Hydrolysis of Lignin α‑O‑4 Model Compounds Using Strong Acid Catalyst in Water
- 1Gifu University , , 1-1, Yanagido , ,
- 2Gifu University , , 1-1 Yanagido , ,
Abstract
Efficient and sustainable cleavage of α-O-4 ether linkages is a critical initial step in lignin valorization. In this study, we present two highly effective catalytic protocols for the cleavage of C–O bonds in lignin α-O-4 model compounds under mild conditions (100 °C) that do not require organic solvents. Benzyl phenyl ether and its derivatives undergo quantitative conversion at 100 °C in the absence of an organic solvent under two contrasting conditions: aqueous trifluoromethanesulfonic acid (TfOH) yields the hydrolysis products phenol and benzyl alcohol, whereas solid superacid Nafion NR50 yields benzyl-migrated recombination products predominantly under solvent-free conditions. Nafion NR50 was recovered and reused for five consecutive cycles with conversion maintained within experimental error of activity. Non-fluorinated resins undergo the same transformation more slowly, which suggests that a perfluorinated acid is unnecessary. The medium-control principle established here defines the conditions under which condensation can be suppressed during acid-mediated α-O-4 cleavage.
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BibTeX
@article{mizuno2026hydrolysis,
title = {{Hydrolysis of Lignin α‑O‑4 Model Compounds Using Strong Acid Catalyst in Water}},
author = {Shota Mizuno and Koshiro Yamaguchi and Yasuhiro Kubota and Toshiyasu Inuzuka and Kazumasa Funabiki},
journal = {ACS omega},
year = {2026},
month = oct,
doi = {10.1021/acsomega.6c05568},
url = {https://europepmc.org/article/PMC/PMC13670879},
note = {CC BY-NC-ND},
}
RIS
TY - JOUR
TI - Hydrolysis of Lignin α‑O‑4 Model Compounds Using Strong Acid Catalyst in Water
AU - Shota Mizuno
AU - Koshiro Yamaguchi
AU - Yasuhiro Kubota
AU - Toshiyasu Inuzuka
AU - Kazumasa Funabiki
PY - 2026
DA - 2026/10/01
JO - ACS omega
DO - 10.1021/acsomega.6c05568
UR - https://europepmc.org/article/PMC/PMC13670879
AB - Efficient and sustainable cleavage of α-O-4 ether linkages is a critical initial step in lignin valorization. In this study, we present two highly effective catalytic protocols for the cleavage of C–O bonds in lignin α-O-4 model compounds under mild conditions (100 °C) that do not require organic solvents. Benzyl phenyl ether and its derivatives undergo quantitative conversion at 100 °C in the absence of an organic solvent under two contrasting conditions: aqueous trifluoromethanesulfonic acid (TfOH) yields the hydrolysis products phenol and benzyl alcohol, whereas solid superacid Nafion NR50 yields benzyl-migrated recombination products predominantly under solvent-free conditions. Nafion NR50 was recovered and reused for five consecutive cycles with conversion maintained within experimental error of activity. Non-fluorinated resins undergo the same transformation more slowly, which suggests that a perfluorinated acid is unnecessary. The medium-control principle established here defines the conditions under which condensation can be suppressed during acid-mediated α-O-4 cleavage.
SN - 2470-1343
ER -