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

doi:10.1021/jo5025255

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

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

38 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 language	English
Pages (from-to)	1909-1914
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	80
Issue number	3
DOIs	https://doi.org/10.1021/jo5025255
State	Published - 6 Feb 2015

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

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.",

author = "Degenstein, {John C.} and Priya Murria and McKay Easton and Huaming Sheng and Matt Hurt and Dow, {Alex R.} and Jinshan Gao and Nash, {John J.} and Rakesh Agrawal and Delgass, {W. Nicholas} and Ribeiro, {Fabio H.} and Kentt{\"a}maa, {Hilkka I.}",

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AU - Degenstein, John C.

AU - Murria, Priya

AU - Easton, McKay

AU - Sheng, Huaming

AU - Hurt, Matt

AU - Dow, Alex R.

AU - Gao, Jinshan

AU - Nash, John J.

AU - Agrawal, Rakesh

AU - Delgass, W. Nicholas

AU - Ribeiro, Fabio H.

AU - Kenttämaa, Hilkka I.

PY - 2015/2/6

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AB - 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.

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

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