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(12) United States Patent (10) Patent No.: US 9,441,169 B2 Gargano Et Al

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(12) United States Patent (10) Patent No.: US 9,441,169 B2 Gargano Et Al USOO94411 69B2 (12) United States Patent (10) Patent No.: US 9,441,169 B2 Gargano et al. (45) Date of Patent: Sep. 13, 2016 (54) PROCESS FOR REMOVING SULPHUR (58) Field of Classification Search COMPOUNDS FROM HYDROCARBONS CPC ....... C10G 27/00; C10G 27/02: C10G 27/12 See application file for complete search history. (71) Applicant: Ultraclean Fuel Pty Ltd., Tuggerah New South Wales (AU) (56) References Cited (72) Inventors: Gordon John Gargano, Mardi (AU); U.S. PATENT DOCUMENTS Marc E. Halpern, Blackwood, NJ (US) 4,727,973 A 3, 1988 Estreicher et al. (73) Assignee: ULTRACLEAN FUEL PTY LTD, As A t 1858 sman Tuggerah, New South Wales (AU) 6,171.478 B1 1/2001 CabreraOe et al. 6,274,785 B1 8, 2001 G (*) Notice: Subject to any disclaimer, the term of this 6,277,271 B1 8, 2001 k patent is extended or adjusted under 35 6,402,939 B1 6/2002 Yen et al. U.S.C. 154(b) by 154 days. 6,406,616 B1 6/2002 Rappas et al. (Continued) (21) Appl. No.: 14/216,602 (22) Filed Mar 17, 2014 FOREIGN PATENT DOCUMENTS 1C ar. If AU 200020723 9, 2001 (65) Prior Publication Data CA 1213918 11, 1986 US 2014/02995 12 A1 Oct. 9, 2014 (Continued) Related U.S. Application Data OTHER PUBLICATIONS (60) Provisional application No. 61/790,749, filed on Mar. Arlt et al.; New classes of compounds for chemical engineering: 15, 2013. ionic liquids and hyperbranched polymers; research paper; Upon s knowledge and belief prior to Mar. 17, 2014; 13 pages; Technical (51) Int. Cl. University of Berlin, Institute fuer Verfahrenstechnik, Berlin, Ger CIOG 27/00 (2006.01) many. CIOG 27/12 (2006.01) (Continued) CIOG 27/04 (2006.01) CIDG 25/00 (2006.01) CIDG 25/12 (2006.01) Primary Examiner — Brian McCaig CIOG 53/14 (2006.01) (74) Attorney, Agent, or Firm — Thorpe North & Western CIOG 2/06 (2006.01) LLP CIOG 27/02 (2006.01) (52) U.S. Cl. (57) ABSTRACT CPC ............... CI0G 27/04 (2013.01): CI0G 21/06 (2013.01): CI0G 25/003 (2013.01); CIOG Processes are disclosed for reducing the sulphur content of 25/12 (201301): CIOG 27/2 (201301). a hydrocarbon material containing Sulphur compounds. CI0G 53/14 (2013.01); C10G 2300/202 (2013.01) 60 Claims, 3 Drawing Sheets Sluf General Process Arrangement ". 9 S. son H Q:ticiani -- E s X i * Y t L or Pols Stroxtor Nitrogen H U.S. &this Sai Sod in Sitte Sedrale US 9,441,169 B2 Page 2 (56) References Cited WO WO O1/48119 T 2001 WO WO O2, 18518 3, 2002 U.S. PATENT DOCUMENTS WO WO O2/49992 6, 2002 WO WO O2/O92204 11 2002 6,596,914 B2 it 7/2003 Gore WO WO O3,O39719 5, 2003 6,881,325 B2 4/2005 Morris et al. WO WO O3/106379 12/2003 7,001,504 B2 2/2006 Schoonover WO WO 2004/035542 4/2004 7, 175,755 B2 2/2007 De Souza WO WO 2004/067487 8, 2004 7,744,749 B2 6/2010 Martinie WO WO 2005/O14547 2, 2005 7,790,021 B2 it 9/2010 Kocal WO WO 2005/023422 3, 2005 7.914,669 B2 * 3/2011 Martinie ................ C10G 2106 WO WO 2005/113702 12/2005 208,208 R WO WO 2005/113729 12/2005 2002/0029997 A1 3/2002 Rappas et al. WO WO 2006/0873.33 8, 2006 2002fO148756 A1 10, 2002 Morris et al. 2003/008515.6 A1 5, 2003 Schoonover OTHER PUBLICATIONS 2003. O149264 A1 8/2003 Boesmann Bossmann et al.; Deep desulfurization of diesel fuel by extraction 2004/0096932 A1 5/2004 Kragl et al. 2004/O118750 A1 6/2004 Gong et al. with ionic liquids; Chemical Communications; 2001; pp. 2494 2004/0262578 A1 12/2004 Boesmann 2495; The Royal Society of Chemistry. 2005/0010.076 A1 1/2005 Wasserscheid et al. Deshpande et al.; Ultrasound-Assisted, Base-Catalyzed Oxidation 2005/0070717 A1 3/2005 Boesmann of 4,6-Dimethyldibenzothiophene in a Biphasic Diesel-Acetonitrile 2005/0O85671 A1 4/2005 Bohnen et al. System; Energy & Fuels; 2005; pp. 28-34; vol. 19, No. 1; American 2005/0090704 A1 4/2005 Roettger et al. Chemical Society. 2005/011951.6 A1 6, 2005 Bollman Huang et al.; Desulfurization of Gasoline by Extraction with New 2005/0287677 A1 12, 2005 BoeSmann Ionic Liquids; Energy & Fuels; 2004; pp. 1862-1864; vol. 18, No. 2006, OO63945 A1 3, 2006 Wasserscheid et al. 6; American Chemical Society. 2007/0051667 A1 3, 2007 Martinie et al. Kanel; Overview: Industrial Application of Ionic Liquids for Liquid 2007/022795.0 A1 10, 2007 Martinie et al. Extraction; Chemical Industry Vision 2020 Technology Partnership 2009, OO65399 A1 3, 2009 Kocal et al. Workshop Sep. 11, 2003 Power Point presentation; May 19, 2004; 2009,0242459 A1 10, 2009 Soloveichik et al. 15 pages; J.S. Kanel & Associates, LLC. 2011/02O3972 A1 8, 2011 Gargano et al. Lo et al.; One-pot desulfurization of light oils by chemical oxidation 2012fOO1835.0 A1 1, 2012 Lin et al. and solvent extraction with room temperature ionic liquids; Green 2012/009 1040 A1 4, 2012 Sharma et al. Chemistry; 20003; pp. 639-642; vol. 5: The Royal Society of 2012/0138449 A1 it 6, 2012 Basfar Chemistry. Minkel; Pinching Out Sulfur, Refining Ways to Turn Heavy Oil into FOREIGN PATENT DOCUMENTS Sweet Crude: Scientific American; Feb. 2006; pp. 25-27; Scientific American, Inc. CN 1712497 A 12/2005 CN 101851529 A 1, 2010 Zhang et al.; Extraction Desulfurization and Denitrogenation of DE 4014176 11, 1991 Fuels Using Ionic Liquids; Industrial & Engineering Chemistry DE 1990.1524 T 2000 Research; 2004; pp. 614-622; vol. 43; American Chemical Society. DE 19926924 1, 2001 Jiang et al., Oxidative Desulfurization of Fuel Oils, pp. 707-715, DE 10132526 1, 2003 2011, Chinese Journal of Catalysis. DE 102004O2.7196 12/2005 Liu et al., Deep Desulfurization of Diesel Oil Oxidized by Fe (VI) DE 102004.033021 2, 2006 Systems, pp. 422-428, 2008, Fuel. DE 102004O24968 3, 2006 Fukuda et al., Imide-Catalyzed Oxidation System: Sulfides to DE 1020050O8406 4/2006 Sulfoxides and Sulfones, pp. 4629-4631, 2010, J. Org. Chem. EP O565324 A1 10, 1993 Ishihara et al., Oxidative Desulfurization and Denitrogenation of a EP 11821.96 2, 2002 Light Gas Oil Using an Oxidation/Adsorption Continuous Flow EP 1182197 2, 2002 Process, pp. 279-287, 2004, Applied Catalysis a: General. EP 16793O7 T 2006 JP 2001.322953. A 11 2001 Zhang et al., Research Advances in Oxidative Desulfurization WO WO 98.47616 10, 1998 Technologies for the Production of Low Sulfur Fuel Oils, pp. WO WOOOf 16902 3, 2000 196-207, 2009, Petroleum & Coal. WO WOOOf2O115 4/2000 WO WOOOf 34211 6, 2000 * cited by examiner WO WOOOf 41809 T 2000 it cited by third party U.S. Patent Sep. 13, 2016 Sheet 1 of 3 US 9,441,169 B2 |eun61– U.S. Patent Sep. 13, 2016 Sheet 2 of 3 US 9,441,169 B2 un?dInSu81H uoquepoupÁH U.S. Patent Sep. 13, 2016 Sheet 3 of 3 US 9,441,169 B2 t i US 9,441,169 B2 1. 2 PROCESS FOR REMOVING SULPHUR cling. In some embodiments, ultra low Sulphur hydrocarbon COMPOUNDS FROM HYDROCARBONS and ultra low Sulphur aromatic hydrocarbon streams are produced. The present application claims the benefit of U.S. Provi Accordingly, in at least a preferred embodiment, the sional Patent Application No. 61/790,749 filed on Mar. 15, process of the present invention advantageously provides an 2013, the entirety of which is incorporated herein by refer economically viable way of reducing Sulphur levels in liquid CCC. hydrocarbons containing a variety of Sulphur species to produce recyclable hydrocarbon streams, very low waste FIELD streams and minimal loss of hydrocarbon components. 10 In a first aspect there is provided a process for reducing The present invention relates to the removal of sulphur the Sulphur content of a hydrocarbon material containing compounds from hydrocarbon streams. Sulphur compounds, the process comprising: a) contacting the hydrocarbon material with one or more BACKGROUND primary oxidants to oxidize the Sulphur compounds to 15 Sulphoxide and/or Sulphone compounds to provide a pri The removal of sulphur compounds from fossil hydrocar mary oxidised hydrocarbon material, wherein the primary bon (HC) streams, such as Natural Gas Condensate, Kero oxidants have an ORP of up to about 1550 mV; sene, Jet Fuel, Diesel and Fuel Oil, down to ultra low ppm b) contacting the primary oxidised hydrocarbon material levels is of major technical importance in industry and with a secondary oxidant to oxidize Sulphur compounds not Society due to the fact that Sulphur containing compounds oxidised by the primary oxidant to sulphoxide and/or sul can have negative effects on technical operations and the phone compounds to provide a secondary oxidised hydro environment. For instance, the presence of chemically carbon material, wherein the secondary oxidant has an ORP combined Sulphur, Such as organosulphur compounds, in of greater than about 1550 mV; hydrocarbon streams can cause corrosion of processing 25 c) contacting the primary and/or secondary oxidised equipment and engine parts. Further, the emission of SO, hydrocarbon material with an aqueous extractant to allow at and NO (oxides of nitrogen and sulphur) from the combus least a portion of the Sulphoxide and/or Sulphone compounds tion of fossil fuels containing Sulphur and nitrogen, causes to be extracted into the aqueous extractant to give a Sul damage to the environment. Of particular concern is the phoxide and/or Sulphone stream and a low Sulphur hydro presence of Poly Nuclear Aromatics (PAH) Sulphur, which 30 carbon stream; and when combusted, can produce toxic and probable carcino d) contacting the Sulphoxide and/or Sulphone stream with genic compounds in the environment.
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