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Comparison of Structural Features of Humins Formed Catalytically from Glucose, Fructose, and 5-Hydroxymethylfurfuraldehyde
Abstract
The IR spectra of humins formed during the acid-catalyzed conversion of glucose, fructose, and 5-hydroxymethylfurfuraldehyde were compared. The spectra are quite similar except for three groups of features that can be attributed to furan rings and carbonyl groups conjugated with carbon–carbon double bonds. IR spectroscopy further revealed that benzyl groups could be added to the humins as they formed or in a separate aldol addition/condensation reaction after they had been recovered. The IR spectra are consistent with a model where each of the three reactants must first be converted to 2,5-dioxo-6-hydroxyhexanal (DHH) before humins can form via subsequent aldol addition and condensation. The differences in the IR spectral features can then be explained by variations in the concentrations of other aldehydes and ketones that can react with DHH.
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Cites
Kabyemela, B. M., Adschiri, T., Malaluan, R. M., & Arai, K. (1999) · Industrial & Engineering Chemistry Research · doi:10.1021/ie9806390 · Cited by 592
Acid-Catalyzed Production of 5-Hydroxymethyl Furfural from d-Fructose in Subcritical Water
Salak Asghari, F., & Yoshida, H. (2006) · Industrial & Engineering Chemistry Research · doi:10.1021/ie051088y · Cited by 500
Cited by
van Zandvoort, I., Wang, Y., Rasrendra, C. B., van Eck, E. R. H., Bruijnincx, P. C. A., Heeres, H. J., & Weckhuysen, B. M. (2013) · ChemSusChem · doi:10.1002/cssc.201300332 · Cited by 624
From lignocellulosic biomass to levulinic acid: A review on acid-catalyzed hydrolysis
Kang, S., Fu, J., & Zhang, G. (2018) · Renewable and Sustainable Energy Reviews · doi:10.1016/j.rser.2018.06.016 · Cited by 580
Hydrothermal Reactions of Biomolecules Relevant for Microalgae Liquefaction
Changi, S. M., Faeth, J. L., Mo, N., & Savage, P. E. (2015) · Industrial & Engineering Chemistry Research · doi:10.1021/acs.iecr.5b02771 · Cited by 175
Hydrothermal Carbonization of Fructose: Growth Mechanism and Kinetic Model
Jung, D., Zimmermann, M., & Kruse, A. (2018) · ACS Sustainable Chemistry & Engineering · doi:10.1021/acssuschemeng.8b02118 · Cited by 109
Metadata
- Authors
- Patil, S. K. R., Heltzel, J., & Lund, C. R. F.
- Venue
- Energy & Fuels
- Publisher
- American Chemical Society (ACS)
- Published
- 2012-07-23
- Volume
- 26
- Issue
- 8
- Pages
- 5281-5293
- ISSN
- 0887-0624 (ISSN-L)
- 1520-5029
- OpenAlex
- W2334280742
- Cited by
- 364
- References
- 2
- FWCI
- 7.67
- Type
- journal article
- Language
- en
- Open access
- closed
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- Patil, S. K. R., Heltzel, J., & Lund, C. R. F. (2012). Comparison of Structural Features of Humins Formed Catalytically from Glucose, Fructose, and 5-Hydroxymethylfurfuraldehyde. Energy & Fuels. https://doi.org/10.1021/ef3007454
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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