Sustainable design for environment-friendly mono and dicationic cholinium-based ionic liquids
authors Silva, FAE; Siopa, F; Figueiredo, BFHT; Goncalves, AMM; Pereira, JL; Goncalves, F; Coutinho, JAP; Afonso, CAM; Ventura, SPM
nationality International
journal ECOTOXICOLOGY AND ENVIRONMENTAL SAFETY
author keywords Monocationic; Dicationic; Ionic liquids; Cholinium; Microtox (R) test; Median effect concentration (EC50)
keywords FUNCTIONALIZED SIDE-CHAINS; FISCHERI MARINE-BACTERIA; AQUEOUS 2-PHASE SYSTEMS; DIFFERENT HEAD GROUPS; VIBRIO-FISCHERI; MUTUAL SOLUBILITIES; CELL-LINES; TOXICITY; IMIDAZOLIUM; WATER
abstract Cholinium-based ionic liquids are receiving crescent interest in diverse areas of application given their biological compatibility and potential for industrial application. In this work, mono and dicationic cholinium ionic liquids as well as cholinium derivatives were synthesized and their toxicity assessed using the luminescent bacteria Vibrio fischeri. A range of cholinium derivatives was synthesized, using different amines and the correspondent brominated derivatives, through the alkylation of the amine with the halide in MeCN. The results indicate that their toxicity is highly dependent on the structural modifications of the cholinium cation, mainly related to the alkyl side or linkage chain length, number of hydroxyethyl groups and insertion of carbon-carbon multiple bonds. The data indicated that it is possible to perform environmentally advantageous structural alterations, namely the addition of double bonds, which would not negatively affect V. fischeri. Moreover, the dicationic compounds revealed a significantly lower toxicity than the monocationic counterparts. The picture emerging from the results supports the idea that cholinium derivatives are promising ionic liquids with a low environmental impact, emphasizing the importance of a careful and directed design of ionic liquid structures. (C) 2014 Elsevier Inc. All rights reserved.
publisher ACADEMIC PRESS INC ELSEVIER SCIENCE
issn 0147-6513
year published 2014
volume 108
beginning page 302
ending page 310
digital object identifier (doi) 10.1016/j.ecoenv.2014.07.003
web of science category Environmental Sciences; Toxicology
subject category Environmental Sciences & Ecology; Toxicology
unique article identifier WOS:000342727800041

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