Synthesis and characterization of highly substituted deoxyfluorocellulose acetate

Deoxyfluorocellulose acetates were prepared from cellulose acetate (CA, degree of substitution by acetyl groups: 2.2 and 1.7) by using diethylaminosulfur trifluoride (DAST) in 1,4-dioxane or diglyme. The maximum degree of substitution of fluorine of the products was approximately 0.60, and depolymerization was not significant during fluorination. The replacement of hydroxyl groups by fluorine atoms occurred exclusively at C-6, as confirmed by carbon-13 NMR spectroscopy. In the presence of pyridine, an N-pyridinium derivative of CA was obtained instead of a deoxyfluoro derivative of cellulose.