T. Debsharma, F. N. Behrendt, A. Laschewsky, H. Schlaad
Ring-Opening Metathesis Polymerization of Biomass-Derived Levoglucosenol
Angew. Chem. Int. Ed. 2019, 58, 6718-6721
DOI: 10.1002/anie.201814501
The readily available cellulose-derived bicyclic compound levoglucosenol was polymerized through ring-opening metathesis polymerization (ROMP) to yield polylevoglucosenol as a novel type of biomass-derived thermoplastic polyacetal, which, unlike polysaccharides, contains cyclic as well as linear segments in its main chain. High-molar-mass polyacetals with apparent weight-average molar masses of up to 100 kg/mol-1 and dispersities of approximately 2 were produced despite the non-living/controlled character of the polymerization due to irreversible deactivation or termination of the catalyst/active chain ends. The resulting highly functionalized polyacetals are glassy in bulk with a glass transition temperature of around 100°C. In analogy to polysaccharides, polylevoglucosenol degrades slowly in an acidic environment.
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