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

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

doi:10.1039/C7GC01688C

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

Journal Article · Thu Jun 22 00:00:00 EDT 2017 · Green Chemistry

DOI:https://doi.org/10.1039/C7GC01688C· OSTI ID:1475401

^[1]; Liu, Mingjie ^[2]; ^[2]; Walker, Theodore W. ^[2]; ^[2]; Dumesic, James A. ^[2]; ^[2]

Univ. of Wisconsin, Madison, WI (United States). Dept. of Chemical and Biological Engineering; University of Wisconsin-Madison Department of Chemical and Biological Engineering
Univ. of Wisconsin, Madison, WI (United States). Dept. of Chemical and Biological Engineering

In this paper, 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. Finally, 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.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of Wisconsin, Madison, WI (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE), Bioenergy Technologies Office (EE-3B)

Grant/Contract Number:: EE0006878

OSTI ID:: 1475401

Journal Information:: Green Chemistry, Journal Name: Green Chemistry Journal Issue: 15 Vol. 19; ISSN 1463-9262

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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