Synthesis and Applications of Dialdehydes

Abstract

Due to their reactivity and ease of functional group interconversions, aldehydes have wide-ranging applications in polymer synthesis, such as polyacetals, epoxy resins, and polyurethanes. Recently, room temperature synthesis of polycarbamates using cyclohexanedicarboxaldehydes was reported by Dow Chemical, thus opening up a novel way of making non-isocyanate polyurethanes (NIPUs) with greater applicability. However, preparing NIPUs is limited by the available bio-based dialdehydes. Therefore, we prepared a series of bio-derived bis-furan and tris-furan dialdehydes through the condensation of furan with four readily available ketones, with subsequent formylation via the Vilsmeier-Haack reaction. The incorporation of structurally different spacers in otherwise structurally similar dialdehyde monomers resulted in a variety of melting points dependent on the relative symmetry and rigidity of the structures. Chapter 1 addresses the synthesis of aldehydes with a review of their current utility in polymer synthesis. Chapter 2 addresses our synthesis of the dialdehydes and their potential applications in polymer synthesis.