Influence of oxygen functionalities on the environmental impact of imidazolium based ionic liquids

Several physico-chemical properties relevant to determine the environmental impact of ionic liquids - aqueous solubility, octanol-water partition coefficient and diffusion coefficients in water at infinite dilution - together with toxicity and biodegradability of ionic liquids based on 1-alkyl-3-methylimidazolium cations with or without different oxygenated functional groups (hydroxyl, ester and ether) are studied in this work. The presence of oxygen groups on the imidazolium cation reduces the toxicity of ionic liquids 1-alkyl-3-methylimidazolium with bis(trifluoromethylsulfonyl)imide or octylsulfate anions and simultaneously decreases the value of their octanol-water partition coefficient. The presence of ester functions renders the ionic liquids more easily biodegradable, especially for long alkyl side-chains in the cation but leads to hydrolysis with the formation of reaction products that accumulate. The imidazolium ring is resistant to biodegradability and to abiotic degradation. The oxygen functionalised ionic liquids are more soluble in water and, diffuse more slowly in this medium. (C) 2011 Elsevier B.V. All rights reserved.