Separation of benzene and cyclohexane azeotrope mixture using 1-ethyl-3-methylimidazolium ethyl sulfate ionic liquid using extractive distillation
DOI:
https://doi.org/10.69660/jmpt.v1i1.61Keywords:
Ionic liquids, Benzene, Cyclohexane, Extractive Distillation, COSMO-RSAbstract
Most of the cyclohexane used for various industrial applications is largely produced through catalytic hydrogenation of benzene and the separation of cyclohexane from the unreacted benzene is industrially significant. However, it is tough to separate cyclohexane from benzene by conventional distillation processes since these components have close boiling points and form an azeotrope mixture. Currently, extractive distillation is commercially used for the separation of cyclohexane from benzene using conventional solvents (entrainers) such as sulfolane, dimethyl sulfoxide, N-formylmorpholine, and N-methylpyrrolidone. However, separating benzene and cyclohexane with extractive distillation with these solvents makes the process complex and consumes high energy. On the other hand, ionic liquids are considered green and potentially environmentally friendly, hence have been attracting attention in replacing conventional solvents (entrainers) in extractive distillation because of their unique properties. In this work, 1-ethyl-3-methylimidazolium ethylsulfate ([EMIM][EtSO4]) was used for the separation of cyclohexane from benzene using extractive distillation. The performance of [EMIM][EtSO4] was evaluated by measuring the isothermal vapour-liquid equilibrium (VLE) for benzene, cyclohexane, and [EMIM][EtSO4] ternary mixture at 353.15 K. The isothermal VLE was measured using Head Space Gas Chromatography (HS-GC). Moreover, the VLE data was also predicted using COSMO-RS and compared with the experimental values. The addition of [EMIM][EtSO4] eliminated the azeotrope and increased the relative volatilities of benzene and cyclohexane resulting in their separation. The performance of [EMIM][EtSO4] on the benzene and cyclohexane system was compared with dimethyl sulfoxide. The current ionic liquid shows higher relative volatility compared to dimethyl sulfoxide showing this ionic liquid can be used for the separation of benzene and cyclohexane using extractive distillation.
References
J. Garcia Villaluenga, A. Tabe-Mohammadi, A review on the separation of benzene/cyclohexane mixtures by pervaporation processes, Journal of membrane science, 169 (2000) 159-174.
G. Gonfa, M.A. Bustam, T. Murugesan, Z. Man, M. Mutalib, Thiocyanate based task-specific ionic liquids for separation of benzene and cyclohexane, Chem. Eng, 32 (2013) 1939-1944.
G. Gonfa, M. Ismail, M.A. Bustam, Benzene and cyclohexane separation using 1-butyl-3-methylimidazolium thiocyanate, in: AIP Conference Proceedings, AIP Publishing, 2017.
G. Gonfa, M.A. Bustam, N. Muhammad, S. Ullah, Effect of task-specific thiocyanate based ionic liquids on relative volatility of cyclohexane and benzene azeotropic mixture, Journal of Molecular Liquids, 238 (2017) 208-214.
M. Ayuso, A. Cañada-Barcala, M. Larriba, P. Navarro, N. Delgado-Mellado, J. Garcia, F. Rodriguez, Enhanced separation of benzene and cyclohexane by homogeneous extractive distillation using ionic liquids as entrainers, Separation and Purification Technology, 240 (2020) 116583.
Y. Bai, J. Qian, Q. Zhao, Y. Xu, S. Ye, Compatibility of PTET-60/CA blends and separation performance of their membranes for benzene/cyclohexane mixture by pervaporation, Journal of Applied Polymer Science, 102 (2006) 2832-2838.
S.J. Lue, F.J. Wang, S.Y. Hsiaw, Pervaporation of benzene/cyclohexane mixtures using ion-exchange membrane containing copper ions, Journal of membrane science, 240 (2004) 149-158.
T.M. Letcher, G.G. Redhi, S.E. Radloff, U. Doma ska, Liquid- Liquid Equilibria of the Ternary Mixtures with Sulfolane at 303.15 K, J. Chem. Eng. Data, 41 (1996) 634-638.
F.M. Lee, Use of organic sulfones as the extractive distillation solvent for aromatics recovery, Industrial & Engineering Chemistry Process Design and Development, 25 (1986) 949-957.
F.M. Lee, D.M. Coombs, Two-liquid-phase extractive distillation for aromatics recovery, Industrial & Engineering Chemistry Research, 26 (1987) 564-573.
W. Yin, S. Ding, S. Xia, P. Ma, X. Huang, Z. Zhu, Cosolvent Selection for Benzene- Cyclohexane Separation in Extractive Distillation, Journal of Chemical & Engineering Data, 55 (2010) 3274-3277.
B. Richard, M.A. Bustam, G. Gonfa, Separation of benzene and cyclohexane with mixed solvent using extractive distillation, Applied Mechanics and Materials, 625 (2014) 578-581.
B.-K. Mohamad Azmi, A.H. Muhamad, G. Gonfa, Z. Man, Benzene and cyclohexane separation using 1-propanenitrile-3-butylimidazolium dicyanamide ionic liquid, Advanced Materials Research, 879 (2014) 58-62.
N. Muhammad, G. Gonfa, A. Rahim, P. Ahmad, F. Iqbal, F. Sharif, A.S. Khan, F.U. Khan, Z.U.L.H. Khan, F. Rehman, I.U. Rehman, Investigation of ionic liquids as a pretreatment solvent for extraction of collagen biopolymer from waste fish scales using COSMO-RS and experiment, Journal of Molecular Liquids, 232 (2017) 258-264.
S. Nasir Shah, L. Kallidanthiyil Chellappan, G. Gonfa, M.I.A. Mutalib, R.B.M. Pilus, M.A. Bustam, Extraction of naphthenic acid from highly acidic oil using phenolate based ionic liquids, Chemical Engineering Journal, 284 (2016) 487-493.
G. Gonfa, M. Bustam, T. Murugesan, Z. Man, M. Mutalib, COSMO-RS based screening ionic liquids for separation of benzene and cyclohexane, Int. J, 3 (2012) 244-249.
G.W. Meindersma, Extraction of aromatics from naphtha with ionic liquids, (2005).
J.D. Holbrey, W.M. Reichert, R.P. Swatloski, G.A. Broker, W.R. Pitner, K.R. Seddon, R.D. Rogers, Efficient, halide free synthesis of new, low-cost ionic liquids: 1, 3-dialkylimidazolium salts containing methyl-and ethyl-sulfate anions, Green Chemistry, 4 (2002) 407-413.
M.Z.M. Salleh, M.K. Hadj-Kali, I. Wazeer, E. Ali, M.A. Hashim, Extractive separation of benzene and cyclohexane using binary mixtures of ionic liquids, Journal of Molecular Liquids, 285 (2019) 716-726.
E. Graczová, P. Steltenpohl, Application of ionic liquids in extractive distillation of ethanol-water system, Chemical Engineering Transactions, 45 (2015) 1957-1962.
X. Yang, X. Zhang, H. Dong, G. Yue, J. Liu, (Liquid+ liquid) equilibria for (benzene+ cyclohexane+ dimethyl sulfoxide) system at T=(298.15 or 303.15) K: Experimental data and correlation, The Journal of Chemical Thermodynamics, 84 (2015) 14-17.
G. Gonfa, M.A. Bustam, A.M. Sharif, N. Mohamad, S. Ullah, Tuning ionic liquids for natural gas dehydration using COSMO-RS methodology, Journal of Natural Gas Science and Engineering, 27 (2015) 1141-1148.
J. Iqbal, N. Muhammad, A. Rahim, A.S. Khan, Z. Ullah, G. Gonfa, P. Ahmad, COSMO-RS predictions, hydrogen bond basicity values and experimental evaluation of amino acid-based ionic liquids for lignocellulosic biomass dissolution, Journal of Molecular Liquids, 273 (2019) 215-221.
G. Gonfa, N. Muhammad, M. Azmi Bustam, Probing the interactions between DNA nucleotides and biocompatible liquids: COSMO-RS and molecular simulation study, Separation and Purification Technology, 196 (2018) 237-243.
A.S. Khan, Z. Man, M.A. Bustam, G. Gonfa, F.K. Chong, Z. Ullah, A. Nasrullah, A. Sarwono, P. Ahmad, N. Muhammad, Effect of Structural Variations on the Thermophysical Properties of Protic Ionic Liquids: Insights from Experimental and Computational Studies, Journal of Chemical & Engineering Data, 62 (2017) 2993-3003.
R. Shahid, N. Muhammad, G. Gonfa, M.S. Toprak, M. Muhammed, Synthesis, COSMO-RS analysis and optical properties of surface modified ZnS quantum dots using ionic liquids, Journal of Physics and Chemistry of Solids, 85 (2015) 34-38.
T. Abbas, G. Gonfa, K.C. Lethesh, M.I.A. Mutalib, M.b. Abai, K.Y. Cheun, E. Khan, Mercury capture from natural gas by carbon supported ionic liquids: Synthesis, evaluation and molecular mechanism, Fuel, 177 (2016) 296-303.
G. Gonfa, M.A. Bustam, A.M. Shariff, Quantum-chemical-based quantitative structure-activity relationships for estimation of CO2 absorption/desorption capacities of amine-based absorbents, International Journal of Greenhouse Gas Control, 49 (2016) 372-378.
B. Kolb, L.S. Ettre, Static headspace-gas chromatography: theory and practice, in, LibreDigital, 2006, pp. 201-202.
A.D. Becke, Density-functional exchange-energy approximation with correct asymptotic behaviour, Physical review A, 38 (1988) 3098.
A. Schäfer, C. Huber, R. Ahlrichs, Fully optimized contracted Gaussian basis sets of triple zeta valence quality for atoms Li to Kr, The Journal of chemical physics, 100 (1994) 5829-5835.
M. Diedenhofen, A. Klamt, COSMO-RS as a tool for property prediction of IL mixtures—A review, Fluid Phase Equilibria, 294 (2010) 31-38.
K. Kurihara, M. Uchiyama, K. Kojima, Isothermal vapor-liquid equilibria for benzene+ cyclohexane+ 1-propanol and for three constituent binary systems, Journal of Chemical & Engineering Data, 42 (1997) 149-154.
