Natural deep eutectic solvents from choline chloride and betaine – Physicochemical properties

Aroso, Ivo Manuel Ascensão; Paiva, Alexandre; Reis, Rui L.; Duarte, Ana Rita C.

doi:10.1016/j.molliq.2017.06.051

Cited by 203 publications

(110 citation statements)

References 55 publications

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“…New solvent media have novel capacity to present observable results in chemical kinetics. Deep eutectic solvents (DESs) are now widely introduced as a new class of ionic media like ionic liquids (ILs) and are noticed as an alternative to ILs . They are easily prepared by mixing and heating of two components to produce a composite with a melting point lower than either of its individual components .…”

Section: Introductionmentioning

confidence: 99%

“…Deep eutectic solvents (DESs) are now widely introduced as a new class of ionic media like ionic liquids (ILs) and are noticed as an alternative to ILs. [7][8][9] They are easily prepared by mixing and heating of two components to produce a composite with a melting point lower than either of its individual components. 10 Many recent studies have focused on bulk physical properties, including phase diagrams information, [11][12][13][14] viscosity, density, and electrical conductivity data, [15][16][17][18] and the effect of molecular structure on the physical properties of DESs.…”

Section: Introductionmentioning

confidence: 99%

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Deep eutectic solvent as an operative media on structure‐reactivity relationships

Harifi‐Mood

Khorshahi

2019

Int J of Chemical Kinetics

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Deep eutectic solvents seem to be environmentally friendly solvents, particularly because they are prepared easily and have very low‐vapor pressures under ambient conditions. They are suitable candidates as green solvents for reaction media with special properties. To present this behavior, substitution reactions of some para‐ and meta‐substituted anilines with 1‐fluoro‐2,4‐dinitrobenzene have been spectrophotometrically investigated in varying mole fractions of ethaline as a deep eutectic solvent in dimethyl sulfoxide (DMSO). The measured rate coefficients of the reaction demonstrated a noticeable variation with the increasing mole fraction of ethaline in ethaline‐DMSO mixtures. The linear free energy relationship (LFER) of second‐order rate coefficients based on Hammett's substituent constants demonstrates a reasonably linear straight line with a negative slope in different mole fractions of ethaline‐DMSO mixtures. Another LFER investigation based on the polarity parameters of the media showed a good agreement with hydrogen bond donor and acceptor abilities of the solvent. Non‐LFER assay according to the preferential solvation model confirmed differences between the microsphere solvation of the solute molecules and the bulk composition of the solvents.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Deep eutectic solvent as an operative media on structure‐reactivity relationships

Harifi‐Mood

Khorshahi

2019

Int J of Chemical Kinetics

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“…Based on the available literature, choline salts are characterized by their low toxicity for different cell-lines [15,16], bacteria [17], and other organisms [18]. Moreover, choline salts are industrially available on a large scale.The most widely studied choline salt used in eutectic mixtures is choline chloride [19][20][21][22][23][24][25][26]. One of the first reported DESs was a mixture of choline chloride (liquefaction temperature 302 • C), and urea (melting point 134 • C) that resulted in a 2:1 molar mixture with a remarkable melting point suppression to 12 • C [4].…”

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confidence: 99%

“…The combination of the choline cation with anions derived from carboxylic acids leads to biologically benign ILs, which have been used e.g., in separation processes [31] and microemulsions with low toxicity [32]. As temperature influences the properties of IL mixtures [21,22,25], tailoring the melting point of mixtures opens interesting options for performance optimization. Thus, knowledge of the phase behavior of these IL mixtures is needed to leverage the full application potential of the approach.…”

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Influence of Carboxylate Anions on Phase Behavior of Choline Ionic Liquid Mixtures

et al. 2020

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Mixing ionic liquids is a suitable strategy to tailor properties, e.g., to reduce melting points. The present study aims to widen the application range of low-toxic choline-based ionic liquids by studying eight binary phase diagrams of six different choline carboxylates. Five of them show eutectic points with melting points dropping by 13 to 45 • C. The eutectic mixtures of choline acetate and choline 2-methylbutarate were found to melt at 45 • C, which represents a remarkable melting point depression compared to the pure compounds with melting points of 81 (choline acetate) and 90 • C (choline 2-methylbutarate), respectively. Besides melting points, the thermal stabilities of the choline salt mixtures were investigated to define the thermal operation range for potential practical applications of these mixtures. Typical decomposition temperatures were found between 165 and 207 • C, with choline lactate exhibiting the highest thermal stability.Advantages of DESs compared to pure ILs include easy preparation and therefore low production costs, increased biocompatibility in case of certain components, and bigger variety for customization concerning acidity, hydrophobicity, or polarity. DES systems have demonstrated their practical use in several applications, such as interfacial polymerizations [7], electrochemistry [8], and organic reactions [9].So far, the published research describing IL mixtures has mainly focused on imidazolium [10,11], pyrrolidinium [12], and pyridinium [13] ILs. In these works, significant melting point suppression effects were found for the respective eutectic mixtures. However, imidazolium, pyrrolidinium, and pyridinium ILs and their mixtures face some limitations when it comes to large-scale applications in contact with microorganisms or living matter [14]. Challenges include toxicity aspects and the cost for the organic cation synthesis. This is why a more detailed investigation of choline salts is highly interesting. Based on the available literature, choline salts are characterized by their low toxicity for different cell-lines [15,16], bacteria [17], and other organisms [18]. Moreover, choline salts are industrially available on a large scale.The most widely studied choline salt used in eutectic mixtures is choline chloride [19][20][21][22][23][24][25][26]. One of the first reported DESs was a mixture of choline chloride (liquefaction temperature 302 • C), and urea (melting point 134 • C) that resulted in a 2:1 molar mixture with a remarkable melting point suppression to 12 • C [4]. The typical strategy was to combine choline ILs with molecular compounds such as carboxylic acids, alcohols, and urea derivates [27], and such choline-based DESs have been used in various applications, e.g., as drug solubilization vehicles [28][29][30]. Note, however, that by mixing a choline IL with molecular substances, some of the very attractive IL properties, e.g., non-volatility, non-flammability, and high ionic conductivity can get lost to a large extent. This is why the mixing of two choline ILs is ...

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Green Solvents for Food Processing Applications

Babu

Sangeetha²,

Jaganmohan

2021

Food Chemistry

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Natural deep eutectic solvents from choline chloride and betaine – Physicochemical properties

Cited by 203 publications

References 55 publications

Deep eutectic solvent as an operative media on structure‐reactivity relationships

Deep eutectic solvent as an operative media on structure‐reactivity relationships

Influence of Carboxylate Anions on Phase Behavior of Choline Ionic Liquid Mixtures

Green Solvents for Food Processing Applications

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