Abstract
Ab initio molecular dynamics (MD) simulations were employed to elucidate xylose and glucose degradation pathways. In the case of xylose, a 2,5-anhydride intermediate was observed leading to the formation of furfural through elimination of water. This pathway agrees with one of the mechanisms proposed in the literature in that no open chain intermediates were found. In the case of glucose, a series of intermediates were observed before forming the 2,5-anhydride intermediate that eventually leads to hydroxymethylfurfural (HMF). One of these intermediates was a very short-lived open-chain form. Furthermore, two novel side-reaction pathways were identified, which lead to degradation products other than HMF.
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References
Wyman, C. E., Bain, R. L., Hinman, N. D., and Stevens, D. J. (1993), Renewable Energy: Sources for Fuels and Electricity, Island Press Washington, DC.
Sheehan, J. J. (1994), Bioconversion for production of renewable transportation fuels in the United States: a strategic perspective. In Enzymatic Conversion of Biomass for Fuels Production. (Himmel, M. E., Baker, J. O., and Overend, R. P., eds.), American Chemical Society, Washington, DC, Ni 566, pp. 1–52.
Bergeron, R (1996), Bioethanol market forces. In Handbook on Bioethanol (Wyman, C. E., ed.) Taylor & Francis, Washington, DC, pp. 179–195.
Antal, M. J., Leesomboon, T., Mok, W. S., and Richards, G. N. (1991), Carbohydrate Research 217, 71–85; Antal, M. J., Mok, W. S., and Richards, G. N. (1990), Carbohydrate Research 199, 91–109; Antal, M. J., Mok, W. S., and Richards, G. N. (1990), Carbohydrate Research 199, 111–115.
McKibbins, S. W., Harris, J. F., Saeman, J. R, and Neill, W. K. (1962), J. Forest Products 19, 17–23.
Garrett, E. R. and Dvorchik, B. H. (1969), J. Pharmaceutical Sciences, 58, 813–820.
Parker, S., Calnon, ML, Feinberg, D., Power, A., and Weiss, C. (2000), The Value of Furfural/Ethanol Coproduction from Acid Hydrolysis Process, SERI/TR-231-2000, Solar Energy Research Institute, Golden, Colorado.
Van Dam, H. E., Kieboom, A. P. G., and van Bellum, H. (1986), Starch/Starke 38, 95–101.
Bouchard, J., Overend, R. P., Chornet, E., and Van Calsteren, M.-R. (1992), J. Wood Chem. Tech. 12, 335–354.
Mok, W. S., Antal M. J. Jr, and Varhegyi, G. (1992), Indust. Engineer. Chem. Res. 31, 94–1000.
Lee, Y. Y, Kim, J.-S., Xiang, D. Q., and Kim, T.-H. (2001), Enhancement of Dilute-Acid Total-Hydrolysis Process for High-Yield Saacharification of Cellulosic Biomass, Subcontract Final Report.
Abatzoglou, N., Bouchard, J., Chornet, E., and Overend, R. P. (1986), Can. J. Chem. Engineer. 64, 781–786.
Johnson, D. K. and Davis, M. (2003), Identify Reaction Pathways in Dilute Cellulose Hydrolysis to Improve Mass Balance Closure at High Conversions, NREL Biomass Program P-Milestone Completion Report.
Torget, R. W., Kim, J. S., and Lee, Y. Y. (2000), Ind. Eng. Chem. Res. 39, 2817–2825.
CPMD3.7, copyrighted jointly by IBM Corp and by Max-Planck Institute, Stuttgart; http://www.cpmd.org.
Car, R. and Parrinello M. (1985), Phys. Rev. Lett. 55, 2471–2474.
Nimlos, M. R., Qian, X., Johnson, D. K., and Himmel, M. E., to be published.
Feather, M. S. (1970), Tetrahedron Lett. 4143–4145.
Harris, D. W. and Feather, M. S. (1973), Carbohydrate Res. 30, 359–365.
Torget, R. W., Himmel, M. E., Brady, J., and Skopec, C. (2003), Characterize and Quantify Energetics at the Aqueous Boundary Layer of a Cellulose Microcrystallite Using Computational Chemistry, NREL Biomass Program Milestone Completion Report.
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Qian, X., Nimlos, M.R., Johnson, D.K., Himmel, M.E. (2005). Acidic Sugar Degradation Pathways. In: Davison, B.H., Evans, B.R., Finkelstein, M., McMillan, J.D. (eds) Twenty-Sixth Symposium on Biotechnology for Fuels and Chemicals. ABAB Symposium. Humana Press. https://doi.org/10.1007/978-1-59259-991-2_84
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DOI: https://doi.org/10.1007/978-1-59259-991-2_84
Publisher Name: Humana Press
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