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New reactions of betulin with sulfamic acid and ammonium sulfamate in the presence of solid catalysts

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Abstract

Betulin is a biologically active triterpenoid substance, which can be isolated from birch bark. We report on a new approach to the synthesis of betulin sulfamate with sulfamic acid and ammonium sulfamate in the presence of solid catalysts, including Amberlyst 15® and Sibunit (granules) oxidized at 500 °C, Sibunit (powder) oxidized at 400 °C, Sibunit-sulfated, TiO2, and ɣ-Al2O3. It is shown that the synthesis with both sulfamic acid and ammonium sulfamate in the presence of an Amberlyst 15® catalyst yields sulfur derivatives of betulin. This catalyst has been proven to remain active at the repeated (up to four cycles) use. A reaction scheme for the catalytic production of sulfur derivatives of betulin is proposed. The obtained sulfur derivatives of betulin have been examined by Fourier transform infrared and ultraviolet visible spectroscopy, scanning electron and optical microscopy, X-ray diffractometry, thermogravimetric analysis, differential scanning calorimetry, and elemental analysis. It has been found by Fourier transform infrared spectroscopy that the use of sulfamic acid with an Amberlyst 15® catalyst ensures the formation of betulin sulfates, while when using ammonium sulfamate with the same catalyst, the sulfate and other betulin derivatives are obtained along with sulfates. It has been established from the X-ray diffractometry data that sulfation of betulin causes its stronger amorphization.

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Acknowledgements

This study was carried out within the budget plan no. 0287-2021-0017 for the Institute of Chemistry and Chemical Technology, Siberian Branch of the Russian Academy of Sciences on the equipment of the Krasnoyarsk Regional Center for Collective Use, Krasnoyarsk Scientific Center, Siberian Branch of the Russian Academy of Sciences. The authors are grateful to M.A. Lutoshkin for recording the UV-Vis spectra.

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Authors and Affiliations

  1. Siberian Federal University, pr. Svobodny 79, Krasnoyarsk, 660041, Russia

    Aleksandr S. Kazachenko, Natalya Yu. Vasilieva, Yuriy N. Malyar, Angelina V. Miroshnikova, Valentina S. Borovkova, Anna S. Kazachenko, Andrey M. Skripnikov, Dmitry V. Zimonin & Vladislav A. Ionin

  2. Institute of Chemistry and Chemical Technology, Siberian Branch, Krasnoyarsk Scientific Center, Russian Academy of Sciences, Akademgorodok 50, bld. 24, Krasnoyarsk, 660036, Russia

    Aleksandr S. Kazachenko, Natalya Yu. Vasilieva, Olga Yu. Fetisova, Valentine V. Sychev, Evgeniy V. Elsuf’ev, Yuriy N. Malyar, Angelina V. Miroshnikova, Valentina S. Borovkova, Yaroslava D. Berezhnaya, Andrey M. Skripnikov, Dmitry V. Zimonin & Vladislav A. Ionin

  3. Laboratory of Quantum and Statistical Physics (LR18ES18), Faculty of Sciences, University of Monastir, 5079, Monastir, Tunisia

    Noureddine Issaoui

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  1. Aleksandr S. Kazachenko
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Kazachenko, A.S., Vasilieva, N.Y., Fetisova, O.Y. et al. New reactions of betulin with sulfamic acid and ammonium sulfamate in the presence of solid catalysts. Biomass Conv. Bioref. 14, 4245–4256 (2024). https://doi.org/10.1007/s13399-022-02587-x

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