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Ring-opening metathesis polymerization of biomass-derived levoglucosenol

: Debsharma, Tapas; Behrendt, Felix N.; Laschewsky, Andre; Schlaad, Helmut


Angewandte Chemie. International edition 58 (2019), Nr.20, S.6718-6721
ISSN: 1433-7851
ISSN: 0044-8249
ISSN: 0570-0833
ISSN: 1521-3773
Fraunhofer IAP ()
degradable polymer; olefin metathesis; ring-opening polymerization; sustainable chemistry; thermoplastic

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.