Effect of substituents and promoters on the Diels-Alder cycloaddition reaction in the biorenewable synthesis of trimellitic acid.

An efficient route to produce oxanorbornene, a precursor for the production of bio-based trimellitic acid (TMLA) the Diels-Alder (DA) reaction of biomass-derived dienes and dienophiles has been proposed by utilizing density functional theory (DFT) simulations. It has been suggested that DA reaction of dienes such as 5-hydroxymethyl furfural (HMF), 2,5-dimethylfuran (DMF), furan dicarboxylic acid (FDCA) and biomass-derived dienophiles (ethylene derivatives , acrolein, acrylic acid, ) leads to the formation of an intermediate product oxanorbornene, a precursor for the production of TMLA. The activation barriers for the DA reaction were correlated to the type of substituent present on the dienes and dienophiles.