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Selective Conversion of Cellulose to Hydroxymethylfurfural in Polar Aprotic Solvents
Author(s) -
Weingarten Ronen,
RodriguezBeuerman Alexandra,
Cao Fei,
Luterbacher Jeremy S.,
Alonso David Martin,
Dumesic James A.,
Huber George W.
Publication year - 2014
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201402299
Subject(s) - levulinic acid , cellulose , chemistry , ionic liquid , yield (engineering) , levoglucosan , formic acid , solvent , organic chemistry , decomposition , hydroxymethylfurfural , dehydration , 5 hydroxymethylfurfural , furfural , catalysis , materials science , biochemistry , aerosol , biomass burning , metallurgy
Abstract Herein, we report a new reaction pathway to produce hydroxymethylfurfural (HMF) from cellulose under mild reaction conditions (140–190 °C; 5 m M H 2 SO 4 ) in polar aprotic solvents (i.e. THF) without the presence of water. In this system, levoglucosan is the major decomposition product of cellulose, followed by dehydration to produce HMF. Glucose, levulinic acid, and formic acid are also produced as a result of side reactions with water, which is a by‐product of dehydration. The turnover frequency for cellulose conversion increases as the water content in the solvent decreases, with conversion rates in THF being more than twenty times higher than those in water. The highest HMF yield from cellulose was 44 % and the highest combined yield of HMF and levulinic from cellulose was 53 %, which are nearly comparable to yields obtained in ionic liquids or biphasic systems. Moreover, the use of a low boiling point solvent, such as THF, facilitates recovery of HMF in downstream processes.