Solutions of ionic liquids with diverse aliphatic and aromatic solutes – Phase behavior and potentials for applications: A review article

Zoran P. Visak*, Marta S. Calado, Jelena M. Vuksanovic, Gorica R. Ivanis, Adriana S.H. Branco, Nikola D. Grozdanic, Mirjana Lj Kijevcanin, Slobodan P. Serbanovic

*Corresponding author for this work

Research output: Contribution to journalReview article

Abstract

This article principally reviews our research related to liquid–liquid and solid–liquid phase behavior of imidazolium- and phosphonium-based ionic liquids, mainly having bistriflamide ([NTf2]) or triflate ([OTf]) anions, with several aliphatic and aromatic solutes (target molecules). The latter include: (i) diols and triols: 1,2-propanediol, 1,3-propanediol and glycerol; (ii) polymer poly(ethylene glycol) (PEG): average molecular mass 200, 400 and 2050 – PEG200 (liquid), PEG400 (liquid) and PEG2050 (solid), respectively; (iii) polar aromatic compounds: nicotine, aniline, phenolic acids (vanillic, ferulic and caffeic acid,), thymol and caffeine and (iv) non-polar aromatic compounds (benzene, toluene, p-xylene). In these studies, the effects of the cation and anion, cation alkyl chain and PEG chain lengths on the observed phase behaviors were scrutinized. Thus, one of the major observations is that the anion – bistriflamide/triflate – selection usually had strong, sometimes really remarkable effects on the solvent abilities of the studied ionic liquids. Namely, in the case of the hydrogen-bonding solutes, the ionic liquids with the triflate anion generally exhibited substantially higher solubility than those having the bistriflamide anion. Nevertheless, with the aromatic compounds the situation was the opposite – in most of the cases it was the bistriflamide anion that favoured solubility. Moreover, our other studies confirmed the ability of PEG to dissolve both polar and non-polar aromatic compounds. Therefore, two general possibilities of application of alternative, environmentally acceptable, solvents of tuneable solvent properties appeared. One is to use homogeneous mixtures of two ionic liquids having [NTf2] and [OTf] anions as mixed solvents. The other, however, envisages the application of homogeneous and heterogeneous (PEG + ionic liquid) solutions as tuneable solvents for aromatic solutes. Such mixed solvents have potential applications in separation of the aforesaid target molecules from their aqueous solutions or in extraction from original matrices. From the fundamental point of view the phase equilibrium studies reviewed herein and the diversity of the pure compounds – ionic liquids and target molecules – represent a good base for the discussion of interactions between the molecules that exist in the studied solutions.

Original languageEnglish
Pages (from-to)1628-1640
Number of pages13
JournalArabian Journal of Chemistry
Volume12
Issue number7
Early online date13 Oct 2014
DOIs
Publication statusPublished - Nov 2019

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Ionic Liquids
Phase behavior
Ionic liquids
Anions
Negative ions
Aromatic compounds
Polyethylene glycols
Polymers
Molecules
Cations
Solubility
Positive ions
Nicotine
Thymol
Caffeine
Propylene Glycol
Acids
Toluene
Liquids
Molecular mass

Bibliographical note

© 2014 Production and hosting by Elsevier B.V. on behalf of King Saud University.This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/3.0/).

Keywords

  • High-value compounds
  • Ionic liquids
  • Phase equilibria
  • Poly(ethylene glycol)
  • Sustainable solvents

Cite this

Visak, Z. P., Calado, M. S., Vuksanovic, J. M., Ivanis, G. R., Branco, A. S. H., Grozdanic, N. D., ... Serbanovic, S. P. (2019). Solutions of ionic liquids with diverse aliphatic and aromatic solutes – Phase behavior and potentials for applications: A review article. Arabian Journal of Chemistry, 12(7), 1628-1640. https://doi.org/10.1016/j.arabjc.2014.10.003
Visak, Zoran P. ; Calado, Marta S. ; Vuksanovic, Jelena M. ; Ivanis, Gorica R. ; Branco, Adriana S.H. ; Grozdanic, Nikola D. ; Kijevcanin, Mirjana Lj ; Serbanovic, Slobodan P. / Solutions of ionic liquids with diverse aliphatic and aromatic solutes – Phase behavior and potentials for applications : A review article. In: Arabian Journal of Chemistry. 2019 ; Vol. 12, No. 7. pp. 1628-1640.
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abstract = "This article principally reviews our research related to liquid–liquid and solid–liquid phase behavior of imidazolium- and phosphonium-based ionic liquids, mainly having bistriflamide ([NTf2]−) or triflate ([OTf]−) anions, with several aliphatic and aromatic solutes (target molecules). The latter include: (i) diols and triols: 1,2-propanediol, 1,3-propanediol and glycerol; (ii) polymer poly(ethylene glycol) (PEG): average molecular mass 200, 400 and 2050 – PEG200 (liquid), PEG400 (liquid) and PEG2050 (solid), respectively; (iii) polar aromatic compounds: nicotine, aniline, phenolic acids (vanillic, ferulic and caffeic acid,), thymol and caffeine and (iv) non-polar aromatic compounds (benzene, toluene, p-xylene). In these studies, the effects of the cation and anion, cation alkyl chain and PEG chain lengths on the observed phase behaviors were scrutinized. Thus, one of the major observations is that the anion – bistriflamide/triflate – selection usually had strong, sometimes really remarkable effects on the solvent abilities of the studied ionic liquids. Namely, in the case of the hydrogen-bonding solutes, the ionic liquids with the triflate anion generally exhibited substantially higher solubility than those having the bistriflamide anion. Nevertheless, with the aromatic compounds the situation was the opposite – in most of the cases it was the bistriflamide anion that favoured solubility. Moreover, our other studies confirmed the ability of PEG to dissolve both polar and non-polar aromatic compounds. Therefore, two general possibilities of application of alternative, environmentally acceptable, solvents of tuneable solvent properties appeared. One is to use homogeneous mixtures of two ionic liquids having [NTf2]− and [OTf]− anions as mixed solvents. The other, however, envisages the application of homogeneous and heterogeneous (PEG + ionic liquid) solutions as tuneable solvents for aromatic solutes. Such mixed solvents have potential applications in separation of the aforesaid target molecules from their aqueous solutions or in extraction from original matrices. From the fundamental point of view the phase equilibrium studies reviewed herein and the diversity of the pure compounds – ionic liquids and target molecules – represent a good base for the discussion of interactions between the molecules that exist in the studied solutions.",
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Visak, ZP, Calado, MS, Vuksanovic, JM, Ivanis, GR, Branco, ASH, Grozdanic, ND, Kijevcanin, ML & Serbanovic, SP 2019, 'Solutions of ionic liquids with diverse aliphatic and aromatic solutes – Phase behavior and potentials for applications: A review article', Arabian Journal of Chemistry, vol. 12, no. 7, pp. 1628-1640. https://doi.org/10.1016/j.arabjc.2014.10.003

Solutions of ionic liquids with diverse aliphatic and aromatic solutes – Phase behavior and potentials for applications : A review article. / Visak, Zoran P.; Calado, Marta S.; Vuksanovic, Jelena M.; Ivanis, Gorica R.; Branco, Adriana S.H.; Grozdanic, Nikola D.; Kijevcanin, Mirjana Lj; Serbanovic, Slobodan P.

In: Arabian Journal of Chemistry, Vol. 12, No. 7, 11.2019, p. 1628-1640.

Research output: Contribution to journalReview article

TY - JOUR

T1 - Solutions of ionic liquids with diverse aliphatic and aromatic solutes – Phase behavior and potentials for applications

T2 - A review article

AU - Visak, Zoran P.

AU - Calado, Marta S.

AU - Vuksanovic, Jelena M.

AU - Ivanis, Gorica R.

AU - Branco, Adriana S.H.

AU - Grozdanic, Nikola D.

AU - Kijevcanin, Mirjana Lj

AU - Serbanovic, Slobodan P.

N1 - © 2014 Production and hosting by Elsevier B.V. on behalf of King Saud University.This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/3.0/).

PY - 2019/11

Y1 - 2019/11

N2 - This article principally reviews our research related to liquid–liquid and solid–liquid phase behavior of imidazolium- and phosphonium-based ionic liquids, mainly having bistriflamide ([NTf2]−) or triflate ([OTf]−) anions, with several aliphatic and aromatic solutes (target molecules). The latter include: (i) diols and triols: 1,2-propanediol, 1,3-propanediol and glycerol; (ii) polymer poly(ethylene glycol) (PEG): average molecular mass 200, 400 and 2050 – PEG200 (liquid), PEG400 (liquid) and PEG2050 (solid), respectively; (iii) polar aromatic compounds: nicotine, aniline, phenolic acids (vanillic, ferulic and caffeic acid,), thymol and caffeine and (iv) non-polar aromatic compounds (benzene, toluene, p-xylene). In these studies, the effects of the cation and anion, cation alkyl chain and PEG chain lengths on the observed phase behaviors were scrutinized. Thus, one of the major observations is that the anion – bistriflamide/triflate – selection usually had strong, sometimes really remarkable effects on the solvent abilities of the studied ionic liquids. Namely, in the case of the hydrogen-bonding solutes, the ionic liquids with the triflate anion generally exhibited substantially higher solubility than those having the bistriflamide anion. Nevertheless, with the aromatic compounds the situation was the opposite – in most of the cases it was the bistriflamide anion that favoured solubility. Moreover, our other studies confirmed the ability of PEG to dissolve both polar and non-polar aromatic compounds. Therefore, two general possibilities of application of alternative, environmentally acceptable, solvents of tuneable solvent properties appeared. One is to use homogeneous mixtures of two ionic liquids having [NTf2]− and [OTf]− anions as mixed solvents. The other, however, envisages the application of homogeneous and heterogeneous (PEG + ionic liquid) solutions as tuneable solvents for aromatic solutes. Such mixed solvents have potential applications in separation of the aforesaid target molecules from their aqueous solutions or in extraction from original matrices. From the fundamental point of view the phase equilibrium studies reviewed herein and the diversity of the pure compounds – ionic liquids and target molecules – represent a good base for the discussion of interactions between the molecules that exist in the studied solutions.

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Visak ZP, Calado MS, Vuksanovic JM, Ivanis GR, Branco ASH, Grozdanic ND et al. Solutions of ionic liquids with diverse aliphatic and aromatic solutes – Phase behavior and potentials for applications: A review article. Arabian Journal of Chemistry. 2019 Nov;12(7):1628-1640. https://doi.org/10.1016/j.arabjc.2014.10.003