Critical Influence of 5-Hydroxymethylfurfural Aging and Decomposition on the Utility of Biomass Conversion in Organic Synthesis.
Publication type: Journal Article
Publication date: 2016-06-08
scimago Q1
wos Q1
SJR: 5.550
CiteScore: 27.6
Impact factor: 16.9
ISSN: 14337851, 15213773
PubMed ID:
27271823
General Chemistry
Catalysis
Abstract
Spectral studies revealed the presence of a specific arrangement of 5-hydroxymethylfurfural (5-HMF) molecules in solution as a result of a hydrogen-bonding network, and this arrangement readily facilitates the aging of 5-HMF. Deterioration of the quality of this platform chemical limits its practical applications, especially in synthesis/pharma areas. The model drug Ranitidine (Zantac®) was synthesized with only 15 % yield starting from 5-HMF which was isolated and stored as an oil after a biomass conversion process. In contrast, a much higher yield of 65 % was obtained by using 5-HMF isolated in crystalline state from an optimized biomass conversion process. The molecular mechanisms responsible for 5-HMF decomposition in solution were established by NMR and ESI-MS studies. A highly selective synthesis of a 5-HMF derivative from glucose was achieved using a protecting group at O(6) position.
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Total citations:
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Citations from 2025:
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(11.89%)
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Galkin K. I. et al. Critical Influence of 5-Hydroxymethylfurfural Aging and Decomposition on the Utility of Biomass Conversion in Organic Synthesis. // Angewandte Chemie - International Edition. 2016. Vol. 55. No. 29. pp. 8338-8342.
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Galkin K. I., Krivodaeva E. A., Romashov L. V., S. Zalesskiy S., Kachala V. V., Burykina J. V., Ananikov V. P. Critical Influence of 5-Hydroxymethylfurfural Aging and Decomposition on the Utility of Biomass Conversion in Organic Synthesis. // Angewandte Chemie - International Edition. 2016. Vol. 55. No. 29. pp. 8338-8342.
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RIS
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TY - JOUR
DO - 10.1002/anie.201602883
UR - https://doi.org/10.1002/anie.201602883
TI - Critical Influence of 5-Hydroxymethylfurfural Aging and Decomposition on the Utility of Biomass Conversion in Organic Synthesis.
T2 - Angewandte Chemie - International Edition
AU - Galkin, Konstantin I
AU - Krivodaeva, Elena A
AU - Romashov, Leonid V.
AU - S. Zalesskiy, Sergey
AU - Kachala, Vadim V.
AU - Burykina, Julia V.
AU - Ananikov, Valentine P.
PY - 2016
DA - 2016/06/08
PB - Wiley
SP - 8338-8342
IS - 29
VL - 55
PMID - 27271823
SN - 1433-7851
SN - 1521-3773
ER -
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@article{2016_Galkin,
author = {Konstantin I Galkin and Elena A Krivodaeva and Leonid V. Romashov and Sergey S. Zalesskiy and Vadim V. Kachala and Julia V. Burykina and Valentine P. Ananikov},
title = {Critical Influence of 5-Hydroxymethylfurfural Aging and Decomposition on the Utility of Biomass Conversion in Organic Synthesis.},
journal = {Angewandte Chemie - International Edition},
year = {2016},
volume = {55},
publisher = {Wiley},
month = {jun},
url = {https://doi.org/10.1002/anie.201602883},
number = {29},
pages = {8338--8342},
doi = {10.1002/anie.201602883}
}
Cite this
MLA
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Galkin, Konstantin I., et al. “Critical Influence of 5-Hydroxymethylfurfural Aging and Decomposition on the Utility of Biomass Conversion in Organic Synthesis..” Angewandte Chemie - International Edition, vol. 55, no. 29, Jun. 2016, pp. 8338-8342. https://doi.org/10.1002/anie.201602883.