A series of L-phenylalanine and L-tyrosine ionic liquids (ILs) and tertiary amino analogues have been synthesised according to the 12 principles of green chemistry and a benign by design concept. The series of ILs are derived from amino acid ethyl esters and a variety of different quaternary nitrogen headgroups have been used to give the series of ILs disclosed within. The green chemistry metrics have been calculated for a number of the compounds within and give insight into the chosen synthetic methodologies potential environmental footprint and how improvements to the synthesis pathways may be conducted in the future. The ILs and tertiary amino compounds have been evaluated for their antimicrobial toxicity in collaboration with Dr. Marcel Špulák in Charles University, Czech Republic. A panel of 12 fungi, 4 gram positive bacteria and 4 gram negative bacteria were used to investigate the antimicrobial toxicity of the ILs. The ILs examined showed generally a low antimicrobial toxicity whilst the tertiary amino compounds derived from proline appeared overall to be more toxic towards both bacteria and fungi. The biodegradability of the L-phenylalanine and tertiary amino compounds was examined in collaboration with Prof. Klaus Kümmerer in Leuphana University of Lüneberg, Germany. The test employed was the closed bottle test and a mineraliseable pyridinium derived IL was discovered. Furthermore the metabolic products produced from the biodegradation test were identified by LCMS/MS and the potential breakdown pathways of the ILs has been proposed. Synthesis of the metabolic products was undertaken and further biodegradation and antimicrobial evaluation of these metabolites is ongoing. The information derived from these studies has led to the synthesis of a second generation of linear alkyl and bolaform ILs. The 2nd generation of ILs have been assessed for their green chemistry metrics, surfactant properties as well as their antimicrobial toxicity and biodegradability. The 2nd generation of ILs synthesised were found to possess favourable surface active properties and a broad spectrum antimicrobial activity and moderate to poor biodegradability.