期刊
CHEMSUSCHEM
卷 13, 期 3, 页码 501-512出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.201902309
关键词
degradative condensation; fructose; humins; solvent effects; tautomerism
资金
- National Natural Science Foundation of China [21875149]
- 111 project [B17030]
- Basal Research Fund of the Central University [2016SCU04B06]
The degradative condensation of hexose, which originates from the C-C cleavage of hexose and condensation of degraded hexose fragment, is one of the possible reaction pathways for the formation of humins in hexose dehydration to 5-hydroxymethylfurfural (HMF). Herein, the impacts of several polar aprotic solvents on the degradative condensation of fructose to small-molecule carboxylic acids and oligomers (possible precursors of humins) are reported. In particular, a close relationship between the tautomeric distribution of fructose in solvents and the mechanism of degradative condensation is demonstrated. Typically, alpha-fructofuranose in 1,4-dioxane and acyclic open-chain fructose in THF favor the conversion of fructose to formic acid and oligomers; alpha-fructopyranose in gamma-valerolactone or N-methylpyrrolidone favors levulinic acid and oligomers, whereas beta-fructopyranose in 4-methyl-2-pentanone favors acetic acid and corresponding oligomers. This close correlation highlights a general understanding of the solvent-controlled formation of oligomers, which represents an important step toward the rational design of effective solvent systems for HMF production.
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