An experimental and theoretical investigation of the physicochemical properties on choline chloride – Lactic acid based natural deep eutectic solvent (NADES)

Alcalde, Rafael; Gutiérrez, Alberto; Atilhan, Mert; Aparício, Santiago

doi:10.1016/j.molliq.2019.110916

Cited by 73 publications

(44 citation statements)

References 60 publications

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“…The addition of NADES leads to the gradual increase in ionic conductivity up to 1.7 mS/cm for the films containing 82 wt% of NADES. This value is comparable to the conductivity of the pure LA-ChCl NADES with low water content [37], which along with results of other methods confirms the successful formation of NADES inside CS films. The linear dependences of the logarithm of conductivity on the reciprocal temperature ( Figure 11a) give possibility to find the activation energy of ionic conductivity for the prepared films.…”

Section: Ionic Conductivity and Transport Properties Of Cs/des Filmssupporting

confidence: 85%

“…However, to the best of our knowledge, the electrochemical properties of CS-LA-ChCl plasticized films prepared via solution casting were not studied yet. It was reported recently that NADES based on ChCl and LA (1:1 mole:mole) demonstrate ionic conductivity 0.2-10 mS/cm depending on water content [37]. Thus, it can be presumed, that introduction of this NADES into CS is interesting for the preparation of ionically conducting films.…”

Section: Introductionmentioning

confidence: 90%

“…Polymers 2020, 12, x FOR PEER REVIEW 3 of 19 depending on water content [37]. Thus, it can be presumed, that introduction of this NADES into CS is interesting for the preparation of ionically conducting films.…”

Section: Films Preparationmentioning

confidence: 99%

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Ionic Conductivity and Structure of Chitosan Films Modified with Lactic Acid-Choline Chloride NADES

et al. 2020

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The natural deep eutectic solvent (NADES) based on choline chloride (ChCl) and lactic acid (LA) was used for the preparation of chitosan (CS) films by the solution casting method. The content of NADES in films was from 0 to 82 wt%. The impact of NADES on the morphology and crystalline structure of films was investigated using scanning electron microscopy as well as wide-angle and small-angle X-ray scattering. The experimental results allow to propose CS chains swelling in NADES. FTIR spectroscopy confirms the interactions between CS and NADES components via the formation of hydrogen and ion bonds. The thermal properties of the composite films were studied by simultaneous thermogravimetric and differential thermal analysis. Thermomechanical analysis demonstrated appearance of two transitions at temperatures between −23 and −5 °C and 54–102 °C depending on NADES content. It was found that electrical conductivity of film with 82 wt% of NADES reaches 1.7 mS/cm. The influence of the composition and structure of films on the charge carriers concentration and their mobility is discussed.

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Section: Ionic Conductivity and Transport Properties Of Cs/des Filmssupporting

confidence: 85%

Section: Introductionmentioning

confidence: 90%

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Ionic Conductivity and Structure of Chitosan Films Modified with Lactic Acid-Choline Chloride NADES

et al. 2020

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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].…”

mentioning

confidence: 99%

“…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].…”

mentioning

confidence: 99%

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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Chiral Eutectic Mixtures and Deep Eutectic Solvents for Induced Circularly Polarized Luminescence

et al. 2021

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Deep eutectic solvents (DES) or eutectic mixtures prepared with a chiral component can lead to new chiral solvents with applications that include asymmetric synthesis and chiral light emitting materials. DES have low melting points, because of strong interactions, such as hydrogen bonding, between components of the mixture. Mixtures are prepared with ammonium salts, tetrabutylammonium chloride ([TBA]Cl) and choline chloride ([Ch]Cl), as hydrogen bond acceptor (HBA) and L‐lactic acid, L‐leucic acid, L‐ascorbic acid, R/S‐acetoxypropionic acid, and methyl‐(S)‐lactate as chiral hydrogen bond donors (HBD). Eight combinations of the HBAs and HBDs were prepared, and a racemic mixture of dissymmetric chiral europium complexes was dissolved in the mixtures. The circularly polarized luminescence (CPL) spectra were measured to determine the chiral discrimination by these chiral solvents. The CPL spectra show that the handedness of the chiral HBD is important to the chiral discrimination exhibited. However, the inversion of the sign of the CPL spectra in 1 : 3 [TBA]Cl:L‐lactic acid vs. 1 : 3 [Ch]Cl:L‐lactic acid, and 1 : 1.5 [Ch]Cl:L‐leucic acid vs. 1 : 1 [TBA]Cl:L‐leucic acid shows that the achiral HBA also plays a critical role in the handedness of the chiral discrimination by the chiral solvent.

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An experimental and theoretical investigation of the physicochemical properties on choline chloride – Lactic acid based natural deep eutectic solvent (NADES)

Cited by 73 publications

References 60 publications

Ionic Conductivity and Structure of Chitosan Films Modified with Lactic Acid-Choline Chloride NADES

Ionic Conductivity and Structure of Chitosan Films Modified with Lactic Acid-Choline Chloride NADES

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

Chiral Eutectic Mixtures and Deep Eutectic Solvents for Induced Circularly Polarized Luminescence

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