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Solvent Effects in Acid‐Catalyzed Biomass Conversion Reactions
Author(s) -
Mellmer Max A.,
Sener Canan,
Gallo Jean Marcel R.,
Luterbacher Jeremy S.,
Alonso David Martin,
Dumesic James A.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201408359
Subject(s) - chemistry , catalysis , kinetics , solvent , brønsted–lowry acid–base theory , levulinic acid , acid catalysis , xylose , furfural , organic chemistry , selectivity , dimethoxymethane , solvent effects , hydrolysis , physics , quantum mechanics , fermentation
Reaction kinetics were studied to quantify the effects of polar aprotic organic solvents on the acid‐catalyzed conversion of xylose into furfural. A solvent of particular importance is γ‐valerolactone (GVL), which leads to significant increases in reaction rates compared to water in addition to increased product selectivity. GVL has similar effects on the kinetics for the dehydration of 1,2‐propanediol to propanal and for the hydrolysis of cellobiose to glucose. Based on results obtained for homogeneous Brønsted acid catalysts that span a range of p K a values, we suggest that an aprotic organic solvent affects the reaction kinetics by changing the stabilization of the acidic proton relative to the protonated transition state. This same behavior is displayed by strong solid Brønsted acid catalysts, such as H‐mordenite and H‐beta.