With Added Nitrogen Containing Compound Patents (Class 208/206)
  • Patent number: 11261386
    Abstract: An integrated refinery process for removing mercaptans from a hydrocarbon stream containing mercaptans and converting by-product disulfide oil to useful products. The process includes introducing the hydrocarbon stream containing mercaptans into an extraction vessel containing an alkaline solution and passing the hydrocarbon stream through an extraction section of the extraction vessel which includes one or more liquid-liquid contacting decks for reaction to convert the mercaptans to alkali metal alkanethiolates. Further, the process includes withdrawing a hydrocarbon product stream free of mercaptans from the extraction vessel and recovering spent caustic containing alkali metal alkanethiolates from the extraction vessel.
    Type: Grant
    Filed: May 20, 2020
    Date of Patent: March 1, 2022
    Assignee: Saudi Arabian Oil Company
    Inventors: Omer Refa Koseoglu, Robert Peter Hodgkins
  • Patent number: 11083201
    Abstract: A composition comprising a chelate-based ternary complex is useful for: (1) at least in-part disabling existing populations of microorganisms; and (2) at least in-part inhibiting growth of new microorganism populations. The chelate-based ternary complex comprises a hydrogen peroxide component, a plant compatible growth promoter component and a divalent zinc ion component. The plant compatible growth promoter component may comprise a urea component or a gluconate component or a salicylate component.
    Type: Grant
    Filed: October 13, 2015
    Date of Patent: August 10, 2021
    Assignee: UNIVERSITY OF CENTRAL FLORIDA RESEARCH FOUNDATION, INC.
    Inventors: Swadeshmukul Santra, Smruti Das, Parthiban Rajasekaran, Tyler Maxwell
  • Patent number: 9983187
    Abstract: The present invention is a system for the extraction and quantification of tetraprotic naphthenic acids present in oils, precursors of the formation of calcium naphthenates, which are potential formers of deposits, causing of damage to pieces of equipment used in the oil production industry.
    Type: Grant
    Filed: September 22, 2015
    Date of Patent: May 29, 2018
    Assignee: PETROLEO BRASILEIRO S.A.-PETROBRAS
    Inventors: Flávio Cortiñas Albuquerque, Rafael dos Santos Nascimento de Brito, Marcele Abreu Lopes
  • Patent number: 9914886
    Abstract: Embodiments of apparatuses and methods for conversion of mercaptans are provided. In one example, an apparatus comprises a vessel that is capable to receive a feed stream that comprises liquid hydrocarbons and the mercaptans. The vessel comprises a catalyst bed section that is capable of contacting the feed stream with a catalyst in the presence of oxygen (O2) and caustic at reaction conditions effective to oxidize the mercaptans and form a caustic-containing, sweetened liquid hydrocarbon-containing stream. A coalescing bed section is capable to coalesce and separate at least a portion of the caustic from the caustic-containing, sweetened liquid hydrocarbon-containing stream for forming a caustic-depleted, sweetened liquid hydrocarbon-containing product stream.
    Type: Grant
    Filed: June 10, 2014
    Date of Patent: March 13, 2018
    Assignee: UOP LLC
    Inventors: Jonathan Andrew Tertel, Jasna Karagic, Luigi Laricchia
  • Patent number: 9181498
    Abstract: A process for removing sulfur compounds from a liquid hydrocarbon stream includes the steps of feeding the hydrocarbon stream to a recirculation section of an extraction vessel wherein the recirculation section contains a first alkaline solution; passing the hydrocarbon stream through the recirculation section; recirculating at least a part of a first alkaline stream to a top deck of one or more liquid-liquid contacting decks of the recirculation section; passing the hydrocarbon stream from the recirculation section to an extraction section of the extraction vessel wherein the extraction section includes one or more liquid-liquid contacting decks; feeding a second alkaline stream to an upper deck of the one or more liquid-liquid contacting decks of the extraction section wherein the second alkaline stream includes a second alkaline solution; and withdrawing a hydrocarbon product stream from the extraction vessel. An apparatus for removing sulfur compounds from the hydrocarbon stream is also disclosed.
    Type: Grant
    Filed: May 29, 2013
    Date of Patent: November 10, 2015
    Assignee: UOP LLC
    Inventors: Jonathan Andrew Tertel, Peter A. Meister
  • Patent number: 8318005
    Abstract: The present invention relates to making tetra-sulfo iron-phthalocyanine by reacting sulfonated reactant(s) in the presence a boron-containing promoter. The present invention also relates to making tetra-sulfo iron phthalocyanine more tolerant to oxygen by combining the tetra-sulfo iron-phthalocyanine with a stabilizing amount of a complexing agent (e.g., a stabilizing amine) and/or contacting the tetra-sulfo iron-phthalocyanine with steam.
    Type: Grant
    Filed: December 21, 2007
    Date of Patent: November 27, 2012
    Assignee: DOW Global Technologies LLC
    Inventors: John M. Griffin, Stephen A. Bedell, Clare M. Worley
  • 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: 6656977
    Abstract: A method for controlling the foaming of an aqueous organic compound-containing composition by the incorporation of a foam controlling amount of a compound of the formula: where n and m are 2 or 3, x is 1-6, R′ is a C4 to C22 alkyl group, where R′ is a C4 to C22 alkyl group, the compound generating an initial foam height at least 30% less than a 0.1 wt % aqueous solution of dioctyl sodium sulfosuccinate (DOSS) when added at 0.1 wt % to the DOSS solution.
    Type: Grant
    Filed: July 20, 2001
    Date of Patent: December 2, 2003
    Assignee: Air Products and Chemical, Inc.
    Inventors: Caroline Sassano Slone, Kevin Rodney Lassila
  • 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
  • Publication number: 20030019793
    Abstract: This invention relates to reducing the amount of thiols (mercaptans) in petroleum streams, specifically, mercaptans above the five carbon molecular weight range.
    Type: Application
    Filed: September 20, 2002
    Publication date: January 30, 2003
    Inventors: Mark Alan Greaney, Michael Charles Kerby, Roby Bearden
  • Patent number: 6352640
    Abstract: The invention describes a method for preparing a low sulfur motor gasoline utilizing ethanol and caustic extraction.
    Type: Grant
    Filed: April 18, 2000
    Date of Patent: March 5, 2002
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Bruce Randall Cook, Richard Harry Ernst, Mark Alan Greaney
  • Patent number: 6013175
    Abstract: A method for scavenging mercaptans in a hydrocarbon fluid is disclosed. According to the method, an effective mercaptan-scavenging amount of an aqueous scavenging composition is added to the fluid. The composition comprises a quaternary ammonium hydroxide of the formula R.sup.1 R.sup.2 R.sup.3 R.sup.4 NOH. R.sup.1 and R.sup.2 are, independently, alkyl groups of from one to about eighteen carbon atoms, aryl groups of from six to about eighteen carbon atoms or alkylaryl groups of from seven to about eighteen carbon atoms. R.sup.3 is an alkyl group of from two to about eighteen carbon atoms, an aryl group of from two to about eighteen carbon atoms or an alkylaryl group of from four to about eighteen carbon atoms. R.sup.2 and R.sup.3 may be joined to form a heterocyclic ring including the N and optionally an oxygen atom. R.sup.4 is --(CH.sub.2 CH.sub.2 O).sub.n H, wherein n is an integer from one to about eighteen, or --CHR.sup.5 CHR.sup.6 Y, wherein R.sup.5 and R.sup.
    Type: Grant
    Filed: September 14, 1998
    Date of Patent: January 11, 2000
    Assignee: Baker Hughes, Inc.
    Inventors: Jerry J. Weers, David R. Gentry
  • Patent number: 5961819
    Abstract: An improved process is described for removing mercaptan sulfur from sour hydrocarbon distillate streams comprising of treating a sour hydrocarbon distillate stream in two oxidation zones within a reaction vessel. The first treatment occurs in the presence of a fiber bundle and the subsequent treatment over a bed of supported oxidation catalyst. The improvement comprises continuously keeping the bed in contact with an aqueous alkali metal hydroxide to maintain the catalyst in a caustic-wetted state, without interrupting the operation of the process.
    Type: Grant
    Filed: February 9, 1998
    Date of Patent: October 5, 1999
    Assignee: Merichem Company
    Inventors: Binh N. Lee, Michael W. Walther
  • Patent number: 5840177
    Abstract: A method for scavenging mercaptans in a hydrocarbon fluid is disclosed. According to the method, an effective mercaptan-scavenging amount of an aqueous scavenging composition is added to the fluid. The composition comprises a quaternary ammonium hydroxide of the formula R.sup.1 R.sup.2 R.sup.3 R.sup.4 NOH. R.sup.1 and R.sup.2 are, independently, alkyl groups of from one to about eighteen carbon atoms, aryl groups of from six to about eighteen carbon atoms or alkylaryl groups of from seven to about eighteen carbon atoms. R.sup.3 is an alkyl group of from two to about eighteen carbon atoms, an aryl group of from two to about eighteen carbon atoms or an alkylaryl group of from four to about eighteen carbon atoms. R.sup.2 and R.sup.3 may be joined to form a heterocyclic ring including the N and optionally an oxygen atom. R.sup.4 is --(CH.sub.2 CH.sub.2 O).sub.n H, wherein n is an integer from one to about eighteen, or --CHR.sup.5 CHR.sup.6 Y, wherein R.sup.5 and R.sup.
    Type: Grant
    Filed: September 16, 1997
    Date of Patent: November 24, 1998
    Assignee: Baker Hughes Incorporated
    Inventors: Jerry J. Weers, David R. Gentry
  • 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: 5683574
    Abstract: Low molecular weight mercaptans are extracted from petroleum (e.g., crude oil) or gas condensate by contacting the mercaptans with oxygen in an aqueous solution of a metal hydroxide in the presence of a cobalt dihalodihydroxydisulfophthalocyanine catalyst. The catalyst is introduced into the crude oil or gas condensate continuously in the form of a catalytic complex in an aqueous solution of a metal hydroxide.
    Type: Grant
    Filed: July 31, 1995
    Date of Patent: November 4, 1997
    Assignee: Chevron U.S.A. Inc.
    Inventors: Akhmet Mazgarovich Mazgarov, Azat Faridovich Vildanov, Nailya Gilmutdinovna Bazhirova, Gulnara Burkhanova Niamutdinova, Sergei Nikolaevich Sukhov
  • Patent number: 5591323
    Abstract: A process for sweetening a petroleum cut containing mercaptans, wherein said petroleum cut is subjected to oxidation conditions by being contacted with a porous catalyst, in the presence of air said process being characterised in that said catalyst comprises 10 to 98% by weight of at least one mineral solid phase constituted of an alkaline aluminosilicate with a Si/Al atomic ratio less than or equal to 5, 1 to 60% by weight of active carbon, 0.02 to 2% by weight of at least one metal chelate and 0 to 20% by weight of at least one organic or mineral binding agent, has a basicity determined according to the 2896 ASTM standard with 20 milligrams of potash per gram and a total BET surface area of 10 m.sup.2 g.sup.-1, and contains inside its pore structure a permanent aqueous phase representing 0.1 to 40% by weight of dry catalyst.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: January 7, 1997
    Assignee: Institut Francais du Petrole
    Inventors: Christian Marcilly, Serge Leporq, Philippe Courty
  • Patent number: 5340465
    Abstract: An improved process for treating a sour hydrocarbon stream has been developed. This process involves contacting the sour hydrocarbon fraction with a metal oxide solid solution in the presence of an oxidizing agent such as air or oxygen. One example of a solid solution which can be used is a nickel oxide/magnesium oxide/aluminum oxide solid solution.
    Type: Grant
    Filed: October 14, 1993
    Date of Patent: August 23, 1994
    Assignee: UOP
    Inventors: Ralph D. Gillespie, Jennifer S. Holmgren
  • Patent number: 5273646
    Abstract: This invention relates to a process for improving the activity of a catalyst effective in sweetening a hydrocarbon fraction containing mercaptans. The process involves adding to the hydrocarbon fraction an effective amount of an aqueous solution comprising ammonium hydroxide, a metal chelate and an onium compound.
    Type: Grant
    Filed: October 19, 1992
    Date of Patent: December 28, 1993
    Assignee: UOP
    Inventors: Robert R. Frame, Jeffery C. Bricker, Laurence O. Stine, Thomas A. Verachtert
  • Patent number: 5244643
    Abstract: Fuel gas streams containing oxygen are treated by a process that performs simultaneous sweetening and absorption of mercaptan compounds. The mercaptan oxidation catalyst and an aqueous alkaline solution and a low vapor pressure liquid hydrocarbon stream contact the fuel gas feed in a mixing vessel to sweeten the mercaptans and absorb resulting disulfides from the gas stream into the liquid hydrocarbon stream. A separation vessel receives the dual phase effluent from the mixing vessel and settles the effluent into three component phases. An upper gas phase provides a treated fuel gas stream, an intermediate hydrocarbon phase provides liquid hydrocarbons containing disulfides for removal from the process, and recycle to the mixing vessel and an alkaline solution drains from the bottom of the settler. The aqueous alkaline solution is pumped back to the mixing vessel in combination with the mercaptan oxidation catalyst.
    Type: Grant
    Filed: February 21, 1992
    Date of Patent: September 14, 1993
    Assignee: UOP
    Inventor: Thomas A. Verachtert
  • Patent number: 5180484
    Abstract: This invention relates to a liquid-liquid process for treating a sour hydrocarbon fraction. The process comprises contacting the hydrocarbon fraction in the presence of an oxidizing agent with an aqueous solution containing ammonium hydroxide, a metal chelate and an onium compound selected from the group consisting of quaternary ammonium, phosphonium, arsonium, stibonium, oxonium and sulfonium compounds. A preferred onium compound is a quaternary ammonium compound with an especially preferred compound being a quaternary ammonium halide.
    Type: Grant
    Filed: November 29, 1991
    Date of Patent: January 19, 1993
    Assignee: UOP
    Inventors: Robert R. Frame, Jeffery C. Bricker, Laurence O. Stine, Thomas A. Verachtert
  • Patent number: 5169516
    Abstract: A process for removal of arsenic from a hydrocarbon stream containing arsenic together with mercaptan and non-mercaptan sulfur compounds. The hydrocarbon stream is passed through at least two mercaptan oxidizing reactors in series wherein the mercaptans are oxidized to disulfides to produce a low mercaptan liquid containing no more than 1.5 ppm sulfur as mercaptans. The low mercaptan liquid is passed over an arsenic sorbent catalyst containing less than 20 weight percent gamma alumina to selectively sorb arsenic substantially without sorbing non-mercaptan sulfur compounds.
    Type: Grant
    Filed: August 30, 1991
    Date of Patent: December 8, 1992
    Inventor: Norman L. Carr
  • Patent number: 4968411
    Abstract: A catalyst composition useful in the catalytic oxidation of mercaptans is disclosed. The composition is a stable aqueous slurry or suspension of a first component which is predominantly a metal phthalocyanine disulfonate compound, and a second component which is predominantly a tetrasulfonated metal phthalocyanine compound.
    Type: Grant
    Filed: July 19, 1989
    Date of Patent: November 6, 1990
    Assignee: ARI Technologies, Inc.
    Inventor: Edward J. Dowd
  • Patent number: 4956325
    Abstract: The present invention is directed to impregnating a support material with a metal phthalocyanine oxidation catalyst dissolved in monoethanol amine. More specifically, the invention is directed to the method of impregnating a catalyst support such as carbon particles with an aqueous solution of monoethanol amine wherein the monoethanol amine solvent is present in an amount from about 0.25% to about 50% by weight.
    Type: Grant
    Filed: March 23, 1989
    Date of Patent: September 11, 1990
    Assignee: Merichem Company
    Inventor: Binh Ngoc Le
  • 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: 4913802
    Abstract: This invention relates to a process for sweetening a sour hydrocarbon fraction containing mercaptans. The process involves contacting the hydrocarbon fraction in the presence of an oxidizing agent with a catalytic composite, ammonium hydroxide and a quaternary ammonium hydroxide. There is a synergistic effect between the ammonium hydroxide and the quaternary ammonium hydroxide. Use of ammonium hydroxide instead of an alkaline hydroxide allows the waste stream to be re-used in other parts of the refinery, and allows for easier disposal of the waste stream.
    Type: Grant
    Filed: May 8, 1989
    Date of Patent: April 3, 1990
    Assignee: UOP
    Inventors: Jeffery C. Bricker, Laurence O. Stine, Thomas A. Verachtert
  • 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: 4908122
    Abstract: The present invention deals with a process for sweetening a sour hydrocarbon fraction containing mercaptans. The process involves contacting the hydrocarbon fraction in the presence of an oxidizing agent with a catalytic composite, ammonium hydroxide and a quaternary ammonium salt other than hydroxide. The instant process does not use any strong base nor any alkali hydroxides to sweeten the sour hydrocarbon fraction.
    Type: Grant
    Filed: May 8, 1989
    Date of Patent: March 13, 1990
    Assignee: UOP
    Inventors: Robert R. Frame, Jeffery C. Bricker
  • Patent number: 4906354
    Abstract: The thermal stability of jet fuel sweetened by oxidation is improved by washing the sweetened fuel with strong aqueous caustic.
    Type: Grant
    Filed: September 10, 1987
    Date of Patent: March 6, 1990
    Assignee: Mobil Oil Corporation
    Inventors: Edward G. Barry, Joseph G. Bendoraitis, Perry W. Kirklin, David A. Pappal
  • 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: 4808765
    Abstract: There is disclosed a process for treating liquid (liquifiable) and gaseous hydrocarbons to remove substantially all of the acid gases including COS by contacting the hydrocarbon streams with specific aqueous treating agents in a series of sequential specific limit operations and apparatus.
    Type: Grant
    Filed: July 17, 1987
    Date of Patent: February 28, 1989
    Assignee: The Dow Chemical Company
    Inventors: Roscoe L. Pearce, Richard A. Wolcott
  • Patent number: 4705620
    Abstract: A process is disclosed for treating a sour hydrocarbon stream comprising extracting the mercaptans contained in said hydrocarbon stream with an alkaline solution in an extraction zone, oxidizing the mercaptans to disulfides in the presence of an oxidation catalyst, separating said disulfide from said alkaline solution, reducing the residual disulfides in said alkaline solution to mercaptans and recycling said alkaline solution to the extraction zone. Two ways are disclosed to effect the reduction of the disulfides to mercaptans: (1) hydrogenation with a supported metal catalyst and (2) electrochemical reduction.
    Type: Grant
    Filed: December 16, 1986
    Date of Patent: November 10, 1987
    Assignee: UOP Inc.
    Inventors: Jeffery C. Bricker, Bruce E. Staehle
  • Patent number: 4490246
    Abstract: A process is disclosed for treating hydrocarbon streams by the catalyzed oxidation of mercaptans to disulfides. In the process, the hydrocarbon-containing stream is admixed with air and then passed through an oxidation zone. The oxidation zone effluent is decanted to remove an aqueous alkaline solution in a high pressure separation zone. It is then depressurized into a low pressure separator in which dissolved excess nitrogen and oxygen are substantially removed from the hydrocarbons. The treated hydrocarbons are then pressurized to force their flow into a low pressure product receiving facility. This sequence eliminates or minimizes the discharge of gaseous nitrogen and oxygen and hydrocarbon vapors in the storage facility, where they are pollution abatement problems and possible safety hazards.
    Type: Grant
    Filed: November 18, 1983
    Date of Patent: December 25, 1984
    Assignee: UOP Inc.
    Inventor: Thomas A. Verachtert
  • Patent number: 4481106
    Abstract: A process is disclosed for treating hydrocarbon streams such as naphtha by the oxidation of mercaptans into disulfide compounds which remain in the hydrocarbon stream. The conversion is effected during passage of the hydrocarbon and an aqueous stream downward through a cylindrical mass of liquid-liquid contact material. The liquids then flow through a cylindrical screen into an annular separation zone which surrounds a lower part of the contact material. After decantation in the separation zone, the aqueous material, which preferably contains the oxidation catalyst, is recycled.
    Type: Grant
    Filed: December 5, 1983
    Date of Patent: November 6, 1984
    Assignee: UOP Inc.
    Inventor: Thomas A. Verachtert
  • Patent number: 4481107
    Abstract: A process is disclosed for oxidizing difficultly oxidizable mercaptans contained in a hydrocarbon fraction which comprises adding a hydrocarbon soluble alkali metal compound, capable of forming the alkali metal mercaptides of the difficultly oxidized mercaptans, to the hydrocarbon fraction; and contacting the resulting hydrocarbon fraction containing the hydrocarbon soluble alkali metal compound with a metal chelate catalyst disposed on an adsorptive support in the presence of a hydrated oxygen-containing gas and in the absence of a separate water phase.
    Type: Grant
    Filed: April 6, 1984
    Date of Patent: November 6, 1984
    Assignee: UOP Inc.
    Inventor: Peter Urban
  • Patent number: 4412912
    Abstract: A process is disclosed for treating hydrocarbon streams for the purpose of removing mercaptans and also converting the remaining mercaptans to disulfides which remain in the hydrocarbon stream being treated. The hydrocarbons rise through a contacting column countercurrently to a descending stream of an aqueous alkaline solution. A limited amount of an oxygen-containing gas is passed into an intermediate point in the column thereby dividing it into an upper sweetening section and a lower extraction section. The flow rate of the oxygen-containing stream is preferably low enough that any gas not consumed in the catalytic oxidation of mercaptans becomes dissolved in the hydrocarbon product stream, and preferably remains dissolved at atmospheric pressure.
    Type: Grant
    Filed: March 1, 1983
    Date of Patent: November 1, 1983
    Assignee: UOP Inc.
    Inventor: George Asdigian
  • Patent number: 4411776
    Abstract: A method of treating a mercaptan-containing sour petroleum distillate is disclosed which method comprises the steps of contacting the distillate at oxidation conditions with a catalytic composite comprising a metal chelate, at least about 10 wt. % of an alkali metal hydroxide, and an adsorptive support, prepared by admixing the support, metal chelate, alkali metal hydroxide, and an alcohol having fewer than about six carbon atoms, to form an admixture having less than about 25 wt. % water, and drying the admixture at a temperature of less than about 30.degree. C.
    Type: Grant
    Filed: September 16, 1982
    Date of Patent: October 25, 1983
    Assignee: UOP Inc.
    Inventor: David H. J. Carlson
  • Patent number: 4378305
    Abstract: A catalytic composite comprising a metal chelate mercaptan oxidation catalyst impregnated on a basic anion exchange resin is disclosed. The catalytic composite is particularly useful to effect the oxidation of mercaptans contained in a sour petroleum distillate.
    Type: Grant
    Filed: May 20, 1981
    Date of Patent: March 29, 1983
    Assignee: UOP Inc.
    Inventor: David H. J. Carlson
  • Patent number: 4374042
    Abstract: A method of reactivating a mercaptan oxidation catalytic composite of an adsorptive support and a metal chelate comprising contacting the composite with an aqueous solution of a quaternary ammonium compound and a linear ionic compound at a temperature of from about 55.degree. C. to about 175.degree. C.
    Type: Grant
    Filed: April 24, 1981
    Date of Patent: February 15, 1983
    Assignee: UOP Inc.
    Inventor: Robert R. Frame
  • Patent number: 4364843
    Abstract: A catalytic composite comprising a metal chelate, at least about 10 wt. % of an alkali metal hydroxide, and an adsorptive support, prepared by admixing the support, metal chelate, alkali metal hydroxide, and an alcohol having fewer than about five carbon atoms, to form an admixture having less than about 25 wt. % water, and drying the admixture at a temperature of less than about 30.degree. C.
    Type: Grant
    Filed: April 20, 1981
    Date of Patent: December 21, 1982
    Assignee: UOP Inc.
    Inventor: David H. J. Carlson
  • Patent number: 4360421
    Abstract: A method of treating a mercaptan-containing sour petroleum distillate which comprises contacting said distillate with a catalytic composite comprising a carrier material, a metal chelate oxidation catalyst, a substituted ammonium compound, and a linear ionic compound.
    Type: Grant
    Filed: December 17, 1981
    Date of Patent: November 23, 1982
    Assignee: UOP Inc.
    Inventor: Robert R. Frame
  • Patent number: 4354926
    Abstract: Disclosed are a metal chelate-alkali metal hydroxide-quaternary ammonium hydroxide catalytic composite, and a process of treating sour petroleum distillates utilizing the catalytic composite. The catalytic composite comprises a metal chelate, a quaternary ammonium hydroxide, and an alkali metal hydroxide disposed on a molecular sieve, the alkali metal hydroxide comprising at least about 10 wt. % of the catalytic composite. The method of treating sour petroleum distillates comprises contacting the distillates at oxidation conditions with the catalytic composite described above.
    Type: Grant
    Filed: December 10, 1980
    Date of Patent: October 19, 1982
    Assignee: UOP Inc.
    Inventor: David H. J. Carlson
  • Patent number: 4337147
    Abstract: Disclosed is a method for treating sour mercaptan-containing petroleum distillates by contacting the distillates at oxidation conditions with a catalytic composite comprising a metal chelate, an alkali metal hydroxide, and a quaternary ammonium hydroxide disposed on an adsorptive support, thereby converting the mercaptan compounds contained in said distillates to disulfides.
    Type: Grant
    Filed: August 26, 1980
    Date of Patent: June 29, 1982
    Assignee: UOP Inc.
    Inventor: Robert R. Frame
  • Patent number: 4324650
    Abstract: Disclosed are a catalytic composite, and a method of preparing a catalytic composite, useful in the treatment of sour mercaptan-containing petroleum distillates, and a method of using the catalytic composite in treating sour petroleum distillates. More specifically, the method of preparation comprises contacting a molecular sieve support with a specified substituted ammonium compound, drying the resulting composite, thereafter contacting the resulting composite with an alkali metal hydroxide and a metal chelate, the alkali metal hydroxide being in a weight ratio with the adsorptive support of from about 0.1:1 to about 1:1, and thereafter drying the resulting catalytic composite. A sour petroleum distillate can be treated with the catalytic composite by contacting the distillate at oxidation conditions with the catalytic composite.
    Type: Grant
    Filed: November 24, 1980
    Date of Patent: April 13, 1982
    Assignee: UOP Inc.
    Inventor: David H. J. Carlson
  • Patent number: 4320029
    Abstract: A catalytic composite especially useful in the treatment of sour petroleum distillates, comprising a carrier material, a metal chelate, a substituted ammonium compound, and a linear ionic compound. A method of preparing a catalytic composite comprising contacting a carrier material with a solution of a metal chelate, a substituted ammonium compound, and a linear ionic compound.
    Type: Grant
    Filed: July 17, 1980
    Date of Patent: March 16, 1982
    Assignee: UOP Inc.
    Inventor: Robert R. Frame
  • Patent number: 4308169
    Abstract: A method of reactivating a mercaptan oxidation catalytic composite of an adsorptive support and a metal chelate comprising contacting the composite with an aqueous solution of a quarternary ammonium compound and a linear ionic compound at a temperature of from about 55.degree. C. to about 175.degree. C.
    Type: Grant
    Filed: July 21, 1980
    Date of Patent: December 29, 1981
    Assignee: UOP Inc.
    Inventor: Robert R. Frame
  • Patent number: 4299729
    Abstract: A method of reactivating a mercaptan oxidation catalytic composite of an adsorptive support and a metal chelate comprising the steps of first contacting the composite with an aqueous ammoniacal solution of a metal chelate, and second contacting the composite with an aqueous solution of a quaternary ammonium compound at a temperature of from about 55.degree. C. to about 175.degree. C.
    Type: Grant
    Filed: June 4, 1980
    Date of Patent: November 10, 1981
    Assignee: UOP Inc.
    Inventor: Robert R. Frame
  • Patent number: 4298502
    Abstract: A catalytic composite comprising a metal chelate mercaptan oxidation catalyst impregnated on a basic anion exchange resin is disclosed. The catalytic composite is particularly useful to effect the oxidation of mercaptans contained in a sour petroleum distillate.
    Type: Grant
    Filed: December 10, 1980
    Date of Patent: November 3, 1981
    Assignee: UOP Inc.
    Inventor: David H. J. Carlson