With Nitrogen Containing Treating Reagent Patents (Class 208/236)
  • Patent number: 10308886
    Abstract: 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: Grant
    Filed: April 21, 2016
    Date of Patent: June 4, 2019
    Assignee: ECOLAB USA INC.
    Inventors: Geeta Rana, Julian M. Gallardo, Matthew Trevino
  • Patent number: 10266463
    Abstract: 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: Grant
    Filed: April 7, 2015
    Date of Patent: April 23, 2019
    Assignee: GTC Technology US LLC
    Inventors: Venkata K. Ramanujam, Michael McCaulley, Joseph C. Gentry
  • Patent number: 9920236
    Abstract: 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: Grant
    Filed: February 24, 2015
    Date of Patent: March 20, 2018
    Assignee: United Laboratories International, LLC
    Inventors: Stephen D. Matza, Martha T. Smith, Jack G. Frost
  • Patent number: 9512019
    Abstract: 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: Grant
    Filed: October 12, 2012
    Date of Patent: December 6, 2016
    Assignee: United Laboratories International, LLC
    Inventors: Stephen D. Matza, Jack G. Frost
  • Patent number: 9463989
    Abstract: 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: Grant
    Filed: June 20, 2012
    Date of Patent: October 11, 2016
    Assignee: BAKER HUGHES INCORPORATED
    Inventors: Carlos M. Menendez, Vladimir Jovancicevic, Sunder Ramachandran
  • Patent number: 9440909
    Abstract: 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: Grant
    Filed: June 30, 2015
    Date of Patent: September 13, 2016
    Assignee: General Electric Company
    Inventor: Gregory Kaplan
  • Patent number: 9394188
    Abstract: 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: Grant
    Filed: January 18, 2013
    Date of Patent: July 19, 2016
    Assignee: UOP LLC
    Inventors: Luigi Laricchia, Javier Rios
  • Patent number: 9068127
    Abstract: 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: Grant
    Filed: March 12, 2013
    Date of Patent: June 30, 2015
    Assignee: UOP LLC
    Inventors: Beckay J. Mezza, Alakananda Bhattacharyya, Christopher P. Nicholas, Haiyan Wang
  • Publication number: 20150136654
    Abstract: 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: Application
    Filed: August 28, 2014
    Publication date: May 21, 2015
  • Publication number: 20150090639
    Abstract: 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: Application
    Filed: December 8, 2014
    Publication date: April 2, 2015
    Inventors: Rafael Martinez Palou, Natalya Victorovna Likhanova, Eugenio Alejandro Flores Oropeza, Diego Javier Guzman Lucero
  • Publication number: 20140353213
    Abstract: 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: Application
    Filed: May 30, 2014
    Publication date: December 4, 2014
    Applicant: Shell Oil Company
    Inventors: John Anthony SMEGAL, Alexei Grigorievich GABRIELOV, Ed GANJA, Theofiel MEURIS
  • Patent number: 8888993
    Abstract: 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: Grant
    Filed: July 12, 2011
    Date of Patent: November 18, 2014
    Assignee: Chevron U.S.A. Inc.
    Inventors: Akshay Verma, Bi Zeng Zhan, Zunqing He, Zhen Zhou, Marcus Dutra e Mellon, Sheila Yeh
  • Patent number: 8888994
    Abstract: 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: Grant
    Filed: April 19, 2011
    Date of Patent: November 18, 2014
    Assignee: The United States of America as represented by the Administrator of the U.S. Environmental Protection Agency
    Inventors: Valerii Kukhar, Volodymir Kashkovski, Vladislav Kyselov, Yurii Besugly, Yurii Kyselov, Rajender Varma, Subhas Sikdar
  • Publication number: 20140311948
    Abstract: 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: Application
    Filed: July 1, 2014
    Publication date: October 23, 2014
    Applicant: PHILLIPS 66 COMPANY
    Inventors: John Michael Hays, Joe B. Cross
  • Publication number: 20140305844
    Abstract: 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: Application
    Filed: April 10, 2013
    Publication date: October 16, 2014
    Applicants: KING ABDULAZIZ CITY FOR SCIENCE AND TECHNOLOGY, KING FADH UNIVERSITY OF PETROLEUM AND MINERALS
    Inventors: KING FADH UNIVERSITY OF PETROLEUM AND MINERALS, KING ABDULAZIZ CITY FOR SCIENCE AND TECHNOLOGY
  • Publication number: 20140299512
    Abstract: Processes are disclosed for reducing the sulphur content of a hydrocarbon material containing sulphur compounds.
    Type: Application
    Filed: March 17, 2014
    Publication date: October 9, 2014
    Applicant: Ultraclean Fuel Pty Ltd.
    Inventors: Gordon John Gargano, Marc E. Halpern
  • Publication number: 20140299513
    Abstract: 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: Application
    Filed: April 8, 2014
    Publication date: October 9, 2014
    Applicant: Saudi Arabian Oil Company
    Inventors: Gary D. MARTINIE, Farhan M. AL-SHAHRANI, Bashir O. DABBOUSI
  • Patent number: 8845885
    Abstract: 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: Grant
    Filed: August 2, 2011
    Date of Patent: September 30, 2014
    Assignee: H R D Corporation
    Inventors: Abbas Hassan, Aziz Hassan, Rayford G. Anthony, Gregory G. Borsinger
  • Patent number: 8821716
    Abstract: 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: Grant
    Filed: May 26, 2009
    Date of Patent: September 2, 2014
    Assignee: Instituto Mexicano del Petroleo
    Inventors: Natalya Victorovna Likhanova, Rafael Martinez Palou, Jorge Froylan Palomeque Santiago
  • Patent number: 8807214
    Abstract: 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: Grant
    Filed: March 22, 2013
    Date of Patent: August 19, 2014
    Assignee: Saudi Arabian Oil Company
    Inventors: M. Rashid Khan, Emad Naji Al-Shafei
  • Publication number: 20140174987
    Abstract: 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: Application
    Filed: July 30, 2012
    Publication date: June 26, 2014
    Applicant: hte Aktiengesellschaft the high throughput experimentation company
    Inventors: Josef Find, Alfred Haas, Armin Brenner
  • Patent number: 8734639
    Abstract: 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: Grant
    Filed: April 1, 2008
    Date of Patent: May 27, 2014
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Michael Siskin, Manuel A. Francisco, Rustom M. Billimoria
  • Publication number: 20140091010
    Abstract: 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: Application
    Filed: September 28, 2012
    Publication date: April 3, 2014
    Applicant: UOP, LLC
    Inventors: Soumendra Mohan Banerjee, Srinivasa Gopalan-Rajan Varadarajan, Rajaraman Panchapakesan, Babu Balakrishnan
  • Publication number: 20140084206
    Abstract: 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: Application
    Filed: September 27, 2012
    Publication date: March 27, 2014
    Applicant: BAKER HUGHES INCORPORATED
    Inventors: Jianzhong Yang, James Michael Brown
  • Patent number: 8663457
    Abstract: 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: Grant
    Filed: November 23, 2011
    Date of Patent: March 4, 2014
    Assignee: General Electric Company
    Inventors: Gregory Kaplan, Ping Lue
  • Publication number: 20140057817
    Abstract: 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: Application
    Filed: August 19, 2013
    Publication date: February 27, 2014
    Applicant: Lonza, Inc.
    Inventor: Kevin Edward JANAK
  • Publication number: 20130334103
    Abstract: 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: Application
    Filed: December 14, 2011
    Publication date: December 19, 2013
    Applicant: SAUDI ARABIAN OIL COMPANY
    Inventors: Abdennour Bourane, Omer Refa Koseoglu
  • Publication number: 20130320258
    Abstract: 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: Application
    Filed: May 22, 2013
    Publication date: December 5, 2013
    Applicant: Baker Hughes Incorporated
    Inventors: Scott E. Lehrer, Sunder Ramachandran, Vladimir Jovancicevic
  • Patent number: 8597517
    Abstract: 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: Grant
    Filed: March 4, 2011
    Date of Patent: December 3, 2013
    Assignee: Instituto Mexicano del Petroleo
    Inventors: Diego Javier Guzmán Lucero, Natalya Victorovna Likhanova, Rafael Martínez Palou, Eugenio Alejandro Flores Oropeza, Jorge Froylán Palomeque Santiago
  • Patent number: 8580107
    Abstract: 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: Grant
    Filed: November 12, 2010
    Date of Patent: November 12, 2013
    Assignee: UOP LLC
    Inventors: Alakananda Bhattacharyya, Manuela Serban, Beckay J. Mezza, Kurt M. Vanden Bussche, Christopher P. Nicholas, Joseph A. Kocal, Warren K. Bennion
  • Patent number: 8562820
    Abstract: 1,3,5-(2H2,4H2,6H2)tripropanediamine N,N,N?,N?,N?,N? hexamethyl is used to scavenge sulfur compounds from hydrocarbons. A novel method of making the triazine comprises autocondensing (CH3)2NCH2CH2CH2N?CH2.
    Type: Grant
    Filed: May 1, 2007
    Date of Patent: October 22, 2013
    Assignee: Clearwater International, L.L.C.
    Inventor: Larry W. Gatlin
  • Patent number: 8540871
    Abstract: 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: Grant
    Filed: July 30, 2010
    Date of Patent: September 24, 2013
    Assignee: Chevron U.S.A. Inc.
    Inventors: Bi-Zeng Zhan, Akshay Verma, Zunqing He, Zhen Zhou, Marcus Dutra e Mello, Sheila Yeh
  • Publication number: 20130224092
    Abstract: 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: Application
    Filed: August 20, 2012
    Publication date: August 29, 2013
    Applicant: BAKER HUGHES INCORPORATED
    Inventors: Stephen R. Keenan, Jonathan Collins, Sunder Ramachandran, Vladimir Jovancicevic, Rose Tompkins, Grahame N. Taylor, Richard L. Martin, Michael L. Walker
  • Patent number: 8501657
    Abstract: 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: Grant
    Filed: November 20, 2008
    Date of Patent: August 6, 2013
    Assignee: Dalian Institute of Chemical Physics, Chinese Academy of Science
    Inventors: Can Li, Zongxuan Jiang, Yongna Zhang, Hongying Lv, Boyu Zhang
  • Publication number: 20130167433
    Abstract: 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: Application
    Filed: December 20, 2012
    Publication date: July 4, 2013
    Inventor: BRENNTAG CANADA INC.
  • Publication number: 20130118955
    Abstract: 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: Application
    Filed: January 3, 2013
    Publication date: May 16, 2013
    Applicant: INSTITUTO MEXICANO DEL PETROLEO
    Inventor: Instituto Mexicano del Petroleo
  • 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: 8403043
    Abstract: 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: Grant
    Filed: November 14, 2008
    Date of Patent: March 26, 2013
    Assignee: Saudi Arabian Oil Company
    Inventors: Rashid M. Khan, Emad Naji Al-Shafei
  • Patent number: 8394735
    Abstract: 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: Grant
    Filed: October 24, 2008
    Date of Patent: March 12, 2013
    Assignee: Dalian Institute of Chemical Physics, Chinese Academy of Sciences
    Inventors: Zongxuan Jiang, Can Li, Yongna Zhang, Hongying Lv
  • Patent number: 8366914
    Abstract: 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: Grant
    Filed: October 14, 2008
    Date of Patent: February 5, 2013
    Assignee: Baker Hughes Incorporated
    Inventors: Jianzhong Yang, Tauseef Salma, John A. Schield, Jerry J. Weers, Joseph L. Stark
  • Publication number: 20130015104
    Abstract: 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: Application
    Filed: July 12, 2011
    Publication date: January 17, 2013
    Inventors: Adnan Al-Hajji, Abdennour Bourane, Omer Refa Koseoglu
  • Patent number: 8343336
    Abstract: 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: Grant
    Filed: October 30, 2007
    Date of Patent: January 1, 2013
    Assignee: Saudi Arabian Oil Company
    Inventors: Esam Zaki Hamad, Emad Naji Al-Shafei, Ali Salim Al-Qahtani
  • Publication number: 20120329930
    Abstract: 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: Application
    Filed: June 19, 2012
    Publication date: December 27, 2012
    Applicant: BAKER HUGHES INCORPORATED
    Inventors: Joseph L. Stark, Robert A. Steele, Ksenija Babic-Samardzija, John A. Schield, Weldon J. Cappel, Matthew T. Barnes
  • Publication number: 20120261311
    Abstract: New sulfided metal catalysts are described, containing a metal X selected from Ni, Co and mixtures thereof, a metal Y selected from Mo, W and mixtures thereof, an element Z selected from Si, Al and mixtures thereof, and possibly an organic residue, obtained by the sulfidation of mixed oxide precursors, also new, having general formula (A) XaYbZcOd.
    Type: Application
    Filed: September 23, 2010
    Publication date: October 18, 2012
    Applicant: ENI S.p.A.
    Inventors: Giuseppe Bellussi, Angela Carati, Maria Federica Gagliardi, Stefano Zanardi, Marcello Marella, Roberto Scattolin, Michele Tomaselli
  • Publication number: 20120220500
    Abstract: A method and system remove hydrogen sulfide from a hydrocarbon containing fluid. In an embodiment, the method for removing hydrogen sulfide from a hydrocarbon containing fluid includes contacting a methylmorpholine-N-oxide solution with the hydrocarbon containing fluid. The method also includes allowing the methylmorpholine-N-oxide to react with the hydrogen sulfide to remove the hydrogen sulfide.
    Type: Application
    Filed: February 21, 2012
    Publication date: August 30, 2012
    Applicant: UNITED LABORATORIES INTERNATIONAL, LLC
    Inventors: Stephen D. Matza, Martha T. Smith, Jack G. Frost
  • Publication number: 20120091040
    Abstract: A method for desulfurization of heavy fuel oil using ferrate compounds by mixing fuel oil containing sulfur compounds with a solvent and forming a fuel oil solvent mixture, dissolving the sulfur compounds present in the fuel oil solvent mixture. Adding a liquid ferrate solution to the fuel oil solvent mixture produces oxidized sulfur compounds, in solution. An absorbing agent is added to remove thed oxidized sulfur compounds from said solution.
    Type: Application
    Filed: October 19, 2011
    Publication date: April 19, 2012
    Applicant: Florida Institute of Technology, Attention Office for Research and Technology Transfer
    Inventors: Virender K. Sharma, Abdullah Al-Abduly
  • Patent number: 8142647
    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: Grant
    Filed: December 16, 2008
    Date of Patent: March 27, 2012
    Assignee: Chevron U.S.A. Inc.
    Inventors: Xiaolin Wei, Scott M. Husson, Marcus V. Dutra e Mello, Daniel Chinn, Zunqing He
  • Publication number: 20120067781
    Abstract: The invention relates to a process and catalyst for the oxidative desulfurization of hydrocarbonaceous oil. In one aspect, solid carbon materials are provided having stable sulfur trioxide and nitrogen dioxide oxidative species on the surface thereof. Such materials are useful in the production of low sulfur hydrocarbon feedstocks and in the removal of refractory sulfur compounds.
    Type: Application
    Filed: November 28, 2011
    Publication date: March 22, 2012
    Applicant: SAUDI ARABIAN OIL COMPANY
    Inventor: Ki-Hyouk Choi
  • Patent number: 8138369
    Abstract: A process for producing an adsorbent where a metal oxide is reacted with an alkoxy silane to produce an epoxy-functionalized metal oxide. This product is reacted with an amino-substituted propionic acid and a nitro-substituted fluorenone, and this product is grafted to the epoxy-functionalized metal oxide. This grafted product is the adsorbent, which may be contacted with a hydrocarbon mixture having at least one sulfur containing compound in order to remove this sulfur containing compound. Also disclosed is a process for adding polymerization groups to an adsorbent.
    Type: Grant
    Filed: June 6, 2008
    Date of Patent: March 20, 2012
    Assignee: Chevron U.S.A. Inc.
    Inventors: Xiaolin Wei, Scott Michael Husson, Marcus V. Dutra e Mello, Daniel Chinn
  • Publication number: 20120024756
    Abstract: 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: Application
    Filed: July 12, 2011
    Publication date: February 2, 2012
    Inventors: Akshay Verma, Bi-Zeng Zhan, Zunqing He, Zhen Zhou, Marcus Dutra e Mellon, Sheila Yeh