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

Xun Hu, Liping Wu, Yi Wang, Daniel Mourant, Caroline Lievens, Richard Gunawan, Chun Zhu Li*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

64 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)3087-3098
Number of pages12
JournalGreen chemistry
Volume14
Issue number11
DOIs
Publication statusPublished - 1 Nov 2012
Externally publishedYes

Keywords

  • ITC-ISI-JOURNAL-ARTICLE

Fingerprint Dive into the research topics of 'Mediating acid-catalyzed conversion of levoglucosan into platform chemicals with various solvents'. Together they form a unique fingerprint.

Cite this