Issue 11, 2012

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

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

Supplementary files

Article information

Article type
Paper
Submitted
23 Jun 2012
Accepted
16 Aug 2012
First published
05 Sep 2012

Green Chem., 2012,14, 3087-3098

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements