Green Synthesis of UV-Reactive Polycarbonates from Levoglucosenone and 5-Hydroxymethyl Furfural

This study focuses on the synthesis of fully renewable polycarbonates (PCs) starting from cellulose-based platform molecules levoglucosenone (LGO) and 2,5-bis(hydroxymethyl)furan (BHMF). These unique bio-based PCs are obtained through the reaction of a citronellol-containing triol (Triol-citro) derived from LGO, with a dimethyl carbonate derivative of BHMF (BHMF-DC). Solvent-free polymerizations are targeted to minimize waste generation and promote an eco-friendly approach with a favorable environmental factor (E-factor). The choice of metal catalyst during polymerization significantly influences the polymer properties, resulting in high molecular weight (up to 755 kDa) when Na2CO3 is employed as an inexpensive catalyst. Characterization using nuclear magnetic resonance confirms the successful incorporation of the furan ring and the retention of the terminal double bond of the citronellol pendant chain. Furthermore, under UV irradiation, the presence of both citronellol and furanic moieties induces singular structural changes, triggering the formation of three distinct structures within the polymer network, a phenomenon herein occurs for the first time in this type of polymer. These findings pave the way to new functional materials prepared from renewable monomers with tunable properties. This study explores the synthesis of renewable polycarbonates using both levoglucosenone and 5-hydroxymethyl furfural as renewable platform molecules. A solvent-free polymerization approach with a low E-factor is detailed. The influence of metal catalysts on polymer properties is examined, with Na2CO3 yielding a high molecular weight of 755 kDa. UV irradiation induces unique structural changes within the polymer network.image

Automated summary

This study focuses on the synthesis of fully renewable polycarbonates using cellulose-based platform molecules. A solvent-free polymerization approach is utilized to obtain unique bio-based polycarbonates with high molecular weight and structural changes, paving the way for the development of functional materials with tunable properties.