The chemical and thermal stability of ionic liquids (ILs) makes them interesting for a large variety of applications in nearly all areas of the chemical industry. However, this stability is often reflected in their recalcitrance towards biodegradation, which comes with the risk of persistence when they are released into the environment. In this study we carried out a systematic investigation of the biodegradability of pyrrolidinium, morpholinium, piperidinium, imidazolium and pyridinium-based IL cations substituted with different alkyl or functionalised side chains and using halide counterions. We examined their primary degradability by specific analysis and/or their ultimate biodegradability using biochemical oxygen demand tests according to OECD guideline 301F. Biological transformation products were investigated using mass spectrometry. A comparison of the biodegradation potential of these ILs shows that for all five head groups, representatives can be found that are readily or inherently biodegradable, thus permitting the structural design of ILs with a reduced environmental hazard. † Electronic supplementary information (ESI) available. See

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Ionic liquids (ILs) formed by multivalent cations are generally of higher thermal and electrochemical stability, which makes them attractive for use in high-temperature applications. Whereas the influence of structural elements on the physicochemical properties of dicationic ILs (DILs) is well established, such systematic investigations on their ecotoxicity and biodegradablility are still lacking. The present study investigates the influence of the dicationic structural elements on these characteristics and addresses the question whether already established structure-activity relationships of common ILs can be applied to DILs.Therefore, a set of 10 DILs with different linkage chain length, terminal alkyl side chain length, linkage chain polarity and head groups were synthesized and studied in several biodegradation and toxicity tests. The results showed that the acute toxicity was in many cases below the levels observed for monocationic ILs. However, none of the DILs could be degraded within the performed biodegradation experiments. Hence, DILs are a potential less toxic alternative to monocationic ILs, but further work on their design is necessary.

The idea of green or sustainable chemistry is to develop highly efficient technical processes and applications using chemicals with a reduced or zero hazard potential for man and the environment. This approach is perfectly applicable to ionic liquids (ILs). These substances have potential applications in different fields (economic interests), and so far millions of possible structures have been designed, thousands of which have actually been produced, providing a broad base for the structural design of ILs with optimal technological properties and at the same time posing a reduced hazard to humans and the environment. In parallel with the rapidly growing (eco) toxicological knowledge regarding ILs, the available data regarding their biodegradability are also increasing. The following sections introduce the reader to biodegradation test procedures and present an overview of existing aerobic and anaerobic biodegradation data concerning ILs. Besides pure biodegradation kinetics, this discussion covers data on biological degradation products (metabolites) and abiotic degradation processes. Throughout this review special emphasis will be placed on structure-biodegradability relationships and the question whether the 10 th principle of Green Chemistry, namely, Design chemicals and products to degrade after use: design chemical products to break down to innocuous substances after use so that they do not accumulate in the environment, is or is not fulfilled for some IL structures. The discussion of this data should help to improve the future design of inherently safer ILs, thereby reducing the risks they may pose to humans and the environment.