Fast pyrolysis of 13c-labeled cellobioses: Gaining insights into the mechanisms of fast pyrolysis of carbohydrates

John C. Degenstein, Priya Murria, McKay Easton, Huaming Sheng, Matt Hurt, Alex R. Dow, Jinshan Gao, John J. Nash, Rakesh Agrawal, W. Nicholas Delgass, Fabio H. Ribeiro, Hilkka I. Kenttämaa

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19 Scopus citations

Abstract

A fast-pyrolysis probe/tandem mass spectrometer combination was utilized to determine the initial fast-pyrolysis products for four different selectively 13C-labeled cellobiose molecules. Several products are shown to result entirely from fragmentation of the reducing end of cellobiose, leaving the nonreducing end intact in these products. These findings are in disagreement with mechanisms proposed previously. Quantum chemical calculations were used to identify feasible low-energy pathways for several products. These results provide insights into the mechanisms of fast pyrolysis of cellulose.

Original languageEnglish
Pages (from-to)1909-1914
Number of pages6
JournalJournal of Organic Chemistry
Volume80
Issue number3
DOIs
StatePublished - 6 Feb 2015

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    Degenstein, J. C., Murria, P., Easton, M., Sheng, H., Hurt, M., Dow, A. R., Gao, J., Nash, J. J., Agrawal, R., Delgass, W. N., Ribeiro, F. H., & Kenttämaa, H. I. (2015). Fast pyrolysis of 13c-labeled cellobioses: Gaining insights into the mechanisms of fast pyrolysis of carbohydrates. Journal of Organic Chemistry, 80(3), 1909-1914. https://doi.org/10.1021/jo5025255