Biodegradable ionic liquids: Part I. Concept, preliminary targets and evaluation

The design, preparation and evaluation of biodegradable ionic liquids containing ester or amide groups in the alkyl side chain are presented. Factors improving the biodegradation of surfactants were successfully applied to ionic liquids. These novel ionic liquids can be prepared from readily available starting materials in high yield. The introduction of a group susceptible to enzymatic hydrolysis greatly improves the biodegradation (OECD 301D 'Closed Bottle Test') compared with the commonly used dialkylimidazolium ionic liquids, bmimBF(4) and bmimPF(6). For the 3-methyl-1-(alkyloxycarbonylmethyl)imidazolium bromide series, the greatest biodegradation was observed when alkyl = butyl, pentyl, hexyl and octyl. The corresponding amide analogs proved to be poorly biodegradable.