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Novel high reactive bifunctional five- and six-membered bicyclic dicarbonate – synthesis and characterisation

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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… Click to show full 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.

Keywords: novel high; dicarbonate; six membered; synthesis; five six; membered bicyclic

Journal Title: RSC Advances
Year Published: 2018

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