Solid Acid Catalysts for Coumarin Synthesis by the Pechmann Reaction: MOFs versus Zeolites

Authors

  • Dr. Maksym Opanasenko,

    1. J. Heyrovský Institute of Physical Chemistry, Academy of Sciences of Czech Republic v.v.i Dolejškova 3, 182 23 Prague 8 (Czech Republic)
    2. L. V. Pisarzhevskiy Institute of Physical Chemistry, National Academy of Sciences of Ukraine, 31 pr. Nauky Kyiv 03028 (Ukraine)
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  • Mariya Shamzhy,

    1. J. Heyrovský Institute of Physical Chemistry, Academy of Sciences of Czech Republic v.v.i Dolejškova 3, 182 23 Prague 8 (Czech Republic)
    2. L. V. Pisarzhevskiy Institute of Physical Chemistry, National Academy of Sciences of Ukraine, 31 pr. Nauky Kyiv 03028 (Ukraine)
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  • Prof. Jiří Čejka

    Corresponding author
    1. J. Heyrovský Institute of Physical Chemistry, Academy of Sciences of Czech Republic v.v.i Dolejškova 3, 182 23 Prague 8 (Czech Republic)
    • J. Heyrovský Institute of Physical Chemistry, Academy of Sciences of Czech Republic v.v.i Dolejškova 3, 182 23 Prague 8 (Czech Republic)
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Abstract

The catalytic behavior of metal–organic frameworks Cu-benzene-1,3,5-tricarboxylate (CuBTC) and Fe-benzene-1,3,5-tricarboxylate (FeBTC) was investigated in the Pechmann condensation of different phenols (resorcinol, pyrogallol, and naphthol) with ethyl acetoacetate and compared with large-pore zeolites beta (BEA) and ultrastable Y (USY). Zeolites BEA and USY exhibited high activity in transformations of the most active substrates (resorcinol and pyrogallol) but a low conversion of naphthol was observed. Almost total transformation of naphthol (94–98 % conversion) to the target product was achieved within 24 h of the reaction time over CuBTC and FeBTC. We assume that the regularity in the arrangement of active sites within the framework of CuBTC, which results in the existence of 2 active centers in close proximity, is of critical importance to the transformation of naphthol in the Pechmann reaction that leads to coumarin.

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