With Organic Reagent Patents (Class 208/237)
  • Patent number: 6733660
    Abstract: Economical processes are disclosed for the production of fuels of reduced sulfur content from a feedstock, typically derived from natural petroleum, wherein the feedstock is comprised of limited amounts of sulfur-containing organic compounds as unwanted impurities. The processes involve integrated, multistage processes which include pretreatment of a light naphtha with a solid adsorbent to remove basic nitrogen containing compounds, chemical conversion of one or more of the sulfur-containing impurities to higher boiling products by alkylation, and removing the higher boiling products by fractional distillation. Advantageously, the processes include selective hydrogenation of the high-boiling fraction whereby the incorporation of hydrogen into hydrocarbon compounds, sulfur-containing organic compounds, and/or nitrogen-containing organic compounds assists by hydrogenation removal of sulfur and/or nitrogen.
    Type: Grant
    Filed: July 31, 2001
    Date of Patent: May 11, 2004
    Assignee: BP Corporation North America Inc.
    Inventors: Vivek R. Pradhan, Ptoshia A. Burnett, Stacey McDaniel, Michael Hodges
  • Publication number: 20040079680
    Abstract: Fossil fuels are combined with an aqueous liquid and a dialkyl ether to form an aqueous-organic reaction medium which is passed through an ultrasound chamber on a continuous flow-through basis. The emerging mixture separates spontaneously into aqueous and organic phases, from which the organic phase is readily isolated as the desulfurized fossil fuel.
    Type: Application
    Filed: October 23, 2002
    Publication date: April 29, 2004
    Applicant: SulphCo., Inc.
    Inventor: Rudolf W. Gunnerman
  • Patent number: 6726835
    Abstract: Savings in the processing of a naphtha boiling range feed containing a thiophene are achieved by fractionating the feed stream in a single dividing wall column to yield a C6-minus overhead stream, a side-draw containing the majority of the C6 and C7 paraffins and olefins, and a bottoms stream comprising C7 and heavier hydrocarbons. A dividing wall column provides better control of the concentration of both thiophene and toluene in the side-draw. Less of the valuable naphtha is lost and the amount of thiophene in the overhead product is minimized.
    Type: Grant
    Filed: December 17, 2002
    Date of Patent: April 27, 2004
    Assignee: UOP LLC
    Inventors: Gavin P. Towler, Michael A. Schultz
  • Publication number: 20040019248
    Abstract: Disclosed is a method for settling suspended finely divided inorganic solid particles from a hydrocarbon slurry using an additive. The additive comprises (a) a hydroxy-terminated polyoxyalkylate chain(s) containing polymer having at least one oxygen atom and at least one nitrogen atom and, optionally, (b) other components such as a solvent, an acid or mixtures thereof.
    Type: Application
    Filed: June 6, 2003
    Publication date: January 29, 2004
    Applicant: Baker Hughes Incorporated
    Inventors: Joseph L. Stark, Robert S. Lauer, Lawrence N. Kremer
  • Patent number: 6638419
    Abstract: A method for obtaining oil products such as diesel fuel with improved quality, from a gas oil fraction containing organosulphur compounds such as dibenzenethiophenes and/or their derivatives, with initial and final boiling points generally ranging between about 170 and 480° C. The method includes at least two steps which consist in: (a) liquid-liquid extraction wherein the diesel fuel fraction is contacted with a solvent so as to obtain a gas oil-type raffinate with low content of sulphur and aromatic compounds and an extract rich in solvent and with high content of sulphur and aromatic compounds; (b) oxidation of the extract sulphur compounds so as to obtain, after separation, a heavy gas oil-type hydrocarbon effluent with low sulphur content, and a residue comprising oxidased organosulphur compounds. The invention also concerns oil products obtained by said method which can be used either for the formation of fuel for internal combustion engine with compression ignition (of the diesel type) or as fuel.
    Type: Grant
    Filed: January 10, 2002
    Date of Patent: October 28, 2003
    Assignee: Total Raffinage Distribution S.A.
    Inventors: Pedro Da Silva, Raphaƫl Le Gall
  • Publication number: 20030116474
    Abstract: Savings in the processing of a naphtha boiling range feed containing a thiophene are achieved by fractionating the feed stream in a single dividing wall column to yield a C6-minus overhead stream, a side-draw containing the majority of the C6 and C7 paraffins and olefins, and a bottoms stream comprising C7 and heavier hydrocarbons. A dividing wall column provides better control of the concentration of both thiophene and toluene in the side-draw. Less of the valuable naphtha is lost and the amount of thiophene in the overhead product is minimized.
    Type: Application
    Filed: December 17, 2002
    Publication date: June 26, 2003
    Inventors: Gavin P. Towler, Michael A. Schultz
  • Publication number: 20030089641
    Abstract: 1,3,5 (2H2,4H2,6H2) tripropanediamine N,N,N′,N′,N″,N″ hexamethyl is used to scavenge sulfur compounds from hydrocarbons. A novel method of making the triazine comprises autocondensing (CH3)2N CHCH2CH2N═CH2.
    Type: Application
    Filed: November 8, 2002
    Publication date: May 15, 2003
    Applicant: Clearwater International LLC.
    Inventor: Larry W. Gatlin
  • Patent number: 6540907
    Abstract: Savings in the processing of a naphtha boiling range feed containing a thiophene are achieved by fractionating the feed stream in a single dividing wall column to yield a C6-minus overhead stream, a side-draw containing the majority of the C6 and C7 paraffins and olefins, and a bottoms stream comprising C7 and heavier hydrocarbons. A dividing wall column provides better control of the concentration of both thiophene and toluene in the side-draw. Less of the valuable naphtha is lost and the amount of thiophene in the overhead product is minimized.
    Type: Grant
    Filed: July 9, 2001
    Date of Patent: April 1, 2003
    Assignee: UOP LLC
    Inventors: Gavin P. Towler, Michael A. Schultz
  • Publication number: 20030057136
    Abstract: In a conventional hydrodesulfurization process sulfur is removed from liquid hydrocarbons by reacting the sulfur in the liquid hydrocarbons with hydrogen to form H2S. A sour hydrogen gas stream consisting of unreacted hydrogen, H2S, and undesired light hydrocarbons is then separated from the liquid hydrocarbons, and the H2S is removed to sweeten the hydrogen stream for recycling. Some of the undesired light hydrocarbons resulting from the reaction may be separated by the purging method discussed. In the present invention efficient separation of the light hydrocarbons is enabled without substantial loss of recyclable hydrogen. Both the H2S and light hydrocarbons are separated from the sour hydrogen gas stream by passing the stream through an absorber where it is reacted with a nonaqueous liquor. The light hydrocarbons are absorbed in the liquor, from which they are subsequently separated.
    Type: Application
    Filed: August 20, 2002
    Publication date: March 27, 2003
    Inventors: Kenneth E. McIntush, Ken DeBerry, David W. DeBerry
  • Patent number: 6531103
    Abstract: The present invention provides a process for removing sulfur compounds including sulfur in the (−2) oxidation state such as mercaptans, dialkyl sulfides, carbonyl sulfide, hydrogen sulfide, thiophenes and benzothiophenes, from liquid or gas feed streams, particularly hydrocarbon feed streams such as, for example, natural gas and refinery process streams. According to the process, such a feed stream including these sulfur impurities is contacted with an absorbent which includes a metal ion-containing organic composition such as, for example, iron, copper, lead, nickel, tin, zinc or mercury cation-containing phthalocyanine or porphyrin to thereby form sulfur-metal cation coordination complexes in which the oxidation state of the sulfur and the metal cation remains essentially unchanged. The complexes are separated from the feed stream, and the absorbent is regenerated by disassociating the sulfur compound from the complexes.
    Type: Grant
    Filed: March 9, 2000
    Date of Patent: March 11, 2003
    Assignee: Union Carbide Chemicals and Plastics Technology Corporation
    Inventors: Leo Ernest Hakka, Paulino Forte
  • Publication number: 20030029776
    Abstract: Economical processes are disclosed for the production of fuels of reduced sulfur content from a feedstock, typically derived from natural petroleum, wherein the feedstock is comprised of limited amounts of sulfur-containing organic compounds as unwanted impurities. The processes involve integrated, multistage processes which include pretreatment of a light naphtha with a solid adsorbent to remove basic nitrogen containing compounds, chemical conversion of one or more of the sulfur-containing impurities to higher boiling products by alkylation, and removing the higher boiling products by fractional distillation. Advantageously, the processes include selective hydrogenation of the high-boiling fraction whereby the incorporation of hydrogen into hydrocarbon compounds, sulfur-containing organic compounds, and/or nitrogen-containing organic compounds assists by hydrogenation removal of sulfur and/or nitrogen.
    Type: Application
    Filed: July 31, 2001
    Publication date: February 13, 2003
    Inventors: Vivek R. Pradhan, Ptoshia A. Burnett, Stacey McDaniel, Michael Hodges
  • 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: 6483003
    Abstract: A process for removing impurities from a hydrocarbon component or fraction comprises mixing, in a liquid-liquid extraction step, an impurity-containing liquid hydrocarbon component or fraction, as an impure liquid hydrocarbon feedstock, with an acetonitrile-based solvent. Thereby, at least one impurity is extracted from the hydrocarbon component or fraction into the solvent. There is withdrawn from the extraction step, as a raffinate, purified hydrocarbon component or fraction, while there is withdrawn from the extraction step, as an extract, impurity-containing solvent.
    Type: Grant
    Filed: November 2, 2000
    Date of Patent: November 19, 2002
    Assignee: Sasol Technology (Proprietary) Limited
    Inventors: Waldo Eugene De Villiers, Petra De Wet, Magdalena Catharina Hough-Langanke, Hubert Naude, Atool Govan Pema
  • Publication number: 20020166799
    Abstract: The present invention relate to a process for sweetening of LPG, light petroleum distillates by liquid-liquid extraction using metal phthalocyanine sulphonamide catalyst which comprises extracting the mercaptanes contained 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: Application
    Filed: March 26, 2001
    Publication date: November 14, 2002
    Applicant: COUNCIL OF SCIENTIFIC & 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: 20020157989
    Abstract: Potassium formate is used together with a sulfide scavenger to remove and otherwise treat sulfhydryl compounds such as hydrogen sulfide present in hydrocarbons and aqueous substrates
    Type: Application
    Filed: April 23, 2002
    Publication date: October 31, 2002
    Applicant: Clearwater, Inc.
    Inventors: Larry W. Gatlin, Wayne Mueller
  • Patent number: 6444117
    Abstract: The general object of this invention is to provide an improved process for sweetening and desulfurizing sulfur-containing crude oil streams. Heating the sulfur-containing crude oil stream to an elevated temperature for an extended period of time while stirring and bubbling an inert gas into the crude accelerates the removal of sulfur containing gases from the crude oil stream. Furthermore, the addition of a polyalkylamine to the stirred crude oil can also greatly assist in the expulsion of sulfur containing gases. After processing under these conditions, the hydrogen sulfide producing capacity of the crude oil is reduced significantly, thus making the crude safer for transportation and handling by reducing the health and environmental risks.
    Type: Grant
    Filed: August 16, 2000
    Date of Patent: September 3, 2002
    Assignee: Texaco, Inc.
    Inventors: M. Rashid Khan, Vincent P. Nero, Lee Ann Brugger, Stephen J. DeCanio, David A. Storm
  • Patent number: 6406616
    Abstract: A process for desulfurizing hydrocarbons such as gasoline and similar petroleum products to reduce the sulfur content to a range of from about 2 to 15 ppm sulfur without affecting the octane rating is described. The sulfur containing hydrocarbon is contacted at slightly elevated temperatures with an oxidizing/extracting solution of formic acid, a small amount of hydrogen peroxide, and no more than about 25 wt % water.
    Type: Grant
    Filed: September 12, 2001
    Date of Patent: June 18, 2002
    Assignee: Unipure Corporation
    Inventors: Alkis S. Rappas, Vincent P. Nero, Stephen J. DeCanio
  • Patent number: 6402940
    Abstract: A process for desulfurizing fuels such as diesel oil and similar petroleum products to reduce the sulfur content to a range of from about 2 to 15 ppm sulfur is described. The sulfur containing fuel is contacted at slightly elevated temperatures with an oxidizing/extracting solution of formic acid, a small amount of hydrogen peroxide, and no more than about 25 wt % water. A removal process for separating substituted dibenzothiophene oxidation products from tile fuel is also described.
    Type: Grant
    Filed: September 1, 2000
    Date of Patent: June 11, 2002
    Assignee: Unipure Corporation
    Inventor: Alkis S. Rappas
  • Patent number: 6358402
    Abstract: A method for separating sulfur species from hydrocarbon streams, particularly cracked naphtha streams, using extractive distillation. The method effectively separates sulfur species from cracked naphtha streams without substantially lowering the olefin content.
    Type: Grant
    Filed: December 28, 1999
    Date of Patent: March 19, 2002
    Assignee: ExxonMobil Research and Engineering Company
    Inventor: Robert C. Schucker
  • Publication number: 20020029997
    Abstract: A process for desulfurizing hydrocarbons such as gasoline and similar petroleum products to reduce the sulfur content to a range of from about 2 to 15 ppm sulfur without affecting the octane rating is described. The sulfur containing hydrocarbon is contacted at slightly elevated temperatures with an oxidizing/extracting solution of formic acid, a small amount of hydrogen peroxide, and no more than about 25 wt % water.
    Type: Application
    Filed: September 12, 2001
    Publication date: March 14, 2002
    Applicant: UniPure Corporation
    Inventors: Alkis S. Rappas, Vincent P. Nero, Stephen J. DeCanio
  • 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: 6267938
    Abstract: A method is provided for reducing the amount of hydrogen sulfide and organic sulfides present in streams, such as natural gas streams, by scrubbing the stream with a composition containing (i) an aqueous phase containing a reaction product resulting from the reaction between an aldehyde, such as formaldehyde, and a first amine, such as monoethanolamine or aminoethylpiperazine, and (ii) an organic phase containing at least a second amine, such as butylamine, pentylamine or hexylamine, to produce: (1) a stream having a diminished amount of sulfide contaminants and (2) a sulfided reaction product, such as trithiane. The sulfided reaction product is solubilized into the organic phase (which precludes the formation of solids), and this resulting sulfided reaction product-containing organic phase is separated from the aqueous phase. The sulfided reaction product-containing organic phase may be used as a corrosion inhibitor, and the composition has reduced foaming characteristics during the scrubbing step.
    Type: Grant
    Filed: November 4, 1996
    Date of Patent: July 31, 2001
    Assignee: Stanchem, Inc.
    Inventors: Neil Andrew Warrender, John Cossar
  • Patent number: 6242618
    Abstract: Invention relates to H2S scavengers polysulfide compounds and methods for scavenging H2S from polysulfide compounds. Furthermore, the invention uses a scavenger for selectively reducing the levels of hydrogen sulfide present in a polysulfide product.
    Type: Grant
    Filed: March 21, 2000
    Date of Patent: June 5, 2001
    Assignee: The Lubrizol Corporation
    Inventors: David R. Forester, Bharat B. Malik
  • Patent number: 6231755
    Abstract: The invention discloses a process for the desulfurization of petroleum products by contacting with acidic organic polymers. Preferably, highly fluorinated and, most preferably, perfluorinated acidic organic polymers are used.
    Type: Grant
    Filed: January 29, 1999
    Date of Patent: May 15, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Shaun Terrance Einar Mesher, Ralph Birchard Lloyd, Edward G. Howard
  • Patent number: 6224750
    Abstract: A process is disclosed for producing very low sulfur content hydrocarbon streams by contacting a hydrocarbon feedstream with an aqueous alkaline treatment stream which has been regenerated by the biological conversion of sulfur compounds to elemental sulfur. The process is characterized by the step of contacting the partially regenerated aqueous treatment stream with a hydrocarbon wash stream to remove low levels of residual elemental sulfur suspended in the partially regenerated treatment stream.
    Type: Grant
    Filed: October 19, 1999
    Date of Patent: May 1, 2001
    Assignee: UOP LLC
    Inventors: Rusty Mark Pittman, Blaise J. Arena
  • Patent number: 6214212
    Abstract: An improved process is provided for the chemical conversion and removal of hydrogen sulfide from gaseous and liquid streams by contacting a low temperature catalytically-active carbonaceous char capable of rapidly decomposing hydrogen peroxide in an aqueous solution with said stream.
    Type: Grant
    Filed: May 14, 1998
    Date of Patent: April 10, 2001
    Assignee: Calgon Carbon Corporation
    Inventors: Neal E. Megonnell, Robert H. Vaughn
  • Patent number: 6207043
    Abstract: Low-sulfur aliphatic compounds are obtained from olefin-rich starting materials contaminated with organic sulfur compounds.
    Type: Grant
    Filed: November 23, 1998
    Date of Patent: March 27, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Maximilian Vicari, Ekkehard Schwab, Marc Walter, Siegmar Maassen
  • Patent number: 6059962
    Abstract: A product of reduced sulfur content is produced in a multiple stage process from a feedstock which is comprised of a mixture of hydrocarbons and includes sulfur-containing aromatic compounds as unwanted impurities. The first stage involves: (1) subjecting the feedstock to alkylation conditions which are effective to convert a portion of the impurities to higher boiling sulfur-containing products, and (2) separating the resulting products by fractional distillation into a lower boiling fraction and a higher boiling fraction. The lower boiling fraction is comprised of hydrocarbons and is of reduced sulfur content relative to the feedstock. The higher boiling fraction is comprised of hydrocarbons and contains unconverted sulfur-containing aromatic impurities and also the higher boiling sulfur-containing products.
    Type: Grant
    Filed: September 9, 1998
    Date of Patent: May 9, 2000
    Assignee: BP Amoco Corporation
    Inventors: Bruce D. Alexander, George A. Huff, Vivek R. Pradhan, William J. Reagan, Roger H. Cayton
  • Patent number: 6048451
    Abstract: A product of reduced sulfur content is produced from a feedstock which is comprised of a mixture of hydrocarbons and contains organic sulfur compounds as unwanted impurities. The process comprises converting at least a portion of the sulfur-containing impurities to sulfur-containing products of higher boiling point by treatment with an alkylating agent in the presence of an acid catalyst and removing at least a portion of these higher boiling products by fractional distillation. Suitable alkylating agents include alcohols and olefins. In a preferred embodiment, catalytic cracking products which contain aromatic sulfur compounds as impurities are used as a feedstock for the process.
    Type: Grant
    Filed: January 14, 1997
    Date of Patent: April 11, 2000
    Assignee: BP Amoco Corporation
    Inventors: George A. Huff, Jr., Bruce D. Alexander, Douglas N. Rundell, William J. Reagan, Ozie S. Owen, Jin S. Yoo
  • Patent number: 6024866
    Abstract: Hydrocarbons, gas mixtures of hydrocarbons, and the like containing hydrogen sulfide are brought into intimate contact with a hydrogen sulfide scavenger prepared by reacting an alkylenepolyamine with formaldehyde, whereby the amount of hydrogen sulfide in the hydrocarbon is significantly reduced.
    Type: Grant
    Filed: October 19, 1993
    Date of Patent: February 15, 2000
    Assignee: Baker-Hughes Incorporated
    Inventors: Jerry J. Weers, Timothy J. O'Brien
  • Patent number: 5980845
    Abstract: The present invention generally provides sulfide scavenger solutions and processes that have high sulfide scavenging capacity, provide a reduction or elimination of solids formation and avoid the use of chemicals that pose environmental concerns. The invention utilizes a dialdehyde, preferably ethanedial, for the purpose of reacting with amines, amine carbonates, or other derivatives of amines that are liberated when certain scavenger solutions react with sulfides, including hydrogen sulfide and mercaptans. The scavenger solutions that have been discovered to liberate amines are those formed by a reaction between an amine and an aldehyde.
    Type: Grant
    Filed: May 6, 1997
    Date of Patent: November 9, 1999
    Inventor: Doyle Cherry
  • Patent number: 5968812
    Abstract: The invention relates to the unexpected discovery that the removal of the sulfinate group from an organosulfinate compound can be improved in the presence of an effective amount of a Lewis acid. The invention includes a method of removing the sulfinic acid functional group from an organosulfinic acid compound, comprising reacting the organosulfinic acid compound with an effective amount of a Lewis acid.
    Type: Grant
    Filed: February 2, 1998
    Date of Patent: October 19, 1999
    Assignee: Energy BioSystems Corporation
    Inventor: Gregory T. Mrachko
  • Patent number: 5958224
    Abstract: The instant invention is directed to a process for removing hard sulfurs from hydrocarbon streams by selectively oxidizing hard sulfurs in a hydrotreated stream, under oxidizing conditions in the presence of an effective amount of an oxidizing agent, wherein the oxidizing agent is a peroxometal complex and wherein the hard sulfurs are oxidized into the corresponding sulfoxides and sulfones.
    Type: Grant
    Filed: August 14, 1998
    Date of Patent: September 28, 1999
    Assignee: Exxon Research and Engineering Co
    Inventors: Teh Chung Ho, Chang Samuel Hsu, Gerald Dennis Dupre, Ronald Liotta, Viktor Buchholz
  • Patent number: 5863419
    Abstract: A product of reduced sulfur content is produced from a feedstock which is comprised of a mixture of hydrocarbons and contains organic sulfur compounds as unwanted impurities. The process comprises converting at least a portion of the sulfur-containing impurities to sulfur-containing products of higher boiling point by treatment with an alkylating agent in the presence of an acid catalyst and removing at least a portion of these higher boiling products by fractional distillation. The process can be carried out in a distillation column reactor wherein the acid catalyzed reaction and fractional distillation are carried out simultaneously. Suitable alkylating agents include alcohols and olefins.
    Type: Grant
    Filed: August 18, 1997
    Date of Patent: January 26, 1999
    Assignee: Amoco Corporation
    Inventors: George A. Huff, Jr., Ozie S. Owen, Bruce D. Alexander, Douglas N. Rundell, William J. Reagan, Jin S. Yoo
  • Patent number: 5858212
    Abstract: A hydrocarbon stream containing sulfur and sulfur compounds is contacted with a water suspension of dolomitic lime and dibasic acid catalyst in a reaction vessel in order to transfer the sulfur and sulfur compounds from the petroleum vapor to the water phase. During sulfur removal, naphthenic acid present in the hot petroleum vapor is converted to a high quality naphtha fraction. In the water phase, the sulfur compounds react with the available alkalinity from the dolomitic lime and dibasic acid. The insoluble calcium or magnesium based reaction products can then be removed from the water phase through conventional solids concentrating and separating equipment.
    Type: Grant
    Filed: July 3, 1996
    Date of Patent: January 12, 1999
    Assignee: InterGlobal Desulfuruzations Systems, Inc.
    Inventor: John J. Darcy
  • Patent number: 5753102
    Abstract: The present invention provides a process and equipment for efficiently and economically recovering organic sulfur compounds in a fuel oil while maintaining the original chemical structures thereof. The fuel oil is admixed with a solvent low in solubility therein of hydrocarbons and high in solubility therein of organic sulfur compounds to effect migration of the organic sulfur compounds in the fuel oil into the solvent by making much of the nucleophilic properties of a lone pair of electrons on a bivalent sulfur atom of a sulfur-containing functional group, followed by fuel oil-solvent separation by settling out or with a centrifugal force.
    Type: Grant
    Filed: October 3, 1995
    Date of Patent: May 19, 1998
    Assignee: Izumi Funakoshi
    Inventors: Izumi Funakoshi, Tetsuo Aida
  • Patent number: 5744024
    Abstract: Reaction of 1,3,5-tri-substituted-hexahydro-1,3,5-triazine is accelerated in H.sub.2 S scavenging by the addition of quaternary ammonium compound. The preferred hexahydro triazines are 1,3,5-tri-methyl-hexahydro-1,3,5-triazines and 1,3,5-tri-methoxypropyl-hexahydro-1,3,5-triazines. The blend of the hexahydro triazine and quaternary ammonium compounds can be used to treat sour gases and liquids (e.g. sour kerosene, crude oil, fuel oils, heating oils, distillate fuels, bunker fuel oil, and the like.
    Type: Grant
    Filed: October 12, 1995
    Date of Patent: April 28, 1998
    Assignee: Nalco/Exxon Energy Chemicals, L.P.
    Inventors: Daniel S. Sullivan, III, Allan R. Thomas, Juan M. Garcia, III, Paul Yon-Hin
  • Patent number: 5689033
    Abstract: A process is directed to the removal of impurities such as sulfur compounds, oxygenates, and/or olefins from a light paraffin hydrocarbon feedstock such as a C.sub.4 -C.sub.6 fraction, which may be used subsequently in an isomerization process in an integrated complex for the production of ethers such as MTBE and TAME. The hydrocarbon feedstream is passed to a removal zone wherein the hydrocarbon feedstream is contacted with a selective solvent for the removal of the impurities comprising at least one of sulfur compounds, oxygenates and olefins to provide a rich solvent stream and a treated hydrocarbon stream. The rich solvent comprising the trace impurities is contacted with a stripping medium stream to regenerate the selective solvent in a stripping zone. The removal zone may be a liquid-liquid extraction zone or a gas absorption zone.
    Type: Grant
    Filed: May 2, 1996
    Date of Patent: November 18, 1997
    Assignee: UOP
    Inventors: Paulino Forte, Stanley J. Frey
  • Patent number: 5582714
    Abstract: A process is disclosed for the removal of sulfur from petroleum fractions such as FCC gasoline by employing a solvent selected from the group consisting of a polyalkylene glycol, polyalkylene glycol ether, and mixtures thereof and having a molecular weight less than 400. The process is useful for saving energy, saving hydrogen consumption, and retaining octane. By requiring only the mild hydrotreatment of an extracted or absorbed stream concentrated with the sulfur impurities, the sulfur impurities are removed without the loss of octane resulting from conversion of either high octane olefins or aromatic components. In addition, the extract stream is a significantly smaller stream than the original feedstream.
    Type: Grant
    Filed: March 20, 1995
    Date of Patent: December 10, 1996
    Assignee: UOP
    Inventor: Paulino Forte
  • Patent number: 5552060
    Abstract: The present invention provides a method for scavenging H.sub.2 S from aqueous and hydrocarbon substrates using an epoxide. Preferred epoxides are styrene oxide, 1,3-butadiene diepoxide, and cyclohexene oxide.
    Type: Grant
    Filed: May 5, 1995
    Date of Patent: September 3, 1996
    Assignee: Baker Hughes Incorporated
    Inventor: Glenn L. Roof
  • Patent number: 5552036
    Abstract: This invention relates to a process for reducing the sulfur in a refinery process stream and/or crude oil, which comprises treating said refinery process stream and/or crude oil with an effective sulfur reducing amount of a reducing agent selected from the group consisting of hydrazine, oximes, hydroxylamines, carbohydrazide, erythorbic acid, and mixtures thereof wherein the reducing agent or the hydrocarbon treated has a temperature of at least 50.degree. C.
    Type: Grant
    Filed: June 1, 1994
    Date of Patent: September 3, 1996
    Inventors: Todd L. Foret, William D. Mansfield, Hubert P. Vidrine
  • Patent number: 5529930
    Abstract: A method for reducing the viscosity of viscous petroleum liquids, such as heavy crude oil and bitumen, is disclosed. The method is appropriate for use with viscous petroleum liquids that contain sulfur-bearing heterocycles, the physicochemical properties of the heterocycles contributing significantly to the viscosity of the liquid. The method comprises contacting the viscous petroleum liquid with a biocatalyst that converts sulfur-bearing heterocycles into molecules that lack physicochemical properties condusive to viscosity. The biocatalyst works in a sulfur-specific manner, such that the sulfur-bearing heterocycle is altered at the sulfur heteroatom thereof. Through biocatalysis, carbon-sulfur bonds are cleaved and/or polar substituents such as hydroxyl groups are joined to the sulfur heteroatom, the hydrocarbon framework of the sulfur-bearing heterocycle, or both. Preferred biocatalysts for viscosity reduction include preparations of Rhodococcus rhodochrous ATCC No.
    Type: Grant
    Filed: May 28, 1993
    Date of Patent: June 25, 1996
    Assignee: Energy BioSystems Corporation
    Inventors: Daniel J. Monticello, William M. Haney, III
  • Patent number: 5496729
    Abstract: This invention relates to an integrated method for the desulfurization and desalting of a fossil fuel, comprising the steps of: (a) contacting a fossil fuel with; (i) a sufficient amount of an aqueous solution capable of depleting the fossil fuel of forms of water soluble salt contaminants; and (ii) an effective amount of a biocatalyst capable of depleting the fossil fuel of forms of sulfur-bearing organic molecules; (b) incubating the above mixture whereby; (i) the fossil fuel is significantly depleted of forms of water soluble salt contaminants; and (ii) the biocatalytic agent selectively catalyzes carbon-sulfur bonds in sulfur-bearing organic molecules generating a significant amount of water-soluble inorganic sulfur molecules; both reactions occurring without depleting the fossil fuel of combustible organic molecules; and (c) separating the aqueous component from the fossil fuel component, the fossil fuel now being significantly reduced in sulfur and salt contamination and the aqueous component now being
    Type: Grant
    Filed: August 31, 1994
    Date of Patent: March 5, 1996
    Assignee: Energy BioSystems Corporation
    Inventor: Daniel J. Monticello
  • Patent number: 5494572
    Abstract: This process for the desulfurization and denitration of light oil is effected by extraction with an organic solvent containing nitrogen. The invention also relates to light oil desulfurized and denitrated by said process as well as an organic solvent containing nitrogen for the extraction. The solvent is selected from among, for example, hetrocyclic compounds containing nitrogen, such as pyrrolidones, imidazolidinones, pyrimidinones and pyridinium salts, and acid amides. The combination of the process of this invention with any ordinary process for hydrodesulfurization enables the production of light oil having a sulfur content not exceeding 0.01% by weight. Light oil still containing benzothiophenone and dibenzothiophenone derivatives after hydrodesulfurization can be easily desulfurized to yield a desulfurized product not having any undesirable color, or any offensive smell. Also, the extraction of nitrogen compounds and aromatic compound from light oil is effected by the same process.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: February 27, 1996
    Assignee: General Sekiyu Kabushikikaisha
    Inventors: Yuji Horii, Hitoshi Onuki, Sadaaki Doi, Toshiatsu Mori, Takeo Takatori, Hideaki Sato, Tsuyoshi Ookuro, Toru Sugawara
  • Patent number: 5472875
    Abstract: A continuous cyclic process for desulfurizing a petroleum liquid which contains organic sulfur molecules, a significant portion of which are comprised of sulfur-bearing heterocycles. This process involves oxygenating the petroleum liquid and treating it with a biocatalyst capable of catalyzing the sulfur-specific oxidative cleavage of organic carbon-sulfur bonds in sulfur-bearing aromatic heterocyclic molecules such as dibenzothiophene. a particularly preferred biocatalyst is a culture of mutant Rhodococcous rhodocrous bacteria, ATCC No. 53968. In the present process, the activity of this biocatalyst is regenerated; it can be used for many cycles of treatment. A system for conducting the continuous cyclic process of biocatalytic desulfurization of petroleum liquids is also disclosed.
    Type: Grant
    Filed: October 12, 1993
    Date of Patent: December 5, 1995
    Assignee: Energy BioSystems Corporation
    Inventor: Daniel J. Monticello
  • Patent number: 5462721
    Abstract: The levels of hydrogen sulfide and organic sulfides present in gaseous or liquid hydrocarbon streams or mixtures thereof are reduced by contacting the streams with a composition comprising the reaction product of aminoethylpiperazine, an alkanolamine, an etheramine, a polyalkyleneamine, or a polyoxyalkyleneamine with a C1 to C4 aldehyde, including monoaldehydes and dialdehydes, such as ethandial. The solubility of polyamine/aldehyde reaction products is increased by the presence of an enchancing amine/aldehyde reaction product. The enhancing amines include alkanolamines, etheramines, and mixtures thereof.
    Type: Grant
    Filed: December 7, 1994
    Date of Patent: October 31, 1995
    Assignee: Crescent Holdings Limited
    Inventors: Russell Pounds, Doyle Cherry
  • Patent number: 5356813
    Abstract: This invention relates to an integrated method for the desulfurization and desalting of a fossil fuel, comprising the steps of: (a) contacting a fossil fuel with; (i) a sufficient amount of an aqueous solution capable of depleting the fossil fuel of forms of water soluble salt contaminants; and (ii) an effective amount of a biocatalyst capable of depleting the fossil fuel of forms of sulfur-bearing organic molecules; (b) incubating the above mixture whereby; (i) the fossil fuel is significantly depleted of forms of water soluble salt contaminants; and (ii) the biocatalytic agent selectively catalyzes carbon-sulfur bonds in sulfur-bearing organic molecules generating a significant amount of water-soluble inorganic sulfur molecules; both reactions occurring without depleting the fossil fuel of combustible organic molecules; and (c) separating the aqueous component from the fossil fuel component, the fossil fuel now being significantly reduced in sulfur and salt contamination and the aqueous component now being
    Type: Grant
    Filed: April 30, 1992
    Date of Patent: October 18, 1994
    Assignee: Energy BioSystems Corporation
    Inventor: Daniel J. Monticello
  • Patent number: 5354453
    Abstract: Reactive S (e.g. H.sub.2 S and mercaptans) in petroleum liquid are scavenged by the use of oil soluble trialkyl hexahydro triazines wherein at least one alkyl group, and preferably all three, contain from 7 to 20 carbon atoms.
    Type: Grant
    Filed: April 13, 1993
    Date of Patent: October 11, 1994
    Assignee: Exxon Chemical Patents Inc.
    Inventor: Kishan Bhatia
  • Patent number: 5346614
    Abstract: A method and system for removing hydrogen sulfide from a continuous aqueous phase-containing fluid without forming a sulfur sludge. Oil is either initially present in the fluid or added thereto.
    Type: Grant
    Filed: November 10, 1992
    Date of Patent: September 13, 1994
    Assignee: Union Oil Company of California
    Inventors: Christohper R. Culver, Clifford D. Juengst
  • Patent number: 5344555
    Abstract: Sour sulfhydryl group containing oils are treated with an effective amount of a sweetening, hydrogen sulfide vapor reducing quaternary ammonium compound of the formula ##STR1## (a) wherein (i) R.sup.1, R.sup.2 and R.sup.3 are hydrocarbon groups including alkyl, aryl, alkaryl or arylalkyl groups, of up to 24 carbon atoms, and if an alkyl group, may include a cycloalkyl; with the proviso that two of R.sup.1, R.sup.2 and R.sup.3 may be in saturated heterocyclic ring which includes said nitrogen atom and may also include an oxygen atom; and (ii) at least one of R.sup.1, R.sup.2 and R.sup.3 has two or more carbon atoms; and (b) wherein R.sup.4, R.sup.5, R.sup.6 and R.sup.7 independently are hydrogen or a hydrocarbon group of up to six carbon atoms, with the proviso that two of R.sup.4, R.sup.5, R.sup.6 and R.sup.7 may be in a cycloalkane ring. The compounds used in this treatment are especially suitable for high boiling, heavy residual fuels under low mix conditions.
    Type: Grant
    Filed: February 22, 1993
    Date of Patent: September 6, 1994
    Assignee: Baker Hughes Incorporated
    Inventors: Glenn L. Roof, Lawrence N. Kremer, Robert V. Market