Designing the ammonium cation to achieve a higher hydrophilicity of bistriflimide-based ionic liquids

Ferro, André Mão de; Reis, Patrícia M.; Soromenho, Mário R. C.; Bernardes, Carlos E. S.; Shimizu, Karina; Freitas, Adilson A.; Esperança, José M. S. S.; Lopes, José N. Canongia; Rebelo, Luís Paulo N.

doi:10.1039/c8cp03398f

Cited by 16 publications

(18 citation statements)

References 29 publications

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“…The topics tackled in this contribution are not comprehensive. Examples not herein presented include: their ability to form halogen-bonds (Bernardes and Canongia Lopes, 2017; Saccone et al, 2017; Cavallo et al, 2018; Lodeiro et al, 2018), the formation of liquid crystals (Alvarez Fernandez and Kouwer, 2016; Goossens et al, 2016), the total miscibility in water of fluorinated ILs (Pereiro et al, 2015; de Ferro et al, 2018), and other unexpected behavior in respect to their physical properties (Singh et al, 2015, 2017; Dzida et al, 2018; Rahman and Senapati, 2018). Zwitterionic liquids (Blesic et al, 2017; Ohno et al, 2018; Wu et al, 2018), which fill the gap between small-ion ILs and ILs with strong H-bonds, as well as hydrated ILs (Haberler et al, 2012; Fujita et al, 2016), where H-bonds between one or both of the ions and a small number of water molecules is sufficient to produce new materials with superior properties, constitute other examples of not so-well-known behavior.…”

Section: Introductionmentioning

confidence: 99%

Anomalous and Not-So-Common Behavior in Common Ionic Liquids and Ionic Liquid-Containing Systems

et al. 2019

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This work highlights unexpected, not so well known responses of ionic liquids and ionic liquid-containing systems, which are reported in a collective manner, as a short review. Examples include: (i) Minima in the temperature dependence of the isobaric thermal expansion coefficient of some ILs; (ii) Viscosity Minima in binary mixtures of IL + Molecular solvents; (iii) Anomalies in the surface tension within a family of ILs; (iv) The constancy among IL substitution of C p /V m at and around room temperature; (v) ILs as glass forming liquids; (vi) Alternate odd-even side alkyl chain length effects; (vii) Absolute negative pressures in ILs and IL-containing systems; (viii) Reversed-charged ionic liquid pairs; (ix) LCST immiscibility behavior in IL + solvent systems.

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Section: Introductionmentioning

confidence: 99%

Anomalous and Not-So-Common Behavior in Common Ionic Liquids and Ionic Liquid-Containing Systems

et al. 2019

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“…We manipulated the chemical structure of the cholinium cation by grafting it with additional hydroxyethyl moieties to produce water soluble bistriflimide-based ILs. Complete water miscibility of the studied ILs (shown in Figure 1) is achieved due to the large number of OH groups at the cation, contributing to stronger hydrogen-bonding with water (de Ferro et al, 2018).…”

Section: Resultsmentioning

confidence: 99%

“…The chemical structures of the ILs used in this work [ N -methyl- N,N,N -tris(2-hydroxyethyl)ammonium bistriflimide, [N 1(2OH) (2OH) (2OH) ][NTf 2 ]; N -ethyl- N,N,N -tris(2-hydroxyethyl)ammoniumbistriflimide,[N 2(2OH)(2 OH ) (2 OH ) ][NTf 2 ]; N, N -dimethyl- N,N -bis(2-hydroxyethyl) ammonium bistriflimide, [N 11(2OH) (2OH) ][NTf 2 ]] are presented in Figure 1. The ILs investigated were synthesized according to the protocol described by de Ferro et al (2018). The AgNO 3 test was performed to all ILs to confirm the absence of halides (chloride or bromide).…”

Section: Methodsmentioning

confidence: 99%

Simultaneous Separation of Antioxidants and Carbohydrates From Food Wastes Using Aqueous Biphasic Systems Formed by Cholinium-Derived Ionic Liquids

et al. 2019

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The food industry produces significant amounts of waste, many of them rich in valuable compounds that could be recovered and reused in the framework of circular economy. The development of sustainable and cost-effective technologies to recover these value added compounds will contribute to a significant decrease of the environmental footprint and economic burden of this industry sector. Accordingly, in this work, aqueous biphasic systems (ABS) composed of cholinium-derived bistriflimide ionic liquids (ILs) and carbohydrates were investigated as an alternative process to simultaneously separate and recover antioxidants and carbohydrates from food waste. Aiming at improving the biocompatible character of the studied ILs and proposed process, cholinium-derived bistriflimide ILs were chosen, which were properly designed by playing with the cation alkyl side chain and the number of functional groups attached to the cation to be able to create ABS with carbohydrates. These ILs were characterized by cytotoxicity assays toward human intestinal epithelial cells (Caco-2 cell line), demonstrating to have a significantly lower toxicity than other well-known and commonly used fluorinated ILs. The capability of these ILs to form ABS with a series of carbohydrates, namely monosaccharides, disaccharides and polyols, was then appraised by the determination of the respective ternary liquid-liquid phase diagrams at 25°C. The studied ABS were finally used to separate carbohydrates and antioxidants from real food waste samples, using an expired vanilla pudding as an example. With the studied systems, the separation of the two products occurs in one-step, where carbohydrates are enriched in the carbohydrate-rich phase and antioxidants are mainly present in the IL-rich phase. Extraction efficiencies of carbohydrates ranging between 89 and 92% to the carbohydrate-rich phase, and antioxidant relative activities ranging between 65 and 75% in the IL-rich phase were obtained. Furthermore, antioxidants from the IL-rich phase were recovered by solid-phase extraction, and the IL was recycled for two more times with no losses on the ABS separation performance. Overall, the obtained results show that the investigated ABS are promising platforms to simultaneously separate carbohydrates and antioxidants from real food waste samples, and could be used in further related applications foreseeing industrial food waste valorization.

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“…The addition of alcohol to IL solutions also highlights the dual role of the alkyl chain of the alcohol molecules, interacting with the polar and nonpolar regions of the IL [ 29 , 30 ]. The water solubility along an IL series is, as expected, lower for ILs with longer alkyl side chains in the cation.…”

Section: Introductionmentioning

confidence: 99%

Ionic Liquids and Water: Hydrophobicity vs. Hydrophilicity

et al. 2021

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Many chemical processes rely extensively on organic solvents posing safety and environmental concerns. For a successful transfer of some of those chemical processes and reactions to aqueous media, agents acting as solubilizers, or phase-modifiers, are of central importance. In the present work, the structure of aqueous solutions of several ionic liquid systems capable of forming multiple solubilizing environments were modeled by molecular dynamics simulations. The effect of small aliphatic chains on solutions of hydrophobic 1-alkyl-3-methylimidazolium bis(trifluoromethyl)sulfonylimide ionic liquids (with alkyl = propyl [C3C1im][NTf2], butyl [C4C1im][NTf2] and isobutyl [iC4C1im][NTf2]) are covered first. Next, we focus on the interactions of sulphonate- and carboxylate-based anions with different hydrogenated and perfluorinated alkyl side chains in solutions of [C2C1im][CnF2n+1SO3], [C2C1im][CnH2n+1SO3], [C2C1im][CF3CO2] and [C2C1im][CH3CO2] (n = 1, 4, 8). The last system considered is an ionic liquid completely miscible with water that combines the cation N-methyl-N,N,N-tris(2-hydroxyethyl)ammonium [N1 2OH 2OH 2OH]+, with high hydrogen-bonding capability, and the hydrophobic anion [NTf2]–. The interplay between short- and long-range interactions, clustering of alkyl and perfluoroalkyl tails, and hydrogen bonding enables a wealth of possibilities in tailoring an ionic liquid solution according to the needs.

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Designing the ammonium cation to achieve a higher hydrophilicity of bistriflimide-based ionic liquids

Cited by 16 publications

References 29 publications

Anomalous and Not-So-Common Behavior in Common Ionic Liquids and Ionic Liquid-Containing Systems

Anomalous and Not-So-Common Behavior in Common Ionic Liquids and Ionic Liquid-Containing Systems

Simultaneous Separation of Antioxidants and Carbohydrates From Food Wastes Using Aqueous Biphasic Systems Formed by Cholinium-Derived Ionic Liquids

Ionic Liquids and Water: Hydrophobicity vs. Hydrophilicity

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