Aliphatic–Aromatic Separation Using Deep Eutectic Solvents as Extracting Agents

The separation of aliphatic and aromatic compounds is a great challenge for chemical engineers. There is no efficient separation process for mixtures with compositions lower than 20 wt % in aromatics. In this work, the feasibility of two different deep eutectic solvents (DESs) as novel extracting agents for the separation of the mixture {hexane + benzene} were tested. In order to select the proper solvent for this separation, a solubility test of a set of DESs was done at room temperature and atmospheric pressure. The selected deep eutectic solvents for this work were (i) tetrahexylammonium bromide:ethylene glycol with molar ratio = 1:2 (DES 1) and (ii) tetrahexylammonium bromide:glycerol with molar ratio = 1:2 (DES 2). The selected DESs were characterized by measurement of density and viscosity at atmospheric pressure and temperatures T = 293.2–343.2 K. Next, the liquid–liquid equilibria (LLE) of the ternary systems {hexane + benzene + DES 1} and {hexane + benzene + DES 2} were determined at T/K = 298.2 ...

[1]  Á. Domínguez,et al.  Separation of benzene from alkanes by solvent extraction with 1-ethylpyridinium ethylsulfate ionic liquid , 2010 .

[2]  H. Kim,et al.  Ionic Liquids as Benign Solvents for the Extraction of Aromatics , 2012 .

[3]  Mohd Ali Hashim,et al.  Phase equilibria of toluene/heptane with tetrabutylphosphonium bromide based deep eutectic solvents for the potential use in the separation of aromatics from naphtha , 2012 .

[4]  David L Davies,et al.  Novel solvent properties of choline chloride/urea mixtures. , 2003, Chemical communications.

[5]  Geert-Jan Witkamp,et al.  Natural deep eutectic solvents as new potential media for green technology. , 2013, Analytica chimica acta.

[6]  J. Canosa,et al.  Separation of Benzene from Hexane Using 3-butyl-1-methylimidazolium Bis(trifluoromethylsulfonyl)imide as Entrainer: Liquid-Liquid Equilibrium Data, Process Simulation and Process Separation in a Packed Bed Column , 2012 .

[7]  François Jérôme,et al.  Deep eutectic solvents: syntheses, properties and applications. , 2012, Chemical Society reviews.

[8]  F. Mjalli,et al.  Liquid–liquid equilibria for the ternary system (phosphonium based deep eutectic solvent–benzene–hexane) at different temperatures: A new solvent introduced , 2012 .

[9]  K. R. Seddon,et al.  Bis{(trifluoromethyl)sulfonyl}amide ionic liquids as solvents for the extraction of aromatic hydrocarbons from their mixtures with alkanes: effect of the nature of the cation , 2009 .

[10]  Á. Domínguez,et al.  Liquid extraction of aromatic/cyclic aliphatic hydrocarbon mixtures using ionic liquids as solvent: Literature review and new experimental LLE data , 2014 .

[11]  K. R. Seddon,et al.  Separation of benzene and hexane by solvent extraction with 1-alkyl-3-methylimidazolium bis{(trifluoromethyl)sulfonyl}amide ionic liquids: effect of the alkyl-substituent length. , 2007, The journal of physical chemistry. B.

[12]  Á. Domínguez,et al.  (Liquid + liquid) equilibria for ternary mixtures of (alkane + benzene + [EMpy] [ESO4]) at several temperatures and atmospheric pressure , 2009 .

[13]  K. R. Seddon,et al.  1 -Ethyl-3-methylimidazolium bis{(trifluoromethyl)sulfonyl}amide as solvent for the separation of aromatic and aliphatic hydrocarbons by liquid extraction : extension to C7-and C8-fractions , 2008 .

[14]  G. W. Meindersma,et al.  SEPARATION OF AROMATIC AND ALIPHATIC HYDROCARBONS WITH IONIC LIQUIDS , 2004 .

[15]  U. Domańska,et al.  Separation of aromatic hydrocarbons from alkanes using ammonium ionic liquid C2NTf2 at T = 298.15 K , 2007 .

[16]  B. S. Rawat,et al.  Liquid-liquid equilibrium studies for separation of aromatics , 2007 .

[17]  G. W. Meindersma,et al.  Cyano-containing ionic liquids for the extraction of aromatic hydrocarbons from an aromatic/aliphatic mixture , 2012, Science China Chemistry.

[18]  Liquid–liquid equilibrium data for the systems {LTTM + benzene + hexane} and {LTTM + ethyl acetate + hexane} at different temperatures and atmospheric pressure , 2013 .

[19]  M. C. Kroon,et al.  Low-transition-temperature mixtures (LTTMs): a new generation of designer solvents. , 2013, Angewandte Chemie.

[20]  Jianguo Mi,et al.  Liquid–liquid equilibria of multi-component systems including n-hexane, n-octane, benzene, toluene, xylene and sulfolane at 298.15 K and atmospheric pressure , 2000 .

[21]  A. Kaul The Phase Diagram , 2000 .

[22]  P. Rasmussen,et al.  Liquid-liquid equilibrium data: Their retrieval, correlation and prediction Part I: Retrieval , 1979 .

[23]  G. W. Meindersma,et al.  Conceptual process design for aromatic/aliphatic separation with ionic liquids , 2008 .

[24]  B. Mokhtarani,et al.  Ternary (liquid–liquid) equilibria of nitrate based ionic liquid + alkane + benzene at 298.15 K: Experiments and correlation , 2013 .

[25]  M. Fahim,et al.  Prediction and measurement of phase equilibria for the extraction of BTX from naphtha reformate using BMIMPF6 ionic liquid , 2014 .

[26]  G. W. Meindersma,et al.  Ternary liquid-liquid equilibria for mixtures of toluene + n-heptane + an ionic liquid , 2006 .

[27]  J. Prausnitz,et al.  LOCAL COMPOSITIONS IN THERMODYNAMIC EXCESS FUNCTIONS FOR LIQUID MIXTURES , 1968 .

[28]  K. Mohanty,et al.  Liquid–liquid equilibria studies on ammonium and phosphonium based ionic liquid–aromatic–aliphatic component at T = 298.15 K and p = 1 bar: Correlations and a-priori predictions , 2013 .

[29]  J. Torrecilla,et al.  Liquid–liquid equilibria for {hexane+benzene+1-ethyl-3-methylimidazolium ethylsulfate} at (298.2, 313.2 and 328.2)K , 2009 .