With Acids Patents (Class 208/219)
  • Patent number: 9127214
    Abstract: A fuel desulfurization method where in the step (a), a fuel is oxidized by adding an ionic liquid, an oxidant, and an acid catalyst. In the step (b), the oxidized fuel is mixed with a desulfurization agent to form a desulfurized fuel. In the step (c), the ionic liquid is recycled. In the recycling step, a first solution is added into the ionic liquid. Then, a second solution is added into the ionic liquid to form a second solution phase and an ionic liquid phase. The second solution phase is separated from the ionic liquid phase. The first solution, the oxidant and the acid catalyst are removed from the remained ionic liquid phase to form a recycled ionic liquid.
    Type: Grant
    Filed: February 5, 2013
    Date of Patent: September 8, 2015
    Inventors: Shun-Sheng Cheng, Teh-Jung Lin
  • Publication number: 20150060334
    Abstract: Methods and apparatuses for processing hydrocarbon streams containing organic nitrogen species are provided. In an embodiment, a method for processing a hydrocarbon stream containing organic nitrogen species includes adding an aqueous acidic solution to a hydrocarbon feed stream to form a reaction stream. The method further includes contacting the reaction stream with a reaction surface and reacting the aqueous acidic solution and the organic nitrogen species to form an ammonium sulfate rich stream and a lean nitrogen naphtha stream. Also, the method includes separating an ammonium sulfate rich aqueous phase and an oil phase from the ammonium sulfate rich stream.
    Type: Application
    Filed: August 30, 2013
    Publication date: March 5, 2015
    Applicant: UOP LLC
    Inventor: Steven F. Zink
  • Patent number: 8894843
    Abstract: A method of upgrading a heteroatom-containing hydrocarbon feed by removing heteroatom contaminants is disclosed. The method includes contacting the heteroatom-containing hydrocarbon feed with an oxidant and an immiscible acid to oxidize the heteroatoms, contacting the oxidized- heteroatom-containing hydrocarbon feed with caustic and a selectivity promoter, and removing the heteroatom contaminants from the heteroatom-containing hydrocarbon feed. The oxidant may be used in the presence of a catalyst.
    Type: Grant
    Filed: June 11, 2012
    Date of Patent: November 25, 2014
    Assignee: Auterra, Inc.
    Inventors: Jonathan P. Rankin, Jennifer L. Vreeland, Kyle E. Litz, Tracey M. Jordan, Mark N. Rossetti, Eric H. Burnett, Trent A. McCaskill
  • Patent number: 8778172
    Abstract: The invention is related to hydrogen sulfide scavenging additive, capable of scavenging hydrogen sulfide in hydrocarbons by forming water soluble scavenged products which are capable of getting separated from hydrocarbon even at acidic pH without causing fouling and decomposition problems, consisting of aldehyde or aldehyde and polyethylene glycol [PEG], and wherein said aldehyde is glyoxylic acid. The invention is also related to a method of scavenging hydrogen sulfide employing present scavenging additive.
    Type: Grant
    Filed: May 3, 2010
    Date of Patent: July 15, 2014
    Assignee: Dorf Ketal Chemicals (I) Private Limited
    Inventor: Mahesh Subramaniyam
  • Publication number: 20130075305
    Abstract: The present invention provides selective extraction of sulfoxides, or sulfoxides in combination with sulfones, from hydrocarbon mixtures containing these compounds. A significant advantage of the invention is that oxidation products resulting from oxidative desulfurization of hydrocarbon feedstocks are selectively extracted with minimum co-extraction of non-oxidized products such as valuable hydrocarbon fuel components.
    Type: Application
    Filed: September 26, 2012
    Publication date: March 28, 2013
    Applicant: SAUDI ARABIAN OIL COMPANY
    Inventor: Saudi Arabian Oil Company
  • Patent number: 8298404
    Abstract: A reaction system and method for removing heteroatoms from oxidized-heteroatom-containing hydrocarbon streams and products derived therefrom are disclosed. An oxidized-heteroatom-containing hydrocarbon feed is reacted in a reaction system thereby forming non-ionic hydrocarbon products. The products derived therefrom are useful as transportation fuels, lubricants, refinery intermediates, or refinery feeds.
    Type: Grant
    Filed: September 22, 2010
    Date of Patent: October 30, 2012
    Assignee: Auterra, Inc.
    Inventors: Kyle E. Litz, Jennifer L. Vreeland, Jonathan P. Rankin, Thomas W. DeLancey, Timothy A. Thompson
  • Patent number: 8287721
    Abstract: A method for reducing asphaltene and paraffin content in oil material for recuperating and improving production of heavy, medium and light crude oils by reducing asphaltene and paraffin content in crude oil and oil-containing tar sands; and schist and clay for recuperation of exposed oxidized oil; and tar petroleum, schist petroleum, and clay petroleum, whereby a molecule elimination process of very polymerized hydrocarbons, including asphaltene and paraffin, are responsible for medium, heavy and extra heavy crude oil poor properties, as well as the difficult recuperation of most high containing long chain asphaltene and paraffin light crude oils, resulting in the production of more light and short hydrocarbon chains to greatly reduce viscosity, thus facilitating its recuperation and transportation.
    Type: Grant
    Filed: August 30, 2010
    Date of Patent: October 16, 2012
    Inventors: Lucinda Paris-Marcano, Maria Borjas-Garcia
  • Patent number: 8246813
    Abstract: The invention provides a method of removing sulfides from viscous petroleum streams such as asphalt, crude oil, and oil slurry using zinc octoate in which the molar ratio of zinc complexed with octanoic acid is not 1:2. Because zinc has a +2 charge and carboxylic acid has a ?1 charge, it was previously assumed that all zinc octoates must have a 1:2 ratio of zinc moieties to carboxylic acid. Zinc octoate formulations however, that contain a non 1:2 ratio, and those with 2.1:3 to 1.97:3 in particular, have in fact been shown to work better. In addition, these non 1:2 formulations have lower viscosity and therefore are easier to use than the previous formulations including a 1:2 ratio.
    Type: Grant
    Filed: December 15, 2009
    Date of Patent: August 21, 2012
    Assignee: Nalco Company
    Inventors: Dennis R. Compton, Samuel Jefferies, Ron Sharpe
  • Patent number: 8241490
    Abstract: A method of upgrading a heteroatom-containing hydrocarbon feed by removing heteroatom contaminants is disclosed. The method includes contacting the heteroatom-containing hydrocarbon feed with an oxidant to oxidize the heteroatoms, contacting the oxidized-heteroatom-containing hydrocarbon feed with caustic and a selectivity promoter, and removing the heteroatom contaminants from the heteroatom-containing hydrocarbon feed. The oxidant may be used in the presence of a catalyst.
    Type: Grant
    Filed: October 14, 2010
    Date of Patent: August 14, 2012
    Assignee: Auterra, Inc.
    Inventors: Kyle E. Litz, Jennifer L. Vreeland, Jonathan P. Rankin, Mark N. Rossetti, Tracey M. Jordan
  • Patent number: 8197671
    Abstract: A method of upgrading a heteroatom-containing hydrocarbon feed by removing heteroatom contaminants is disclosed. The method includes contacting the heteroatom-containing hydrocarbon feed with an oxidant and an immiscible acid to oxidize the heteroatoms, contacting the oxidized-heteroatom-containing hydrocarbon feed with caustic and a selectivity promoter, and removing the heteroatom contaminants from the heteroatom-containing hydrocarbon feed. The oxidant may be used in the presence of a catalyst.
    Type: Grant
    Filed: December 23, 2010
    Date of Patent: June 12, 2012
    Assignee: Auterra, Inc.
    Inventors: Jonathan P. Rankin, Jennifer L. Vreeland, Kyle E. Litz, Tracey M. Jordan, Mark N. Rossetti, Eric H. Burnett
  • Publication number: 20120055848
    Abstract: The invention is related to hydrogen sulfide scavenging additive, capable of scavenging hydrogen sulfide in hydrocarbons by forming water soluble scavenged products which are capable of getting separated from hydrocarbon even at acidic pH without causing fouling and decomposition problems, consisting of aldehyde or aldehyde and polyethylene glycol [PEG], and wherein said aldehyde is glyoxylic acid. The invention is also related to a method of scavenging hydrogen sulfide employing present scavenging additive.
    Type: Application
    Filed: May 3, 2010
    Publication date: March 8, 2012
    Applicant: DORF KETAL CHEMICALS (I) PRIVATE LIMITED
    Inventor: Mahesh Subramaniyam
  • Patent number: 8048175
    Abstract: Mercaptans and/or hydrogen sulfide (H2S) in hydrocarbons, naphthas, gasolines, and the like may be scavenged therefrom by being brought into intimate contact with a mercaptan scavenger formulation containing at least one disubstituted azodicarboxylate of the formula R1OOCN?NCOOR2, where R1 and R2 are independently alkyl groups, alkenyl groups and aromatic groups having from 1 to 18 carbon atoms. These scavengers remove mercaptans and/or H2S from hydrocarbons faster than many conventional mercaptan scavengers. An effective scavenging amount of disubstituted azodicarboxylate in the hydrocarbon fluid ranges from about 5 to about 20 parts by weight based on 1 part as sulfur of mercaptan and/or H2S.
    Type: Grant
    Filed: April 8, 2009
    Date of Patent: November 1, 2011
    Assignee: Baker Hughes Incorporated
    Inventors: Jianzhong Yang, Joseph J. Arensdorf, Melanie V. Barker
  • Patent number: 8021540
    Abstract: A method of desulfurizing/refining a hydrocarbon oil by which sulfur compounds are diminished to an extremely low concentration at a relatively low equipment cost and operating cost. The method of desulfurizing/refining a hydrocarbon oil comprises bringing a hydrocarbon oil containing at least one sulfur compound selected from the group consisting of thiophene compounds, benzothiophene compounds, and dibenzothiophene compounds and optionally further containing aromatic hydrocarbons into contact with a solid acid catalyst and/or an activated carbon having a transition metal oxide supported thereon to thereby desulfurize the oil. The solid acid catalyst preferably is a solid ultrastrong-acid catalyst selected among sulfuric acid radical/zirconia, sulfuric acid radical/alumina, sulfuric acid radical/tin oxide, sulfuric acid radical/iron oxide, tungstic acid/zirconia, and tungstic acid/tin oxide.
    Type: Grant
    Filed: January 27, 2005
    Date of Patent: September 20, 2011
    Assignee: Japan Energy Corporation
    Inventor: Yasuhiro Toida
  • Patent number: 8002971
    Abstract: Processes and systems associated with hydrodynamic cavitation-catalyzed oxidation of sulfur-containing substances in a fluid are described. In one example method, carbonaceous fluid is combined with at least one oxidant to form a mixture and then the mixture is flowed through at least one local constriction in a flow-through chamber at a sufficient pressure and flow rate to create hydrodynamic cavitation in the flowing mixture having a power density of between about 3,600 kWatts/cm2 and about 56,000 kWatts/cm2 measured at the surface of the local constriction normal to the direction of fluid flow. The creation of hydrodynamic cavitation in the flowing mixture initiates one or more chemical reactions that, at least in part, oxidize at least some of the sulfur-containing substances in the carbonaceous fluid.
    Type: Grant
    Filed: June 9, 2008
    Date of Patent: August 23, 2011
    Assignee: Arisdyne Systems, Inc.
    Inventor: Oleg V. Kozyuk
  • Patent number: 7947166
    Abstract: The present invention relates to a method for treating a feed corresponding to a pyrolysis gasoline, comprising: a) at least one stage of selective hydrogenation of the feed, referred to as HD1, b) fractionating in one or more distillation columns the effluent from stage a) in order to produce at least one light C5 cut, an intermediate C6 or C6-C7 or C6-C8 cut intended for aromatics production, a heavy C7+ or C8+ or C9+ cut intended for gasoline production, c) at least one stage of hydrodesulfurization and deep hydrogenation of the intermediate cut, referred to as HD2, d) at least one stage of alkylation of the heavy C7+, C8+ or C9+ cut consisting of a treatment on an acid catalyst allowing weighting of the sulfur compounds, e) at least one stage of distillation of the effluent from stage d), intended to produce a light fraction that can be directly used as a low-sulfur gasoline base, and a heavy C11+ or C12+ fraction rich in sulfur compounds, used as middle distillate or fuel oil.
    Type: Grant
    Filed: March 13, 2008
    Date of Patent: May 24, 2011
    Assignee: IFP Energies Nouvelles
    Inventors: Florent Picard, Quentin Debuisschert, Annick Pucci
  • Patent number: 7914669
    Abstract: A process to substantially reduce the sulfur content of a liquid hydrocarbon stream by contacting the hydrocarbon stream with an aqueous stream containing a mixture of one or more extraction agents selected from hypochlorites, cyanurates and alkali metal and alkaline earth metal hydroxides, optionally in the presence of a catalyst, to remove sulfur compounds.
    Type: Grant
    Filed: December 22, 2004
    Date of Patent: March 29, 2011
    Assignee: Saudi Arabian Oil Company
    Inventors: Gary Dean Martinie, Farhan M. Al-Shahrani
  • Patent number: 7892418
    Abstract: The present invention relates to a process for reducing sulfur content in petroleum fuel, such as diesel fuel, and raising the Cetane Number to a value above 50.
    Type: Grant
    Filed: May 26, 2009
    Date of Patent: February 22, 2011
    Assignee: Oil Tech SARL
    Inventor: Hassan Agha
  • Patent number: 7820031
    Abstract: The present disclosure is directed to a multi-stage system and a process utilizing said system with the design of reducing the sulfur-content in a liquid comprising hydrocarbons and organosulfur compounds. The process comprising at least one of the following states: (1) an oxidation stage; (2) an extraction state; (3) a raffinate washing stage; (4) a raffinate polishing stage; (5) a solvent recovery stage; (6) a solvent purification stage; and (7) a hydrocarbon recovery stage. The process for removing sulfur-containing hydrocarbons from gas oil, which comprises oxidizing gas oil comprising hydrocarbons and organosulfur compounds to obtain a product gas oil.
    Type: Grant
    Filed: October 20, 2004
    Date of Patent: October 26, 2010
    Assignee: Degussa Corporation
    Inventors: Robert N. D'Alessandro, John Tarabocchia, Jerald Andrew Jones, Steven E. Bonde, Stefan Leininger
  • Patent number: 7811538
    Abstract: The method allows to remove mercaptans contained in a gaseous feed comprising hydrocarbons by carrying out the following stages: a) contacting, in a reactor R1, gaseous feed 1 with a liquid stream 13 comprising olefins, in the presence of a first acid catalyst so that the mercaptans react with the olefins so as to form sulfides, b) discharging an effluent 3 from reactor R1 and separating the effluent into a gas phase and a liquid phase so as to obtain a mercaptan-depleted treated gas 4 and a sulfide-laden liquid, c) separating the sulfide-laden liquid into a first fraction 6 and a second fraction 5, the volume flow rate of first fraction 6 being at least three times higher than the volume flow rate of second fraction 5, d) recycling first fraction 6 to stage a) as a first portion of said liquid stream to be fed into said reactor R1, e) regenerating second fraction 5 by cracking so as to obtain a sulfide-depleted second fraction 2 that is recycled to stage a) as a second portion of said liquid stream.
    Type: Grant
    Filed: March 28, 2008
    Date of Patent: October 12, 2010
    Assignee: Institut Francais du Petrole
    Inventors: Renaud Cadours, Eric Lemaire, Julia Magne-Drisch
  • Patent number: 7803270
    Abstract: A process is described for the extractive oxidation of contaminants present in raw fuel streams rich in heteroatomic polar compounds and catalyzed by iron oxides contained in natural limonitic goethite, said process comprising contacting said streams with an oxidation pair which is a peroxide in solution/organic acid in amount of at least 3 and an amount between 0.01 and 10 wt % of an iron oxide, both based on the feed, the iron oxide being made up of a reduced natural limonitic goethite. The goethite reduction by a hydrogen stream has the advantage of lowering the migration of non-contaminating polar hydrocarbons from the fuel stream to the aqueous phase, at the same time obtaining higher mass yield of final product fuel while the level of target contaminants to be removed is maintained relative to the state-of-the-art process. Process yields attain 98% weight/weight.
    Type: Grant
    Filed: March 14, 2005
    Date of Patent: September 28, 2010
    Assignee: Petroleo Brasileiro S.A. - Petrobras
    Inventors: Wladmir Ferraz de Souza, Lilian Ernst
  • Patent number: 7758745
    Abstract: A diesel desulfurization method has various steps including: implementing a modified oxidative desulfurization (UAOD) process. The UAOD has the steps of: mixing diesel fuel with room temperature ionic liquid, oxidant, phase transfer catalyst, and acid catalyst in a tank in a mix; recycling the ionic liquid and recycling the acid catalyst in aqueous phase. A step is to move the sulfur from the diesel fuel in a fluidized bed reactor (FBR) having bed reactor material. The process can be improved with ultrasound during mixing, or a high shear mixer. The bed reactor is preferably acidic alumina for adsorbing oxidized sulfur. The oxidant is preferably hydrogen peroxide (H2O2). The acid catalyst is preferably a mixture of Acetic acid and Tri-fluoro acetic acid.
    Type: Grant
    Filed: March 20, 2008
    Date of Patent: July 20, 2010
    Inventor: Shun-Sheng Cheng
  • Publication number: 20100176031
    Abstract: Crystals of [VOBDC](H2BDC)0.71 were synthesized hydrothemally. The guest acid molecules were removed by heating in air to give high quality single crystals of VOBDC. VOBDC was observed to show crystal-to-crystal transformations on absorption of the guest molecules aniline, thiophene and acetone from the liquid phase. Accurate structural data of the guest molecules and framework deformations were obtained from single crystal X-ray data. VOBDC was also shown to absorb selectively thiophene and dimethyl sulphide from methane.
    Type: Application
    Filed: August 9, 2007
    Publication date: July 15, 2010
    Inventors: Allan J. Jacobson, Xiqu Wang, Lumei Liu
  • Publication number: 20100155303
    Abstract: Disclosed is a method for desulfurization of a hydrocarbon oil (e.g., kerosene which is a raw fuel for a fuel cell) which can effectively remove benzothiophenes and dibenzothiophenes contained in the hydrocarbon oil under mild conditions to produce a desulfurized hydrocarbon oil having a significantly low sulfur content. The method comprises the step of desulfurizing the hydrocarbon oil such as kerosene containing benzothiophenes and dibenzothiophenes with the combination of a solid acid-type desulfurizing agent and an active carbon-type desulfurizing agent. This method can provide a hydrocarbon oil having a significantly low sulfur content. By using the hydrocarbon oil, the operation or maintenance of a fuel cell system can be made easily, a fuel cell itself can be miniaturized in size, and the lifetime of a desulfurizing agent in a desulfurization apparatus equipped in a fuel cell system can be prolonged.
    Type: Application
    Filed: July 25, 2006
    Publication date: June 24, 2010
    Applicant: JAPAN ENERGY CORPORATION
    Inventors: Yasuhiro Toida, Toru Saito
  • Publication number: 20100147748
    Abstract: A process for adsorbing aromatic sulfur compounds, where an adsorbent is contacted with a C6-C20 aromatic and/or aliphatic stream which comprises a solution of (i) at least one benzothiophene compound, (ii) a solvent which comprises at least one C6-C16 aliphatic compound, and (iii) optionally at least one C6-C12 aromatic compound. In this process, the adsorbent is regenerated using an organic regenerant such as, but not limited to, toluene. Also disclosed is another process for adsorbing aromatic sulfur compounds. In this process, an adsorbent is contacted with a mixture comprising a model diesel feed comprising at least one benzothiophene compound. In this process, the adsorbent is regenerated using an organic regenerant such as, but not limited to, toluene.
    Type: Application
    Filed: December 16, 2008
    Publication date: June 17, 2010
    Inventors: Xiaolin Wei, Scott M. Husson, Marcus V. Dutra e Mello, Daniel Chinn, Zunqing He
  • Publication number: 20100140142
    Abstract: A crude oil which contains at least 0.1 wt % unstable sulfur compounds is treated in a reaction zone at low temperature to convert at least 50 wt % of the unstable sulfur compounds contained therein. The reaction and removal of sulfur from the crude may be facilitated by contacting the crude oil with a catalytic material in the presence of a stripping fluid.
    Type: Application
    Filed: December 10, 2008
    Publication date: June 10, 2010
    Inventors: Huping Luo, Zhen Zhon, Lin Li, Alice He, Daniel Chinn, Graham Forder, Lyman Young, Shabbir Husain, William Schinski
  • Publication number: 20100122937
    Abstract: A method is provided for purifying a hydrocarbon oil comprising a quantity of impurities. A Lewis acid solution comprising a Lewis acid and an aprotic solvent is added to the hydrocarbon oil having the plurality of impurities, e.g. sulfur, vanadium, and nickel impurities, to form a mixture. Complexes are formed between the Lewis acid of the Lewis acid solution and a respective one of the impurities in the mixture. The mixture is separated into a first layer that comprises a purified fraction of the hydrocarbon oil and a second layer comprising the complexes dissolved in the aprotic solvent.
    Type: Application
    Filed: November 20, 2008
    Publication date: May 20, 2010
    Inventors: John Aibangbee Osaheni, Thomas Joseph Fyvie
  • Patent number: 7666297
    Abstract: An improved oxidative process that employ a robust, non-aqueous, and oil-soluble organic peroxide oxidant for effective desulfurization and denitrogenation of hydrocarbons including petroleum fuels, hydrotreated vacuum gas oil (VGO), non-hydrotreated VGO, petroleum crude oil, synthetic crude oil from oil sand, and residual oil. Even at low concentrations and without the assistance of catalysts, the non-aqueous organic peroxide oxidant is extremely active and fast in oxidizing the sulfur and nitrogen compounds in the hydrocarbon feedstocks. Furthermore, the process generates a valuable organic acid by-product that is also used internally as the extractive solvent for effective removal of the oxidized sulfur and nitrogen from the hydrocarbons without the need of a final adsorption step. Novel process steps are also disclosed to substantially prevent yield loss in the oxidative process.
    Type: Grant
    Filed: December 21, 2006
    Date of Patent: February 23, 2010
    Assignee: CPC Corporation, Taiwan
    Inventors: Fu-Ming Lee, Tzong-Bin Lin, Hsun-Yi Huang, Jyh-Haur Hwang, Hung-Chung Shen, Karl Tze-Tang Chuang
  • Publication number: 20090314688
    Abstract: A method for degumming and/or refining crude oil containing impurities involving mixing the crude oil with degumming agents, i.e., water or acid, and subjecting the mixture to flow-through, hydrodynamic cavitation processing. The cavitational processing transfers impurities in the crude oil to a water phase for easier separation. The water phase may be separated from the oil phase by commonly available separation methods.
    Type: Application
    Filed: June 15, 2009
    Publication date: December 24, 2009
    Inventors: Roman Gordon, Igor Gorodnitsky, Varvara Grichko
  • Publication number: 20090288982
    Abstract: The present invention relates to a process for reducing sulfur content in petroleum fuel, such as diesel fuel, and raising the Cetane Number to a value above 50.
    Type: Application
    Filed: May 26, 2009
    Publication date: November 26, 2009
    Inventor: Hassan Agha
  • Patent number: 7608182
    Abstract: A process for reducing the level of elemental sulfur and organic sulfur pick-up by refined hydrocarbon streams such as gasoline, diesel, jet fuel, kerosene or fuel additives such as ethers or iso-octane that are transported through a pipeline used to transport various sulfur-containing petroleum streams. The oxygen level in the hydrocarbon stream of interest to be pipelined as well as in at least the first hydrocarbon stream sequenced immediately ahead of the hydrocarbon stream of interest is reduced.
    Type: Grant
    Filed: November 15, 2005
    Date of Patent: October 27, 2009
    Assignee: ExxonMobil Research and Engineering Company
    Inventor: Joseph L. Feimer
  • Publication number: 20090255849
    Abstract: Mercaptans and/or hydrogen sulfide (H2S) in hydrocarbons, naphthas, gasolines, and the like may be scavenged therefrom by being brought into intimate contact with a mercaptan scavenger formulation containing at least one disubstituted azodicarboxylate of the formula R1OOCN?NCOOR2, where R1 and R2 are independently alkyl groups, alkenyl groups and aromatic groups having from 1 to 18 carbon atoms. These scavengers remove mercaptans and/or H2S from hydrocarbons faster than many conventional mercaptan scavengers. An effective scavenging amount of disubstituted azodicarboxylate in the hydrocarbon fluid ranges from about 5 to about 20 parts by weight based on 1 part as sulfur of mercaptan and/or H2S.
    Type: Application
    Filed: April 8, 2009
    Publication date: October 15, 2009
    Applicant: BAKER HUGHES INCORPORATED
    Inventors: Jianzhong Yang, Joseph J. Arensdorf, Melanie V. Baker
  • Publication number: 20090230027
    Abstract: Improved desulfurization compositions are provided for removing substantial fractions of sulfur, sulfur complexes, and sulfur compounds from liquid hydrocarbons such as crude oil and fuels. The preferred compositions comprise respective quantities of an alkylphenol ethoxylate, an amine, and an alkali metal nitrite. The compositions may be contacted with liquid hydrocarbons to achieve high levels of desulfurization.
    Type: Application
    Filed: May 20, 2009
    Publication date: September 17, 2009
    Applicant: JACAM CHEMICALS, LLC
    Inventors: Gene H. Zaid, Beth Ann Wolf, Gary W. Zorn
  • Publication number: 20090008295
    Abstract: Processes and systems associated with hydrodynamic cavitation-catalyzed oxidation of sulfur-containing substances in a fluid are described. In one example method, carbonaceous fluid is combined with at least one oxidant to form a mixture and then the mixture is flowed through at least one local constriction in a flow-through chamber at a sufficient pressure and flow rate to create hydrodynamic cavitation in the flowing mixture having a power density of between about 3,600 kWatts/cm2 and about 56,000 kWatts/cm2 measured at the surface of the local constriction normal to the direction of fluid flow. The creation of hydrodynamic cavitation in the flowing mixture initiates one or more chemical reactions that, at least in part, oxidize at least some of the sulfur-containing substances in the carbonaceous fluid.
    Type: Application
    Filed: June 9, 2008
    Publication date: January 8, 2009
    Applicant: Arisdyne Systems, Inc.
    Inventor: Oleg V. Kozyuk
  • Publication number: 20090000990
    Abstract: A method of desulfurizing/refining a hydrocarbon oil by which sulfur compounds are diminished to an extremely low concentration at a relatively low equipment cost and operating cost. The method of desulfurizing/refining a hydrocarbon oil comprises bringing a hydrocarbon oil containing at least one sulfur compound selected from the group consisting of thiophene compounds, benzothiophene compounds, and dibenzothiophene compounds and optionally further containing aromatic hydrocarbons into contact with a solid acid catalyst and/or an activated carbon having a transition metal oxide supported thereon to thereby desulfurize the oil. The solid acid catalyst preferably is a solid ultrastrong-acid catalyst selected among sulfuric acid radical/zirconia, sulfuric acid radical/alumina, sulfuric acid radical/tin oxide, sulfuric acid radical/iron oxide, tungstic acid/zirconia, and tungstic acid/tin oxide.
    Type: Application
    Filed: January 27, 2005
    Publication date: January 1, 2009
    Applicant: JAPAN ENERGY CORPORATION
    Inventor: Yasuhiro Toida
  • Publication number: 20080149533
    Abstract: The present invention relates to a process of reducing sulfur- or nitrogen-containing compounds and producing oxygenates, and in particular to a one-pot process of reducing sulfur- or nitrogen-containing compounds and also producing oxygenates in the presence of a homogeneous catalyst such as Mn+/a first solvent or M1n+/a second solvent/M2m+/a third solvent or a mixture thereof, the process herein being useful as an excellent octane booster in the reformulated gasoline and as a cetane booster for the future oxygenated diesel in a one-pot reaction.
    Type: Application
    Filed: October 11, 2007
    Publication date: June 26, 2008
    Applicant: KOCAT INC.
    Inventors: Jin S. YOO, Sang-Chul LEE, Ho Dong KIM
  • Patent number: 7276152
    Abstract: A robust, non-aqueous, and oil-soluble organic peroxide oxidant is employed for oxidative desulfurization and denitrogenation of hydrocarbon feedstocks including petroleum fuels. Even at low concentrations, the non-aqueous organic peroxide oxidant is extremely active and fast in oxidizing the sulfur and nitrogen compounds in the hydrocarbon feedstocks without catalyst. Consequently, the oxidation reactions that employ the non-aqueous organic peroxide oxidant take place at substantially lower temperatures and shorter residence times than reactions in other oxidative desulfurization and denitrogenation processes. As a result, a higher percentage of the valuable non-sulfur and non-nitrogen containing components in the hydrocarbon feedstock are more likely preserved with the inventive process. Desulfurization and denitrogenation occur in a single phase non-aqueous environment so that no phase transfer of the oxidant is required.
    Type: Grant
    Filed: November 23, 2004
    Date of Patent: October 2, 2007
    Assignee: CPC Corporation, Taiwan
    Inventors: Tzong-Bin Lin, Hsun-Yi Huang, Jyh-Haur Hwang, Hung-Chung Shen, Karl Tze-Tang Chuang
  • Patent number: 7252756
    Abstract: A process is disclosed for the production of refinery transportation fuel or components for refinery blending of transportation fuels having a reduced amount of sulfur and/or nitrogen-containing impurities. The process involves contacting a hydrocarbon feedstock containing the above impurities with an immiscible phase containing hydrogen peroxide and acetic acid in an oxidation zone to selectively oxidize the impurities. After a gravity phase separation, the hydrocarbon phase containing any remaining oxidized impurities, is passed to an extraction zone wherein aqueous acetic acid is used to extract a portion of any remaining oxidized impurities. A hydrocarbon stream having reduced impurities can then be recovered. The acetic acid phase effluents from the oxidation and the extraction zones can then be passed to a common separation zone for recovery of the acetic acid and for optional recycle back to the oxidation and extraction zones.
    Type: Grant
    Filed: December 18, 2002
    Date of Patent: August 7, 2007
    Assignee: BP Corporation North America Inc.
    Inventors: William H. Gong, Larry W. Kruse, George A. Huff, Michael Muskett
  • Patent number: 7192565
    Abstract: The gaseous feed flowing in through line 1 is contacted in contacting zone ZA with a liquid solvent flowing in through line 2. The solvent comprises between 0.001% and 100% by weight of a liquid olefin. Contacting in zone ZA is carried out in the presence of an acid catalyst. The purified gaseous feed is discharged from zone ZA through line 3. The sulfide-laden solvent is discharged through line 4, then regenerated in unit RE. The regenerated solvent is recycled through lines 7 and 2 to zone ZA.
    Type: Grant
    Filed: August 2, 2005
    Date of Patent: March 20, 2007
    Assignee: Institut Francais du Petrole
    Inventors: Patrick Briot, Renaud Cadours, Sophie Drozdz, Fabrice Lecomte
  • Patent number: 7179368
    Abstract: The invention concerns a method for selectively desulphurizing thiopene compounds contained in hydrocarbons derived from crude oil distillation, whether refined or not, which consists in oxidising the thiophene sulphur atoms into sulphone in the presence of an oxidising agent and in separating said sulphonated compounds from said hydrocarbons. The invention is characterised in that it consists in oxidising the thiophene compounds in a two-phase turbulent medium comprising a hydrocarbon phase and an aqueous phase, in the presence of at least an oxidising agent soluble in at least one of the two phases and of at least a metal catalyst in soluble or dispersed form in a liquid of in solid form, separation and oxidation occurring simultaneously.
    Type: Grant
    Filed: December 28, 2000
    Date of Patent: February 20, 2007
    Assignee: ELF Antar France
    Inventors: Alain Rabion, Francois Fajula, Jean René Bernard, Vasile Hulea
  • Patent number: 7175755
    Abstract: A process for the extractive oxidation of contaminants from raw hydrocarbon streams rich in heteroatomic polar compounds is described, the said process involving the extractive oxidation of sulfur and nitrogen compounds from said streams, the said process comprising treating said streams with a peroxide solution/organic acid couple, the weight percent of the peroxide solution and organic acid based on raw hydrocarbon being at least 3 for both the peroxide and organic acid solution, under an acidic pH, atmospheric or higher pressure and ambient or higher temperature. As a result of the reaction, the oxidized heteroatomic compounds, having strong affinity for the aqueous phase, are extracted into said aqueous phase, while the oxidized hydrocarbon is neutralized, water washed and dried, the resulting end product being a hydrocarbon stream from which have been removed 88.1 wt % or more of total nitrogen compounds and basic nitrogen up to 99.1 wt %, both calculated as mass contents, total Sulfur 23.
    Type: Grant
    Filed: May 6, 2003
    Date of Patent: February 13, 2007
    Assignee: Petroleo Brasileiro S.A.-Petrobras
    Inventor: Wladmir Ferraz de Souza
  • Patent number: 7153414
    Abstract: A process for the upgrading of raw hydrocarbon streams rich in heteroatomic polar compounds and/or unsaturated moieties involving the extractive oxidation of sulfur, nitrogen, conjugated dienes and other unsaturated compounds from said streams, the said process comprising treating said streams with a peroxide solution/organic acid couple and an iron oxide catalyst which is a limonite ore, under an acidic pH, atmospheric pressure and ambient or higher temperature. As a result of the reaction, the oxidized heteroatomic compounds, having strong affinity for the aqueous slurry phase, are extracted into said aqueous phase, while the oxidized hydrocarbon is separated from catalyst by decanting, neutralizing, water washing and drying, the resulting end product being a hydrocarbon stream from which have been removed 90% or more of total nitrogen compounds and basic nitrogen up to 99.7%, both calculated as mass contents.
    Type: Grant
    Filed: December 10, 2002
    Date of Patent: December 26, 2006
    Assignee: Petroleo Brasileiro S.A.-Petrobras
    Inventor: Wladmir Ferraz De Souza
  • Patent number: 7019188
    Abstract: The present invention relates to the separation of olefins, diolefins and lower aromatics from mixed streams of hydrocarbons using ionic liquids in the absence of metal compounds. The present invention eliminates the metal complexes conventionally used in such separation and thus reduces the complexity of the process.
    Type: Grant
    Filed: June 14, 2002
    Date of Patent: March 28, 2006
    Assignee: Nova Chemicals (International) S.A.
    Inventors: Ronald Scott Smith, Patricio S Herrera, Sean Reynolds
  • Patent number: 6875341
    Abstract: A process for upgrading hydrocarbonaceous oil containing heteroatom-containing compounds where the hydrocarbonaceous oil is contacted with a solvent system that is a mixture of a major portion of a polar solvent having a dipole moment greater than about 1 debye and a minor portion of water to selectively separate the constituents of the carbonaceous oil into a heteroatom-depleted raffinate fraction and heteroatom-enriched extract fraction. The polar solvent and the water-in-solvent system are formulated at a ratio where the water is an antisolvent in an amount to inhibit solubility of heteroatom-containing compounds and the polar solvent in the raffinate, and to inhibit solubility of non-heteroatom-containing compounds in the extract. The ratio of the hydrocarbonaceous oil to the solvent system is such that a coefficient of separation is at least 50%.
    Type: Grant
    Filed: May 23, 2000
    Date of Patent: April 5, 2005
    Assignee: James W. Bunger and Associates, Inc.
    Inventors: James W. Bunger, Donald E. Cogswell
  • Patent number: 6849774
    Abstract: Methods for separating di-olefins from mono-olefins, and olefins from non-olefins such as paraffins, oxygenates and aromatics; are provided. The methods use metal salts which complex both mono-olefins and di-olefins, but which selectively complex di-olefins in the presence of mono-olefins. The metal salts are dissolved or suspended in ionic liquids, which tend to have virtually no vapor pressure. Preferred salts are Group IB salts, more preferably silver and copper salts. A preferred silver salt is silver tetrafluoroborate. A preferred copper salt is silver CuOTf. Preferred ionic liquids are those which form stable solutions, suspensions or dispersions of the metal salts, which do not dissolve unwanted non-olefins, and which do not isomerize the mono- or di-olefins. The equivalents of the metal salt can be adjusted so that di-olefins are selectively adsorbed from mixtures of mono- and di-olefins. Alternatively, both mono- and di-olefins can be adsorbed, and the mono-olefins selectively desorbed.
    Type: Grant
    Filed: December 31, 2001
    Date of Patent: February 1, 2005
    Assignee: Chevron U.S.A. Inc.
    Inventors: Laura C. Boudreau, Michael S. Driver, Curt L. Munson, William L. Schinski
  • Patent number: 6827845
    Abstract: Economical processes are disclosed for the production of components for refinery blending of transportation fuels by selective oxidation of feedstocks comprising a mixture of hydrocarbons, sulfur-containing and nitrogen-containing organic compounds. Oxidation feedstock is contacted with an immiscible phase comprising at least one organic peracid or precursors of organic peracid in a liquid phase reaction mixture maintained substantially free of catalytic active metals and/or active metal-containing compounds and under conditions suitable for oxidation of one or more of the sulfur-containing and/or nitrogen-containing organic compounds. Blending components containing less sulfur and/or less nitrogen than the oxidation feedstock are recovered from the reaction mixture. Advantageously, at least a portion of the immiscible acid-containing phase is recycled to the oxidation.
    Type: Grant
    Filed: February 8, 2001
    Date of Patent: December 7, 2004
    Assignee: BP Corporation North America Inc.
    Inventors: William H. Gong, Monica Cristina Regalbuto, George A. Huff, Jr.
  • Publication number: 20040154959
    Abstract: Process for the desulphurization of a mixture of hydrocarbons containing sulphur compounds, comprising a step of oxidation by means of hydrogen peroxide, acetic acid and an acid catalyst in order to oxidize the sulphur compounds, in which the acid catalyst contains an acid solid chosen from cation-exchange resins having a pKa of less than or equal to 4, from solids based on silicon oxide additionally containing a trivalent metal, and from particles of inorganic solid on which acidic organic groups are grafted such that the particles thus grafted have a pKa of less than or equal to 4.
    Type: Application
    Filed: April 9, 2004
    Publication date: August 12, 2004
    Inventors: Jean-Paul Schoebrechts, Chantal Louis
  • Publication number: 20040118750
    Abstract: A process is disclosed for the production of refinery transportation fuel or components for refinery blending of transportation fuels having a reduced amount of sulfur and/or nitrogen-containing impurities. The process involves contacting a hydrocarbon feedstock containing the above impurities with an immiscible phase containing hydrogen peroxide and acetic acid in an oxidation zone to selectively oxidize the impurities. After a gravity phase separation, the hydrocarbon phase containing any remaining oxidized impurities, is passed to an extraction zone wherein aqueous acetic acid is used to extract a portion of any remaining oxidized impurities. A hydrocarbon stream having reduced impurities can then be recovered. The acetic acid phase effluents from the oxidation and the extraction zones can then be passed to a common separation zone for recovery of the acetic acid and for optional recycle back to the oxidation and extraction zones.
    Type: Application
    Filed: December 18, 2002
    Publication date: June 24, 2004
    Inventors: William H. Gong, Larry W. Kruse, George A. Huff, Michael Muskett
  • Publication number: 20040108252
    Abstract: A process for the upgrading of raw hydrocarbon streams rich in heteroatomic polar compounds and/or unsaturated moieties involving the extractive oxidation of sulfur, nitrogen, conjugated dienes and other unsaturated compounds from said streams, the said process comprising treating said streams with a peroxide solution/organic acid couple and an iron oxide catalyst which is a limonite ore, under an acidic pH, atmospheric pressure and ambient or higher temperature. As a result of the reaction, the oxidized heteroatomic compounds, having strong affinity for the aqueous slurry phase, are extracted into said aqueous phase, while the oxidized hydrocarbon is separated from catalyst by decanting, neutralizing, water washing and drying, the resulting end product being a hydrocarbon stream from which have been removed 90% or more of total nitrogen compounds and basic nitrogen up to 99.7%, both calculated as mass contents.
    Type: Application
    Filed: December 10, 2002
    Publication date: June 10, 2004
    Applicant: PETROLEO BRASILEIRO S.A. - PETROBRAS
    Inventor: Wladmir Ferraz De Souza
  • 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, Raphaël Le Gall
  • Patent number: 6596914
    Abstract: A multi-step process for desulfurizing liquid petroleum fuels that also removes nitrogen-containing compounds and aromatics. The process steps are: thiophene extraction; thiophene oxidation; thiophene-oxide and -dioxide extraction; raffinate solvent recovery and polishing; extract solvent recovery; and recycle-solvent purification. The thiophene oxidation is accomplished with hydrogen peroxide and the extraction solvent is acetic acid in combination with secondary solvents. The operating conditions in the process are relatively mild at near ambient pressure and less than 145° C. throughout the process, and the only chemical consumed in the process is hydrogen peroxide. The process design can be modified to accommodate a variety of liquid hydrocarbon feeds.
    Type: Grant
    Filed: August 25, 2001
    Date of Patent: July 22, 2003
    Inventors: Walter Gore, Steve Bonde, Geoffrey E. Dolbear, Ebbe R. Skov