Hydrolytic furan ring opening is exploited to open biobased furanic molecules into levulinic-like platform molecules. However, the occurrence of ring opening in furanic macromoleculesconsidered so far as a side reactionhas never been quantitatively assessed. Poly(furfuryl alcohol) (PFA) was chosen to highlight the concept that furan ring opening can be monitored during polymerization. Both oximation and 19 F NMR quantification methods were employed to address this issue. This investigation shows that a substantial quantity of carbonyl species is formed during the polymerization, thus introducing the concept of degree of open structure (DOS). Polymerization of furfuryl alcohol (FA) in a 50 wt % aqueous solution approximately doubles the fraction of structures that are openedleading up to 15% of opened furanic entities (i.e., ∼3.5 mmol of carbonyl per gram of PFA)compared to FA polymerization conducted without additional water. The DOS was observed to increase continuously throughout the polymerization. Finally, steric hindrance has a role in the accessibility of carbonyls in PFA.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.