With Nitrogen Containing Treating Reagent Patents (Class 208/236)
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Patent number: 11819777Abstract: Reclaimer systems and methods of their use are provided. Reclaimer systems use one or more fluid input streams and a variable steam input to control temperature of a fluid in a reclaimer vessel. In certain embodiments, a temperature controller and level controller are both connected to at least one fluid input stream subsystem and a steam input subsystem. Output from the level controller and the temperature controller is used to control flow through both a fluid input stream subsystem and a steam input subsystem. In certain embodiments, selectors are used to determine which controller output to obey when controlling the steam input subsystem and the fluid input stream subsystem. In certain embodiments, lean amine agent and an inert fluid are input in a ratio controlled by a ratio controller in order to maintain the fluid level in a vessel.Type: GrantFiled: August 22, 2017Date of Patent: November 21, 2023Assignee: SAUDI ARABIAN OIL COMPANYInventors: Diki Andrian, Amjad A. Alshaer
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Patent number: 11236262Abstract: A method and system remove hydrogen sulfide from a sour liquid. In an embodiment, the method for removing hydrogen sulfide from a hydrocarbon containing fluid includes contacting a methylmorpholine-N-oxide solution with the sour liquid. The method also includes allowing the methylmorpholine-N-oxide to react with the hydrogen sulfide to remove the hydrogen sulfide.Type: GrantFiled: December 10, 2019Date of Patent: February 1, 2022Assignee: United Laboratories International, LLCInventors: Stephen D. Matza, Martha T. Smith, Jack G. Frost
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Patent number: 10995280Abstract: A scavenger composition comprising a carrier and an active metal, wherein the carrier is present in an amount of about 1.0 wt % to about 99.0 wt. %, based on total weight of the composition, and the active metal is present in an amount of about 1.0 wt % to about 99.0 wt. %, based on total weight of the composition, wherein the active metal is a metal salt or metal chelate, and wherein the metal is chosen from iron, copper, molybdenum and zinc.Type: GrantFiled: February 14, 2020Date of Patent: May 4, 2021Assignee: Innophos, Inc.Inventors: Jean Valery Martin, Giovanni Onnembo, Evelyn Olanipekun, Kevin Kempton, Arbnor Ibraimi, William Carton
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Patent number: 10828627Abstract: The invention has as its object a catalyst that comprises a substrate based on alumina or silica or silica-alumina, at least one element from group VIII, at least one element from group VIB, and at least one additive that is selected from among 2-acetylbutyrolactone and/or its hydrolysis products, 2-(2-hydroxyethyl)-3-oxobutanoic acid, and 3-hydroxy-2-(2-hydroxyethyl)-2-butenoic acid. The invention also relates to the method for preparation of said catalyst and its use in a method for hydrotreatment and/or hydrocracking.Type: GrantFiled: June 22, 2017Date of Patent: November 10, 2020Assignee: IFP Energies NouvellesInventor: P-Louis Carrette
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Patent number: 10751639Abstract: A process and apparatus for hydrocracking a hydrocarbon stream and with heat integration between two stripping columns. Both stripping columns use a reboiler for heat input to avoid steam recovery and dew point issues in the overhead. A hot stripped stream can provide heat to the cold stripping column by heat exchange. Additionally, as few as two heaters that rely on external utilities may be required for reboiling fractionator column bottoms.Type: GrantFiled: June 26, 2018Date of Patent: August 25, 2020Assignee: UOP LLCInventors: Hari S. Bajpai, Donald A. Eizenga
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Patent number: 10669228Abstract: The disclosure provides compositions and methods that are useful in removing, lowering, or otherwise controlling hydrogen sulfide and mercaptans. The compositions and methods can be used in any industry where hydrogen sulfide poses problems, such as when dealing with crude oil based, natural gas based, and/or coal based products. In some embodiments, the compositions include one or more alkoxylated amino formaldehyde adducts.Type: GrantFiled: September 4, 2019Date of Patent: June 2, 2020Assignee: ECOLAB USA INC.Inventors: Prakasa Rao Anantaneni, Ryan Matthew Harrington, David Tarverdi, Lawrence J. Karas, Ravindranath Mukkamala, Subhasis De
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Patent number: 10526527Abstract: A method and system remove hydrogen sulfide from a sour liquid. In an embodiment, the method for removing hydrogen sulfide from a hydrocarbon containing fluid includes contacting a methylmorpholine-N-oxide solution with the sour liquid. The method also includes allowing the methylmorpholine-N-oxide to react with the hydrogen sulfide to remove the hydrogen sulfide.Type: GrantFiled: February 20, 2018Date of Patent: January 7, 2020Assignee: United Laboratories International, LLCInventors: Stephen D. Matza, Martha T. Smith, Jack G. Frost
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Patent number: 10308886Abstract: The present disclosure provides compositions and methods that are useful in removing, lowering the amount of, or otherwise controlling hydrogen sulfide and mercaptans. The compositions and methods can be used in any industry where hydrogen sulfide poses problems, such as when dealing with crude oil based, natural gas based, and/or coal based products. The present disclosure provides compositions and methods that can reduce the amount of or eliminate hydrogen sulfide in a variety of mediums.Type: GrantFiled: April 21, 2016Date of Patent: June 4, 2019Assignee: ECOLAB USA INC.Inventors: Geeta Rana, Julian M. Gallardo, Matthew Trevino
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Patent number: 10266463Abstract: Apparatuses, systems and methods for extracting isoprene using minimum capital investment, operating cost, and relatively corrosion free environment are disclosed herein. Embodiments of the invention are directed to producing pure isoprene and gasoline quality raffinate (free or sulfur and acetylenes) which are of value in manufacturing rubbers and other polymers.Type: GrantFiled: April 7, 2015Date of Patent: April 23, 2019Assignee: GTC Technology US LLCInventors: Venkata K. Ramanujam, Michael McCaulley, Joseph C. Gentry
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Patent number: 9920236Abstract: A method and system remove hydrogen sulfide from a sour liquid. In an embodiment, the method for removing hydrogen sulfide from a hydrocarbon containing fluid includes contacting a methylmorpholine-N-oxide solution with the sour liquid. The method also includes allowing the methylmorpholine-N-oxide to react with the hydrogen sulfide to remove the hydrogen sulfide.Type: GrantFiled: February 24, 2015Date of Patent: March 20, 2018Assignee: United Laboratories International, LLCInventors: Stephen D. Matza, Martha T. Smith, Jack G. Frost
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Patent number: 9512019Abstract: A method and system treat contaminated water. In one embodiment, the method comprises treating contaminated water by introducing a methylmorpholine-N-oxide solution to a vessel. The vessel contains the contaminated water and iron oxide. The contaminated water comprises contaminants. In addition, the methylmorpholine-N-oxide solution comprises methylmorpholine-N-oxide and water. The method further comprises contacting the methylmorpholine-N-oxide solution with the contaminated water. In addition, the method comprises treating the contaminated water by allowing the methylmorpholine-N-oxide to react with the contaminants in the presence of the iron oxide.Type: GrantFiled: October 12, 2012Date of Patent: December 6, 2016Assignee: United Laboratories International, LLCInventors: Stephen D. Matza, Jack G. Frost
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Patent number: 9463989Abstract: The use of a dialdehyde (e.g. glyoxal) and a nitrogen-containing scavenger (e.g. a triazine) when injected separately in media containing hydrogen sulfide (H2S) and/or mercaptans to scavenge H2S and/or mercaptans therefrom gives a synergistically better reaction rate and overall scavenging efficiency, i.e. capacity, over the use of the dialdehyde or the nitrogen-containing scavenger used alone, but in the same total amount of the dialdehyde and nitrogen-containing scavenger. The media may include an aqueous phase, a gas phase, a hydrocarbon phase and mixtures of a gas and/or hydrocarbon phase with an aqueous phase.Type: GrantFiled: June 20, 2012Date of Patent: October 11, 2016Assignee: BAKER HUGHES INCORPORATEDInventors: Carlos M. Menendez, Vladimir Jovancicevic, Sunder Ramachandran
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Patent number: 9440909Abstract: Methods for making sulfide scavenging compositions are provided. The method comprises reacting at least one secondary amine with at least one aldehyde and solvent in the presence of a catalyst to form a reaction composition, wherein a reaction temperature is less than or equal to 90° C. Sulfide scavengers using the above method are also disclosed. Methods for removing sulfides from fluid streams are also provided. The methods include adding the above sulfide scavengers to fluid streams.Type: GrantFiled: June 30, 2015Date of Patent: September 13, 2016Assignee: General Electric CompanyInventor: Gregory Kaplan
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Patent number: 9394188Abstract: One exemplary embodiment can be a process for oxidizing sulfides. The process can include passing an alkaline stream having about 1-about 30%, by weight, of an alkaline material and one or more sulfide compounds to a reaction zone having a metal phthalocyanine catalyst.Type: GrantFiled: January 18, 2013Date of Patent: July 19, 2016Assignee: UOP LLCInventors: Luigi Laricchia, Javier Rios
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Patent number: 9068127Abstract: A process for removing a nitrogen compound and a sulfur compound from a hydroprocessed vacuum gas oil feed includes contacting the hydroprocessed vacuum gas oil feed comprising the nitrogen compound and the sulfur compound with a VGO-immiscible phosphonium ionic liquid to produce a hydroprocessed vacuum gas oil and VGO-immiscible phosphonium ionic liquid mixture, and separating the mixture to produce a hydroprocessed vacuum gas oil effluent having a reduced nitrogen compound and sulfur compound content relative to the vacuum gas oil feed. It was found that the amount of the sulfur compound being removed was significantly improved by first removing the nitrogen compounds, especially polar nitrogen compounds.Type: GrantFiled: March 12, 2013Date of Patent: June 30, 2015Assignee: UOP LLCInventors: Beckay J. Mezza, Alakananda Bhattacharyya, Christopher P. Nicholas, Haiyan Wang
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Publication number: 20150136654Abstract: A process for treating a pitch fraction from coal tar is described. The pitch fraction is contacted with a solvent, an extraction agent, or an adsorbent to remove at least one contaminant, such as oxygenate compounds, nitrogen containing compounds, and sulfur containing compounds. The solvent can be an ionic liquid, the extraction agent can be at least one of amphiphilic block copolymers, cyclodextrins, functionalized cyclodextrins, and cyclodextrin-functionalized polymers, and the adsorbent can be exfoliated graphite oxide, thermally exfoliated graphite oxide or intercalated graphite compounds.Type: ApplicationFiled: August 28, 2014Publication date: May 21, 2015
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Publication number: 20150090639Abstract: Ionic liquids of the general formula C+A? where C+ represents an organic cation, specifically, but not limited to the imidazolium, pyridinium, isoquinolinium, ammonium types, which have aliphatic and aromatic substituents, while A? represents a carboxylate, aromatic and aliphatic anion. The ionic liquids are synthesized under conventional heating or microwave irradiation This invention is also related to the application of ionic liquids to remove sulfur compounds of naphthas through a liquid-liquid extraction and the recovery and reuse of ionic liquids by the application of heat, reduced pressure and washing with solvents.Type: ApplicationFiled: December 8, 2014Publication date: April 2, 2015Inventors: Rafael Martinez Palou, Natalya Victorovna Likhanova, Eugenio Alejandro Flores Oropeza, Diego Javier Guzman Lucero
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Publication number: 20140353213Abstract: A composition that comprises a support material having incorporated therein a metal component and impregnated with an additive compound that is selected from the group of heterocyclic, polar compounds of the formula CxHnNyOz; wherein: x is an integer of at least 3; y is either 0, 1, 2, or 3; z is either 0, 1, 2, or 3; and n is the number of hydrogen atoms required to fill the remaining bonds with the carbon atoms of the molecule. The composition includes the support material that is impregnated with the additive compound and is useful in the hydroprocessing of hydrocarbon feedstocks, especially in the denitrogenation and desulfurization of distillate feedstocks to make ultra low sulfur diesel.Type: ApplicationFiled: May 30, 2014Publication date: December 4, 2014Applicant: Shell Oil CompanyInventors: John Anthony SMEGAL, Alexei Grigorievich GABRIELOV, Ed GANJA, Theofiel MEURIS
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Patent number: 8888993Abstract: A method is disclosed for removing impurities such as nitrogen and/or sulfur compounds from a hydrocarbon feed, in which the feed is contacted with an adsorbent including a nitrogen-containing organic heterocyclic salt deposited on a porous support, e.g., a supported ionic liquid. Additionally, a method for hydrotreating a hydrocarbon feed which includes a hydroprocessing step is disclosed, wherein prior to hydroprocessing, the feed is contacted with an adsorbent including a supported ionic liquid. Additionally, a method for producing a lube oil which includes isomerization dewaxing of a base oil fraction is disclosed, wherein prior to the isomerization dewaxing step, the base oil fraction is contacted with an adsorbent including a supported ionic liquid. In one embodiment, the adsorbent is regenerated to restore its treatment capacity.Type: GrantFiled: July 12, 2011Date of Patent: November 18, 2014Assignee: Chevron U.S.A. Inc.Inventors: Akshay Verma, Bi Zeng Zhan, Zunqing He, Zhen Zhou, Marcus Dutra e Mellon, Sheila Yeh
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Patent number: 8888994Abstract: Method for deep desulphurization of hydrocarbon fuels includes following steps: (1) treatment of a hydrocarbon fuel under the condition of its mixing with gaseous oxidant selected from the group consisting nitrogen monoxide, dry air, ozone and a mixture of at least two of said reagents in order to oxidize sulfur-containing compounds presented in said fuel, and with a fine-dispersed adsorbent based on montmorillonite in order to adsorb oxidized sulfur-containing compounds, and (2) separation of spent adsorbent together with adsorbed oxidized sulfur-containing compounds from refined fuel.Type: GrantFiled: April 19, 2011Date of Patent: November 18, 2014Assignee: The United States of America as represented by the Administrator of the U.S. Environmental Protection AgencyInventors: Valerii Kukhar, Volodymir Kashkovski, Vladislav Kyselov, Yurii Besugly, Yurii Kyselov, Rajender Varma, Subhas Sikdar
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Publication number: 20140311948Abstract: Methods and apparatus relate to treatment of fluids to remove mercury contaminants in the fluid. Contact of the fluid with an amine that has absorbed a sulfur compound causes the mercury contaminants to be absorbed by the amine. Phase separation then removes from the fluid the amine loaded with the mercury contaminants such that a treated product remains.Type: ApplicationFiled: July 1, 2014Publication date: October 23, 2014Applicant: PHILLIPS 66 COMPANYInventors: John Michael Hays, Joe B. Cross
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Publication number: 20140305844Abstract: The ionic liquid for desulfurization of light fuels is 1-methyl-3-pentyl 1H-imidazolium periodate, having the structural formula: The compound is prepared by mixing 1-methyl-3-pentyl 1H-imidazolium tetrafluoroborate with sodium periodate in dichloromethane and water, stirring the mixture for 24 hours, and extracting the compound from the product with dichloromethane. The ionic liquid may be used for the desulfurization of light fuels by bringing the ionic liquid into contact with the crude light petroleum oil at a temperature of about 50° C. with stirring for a period of time sufficient to oxidize the sulfur containing impurities to water soluble sulfones, washing the mixture with water to remove the ionic liquids and water soluble sulfones, and drying the desulfurized light fuel product.Type: ApplicationFiled: April 10, 2013Publication date: October 16, 2014Applicants: KING ABDULAZIZ CITY FOR SCIENCE AND TECHNOLOGY, KING FADH UNIVERSITY OF PETROLEUM AND MINERALSInventors: KING FADH UNIVERSITY OF PETROLEUM AND MINERALS, KING ABDULAZIZ CITY FOR SCIENCE AND TECHNOLOGY
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Publication number: 20140299512Abstract: Processes are disclosed for reducing the sulphur content of a hydrocarbon material containing sulphur compounds.Type: ApplicationFiled: March 17, 2014Publication date: October 9, 2014Applicant: Ultraclean Fuel Pty Ltd.Inventors: Gordon John Gargano, Marc E. Halpern
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Publication number: 20140299513Abstract: The process for the desulfurization of a sulfur-containing hydrocarbon mixture, such as a full-range, hydrotreated diesel oil, is accomplished with an aqueous oxidizing agent in the presence of a catalyst and a co-catalyst, and thereafter selectively removing the oxidized compounds by solvent extraction. Optionally, the foregoing steps are followed by solvent stripping and recovery, and a final polishing step.Type: ApplicationFiled: April 8, 2014Publication date: October 9, 2014Applicant: Saudi Arabian Oil CompanyInventors: Gary D. MARTINIE, Farhan M. AL-SHAHRANI, Bashir O. DABBOUSI
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Patent number: 8845885Abstract: A method of removing sulfur from sour oil by subjecting sour oil having a first sulfur content to high shear in the presence of at least one desulfurizing agent to produce a high shear treated stream, wherein the at least one desulfurizing agent is selected from the group consisting of bases and inorganic salts, and separating both a sulfur-rich product and a sweetened oil product from the high shear-treated stream, wherein the sulfur-rich product comprises elemental sulfur and wherein the sweetened oil product has a second sulfur content that is less than the first sulfur content. A system for reducing the sulfur content of sour oil via at least one high shear device comprising at least one rotor and at least one complementarily-shaped stator, and at least one separation device configured to separate a sulfur-rich product and sweetened oil from the high shear-treated stream.Type: GrantFiled: August 2, 2011Date of Patent: September 30, 2014Assignee: H R D CorporationInventors: Abbas Hassan, Aziz Hassan, Rayford G. Anthony, Gregory G. Borsinger
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Patent number: 8821716Abstract: The present invention relates to an improved desulfurization process using an ionic liquid compound of general formula C+A?, where C+ represents an organic cation such as alkyl-pyridinium, di-alkyl imidazolium and tri-alkyl imidazolium; and A? is an anion of halides of iron (III), such as, for example, FeCl4?. The desulfurization process is also improved when producing the ionic liquid compound by heating the reactants using microwave energy. The ionic liquids can be used to desulfurize hydrocarbon mixtures by a liquid-liquid extraction.Type: GrantFiled: May 26, 2009Date of Patent: September 2, 2014Assignee: Instituto Mexicano del PetroleoInventors: Natalya Victorovna Likhanova, Rafael Martinez Palou, Jorge Froylan Palomeque Santiago
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Patent number: 8807214Abstract: Heavy crude oils having high sulfur content and viscosities are upgraded by a hydrodesulfurization (HDS) process that includes microwave irradiation of a mixture of the sour heavy crude oil with at least one catalyst and optionally, one or more sensitizers, and irradiation in the presence of hydrogen. The process is also adapted to microwave treatment of hard to break emulsions, either above ground or below ground where water-in-oil emulsions are initially formed, followed by the catalytic hydrodesulfurization promoted by application of further microwave energy to the demulsified crude oil stream.Type: GrantFiled: March 22, 2013Date of Patent: August 19, 2014Assignee: Saudi Arabian Oil CompanyInventors: M. Rashid Khan, Emad Naji Al-Shafei
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Publication number: 20140174987Abstract: The present invention relates to a process for handling product fluid streams which are obtained in the catalytic hydrogenation of liquid feeds in laboratory catalysis apparatuses. The liquid feeds are preferably hydrocarbons comprising sulfur- and nitrogen-comprising compounds as impurities. The hydrogenation serves to convert the impurities into hydrogen sulfide and ammonia which in this form can be readily separated off from the other constituents of the liquid feed. The product fluid streams are contacted with an inert gas stream, with the flow rate of the inert gas being a multiple of the flow rate of the product fluid stream. The formation of deposits in lines of the region on the outlet side of the reaction space can be effectively prevented by means of the process of the invention.Type: ApplicationFiled: July 30, 2012Publication date: June 26, 2014Applicant: hte Aktiengesellschaft the high throughput experimentation companyInventors: Josef Find, Alfred Haas, Armin Brenner
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Patent number: 8734639Abstract: Petroleum resid, bitumen and/or heavy oil is upgraded by the separation of asphaltenes and/or resins from such resids, bitumen and/or heavy oils by contacting them with an ionic liquid with which the asphaltenes and/or resins interact.Type: GrantFiled: April 1, 2008Date of Patent: May 27, 2014Assignee: ExxonMobil Research and Engineering CompanyInventors: Michael Siskin, Manuel A. Francisco, Rustom M. Billimoria
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Publication number: 20140091010Abstract: One exemplary embodiment can be a process for removing hydrogen sulfide from a fractionated hydroprocessed effluent. The process can include stripping a hydroprocessed effluent from a hydroprocessing zone, fractionating the stripped hydroprocessed effluent to obtain a naphtha cut, and sending the naphtha cut to a hydrogen sulfide removal zone. The hydrogen sulfide removal zone can include an amine wash settler, an amine contacting column, or a steam stripper.Type: ApplicationFiled: September 28, 2012Publication date: April 3, 2014Applicant: UOP, LLCInventors: Soumendra Mohan Banerjee, Srinivasa Gopalan-Rajan Varadarajan, Rajaraman Panchapakesan, Babu Balakrishnan
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Publication number: 20140084206Abstract: There is provided, in one form, a method for at least partially deactivating a sulfur species from a stream, such as but not limited to a hydrocarbon stream, an aqueous stream, and mixtures thereof. A treating mixture may be introduced into the stream in an amount effective to at least partially deactivate the sulfur species from the stream. The treating mixture may include a compound having the general formula: and combinations thereof. R1 may be a C1-C4 hydrocarbyl group. R2 may be a C1-C4 hydrocarbyl group that is the same or different as R1. R3 may be an ethanol or an isopropanol moiety. R4 may be an ethylene oxide moiety, propylene oxide moiety, butylene oxide moiety, and combinations thereof. n may be an integer from 1 to 100. M may be a hydrogen or a metal ion.Type: ApplicationFiled: September 27, 2012Publication date: March 27, 2014Applicant: BAKER HUGHES INCORPORATEDInventors: Jianzhong Yang, James Michael Brown
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Patent number: 8663457Abstract: Methods for reducing sulfides from fluid streams are provided. The methods comprise adding secondary amine-formaldehyde adduct (SAFA) scavengers to fluid streams. The SAFA scavengers added comprise less than about 40 wt % N-methyl secondary amines of the total weight of SAFA scavengers. Methods for distilling N-methyl secondary amines from secondary amine-formaldehyde adduct (SAFA) scavengers are also provided. Purified SAFA scavengers are also disclosed.Type: GrantFiled: November 23, 2011Date of Patent: March 4, 2014Assignee: General Electric CompanyInventors: Gregory Kaplan, Ping Lue
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Publication number: 20140057817Abstract: A method of reducing the amount of sulfhydryl compounds from sour hydrocarbon fluids is described. In the method, an aldehyde-releasing compound, which is high temperature stable and is highly water-soluble, is introduced to a hydrocarbon fluid stream as a scavenger for sulfhydryl compounds. The aldehyde-releasing compound is allowed to mix with the hydrocarbon fluid stream and the aldehyde-releasing compound is allowed to react with the sulfhydryl compounds present in the hydrocarbon fluid stream, thereby reducing the presence sulfhydryl compound in the hydrocarbon fluid stream.Type: ApplicationFiled: August 19, 2013Publication date: February 27, 2014Applicant: Lonza, Inc.Inventor: Kevin Edward JANAK
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Publication number: 20130334103Abstract: An apparatus and process for desulfurization of hydrocarbon feeds is disclosed in which pure nitrous oxide, or a mixture of nitrous oxide and oxygen or air, is used as a gaseous oxidant. Organosulfur compounds are converted to their corresponding oxides sulfones and/or sulfoxides in an oxidation reactor, and oxides are subsequently removed from the oxidation reactor effluent to recover a reduced sulfur-content hydrocarbon product.Type: ApplicationFiled: December 14, 2011Publication date: December 19, 2013Applicant: SAUDI ARABIAN OIL COMPANYInventors: Abdennour Bourane, Omer Refa Koseoglu
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Publication number: 20130320258Abstract: The use of a composition that includes a metal salt and an oil soluble amine formaldehyde reaction product scavenges H2S that is present in aqueous fluids (e.g. produced water liquid streams), natural gas and in oil and mixtures thereof (e.g. mixed production streams that contain all three phases) better than either component when used alone. The resulting scavenger combination significantly increases the reaction rate and the overall scavenging efficiency, i.e. capacity over each component when used alone, in the same total amount. Non-limiting examples of the metal salt include zinc or iron carboxylates, and a non-limiting example of an oil soluble amine formaldehyde reaction product is the reaction product of dibutylamine with formaldehyde.Type: ApplicationFiled: May 22, 2013Publication date: December 5, 2013Applicant: Baker Hughes IncorporatedInventors: Scott E. Lehrer, Sunder Ramachandran, Vladimir Jovancicevic
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Patent number: 8597517Abstract: A process for recovering ionic liquids comprising the steps of: providing a first ionic liquid mixture, the first ionic liquid having a halogen metallate anion, the mixture containing an organic solvent; adjusting the pH of the mixture to pH 7-10 by the addition of a base to form a first precipitate; separating the first precipitate from the mixture; removing the organic solvent from the first mixture to form a second precipitate and separating the second precipitate from the first mixture; acidifying the resulting mixture to pH 2-7 by the addition of an acid; and drying the mixture to obtain a second ionic liquid having a halogen anion.Type: GrantFiled: March 4, 2011Date of Patent: December 3, 2013Assignee: Instituto Mexicano del PetroleoInventors: Diego Javier Guzmán Lucero, Natalya Victorovna Likhanova, Rafael Martínez Palou, Eugenio Alejandro Flores Oropeza, Jorge Froylán Palomeque Santiago
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Patent number: 8580107Abstract: A process for removing a sulfur compound from a vacuum gas oil feed includes contacting the vacuum gas oil feed comprising the sulfur compound with a VGO-immiscible ionic liquid to produce a vacuum gas oil and VGO-immiscible ionic liquid mixture, and separating the mixture to produce a vacuum gas oil effluent having a reduced sulfur content relative to the vacuum gas oil feed.Type: GrantFiled: November 12, 2010Date of Patent: November 12, 2013Assignee: UOP LLCInventors: Alakananda Bhattacharyya, Manuela Serban, Beckay J. Mezza, Kurt M. Vanden Bussche, Christopher P. Nicholas, Joseph A. Kocal, Warren K. Bennion
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Patent number: 8562820Abstract: 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)2NCH2CH2CH2N?CH2.Type: GrantFiled: May 1, 2007Date of Patent: October 22, 2013Assignee: Clearwater International, L.L.C.Inventor: Larry W. Gatlin
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Patent number: 8540871Abstract: A denitrification method is disclosed for removing nitrogen compounds from a hydrocarbon feed in which the feed is contacted with an adsorbent including an organic heterocyclic salt deposited on a porous support. Additionally, a method for hydrotreating a hydrocarbon feed which includes a hydroprocessing step is disclosed, wherein prior to hydroprocessing, the feed is contacted with an adsorbent including an organic heterocyclic salt deposited on a support. Additionally, a method for producing a lube oil which includes isomerization dewaxing of a base oil fraction is disclosed, wherein prior to the isomerization dewaxing step, the base oil fraction is contacted with an adsorbent including an organic heterocyclic salt deposited on a support.Type: GrantFiled: July 30, 2010Date of Patent: September 24, 2013Assignee: Chevron U.S.A. Inc.Inventors: Bi-Zeng Zhan, Akshay Verma, Zunqing He, Zhen Zhou, Marcus Dutra e Mello, Sheila Yeh
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Publication number: 20130224092Abstract: Aldehydes useful as H2S sulfide scavengers may be corrosive to some metals such as steel, iron and aluminum, but the corrosive effect of the aldehydes may be mitigated by employing a corrosion inhibitor selected from the group consisting of a di-basic soluble phosphate salt, a tri-basic soluble phosphate salt, a phosphate ester, a thiophosphate ester, a thioamine, a Mannich Reaction Product, and combinations thereof.Type: ApplicationFiled: August 20, 2012Publication date: August 29, 2013Applicant: BAKER HUGHES INCORPORATEDInventors: Stephen R. Keenan, Jonathan Collins, Sunder Ramachandran, Vladimir Jovancicevic, Rose Tompkins, Grahame N. Taylor, Richard L. Martin, Michael L. Walker
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Patent number: 8501657Abstract: A catalyst for the desulfurization and deodorization of gasoline, which is expressed by the formula: QlBmHn[AxMyOz](1+m+n)?, where: Q denotes a quaternary ammonium cation consisting of R1R2R3R4N+, in which R1, R2, R3, and R4 each denotes independently a C1 to C20 saturated alkyl group, respectively, provided that at least one of R1, R2, R3, and R4 denotes a C4 to C20 saturated alkyl group; B denotes a metal cation of Na+ or/and K+; H denotes a hydrogen atom; A denotes a central atom of B, P, As, Si or Al; M denotes a coordinated atom of W or Mo; O denotes an oxygen atom; 1?l?10, 0?m?3, 0?n?3, l+m+n?14, x=1 or 2, 9?y?18, 34?z?62, and l, m, n, y and z all are integers. A method of the desulfurization and deodorization of gasoline by using the catalyst comprises the steps of: mixing the catalyst and an aqueous solution of hydrogen peroxide, and then adding the gasoline to react them with stirring under conditions of 25 to 90° C. and 0.1 to 1 MPa for 10 to 180 min.Type: GrantFiled: November 20, 2008Date of Patent: August 6, 2013Assignee: Dalian Institute of Chemical Physics, Chinese Academy of ScienceInventors: Can Li, Zongxuan Jiang, Yongna Zhang, Hongying Lv, Boyu Zhang
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Publication number: 20130167433Abstract: Sulfur solvent compositions are provided that have relatively low toxicity, low and not unpleasant odor, and a substantial capacity for rapidly dissolving elemental sulfur from deposits even at low temperatures and in the presence of water. The compositions comprise a reaction menstruum prepared using an amine component and a ketone component in the presence of alkanol.Type: ApplicationFiled: December 20, 2012Publication date: July 4, 2013Inventor: BRENNTAG CANADA INC.
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Publication number: 20130118955Abstract: The present invention relates to an improved desulfurization process using an ionic liquid compound of general formula C+A?, where C+ represents an organic cation such as alkyl-pyridinium, di-alkyl imidazolium and tri-alkyl imidazolium; and A? is an anion of halides of iron (III), such as, for example, FeCl4?. The desulfurization process is also improved when producing the ionic liquid compound by heating the reactants using microwave energy. The ionic liquids can be used to desulfurize hydrocarbon mixtures by a liquid-liquid extraction.Type: ApplicationFiled: January 3, 2013Publication date: May 16, 2013Applicant: INSTITUTO MEXICANO DEL PETROLEOInventor: Instituto Mexicano del Petroleo
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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: 8403043Abstract: Heavy crude oils having high sulfur content and viscosities are upgraded by a hydrodesulfurization (HDS) process that includes microwave irradiation of a mixture of the sour heavy crude oil with at least one catalyst and optionally, one or more sensitizers, and irradiation in the presence of hydrogen. The process is also adapted to microwave treatment of hard to break emulsions, either above ground or below ground where water-in-oil emulsions are initially formed, followed by the catalytic hydrodesulfurization promoted by application of further microwave energy to the demulsified crude oil stream.Type: GrantFiled: November 14, 2008Date of Patent: March 26, 2013Assignee: Saudi Arabian Oil CompanyInventors: Rashid M. Khan, Emad Naji Al-Shafei
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Patent number: 8394735Abstract: A catalyst for ultra-deep desulfurization of diesel via oxidative distillation is an amphiphilic oxidative catalyst, which is expressed as Qm[XMnOq], wherein 1?m?12; 9?n?18; 34?q?62; Q is a quaternary ammonium cation; X is P, Si, As or B; and M is Mo) or W. A desulfurization method comprises a) mixing well a diesel, the amphiphilic catalyst, and hydrogen peroxide, reacting for 10-300 minutes at ambient temperature and normal pressure, transforming the sulfur-containing compounds in the diesel into sulfone to obtain an oxidized diesel; b) distilling the oxidized diesel obtained in step a) under reduced pressure to obtain the ultra-low sulfur diesel having a sulfur content of less than 10 ppm; and c) separating and recovering the catalyst and sulfone.Type: GrantFiled: October 24, 2008Date of Patent: March 12, 2013Assignee: Dalian Institute of Chemical Physics, Chinese Academy of SciencesInventors: Zongxuan Jiang, Can Li, Yongna Zhang, Hongying Lv
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Patent number: 8366914Abstract: Compounds having the formulae and general formulae: wherein each R1, R2, R3 and R4 are the same or different and may be hydrogen, an alkyl group, an aryl group, a halogen, a nitro group, an alkyl or aryl ester, and an alkyl or aryl ether; compounds having the general formula: wherein R is an alkyl, aryl or electron withdrawing group; mixtures thereof; can be used as additives for crude oil and hydrocarbons. These compounds may be used to scavenge mercaptans, sulfides, cyanides, and primary or secondary amines; either alone or in combination.Type: GrantFiled: October 14, 2008Date of Patent: February 5, 2013Assignee: Baker Hughes IncorporatedInventors: Jianzhong Yang, Tauseef Salma, John A. Schield, Jerry J. Weers, Joseph L. Stark
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Publication number: 20130015104Abstract: A process wherein an electron donor agent is provided for the decomposition of sulfones and sulfoxides formed after the oxidative desulfurization of a sulfur-containing hydrocarbon stream.Type: ApplicationFiled: July 12, 2011Publication date: January 17, 2013Inventors: Adnan Al-Hajji, Abdennour Bourane, Omer Refa Koseoglu
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Patent number: 8343336Abstract: A high sulfur content crude oil feedstream is treated by mixing one or more selected solvents with a sulfur-containing crude oil feedstream for a predetermined period of time, allowing the mixture to separate and form a sulfur-rich solvent-containing liquid phase and a crude oil phase of substantially lowered sulfur content, withdrawing the sulfur-rich stream and regenerating the solvent, hydrotreating the remaining sulfur-rich stream to remove or substantially reduce the sulfur-containing compounds to provide a hydrotreated low sulfur content stream, and mixing the hydrotreated stream with the separated crude oil phase to thereby provide a treated crude oil product stream of substantially reduced sulfur content and without significant volume loss.Type: GrantFiled: October 30, 2007Date of Patent: January 1, 2013Assignee: Saudi Arabian Oil CompanyInventors: Esam Zaki Hamad, Emad Naji Al-Shafei, Ali Salim Al-Qahtani
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Publication number: 20120329930Abstract: An effective hydrogen sulfide scavenger that produces little corrosion may be prepared by reacting glyoxal with a compound having at least two primary or secondary amine groups. The subject hydrogen sulfide scavengers may be used with both the production of crude oil and natural gas, and the refining of same.Type: ApplicationFiled: June 19, 2012Publication date: December 27, 2012Applicant: BAKER HUGHES INCORPORATEDInventors: Joseph L. Stark, Robert A. Steele, Ksenija Babic-Samardzija, John A. Schield, Weldon J. Cappel, Matthew T. Barnes