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

• Published in: Macromolecular chemistry and physics 2023-04, Vol.224 (8), p.n/a
• Main Authors: Fowler, Harriet R., O'Brien, Dara M., Keddie, Daniel J., Alexander, Cameron, Irvine, Derek J., Stockman, Robert A., Howdle, Steven M., Taresco, Vincenzo
• Format: Article
• Language: English
• Subjects: Acrylic resins; aza‐Michael polymerizations; Chemical synthesis; Diols; diol‐terpenes; Esters; Fossil fuels; Monomers; Oxidation; Polymerization; Polymers; Polyols; Terpenes; terpene‐diacrylates; Triols; triol‐terpenes
• ISSN: 1022-1352; 1521-3935
• DOI: 10.1002/macp.202200446

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‐β‐amino esters. With an ever‐growing need to reduce the global dependency on fossil fuels, finding bio‐based/renewable sources is now critical. Herein, the alkene moieties of abundant terpenes are functionalized via oxidation to expand the “toolbox” of bio‐based diols/triols. These polyol compounds are readily converted into the corresponding terpene‐derived diacrylates using mild conditions and polymerized via aza‐Michael polymerizations, forming new (bio)degradable poly‐β‐amino esters.