Selective Production of Renewable para-Xylene by Tungsten Carbide Catalyzed Atom-Economic Cascade Reactions.

Author(s) Dai, T.; Li, C.; Li, L.; Zhao, Z.Kent; Zhang, B.; Cong, Y.; Wang, A.
Journal Angew Chem Int Ed Engl
Date Published 2018 Feb 12
Abstract

Tungsten carbide was employed as the catalyst in an atom-economic and renewable synthesis of para-xylene with excellent selectivity and yield from 4-methyl-3-cyclohexene-1-carbonylaldehyde (4-MCHCA). This intermediate is the product of the Diels-Alder reaction between the two readily available bio-based building blocks acrolein and isoprene. Our results suggest that 4-MCHCA undergoes a novel dehydroaromatization-hydrodeoxygenation cascade process by intramolecular hydrogen transfer that does not involve an external hydrogen source, and that the hydrodeoxygenation occurs through the direct dissociation of the C=O bond on the W2 C surface. Notably, this process is readily applicable to the synthesis of various (multi)methylated arenes from bio-based building blocks, thus potentially providing a petroleum-independent solution to valuable aromatic compounds.

DOI 10.1002/anie.201710074
ISSN 1521-3773
Citation Dai T, Li C, Li L, Zhao ZK, Zhang B, Cong Y, et al. Selective Production of Renewable para-Xylene by Tungsten Carbide Catalyzed Atom-Economic Cascade Reactions. Angew Chem Int Ed Engl. 2018;57(7):1808-1812.

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