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

Title: 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.

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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)

Grant/Contract Number:: SC000997; SC0000997

OSTI ID:: 1384962

Alternate ID(s):: OSTI ID: 1250593

Journal Information:: Biomass and Bioenergy, Vol. 74, Issue C; Related Information: C3Bio partners with Purdue University (lead); Argonne National Laboratory; National Renewable Energy Laboratory; Northeastern University; University of Tennessee; ISSN 0961-9534

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 10 works

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References (22)

Ethanol Can Contribute to Energy and Environmental Goals Farrell, A. E. Science, Vol. 311, Issue 5760 https://doi.org/10.1126/science.1121416	journal	January 2006
Chemicals from Biomass Dodds, D. R.; Gross, R. A. Science, Vol. 318, Issue 5854 https://doi.org/10.1126/science.1146356	journal	November 2007
Cell-wall carbohydrates and their modification as a resource for biofuels Pauly, Markus; Keegstra, Kenneth The Plant Journal, Vol. 54, Issue 4, p. 559-568 https://doi.org/10.1111/j.1365-313X.2008.03463.x	journal	May 2008
Maize and sorghum: genetic resources for bioenergy grasses Carpita, Nicholas C.; McCann, Maureen C. Trends in Plant Science, Vol. 13, Issue 8 https://doi.org/10.1016/j.tplants.2008.06.002	journal	August 2008
Biomimetic Catalysis for Hemicellulose Hydrolysis in Corn Stover Lu, Y.; Mosier, N. S. Biotechnology Progress, Vol. 23, Issue 1 https://doi.org/10.1021/bp060223e	journal	February 2007
Liquid-Phase Catalytic Processing of Biomass-Derived Oxygenated Hydrocarbons to Fuels and Chemicals Chheda, Juben N.; Huber, George W.; Dumesic, James A. Angewandte Chemie International Edition, Vol. 46, Issue 38, p. 7164-7183 https://doi.org/10.1002/anie.200604274	journal	September 2007
Synergies between Bio- and Oil Refineries for the Production of Fuels from Biomass Huber, George W.; Corma, Avelino Angewandte Chemie International Edition, Vol. 46, Issue 38, p. 7184-7201 https://doi.org/10.1002/anie.200604504	journal	September 2007
Phase Modifiers Promote Efficient Production of Hydroxymethylfurfural from Fructose Roman-Leshkov, Yuriy; Chheda, Juben N.; Dumesic, James A. Science, Vol. 312, Issue 5782, p. 1933-1937 https://doi.org/10.1126/science.1126337	journal	June 2006
Metal Chlorides in Ionic Liquid Solvents Convert Sugars to 5-Hydroxymethylfurfural Zhao, H.; Holladay, J. E.; Brown, H. Science, Vol. 316, Issue 5831, p. 1597-1600 https://doi.org/10.1126/science.1141199	journal	June 2007
Synthesis of Furfural from Xylose and Xylan Binder, Joseph B.; Blank, Jacqueline J.; Cefali, Anthony V. ChemSusChem, Vol. 3, Issue 11 https://doi.org/10.1002/cssc.201000181	journal	September 2010
The conversion of -xylose and -glucuronic acid to 2-furaldehyde Feather, Milton S. Tetrahedron Letters, Vol. 11, Issue 48 https://doi.org/10.1016/S0040-4039(01)98688-5	journal	January 1970
Routes of conversion of D-xylose, hexuronic acids, and L-ascorbic acid to 2-furaldehyde Feather, Milton S.; Harris, Donald W.; Nichols, Susan B. The Journal of Organic Chemistry, Vol. 37, Issue 10 https://doi.org/10.1021/jo00975a032	journal	May 1972
Evidence for a C-2→C-1 intramolecular hydrogen-transfer during the acid-catalyzed isomerization of D-glucose to D-fructose ag] Harris, Donald W.; Feather, Milton S. Carbohydrate Research, Vol. 30, Issue 2 https://doi.org/10.1016/S0008-6215(00)81822-4	journal	October 1973
Pentose Reactions. i. Furfural Formation Hurd, Charles D.; Isenhour, Lloyd L. Journal of the American Chemical Society, Vol. 54, Issue 1 https://doi.org/10.1021/ja01340a048	journal	January 1932
Mechanism of formation of 2-furaldehyde from d-xylose Antal, Michael Jerry; Leesomboon, Tongchit; Mok, William S. Carbohydrate Research, Vol. 217 https://doi.org/10.1016/0008-6215(91)84118-X	journal	September 1991
13C-labeled aldopentoses: detection and quantitation of cyclic and acyclic forms by heteronuclear 1D and 2D NMR spectroscopy Drew, Kenneth N.; Zajicek, Jaroslav; Bondo, Gail Carbohydrate Research, Vol. 307, Issue 3-4 https://doi.org/10.1016/S0008-6215(98)00040-8	journal	February 1998
Energetics of Xylose Decomposition as Determined Using Quantum Mechanics Modeling Nimlos, Mark R.; Qian, Xianghong; Davis, Mark The Journal of Physical Chemistry A, Vol. 110, Issue 42 https://doi.org/10.1021/jp0626770	journal	October 2006
Selective Conversion of Biomass Hemicellulose to Furfural Using Maleic Acid with Microwave Heating Kim, Eurick S.; Liu, Shuo; Abu-Omar, Mahdi M. Energy & Fuels, Vol. 26, Issue 2 https://doi.org/10.1021/ef2014106	journal	January 2012
Phase-modulated stored waveform inverse Fourier transform excitation for trapped ion mass spectrometry Chen, Ling.; Wang, Tao Chin Lin.; Ricca, Tom L. Analytical Chemistry, Vol. 59, Issue 3 https://doi.org/10.1021/ac00130a016	journal	February 1987
Tailored excitation for Fourier transform ion cyclotron mass spectrometry Marshall, Alan G.; Wang, Tao Chin Lin; Ricca, Tom L. Journal of the American Chemical Society, Vol. 107, Issue 26 https://doi.org/10.1021/ja00312a015	journal	December 1985
Rapid analysis of formic acid, acetic acid, and furfural in pretreated wheat straw hydrolysates and ethanol in a bioethanol fermentation using atmospheric pressure chemical ionisation mass spectrometry Davies, Scott M.; Linforth, Rob S.; Wilkinson, Stuart J. Biotechnology for Biofuels, Vol. 4, Issue 1 https://doi.org/10.1186/1754-6834-4-28	journal	January 2011
Identification and Counting of Oxygen Functionalities in Aromatic Analytes Related to Lignin by Using Negative-Mode Electrospray Ionization and Multiple Collision-Activated Dissociation Steps Amundson, Lucas M.; Eismin, Ryan J.; Reece, Jennifer N. Energy & Fuels, Vol. 25, Issue 7 https://doi.org/10.1021/ef200141w	journal	July 2011

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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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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)

Title: Tandem mass spectrometric characterization of the conversion of xylose to furfural

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