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Issue 1, 2013
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Organocatalytic conversion of cellulose into a platform chemical

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Abstract

The search for a source of fuels and chemicals that is both abundant and renewable has become of paramount importance. The polysaccharide cellulose meets both criteria, and methods have been developed for its transformation into the platform chemical 5-(hydroxymethyl)furfural (HMF). These methods typically employ harsh reaction conditions or toxic heavy metal catalysts, deterring large-scale implementation. Here, we describe a low-temperature, one-pot route that uses ortho-carboxyl-substituted phenylboronic acids as organocatalysts in conjunction with hydrated magnesium chloride and mineral acids to convert cellulose and cellulose-rich municipal waste to HMF in yields comparable to processes that use toxic heavy metal catalysts. Isotopic labeling studies indicate that the key aldose-to-ketose transformation occurs via an enediol intermediate. The route, which also allows for facile catalyst recovery and recycling, provides a green prototype for cellulose conversion.

Graphical abstract: Organocatalytic conversion of cellulose into a platform chemical

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Article information


Submitted
01 Sep 2012
Accepted
02 Oct 2012
First published
03 Oct 2012

Chem. Sci., 2013,4, 196-199
Article type
Edge Article

Organocatalytic conversion of cellulose into a platform chemical

B. R. Caes, M. J. Palte and R. T. Raines, Chem. Sci., 2013, 4, 196
DOI: 10.1039/C2SC21403B

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