Purification of ethyl tert-butyl ether from its mixtures with ethanol by using an ionic liquid (original) (raw)
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The Journal of Chemical Thermodynamics, 2012
In this work, the ionic liquids 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, [EMim] [NTf 2 ], 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, [BMim][NTf 2 ], 1-butyl-3-methylpyridinium bis(trifluoromethylsulfonyl)imide, [BMpy][NTf 2 ], 1-butyl-3-methylpyridinium trifluoromethanesulfonate, [BMpy][TfO], have been investigated for their use as solvents in extraction processes for the ethanol removal from its azeotropic mixture with hexane. Therefore, the experimental determination of the liquid + liquid equilibrium for the ternary systems {hexane (1) + ethanol (2) + [EMim][NTf 2 ] (3)}, {hexane (1) + ethanol (2) + [BMim][NTf 2 ] (3)}, {hexane (1) + ethanol (2) + [BMpy][NTf 2 ] (3)} and {hexane (1) + ethanol (2) + [BMpy][TfO] (3)} was carried out at T = 298.15 K and atmospheric pressure. Classical parameters such as selectivity and solute distribution ratio, derived from the tie-line data, were calculated and afterwards, the structural influence of the ionic liquids on the extraction process was analyzed. Finally, the experimental LLE data were correlated by means of the NRTL and UNIQUAC models.
Fluid Phase Equilibria, 2004
Liquid-liquid equilibrium data are presented for mixtures of {1-hexyl-3-methylimidozolium(tetrafluoroborate or hexafluorophospate) + ethanol + (1-hexene or 1-heptene)} at T = 298.2 K. The data presented provides valuable insight into how variation of the anion of the environmentally friendly ionic liquid solvent can have a marked effect upon the separation power of ionic liquids. The sloping of the tie lines towards the ethanol vertex is observed for mixtures of {1-hexyl-3-methylimadozolium tetrafluoroborate + ethanol + (1-hexene or 1-heptene)}, whilst the reverse, i.e. sloping of the tie lines towards the ionic liquid vertex is observed for mixtures of {1-hexyl-3-methylimadozolium hexafluorophospate + ethanol + (1-hexene or 1-heptene)}. The tie line data have been correlated through the use of the NTRL model for statistical consistency. Selectivity values, derived from the tie line data, indicate that these two ionic liquids are suitable solvents for the liquid-liquid extraction of ethanol from olefins.
The Journal of Chemical Thermodynamics, 2018
The present work was focused on the study of two imidazolium-based ionic liquids (ILs) as solvents in liquid-liquid extraction of ethanol from aqueous mixtures. With this aim, the experimental liquid-liquid equilibria (LLE) data of water (1) + ethanol (2) + 1ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([emim][Tf 2 N]) (3) and water (1) + ethanol (2) + 1-hexyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([hmim][Tf N]) (4) systems were obtained at different temperatures: 283.2, 303.2, and 323.2 K, in order to check the influence of temperature. The results were correlated by non-random two-liquid (NRTL) and universal quasichemical (UNIQUAC) models with good concordance in both cases. Finally, the ability of the two ILs to act as solvents was studied by evaluating the coefficient distribution and the selectivity of ternary systems and compared with another IL from the literature.
Journal of Chemical & Engineering Data, 2019
For separation of the azeotrope isobutyl acetate and isobutyl alcohol, imidazolium-based ionic liquids 1-hexyl-3-methylimidazolium hexafluorophosphate [Hmim][PF 6 ] and 1-octyl-3-methylimidazolium hexafluorophosphate [Omim][PF 6 ] were applied as the extractants in the extraction process. The liquid−liquid equilibrium (LLE) data for the ternary systems isobutyl acetate + isobutyl alcohol + ([Hmim][PF 6 ]/[Omim][PF 6 ]) were determined at temperature of 298.15 and 308.15 K. To evaluate extraction performance of the ILs, the selectivity and distribution coefficient were calculated from the experimental data. The effect of the alkyl chain length of the cations and the temperature on the LLE for the systems were explored. In addition, the experimental LLE data were correlated by the NRTL model, and the binary interaction parameters of the NRTL model were optimized.
Ionic liquids as solvents to separate the azeotropic mixture hexane/ethanol
Fluid Phase Equilibria, 2013
In this work the imidazolium ionic liquids 1-hexyl-3-methylimidazolium trifluoromethanesulfonate, [HMim][TfO], 1-hexyl-3-methylimidazolium dicyanamide, [HMim][N(CN) 2 ], 1-hexyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, [HMim][NTf 2 ], and 1-methyl-3-propylimidazolium bis(trifluoromethylsulfonyl)imide, [PMim][NTf 2 ], were studied as solvents for the separation of ethanol from its azeotropic mixture with hexane. The liquid-liquid equilibrium (LLE) of the ternary systems {hexane + ethanol + [HMim][TfO], or [HMim][N(CN) 2 ], or [HMim][NTf 2 ], or [PMim][NTf 2 ]} was carried out at 298.15 K and atmospheric pressure. From the experimental LLE data, the solute distribution ratio and selectivity were calculated and the solvent capacity of the studied ionic liquids was compared with another ionic liquid from literature. Finally, the experimental LLE data were correlated using the NRTL and UNIQUAC thermodynamic models.
Extractive Distillation of Ethanol-Water Using Ionic Liquids as Entrainers
Proceedings of the 8th International conference on Research in Engineering, Science and Technology, 2018
In recent years, ionic liquids (ILs) have received considerable attention for their use in chemical industry and are considered to be an alternative to conventional entrainers in extractive distillation, because of their ability to selectively separate azeotropic/close boiling mixtures [1, 2]. In this work, an extractive distillation process was investigated, comparing the imidazoliumbased ionic liquids (1-ethyl-3-methylimidazolium acetate), [EMIM][OAc] and (1ethyl-3methylimidazolium dicyanamide), [EMIM][DCA] with ethylene glycol (EG) organic solvent for ethanol dehydration. These ionic liquids were proposed with the aim of obtaining a higher selectivity than EG traditional solvent. The thermodynamic behavior of the ethanol/water mixture in the presence of the solvent was studied using Simulis Thermodynamics software; ionic liquids were created as new components, with the required thermodynamic and physical property parameters. The experimental data for ethanol/water/ethylene glycol mixture were fitted with the nonrandomtwo-liquid (NRTL) activity coefficient model to determine the binary interaction parameters, while, binary interaction parameters for ionic liquids were obtained from the literature. The vapor liquid equilibrium (VLE) behavior of ethanol-water in the presence of [EMIM][DCA] showed that this ionic liquid enhances the relative volatility of ethanol and allows to eliminate the ethanol-water azeotrope. The main operating conditions of anhydrous ethanol production have been determined to achieve a high distillate purity of 99.9 mol% in ethanol. It has been found that the [EMIM] [DCA] ionic liquid is very effective for the separation of ethanol-water azeotropic system even at low concentrations and less energy consuming compared to the conventional benchmark solvent EG.
The Journal of Chemical Thermodynamics, 2012
(Liquid + liquid) equilibrium data for the ionic liquids 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, [EMim][NTf 2 ], 1-propyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, [PMim] [NTf 2 ], 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, [BMim][NTf 2 ], and 1-hexyl-3methylimidazolium bis(trifluoromethylsulfonyl)imide, [HMim][NTf 2 ], mixed with ethanol and heptane were studied at T = 298.15 K and atmospheric pressure. The ability of these ionic liquids as solvents for the extraction of ethanol from heptane was evaluated in terms of selectivity and solute distribution ratio. Moreover, density and refractive index values over the miscible region for the ternary mixtures were also measured at T = 313.15 K. Finally, the experimental data were correlated with the Non Random Two Liquids (NRTL) and UNIversal QUAsi Chemical (UNIQUAC) thermodynamic models, and an exhaustive comparison with available literature data of the studied systems was carried out.
Fluid Phase Equilibria, 2015
A B S T R A C T Ionic liquids are neoteric, environmentally friendly solvents (since they do not produce emissions) composed of large organic cations and relatively small inorganic anions. They have favorable physical properties, such as negligible volatility and wide range of liquid existence. Liquid-liquid equilibrium (LLE) data for systems including ionic liquids, although essential for the design, optimization and operation of separation processes, are still scarce. However, some recent studies have presented ternary LLE data involving several ionic liquids and organic compounds such as alkanes, alkenes, alkanols, water, ethers and aromatics. In this work, the ASOG model for the activity coefficient is used to predict LLE data for 15 binary and 09 ternary systems at 101.3 kPa and several temperatures; all the systems are formed by ionic liquids including the tetrafluoroborate anion plus alkanes, alkanols, water, ethers, esters and aromatics. New group interaction parameters were determined using a modified Simplex method, minimizing a composition-based objective function of experimental data obtained from literature. The results are satisfactory, with rms deviations of about 3%.
Fluid Phase Equilibria, 2012
Liquid-liquid equilibria (LLE) were determined for ternary systems {methyl tert-amyl ether (TAME) + methanol + 1-butyl-3-methylimidazolium tetrafluoroborate ([Bmim][BF 4 ])}, {TAME + ethanol + [Bmim][BF 4 ]}, {TAME + methanol + 1-ethyl-3-methylimidazolium ethylsulfate (EMISE)} and {TAME + ethanol + EMISE} at 298.15 K. Experiments were carried out at atmospheric pressure using stirred and thermo-regulated cells. The experimental data were correlated with the well-known non random two liquid (NRTL) and universal quasi chemical (UNIQUAC) activity coefficient models. In addition, the distribution coefficients and the selectivities of the ionic liquids of [Bmim][BF 4 ] and EMISE for methanol and ethanol in the TAME phase were measured.
Fluid Phase Equilibria, 2013
In this work, the ionic liquids 1-butyl-1-methylpyrrolidinium dicyanamide, [BMpyr][N(CN) 2 ], and 1butyl-1-methylpyrrolidinium trifluoromethanesulfonate, [BMpyr][TfO], were studied as green solvents for the separation of ethanol from heptane and hexane. Liquid-liquid equilibrium (LLE) studies are important in the development of theoretical/semiempirical models for use in the design of extraction processes. Experimental liquid-liquid equilibrium (LLE) data were measured for the ternary systems {heptane or hexane (1) + ethanol (2) + [BMpyr][N(CN) 2 ] (3)} and {heptane or hexane (1) + ethanol (2) + [BMpyr][TfO] (3)} at 298.15 K and atmospheric pressure. The effectiveness of the extraction of ethanol from the alkanes was evaluated by solute distribution ratio and selectivity values. Finally, the experimental tie-line data were accurately correlated with the non-random two liquid (NRTL) thermodynamic model.