Application of a computational model of natural deep eutectic solvents utilizing the COSMO-RS approach for screening of solvents with high solubility of rutin

Abstract

The screening of natural deep eutectic solvents (NADES) to identify those with the ability to strongly solvate rutin was conducted using the COSMO-RS methodology. A NADES model was constructed that took into account the possible ionic and neutral forms of its constituents. The distributions of all forms were computed based on the equilibrium constants of neutralization reactions between amino and carboxylic acids. The proposed model was validated against the experimental solubilities of 15 NADES. A linear relationship between these data and the estimated activity coefficient values was found. The screening encompassed 126 different NADES. It was found that ten of them outperformed the best reference system. The most effective two-component solvent comprised proline combined with 2,3-diaminosuccinic acid, and the solubility of rutin in this solvent was found to be 130% greater than its solubility in the best reference system. The amino acids associated with the highest rutin solubilities were all cyclic, and the use of carboxylic acids with two carboxyl groups and a main chain consisting of two methylene groups with two amino substituents was observed to yield the best rutin solubilities. Because of the acidic properties of rutin, the presence of basic sites on the components of the NADES generally leads to enhanced solubility.Electronic supplementary materialThe online version of this article (10.1007/s00894-018-3700-1) contains supplementary material, which is available to authorized users.

Application of Deep Eutectic Solvents for the Extraction of Rutin and Rosmarinic Acid from Satureja montana L. and Evaluation of the Extracts Antiradical Activity

“…According to the literature [42,43], rutin is extracted from different plants with DESs, especially with acidic DESs, such as choline chloride:citric acid (mole ratio 2:1) or proline:2,3-diaminosuccinic acid, which is in agreement with our results. For the analysis of rutin, which is one of the frequently extracted components using DESs, the COSMO-RS program (COSMOConfX16software; SCM Software for Chemistry and Materials, Amsterdam, The Netherlands) was used to analyze 126 DESs, showing that the most effective solvents were cyclic.…”

“…Since rutin has acidic properties, the presence of basic sites on the components of the DESs could be the reason for the improved extraction. In the case of the preparation of DESs with carboxylic acids as HBDs for extraction of rutin, the high acidity of the carboxylic acid component of the DESs and a large number of highly basic centers is important, which was also confirmed by our results [43].…”

Deep eutectic solvents on extraction of bisphenol A from water matrices: COnductor like Screening MOdel for Real Solvents prediction and experimental validation

“…Furthermore, traditional solvent extraction process used a variety of solvents including water, ethanol, acetonitrile, ethanol, hexane, acetones, other organic solvents, and their mixtures. But these solvents have significant disadvantages such as (i) low selectivity, (ii) low capacity, (iii) low efficiency, (iv) poor solubility of BPA in solvents, and (v) the presence of residual solvent in the sample 4–8 . Additionally, these solvents have high volatility and toxicity which makes it difficult to extract BPA from the aquatic environment 9,10 .…”

“…Additionally, these solvents have high volatility and toxicity which makes it difficult to extract BPA from the aquatic environment 9,10 . Therefore, there is a need for alternatives that offer enhanced extraction abilities and are more environmentally friendly than traditional solvent extraction 6 …”

Fast and Efficient Method to Evaluate the Potential of Eutectic Solvents to Dissolve Lignocellulosic Components

“…The use of COSMO-RS as a tool to verify the potential for dissolution of biomass fractions using ionic liquids (ILs) [40,41] and ESs [42] is described in the literature. However, this procedure requires a precise definition of the solvent and solute and needs validation at the laboratory bench.…”