Universal kinetic solvent effects in acid-catalyzed reactions of biomass-derived oxygenates

Walker, Theodore W.; Chew, Alex K.; Li, Huixiang; Demir, Benginur; Zhang, Z. Conrad; Huber, George W.; Van Lehn, Reid C.; Dumesic, James A.

doi:10.1039/C7EE03432F

Title: Universal kinetic solvent effects in acid-catalyzed reactions of biomass-derived oxygenates

Journal Article · Thu Feb 08 00:00:00 EST 2018 · Energy & Environmental Science

DOI:https://doi.org/10.1039/C7EE03432F· OSTI ID:1475402

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Univ. of Wisconsin, Madison, WI (United States). Dept. of Chemical and Biological Engineering
Chinese Academy of Sciences (CAS), Dalian (China). Dalian National Lab. for Clean Energy. Dalian Inst. of Chemical Physics; Univ. of Chinese Academy of Sciences, Beijing (China)
Univ. of Wisconsin, Madison, WI (United States). Dept. of Chemical and Biological Engineering. DOE Great Lakes Bioenergy Research Center
Chinese Academy of Sciences (CAS), Dalian (China). Dalian National Lab. for Clean Energy. Dalian Inst. of Chemical Physics

In this paper, the rates of Brønsted-acid-catalyzed reactions of ethyl tert-butyl ether, tert-butanol, levoglucosan, 1,2-propanediol, fructose, cellobiose, and xylitol were measured in solvent mixtures of water with three polar aprotic cosolvents: γ-valerolactone; 1,4-dioxane; and tetrahydrofuran. As the water content of the solvent environment decreases, reactants with more hydroxyl groups have higher catalytic turnover rates for both hydrolysis and dehydration reactions. We present classical molecular dynamics simulations to explain these solvent effects in terms of three simulation-derived observables: (1) the extent of water enrichment in the local solvent domain of the reactant; (2) the average hydrogen bonding lifetime between water molecules and the reactant; and (3) the fraction of the reactant accessible surface area occupied by hydroxyl groups, all as a function of solvent composition. Finally, we develop a model, constituted by linear combinations of these three observables, that predicts experimentally determined rate constants as a function of solvent composition for the entire set of acid-catalyzed reactions.

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Research Organization:: Univ. of Wisconsin, Madison, WI (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE), Sustainable Transportation Office. Bioenergy Technologies Office (BETO); USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE Office of Science (SC), Biological and Environmental Research (BER); Wisconsin Alumni Research Foundation (United States); National Science Foundation (NSF)

Grant/Contract Number:: EE0006878; FC02-07ER64494; ACI-1548562

OSTI ID:: 1475402

Journal Information:: Energy & Environmental Science, Vol. 11, Issue 3; ISSN 1754-5692

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 107 works

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Title: Universal kinetic solvent effects in acid-catalyzed reactions of biomass-derived oxygenates

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