With Organic Reagent Patents (Class 208/237)
  • Patent number: 9468883
    Abstract: A solvent for removal of an acid gas from a fluid stream includes a promoter amine with a pKa of between 6.5 and 10.5 and a tertiary amine with a pKa of between 8.5 and 10.5.
    Type: Grant
    Filed: March 29, 2013
    Date of Patent: October 18, 2016
    Assignee: THE UNIVERSITY OF KENTUCKY RESEARCH FOUNDATION
    Inventors: Joseph E. Remias, Cameron A. Lippert, Kunlei Liu
  • 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
  • Patent number: 8999151
    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: Grant
    Filed: August 27, 2009
    Date of Patent: April 7, 2015
    Assignee: Instituto Mexicano del Petroleo
    Inventors: Rafael Martinez Palou, Natalya Victorovna Likhanova, Eugenio Alejandro Flores Oropeza, Diego Javier Guzman Lucero
  • Patent number: 8894843
    Abstract: A method of upgrading a heteroatom-containing hydrocarbon feed by removing heteroatom contaminants is disclosed. The method includes contacting the heteroatom-containing hydrocarbon feed with an oxidant and an immiscible acid to oxidize the heteroatoms, contacting the oxidized- heteroatom-containing hydrocarbon feed with caustic and a selectivity promoter, and removing the heteroatom contaminants from the heteroatom-containing hydrocarbon feed. The oxidant may be used in the presence of a catalyst.
    Type: Grant
    Filed: June 11, 2012
    Date of Patent: November 25, 2014
    Assignee: Auterra, Inc.
    Inventors: Jonathan P. Rankin, Jennifer L. Vreeland, Kyle E. Litz, Tracey M. Jordan, Mark N. Rossetti, Eric H. Burnett, Trent A. McCaskill
  • Patent number: 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: 8815083
    Abstract: In a process to treat gaseous components obtained from an in situ recovery of liquid hydrocarbons from a hydrocarbonaceous deposit the mercaptans and hydrogen sulfide are separated from each other using lean oil and the hydrogen sulfide further processed to obtain a sulfur-free fuel gas product. The rich oil obtained after treating the gaseous components can be used as a diluent with the liquid hydrocarbons or processed to remove and convert the mercaptans to disulfide oils.
    Type: Grant
    Filed: November 29, 2012
    Date of Patent: August 26, 2014
    Assignee: Merichem Company
    Inventor: John Watson
  • Patent number: 8721872
    Abstract: A method for thermally cracking an organic acid containing hydrocarbonaceous feed wherein the feed is first processed in a vaporization step, followed by thermal cracking.
    Type: Grant
    Filed: March 31, 2009
    Date of Patent: May 13, 2014
    Assignee: Equistar Chemicals, LP
    Inventors: Donald H. Powers, Robert S. Bridges, Kenneth M. Webber
  • Publication number: 20140001099
    Abstract: A process for removing a sulfur compound from a low nitrogen content vacuum gas oil feed includes contacting the low nitrogen content vacuum gas oil feed comprising the sulfur compound with a VGO-immiscible phosphonium ionic liquid to produce a vacuum gas oil and VGO-immiscible phosphonium ionic liquid mixture, and separating the mixture to produce a vacuum gas oil effluent having a reduced 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 treating a low nitrogen content vacuum gas oil. The low nitrogen content and especially a low level of polar nitrogen compounds increases the amount of sulfur compounds that can be removed.
    Type: Application
    Filed: May 22, 2013
    Publication date: January 2, 2014
    Applicant: UOP LLC
    Inventors: Beckay J. Mezza, Alakananda Bhattacharyya, Christopher P. Nicholas, Haiyan Wang
  • Publication number: 20140001088
    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: Application
    Filed: March 12, 2013
    Publication date: January 2, 2014
    Applicant: UOP LLC
    Inventors: Beckay J. Mezza, Alakananda Bhattacharyya, Christopher P. Nicholas, Haiyan Wang
  • Publication number: 20140001093
    Abstract: The invention involves a process for hydrocarbon conversion. The process can include providing a feed to a primary upgrading zone and then treating the product from the primary upgrading zone with a feed-immiscible ionic liquid to remove sulfur compounds.
    Type: Application
    Filed: February 6, 2013
    Publication date: January 2, 2014
    Applicant: UOP LLC
    Inventors: Beckay J. Mezza, Haiyan Wang, Christopher P. Nicholas, Alakananda Bhattacharyya, Brenna E. Huovie, Rajeswar R. Gattupalli
  • Publication number: 20130334102
    Abstract: The invention is directed towards a method of removing mercury bearing species from a hydrocarbon containing fluid. The method comprises the steps of: i) adding dithiocarbamate polymer to the fluid in an amount such that the number of mercury bonding sites on the polymer exceeds the amount of mercury atoms by at least 10% and ii) removing the mercury bearing dithiocarbamate polymer with a water/oil separation device. The invention relies upon an unexpected reversal in the solubility of dithiocarbamate polymer at very high concentrations. Because of the high solubility the polymer remains within the water phase of the hydrocarbon fluid and can be removed without the need for cumbersome precipitation methods and complicated solid liquid separation devices. As a result, the invention allows mercury contaminated crude oil to be easily rid of its mercury with easy to use equipment already present in a typical oil refinery.
    Type: Application
    Filed: August 20, 2013
    Publication date: December 19, 2013
    Applicant: Nalco Company
    Inventors: Michael L. Braden, Samuel A. Lordo
  • 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: 8557101
    Abstract: This invention relates to a process for electrochemical conversion of dibenzothiophene type molecules of petroleum feedstreams selectively to mercaptan compounds that can then be more easily removed from the electrochemically treated product stream by either caustic extraction or thermal decomposition of the thiol functionality to hydrogen sulfide. The conversion of dibenzothiophenes to mercaptans is performed by electrochemical means in the substantial absence of hydrogen and in the substantial absence of water.
    Type: Grant
    Filed: September 14, 2011
    Date of Patent: October 15, 2013
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Mark A. Greaney, Kun Wang, Frank C. Wang
  • Patent number: 8431017
    Abstract: A method for separating polar hydrocarbon compounds from a hydrocarbon oil containing polar hydrocarbon compounds comprising the steps of: a) forming a gel in the hydrocarbon oil, and thereafter b) separating the gel from the hydrocarbon oil to produce a separated gel and a separated hydrocarbon oil.
    Type: Grant
    Filed: March 29, 2010
    Date of Patent: April 30, 2013
    Assignee: ExxonMobil Research and Engineering Company
    Inventor: Ramesh Varadaraj
  • Patent number: 8357306
    Abstract: A process for removing a sulfur species from a stream selected from the group consisting of a hydrocarbon stream, an aqueous stream, and mixtures thereof is disclosed herein, which may include introducing a treating mixture into the stream. The treating mixture may include a compound of the general formula selected from the group consisting of: or combinations of compound (I) or compound (II). R1 may be a C1-C30 hydrocarbyl group that is saturated, unsaturated, cyclic or branched, or may contain a heteroatom. ‘A’ may be an oxygen atom or a methylene group. R2 may be a C1-C30 hydrocarbyl group that may be saturated, unsaturated, cyclic or branched, or may contain a heteroatom(s) other than C and H. The treating mixture may reduce the reactive sulfur species in the stream. The sulfur species reduced from the stream may be hydrogen sulfide, mercaptans, polysulfides, or combinations thereof.
    Type: Grant
    Filed: December 20, 2010
    Date of Patent: January 22, 2013
    Assignee: Baker Hughes Incorporated
    Inventors: Jianzhong Yang, Matthew T. Barnes, Joseph L. Stark
  • 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: 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
  • Patent number: 8197671
    Abstract: A method of upgrading a heteroatom-containing hydrocarbon feed by removing heteroatom contaminants is disclosed. The method includes contacting the heteroatom-containing hydrocarbon feed with an oxidant and an immiscible acid to oxidize the heteroatoms, contacting the oxidized-heteroatom-containing hydrocarbon feed with caustic and a selectivity promoter, and removing the heteroatom contaminants from the heteroatom-containing hydrocarbon feed. The oxidant may be used in the presence of a catalyst.
    Type: Grant
    Filed: December 23, 2010
    Date of Patent: June 12, 2012
    Assignee: Auterra, Inc.
    Inventors: Jonathan P. Rankin, Jennifer L. Vreeland, Kyle E. Litz, Tracey M. Jordan, Mark N. Rossetti, Eric H. Burnett
  • 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
  • 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: 20120018350
    Abstract: The desulfurization of fossil fuels is provided by the combination of fossil fuels with an aqueous mixture of ozone or hydrogen peroxide and a Tetraoctylphosphonium salt phase transfer catalyst, and the mixture is then subjected to reactive mixing to form oxidize sulfur compounds in the fuel. The polar oxidized sulfones species are removed via another mixing step. The desulfurization device can be in the form of a portable device which provides for continuous mixing-assisted desulfurization for the removal of sulfur containing compounds from fossil fuels such as diesel fuel.
    Type: Application
    Filed: July 20, 2010
    Publication date: January 26, 2012
    Inventors: Hsin Tung Lin, Meng-Wei Wan, Ming-Chun Lu
  • Patent number: 8058498
    Abstract: Process for removing oxygen-containing organic compounds from mixtures of hydrocarbon compounds, in which a liquid phase (1) containing hydrocarbons and oxygenates is charged to a first column (3), a light fraction is separated as top product (5) by distillation, and that a heavier C4+ fraction is removed from the bottom, the light fraction (5) and a gaseous mixture of hydrocarbons and oxygenates (2) is charged to a second column (7), and separated into a light and a heavy hydrocarbon fraction distillation, and an additional solvent (6) is supplied to the upper part of the second column (7), which dissolves the oxygenates and, the solvent and oxygenates being discharged as bottom product (9) and a hydrocarbon product (8), which is free from oxygenates leaves the top of the column (7). The solvent optionally is wholly or partly regenerated and recirculated to the extractive distillation column.
    Type: Grant
    Filed: October 11, 2004
    Date of Patent: November 15, 2011
    Inventors: Sandra Jensen, Martin Rothaemel, Harald Koempel, Herrmann Bach, Gerhard Birke
  • Publication number: 20110203972
    Abstract: A process for the deep desulfurisation of hydrocarbons (HC), in particular Natural Gas Condensate (NGC), and HC comprising diesel, pre-extracted diesel and naphtha, is described which is capable of reducing the sulfur content of these HC from 500 to 30 ppm. The process comprises contacting the hydrocarbon material with an oxidant selected from organic peroxy acids, organic peroxides, inorganic peroxides and mixtures thereof, in at least a stochiometric amount sufficient to oxidise a sulfur compound to a sulfone compound; contacting the hydrocarbon material with an aqueous extractant to allow at least a portion of the oxidised sulfur compounds to be extracted into the aqueous extractant, and separating the hydrocarbon material from the aqueous extractant to give a hydrocarbon material of reduced sulfur content. Optionally, the process may include a second and subsequent extractions with the aqueous extractant to further reduce sulfur content. A final extraction with an IL may be conducted.
    Type: Application
    Filed: March 21, 2007
    Publication date: August 25, 2011
    Inventors: Gordon John Gargano, Thomas Ruether, Friederike Elisabeth Agel, Andreas Bösmann
  • Patent number: 7981276
    Abstract: The present invention relates to a process for removing sulfur from sulfur-containing hydrocarbon streams utilizing a multi-ring aromatic hydrocarbon complex containing an alkali metal ion. Preferably, the sulfur-containing hydrocarbon stream is comprised of high molecular weight hydrocarbons, such as a low API gravity, high viscosity crude, tar sands bitumen, an oil derived from shale, or heavy refinery intermediate stocks such as atmospheric resids or vacuum resids which are typically difficult to desulfurize and contain relatively high amounts of sulfur. However, intermediate refinery streams and refinery product streams may also be treated by the process of the current invention to achieve very low sulfur concentrations to meet environmental specification for fuels sulfur content.
    Type: Grant
    Filed: November 30, 2007
    Date of Patent: July 19, 2011
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Michael Siskin, Ronald D Myers, Roby Bearden, Jr., Thomas B. Rauchfuss
  • Publication number: 20110021341
    Abstract: A method for separating organosulfur compounds from a liquid is provided. The method of this embodiment comprises contacting the liquid with the microporous coordination polymer to form a MCP-organosulfur inclusion compound.
    Type: Application
    Filed: October 2, 2008
    Publication date: January 27, 2011
    Applicant: THE REGENTS OF THE UNIVERSITY OF MICHIGAN
    Inventors: Adam J. Matzger, Antek G. Wong-Foy, Katie Cychosz
  • Publication number: 20110011771
    Abstract: Catalysts amenable to oxidizing sulfur compounds and systems and methods of using these catalysts to effect the removal of sulfur from crude oil and crude oil distillates are disclosed. The catalyst is disposed with a titanyl moiety which serves to selectively coordinate sulfur compounds and affect their oxidation. The titanyl may be bound within a polymer or on the surface of a polymer or on the surface or in the pores of an inorganic support. The resulting oxidized sulfur compounds are readily separated from the initial crude oil or crude oil distillate streams by traditional separation techniques arrayed as described in the systems and methods disclosed.
    Type: Application
    Filed: October 31, 2008
    Publication date: January 20, 2011
    Applicant: AUTERRA, INC.
    Inventors: Kyle E. Litz, Tracey M. Jordan, Mark N. Rossetti, Anthony J. Loughran, Jennifer L. Vreeland
  • Publication number: 20110005974
    Abstract: The present invention relates to a sulphiding agent for a hydrotreating catalyst which makes possible faster sulphiding of the catalyst but which also makes possible to very significantly limit solid deposits, in particular of sulphur. The sulphiding agent according to the invention is essentially composed of diethyl disulphide (DEDS) or dipropyl disulphide(s) (DPDS) or dibutyl disulphide(s) (DBDS) and can be employed in “in situ” and “ex situ” presulphidation processes.
    Type: Application
    Filed: August 18, 2010
    Publication date: January 13, 2011
    Applicant: Arkema France
    Inventors: Francis Humblot, Paul-Guillaume Schmitt, Georges Fremy
  • Publication number: 20110000823
    Abstract: The process of the present invention is directed to the desulfurization of a sulfur-containing hydrocarbon stream with a membrane contactor, where sulfur compounds are concentrated in a sulfur-rich stream on a permeate side of the membrane using an extractive liquid, and a sulfur-lean stream is recovered as a retentate. The sulfur-rich stream, which has a small volume relative to the original hydrocarbon stream, is conveyed to a recovery zone to recover extractive liquid, and the remaining hydrocarbon stream having an increased concentration of sulfur compounds is passed to a downstream desulfurization apparatus or system, such as a hydrotreating system, to recover the hydrocarbons associated with the organosulfur compounds.
    Type: Application
    Filed: June 29, 2010
    Publication date: January 6, 2011
    Inventors: Feras Hamad, Ahmed Bahamdan, Garba O. Yahaya, Tammana Veera Venkata Ramakrishna, Esam Z. Hamad
  • Publication number: 20100300938
    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: June 28, 2010
    Publication date: December 2, 2010
    Inventors: Gary D. Martinie, Farhan M. Al-Shahrani, Bashir O. Dabbousi
  • Patent number: 7838712
    Abstract: Disclosed is a method for steam-cracking naphtha, according to which a charge of hydrocarbons containing a portion of paraffinic naphtha, which is modified by adding a combination of a first component containing a portion of gasoline and a second component containing a portion of at least one hydrocarbonated refinery gas, and a paraffin-rich change containing at least one paraffin selected among propane, butane, or a mixture thereof are fed through a steam cracker in the presence of vapor. Also disclosed is a hydrocarbon composition suitable for steam cracking, containing a portion of a paraffinic naphtha, which is modified by adding a combination of a first component containing a portion of gasoline and a second component containing a portion of at least one hydrocarbonated refinery gas and a paraffin-rich charge containing at least one paraffin selected among propane, butane, or a mixture thereof.
    Type: Grant
    Filed: January 9, 2003
    Date of Patent: November 23, 2010
    Assignees: Total Petrochemicals Research Feluy, Total Raffinage Marketing
    Inventors: François Bouvart, Robert Duchesnes, Claude Gutle
  • Patent number: 7704380
    Abstract: In accordance with the present invention, a method of removing sulfide(s), which is safe, is effective over long periods at low cost, and exerts no adverse influences on the environment. The present invention relates to a method of removing sulfide(s), characterized in that a medium containing sulfide(s), including hydrogen sulfide and mercaptan(s), is allowed to come into contact with 2-bromo-2-nitropropane-1,3-diyl diacetate. Also, the present invention relates to the method, wherein the medium is a solid, liquid, or gas. In accordance with the present invention, sulfide(s), including hydrogen sulfide and mercaptan(s), can efficiently be treated so that they may be removed at low cost without the need for large-capacity equipment. In addition, the present invention can be safely practiced because there is no generation of byproducts that irritate the skin.
    Type: Grant
    Filed: April 5, 2005
    Date of Patent: April 27, 2010
    Assignee: K•I Chemical Industry Co., Ltd.
    Inventors: Toshihiko Shibata, Syoji Fukuyama
  • Publication number: 20100051509
    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: August 27, 2009
    Publication date: March 4, 2010
    Applicant: INSTITUTO MEXICANO DEL PETROLEO
    Inventors: Rafael Martinez Palou, Natalya Victorovna Likhanova, Eugenio Alejandro Flores Oropeza, Diego Javier Guzman Lucero
  • Patent number: 7666297
    Abstract: An improved oxidative process that employ a robust, non-aqueous, and oil-soluble organic peroxide oxidant for effective desulfurization and denitrogenation of hydrocarbons including petroleum fuels, hydrotreated vacuum gas oil (VGO), non-hydrotreated VGO, petroleum crude oil, synthetic crude oil from oil sand, and residual oil. Even at low concentrations and without the assistance of catalysts, the non-aqueous organic peroxide oxidant is extremely active and fast in oxidizing the sulfur and nitrogen compounds in the hydrocarbon feedstocks. Furthermore, the process generates a valuable organic acid by-product that is also used internally as the extractive solvent for effective removal of the oxidized sulfur and nitrogen from the hydrocarbons without the need of a final adsorption step. Novel process steps are also disclosed to substantially prevent yield loss in the oxidative process.
    Type: Grant
    Filed: December 21, 2006
    Date of Patent: February 23, 2010
    Assignee: CPC Corporation, Taiwan
    Inventors: Fu-Ming Lee, Tzong-Bin Lin, Hsun-Yi Huang, Jyh-Haur Hwang, Hung-Chung Shen, Karl Tze-Tang Chuang
  • Publication number: 20100012554
    Abstract: Naphtha is selectively hydrodesulfurized with retention of olefin content. More particularly, a CoMo metal hydrogenation component is loaded on a silica or modified silica support in the presence of an organic additive to produce a catalyst which is then used for hydrodesulfurizing naphtha while retaining olefins.
    Type: Application
    Filed: January 12, 2007
    Publication date: January 21, 2010
    Inventors: Chuansheng Bai, Stuart Soled, Sabato MIseo, Jonathan McConnachie
  • Publication number: 20090288992
    Abstract: The present invention relates to 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? and to a method of 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: May 26, 2009
    Publication date: November 26, 2009
    Applicant: INSTITUTO MEXICANO DEL PETROLEO
    Inventors: Natalya Victorovna Likhanova, Rafael Martinez Palou, Jorge Froylan Palomeque Santiago
  • Patent number: 7553406
    Abstract: This invention relates to a process for removing polarizable impurities from hydrocarbons and mixtures of hydrocarbons using ionic liquids as an extraction medium. By way of extraction, the degree of contamination of the hydrocarbon or mixture of hydrocarbons is reduced to a low or very low level. The specific ionic liquids are compounds of the Formula 1, which are organic salts that are liquid or can be melted to form a liquid and that can form at least a biphasic mixture with a hydrocarbon. The process is suitable for purifying a wide range of hydrocarbons under a wide range of process conditions.
    Type: Grant
    Filed: April 30, 2004
    Date of Patent: June 30, 2009
    Assignee: Merck Patent GmbH
    Inventors: Peter Wasserscheid, Andreas Bösmann, Andreas Jess, Leonid Datsevich, Christoph Schmitz, Andrea Wendt
  • Patent number: 7473351
    Abstract: The present invention provides a process for reducing the nitrogen content of a liquid hydrocarbon feed wherein said process comprises a) contacting a liquid hydrocarbon feed comprising an alkylating agent and organic nitrogen species with an acidic catalyst at elevated temperature in a first reaction zone to generate a liquid hydrocarbon feed comprising a reduced alkylating agent content and organic nitrogen species of higher boiling point. b) fractionating the liquid hydrocarbon feed comprising a reduced alkylating agent content and organic nitrogen species of higher boiling point to remove the organic nitrogen species of higher boiling point to generate a liquid hydrocarbon feed comprising a reduced alkylating agent content and a reduced nitrogen content.
    Type: Grant
    Filed: April 16, 2003
    Date of Patent: January 6, 2009
    Assignee: BP Corporation North America Inc.
    Inventors: Ptoshia Avon Burnett, Michael Graham Hodges, Thomas Knox
  • Publication number: 20080302704
    Abstract: A process is disclosed for removing highly deleterious non-basic nitrogen compounds upstream from an acid catalyzed thiophene alkylation process using adsorbents capable of adsorbing the non-basic nitrogen compounds.
    Type: Application
    Filed: December 22, 2005
    Publication date: December 11, 2008
    Applicant: BP Corporation North America Inc.
    Inventors: Kenneth Paul Keckler, Avelino Corma, Thomas Knox, Paul Greenough, Michael Graham Hodges
  • Patent number: 7374734
    Abstract: The disclosure relates to an absorbent for removing acid gases from fluids. The absorbent contains at least one tertiary amine, an amine which is selected from hydroxyethylpiperazine, bis(hydroxyethylpiperazine) or a mixture of these and piperazine. The absorbent may optionally contain a physical solvent for the acid gases.
    Type: Grant
    Filed: January 24, 2004
    Date of Patent: May 20, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Christoph Grossman, Norbert Asprion
  • Patent number: 7276152
    Abstract: A robust, non-aqueous, and oil-soluble organic peroxide oxidant is employed for oxidative desulfurization and denitrogenation of hydrocarbon feedstocks including petroleum fuels. Even at low concentrations, the non-aqueous organic peroxide oxidant is extremely active and fast in oxidizing the sulfur and nitrogen compounds in the hydrocarbon feedstocks without catalyst. Consequently, the oxidation reactions that employ the non-aqueous organic peroxide oxidant take place at substantially lower temperatures and shorter residence times than reactions in other oxidative desulfurization and denitrogenation processes. As a result, a higher percentage of the valuable non-sulfur and non-nitrogen containing components in the hydrocarbon feedstock are more likely preserved with the inventive process. Desulfurization and denitrogenation occur in a single phase non-aqueous environment so that no phase transfer of the oxidant is required.
    Type: Grant
    Filed: November 23, 2004
    Date of Patent: October 2, 2007
    Assignee: CPC Corporation, Taiwan
    Inventors: Tzong-Bin Lin, Hsun-Yi Huang, Jyh-Haur Hwang, Hung-Chung Shen, Karl Tze-Tang Chuang
  • Patent number: 7270737
    Abstract: For desulfurization of a hydrocarbon-containing feedstock, at least one stage for selective hydrogenation of diolefins present in the initial hydrocarbon feedstock, in the presence of a catalyst of group VIII of the period table, and a stage for extraction by a solvent of the resultant hydrogenated fraction under conditions that provide at least two fractions: a raffinate that comprises for the most part olefins, paraffins and naphthenes and a reduced amount of sulfur-containing compounds that are contained in the initial feedstock, a fraction that contains the majority of the aromatic hydrocarbons and the majority of the sulfur-containing compounds contained in the initial feedstock.
    Type: Grant
    Filed: November 13, 2003
    Date of Patent: September 18, 2007
    Assignee: Institut Francais du Petrole
    Inventors: Florent Picard, Raphaël Huyghe
  • Patent number: 7211665
    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: November 8, 2002
    Date of Patent: May 1, 2007
    Assignee: Clearwater International, L.L.C.
    Inventor: Larry W. Gatlin
  • Patent number: 7175755
    Abstract: A process for the extractive oxidation of contaminants from raw hydrocarbon streams rich in heteroatomic polar compounds is described, the said process involving the extractive oxidation of sulfur and nitrogen compounds from said streams, the said process comprising treating said streams with a peroxide solution/organic acid couple, the weight percent of the peroxide solution and organic acid based on raw hydrocarbon being at least 3 for both the peroxide and organic acid solution, under an acidic pH, atmospheric or higher pressure and ambient or higher temperature. As a result of the reaction, the oxidized heteroatomic compounds, having strong affinity for the aqueous phase, are extracted into said aqueous phase, while the oxidized hydrocarbon is neutralized, water washed and dried, the resulting end product being a hydrocarbon stream from which have been removed 88.1 wt % or more of total nitrogen compounds and basic nitrogen up to 99.1 wt %, both calculated as mass contents, total Sulfur 23.
    Type: Grant
    Filed: May 6, 2003
    Date of Patent: February 13, 2007
    Assignee: Petroleo Brasileiro S.A.-Petrobras
    Inventor: Wladmir Ferraz de Souza
  • Patent number: 7001504
    Abstract: A process for the removal of organosulfur compounds from hydrocarbon materials is disclosed. The process includes contacting an ionic liquid with a hydrocarbon material to extract sulfur-containing compounds into the ionic liquid. The sulfur-containing compounds can be partially oxidized to sulfoxides and/or sulfones prior to or during the extraction step.
    Type: Grant
    Filed: November 6, 2002
    Date of Patent: February 21, 2006
    Assignee: Extractica, LLC.
    Inventor: Roger E. Schoonover
  • Patent number: 6923904
    Abstract: The invention pertains to a process for reducing the sulfur content of a hydrocarbon feedstock to a value of less than 200 ppm, preferably less than 50 ppm, which comprises subjecting a catalyst comprising a Group VIB metal component, a Group VIII metal component, and an organic additive on a carrier to a sulfidation step, and contacting a feedstock with a 95% boiling point of 450° C. or less and a sulfur content of 500 ppm or less with the sulfided catalyst under conditions of elevated temperature and pressure to form a product with a sulfur content of less than 200 ppm. The organic additive preferably is at least one compound selected from the group of compounds comprising at least two hydroxyl groups and 2-10 carbon atoms, and the (poly)ethers of these compounds.
    Type: Grant
    Filed: March 31, 2000
    Date of Patent: August 2, 2005
    Assignee: Akso Nobel N.V.
    Inventors: Frans Lodewijk Plantenga, Franciscus Wilhelmus Van Houtert, Johannes Wilhelmus Maria Sonnemans
  • Patent number: 6827844
    Abstract: Fossil fuels are combined with an aqueous liquid and a dialkyl ether to form an aqueous-organic reaction medium which is passed through an ultrasound chamber on a continuous flow-through basis. The emerging mixture separates spontaneously into aqueous and organic phases, from which the organic phase is readily isolated as the desulfurized fossil fuel.
    Type: Grant
    Filed: October 23, 2002
    Date of Patent: December 7, 2004
    Assignee: SulphCo, Inc.
    Inventor: Rudolf W. Gunnerman
  • Publication number: 20040222134
    Abstract: A process for the extractive oxidation of contaminants from raw hydrocarbon streams rich in heteroatomic polar compounds is described, the said process involving the extractive oxidation of sulfur and nitrogen compounds from said streams, the said process comprising treating said streams with a peroxide solution/organic acid couple, the weight percent of the peroxide solution and organic acid based on raw hydrocarbon being at least 3 for both the peroxide and organic acid solution, under an acidic pH, atmospheric or higher pressure and ambient or higher temperature. As a result of the reaction, the oxidized heteroatomic compounds, having strong affinity for the aqueous phase, are extracted into said aqueous phase, while the oxidized hydrocarbon is neutralized, water washed and dried, the resulting end product being a hydrocarbon stream from which have been removed 88.1 wt % or more of total nitrogen compounds and basic nitrogen up to 99.1 wt %, both calculated as mass contents, total Sulfur 23.
    Type: Application
    Filed: May 6, 2003
    Publication date: November 11, 2004
    Applicant: PETROLEO BRASILEIRO S.A. - PETROBRAS
    Inventor: Wladmir Ferraz de Souza
  • Patent number: 6802959
    Abstract: A process for separating olefins from sulfur-containing hydrocarbons contained in a hydrocarbon feedstock is disclosed and includes contacting the hydrocarbon feedstock with N-hydroxyethyl pyrollidone in a contacting zone, removing at least one olefin overhead from the contacting zone, and removing at least a portion of the sulfur-containing hydrocarbons off the bottom of the contacting zone along with the N-hydroxyethyl pyrollidone.
    Type: Grant
    Filed: June 23, 2000
    Date of Patent: October 12, 2004
    Assignee: ConocoPhillips Company
    Inventor: Ronald E. Brown
  • Patent number: 6740230
    Abstract: The disclosure concerns a process for removing mercaptans from fluid streams comprising same, especially from hydrocarbon gas streams, for example natural gas, synthesis gas from heavy oil or heavy residues or refinery gas, or else from liquid hydrocarbons, for example LPG (liquefied petroleum gas). The invention comprises intimately contacting the fluid stream in an absorption or extraction zone with a scrubbing liquor comprising at least one aliphatic alkanolamine of 2-12 carbon atoms, the amount of wash liquor being supplied to the absorption or extraction zone being sufficient to remove at least CO2 and H2S essentially completely from the fluid stream, and separating the substantially decontaminated fluid stream and the contaminated wash liquor and discharging them from the absorption zone.
    Type: Grant
    Filed: January 9, 2002
    Date of Patent: May 25, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Randolf Hugo, Rupert Wagner, Thomas S. Holst, Christoph Grossmann
  • Patent number: 6736963
    Abstract: Economical processes are disclosed for the production of fuels of reduced sulfur content from a feedstock, typically derived from natural petroleum, wherein the feedstock is comprised of limited amounts of sulfur-containing organic compounds as unwanted impurities. The processes involve an integrated, multiple stage system for converting these impurities to higher boiling products by alkylation and removing the higher boiling products by fractional distillation. Advantageously, the processes include selective hydrogenation of the high-boiling fraction whereby the incorporation of hydrogen into hydrocarbon compounds, sulfur-containing organic compounds, and/or nitrogen-containing organic compounds assists by hydrogenation removal of sulfur and/or nitrogen. Products can be used directly as transportation fuels and/or blending components to provide, for example, more suitable components for blending into fuels which are more friendly to the environment.
    Type: Grant
    Filed: July 31, 2001
    Date of Patent: May 18, 2004
    Assignee: BP Corporation North America Inc.
    Inventors: Vivek R. Pradhan, Ptoshia A. Burnett, Stacey McDaniel, Michael Hodges