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Liquid–Liquid Equilibria of Ionic Liquids–Water–Acetic Acid Mixtures

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The QUILL Research Centre, School of Chemistry and Chemical Engineering, Queen’s University, Stranmillis Road, Belfast BT9 5AG, United Kingdom
Eastman Chemical Company, 100 N. Eastman Road, Kingsport, Tennessee 37662, United States
§ School of Chemical Engineering and Analytical Science, University of Manchester, The Mill, Sackville Street, Manchester M13 9PL United Kingdom
Cite this: J. Chem. Eng. Data 2017, 62, 2, 653–664
Publication Date (Web):January 11, 2017
https://doi.org/10.1021/acs.jced.6b00692
Copyright © 2017 American Chemical Society

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    Abstract

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    The liquid–liquid equilibria of ionic liquid-based systems with water and/or acetic acid have been studied at 293.15 K and atmospheric pressure. One hydrophilic ionic liquid and a series of hydrophobic ionic liquids were investigated in order to examine their effect on the separation of water and acetic acid mixtures. The ionic liquids studied were [P666,14]Cl, [P666,14][NTf2], [C4mmim][NTf2], [Cnmim][NTf2] (n = 2, 4, 6, 8, or 10), [C4mpyrr][NTf2], [N1114][NTf2], and [C2mim][EtSO4]. [C2mim][EtSO4] is totally miscible with water and acetic acid in all compositions. Comparing [P666,14]Cl with [P666,14][NTf2], the former showed higher extraction selectivities; however, due to the larger viscosity of [P666,14]Cl, the [NTf2] based ionic liquids offer a better solvent choice for the liquid extraction processes. As expected, as the solubility of water decreases with increasing the chain length of ionic liquids, this in turn leads to [C10mim][NTf2] showing greater acetic efficiency than [C2mim][NTf2] for the separation of water and acetic acid. The experimental data obtained for ternary systems containing the [C4mmim][NTf2] demonstrated that the modification of the C(2) position on the imidazolium ring does not significantly affect the selectivity compared with [C4mim][NTf2]. Tetraalkyl ammonium and N-alkyl pyrrolidinium based ionic liquids were also studied with the [NTf2] anion with the results for the system containing the [C4mpyrr][NTf2] demonstrating a higher selectivity for the separation of water and acetic acid than the other [NTf2] based systems studied. All experimental data were then correlated using the UNIQUAC model within an accuracy close to 1.6%. Finally, the ionic liquids were also compared with standard molecular extraction solvent, for example, methyl tert-butyl ether and methyl isobutyl ketone. The organic solvents showed an advantage over the [Cnmim][NTf2]-based ionic liquids but only over a narrow composition range. In all ionic liquid systems, the selectivity remains high at low acetic acid concentration compared with that found in the organic solvents, which is important for practical operation and demonstrates the advantages of using an ionic liquid for the extraction.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jced.6b00692.

    • 1H NMR spectra of the synthesized ionic liquids are reported in Figures S1–S9. Composition of the experimental tie-line ends, and values of the solute distribution ratios (βx and βw calculated from the mole and mass fractions, respectively) and selectivity (S) and equilibrium diagrams for each ternary system are reported in Tables S1–S12 and compared in Figures S10–S11. A comparison of the water solubility in each of the investigated hydrophobic ionic liquids is reported, herein, and comparisons with those available in the literature are reported in Table S13. Comparisons between experimental tie-line ends and those correlated with the UNIQUAC model are shown in Figures S12–S23. Finally, predictive capability of the UNIQUAC model was then shown in Figure S24 by comparing calculated data with experimental tie-line ends available in the literature in the case of the (water + acetic acid + [C4mim][NTf2]) ternary system at 298.15 K and atmospheric pressure (PDF)

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