Predicting the density and viscosity of hydrophobic eutectic solvents: towards the development of sustainable solvents

Lemaoui, Tarek; Darwish, Ahmad S.; Attoui, Ayoub; Hatab, Farah Abu; Hammoudi, N.; Benguerba, Yacine; Vega, Lourdes F.; AlNashef, Inas M.

doi:10.1039/d0gc03077e

Cited by 98 publications

(85 citation statements)

References 100 publications

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“…al.) for predicting the density of DES [ 20 , 21 ]. The first study [ 20 ] was based on hydrophilic DES, whereas the second, more recent one [ 21 ] focused solely on hydrophobic DES.…”

Section: Introductionmentioning

confidence: 99%

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Density of Deep Eutectic Solvents: The Path Forward Cheminformatics-Driven Reliable Predictions for Mixtures

et al. 2021

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Deep eutectic solvents (DES) are often regarded as greener sustainable alternative solvents and are currently employed in many industrial applications on a large scale. Bearing in mind the industrial importance of DES—and because the vast majority of DES has yet to be synthesized—the development of cheminformatic models and tools efficiently profiling their density becomes essential. In this work, after rigorous validation, quantitative structure-property relationship (QSPR) models were proposed for use in estimating the density of a wide variety of DES. These models were based on a modelling dataset previously employed for constructing thermodynamic models for the same endpoint. The best QSPR models were robust and sound, performing well on an external validation set (set up with recently reported experimental density data of DES). Furthermore, the results revealed structural features that could play crucial roles in ruling DES density. Then, intelligent consensus prediction was employed to develop a consensus model with improved predictive accuracy. All models were derived using publicly available tools to facilitate easy reproducibility of the proposed methodology. Future work may involve setting up reliable, interpretable cheminformatic models for other thermodynamic properties of DES and guiding the design of these solvents for applications.

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“…al.) for predicting the density of DES [ 20 , 21 ]. The first study [ 20 ] was based on hydrophilic DES, whereas the second, more recent one [ 21 ] focused solely on hydrophobic DES.…”

Section: Introductionmentioning

confidence: 99%

“…for predicting the density of DES [ 20 , 21 ]. The first study [ 20 ] was based on hydrophilic DES, whereas the second, more recent one [ 21 ] focused solely on hydrophobic DES. However, both studies pertained to a smaller number of data points compared to those handled herein.…”

Section: Introductionmentioning

confidence: 99%

Density of Deep Eutectic Solvents: The Path Forward Cheminformatics-Driven Reliable Predictions for Mixtures

et al. 2021

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“…To decrease the viscosity, hydrophilic DES are usually diluted with water, but this is impossible for hydrophobic DES. The viscosity of several hydrophobic DES is available in the literature [ 6 , 14 , 15 , 16 , 17 ]. However, the existing data are only for mixtures at a specific molar ratio, usually at or close to the eutectic point.…”

Section: Introductionmentioning

confidence: 99%

“…However, the existing data are only for mixtures at a specific molar ratio, usually at or close to the eutectic point. In most of the literature, the viscosity of DES was studied and discussed by treating eutectic mixtures of constituents with a fixed composition as a pseudo-compound without considering the effects of the constituents or their molar ratio [ 11 , 15 , 18 , 19 , 20 , 21 ].…”

Section: Introductionmentioning

confidence: 99%

Influence of the Molecular Structure of Constituents and Liquid Phase Non-Ideality on the Viscosity of Deep Eutectic Solvents

2021

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Hydrophobic deep eutectic solvents (DES) have recently been used as green alternatives to conventional solvents in several applications. In addition to their tunable melting temperature, the viscosity of DES can be optimized by selecting the constituents and molar ratio. This study examined the viscosity of 14 eutectic systems formed by natural substances over a wide range of temperatures and compositions. The eutectic systems in this study were classified as ideal or non-ideal based on their solid–liquid equilibria (SLE) data found in the literature. The eutectic systems containing constituents with cyclohexyl rings were considerably more viscous than those containing linear or phenyl constituents. Moreover, the viscosity of non-ideal eutectic systems was higher than that of ideal eutectic systems because of the strong intermolecular interactions in the liquid solution. At temperatures considerably lower than the melting temperature of the pure constituents, non-ideal and ideal eutectic systems with cyclohexyl constituents exhibited considerably high viscosity, justifying the kinetic limitations in crystallization observed in these systems. Overall, understanding the correlation between the molecular structure of constituents, SLE, and the viscosity of the eutectic systems will help in designing new, low-viscosity DES.

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“…DESs are commonly described as a mixture of two or more compounds that form upon mixing a liquid phase with a melting point far below that of its constituents [23][24][25]. It is anticipated that the formation of the DES occurs via a combination of entropy of mixing, van der Waals interactions, and hydrogen bonding, where one compound is considered a hydrogen bond donor (HBD) and the other is a hydrogen bond acceptor (HBA).…”

Section: Introductionmentioning

confidence: 99%

Green Extraction of Volatile Fatty Acids from Fermented Wastewater Using Hydrophobic Deep Eutectic Solvents

et al. 2021

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Volatile fatty acids (VFAs) are carboxylic acids mainly produced via the fermentation of organic waste streams. Being industrial platform chemicals, sustainable, green and economical recovery of VFAs is necessary. Herein, hydrophobic deep eutectic solvents (HDES), “a new generation of water-immiscible designer solvents”, were assessed for the recovery of VFAs via liquid–liquid extraction. The eutectic mixture of menthol-lauric acid exhibited the highest stability and hydrophobicity. The binary solubility of the pairs {VFA in water} and {VFA in HDES}—and the saturation of the HDES with water were measured. Furthermore, the influences of key parameters on the extraction efficiency were investigated. On multi-stage extraction, an efficiency of 88% was achieved in 4 stages, and the HDES was successfully regenerated using vacuum evaporation. The HDES performance was also compared to other reported relevant solvents. It was concluded that menthol-lauric acid HDES is a promising candidate for the green extraction of VFAs from fermented wastewater.

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Predicting the density and viscosity of hydrophobic eutectic solvents: towards the development of sustainable solvents

Abstract: The interest in green and sustainable solvents has been dramatically increasing in recent years because of the growing awareness of the impact of classical organic solvents on environmental pollution and human health.

Cited by 98 publications

References 100 publications

Density of Deep Eutectic Solvents: The Path Forward Cheminformatics-Driven Reliable Predictions for Mixtures

Density of Deep Eutectic Solvents: The Path Forward Cheminformatics-Driven Reliable Predictions for Mixtures

Influence of the Molecular Structure of Constituents and Liquid Phase Non-Ideality on the Viscosity of Deep Eutectic Solvents

Green Extraction of Volatile Fatty Acids from Fermented Wastewater Using Hydrophobic Deep Eutectic Solvents

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