Separation of Hydrocarbons by Means of Liquid-Liquid Extraction with Deep Eutectic Solvents

References

• Anastas, P.; Eghbali, N. Green chemistry: Principles and practice. Chem. Soc. Rev. 2010, 39, 301–312.
   PubMed Web of Science ®Google Scholar
• Hayyan, M.; Hashim, M. A.; Hayyan, A.; Al-Saadi, M. A.; AlNashef, I. M.; Mirghani, M. E. S.; Kola Sahee, O. K. Are deep eutectic solvents benign or toxic? Chemosphere 2013, 90, 2193–2195.
   PubMed Web of Science ®Google Scholar
• Welton, T. Room-temperature ionic liquids: Solvents for synthesis and catalysis. Chem. Rev. 1999, 99, 2071–2084.
   PubMed Web of Science ®Google Scholar
• Visser, A. E.; Swatloski, R. P.; Rogers, R. D. pH-Dependent partitioning in room temperature ionic liquids. Green Chem. 2000, 2, 1–4.
   Web of Science ®Google Scholar
• Li, C.; Li, D.; Zou, S.; Li, Z.; Yin, J.; Wang, A.; Cui, Y.; Yao, Z.; Zhao, Q. Extraction desulfurization process of fuels with ammonium-based deep eutectic solvents. Green Chem. 2013, 15, 2793–2799.
   Web of Science ®Google Scholar
• Stolte, S.; Arning, J.; Thöming, J. Biologische Abbaubarkeit von ionischen Flüssigkeiten–Testverfahren und strukturelles design. Chem. Ing. Tech. 2011, 83, 1454–1467.
   Web of Science ®Google Scholar
• Petković, M.; Seddon, K. R.; Rebelo, L. P. N.; Silva Pereira C. Ionic liquids: A pathway to environmental acceptability. Chem. Soc. Rev. 2011, 40, 1383–1403.
   PubMed Web of Science ®Google Scholar
• Plechkova, N. V.; Seddon, K. R. Applications of ionic liquids in the chemical industry. Chem. Soc. Rev. 2008, 37, 123–150.
   PubMed Web of Science ®Google Scholar
• Zhao, D.; Liao, Y.; Zhang, Z. Toxicity of ionic liquids. CLEAN – Soil, Air, Water 2007, 35, 42–48.
   Web of Science ®Google Scholar
• Pham, T. P. T.; Cho, C.-W.; Yun, Y.-S. Environmental fate and toxicity of ionic liquids: A review. Water Res. 2010, 44, 352–372.
   PubMed Web of Science ®Google Scholar
• Romero, A.; Santos, A.; Tojo, J.; Rodríguez, A. Toxicity and biodegradability of imidazolium ionic liquids, J. Hazard. Mater. 2008, 151, 268–273.
   PubMed Web of Science ®Google Scholar
• Alvarez-Guerra, M.; Irabien, A. Design of ionic liquids: An ecotoxicity (Vibrio fischeri) discrimination approach. Green Chem. 2011, 13, 1507–1516.
   Web of Science ®Google Scholar
• Wood, N.; Stephens, G. Accelerating the discovery of biocompatible ionic liquids. Phys. Chem. Chem. Phys. 2010, 12, 1670–1674.
   Google Scholar
• Pandey, A.; Pandey, S. Solvatochromic probe behavior within choline chloride-based deep eutectic solvents: Effect of temperature and water. J. Phys. Chem. B 2014, 118, 14652−14661.
   PubMed Web of Science ®Google Scholar
• Abbott, A. P.; Harris, R. C.; Ryder, K. S.; D’Agostino, C.; Gladden, L. F.; Mantle, M. D. Glycerol eutectics as sustainable solvent systems. Green Chem. 2011, 13, 82–90.
   Web of Science ®Google Scholar
• Yu, Y.; Lu, X.; Zhou, Q.; Dong, K.; Yao, H.; Zhang, S. Biodegradable naphthenic acid ionic liquids: Synthesis, characterization, and quantitative structure-biodegradation relationship. Chem.-Eur. J. 2008, 14, 11174–11182.
   PubMed Web of Science ®Google Scholar
• Tang, S.; Baker, G. A.; Zhao, H. Ether- and alcohol-functionalized task-specific ionic liquids: Attractive properties and applications. Chem. Soc. Rev. 2012, 41, 4030–4066.
   PubMed Web of Science ®Google Scholar
• Hizaddin, H. F.; Sarwono, M.; Hashim, M. A.; Alnashef, I. M.; Hadj-Kali, M. K. O. Coupling the capabilities of different complexing agents into deep eutectic solvents to enhance the separation of aromatics from aliphatics. J. Chem. Thermodyn. 2015, 84, 67–75.
   Web of Science ®Google Scholar
• Kareem, M. A.; Mjalli, F. S.; Ali Hashim, M.; Hadj-Kali, M. K. O.; Bagh, F. S. G.; Alnashef, I. M. Phase equilibria of toluene/heptane with deep eutectic solvents based on ethyltriphenylphosphonium iodide for the potential use in the separation of aromatics from naphtha. J. Chem. Thermodyn. 2013, 65, 138–149.
   Web of Science ®Google Scholar
• Kareem, M. A.; Mjalli, F. S.; Ali Hashima, M.; Al Nashef, I. M. Liquid–liquid equilibria for the ternary system (phosphonium based deep eutectic solvent–benzene–hexane) at different temperatures: A new solvent introduced. Fluid Phase Equilib. 2012, 314, 52–59.
   Web of Science ®Google Scholar
• Kareem, M. A.; Mjalli, F. S.; Ali Hashima, M.; Hadj-Kali, M. K. O. Bagh, F. S. G.; Al Nashef, I. M. Phase equilibria of toluene/heptane with tetrabutylphosphonium bromide based deep eutectic solvents for the potential use in the separation of aromatics from naphtha. Fluid Phase Equilib. 2012, 333, 47–54.
   Web of Science ®Google Scholar
• Mulyono, S.; Hizaddin, H. F.; Alnashef, I. M.; Hashim, M. A.; Fakeeha, A. H.; Hadj-Kali, M. K. Separation of BTEX aromatics from n-octane using a (tetrabutylammonium bromide + sulfolane) deep eutectic solvent experiments and COSMO-RS prediction. RSC Adv. 2014, 4, 17597–17606.
   Web of Science ®Google Scholar
• Oliveira, F. S.; Pereiro, A. B.; Rebelo, L. P. N.; Marrucho, I. M. Deep eutectic solvents as extraction media for azeotropic mixtures. Green Chem. 2013, 15, 1326–1330.
   Web of Science ®Google Scholar
• Rodriguez, N. R.; Santacruz Molina, B.; Kroon, M. C. Aliphatic + ethanol separation via liquid–liquid extraction using low transition temperature mixtures as extracting agents. Fluid Phase Equilib. 2015, 394, 71–82.
   Web of Science ®Google Scholar
• Jiao, T.; Li, C.; Zhuang, X.; Cao, S.; Chen, H.; Zhang, S. The new liquid–liquid extraction method for separation of phenolic compounds from coal tar. Chem. Eng. J. 2015, 266, 148–155.
   Web of Science ®Google Scholar
• Jiao, T.; Zhuang, X.; He, H.; Li, C.; Chen, H.; Zhang, S. Separation of phenolic compounds from coal tar via liquid–liquid extraction using amide compounds. Ind. Eng. Chem. Res. 2015, 54, 2573–2579.
   Web of Science ®Google Scholar
• Gonzalez, A. S. B.; Francisco, M.; Jimeno, G.; Lago García de Dios, S.; Kroon, M. C. Liquid–liquid equilibrium data for the systems {LTTM + benzene + hexane} and {LTTM + ethyl acetate + hexane} at different temperatures and atmospheric pressure. Fluid Phase Equilib. 2013, 360, 54–62.
   Web of Science ®Google Scholar
• Tang, X.-D.; Zhang, Y.-F.; Li, J.-J.; Zhu, Y.-Q.; Qing, D.-Y.; Deng, Y.-X. Deep extractive desulfurization with arenium ion deep eutectic solvents. Ind. Eng. Chem. Res. 2015, 54, 4625–4632.
   Web of Science ®Google Scholar
• Gano, Z. S.; Mjalli, F. S.; Al-Wahaibi, T.; Al-Wahaibi, Y.; AlNashef, I. M. Extractive desulfurization of liquid fuel with FeCl3;-based deep eutectic solvents: Experimental design and optimization by central-composite design. Chem. Eng. Process. 2015, 93, 10–20.
   Web of Science ®Google Scholar
• Zhu, W.; Wang, C.; Li, H.; Wu, P.; Xun, S.; Jiang, W.; Chen, Z.; Zhao, Z.; Li, H. One-pot extraction combined with metal-free photochemical aerobic oxidative desulfurization in deep eutectic solvent. Green Chem. 2015, 17, 2464–2472.
   Web of Science ®Google Scholar
• Cooper, E. R.; Andrews, C. D.; Wheatly, P. S.; Webb, P. B.; Wormald, P.; Morris, R. E., Ionic liquids and eutectic mixtures as solvent and template in synthesis of zeolite analogues. Nature 2004, 430, 1012–1016.
   PubMed Web of Science ®Google Scholar
• Hayyan, M.; Mjalli, F.S.; Hashim, M. A.; AlNashef, I. M. A novel technique for separating glycerine from palm oil-based biodiesel using ionic liquids. Fuel Process. Technol. 2010, 91, 116–120.
   Web of Science ®Google Scholar
• Shahbaz, K.; Baroutian, S.; Mjalli, F. S.; Hashim, M. A.; AlNashef, I. M. Densities of ammonium and phosphonium based deep eutectic solvents: Prediction using artificial intelligence and group contribution techniques. Thermochim. Acta 2012, 527, 59–66.
   Web of Science ®Google Scholar
• Shahbaz, K.; Mjalli, F. S.; Hashim, M. A; AlNashef, I. M., Prediction of deep eutectic solvents densities at different temperatures. Thermochim. Acta 2011, 515, 67–72.
   Web of Science ®Google Scholar
• Leron, R. B.; Soriano, A. N.; Li, M.-H. Densities and refractive indices of the deep eutectic solvents (choline chloride + ethylene glycol or glycerol) and their aqueous mixtures at the temperature ranging from 298.15 to 333.15 K. J. Taiwan Inst. Chem. Eng. 2012, 43, 551–557.
   Web of Science ®Google Scholar
• Rogošić, M.; Sander, A.; Pantaler, M. Application of 1-pentyl-3-methylimidazolium bis(trifluoromethylsulfonyl) imide for desulfurization, denitrification and dearomatization of FCC gasoline. J. Chem. Thermodyn. 2014, 76, 1–15.
   Web of Science ®Google Scholar
• García, G.; Aparicio, S.; Ullah, R.; Atilhan, M. Deep eutectic solvents: Physicochemical properties and gas separation applications. Energy Fuels 2015, 29, 2616−2644.
   Web of Science ®Google Scholar
• Abbott, A. P.; Barron, J. C.; Frisch, G.; Gurman, S.; Ryder, K. S.; Silva, A. F. Double layer effects on metal nucleation in deep eutectic solvents. Phys. Chem. Chem. Phys. 2011, 13, 10224–10231.
   PubMed Web of Science ®Google Scholar
• Renon, H.; Prausnitz, J.M. Local composition in thermodynamic excess functions for liquid mixtures. AIChE J. 1968, 14, 135–144.
   Web of Science ®Google Scholar
• Sorensen, J. M.; Arlt, W. DECHEMA Chemistry Data Series, Vol. V (Liquid-Liquid Equilibrium), 3 Bände, Frankfurt, 1979.
   Google Scholar
• Pandey, A.; Rai, R.; Pal, M.; Pandey, S. How polar are choline chloride-based deep eutectic solvents? Phys. Chem. Chem. Phys. 2014, 16, 1559–1568.
   PubMed Web of Science ®Google Scholar
• Gorke, J. T.; Srienc, F.; Kazlauskas, R. J. Hydrolase-catalyzed biotransformations in deep eutectic solvents. Chem. Commun. 2008, 10, 1235–1237.
   PubMed Web of Science ®Google Scholar
• Casal, M. F. Desulfurization of fuel oils by solvent extraction with ionic liquids, PhD thesis, University of Santiago de Compostela, Santiago de Compostela, 2010.
   Google Scholar
• D’Agostino, C.; Harris, R. C.; Abbott, A. P.; Gladden, L- F.; Mantle, M. D. Molecular motion and ion diffusion in choline chloride based deep eutectic solvents studied by 1H pulsed field gradient NMR spectroscopy. Phys. Chem. Chem. Phys. 2011, 13, 21383–21391.
   PubMed Web of Science ®Google Scholar