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Issue 1, 2013
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Functional group dependence of the acid catalyzed ring opening of biomass derived furan rings: an experimental and theoretical study

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Abstract

We describe studies of Brønsted acid catalyzed ring opening of substituted furans contained within biomass derived C8- and C9-molecules. Ring opening occurs homogeneously under relatively mild conditions of 80 °C using catalytic hydrochloric acid. In the case of 4-(5-methyl-2-furyl)-2-butanone (1a), the reaction proceeds to a single product in up to 92% yield after 24 hours. For 4-(2-furanyl)-2-butanone (1b) and 4-(5-hydroxymethyl)-2-furanyl-2-butanone (1c), however, multiple products are observed, illustrating the significant influence of furan ring substituents on the reactivity of this class of compounds. The generality of these reaction pathways was tested using several other similar substrates. Kinetics experiments indicate that ring opening of 1a occurs via specific acid catalysis, and computations elucidate the effect of initial protonation on the reaction pathway. Calculated pKa values were calibrated against experimentally measured values and are consistent with observed reactivities. Inclusion of explicit, hydrogen-bonded water molecules in addition to the SMD solvent model is necessary when studying protonation of alcohol and ketone groups.

Graphical abstract: Functional group dependence of the acid catalyzed ring opening of biomass derived furan rings: an experimental and theoretical study

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Article information


Submitted
10 Jun 2012
Accepted
04 Jul 2012
First published
26 Jul 2012

Catal. Sci. Technol., 2013,3, 106-115
Article type
Paper

Functional group dependence of the acid catalyzed ring opening of biomass derived furan rings: an experimental and theoretical study

C. R. Waidmann, A. W. Pierpont, E. R. Batista, J. C. Gordon, R. L. Martin, L. A. “Pete” Silks, R. M. West and R. Wu, Catal. Sci. Technol., 2013, 3, 106
DOI: 10.1039/C2CY20395B

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