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

Fowler, Harriet R.; O'Brien, Dara M.; Keddie, Daniel J.; Alexander, Cameron; Irvine, Derek J.; Stockman, Robert A.; Howdle, Steven M.; Taresco, Vincenzo

Abstract

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.

Citation

Fowler, H. R., O'Brien, D. M., Keddie, D. J., Alexander, C., Irvine, D. J., Stockman, R. A., Howdle, S. M., & Taresco, V. (2023). Oxidation of Monoterpenes to Form Diols and Triols: A Versatile Toolbox for Polymer Synthesis. Macromolecular Chemistry and Physics, 224(8), Article 2200446. https://doi.org/10.1002/macp.202200446

• Journal Article Type: Article
• Acceptance Date: Jan 6, 2023
• Online Publication Date: Jan 6, 2023
• Publication Date: 2023-04
• Deposit Date: Jan 16, 2023
• Publicly Available Date: Jan 7, 2024
• Journal: Macromolecular Chemistry and Physics
• Print ISSN: 1022-1352
• Electronic ISSN: 1521-3935
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 224
• Issue: 8
• Article Number: 2200446
• DOI: https://doi.org/10.1002/macp.202200446
• Keywords: Materials Chemistry; Organic Chemistry; Polymers and Plastics; Physical and Theoretical Chemistry; Condensed Matter Physics
• Public URL: https://nottingham-repository.worktribe.com/output/15939995
• Publisher URL: https://onlinelibrary.wiley.com/doi/10.1002/macp.202200446