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Synthesis of 5-ethoxymethylfurfural from saccharides using combined metal–surfactant catalyst in ethanol/dimethyl sulfoxide

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Abstract

The synthesis of 5-ethoxymethylfurfural (EMF) from glucose using metal chlorides or combined metal–surfactant catalysts as Lewis acids in a solution of ethanol/dimethyl sulfoxide was investigated. Metal chlorides such as aluminum chloride and chromium(III) chloride mainly produced 5-hydroxymethylfurfural and ethyl glucoside in reactions at 140 °C for 180 min. However, the combined metal–surfactant catalysts aluminum tridodecyl sulfate (Al(DS)3) and chromium(III) tridodecyl sulfate efficiently improved the yield of EMF from glucose. The maximum yield of EMF using Al(DS)3 was 37.9% at 160 °C for 60 min. Moreover, the EMF yields from other saccharides (fructose, mannose, sucrose, cellobiose, and inulin) in the presence of Al(DS)3 as a catalyst ranged from 31.2 to 59.3%.

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Acknowledgements

The authors thank Professor Izumi Watanabe at Tokyo University of Agriculture and Technology for the determination of metal contents using ICP-AES. The authors also thank the staff of the center for the elemental analyses of organic compounds at Kyushu University and Enago (www.enago.jp) for some of the elemental analyses and for the English language review, respectively.

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Authors and Affiliations

  1. United Graduate School of Agricultural Science, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu, Tokyo, 183-8509, Japan

    Yoshikazu Mori

  2. College of Bioresource Sciences, Nihon University, 1866 Kameino, Fujisawa, Kanagawa, 252-0880, Japan

    Yoshihiro Katayama

  3. Institute of Agriculture, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu, Tokyo, 183-8509, Japan

    Toshiyuki Shikata & Natsuki Kasuya

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  1. Yoshikazu Mori
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  2. Yoshihiro Katayama
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  3. Toshiyuki Shikata
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  4. Natsuki Kasuya
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Correspondence to Natsuki Kasuya.

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Mori, Y., Katayama, Y., Shikata, T. et al. Synthesis of 5-ethoxymethylfurfural from saccharides using combined metal–surfactant catalyst in ethanol/dimethyl sulfoxide. Res Chem Intermed 46, 609–620 (2020). https://doi.org/10.1007/s11164-019-03980-4

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