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Deepening of the Role of Cation Substituents on the Extractive Ability of Pyridinium Ionic Liquids of N-Compounds from Fuels

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§ Organic Chemistry Department, Faculty of Chemistry, University of Vigo, Campus Lagoas Marcosende, 36210 Vigo, Pontevedra, Spain
† Departamento de Ingeniería Química Industrial y del Medio Ambiente, Universidad Politécnica de Madrid, Calle de José Gutiérrez Abascal 2, 28006 Madrid, Spain
‡ Departamento de Química Física aplicada, Universidad Autónoma de Madrid, Campus de Cantoblanco, C/Francisco Tomás y Valiente 7, 28049 Madrid, Spain
*Phone: +34 986812290. E-mail: [email protected]
Cite this: ACS Sustainable Chem. Eng. 2017, 5, 2, 2015–2025
Publication Date (Web):January 12, 2017
https://doi.org/10.1021/acssuschemeng.6b02922
Copyright © 2017 American Chemical Society
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    Abstract

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    New functionalized 1-butyl-3-Xpyridinium dicyanamide ionic liquids (ILs) were synthesized by adding groups (X = cyano, amino, chlorine, alkyl) with different substituent effects. Experimental and computational analyses were performed to evaluate the role of the pyridinium substituent on IL solvent properties, particularly as an extracting agent of pyridine from fuels. Quantum chemical calculations and NMR measurements indicated that the hydrogen bond (HB) donor character of the cation was successfully tuned by an adequate substitution. The COSMO-RS study showed that pyridine produces exothermic mixtures with these ILs, mainly due to favorable HB interactions. However, the mixture behavior was found to be controlled by entropy. Experimental and calculated Liquid–Liquid Equilibrium (LLE) data of pyridine-heptane-IL mixtures revealed that the new functionalized ILs present favorable partition coefficients and selectivity for extracting N-compounds from aliphatic mixtures. It was possible to enhance the solvent performance by using tetraalkyl substituents, which increases the entropy of the system.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acssuschemeng.6b02922.

    • Detailed experimental synthesis and characterization data of the synthesized ILs; figures with the σ-profiles and σ-potentials of cations and anions obtained by COSMO-RS; triangular diagrams with the experimental tie-lines for the ternary mixtures {heptane (1) + pyridine (2) + IL (3)}; table with the calculated parameters resonance effect (σR+), inductive field effect (σF)e, and polarizability effect (σα) for the studied cations; and table with the interpolation of β (solute distribution ratio) and S (selectivity) values for the studied ILs at fixed pyridine composition (PDF)

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