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UNIVERSITY of ARKANSAS, Little 398:19: a 1939, Mis?Ilea US009 1691 39B2 (12) United States Patent (10) Patent No.: US 9,169,139 B2 Viswanathan (45) Date of Patent: Oct. 27, 2015 (54) USE OF MAGNETIC CARBON COMPOSITES 6,764,617 B1 7/2004 Viswanathan FROM RENEWABLE RESOURCE 7,220,484 B2 5, 2007 TOn-That MATERALS FOR OL SPLL CLEAN UP AND 7,303,6797,297,652 B2 12/200711/2007 UlicnyJhung RECOVERY 7.358525 B2 4/2008 Hayes 7,758,756 B2 7, 2010 Kim (71) Applicant: BOARD OF TRUSTEES OF THE 2002fOO64495 A1 5, 2002 Miura et al. UNIVERSITY OF ARKANSAS, Little 398:19: A 1939, Mis?ilea. Rock, AR (US) 2005/0139550 A1 6/2005 Ulicny O O 2005/0181941 A1 8/2005 Sugo et al. (72) Inventor: Tito Viswanathan, Little Rock, AR (US) 2005/0186344 A1 8/2005 Takagi 2005/0271816 A1 12/2005 Meschke (73) Assignee: BOARD OF TRUSTEES OF THE 2007/0129233 A1 6, 2007 Ueno et al. UNIVERSITY OF ARKANSAS Little 2007/O142225 A1 6/2007 Baker s 2007/0218564 A1 9/2007 Bachmann et al. Rock, AR (US) 2007/0243337 A1 10/2007 Xiong 2007,0264.574 A1 11/2007 Kim (*) Notice: Subject to any disclaimer, the term of this patent is extended or adjusted under 35 (Continued) U.S.C. 154(b) by 8 days. FOREIGN PATENT DOCUMENTS (21) Appl. No.: 14/134,992 CN 1876566. A 12/2006 CN 1911792 A 2, 2007 (22) Filed: Dec. 19, 2013 (Continued)O1 (65) Prior Publication Data OTHER PUBLICATIONS US 2014/O1 O2988 A1 Apr. 17, 2014 Antal et al., Flash carbonization of biomass, Industrial & Engineering Chemistry Research, 2003, 42(16), 3690-3699. O O Bao et al. A novel nanostructure of nickel nanotubes encapsulated in Related U.S. Application Data carbon nanotubes, Chemical Communications, Cambridge, United (60) Division of application No. 127751,185, filed on Mar. Kingdom, 2003, (2) 208-209. 31, 2010, now Pat. No. 8,647,512, which is a Bender et al., Total Phosphorous Residual Materials, In Methods of tinuation-in-part of application No. 12/487.323 Phosphorus Analysis for Soils, Sediments, Residuals, and Waters, R on Jun. 18, 2009, now abandoned s s Pierzynski, G.M., Ed. Southern Cooperative Series Bulletin No. 396. • u Y-s s 2000. (60) Provisional application No. 61/211,826, filed on Apr. She t, E. Ethi of ce E. Pt 3, 2. Ryal application No. 61/132,380, filed REE"S",anoparticles IOr Tuel cell applications, "S.S.(Cal Ommunications, On Jun. TRS, Compere et al., Low cost carbon fiber from renewable resources, Oak Ridge National Laboratory, Oak Ridge TN, USA, International (51) Int. Cl. Sampe Technical Conference, 2001, 33, 1306-1314, Society for the C: f: 3:08: Advancement of Material and Process Engineering. CO2F IOI/32 (2006.01) (Continued)Continued (52) U.S. Cl. Primary Examiner — David A Reifsnyder CPC. C02F I/48 (2013.01); C02F I/288 (2013.01); (74) Attorney, Agent, or Firm — Tim Tingkang Xia, Esq.; C02F1/488 (2013.01); C02F 2101/32 Locke Lord LLP (2013.01); C02F2305/08 (2013.01) (58) Field of Classification Search (57) ABSTRACT CPC ............ C02F 1/48; CO2F 1/288; CO2F 1/488. A method of separating a liquid hydrocarbon material from a CO2F 2305/08; CO2F 2101/32 body of water, includes: (a) mixing magnetic carbon-metal See application file for complete search history. nanocomposites with a liquid hydrocarbon material dispersed in a body of water to allow the magnetic carbon-metal nano (56) References Cited composites each to be adhered by the liquid hydrocarbon material to form a mixture; (b) applying a magnetic force to U.S. PATENT DOCUMENTS the mixture to attract the magnetic carbon-metal nanocom 3,803,033. A 4, 1974 Sutherland posites each adhered by the liquid hydrocarbon material; and 3,886,093 A 5, 1975 Dimitri (c) removing the body of water from the magnetic carbon 4,019,995 A 4/1977 Briggs metal nanocomposites each adhered by the liquid hydrocar 4,108,767 A 8/1978 Cooper bon material while maintaining the applied magnetic force. 4.457,853. A 7, 1984 Detroit The magnetic carbon-metal nanocomposites is formed by 4,985,225 A 1/1991 Hashimoto et al. 5,317,045 A 5, 1994 Clarket al. Subjecting one or more metal lignoSulfonates or metal salts to 5,604,037 A 2/1997 Ting microwave radiation, in presence of lignin/derivatives either 5,972,537 A 10, 1999 Mao in presence of alkali or a microwave absorbing material, for a 6,099,990 A 8, 2000 Denton period of time effective to allow the carbon-metal nanocom 6,232,264 B1 5, 2001 Lukehart posites to be formed. 6,486,008 B1 1 1/2002 Lee 6,733,827 B2 5, 2004 Mitchell et al. 9 Claims, 4 Drawing Sheets US 9,169,139 B2 Page 2 (56) References Cited Oyama, S. T.; Wang, X.; Requejo, F. G.; Sato, T.; Yoshimura, Y. Hydrodesulfurization of Petroleum Feedstocks with a New Type of U.S. PATENT DOCUMENTS Nonsulfide Hydrotreating Catalyst. Journal of Catalysis (2002), 209(1), 1-5. 2007/0266825 A1 1 1/2007 Ripley Oyama, S. Ted; Lee, Yong-Kul. Mechanism of Hydrodenitrogenation 2008.0017291 A1 1/2008 Shin et al. on Phosphides and Sulfides. Journal of Physical Chemistry B (2005), 2008, OO26219 A1 1/2008 Tsushima et al. 109(6), 2109-2119. 2008.0160306 A1 7/2008 Mushtaq et al. Rao et al., Synthesis of Inorganic Solids. Using Microwaves, Chem 2010/02005O1 A1 8/2010 Hoag istry of Materials, 1999, 11(4), 882-895. 2010/0283,005 A1 11/2010 Pickett et al. Shipley H.J. Yean S. Kan AT, Tomson MB, Adsorption of arsenic to magnetite nanoparticles: effect of particle concentration, pH, ionic FOREIGN PATENT DOCUMENTS strength, and temperature, Environmental Toxicology and Chemistry (2009), 28(3), 509-515. CN 101402057. A 4/2009 Vaclavikova M. Gallios GP. Hredzak S. Jakabsky S, Removal of WO 2008127757 A2 10, 2008 arsenic from water streams: an overview of available techniques, CleanTechnologies and Environmental Policy (2008), 10(1), 89-95. Vivas, N.; Bourqeois, G.; Vitry, C.; Glories, Y.; de Freitas, V., “Deter OTHER PUBLICATIONS mination of the composition of commercial tannin extracts by liquid Hu et al., Microwave-assisted synthesis of a Superparamagnetic Sur secondary ion mass spectrometry” J. Sci. Food Agric. 1996, 72, face-functionalized porous Fe3O4/C nanocomposite, Chemistry— 309-317. An Asia Journal, 2006, 1(4), 605-610. Walkiewicz et al., Microwave heating characteristics of selected min Kang et al., Obtaining carbon nanotubes from grass, Nanotechnol erals and compounds, Minerals & Metallurgical Processing, 1988, 5(1), 39-42. ogy, 2005, 16(8), 1192-1195. Wang, Xinjun; Han, Kun; Gao, Youjun, Wan, Fuquan; Jiang, Kai. Kubo et al., Carbon fibers from Lignin-recyclable plastic blends, Fabrication of novel copper phosphide (Cu3P) hollow spheres by a Encyclopedia of Chemical Processing, vol. 1, 2003, Sunggyu Lee, simple solvothermal method. Journal of Crystal Growth (2007), CRC Press pp. 317-332. 307(1), 126-130. Lagashetty et al., Microwave-assisted route for synthesis of Wei Liu et al., A Novel Carbothermal Method for the Preparation of nanosized metal oxides, Science and Technology of Advanced Mate Nano-sized WC on High Surface Area Carbon, Chemistry Letters, rials, 2007, 8(6), 484-493. 2006, 1148-1149, vol. 35. No. 10, The Chemical Society of Japan, Liu, Shuling; Liu, Xinzheng, Xu, Liqiang, Qian, Yitai; Ma, Xicheng. Tsukuba, Japan. Controlled synthesis and characterization of nickel phosphide Xie, Songhai; Qiao, Minghua; Zhou, Wuzong, Luo, Ge; He, Heyong; nanocrystal. Journal of Crystal Growth (2007), 304(2), 430-434. Fan, Kangnian; Zhao, Tiejun; Yuan, Weikang. Controlled synthesis, characterization, and crystallization of Ni-P nanospheres. Journal Marina Sofos et al., A Synergistic assembly of nanoscale lamellar of Physical Chemistry B (2005), 109(51), 24361-24368. photoconductor hybrids, Nature Materials, 2009, 68-75, vol. 8, Xu et al., Preparation and characterization of NiO nanorods by ther Nature Publishing Group. mal decomposition of NiC2O4 precursor, Journal of Materials Sci Mayo J.T.Yavuz C. Yean S. Cong L, Shipley H. Yu W. Falkner J. Kan ence, 2003, 38(4), 779-782. A, Tomson M. Colvin VL. The effect of nanocrystalline magnetite Yu et al., Microwaved-assisted synthesis and in-situ self-assembly of size on arsenic removal, Science and Technology of Advanced Mate coaxial Ag/C nanotubes, Chemical Communications, Cambridge, rials (2007), 8(1-2), 71-75. United Kingdom, 2005, 21, 2704-2706. Meng Qinghan et al., Copper-doped mesoporous activated carbons as Zhang et al., Microwave synthesis of nanocarbons from conducting electrode material for electrochemical capacitors, Journal of Applied polymers, Chemical Communications, Cambridge, United King Electrochemistry, 2006, 36(1), 63-67. dom, 2006, (23), 2477-2479. Osswald et al., Control of sp2/sp3 Carbon Ratio and Surface Chem Zhu et al., Enhanced field emission from O2 and CF4 plasma-treated istry of Nanodiamond Powders by Selective Oxidation in Air, J. Am. CuO nanowires, Chemical Physics Letters, 2006,419(4-6), 458-463. Chem. Soc., 2006, 128(35), pp. 11635-11642. Sheng, Changdong, Char Structure Characterised by Raman Spec Oyama, Novel catalysts for advanced hydroprocessing: transition troscopy and Its Correlations with Combustion Reactivity, metal phosphides, Journal of Catalysis, 2003, 216(1-2), 343-352. ScienceDirect, 2007, 23.16-2324. U.S. Patent Oct. 27, 2015 Sheet 1 of 4 US 9,169,139 B2 FIG. 1 U.S. Patent Oct. 27, 2015 Sheet 2 of 4 US 9,169,139 B2 U.S. Patent Oct. 27, 2015 Sheet 3 of 4 US 9,169,139 B2 SE Of XO, WI 5.8 in FIG. 3 US 9, 169,139 B2 1. 2 USE OF MAGNETIC CARBON COMPOSITES ticles normally used to create MR fluids, are reacted with an FROM RENEWABLE RESOURCE organic compound containing an oleophilic chain end which MATERALS FOR OL SPLL CLEAN UP AND attaches to the Surface of the iron, prior to Suspension in a RECOVERY liquid vehicle Such as an organic oil.
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