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.

Automated summary

Polyols and polyacrylates are widely used in polymer synthesis and can be used as monomers, initiators, or building blocks. Finding bio-based/renewable sources for these compounds is crucial due to the increasing need to reduce dependency on fossil fuels. By functionalizing the alkene moieties of common terpenes through oxidation, the toolbox of bio-based diols and triols is expanded. These polyols can be easily converted into terpene-derived diacrylates under mild conditions. As demonstrated, these monomers can be used in aza-Michael polymerizations to form new (bio)degradable poly-beta-amino esters.