Removal of chlorophenols from aqueous media with hydrophobic deep eutectic solvents: Experimental study and COSMO RS evaluation

Adeyemi, Idowu; Sulaiman, R.; Almazroui, M.; AlHammadi, Ali A.; AlNashef, Inas M.

doi:10.1016/j.molliq.2020.113180

Cited by 65 publications

(32 citation statements)

References 85 publications

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“…14 Therefore, systematic knowledge on the liquid structure and the dominant intermolecular interactions between various components of these mixtures is largely lacking. Limited literature is available on theoretical modeling of hydrophobic DESs, where mainly COSMO-based [26][27][28][29] and PC-SAFT equations of state modeling 16,17,20,21 techniques are used. Despite the widespread use of Molecular Dynamics (MD) simulations for hydrophilic DESs, [30][31][32][33][34][35][36][37][38][39][40][41][42] very few publications are available for hydrophobic DESs.…”

Section: Article Scitationorg/journal/jcpmentioning

confidence: 99%

Thermodynamic, transport, and structural properties of hydrophobic deep eutectic solvents composed of tetraalkylammonium chloride and decanoic acid

Salehi

Celebi

Vlugt

et al. 2021

The Journal of Chemical Physics

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With the emergence of hydrophobic deep eutectic solvents (DESs), the scope of applications of DESs has been expanded to include situations in which miscibility with water is undesirable. Whereas most studies have focused on the applications of hydrophobic DESs from a practical standpoint, few theoretical works exist that investigate the structural and thermodynamic properties at the nanoscale. In this study, Molecular Dynamics (MD) simulations have been performed to model DESs composed of tetraalkylammonium chloride hydrogen bond acceptor and decanoic acid hydrogen bond donor (HBD) at a molar ratio of 1:2, with three different cation chain lengths (4, 7, and 8). After fine-tuning force field parameters, densities, viscosities, self-diffusivities, and ionic conductivities of the DESs were computed over a wide temperature range. The liquid structure was examined using radial distribution functions (RDFs) and hydrogen bond analysis. The MD simulations reproduced the experimental density and viscosity data from the literature reasonably well and were used to predict diffusivities and ionic conductivities, for which experimental data are scarce or unavailable. It was found that although an increase in the cation chain length considerably affected the density and transport properties of the DESs (i.e., yielding smaller densities and slower dynamics), no significant influence was observed on the RDFs and the hydrogen bonds. The self-diffusivities showed the following order for the mobility of the various components: HBD > anion > cation. Strong hydrogen bonds between the hydroxyl and carbonyl groups of decanoic acid and between the hydroxyl group of decanoic acid and chloride were observed to dominate the intermolecular interactions.

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Section: Article Scitationorg/journal/jcpmentioning

confidence: 99%

Thermodynamic, transport, and structural properties of hydrophobic deep eutectic solvents composed of tetraalkylammonium chloride and decanoic acid

Salehi

Celebi

Vlugt

et al. 2021

The Journal of Chemical Physics

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“…Hence, hydrophobic DESs were sought after when extractions from aqueous streams are aimed at and found by, among others, van Osch et al [44], who used high-molecular weight carboxylic acids; Gilmore et al [45] and Schaeffer et al [46], who used trioctylphosphine oxide (TOPO); Cañadas et al [47] who used high-molecular amines; and Abranches et al [48], who demonstrated an unusually strong interaction between aromatic and aliphatic hydroxyl groups and defined this as a type V non-ionic DES. The hydrophobic DESs described by van Osch et al [44] have been studied in liquid-liquid extractions [44,49,50], and hydrophobic DESs, in general, have been applied to remove riboflavin [51], chlorophenols [52], caffeine [53], tryptophan [53], vanillin [53], isophthalic acid [53], platinum group and transition metals [45,46], phenolic antioxidants [47], and polycyclic aromatic hydrocarbons [54] from water.…”

Section: Introductionmentioning

confidence: 99%

Hydrophobic Deep Eutectic Solvents for the Recovery of Bio-Based Chemicals: Solid–Liquid Equilibria and Liquid–Liquid Extraction

et al. 2021

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The solid–liquid equilibrium (SLE) behavior and liquid–liquid extraction (LLX) abilities of deep eutectic solvents (DESs) containing (a) thymol and L-menthol, and (b) trioctylphosphine oxide (TOPO) and L-menthol were evaluated. The distribution coefficients (KD) were determined for the solutes relevant for two biorefinery cases, including formic acid, levulinic acid, furfural, acetic acid, propionic acid, butyric acid, and L-lactic acid. Overall, for both cases, an increasing KD was observed for both DESs for acids increasing in size and thus hydrophobicity. Furfural, being the most hydrophobic, was seen to extract the highest KD (for DES (a) 14.2 ± 2.2 and (b) 4.1 ± 0.3), and the KD of lactic acid was small, independent of the DESs (DES (a) 0.5 ± 0.07 and DES (b) 0.4 ± 0.05). The KD of the acids for the TOPO and L-menthol DES were in similar ranges as for traditional TOPO-containing composite solvents, while for the thymol/L-menthol DES, in the absence of the Lewis base functionality, a smaller KD was observed. The selectivity of formic acid and levulinic acid separation was different for the two DESs investigated because of the acid–base interaction of the phosphine group. The thymol and L-menthol DES was selective towards levulinic acid (Sij = 9.3 ± 0.10, and the TOPO and L-menthol DES was selective towards FA (Sij = 2.1 ± 0.28).

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“…This work constitutes a very simple method that does not entail any modification of the initial conditions of the samples, including pH or temperature, in contrast to others such as that of Ortega-Zamora et al [ 50 ], Mogaddam et al [ 56 ], or Mirzajani et al [ 57 ]. Moreover, the high water stability of the thymol:menthol HNADES employed [ 18 ] in contrast to other DES previously applied for the evaluation of aqueous matrices has been demonstrated [ 50 ].…”

Section: Resultsmentioning

confidence: 99%

“…In this study, HDESs were prepared by mixing two natural secondary metabolites, thymol (as hydrogen bond donor) and menthol (as hydrogen bond acceptor), at molar ratios of 1:1, 1:2, and 2:1. For synthesis, the HDES components were placed in a glass vial and then stirred at 80 °C for 10 min until a homogeneous liquid is formed [ 18 ]. The solvents were cooled to room temperature and stored in a vacuum desiccator to avoid the absorption of moisture.…”

Section: Methodsmentioning

confidence: 99%

Quality assessment of environmental water by a simple and fast non-ionic hydrophobic natural deep eutectic solvent-based extraction procedure combined with liquid chromatography tandem mass spectrometry for the determination of plastic migrants

2021

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Graphical abstract A non-ionic hydrophobic natural deep eutectic solvent (HNADES) based on thymol and menthol was proposed for the liquid-liquid microextraction of fourteen phthalates and one adipate from environmental water samples. Separation, identification, and quantification were achieved by ultra-high-performance liquid chromatography coupled to tandem mass spectrometry. The main factors affecting the extraction efficiency were thoroughly studied. Sample pH of 8 and 100 μL of thymol:menthol at molar ratio 2:1 were selected as the best conditions, while ionic strength and type of dispersant solvent were not relevant for the extraction of the target compounds. The whole methodology was validated for treated wastewater, runoff, and pond water matrices, using di- n -butyl phthalate-3,4,5,6-d 4 and dihexyl phthalate-3,4,5,6-d 4 as surrogates. Recovery ranged from 70 to 127% with relative standard deviation values lower than 14%. Limits of quantification of the method were in the range 0.042–0.425 μg/L for treated wastewater, 0.015–0.386 μg/L for runoff, and 0.013–0.376 μg/L for pond water. The methodology was applied for the analysis of real treated wastewater, runoff, and pond water samples from different places of Tenerife and Gran Canaria (Canary Islands) finding the presence of diethyl phthalate, diallyl phthalate, dipropyl phthalate, benzylbutyl phthalate, di-n-butyl phthalate, bis-(2- n -butoxyethyl) phthalate, di-n-pentyl phthalate, dicyclohexyl phthalate, and bis-(2-ethylhexyl) phthalate at concentrations between 105.2 and 3414 ng/L. Supplementary Information The online version contains supplementary material available at 10.1007/s00216-021-03166-1.

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Removal of chlorophenols from aqueous media with hydrophobic deep eutectic solvents: Experimental study and COSMO RS evaluation

Cited by 65 publications

References 85 publications

Thermodynamic, transport, and structural properties of hydrophobic deep eutectic solvents composed of tetraalkylammonium chloride and decanoic acid

Thermodynamic, transport, and structural properties of hydrophobic deep eutectic solvents composed of tetraalkylammonium chloride and decanoic acid

Hydrophobic Deep Eutectic Solvents for the Recovery of Bio-Based Chemicals: Solid–Liquid Equilibria and Liquid–Liquid Extraction

Quality assessment of environmental water by a simple and fast non-ionic hydrophobic natural deep eutectic solvent-based extraction procedure combined with liquid chromatography tandem mass spectrometry for the determination of plastic migrants

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