Ring-Opening Metathesis Polymerization of Biomass-Derived Levoglucosenol

Angew Chem Int Ed Engl. 2019 May 13;58(20):6718-6721. doi: 10.1002/anie.201814501. Epub 2019 Apr 4.

Abstract

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.

Keywords: degradable polymers; metathesis; ring-opening polymerization; sustainable chemistry; thermoplastics.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biomass*
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry*
  • Glucose / analogs & derivatives*
  • Glucose / chemistry
  • Humans
  • Molecular Structure
  • Polymerization*

Substances

  • Bridged Bicyclo Compounds, Heterocyclic
  • 1,6-anhydro-3,4-dideoxyhex-3-enopyran-2-ulose
  • Glucose