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Selective Production of Renewable para ‐Xylene by Tungsten Carbide Catalyzed Atom‐Economic Cascade Reactions
Author(s) -
Dai Tao,
Li Changzhi,
Li Lin,
Zhao Zongbao Kent,
Zhang Bo,
Cong Yu,
Wang Aiqin
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201710074
Subject(s) - hydrodeoxygenation , chemistry , catalysis , intramolecular force , cyclohexene , atom economy , deoxygenation , dehydrogenation , photochemistry , organic chemistry , selectivity
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 W 2 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.