Removal of Thiophene from Mixtures with n-Heptane by Selective Extraction Using Deep Eutectic Solvents

Industrial and Engineering Chemistry Research

Volumn 55, Issue 30, 2016, Pages 8415-8423

  Hadj Kali, Mohamed K ^a   Mulyono, Sarwono ^a   Hizaddin, Hanee F ^b   Wazeer, Irfan ^a   El Blidi, Lahssen ^a   Ali, Emad ^a   Hashim, Mohd Ali ^b   AlNashef, Inas M ^c  

^a KING SAUD UNIVERSITY   (Saudi Arabia)

^b UNIVERSITY OF MALAYA   (Malaysia)

^c KHALIFA UNIVERSITY   (United Arab Emirates)

Author keywords

[No Author keywords available]

Indexed keywords

EFFICIENCY; ETHYLENE; ETHYLENE GLYCOL; EUTECTICS; HEPTANE; THIOPHENE;

DEEP EUTECTIC SOLVENTS; EXTRACTION EFFICIENCIES; EXTRACTION MECHANISMS; EXTRACTION PROCESS; ROOT MEAN SQUARE DEVIATIONS; SELECTIVE EXTRACTION; SIMULATION ANALYSIS; TETRABUTYLAMMONIUM BROMIDE;

EXTRACTION;

EID: 84982712610     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/acs.iecr.6b01654     Document Type: Article

References (39)

1. 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 10.1039/c3gc41067f
2. Ban, L. L.; Liu, P.; Ma, C. H.; Dai, B. Deep Extractive Desulfurization of Diesel Fuels by FeCl3/Ionic Liquids Chin. Chem. Lett. 2013, 24, 755 10.1016/j.cclet.2013.04.031
3. Shu, C. H.; Sun, T. H.; Zhang, H. B.; Jia, J. P.; Lou, Z. Y. A Novel Process for Gasoline Desulfurization Based on Extraction with Ionic Liquids and Reduction by Sodium Borohydride Fuel 2014, 121, 72 10.1016/j.fuel.2013.12.037
4. Julião, D.; Gomes, A. C.; Pillinger, M.; Cunha-Silva, L.; de Castro, B.; Gonçalves, I. S.; Balula, S. S. Desulfurization of Model Diesel by Extraction/Oxidation Using a Zinc-Substituted Polyoxometalate as Catalyst under Homogeneous and Heterogeneous (Mil-101(Cr) Encapsulated) Conditions Fuel Process. Technol. 2015, 131, 78 10.1016/j.fuproc.2014.10.030
5. Jiang, W.; Zhu, W. S.; Chang, Y. H.; Chao, Y. H.; Yin, S.; Liu, H.; Zhu, F. X.; Li, H. M. Ionic Liquid Extraction and Catalytic Oxidative Desulfurization of Fuels Using Dialkylpiperidinium Tetrachloroferrates Catalysts Chem. Eng. J. 2014, 250, 48 10.1016/j.cej.2014.03.074
6. Rodríguez-Cabo, B.; Rodríguez, H.; Rodil, E.; Arce, A.; Soto, A. Extractive and Oxidative-Extractive Desulfurization of Fuels with Ionic Liquids Fuel 2014, 117, 882 10.1016/j.fuel.2013.10.012
7. Chen, X.; Yuan, S.; Abdeltawab, A. A.; Al-Deyab, S. S.; Zhang, J.; Yu, L.; Yu, G. Extractive Desulfurization and Denitrogenation of Fuels Using Functional Acidic Ionic Liquids Sep. Purif. Technol. 2014, 133, 187 10.1016/j.seppur.2014.06.031
8. Song, Z.; Zhou, T.; Zhang, J. N.; Cheng, H. Y.; Chen, L. F.; Qi, Z. W. Screening of Ionic Liquids for Solvent-Sensitive Extraction-with Deep Desulfurization as an Example Chem. Eng. Sci. 2015, 129, 69 10.1016/j.ces.2015.02.023
9. Lissner, E.; de Souza, W. F.; Ferrera, B.; Dupont, J. Oxidative Desulfurization of Fuels with Task-Specific Ionic Liquids ChemSusChem 2009, 2, 962 10.1002/cssc.200900171
10. Nie, Y.; Dong, Y. X.; Bai, L.; Dong, H. F.; Zhang, X. P. Fast Oxidative Desulfurization of Fuel Oil Using Dialkylpyridinium Tetrachloroferrates Ionic Liquids Fuel 2013, 103, 997 10.1016/j.fuel.2012.07.071
11. Liang, W. D.; Zhang, S.; Li, H. F.; Zhang, G. D. Oxidative Desulfurization of Simulated Gasoline Catalyzed by Acetic Acid-Based Ionic Liquids at Room Temperature Fuel Process. Technol. 2013, 109, 27 10.1016/j.fuproc.2012.09.034
12. Gu, Y. Multicomponent Reactions in Unconventional Solvents: State of the Art Green Chem. 2012, 14, 2091 10.1039/c2gc35635j
13. Ren, S. H.; Hou, Y. C.; Wu, W. Z.; Chen, X. T.; Fan, J. L.; Zhang, J. W. Effect of H2O on the Desulfurization of Simulated Flue Gas by an Ionic Liquid Ind. Eng. Chem. Res. 2009, 48, 4928 10.1021/ie9000844
14. Francisco, M.; Arce, A.; Soto, A. Ionic Liquids on Desulfurization of Fuel Oils Fluid Phase Equilib. 2010, 294, 39 10.1016/j.fluid.2009.12.020
15. Abbott, A. P.; Capper, G.; Davies, D. L.; Rasheed, R. K.; Tambyrajah, V. Novel Solvent Properties of Choline Chloride/Urea Mixtures Chem. Commun. 2003, 70 10.1039/b210714g
16. Abbott, A. P.; Boothby, D.; Capper, G.; Davies, D. L.; Rasheed, R. K. Deep Eutectic Solvents Formed between Choline Chloride and Carboxylic Acids: Versatile Alternatives to Ionic Liquids J. Am. Chem. Soc. 2004, 126, 9142 10.1021/ja048266j
17. Cooper, E. R.; Andrews, C. D.; Wheatley, 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 10.1038/nature02860
18. Jhong, H. R.; Wong, D. S. H.; Wan, C. C.; Wang, Y. Y.; Wei, T. C. A Novel Deep Eutectic Solvent-Based Ionic Liquid Used as Electrolyte for Dye-Sensitized Solar Cells Electrochem. Commun. 2009, 11, 209 10.1016/j.elecom.2008.11.001
19. Shahbaz, K.; Mjalli, F. S.; Hashim, M. A.; AlNashef, I. M. Using Deep Eutectic Solvents Based on Methyl Triphenyl Phosphunium Bromide for the Removal of Glycerol from Palm-Oil-Based Biodiesel Energy Fuels 2011, 25, 2671 10.1021/ef2004943
20. Lindberg, D.; de la Fuente Revenga, M.; Widersten, M. Deep Eutectic Solvents (DESs) Are Viable Cosolvents for Enzyme-Catalyzed Epoxide Hydrolysis J. Biotechnol. 2010, 147, 169 10.1016/j.jbiotec.2010.04.011
21. Abbott, A. P.; Cullis, P. M.; Gibson, M. J.; Harris, R. C.; Raven, E. Extraction of Glycerol from Biodiesel into a Eutectic Based Ionic Liquid Green Chem. 2007, 9, 868 10.1039/b702833d
22. Guo, W. J.; Hou, Y. C.; Wu, W. Z.; Ren, S. H.; Tian, S. D.; Marsh, K. N. Separation of Phenol from Model Oils with Quaternary Ammonium Salts Via Forming Deep Eutectic Solvents Green Chem. 2013, 15, 226 10.1039/C2GC36602A
23. Shahbaz, K.; Mjalli, F. S.; Hashim, M. A.; AlNashef, I. M. Eutectic Solvents for the Removal of Residual Palm Oil-Based Biodiesel Catalyst Sep. Purif. Technol. 2011, 81, 216 10.1016/j.seppur.2011.07.032
24. Hizaddin, H. F.; Hadj-Kali, M. K.; Ramalingam, A.; Ali Hashim, M. Extractive Denitrogenation of Diesel Fuel Using Ammonium-and Phosphonium-Based Deep Eutectic Solvents J. Chem. Thermodyn. 2016, 95, 164 10.1016/j.jct.2015.12.009
25. Hizaddin, H. F.; Hadj-Kali, M. K.; Ramalingam, A.; Hashim, M. A. Extraction of Nitrogen Compounds from Diesel Fuel Using Imidazolium-and Pyridinium-Based Ionic Liquids: Experiments, Cosmo-RS Prediction and NRTL Correlation Fluid Phase Equilib. 2015, 405, 55 10.1016/j.fluid.2015.07.021
26. Hizaddin, H. F.; Ramalingam, A.; Hashim, M. A.; Hadj-Kali, M. K. O. Evaluating the Performance of Deep Eutectic Solvents for Use in Extractive Denitrification of Liquid Fuels by the Conductor-Like Screening Model for Real Solvents J. Chem. Eng. Data 2014, 59, 3470 10.1021/je5004302
27. Othmer, D. F.; Tobias, P. E. Liquid-Liquid Extraction Data-Toluene and Acetaldehyde Systems Ind. Eng. Chem. 1942, 34, 690 10.1021/ie50390a011
28. Hand, D. B. Dineric Distribution J. Phys. Chem. 1929, 34, 1961 10.1021/j150315a009
29. Wang, J.-L.; Zhao, D.-S.; Zhou, E.-P.; Dong, Z. Desulfurization of Gasoline by Extraction with n-Alkyl-Pyridinium-Based Ionic Liquids J. Fuel Chem. Technol. 2007, 35, 293 10.1016/S1872-5813(07)60022-X
30. Alonso, L.; Arce, A.; Francisco, M.; Rodríguez, O.; Soto, A. Gasoline Desulfurization Using Extraction with [C8mim][BF4] Ionic Liquid AIChE J. 2007, 53, 3108 10.1002/aic.11337
31. Alonso, L.; Arce, A.; Francisco, M.; Soto, A. Thiophene Separation from Aliphatic Hydrocarbons Using the 1-Ethyl-3-Methylimidazolium Ethylsulfate Ionic Liquid Fluid Phase Equilib. 2008, 270, 97 10.1016/j.fluid.2008.06.012
32. Klamt, A. Conductor-Like Screening Model for Real Solvents: A New Approach to the Quantitative Calculation of Solvation Phenomena J. Phys. Chem. 1995, 99, 2224 10.1021/j100007a062
33. Klamt, A.; Eckert, F. Cosmo-RS: A Novel and Efficient Method for the A Priori Prediction of Thermophysical Data of Liquids Fluid Phase Equilib. 2000, 172, 43 10.1016/S0378-3812(00)00357-5
34. Hizaddin, H. F.; Sarwono, M.; Hashim, M. A.; Alnashef, I. M.; Hadj-Kali, M. K. 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 10.1016/j.jct.2014.12.024
35. 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 10.1039/c4ra01081g
36. Turbomole: Program Package for ab initio Electronic Structure Calculations; Users' Manual, Version 6.4; Turbomole GmbH: Karlsruhe, Germany, 2012.
37. A Graphical User Interface to the COSMOtherm Program. User Guide; COSMOthermX: Leverkusen, Germany, 2013.
38. Simulis Thermodynamics: Mixtures Properties and Fluid Phases Equilibria Calculations; Prosim: Labége, France. Available via the Internet at: http://www.prosim.net/.
39. Renon, H.; Prausnitz, J. M. Local Compositions in Thermodynamic Excess Functions for Liquid Mixtures AIChE J. 1968, 14, 135 10.1002/aic.690140124