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Issue 11, 2012
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Mediating acid-catalyzed conversion of levoglucosan into platform chemicals with various solvents

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Abstract

Acid-catalyzed conversions of levoglucosan have been investigated in mono-alcohols, poly-alcohols, water, chloroform, toluene, acetone, N,N-dimethyl formamide, dimethyl sulfoxide and some mixed solvents, aiming to mediate conversion of sugars into platform chemicals with solvents. The mono-alcohols can stabilize soluble polymers and thus suppress formation of insoluble polymers. Water does not have such an effect, leading to lower yields of levulinic acid. Chloroform cannot effectively dissolve levoglucosan, leading to “dissolving” of levoglucosan in the catalyst and the consequent rapid polymerization. Acetone reacted with sugars, forming substantial amounts of polymer. N,N-Dimethyl formamide poisoned the acid resin catalyst, leading to negligible conversion of levoglucosan. Dimethyl sulfoxide (DMSO) mainly catalyzed the conversion of levoglucosan into 5-(hydroxymethyl)furfural (HMF), 2,5-furandicarboxaldehyde, and the sulfur ether of HMF. DMSO has a low ability to transfer protons, which helps to avoid further contact of HMF with catalytic sites and stabilizes HMF.

Graphical abstract: Mediating acid-catalyzed conversion of levoglucosan into platform chemicals with various solvents

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Publication details

The article was received on 23 Jun 2012, accepted on 16 Aug 2012 and first published on 05 Sep 2012


Article type: Paper
DOI: 10.1039/C2GC35961H
Green Chem., 2012,14, 3087-3098

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    Mediating acid-catalyzed conversion of levoglucosan into platform chemicals with various solvents

    X. Hu, L. Wu, Y. Wang, D. Mourant, C. Lievens, R. Gunawan and C. Li, Green Chem., 2012, 14, 3087
    DOI: 10.1039/C2GC35961H

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