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Highly efficient and N-bromosuccinimide-mediated conversion of carbohydrates to 5-hydroxymethylfurfural under mild conditions

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Abstract

Highly efficient and selective conversion of different carbohydrates to 5-hydroxymethylfurfural (HMF) has been successfully performed with N-bromosuccinimide (NBS) as a promoter. In the presence of single NBS, a 64.2 % yield of HMF from fructose was obtained in N-methylpyrrolidone for 2 h. The effects of time, temperature and reaction media are discussed. It was concluded that the preliminary bromination of substrate could improve the generation of HMF compared to the direct dehydration process. Moreover, the HMF yield could be elevated to 79.6 and 82.3 % when FeCl3 and SnCl4 were used as the additives, respectively. Furthermore, the addition of CrCl3 facilitated the conversion pathway from glucose, sucrose, inulin, or cellulose to HMF. A 57.3, 68.2, 62.4, or 6.1 % yield of HMF was, respectively, obtained in the presence of CrCl3 and NBS under mild conditions, which will therefore generate a promising application strategy for biomass transformation.

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Acknowledgment

We thank the financial support of the Natural Science Foundation of China (Project Number 21003093).

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin, 300384, People’s Republic of China

    Guo Tian, Xinli Tong, Yanhua Wang, Yongtao Yan & Song Xue

Authors
  1. Guo Tian
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  2. Xinli Tong
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  3. Yanhua Wang
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  4. Yongtao Yan
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  5. Song Xue
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Corresponding authors

Correspondence to Xinli Tong or Song Xue.

Electronic supplementary material

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11164_2012_837_MOESM1_ESM.doc

The HPLC measurement, HPLC and GC–MS spectra of product, NMR data of HMF can be obtained in the Supplementary Information. (DOC 116 kb)

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Tian, G., Tong, X., Wang, Y. et al. Highly efficient and N-bromosuccinimide-mediated conversion of carbohydrates to 5-hydroxymethylfurfural under mild conditions. Res Chem Intermed 39, 3255–3263 (2013). https://doi.org/10.1007/s11164-012-0837-x

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  • DOI: https://doi.org/10.1007/s11164-012-0837-x

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