Imidazolium and pyridinium-based ionic liquids for the cyclohexane/cyclohexene separation by liquid-liquid extraction

abstract

The separation of olefins/paraffins is a challenge for the petrochemical industry due to the close boiling points of these hydrocarbons. In this work we have studied the feasibility of different imidazolium and pyridinium-based ionic liquids (ILs) as alternative solvents in the cyclohexane/cyclohexene separation. Five ILs have been studied, namely 1-butyl-4-methylpyridinium tricyanomethanide ([4bmpy][TCM]), bis(1-ethyl-3-methylimidazolium) tetrathiocyanatocobaltate ([emim](2)[Co(SCN)(4)]), bis(1-butyl-3-methylimidazolium) tetrathiocyanatocobaltate ([bmim](2)[Co(SCN)(4)]), 1-ethyl-4-methylpyridinium bis(trifluoromethylsulfonyl)imide ([4empy][Tf2N]), and 1-butyl-4-methylpyridinium bis(trifluoromethylsulfonyl)imide ([4bmpy][Tf2N]). Experimental liquid-liquid equilibrium (LLE) data were obtained for the equimolar ternary mixtures {cyclohexane (1) + cyclohexene (2) + IL (3)} at T = (298.2, 313.2 and 328.2) K and atmospheric pressure in order to study the effect of the temperature on the extractive properties. Afterwards, LLE data for every ternary system was determined at the best temperature and for the whole cyclohexane/cyclohexene composition range. These ILs have shown promising results in terms of distribution ratio and selectivity, showing the [4bmpy][TCM] IL the best extractive properties at 298.2 K and atmospheric pressure. The Non-Random Two Liquids (NRTL) model was used to successfully correlate the experimental LLE data. (C) 2018 Elsevier Ltd.

keywords

BINARY-MIXTURES HEXANE/HEX-1-ENE; ACTIVITY-COEFFICIENTS; INFINITE DILUTION; ORGANIC SOLUTES; PHYSICOCHEMICAL PROPERTIES; ALIPHATIC-HYDROCARBONS; SOLVENT-EXTRACTION; WATER; CYCLOHEXENE; BENZENE

subject category

Thermodynamics; Chemistry

authors

Delgado-Mellado, N; Ovejero-Perez, A; Navarro, P; Larriba, M; Ayuso, M; Garcia, J; Rodriguez, F

our authors

acknowledgements

The authors are grateful to Ministerio de Economia y Competitividad (MINECO) of Spain and Comunidad Autonoma de Madrid for the financial support of Projects CTQ2017-85340-R and S2013/MAE-2800, respectively. N.D.M. thanks MINECO for her FPI grant (Reference BES-2015-072855). P.N. also thanks Fundacao para a Ciencia e a Tecnologia for awarding him a postdoctoral grant (Reference SFRH/BPD/117084/2016).

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