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

Research output: Contribution to journalArticle

17 Citations (Scopus)

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

Fingerprint

Cellobiose
Pyrolysis
Carbohydrates
Mass spectrometers
Cellulose
Molecules

Cite this

Degenstein, J. C., Murria, P., Easton, M., Sheng, H., Hurt, M., Dow, A. R., ... 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
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. / Fast pyrolysis of 13c-labeled cellobioses : Gaining insights into the mechanisms of fast pyrolysis of carbohydrates. In: Journal of Organic Chemistry. 2015 ; Vol. 80, No. 3. pp. 1909-1914.
@article{458c149fe54a47648837f63065010d89,
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.}",
year = "2015",
month = "2",
day = "6",
doi = "10.1021/jo5025255",
language = "English",
volume = "80",
pages = "1909--1914",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "3",

}

Degenstein, JC, Murria, P, Easton, M, Sheng, H, Hurt, M, Dow, AR, Gao, J, Nash, JJ, Agrawal, R, Delgass, WN, Ribeiro, FH & Kenttämaa, HI 2015, 'Fast pyrolysis of 13c-labeled cellobioses: Gaining insights into the mechanisms of fast pyrolysis of carbohydrates', Journal of Organic Chemistry, vol. 80, no. 3, pp. 1909-1914. https://doi.org/10.1021/jo5025255

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

In: Journal of Organic Chemistry, Vol. 80, No. 3, 06.02.2015, p. 1909-1914.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Fast pyrolysis of 13c-labeled cellobioses

T2 - Gaining insights into the mechanisms of fast pyrolysis of carbohydrates

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

Y1 - 2015/2/6

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=84922719536&partnerID=8YFLogxK

U2 - 10.1021/jo5025255

DO - 10.1021/jo5025255

M3 - Article

C2 - 25562626

AN - SCOPUS:84922719536

VL - 80

SP - 1909

EP - 1914

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 3

ER -