Cellulose-based thermoplastic polyacetals

Abstract: Increasing concern about hazards of fossil-based chemicals including polymers motivates search for renewable alternatives. Cellulose is one of the most abundant renewable resources, consequently prompts its exploitation for the production of value-added chemicals. Levoglucosenone is one such chemical that is obtained from (waste) cellulose by pyrolysis. Levoglucosenone can easily and efficiently be converted into levoglucosenol and levoglucosenyl alkyl ethers. Levoglucosenol was polymerized by ring-opening metathesis polymerization (ROMP) to produce unsaturated polyacetals with molar masses of up to 100 kg/mol [1]. The polymers are amorphous with a glass transition temperature of ~100 °C and degrade slowly in acidic environment. Levoglucosenyl methyl ether was polymerized by cationic ring- opening polymerization (CROP) to give semi-crystalline unsaturated polyacetals with molar masses of up to 47 kg/mol [2]. These polyacetals can be further modified by hydrogenation and thiol-ene addition as well as by cross-linking.

Literature:

[1] T. Debsharma, F. N. Behrendt, A. Laschewsky, H. Schlaad, Angew. Chem. Int. Ed. 2019, 58, 6718-6721.

[2] T. Debsharma, Y. Yagci, H. Schlaad, Angew. Chem. Int. Ed. 2019, 58, 18492-18495.