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Ring‐Opening Metathesis Polymerization of Biomass‐Derived Levoglucosenol
Author(s) -
Debsharma Tapas,
Behrendt Felix N.,
Laschewsky André,
Schlaad Helmut
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201814501
Subject(s) - molar mass , polymerization , ring opening metathesis polymerisation , romp , polymer chemistry , olefin metathesis , metathesis , yield (engineering) , ring opening polymerization , glass transition , chemistry , degree of polymerization , cellulose , cationic polymerization , living polymerization , catalysis , materials science , organic chemistry , polymer , radical polymerization , composite material
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.