Tandem mass spectrometric characterization of the conversion of xylose to furfural
Abstract
We report thermal decomposition of xylose into furfural under acidic conditions has been studied using tandem mass spectrometry. Two different Brønsted acids, maleic and sulfuric acids, were used to demonstrate that varying the Brønsted acid does not affect the mechanism of the reaction. Two selectively labeled xylose molecules, 1-13C and 5-13C-xyloses, were examined to determine which carbon atom is converted to the aldehyde carbon in furfural. This can be done by using tandem mass spectrometry since collision-activated dissociation (CAD) of protonated unlabeled furfural results in the loss of CO from the aldehyde moiety. The loss of a neutral molecule with MW of 29 Da (13CO) was observed for protonated furfural derived from 1-13C-labeled xylose while the loss of a neutral molecule with MW of 28 Da (CO) was observed for protonated furfural derived from 5-13C labeled xylose. These results support the hypothesis that the mechanism of formation of furfural under mildly hot acidic conditions involves an intramolecular rearrangement of protonated xylose into the pyranose form rather than into an open-chain form.
- Authors:
-
- Purdue Univ., West Lafayette, IN (United States)
- Publication Date:
- Research Org.:
- Energy Frontier Research Centers (EFRC) (United States). Center for Direct Catalytic Conversion of Biomass to Biofuels (C3Bio) (C3Bio)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1384962
- Alternate Identifier(s):
- OSTI ID: 1250593
- Grant/Contract Number:
- SC000997; SC0000997
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Biomass and Bioenergy
- Additional Journal Information:
- Journal Volume: 74; Journal Issue: C; Related Information: C3Bio partners with Purdue University (lead); Argonne National Laboratory; National Renewable Energy Laboratory; Northeastern University; University of Tennessee; Journal ID: ISSN 0961-9534
- Publisher:
- Elsevier
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 59 BASIC BIOLOGICAL SCIENCES; Xylose; Furfural; Tandem mass spectrometry; Catalytic conversion; Maleic acid; 13C labeling; Catalysis (homogeneous); Catalysis (heterogeneous); Biofuels (including algae and biomass); Bio-inspired; Materials and chemistry by design; Synthesis (self-assembly); Synthesis (scalable processing)
Citation Formats
Vinueza, Nelson R., Kim, Eurick S., Gallardo, Vanessa A., Mosier, Nathan S., Abu-Omar, Mahdi M., Carpita, Nicholas C., and Kenttämaa, Hilkka I. Tandem mass spectrometric characterization of the conversion of xylose to furfural. United States: N. p., 2015.
Web. doi:10.1016/j.biombioe.2014.10.012.
Vinueza, Nelson R., Kim, Eurick S., Gallardo, Vanessa A., Mosier, Nathan S., Abu-Omar, Mahdi M., Carpita, Nicholas C., & Kenttämaa, Hilkka I. Tandem mass spectrometric characterization of the conversion of xylose to furfural. United States. https://doi.org/10.1016/j.biombioe.2014.10.012
Vinueza, Nelson R., Kim, Eurick S., Gallardo, Vanessa A., Mosier, Nathan S., Abu-Omar, Mahdi M., Carpita, Nicholas C., and Kenttämaa, Hilkka I. Fri .
"Tandem mass spectrometric characterization of the conversion of xylose to furfural". United States. https://doi.org/10.1016/j.biombioe.2014.10.012. https://www.osti.gov/servlets/purl/1384962.
@article{osti_1384962,
title = {Tandem mass spectrometric characterization of the conversion of xylose to furfural},
author = {Vinueza, Nelson R. and Kim, Eurick S. and Gallardo, Vanessa A. and Mosier, Nathan S. and Abu-Omar, Mahdi M. and Carpita, Nicholas C. and Kenttämaa, Hilkka I.},
abstractNote = {We report thermal decomposition of xylose into furfural under acidic conditions has been studied using tandem mass spectrometry. Two different Brønsted acids, maleic and sulfuric acids, were used to demonstrate that varying the Brønsted acid does not affect the mechanism of the reaction. Two selectively labeled xylose molecules, 1-13C and 5-13C-xyloses, were examined to determine which carbon atom is converted to the aldehyde carbon in furfural. This can be done by using tandem mass spectrometry since collision-activated dissociation (CAD) of protonated unlabeled furfural results in the loss of CO from the aldehyde moiety. The loss of a neutral molecule with MW of 29 Da (13CO) was observed for protonated furfural derived from 1-13C-labeled xylose while the loss of a neutral molecule with MW of 28 Da (CO) was observed for protonated furfural derived from 5-13C labeled xylose. These results support the hypothesis that the mechanism of formation of furfural under mildly hot acidic conditions involves an intramolecular rearrangement of protonated xylose into the pyranose form rather than into an open-chain form.},
doi = {10.1016/j.biombioe.2014.10.012},
journal = {Biomass and Bioenergy},
number = C,
volume = 74,
place = {United States},
year = {Fri Jan 16 00:00:00 EST 2015},
month = {Fri Jan 16 00:00:00 EST 2015}
}
Web of Science
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