Exploring the usefulness of key green physicochemical properties: Quantitative structure–activity relationship for solvents from biomass

Abstract

In recent decades there has been a growing interest in the development of new solvents from biomass. Some of these new solvents have been classified as green because of their renewable and sustainable source. However, characterization from the ecotoxicological and physicochemical points of view is needed to categorize them as green solvents. We have selected several key physicochemical properties that can reflect environmental features (density, boiling point, critical aggregation concentration, and log p) and explored their usefulness for preliminarily assessing the green character of the studied solvents. Specifically, we have studied several solvents from biomass: lactate family (methyl, ethyl, and butyl lactate), furfural family (furfural, 5-methylfurfural, furfuryl alcohol, and tetrahydrofurfuryl alcohol), and levulinate family (methyl, ethyl, and butyl levulinate). To fill the gaps and complete some toxicity data for the environment, we have measured the ecotoxicity using 2 of the most common and versatile biomodels, bacteria Vibrio fischeri and crustacean Daphnia magna, for furfural- and lactate-derived compounds. The results indicate that solvents from biomass can be categorized as green because their toxicity for the environment is low. Finally, a quantitative structure-activity relationship (QSAR) study was performed with the selected key properties and the ecotoxicological information. Despite the different structure of the chemicals under study, good correlations were found for the studied organisms. It seems that log p and critical aggregation concentration reflect the greatest part of the ecotoxic behavior, whereas density and boiling point cannot reflect toxicity signals. However, these properties are rather useful for assessing the final environmental fate of the studied chemicals. Environ Toxicol Chem 2018;37:1014-1023. © 2017 SETAC.

Kinetics of Alkyl Lactate Formation from the Alcoholysis of Poly(Lactic Acid)

“…ALs do not present potential health risks in terms of teratogenicity, maternal toxicity or systemic toxicity [4]. Biodegradability and ecotoxicological studies have also shown that they are environmental-friendly compounds with low ecotoxicity [5,6].…”

Evaluation of the toxicity profiles of three families of solvents from biomass: levulinate, lactate and furfural derivatives

“…For that, previous studies have shown that the physicochemical properties of these solvents are suitable to consider them as green solvents. [18][19][20][21][22] The ecotoxicological effect of each of these solvents on different aquatic organisms and different levels of the food chain a (Allivibrio fischeri bacteria, Daphnia magna crustacean and Danio rerio fish embryos) has also been studied and reported. 2,[22][23][24][25][26][27] Overall, these studies showed that the ecotoxicity of these compounds is low; however, slight ecotoxicity was observed for butyl levulinate in A. fischeri bacteria, for furfural and 5-methylfurfural in D. magna and for ethyl and butyl levulinates, butyl lactate and furfural in D. rerio.…”

“…[18][19][20][21][22] The ecotoxicological effect of each of these solvents on different aquatic organisms and different levels of the food chain a (Allivibrio fischeri bacteria, Daphnia magna crustacean and Danio rerio fish embryos) has also been studied and reported. 2,[22][23][24][25][26][27] Overall, these studies showed that the ecotoxicity of these compounds is low; however, slight ecotoxicity was observed for butyl levulinate in A. fischeri bacteria, for furfural and 5-methylfurfural in D. magna and for ethyl and butyl levulinates, butyl lactate and furfural in D. rerio. Therefore, different levels of ecotoxicity have been found across the various tests used and among the different solvents studied, which may indicate that there are different mechanisms of toxicity depending on the organism.…”

Ecotoxicological study of bio-based deep eutectic solvents formed by glycerol derivatives in two aquatic biomodels

“…in the pharmaceutical industry. 5 Some of these new solvents are biomass derivatives, 6 supercritical fluids, 7 ionic liquids (ILs) 8 and deep eutectic solvents (DES). 9 According to the principles of Green Chemistry, 10 solvents should present low vapour pressures and high boiling points, good recyclability, high solvating power, be environmentally and humanly safe and have renewable origin.…”