Origin of 5-Hydroxymethylfurfural Stability in Water/Dimethyl Sulfoxide Mixtures

Authors


Abstract

Invited for this month′s cover is the Catalysis Center for Energy Innovation at the University of Delaware. The image shows the synergy of first principles calculations with vibrational spectroscopy to elucidate the stability of 5-hydroxymethylfurfural (HMF) in DMSO/water mixtures. The Full Paper itself is available on page 117 (10.1002/cssc.201300786).

What prompted you to investigate this topic?

12345Hexose dehydration to 5-hydroxymethylfurfural (HMF) is a key reaction for converting carbohydrates to fuels and chemicals, hampered by the low yields due to HMF degradation. It is well known that the utilization of some organic co-solvents, like DMSO, staves off undesired reactions. Elucidating the role of co-solvent in HMF stability contributes to the fundamental understanding of the chemistry and sets the foundations for rational solvent selection.

Scheme 1.

Dr. George Tsilomelekis

Scheme 2.

Tyler R. Josephson

Scheme 3.

Dr. Vladimiros Nikolakis

Scheme 4.

Dr. Stavros Caratzoulas

Scheme 5.

What is the most significant result of this study?

This study reveals the first experimental evidence of competitive and selective solvation of HMF carbonyl group by an aprotic solvent in the presence of water. This finding, in conjunction with the calculated effect of DMSO on HMF LUMO energy, can explain the enhanced stability of HMF toward degradation reactions when some organic co-solvents are used.

Is your current research mainly curiosity-driven (fundamental) or rather applied?

Our research is primarily driven by the need to advance the underlying fundamental science needed for the development, efficient design, and operation of the future biorefinery.

Acknowledgements

The work was financially supported by the Catalysis Center for Energy Innovation, an Energy Frontier Research Center funded by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences under Award Number DE-SC0001004. Some of the images of the cover picture were taken from http://www.presentermedia.com.

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