Diethers of 5-(hydroxymethyl)furfural (HMF) are attractive fuel additives because of their high energy densities and advantageous fuel blending properties. In this presentation, we will show how Hf-, Zr- and Sn-Beta zeolites effectively catalyze the coupled transfer hydrogenation and etherification of HMF with primary and secondary alcohols, thus making it possible to generate 2,5-bis(alkoxymethyl)furans without the use of external hydrogen sources or precious metals.We will demonstrate that the use of flow reactor systems not only permits continuous operation but also facilitates a more thorough assessment of the stability of the Lewis acid zeolites. Our experiments reveal non-uniform changes in the relative deactivation rates of the transfer hydrogenation and etherification reactions, which impact the observed product distribution over time. We found that the catalysts undergo a deactivation for the etherification step while maintaining catalytic activity for the transfer hydrogenation step. 119Sn and 29Si MAS NMR studies show that this deactivation can be attributed to changes in the local environment of the metal sites. Additional insights were gained by studying effects of various alcohols and water concentration on the catalytic reactivity.

Continuous-flow synthesis of fuel additives from 5-(hydroxymethyl)furfural

248th National Meeting (2014)

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