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

Green, S. K., University of Massachusetts Amherst
Williams, C. L., Idaho National Lab
Dauenhauer, P. J., University of Massachusetts Amherst
Chang, C. C., University of Massachusetts Amherst
Fan, W., University of Massachusetts Amherst

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.


[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