Abstract
Five- and six-membered bicyclic carbonates are valuable raw materials for the synthesis of environmentally friendly polymers, such as polycarbonates or non-isocyanate poly(hydroxyurethane)s. However, bicyclic diglycerol dicarbonates bearing five-membered and six-membered rings have been never reported before. In this work, for the first time, we report a simple procedure for the synthesis of this monomer from commercially available diglycerol. The product was characterised by 1H NMR, 13C NMR, FTIR spectroscopy and X-ray diffraction measurements. Next, the reactivity of the obtained bicyclic carbonate was investigated. The obtained diglycerol dicarbonate was used as a monomer for polycarbonate and non-isocyanate poly(hydroxyurethane) based on putrescine. In the homopolymerisation reaction the opening of the six-membered carbonate ring was observed, while in the polycondensation with diamine both carbonate rings open nonselectively.
Highlights
Five- and six-membered bicyclic carbonates are raw materials for the synthesis of polycarbonates or non-isocyanates poly(hydroxyurethane)s via environmentally friendly routes
In our previous work we demonstrated a one-step procedure for the synthesis of vemembered bicyclic diglycerol dicarbonate as a raw material for PHUs.[8]
The reaction residue may be used as a substrate for the synthesis of the ve- and six-membered diglycerol dicarbonate
Summary
Five- and six-membered bicyclic carbonates are raw materials for the synthesis of polycarbonates or non-isocyanates poly(hydroxyurethane)s via environmentally friendly routes. Bifunctional bicyclic dicarbonate bearing ve-membered and six-membered carbonate rings have already been presented in the literature.[21,22] He et al synthesised in a multistep reaction from trimethylolpropane and used a monomer for poly(hydroxyurethane)s, PHUs, synthesis.[21] Endo et al presented anionic polymerisation of bifunctional cyclic carbonate consisting of both ve- and six-membered rings obtained in a multistep procedure.[22] The obtained a,b-diglycerol dicarbonate was used as a monomer for polycarbonate and poly(hydroxyurethane)s base on putrescine (see Scheme 1).
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