Fast Pyrolysis of 13C‑Labeled Cellobioses: Gaining Insights into the Mechanisms of Fast Pyrolysis of Carbohydrates

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 n...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-02, Vol.80 (3), p.1909-1914
Main Authors: Degenstein, John C, Murria, Priya, Easton, Mckay, Sheng, Huaming, Hurt, Matt, Dow, Alex R, Gao, Jinshan, Nash, John J, Agrawal, Rakesh, Delgass, W. Nicholas, Ribeiro, Fabio H, Kenttämaa, Hilkka I
Format: Article
Language:English
Subjects:
Carbohydrates - chemistry
Carbon Isotopes - chemistry
Cellobiose - chemistry
Cellulose - chemistry
Hexoses - chemistry
Hot Temperature
Quantum Theory
Tandem Mass Spectrometry
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo5025255