Kinetics of Diels-Alder Reaction Using Organic Molecular Models

Abstract

To synthesize biopolymers with specific biodegradability and water solubility properties through the Diels-Alder and retro-Diels-Alder reactions, model molecules such as tri-(1-ethyl-pyrrole-2,5-dione) amine, exo-3,6-epoxy anhydride-1,2,3,6-tetrahydrophthalic, and bismaleimide were designed. The Diels-Alder cycloaddition was envisioned as a strategy to develop polymeric materials with potential self-healing, recyclability, and thermal reversibility properties. These polymers serve as carriers for active compounds.

NMR spectroscopy, including ¹H NMR and ¹³C NMR, was employed to elucidate the structural characteristics of the synthesized compounds. The progress of the Diels-Alder reaction over time at room temperature and at 40°C between furan and 1,1'-(Methylenedi-4,1-phenylene)bismaleimide (commercial bismaleimide) was monitored using ¹H NMR spectroscopy. Conversion rates of 95% at 40°C and 87% at 25°C were achieved after 16 hours.