Novel biodegradable polyesters based on lignin-derived 3-carboxymuconolactone
• (4 S )-3-Carboxymuconolactone (3CML) was polycondensed with various α,ω-alkylene diols via dehydration polymerization to afford a series of 3CML polyesters, P(3CMLm). • DFT calculations revealed that 3CML adopts a nonplanar structure due to the presence of a stereogenic center, leading to flexible polymer chains. • The thermal decomposition temperature (T d,5% ) of P(3CMLm) increased with increasing alkylene spacer length. • In BOD tests using surface and deep seawater, P(3CMLm) showed over 40% biodegradation after 54 days, attributable to hydrolysis under mildly alkaline conditions. Lignin has attracted considerable attention as an abundant natural carbon feedstock capable of replacing petroleum-based resources. Recent development in microbial funneling techniques has enabled the stable production of dibasic compounds as biometabolic intermediates such as 2-pyron-4,6-dicarboxylic acid ( PDC ) and (4 S )-3-carboxymuconolactone ( 3CML ) from lignin-derived aromatic molecules under controlled metabolic processes. Our group has demonstrated that PDC -incorporated polymers exhibit excellent heat resistance, mechanical performance, adhesive nature to metal and wood substrates, and biodegradability in simulated natural environments. In this study, a series of 3CML -based polyesters was synthesized by dehydrated polycondensation with diol compounds containing various alkyl spacer lengths. The resulting polyesters displayed distinct macroscopic behavior and thermal properties compared with PDC -based analogues due to the nonplanar molecular structure arising from the asymmetric center in 3CML . Biodegradation tests of 3CML -based polyesters in both surface and deep seawater revealed biodegradation rates exceeding ca. 40% after 54 days, comparable to those of polyhydroxyalkanoates and polycaprolactone.
Authors
- Tsuyoshi Michinobu (ORCID: https://orcid.org/0000-0001-6948-1189)
- E. Masai
- M. Joshi
- Y. Suzuki
- Y. Otsuka
- N. Kamimura
- M. Fujita
- A. Isobe
- T. Araki
- Y. Jin
- K. Jimbo
Institutions
- Tokyo Institute of Technology (JP)
- Nagaoka University (JP)
- Forestry and Forest Products Research Institute (JP)
- Nagaoka University of Technology (JP)
Publication Details
- Journal
- Polymer Degradation and Stability
- Published
- 2026-04-22
- DOI
- https://doi.org/10.1016/j.polymdegradstab.2026.112159
- Primary Topic
- Lignin and Wood Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Fuji Seal Foundation
- Japan Society for the Promotion of Science
- Japan Science and Technology Agency