Ring opening polymerization of β-acetoxy-δ-methylvalerolactone, a triacetic acid lactone derivative?

Polymer Chemistry Pub Date: 2021-11-14 DOI: 10.1039/D1PY00561H

Abstract

We report here the synthesis and polymerization of a novel disubstituted valerolactone, β-acetoxy-δ-methylvalerolactone, derived from the renewable feedstock triacetic acid lactone (TAL). The bulk polymerization proceeds to 45% equilibrium monomer conversion at room temperature using diphenyl phosphate as the organic catalyst. The resultant amorphous material displays a glass transition temperature of 25 °C. The ring opening polymerization (ROP) behavior of the disubstituted valerolactone was examined, and the enthalpy (Image ID:d1py00561h-t1.gif) and entropy *(Image ID:d1py00561h-t2.gif) of polymerization were calculated to be ?25 ± 2 kJ mol?1 and ?81 ± 5 mol?1 K?1, respectively. The polymerization kinetics were also measured and compared to those of other substituted valerolactones reported in the literature. This report is the first to demonstrate the successful ROP of a disubstituted valerolactone as well as the first to establish the ROP of a derivative of TAL.

Graphical abstract: Ring opening polymerization of β-acetoxy-δ-methylvalerolactone, a triacetic acid lactone derivative
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