275784 Renewable Catalytic Process for the Production of p-Xylene From Glucose

Wednesday, October 31, 2012: 10:30 AM
321 (Convention Center )
Paul J. Dauenhauer, Department of Chemical Engineering, University of Massachusetts-Amherst, Amherst, MA, Raul F. Lobo, Chemical Engineering, University of Delaware, Newark, DE, Dionisios G. Vlachos, Catalysis Center for Energy Innovation, Chemical and Biomolecular Engineering, University of Delaware, Newark, DE and Wei Fan, Department of Chemical Engineering, University of Massachusetts Amherst, Amherst, MA

A renewable process to p-xylene from biomass-derived sugars provides a new method for sustainable production of plastics including PET [1].  As part of the Catalysis Center for Energy Innovation (CCEI), we demonstrate a three step process: (1) conversion of glucose to 5-hydroxymethylfurfural, (2) hydrodeoxygenation to dimethylfuran, and (3) cycloaddition of dimethylfuran to p-xylene.  This route introduces the possibility for utilizing sugars produced from the saccharification of biopolymers such as cellulose [2].  Initial dehydration of fructose produces an oxygenated furan, which is subsequently reduced to dimethylfuran.  The following reaction to produce p-xylene occurs within a single reactor as a two-part reaction (Diels-Alder cycloaddition followed by dehydration).  This reaction occurs through an oxygenated bicyclic intermediate, which can lead to the desired product of p-xylene or to undesireable dimer side products.  Additionally, dehydration to produce p-xylene produces water which can hydrolyze dimethylfuran and produce ring-opened six-carbon side products.  Through insight into the role catalyst structure and active site, we have designed a catalytic system capable of achieving 75% yield of p-xylene [3].

References:

[1] Climent, M. J.; Corma, A.; Iborra, S. Green Chemistry 2011, 13, 520-540

[2] Vlachos, D. G.; Chen, J. G.; Gorte, R. J.; Huber, G. W.; Tsapatsis, M. Catalysis Letters 2010, 140, 77-84.

[3] 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


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