470117 Production of Terephthalate Esters Via Diels-Alder Cycloaddition-Dehydration Reactions of 1,2-Furandicarboxylate Esters and Ethylene
Recently, we have reported on the synthesis and characterization of Zn Lewis acid sites in CIT-6 (Zn-Beta).4 We showed that, in addition to enabling DA reactions of MMFC, CIT-6 is able to react the dimethyl ester of FDCA (DMFDC). However, in the latter case, catalysis of decarboxylation reactions of the furan compromised selectivity towards the diester aromatic products, with the highest selectivity of 36%.
Here, we report a set of microporous catalysts for such DA reactions that do not appear to promote decarboxylation of DMFDC, and the optimization of reaction conditions that enables terephthalate diester selectivities upwards of 88%.
(1) Chang, C.-C.; Je Cho, H.; Yu, J.; Gorte, R. J.; Gulbinski, J.; Dauenhauer, P.; Fan, W. Green Chem. 2015.
(2) Pacheco, J. J.; Davis, M. E. Proc. Natl. Acad. Sci. U. S. A. 2014, 111(23), 8363–8367.
(3) Pacheco, J. J. New Catalysts for the Renewable Production of Monomers for Bioplastics, PhD Dissertation, California Institute of Technology, 2015.
(4) Orazov, M.; Davis, M. E. Chem. Sci. 2016, 7(3), 2264–2274.
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