Enantioselective Crystallization of Diglycerol Dicarbonate: Impact of the Microstructure on Polyhydroxyurethane Properties

Bicylic carbonates are precursors employed in non-isocyanate polyurethane syntheses, namely polyhydroxyurethanes (PHUs) and, among them, ether-activated biobased diglycerol dicarbonate (DGDC) is widely investigated. Herein, the original separation of DGDC stereoisomers, thanks to a recrystallization procedure, leading to enantiomers having different crystal lattices, that is, square transparent crystals and needle-like structures, respectively, is reported. In this study, the separation and the characterization of the two crystal structures is first discussed and, second, the impact of the stereochemistry of DGDC on the corresponding PHUs properties is investigated.