Volume 9 Issue 6
Jun.  2024
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Article Navigation >  Green Energy&Environment  > 2024  >  9(6): 1016-1026
Xing Fu, Yexin Hu, Ping Hu, Hui Li, Shuguang Xu, Liangfang Zhu, Changwei Hu. Mapping out the reaction network of humin formation at the initial stage of fructose dehydration in water. Green Energy&Environment, 2024, 9(6): 1016-1026. doi: 10.1016/j.gee.2022.09.012
Citation: Xing Fu, Yexin Hu, Ping Hu, Hui Li, Shuguang Xu, Liangfang Zhu, Changwei Hu. Mapping out the reaction network of humin formation at the initial stage of fructose dehydration in water. Green Energy&Environment, 2024, 9(6): 1016-1026. doi: 10.1016/j.gee.2022.09.012
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Mapping out the reaction network of humin formation at the initial stage of fructose dehydration in water

doi: 10.1016/j.gee.2022.09.012

  • a. Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan, 610064, China;

  • b. State Key Laboratory of Southwestern Chinese Medicine Resources, Innovative Institute of Chinese Medicine and Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu, Sichuan, 611137, China

Funds:

The authors acknowledge financial support from the National Natural Science Foundation of China (No. 21875149), 111 project (B17030), and the Basal Research Fund of the Central University.

  • Received date 06 August 2022, Accepted date 27 September 2022, RevRecd date 18 September 2022, Publish date 04 October 2022,
    Abstract
  • The formation of humins hampers the large-scale production of 5-hydroxymethylfurfural (HMF) in biorefinery. Here, a detailed reaction network of humin formation at the initial stage of fructose-to-HMF dehydration in water is delineated by combined experimental, spectroscopic, and theoretical studies. Three bimolecular reaction pathways to build up soluble humins are demonstrated. That is, the intermolecular etherification of β-furanose at room temperature initiates the C12 path, whereas the C-C cleavage of α-furanose at 130-150 ℃ leads to C11 path, and that of open-chain fructose at 180 ℃ to C11' path. The successive intramolecular dehydrations and condensations of the as-formed bimolecular intermediates lead to three types of soluble humins. We show that the C12 path could be restrained by using HCl or AlCl3 catalyst, and both the C12 and C11' paths could be effectively inhibited by adding THF as a co-solvent or accelerating heating rate via microwave heating.

     

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