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A Continuous Flow Strategy for the Coupled Transfer Hydrogenation and Etherification of 5‐(Hydroxymethyl)furfural using Lewis Acid Zeolites
Author(s) -
Lewis Jennifer D.,
Van de Vyver Stijn,
Crisci Anthony J.,
Gunther William R.,
Michaelis Vladimir K.,
Griffin Robert G.,
RománLeshkov Yuriy
Publication year - 2014
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201402100
Subject(s) - furfural , chemistry , catalysis , hydroxymethyl , product distribution , transfer hydrogenation , flow chemistry , reactivity (psychology) , organic chemistry , lewis acids and bases , magic angle spinning , chemical engineering , nuclear magnetic resonance spectroscopy , ruthenium , medicine , alternative medicine , pathology , engineering
Abstract Hf‐, Zr‐ and Sn‐Beta zeolites effectively catalyze the coupled transfer hydrogenation and etherification of 5‐(hydroxymethyl)furfural with primary and secondary alcohols into 2,5‐bis(alkoxymethyl)furans, thus making it possible to generate renewable fuel additives without the use of external hydrogen sources or precious metals. Continuous flow experiments reveal nonuniform 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 drastic deactivation for the etherification step while maintaining catalytic activity for the transfer hydrogenation step. 119 Sn and 29 Si magic angle spinning (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.