Biocatalytic and solvent-free synthesis of a bio-based biscyclocarbonate

Abstract

A biocatalytic synthesis of sebacic biscyclocarbonate has been developed. Sebacic biscyclocarbonate is a monomer for non-isocyanate polyurethane (NIPU) synthesis. The synthesis was performed in neat glycerol carbonate in the presence of lipase B from Candida antarctica (CalB immo Plus). The bifunctional molecule was synthesized directly from the bio-based reactants sebacic acid and glycerol carbonate, a product of glycerol. The optimization of reaction conditions in terms of reaction time and temperature revealed a temperature optimum at room temperature in contrast to the activity optimum of the lipase. NMR analysis was used to investigate the dominant competing reactions and the mechanism of selectivity at the optimized reaction parameters. ¹H- and ¹³C-NMR as well as mass spectrometry confirm that sebacic biscyclocarbonate can be synthesized in the highest purity by the optimized process.