(13a) Diels-Alder Cycloaddition of Methylfuran and Ethylene to Produce Renewable Toluene

The need for sustainable production of everyday materials in addition to market volatility of petroleum-based feedstocks has motivated research into the production of renewable aromatic chemicals from biomass. Diels-Alder cycloaddition of methylfuran (MF) and ethylene to produce toluene is a promising method of sustainably producing an important monomer for polyurethane products.  Similar to the production of p-xylene from dimethylfuran and ethylene, the MF/ethylene reaction likely proceeds via two steps: cycloaddition of MF and ethylene to produce a cycloadduct intermediate, and subsequent dehydration of the intermediate to form toluene [1,2].  This work focuses on experimentally analyzing the kinetics of the combined cycloaddition/dehydration chemistry, characterizing the effects of catalyst loading, and determining reaction orders with respect to MF, ethylene, and toluene.

References

[1]  Williams, C. L.; Chang, C.-chih; Do, P.; Nikbin, N.; Caratzoulas, S.; Vlachos, D. G.; Lobo, R. F.; Fan, W.; Dauenhauer, P. J. ACS Catalysis 2012, 2, 935-939

[2] N. Nikbin, P.T. Do, S. Caratzoulas, R.F. Lobo, P.J. Dauenhauer, D.G. Vlachos, "A DFT study of the acid-catalyzed conversion of 2,5-dimethylfuran and ethylene to p-xylene," Journal of Catalysis, 2013, 297, 35-43