Isobaric VLE data for the system of butan-1-ol + butyl ethanoate + 1-butyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide
Introduction
Extractive distillation is widely used to separate azeotropic or close-boiling mixtures, and the entrainer plays a significant role in the application of extractive distillation [1], [2], [3], [4], [5]. However, the conventional entrainers are usually volatile and they will cause environmental problem. Ionic liquids (ILs) are chemicals composed entirely of ions. They have excellent properties such as: nonvolatility, less causticity, and good performance in improving the separation efficiency [6], [7], [8]. Because of these merits, ILs have attracted increasing attentions in the separation process in the past ten years. Many authors studied the effects of ionic liquids to azeotropic mixtures or close boiling mixtures [9], [10], [11], [12], [13], [14], [15], [16]. The phase equilibria data are essential for separation processes, but the phase equilibria data for the IL-containing systems are still insufficient up to now.
A minimum-boiling azeotrope can be formed by butyl ethanoate and butan-1-ol, and an enhanced distillation (such as extractive distillation) can be used to separate the azeotrope [17], [18]. Recently, ionic liquids are often used as mass-separating agents for the azeotropic mixture due to their particular properties. Vapor–liquid equilibrium data are essential for the development of the new enhanced distillation process.
To find a suitable ionic liquid solvent for the separation of butan-1-ol and butyl ethanoate, we calculated the infinite dilution activity coefficients of butan-1-ol and butyl ethanoate in hundreds of ILs using COSMO-SAC model [19], [20]. We found 1-butyl-3-methylimidazolium bis[(trifluoromethyl) sulfonyl] imide ([BMIM][NTf2]) was a promising solvent for the separation of the azeotropic mixture butan-1-ol + butyl ethanoate. In this paper, vapor-liquid equilibrium data for the ternary system butan-1-ol + butyl ethanoate + [BMIM][NTf2] and binary system of butan-1-ol + [BMIM][NTf2] as well as butyl ethanoate + [BMIM][NTf2] are presented, and the vapor-liquid equilibrium (VLE) data were correlated by the nonrandom two-liquid (NRTL) model.
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Materials
The ionic liquid ([BMIM][NTf2]) was purchased from Chengjie Chemical Reagents Co., Shanghai, China, with a minimum mass fraction of 0.99 (observed by liquid chromatography). The water mass fraction in ionic liquid determined by Karl Fischer titration was less than 0.001. Butyl ethanoate and butan-1-ol were purchased from Jiangtian Chemical Reagents Co., Tianjin, China.
Their purities checked by gas chromatography were greater than 0.997 in mass fraction. All chemicals were used without further
Experimental data
Equilibria temperatures for the binary systems of butan-1-ol + [BMIM][NTf2] and butyl ethanoate + [BMIM][NTf2] were measured at 101.3 kPa and the results are shown in Table 1, Table 2, respectively. Where x3 presents the mole fraction of ionic liquid in the liquid phase, Texp presents the experimental equilibrium temperature and Tcal presents the calculated equilibrium temperature.
Vapor–liquid equilibrium for the ternary system of butan-1-ol (1) + butyl ethanoate (2) + [BMIM][NTf2] (3) was measured at
Conclusions
The vapor–liquid equilibrium for the ternary system of butan-1-ol + butyl ethanoate + [BMIM][NTf2] and the binary systems of butan-1-ol + [BMIM][NTf2] and butyl ethanoate + [BMIM][NTf2] were measured at 101.3 kPa. The NRTL model was used to correlate the VLE data for the ternary mixture, and the correlated results agreed well with the experimental results. The results indicate that the relative volatility of butan-1-ol to butyl ethanoate can be greatly enhanced by IL ([BMIM][NTf2]), and the azeotropic
Acknowledgments
The authors are grateful to the Innovation Fund of Tianjin University for the financial support of this work.
References (28)
- et al.
Effect of anion fluorination in 1-ethyl-3-methylimidazolium as solvent for the liquid extraction of ethanol from ethyl tert-butyl ether
Fluid Phase Equilibr.
(2006) - et al.
Purification of ethyl tert-butyl ether from its mixtures with ethanol by using an ionic liquid
Chem. Eng. J.
(2006) - et al.
Measurement and correlation of vapor-liquid equilibria and excess enthalpies of binary systems containing ionic liquids and hydrocarbons
Fluid Phase Equilib.
(2004) - et al.
Measurement and prediction of vapor-liquid equilibria of ternary systems containing ionic liquids
Fluid Phase Equilib.
(2005) - et al.
Efficient optimization-based design of distillation processes for homogeneous azeotropic mixtures
Ind. Eng. Chem. Res.
(2009) - et al.
Azeotropic distillation
AIChE J.
(1996) - et al.
Em Perry's Chemical Engineers’ Handbook. Distillation
(1997) - et al.
Distillation: Principles and Practice
(1998) - et al.
Conceptual Design of Distillation Systems
(2001) - et al.
Ionic liquids in separations
Acc. Chem. Res.
(2007)
Ionic liquids show promise for clean separation technology
Chem. Eng. News
Structure and solvation in ionic liquids
Acc. Chem. Res.
Separation of azeotropic mixtures using hyperbranched polymers or ionic liquids
AIChE J.
Extractive distillation with ionic fluids
Chem. Ing. Tech.
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