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Ionization of Cellobiose in Aqueous Alkali and the Mechanism of Cellulose Dissolution

Journal article
Authors E. Bialik
B. Stenqvist
Y. Fang
A. Ostlund
I. Furo
B. Lindman
M. Lund
Diana Bernin
Published in Journal of Physical Chemistry Letters
Volume 7
Issue 24
Pages 5044-5048
ISSN 1948-7185
Publication year 2016
Published at Swedish NMR Centre at Göteborg University
Pages 5044-5048
Language en
Links 10.1021/acs.jpclett.6b02346
Keywords electrophoretic nmr, chemical-shifts, solvents, charge, hydroxides, complexes, mixtures, binding, state
Subject categories Chemical Sciences


Cellulose, one of the most abundant renewable resources, is insoluble in most common solvents but dissolves in aqueous alkali under a narrow range of conditions. To elucidate the solubilization mechanism, we performed electrophoretic NMR on cellobiose, a subunit of cellulose, showing that cellobiose acts as an acid with two dissociation steps at pH 12 and 13.5. Chemical shift differences between cellobiose in NaOH and NaCl were estimated using 2D NMR and compared to DFT shift differences upon deprotonation. The dissociation steps are the deprotonation of the hemiacetal OH group and the deprotonation of one of four OH groups on the nonreducing anhydroglucose unit. MD simulations reveal that aggregation is suppressed upon charging cellulose chains in solution. Our findings strongly suggest that cellulose is to a large extent charged in concentrated aqueous alkali, a seemingly crucial factor for solubilization. This insight, overlooked in the current literature, is important for understanding cellulose dissolution and for synthesis of new sustainable materials.

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