Hydrophobic eutectic solvents for extraction of natural phenolic antioxidants from winery wastewater

Cañadas, Raquel; González, Emilio J.; Díaz, Ismael; Rodríguez, Manuel

doi:10.1016/j.seppur.2020.117590

Cited by 47 publications

(18 citation statements)

References 63 publications

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“…This makes many DESs quite hygroscopic [43], and this limits their applicability in biorefinery applications where aqueous streams are common. 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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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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“…Further, H(D)ESs have included other carboxylic acids as well natural compounds like camphor, menthol, thymol as HBAs or HBDs. 49,50 In other cases, these H(D)ESs originate from the interaction of phenolic and aliphatic compounds, as explained for the type V of these neoteric solvents. 40…”

Section: Characteristics Of Dess In Relation With Metal Recoverymentioning

confidence: 94%

Status and advances of deep eutectic solvents for metal separation and recovery

et al. 2022

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“…ESs are composed of hydrogen bond acceptors (HBAs) and hydrogen bond donors (HBDs), which are able to self-associate due to the generation of intermolecular hydrogen bonds that form a eutectic point presenting a lower melting point than the individual components. ,, ESs prepared from natural products and biological molecules (choline, amino acids, organic acids, sugars, etc.) are the so-called natural (deep) eutectic solvents (NADESs or NAESs), and they can be safely used in food, pharmaceutical, and cosmetics industries. , ESs have recently shown to be effective solvents for the valorization of agri-food waste by means of natural polyphenolic antioxidants recovery. , Moreover, hydrophobic ESs (HESs) can be adopted as solvents for the extraction of compounds of interest from aqueous environments. − For instance, Ribeiro et al successfully extracted vanillin from aqueous environments using novel eutectic mixtures based on dl -menthol and naturally occurring acids, obtaining a partition coefficient of 5.72 with the dl -menthol:lactic acid 1:1 eutectic mixture . The use of NAESs, which consisted of mixtures of two or more common natural products (such as choline chloride, organic acids, sugars, and glycerol, among others), combined in specific molar proportions, has also been evaluated to study the solubility of pure vanillin in them and the management of extracting between 7.6–16.7 mg/g of vanillin from vanilla beans, in this case from solid matrices …”

Section: Introductionmentioning

confidence: 99%

Sustainable Recovery of High Added-Value Vanilla Compounds from Wastewater Using Green Solvents

Cañadas

González‐Miquel

González

et al. 2021

ACS Sustainable Chem. Eng.

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The growing demand for high added-value products, such as vanilla-derived compounds, and increasing environmental regulations make evident the need to find new sustainable solvents for extraction processes, which meet both legislative requirements and expected yields. Vanilla-derived compounds are known for their antioxidant and beneficial properties for human health. These compounds can be recovered from effluent streams, promoting decontamination and revaluation of wastewater. The potential of using neoteric solvents, i.e., biobased solvents and hydrophobic eutectic solvents, as an alternative to conventional volatile organic solvents, such as ethyl acetate, for sustainable recovery of vanilla-derived compounds through liquid–liquid extraction from aqueous environments was investigated. Three biobased solvents (2-methyltetrahydrofuran, cyclopentyl methyl ether, and d-limonene) and three hydrophobic eutectic solvents constituted by menthol and organic acids (1:1 dl-menthol:octanoic acid, 1:1 dl-menthol:decanoic acid, and 2:1 dl-menthol:dodecanoic acid) were evaluated. The extraction process was optimized in terms of the stirring time and solvent:feed volume ratio. The effect of the initial solute concentration was also analyzed. The extraction efficiency of solvents was determined by UV–visible spectrophotometry and high-performance liquid chromatography with diode-array detection. The experimental results indicated that 2-methyltetrahydrofuran yielded the highest extraction efficiency from a vanilla bean extract solution for both vanillin (95.37%) and vanillic acid (91.96%) with good repeatability (RSD < 0.40%). Regarding the rest of the neoteric solvents, cyclopentyl methyl ether and hydrophobic eutectic solvents provided extraction values between 31.6 and 95.4% for both vanilla-derived compounds, while d-limonene was significantly less effective. Finally, a solvent recycling and reuse study was successfully carried out, showing that 2-methyltetrahydrofuran stands out as a promising biobased extraction solvent for sustainable recovery of valuable vanilla constituents.

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Hydrophobic eutectic solvents for extraction of natural phenolic antioxidants from winery wastewater

Cited by 47 publications

References 63 publications

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

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

Status and advances of deep eutectic solvents for metal separation and recovery

Sustainable Recovery of High Added-Value Vanilla Compounds from Wastewater Using Green Solvents

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