of Patent: April 15, 2003
    Assignee: United Laboratories International, LLC
    Inventor: Jack G. Frost
  • Publication number: 20030042175
    Abstract: The invention relates to a process for the production of gasoline with a low sulfur content that comprises at least one selective hydrogenation of diolefins, optionally at least one stage for transformation, preferably to increase their weight, for light sulfur-containing compounds that are present in the gasoline, at least one fractionation of the gasoline that is obtained into at least two fractions: light gasoline and heavy gasoline, then optionally a stage for transformation, preferably for alkylation or adsorption, of sulfur-containing compounds and a desulfurization treatment in a stage of at least a portion of the heavy fraction.
    Type: Application
    Filed: March 12, 2002
    Publication date: March 6, 2003
    Applicant: Institut Francais du Petrole
    Inventors: Quentin Debuisschert, Denis Uzio, Jean-Luc Nocca, Florent Picard
  • Patent number: 6488840
    Abstract: This invention relates to reducing the amount of thiols (mercaptans) in petroleum streams, specifically, mercaptans above the five carbon molecular weight range.
    Type: Grant
    Filed: April 18, 2000
    Date of Patent: December 3, 2002
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Mark Alan Greaney, Michael Charles Kerby, Roby Bearden, Jr.
  • Patent number: 6447673
    Abstract: A hydrofining process in which a sulfur- and hydrocarbon-containing processing stream is supplied to a multi-stage hydrotreating reactor incorporating separate stages of cobalt molybdenum catalysts. Hydrogen may be supplied concurrently or counter-currently with the hydrocarbon-containing processing stream. The processing stream is passed into contact with an initial catalyst stage comprising a cobalt molybdenum desulfurization catalyst present in a minor amount of the total composite amount of catalysts within the reactor. Thereafter the processing stream is passed through a subsequent catalyst stage comprising a major amount of cobalt molybdenum hydrocracking catalyst. The effluent stream having a reduced sulfur content is then withdrawn from the hydrotreating reactor. The initial and subsequent catalyst stages are separated by an intervening sector within the reactor containing an inert particulate refractory material, specifically silica particles generally spheroidal in shape.
    Type: Grant
    Filed: March 12, 2001
    Date of Patent: September 10, 2002
    Assignee: Fina Technology, Inc.
    Inventors: Merry Holli Garrett Cordera, Charles Allen Comeaux, Koenraad Jacques Herrebout, Joe David Hunter
  • Publication number: 20020117425
    Abstract: A process for reducing content of sulphur compounds and polyaromatic hydrocarbons in a hydrocarbon feed having a boiling range between 120° C. and 450° C., which process comprises in combination contacting the feed and hydrogen over a hydrotreating catalyst and hydrotreating feed at hydrotreating conditions, cooling the effluent consisting of hydrocarbon, polyaromatic hydrocarbons, hydrogen sulphide and hydrogen-rich gas from the hydrotreating reactor, contacting said effluent and hydrogen gas over a hydrotreating catalyst in a post treat reactor at a temperature appropriate to lower the polyaromatic hydrocarbon content.
    Type: Application
    Filed: January 24, 2001
    Publication date: August 29, 2002
    Inventors: Kim Gr?oslash;n Knudsen, Barry H. Cooper, Thomas Tippett
  • Patent number: 6187173
    Abstract: A process and apparatus for treating raw gasoline from catalytic cracking to obtain gasoline with the qualities required for use as motor fuel comprises selective hydrogenation followed by stabilization and optional cooling of the effluent, then sweetening followed by degassing to obtain a dedienized, stabilized and sweetened gasoline. The hydrogenation catalyst preferably comprises 0.1-1% of palladium deposited on a support, sweetening is preferably carried out on a solid catalyst containing an aluminosilicate of an alkali metal (for example sodalite), a metal chelate and activated charcoal. The product from this process can be placed directly in the gasoline pool or, advantageously, fractionated to obtain one or more cuts which can be used as feeds for etherification.
    Type: Grant
    Filed: September 23, 1997
    Date of Patent: February 13, 2001
    Assignee: Institut Francais du Petrole
    Inventors: Thierry Chapus, Blaise Didillon, Christian Marcilly, Charles Cameron
  • Patent number: 5741415
    Abstract: The demercaptanization of petroleum distillates may be carried out by means of the oxidation of the mercaptans contained therein using the oxygen in the air, at a temperature of about 80.degree. to about 220.degree. C., in the presence of about 0.01 to about 10.0 mass % of a water-soluble salt of copper, iron, nickel, or cobalt, on a fibrous carbonaceous material in the form of a woven fabric, felt, rope, or twisted strand, used as a heterogeneous catalyst. The fibrous carbonaceous material used in the process contains oxides of calcium, magnesium, copper, manganese, iron, zinc, and aluminum in an amount of up to about 0.03 mass %.
    Type: Grant
    Filed: September 27, 1994
    Date of Patent: April 21, 1998
    Assignee: Chevron U.S.A. Inc.
    Inventors: A. M. Mazgarov, A. F. Vildanov, N. G. Bazhirova
  • Patent number: 5026474
    Abstract: A process for sweetening a petroleum fraction by catalytic oxidation of mercaptans contained therein in a fixed bed of the supported catalyst, with the oxidation reaction being carried out in the absence of an aqueous phase and in the presence of an oxidizing agent, and the water molecules formed during the oxidation reaction being removed from the catalyst support by washing the latter periodically with a substantial quantity of a polar solvent that is miscible with water.
    Type: Grant
    Filed: December 21, 1989
    Date of Patent: June 25, 1991
    Assignee: Compagnie de Raffinage et de Distribution Total France
    Inventors: Rene Blondeau, Claude Marty, Patrick Ansquer
  • Patent number: 4929340
    Abstract: This invention relates to an improved process and catalyst for treating a sour hydrocarbon stream. The improvement comprises the use of a dipolar compound which has a positively charged atom and an electronegative group in the same structure. A particularly preferred dipolar compound is ephedrine. The dipolar compounds may be used in conjunction with a metal chelate and a basic solution either in a liquid-liquid process or a fixed bed process with substantially increased performance for oxidizing mercaptans which are found in the sour hydrocarbon stream.
    Type: Grant
    Filed: July 31, 1989
    Date of Patent: May 29, 1990
    Assignee: UOP
    Inventors: Sheila Pollastrini, Jeffery C. Bricker, Robert R. Frame
  • Patent number: 4909925
    Abstract: Hydrogen sulphide is scavenged from a feedstock comprising crude oil and hydrogen sulphide by adding a compound of general formula ##STR1## to the feedstock. R is an alkyl group containing 1 to 18 carbon atoms, an aryl group, or an alkyl aryl group wherein the alkyl moiety contains 1 to 18 carbon atoms and L is a leaving group.Preferred scavengers include acetic anhydride and triacetamide.
    Type: Grant
    Filed: March 20, 1989
    Date of Patent: March 20, 1990
    Assignee: The British Petroleum Company p.l.c.
    Inventors: Philip K. G. Hodgson, Julie A. McShea, Edward J. Tinley
  • Patent number: 4897180
    Abstract: This invention relates to a catalytic composite effective in oxidizing mercaptans contained in a sour petroleum distillate to disulfides. The catalytic composite comprises a metal chelate, an onium compound and optionally an alkali metal hydroxide. The onium compound may be selected from the group consisting of phosphonium, arsonium, stibonium, oxonium and sulfonium compounds, with phosphonium, oxonium and sulfonium compounds preferred. Additionally, metal phthalocyanines are a preferred class of metal chelates. This invention also relates to an improved process for treating a sour petroleum distillate, wherein the improvement comprises using the catalytic composite described above.
    Type: Grant
    Filed: January 30, 1989
    Date of Patent: January 30, 1990
    Assignee: UOP
    Inventors: Jeffery C. Bricker, Robert R. Frame
  • Patent number: 4824818
    Abstract: This invention relates to a catalytic composite effective in oxidizing mercaptans contained in a sour petroleum distillate to disulfides. The catalytic composite comprises a metal chelate, an onium compound and optionally an alkali metal hydroxide. The onium compound may be selected from the group consisting of phosphonium, arsonium, stibonium, oxonium and sulfonium compounds, with phosphonium, oxonium and sulfonium compounds preferred. Additionally, metal phthalocyanines are a preferred class of metal chelates. This invention also relates to an improved process for treating a sour petroleum distillate, wherein the improvement comprises using the catalytic composite described above.
    Type: Grant
    Filed: February 5, 1988
    Date of Patent: April 25, 1989
    Assignee: UOP Inc.
    Inventors: Jeffery C. Bricker, Robert R. Frame