Production of levoglucosenone and 5-hydroxymethylfurfural from cellulose in polar aprotic solvent-water mixtures

Jiayue He, Mingjie Liu, Kefeng Huang, Theodore W. Walker, Christos T. Maravelias, James A. Dumesic, George W. Huber

Research output: Contribution to journalArticlepeer-review

69 Scopus citations

Abstract

We demonstrate a process to produce levoglucosenone (LGO) and 5-hydroxymethylfurfural (HMF) from cellulose in up to 65% carbon yield using sulfuric acid as catalyst and a solvent consisting of a mixture of tetrahydrofuran (THF) with water. In pure THF, LGO is the major product of cellulose dehydration, passing through levoglucosan as an intermediate. Increasing the water content (up to 5 wt%) results in HMF as the major product. HMF is formed both by glucose dehydration and direct dehydration of LGA. The maximum combined yield of LGO and HMF (∼65 carbon%) is achieved in the presence of 1-2.5 wt% H2O, such that comparable amounts of these two co-products are formed. THF gave the highest total yields of LGO and HMF among the solvents investigated in this study (i.e., THF, diglyme, tetraglyme, gamma-valerolactone (GVL), cyclopentyl methyl ether (CPME), 1,4-dioxane, and dimethyl sulfoxide (DMSO)). Furthermore, the rate of LGO and HMF degradation in THF was lower than in the other solvents. LGO/HMF yields increased with increased strength of the acid catalyst (H2SO4 > H3PO4 > HCOOH), and HMF was produced more selectively than LGO in the presence of hydrochloric acid. Techno-economic analysis for LGO and HMF production from cellulose shows that the lowest LGO/HMF production costs are less than $3.00 per kg and occur at a cellulose loading and water content of 2-3% and 1.5-2.5% respectively.

Original languageEnglish (US)
Pages (from-to)3642-3653
Number of pages12
JournalGreen Chemistry
Volume19
Issue number15
DOIs
StatePublished - 2017
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Environmental Chemistry
  • Pollution

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