Sustainable One-Pot Synthesis and Polycondensation of a Levoglucosenone-Derived Cyclic Acetal Diol

The already described one-pot two-step hydration/reduction of levoglucosenone (LGO) into (1R,2S,5R)-6,8-dioxabicyclo­[3.2.1]­octane-2,4-diol (HO-LGOL) was improved by replacing 50 mol % of Et3N by 5 mol % of K3PO4, a more sustainable base. The sterically hindered diol was then subjected to polycondensations with aliphatic comonomers to prepare new bio-based polyesters that exhibit glass transition (T g) values between 12 and 54 °C and high thermal stability greater than 200 °C. Two different strategies were implemented to perform the polymerizations: (1) utilization of aliphatic diacyl chlorides, or (2) a method involving aliphatic diethyl esters in the presence of a metal catalyst. These methods were then subjected to life cycle assessment to study their environmental impacts.