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., …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