Oxidation of Monoterpenes to Form Diols and Triols: A Versatile Toolbox for Polymer Synthesis

Polyols and polyacrylates have a wide range of applications in polymer synthesis as monomers, initiators, or building blocks in a variety of polymerization reaction types. With an ever-growing need to reduce the global dependency on fossil fuels, finding bio-based/renewable sources for these compounds is now critical. Herein, the alkene moieties of common, abundant terpenes are functionalized via oxidation to expand the "toolbox" of bio-based diols and triols. These polyol compounds are readily converted into the corresponding terpene-derived diacrylates using mild conditions. As a proof of concept, it is demonstrated that these monomers can be used in aza-Michael polymerizations, forming new (bio)degradable poly-beta-amino esters.