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Synthesis 2011(11): 1649-1677  
DOI: 10.1055/s-0030-1260008
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Catalytic One-Pot Production of Small Organics from Polysaccharides

J. Johan Verendela, Tamara L. Churcha, Pher G. Andersson*a,b
a Department of Biochemistry and Organic Chemistry, Uppsala University, Box 576, 75123 Uppsala, Sweden
b School of Chemistry, University of KwaZulu-Natal, Durban, South Africa
Fax: +46(18)4713818; e-Mail: pher.andersson@biorg.uu.se;
Further Information

Publication History

Received 17 November 2010
Publication Date:
19 April 2011 (online)

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Abstract

The catalytic techniques that degrade polysaccharides such as cellulose and elaborate the resulting monomers into organic feedstocks in situ make up an old area of research that has been reignited of late. One-pot conversions of polysaccharides into small organic molecules under acidic, basic, oxidative, reductive and hydrothermal conditions have been reported, and a remarkable breadth of compounds have been produced. 5-Hydroxymethylfurfural (HMF), levulinic acid and polyols such as sorbitol have been obtained in particularly high yields, whereas serious selectivity struggles remain in reactions that produce organic acids such as lactic or glycolic acid. This review covers one-pot, catalytic transformations of polysaccharides into small organic molecules and focuses on mechanism, selectivity and optimization.

1 Introduction

1.1 Scope and Related Topics

1.2 A Note on Yield

2 Acid-Catalyzed Processes

2.1 Hydrolysis to Monosaccharides

2.1.1 Decomposition of Sugars in Hot, Dilute Acid

2.2 Selective Formation of Furan-2-aldehydes

2.3 Selective Formation of Levulinic Acid

3 Trapping of Monosaccharides by Chemical Modification

3.1 Formation of Alkyl Glucosides

3.2 Formation of Polyols

4 Alkaline Hydrolysis

4.1 Cellulose Conversion

4.2 Product Selectivity

5 Hydrothermal Degradation

6 Metal-Catalyzed Oxidative Degradation

7 Conclusion and Outlook

Key words

catalysis - green chemistry - polysaccharides - renewable feedstocks - cellulose

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