With Acids Patents (Class 208/219)
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Patent number: 12042748Abstract: A liquid hydrocarbon desulfurization system having at least one processing unit, and preferably an initial and an end processing unit. Each processing unit having a reactor assembly and a sorption system. An aqueous system directs aqueous into the reactor assembly together with liquid hydrocarbon, wherein the two are mixed using shear mixers. An adsorbent system provides adsorbent to the sorption column to adsorb the oxidized sulfur resulting through the mixing of the liquid hydrocarbon with the aqueous. A system having multiple processing units is disclosed, as well as systems for transferring adsorbent and providing aqueous. A plurality of methods is likewise disclosed.Type: GrantFiled: January 18, 2022Date of Patent: July 23, 2024Assignee: ALTERNATIVE ENVIRONMENTAL TECHNOLOGIES SULFEX CORP.Inventors: Jack Lawrence Waldron, Kylen J. Smith
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Patent number: 10947461Abstract: 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: GrantFiled: March 27, 2019Date of Patent: March 16, 2021Assignee: Saudi Arabian Oil CompanyInventors: Emad Naji Al-Shafei, Esam Zaki Hamad
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Patent number: 9127214Abstract: 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: GrantFiled: February 5, 2013Date of Patent: September 8, 2015Inventors: Shun-Sheng Cheng, Teh-Jung Lin
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Publication number: 20150060334Abstract: 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: ApplicationFiled: August 30, 2013Publication date: March 5, 2015Applicant: UOP LLCInventor: Steven F. Zink
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Patent number: 8894843Abstract: 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: GrantFiled: June 11, 2012Date of Patent: November 25, 2014Assignee: Auterra, Inc.Inventors: Jonathan P. Rankin, Jennifer L. Vreeland, Kyle E. Litz, Tracey M. Jordan, Mark N. Rossetti, Eric H. Burnett, Trent A. McCaskill
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Patent number: 8778172Abstract: 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: GrantFiled: May 3, 2010Date of Patent: July 15, 2014Assignee: Dorf Ketal Chemicals (I) Private LimitedInventor: Mahesh Subramaniyam
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Publication number: 20130075305Abstract: 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: ApplicationFiled: September 26, 2012Publication date: March 28, 2013Applicant: SAUDI ARABIAN OIL COMPANYInventor: Saudi Arabian Oil Company
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Patent number: 8298404Abstract: 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: GrantFiled: September 22, 2010Date of Patent: October 30, 2012Assignee: Auterra, Inc.Inventors: Kyle E. Litz, Jennifer L. Vreeland, Jonathan P. Rankin, Thomas W. DeLancey, Timothy A. Thompson
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Patent number: 8287721Abstract: 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: GrantFiled: August 30, 2010Date of Patent: October 16, 2012Inventors: Lucinda Paris-Marcano, Maria Borjas-Garcia
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Patent number: 8246813Abstract: 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: GrantFiled: December 15, 2009Date of Patent: August 21, 2012Assignee: Nalco CompanyInventors: Dennis R. Compton, Samuel Jefferies, Ron Sharpe
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Patent number: 8241490Abstract: 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: GrantFiled: October 14, 2010Date of Patent: August 14, 2012Assignee: Auterra, Inc.Inventors: Kyle E. Litz, Jennifer L. Vreeland, Jonathan P. Rankin, Mark N. Rossetti, Tracey M. Jordan
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Patent number: 8197671Abstract: 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: GrantFiled: December 23, 2010Date of Patent: June 12, 2012Assignee: Auterra, Inc.Inventors: Jonathan P. Rankin, Jennifer L. Vreeland, Kyle E. Litz, Tracey M. Jordan, Mark N. Rossetti, Eric H. Burnett
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Publication number: 20120055848Abstract: 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: ApplicationFiled: May 3, 2010Publication date: March 8, 2012Applicant: DORF KETAL CHEMICALS (I) PRIVATE LIMITEDInventor: Mahesh Subramaniyam
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Patent number: 8048175Abstract: 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: GrantFiled: April 8, 2009Date of Patent: November 1, 2011Assignee: Baker Hughes IncorporatedInventors: Jianzhong Yang, Joseph J. Arensdorf, Melanie V. Barker
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Patent number: 8021540Abstract: 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: GrantFiled: January 27, 2005Date of Patent: September 20, 2011Assignee: Japan Energy CorporationInventor: Yasuhiro Toida
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Patent number: 8002971Abstract: 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: GrantFiled: June 9, 2008Date of Patent: August 23, 2011Assignee: Arisdyne Systems, Inc.Inventor: Oleg V. Kozyuk
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Patent number: 7947166Abstract: 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: GrantFiled: March 13, 2008Date of Patent: May 24, 2011Assignee: IFP Energies NouvellesInventors: Florent Picard, Quentin Debuisschert, Annick Pucci
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Patent number: 7914669Abstract: 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: GrantFiled: December 22, 2004Date of Patent: March 29, 2011Assignee: Saudi Arabian Oil CompanyInventors: Gary Dean Martinie, Farhan M. Al-Shahrani
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Patent number: 7892418Abstract: 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: GrantFiled: May 26, 2009Date of Patent: February 22, 2011Assignee: Oil Tech SARLInventor: Hassan Agha
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Patent number: 7820031Abstract: 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: GrantFiled: October 20, 2004Date of Patent: October 26, 2010Assignee: Degussa CorporationInventors: Robert N. D'Alessandro, John Tarabocchia, Jerald Andrew Jones, Steven E. Bonde, Stefan Leininger
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Patent number: 7811538Abstract: 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: GrantFiled: March 28, 2008Date of Patent: October 12, 2010Assignee: Institut Francais du PetroleInventors: Renaud Cadours, Eric Lemaire, Julia Magne-Drisch
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Patent number: 7803270Abstract: 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: GrantFiled: March 14, 2005Date of Patent: September 28, 2010Assignee: Petroleo Brasileiro S.A. - PetrobrasInventors: Wladmir Ferraz de Souza, Lilian Ernst
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Patent number: 7758745Abstract: 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: GrantFiled: March 20, 2008Date of Patent: July 20, 2010Inventor: Shun-Sheng Cheng
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Publication number: 20100176031Abstract: 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: ApplicationFiled: August 9, 2007Publication date: July 15, 2010Inventors: Allan J. Jacobson, Xiqu Wang, Lumei Liu
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Publication number: 20100155303Abstract: 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: ApplicationFiled: July 25, 2006Publication date: June 24, 2010Applicant: JAPAN ENERGY CORPORATIONInventors: Yasuhiro Toida, Toru Saito
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Publication number: 20100147748Abstract: 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: ApplicationFiled: December 16, 2008Publication date: June 17, 2010Inventors: Xiaolin Wei, Scott M. Husson, Marcus V. Dutra e Mello, Daniel Chinn, Zunqing He
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Publication number: 20100140142Abstract: 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: ApplicationFiled: December 10, 2008Publication date: June 10, 2010Inventors: Huping Luo, Zhen Zhon, Lin Li, Alice He, Daniel Chinn, Graham Forder, Lyman Young, Shabbir Husain, William Schinski
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Publication number: 20100122937Abstract: 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: ApplicationFiled: November 20, 2008Publication date: May 20, 2010Inventors: John Aibangbee Osaheni, Thomas Joseph Fyvie
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Patent number: 7666297Abstract: 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: GrantFiled: December 21, 2006Date of Patent: February 23, 2010Assignee: CPC Corporation, TaiwanInventors: Fu-Ming Lee, Tzong-Bin Lin, Hsun-Yi Huang, Jyh-Haur Hwang, Hung-Chung Shen, Karl Tze-Tang Chuang
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Publication number: 20090314688Abstract: 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: ApplicationFiled: June 15, 2009Publication date: December 24, 2009Inventors: Roman Gordon, Igor Gorodnitsky, Varvara Grichko
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Publication number: 20090288982Abstract: 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: ApplicationFiled: May 26, 2009Publication date: November 26, 2009Inventor: Hassan Agha
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Patent number: 7608182Abstract: 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: GrantFiled: November 15, 2005Date of Patent: October 27, 2009Assignee: ExxonMobil Research and Engineering CompanyInventor: Joseph L. Feimer
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Publication number: 20090255849Abstract: 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: ApplicationFiled: April 8, 2009Publication date: October 15, 2009Applicant: BAKER HUGHES INCORPORATEDInventors: Jianzhong Yang, Joseph J. Arensdorf, Melanie V. Baker
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Publication number: 20090230027Abstract: 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: ApplicationFiled: May 20, 2009Publication date: September 17, 2009Applicant: JACAM CHEMICALS, LLCInventors: Gene H. Zaid, Beth Ann Wolf, Gary W. Zorn
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Publication number: 20090008295Abstract: 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: ApplicationFiled: June 9, 2008Publication date: January 8, 2009Applicant: Arisdyne Systems, Inc.Inventor: Oleg V. Kozyuk
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Publication number: 20090000990Abstract: 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: ApplicationFiled: January 27, 2005Publication date: January 1, 2009Applicant: JAPAN ENERGY CORPORATIONInventor: Yasuhiro Toida
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Publication number: 20080149533Abstract: 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: ApplicationFiled: October 11, 2007Publication date: June 26, 2008Applicant: KOCAT INC.Inventors: Jin S. YOO, Sang-Chul LEE, Ho Dong KIM
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Patent number: 7276152Abstract: 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: GrantFiled: November 23, 2004Date of Patent: October 2, 2007Assignee: CPC Corporation, TaiwanInventors: Tzong-Bin Lin, Hsun-Yi Huang, Jyh-Haur Hwang, Hung-Chung Shen, Karl Tze-Tang Chuang
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Patent number: 7252756Abstract: 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: GrantFiled: December 18, 2002Date of Patent: August 7, 2007Assignee: BP Corporation North America Inc.Inventors: William H. Gong, Larry W. Kruse, George A. Huff, Michael Muskett
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Patent number: 7192565Abstract: 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: GrantFiled: August 2, 2005Date of Patent: March 20, 2007Assignee: Institut Francais du PetroleInventors: Patrick Briot, Renaud Cadours, Sophie Drozdz, Fabrice Lecomte
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Patent number: 7179368Abstract: 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: GrantFiled: December 28, 2000Date of Patent: February 20, 2007Assignee: ELF Antar FranceInventors: Alain Rabion, Francois Fajula, Jean René Bernard, Vasile Hulea
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Patent number: 7175755Abstract: 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: GrantFiled: May 6, 2003Date of Patent: February 13, 2007Assignee: Petroleo Brasileiro S.A.-PetrobrasInventor: Wladmir Ferraz de Souza
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Patent number: 7153414Abstract: 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: GrantFiled: December 10, 2002Date of Patent: December 26, 2006Assignee: Petroleo Brasileiro S.A.-PetrobrasInventor: Wladmir Ferraz De Souza
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Patent number: 7019188Abstract: 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: GrantFiled: June 14, 2002Date of Patent: March 28, 2006Assignee: Nova Chemicals (International) S.A.Inventors: Ronald Scott Smith, Patricio S Herrera, Sean Reynolds
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Patent number: 6875341Abstract: 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: GrantFiled: May 23, 2000Date of Patent: April 5, 2005Assignee: James W. Bunger and Associates, Inc.Inventors: James W. Bunger, Donald E. Cogswell
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Patent number: 6849774Abstract: 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: GrantFiled: December 31, 2001Date of Patent: February 1, 2005Assignee: Chevron U.S.A. Inc.Inventors: Laura C. Boudreau, Michael S. Driver, Curt L. Munson, William L. Schinski
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Patent number: 6827845Abstract: 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: GrantFiled: February 8, 2001Date of Patent: December 7, 2004Assignee: BP Corporation North America Inc.Inventors: William H. Gong, Monica Cristina Regalbuto, George A. Huff, Jr.
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Publication number: 20040154959Abstract: 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: ApplicationFiled: April 9, 2004Publication date: August 12, 2004Inventors: Jean-Paul Schoebrechts, Chantal Louis
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Publication number: 20040118750Abstract: 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: ApplicationFiled: December 18, 2002Publication date: June 24, 2004Inventors: William H. Gong, Larry W. Kruse, George A. Huff, Michael Muskett
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Publication number: 20040108252Abstract: 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: ApplicationFiled: December 10, 2002Publication date: June 10, 2004Applicant: PETROLEO BRASILEIRO S.A. - PETROBRASInventor: Wladmir Ferraz De Souza