Tandem mass spectrometric characterization of the conversion of xylose to furfural

Vinueza, Nelson R.; Kim, Eurick S.; Gallardo, Vanessa A.; Mosier, Nathan S.; Abu-Omar, Mahdi M.; Carpita, Nicholas C.; Kenttämaa, Hilkka I.

doi:10.1016/j.biombioe.2014.10.012

Tandem mass spectrometric characterization of the conversion of xylose to furfural

Journal Article · Fri Jan 16 00:00:00 EST 2015 · Biomass and Bioenergy

DOI:https://doi.org/10.1016/j.biombioe.2014.10.012· OSTI ID:1384962

Vinueza, Nelson R. ^[1]; Kim, Eurick S. ^[1]; Gallardo, Vanessa A. ^[1]; Mosier, Nathan S. ^[1]; Abu-Omar, Mahdi M. ^[1]; Carpita, Nicholas C. ^[1]; Kenttämaa, Hilkka I. ^[1]

Purdue Univ., West Lafayette, IN (United States)

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.

View Accepted Manuscript (DOE)

Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Center for Direct Catalytic Conversion of Biomass to Biofuels (C3Bio) (C3Bio)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: SC0000997

OSTI ID:: 1384962

Alternate ID(s):: OSTI ID: 1210299
OSTI ID: 22481324
OSTI ID: 1250593

Journal Information:: Biomass and Bioenergy, Journal Name: Biomass and Bioenergy Journal Issue: C Vol. 74; ISSN 0961-9534

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

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Biobased Furanics: Kinetic Studies on the Acid Catalyzed Decomposition of 2-Hydroxyacetyl Furan in Water Using Brönsted Acid Catalysts Soetedjo, J. N. M.; van de Bovenkamp, H. H.; Deuss, P. J. ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 5 https://doi.org/10.1021/acssuschemeng.6b03198	journal	April 2017

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13C labeling
59 BASIC BIOLOGICAL SCIENCES
Bio-inspired
Biofuels (including algae and biomass)
Catalysis (heterogeneous)
Catalysis (homogeneous)
Catalytic conversion
Furfural
Maleic acid
Materials and chemistry by design
Synthesis (scalable processing)
Synthesis (self-assembly)
Tandem mass spectrometry
Xylose

Tandem mass spectrometric characterization of the conversion of xylose to furfural

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References (23)

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