Abstract:
This thesis describes synthetic studies towards the mechanochemical synthesis of the commodity chemical adipic acid from biomass-derived platform chemicals. The current process for adipic acid production is inefficient due to the use of toxic starting materials derived from limited fossil resources, as well as the production of large amounts of greenhouse gas by products. As an alternative, we propose that a new synthetic route to adipic acid can be achieved mechanochemically, transforming sustainable, biomass-derived platform chemicals into a valuable commodity, in the solid state. The mechanochemical synthesis of adipic acid was attempted from cyclopentanone, a lignocellulose-derived platform chemical, and mucic acid, a dicarboxylic acid derived from carbohydrates, but both routes were plagued with difficulties. Despite significant investigation, both routes proved unsuccessful under all conditions tried, highlighting the necessity for stable reagents and substrates under mechanochemical conditions. Although adipic acid was not attained within the time-frame of this project, several interesting results were discovered that emphasise the potential of mechanochemistry in organic chemistry.