With Organic Reagent Patents (Class 208/237)
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Patent number: 6733660Abstract: 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: GrantFiled: July 31, 2001Date of Patent: May 11, 2004Assignee: BP Corporation North America Inc.Inventors: Vivek R. Pradhan, Ptoshia A. Burnett, Stacey McDaniel, Michael Hodges
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Publication number: 20040079680Abstract: 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: ApplicationFiled: October 23, 2002Publication date: April 29, 2004Applicant: SulphCo., Inc.Inventor: Rudolf W. Gunnerman
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Patent number: 6726835Abstract: 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: GrantFiled: December 17, 2002Date of Patent: April 27, 2004Assignee: UOP LLCInventors: Gavin P. Towler, Michael A. Schultz
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Publication number: 20040019248Abstract: 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: ApplicationFiled: June 6, 2003Publication date: January 29, 2004Applicant: Baker Hughes IncorporatedInventors: Joseph L. Stark, Robert S. Lauer, Lawrence N. Kremer
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Patent number: 6638419Abstract: 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: GrantFiled: January 10, 2002Date of Patent: October 28, 2003Assignee: Total Raffinage Distribution S.A.Inventors: Pedro Da Silva, RaphaĆ«l Le Gall
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Publication number: 20030116474Abstract: 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: ApplicationFiled: December 17, 2002Publication date: June 26, 2003Inventors: Gavin P. Towler, Michael A. Schultz
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Publication number: 20030089641Abstract: 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: ApplicationFiled: November 8, 2002Publication date: May 15, 2003Applicant: Clearwater International LLC.Inventor: Larry W. Gatlin
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Patent number: 6540907Abstract: 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: GrantFiled: July 9, 2001Date of Patent: April 1, 2003Assignee: UOP LLCInventors: Gavin P. Towler, Michael A. Schultz
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Publication number: 20030057136Abstract: 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: ApplicationFiled: August 20, 2002Publication date: March 27, 2003Inventors: Kenneth E. McIntush, Ken DeBerry, David W. DeBerry
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Patent number: 6531103Abstract: 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: GrantFiled: March 9, 2000Date of Patent: March 11, 2003Assignee: Union Carbide Chemicals and Plastics Technology CorporationInventors: Leo Ernest Hakka, Paulino Forte
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Publication number: 20030029776Abstract: 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: ApplicationFiled: July 31, 2001Publication date: February 13, 2003Inventors: Vivek R. Pradhan, Ptoshia A. Burnett, Stacey McDaniel, Michael Hodges
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Patent number: 6488840Abstract: This invention relates to reducing the amount of thiols (mercaptans) in petroleum streams, specifically, mercaptans above the five carbon molecular weight range.Type: GrantFiled: April 18, 2000Date of Patent: December 3, 2002Assignee: ExxonMobil Research and Engineering CompanyInventors: Mark Alan Greaney, Michael Charles Kerby, Roby Bearden, Jr.
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Patent number: 6483003Abstract: 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: GrantFiled: November 2, 2000Date of Patent: November 19, 2002Assignee: Sasol Technology (Proprietary) LimitedInventors: Waldo Eugene De Villiers, Petra De Wet, Magdalena Catharina Hough-Langanke, Hubert Naude, Atool Govan Pema
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Publication number: 20020166799Abstract: 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: ApplicationFiled: March 26, 2001Publication date: November 14, 2002Applicant: COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCHInventors: 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
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Publication number: 20020157989Abstract: 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 substratesType: ApplicationFiled: April 23, 2002Publication date: October 31, 2002Applicant: Clearwater, Inc.Inventors: Larry W. Gatlin, Wayne Mueller
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Patent number: 6444117Abstract: 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: GrantFiled: August 16, 2000Date of Patent: September 3, 2002Assignee: Texaco, Inc.Inventors: M. Rashid Khan, Vincent P. Nero, Lee Ann Brugger, Stephen J. DeCanio, David A. Storm
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Patent number: 6406616Abstract: 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: GrantFiled: September 12, 2001Date of Patent: June 18, 2002Assignee: Unipure CorporationInventors: Alkis S. Rappas, Vincent P. Nero, Stephen J. DeCanio
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Patent number: 6402940Abstract: 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: GrantFiled: September 1, 2000Date of Patent: June 11, 2002Assignee: Unipure CorporationInventor: Alkis S. Rappas
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Patent number: 6358402Abstract: 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: GrantFiled: December 28, 1999Date of Patent: March 19, 2002Assignee: ExxonMobil Research and Engineering CompanyInventor: Robert C. Schucker
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Publication number: 20020029997Abstract: 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: ApplicationFiled: September 12, 2001Publication date: March 14, 2002Applicant: UniPure CorporationInventors: Alkis S. Rappas, Vincent P. Nero, Stephen J. DeCanio
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Patent number: 6352640Abstract: The invention describes a method for preparing a low sulfur motor gasoline utilizing ethanol and caustic extraction.Type: GrantFiled: April 18, 2000Date of Patent: March 5, 2002Assignee: ExxonMobil Research and Engineering CompanyInventors: Bruce Randall Cook, Richard Harry Ernst, Mark Alan Greaney
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Patent number: 6267938Abstract: 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: GrantFiled: November 4, 1996Date of Patent: July 31, 2001Assignee: Stanchem, Inc.Inventors: Neil Andrew Warrender, John Cossar
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Patent number: 6242618Abstract: 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: GrantFiled: March 21, 2000Date of Patent: June 5, 2001Assignee: The Lubrizol CorporationInventors: David R. Forester, Bharat B. Malik
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Patent number: 6231755Abstract: 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: GrantFiled: January 29, 1999Date of Patent: May 15, 2001Assignee: E. I. du Pont de Nemours and CompanyInventors: Shaun Terrance Einar Mesher, Ralph Birchard Lloyd, Edward G. Howard
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Patent number: 6224750Abstract: 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: GrantFiled: October 19, 1999Date of Patent: May 1, 2001Assignee: UOP LLCInventors: Rusty Mark Pittman, Blaise J. Arena
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Patent number: 6214212Abstract: 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: GrantFiled: May 14, 1998Date of Patent: April 10, 2001Assignee: Calgon Carbon CorporationInventors: Neal E. Megonnell, Robert H. Vaughn
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Patent number: 6207043Abstract: Low-sulfur aliphatic compounds are obtained from olefin-rich starting materials contaminated with organic sulfur compounds.Type: GrantFiled: November 23, 1998Date of Patent: March 27, 2001Assignee: BASF AktiengesellschaftInventors: Maximilian Vicari, Ekkehard Schwab, Marc Walter, Siegmar Maassen
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Patent number: 6059962Abstract: 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: GrantFiled: September 9, 1998Date of Patent: May 9, 2000Assignee: BP Amoco CorporationInventors: Bruce D. Alexander, George A. Huff, Vivek R. Pradhan, William J. Reagan, Roger H. Cayton
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Patent number: 6048451Abstract: 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: GrantFiled: January 14, 1997Date of Patent: April 11, 2000Assignee: BP Amoco CorporationInventors: George A. Huff, Jr., Bruce D. Alexander, Douglas N. Rundell, William J. Reagan, Ozie S. Owen, Jin S. Yoo
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Patent number: 6024866Abstract: 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: GrantFiled: October 19, 1993Date of Patent: February 15, 2000Assignee: Baker-Hughes IncorporatedInventors: Jerry J. Weers, Timothy J. O'Brien
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Patent number: 5980845Abstract: 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: GrantFiled: May 6, 1997Date of Patent: November 9, 1999Inventor: Doyle Cherry
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Patent number: 5968812Abstract: 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: GrantFiled: February 2, 1998Date of Patent: October 19, 1999Assignee: Energy BioSystems CorporationInventor: Gregory T. Mrachko
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Patent number: 5958224Abstract: 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: GrantFiled: August 14, 1998Date of Patent: September 28, 1999Assignee: Exxon Research and Engineering CoInventors: Teh Chung Ho, Chang Samuel Hsu, Gerald Dennis Dupre, Ronald Liotta, Viktor Buchholz
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Patent number: 5863419Abstract: 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: GrantFiled: August 18, 1997Date of Patent: January 26, 1999Assignee: Amoco CorporationInventors: George A. Huff, Jr., Ozie S. Owen, Bruce D. Alexander, Douglas N. Rundell, William J. Reagan, Jin S. Yoo
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Patent number: 5858212Abstract: 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: GrantFiled: July 3, 1996Date of Patent: January 12, 1999Assignee: InterGlobal Desulfuruzations Systems, Inc.Inventor: John J. Darcy
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Patent number: 5753102Abstract: 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: GrantFiled: October 3, 1995Date of Patent: May 19, 1998Assignee: Izumi FunakoshiInventors: Izumi Funakoshi, Tetsuo Aida
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Patent number: 5744024Abstract: 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: GrantFiled: October 12, 1995Date of Patent: April 28, 1998Assignee: Nalco/Exxon Energy Chemicals, L.P.Inventors: Daniel S. Sullivan, III, Allan R. Thomas, Juan M. Garcia, III, Paul Yon-Hin
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Patent number: 5689033Abstract: 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: GrantFiled: May 2, 1996Date of Patent: November 18, 1997Assignee: UOPInventors: Paulino Forte, Stanley J. Frey
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Patent number: 5582714Abstract: 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: GrantFiled: March 20, 1995Date of Patent: December 10, 1996Assignee: UOPInventor: Paulino Forte
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Patent number: 5552060Abstract: 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: GrantFiled: May 5, 1995Date of Patent: September 3, 1996Assignee: Baker Hughes IncorporatedInventor: Glenn L. Roof
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Patent number: 5552036Abstract: 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: GrantFiled: June 1, 1994Date of Patent: September 3, 1996Inventors: Todd L. Foret, William D. Mansfield, Hubert P. Vidrine
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Patent number: 5529930Abstract: 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: GrantFiled: May 28, 1993Date of Patent: June 25, 1996Assignee: Energy BioSystems CorporationInventors: Daniel J. Monticello, William M. Haney, III
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Patent number: 5496729Abstract: 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 beingType: GrantFiled: August 31, 1994Date of Patent: March 5, 1996Assignee: Energy BioSystems CorporationInventor: Daniel J. Monticello
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Patent number: 5494572Abstract: 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: GrantFiled: June 2, 1995Date of Patent: February 27, 1996Assignee: General Sekiyu KabushikikaishaInventors: Yuji Horii, Hitoshi Onuki, Sadaaki Doi, Toshiatsu Mori, Takeo Takatori, Hideaki Sato, Tsuyoshi Ookuro, Toru Sugawara
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Patent number: 5472875Abstract: 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: GrantFiled: October 12, 1993Date of Patent: December 5, 1995Assignee: Energy BioSystems CorporationInventor: Daniel J. Monticello
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Patent number: 5462721Abstract: 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: GrantFiled: December 7, 1994Date of Patent: October 31, 1995Assignee: Crescent Holdings LimitedInventors: Russell Pounds, Doyle Cherry
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Patent number: 5356813Abstract: 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 beingType: GrantFiled: April 30, 1992Date of Patent: October 18, 1994Assignee: Energy BioSystems CorporationInventor: Daniel J. Monticello
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Patent number: 5354453Abstract: 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: GrantFiled: April 13, 1993Date of Patent: October 11, 1994Assignee: Exxon Chemical Patents Inc.Inventor: Kishan Bhatia
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Patent number: 5346614Abstract: 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: GrantFiled: November 10, 1992Date of Patent: September 13, 1994Assignee: Union Oil Company of CaliforniaInventors: Christohper R. Culver, Clifford D. Juengst
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Patent number: 5344555Abstract: 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: GrantFiled: February 22, 1993Date of Patent: September 6, 1994Assignee: Baker Hughes IncorporatedInventors: Glenn L. Roof, Lawrence N. Kremer, Robert V. Market