Chinese Journal of Catalysis ›› 2019, Vol. 40 ›› Issue (11): 1713-1720.DOI: 10.1016/S1872-2067(19)63305-X

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Prins cyclisation of (-)-isopulegol with benzaldehyde over ZSM-5 based micro-mesoporous catalysts for production of pharmaceuticals

Ekaterina Kholkinaa, Paivi Maki-Arvelaa, Chloe Lozachmeuera, Roman Barakovb, Nataliya Shcherbanb, Dmitry Yu. Murzina   

  1. a Johan Gadolin Process Chemistry Centre, Faculty of Science and Engineering, Åbo Akademi University, Turku 20500, Finland;
    b L.V. Pisarzhevsky Institute of Physical Chemistry, National Academy of Sciences of Ukraine, 31 pr. Nauky, Kiev 03028, Ukraine
  • Received:2018-12-07 Revised:2019-01-17 Online:2019-11-18 Published:2019-09-06
  • Contact: Dmitry Yu. Murzin

Abstract: Several ZSM-5 derived micro-mesoporous catalysts were investigated in Prins cyclisation of (-)-isopulegol with benzaldehyde acting as a reactant and a solvent for production of heterocyclic oxygen containing 2H-chromene derivatives including the tetrahydropyran structure and exhibiting biological activity. The investigated catalysts were characterized by nitrogen adsorption, ammonia temperature programmed desorption, adsorption-desorption of pyridine and 2,6-di-tert-butylpyridine with Fourier transform infrared spectroscopic control. For the Prins reaction performed at 70℃, the highest yield of the desired product, equal to 67% at complete conversion of (-)-isopulegol, was obtained over a micro-mesoporous catalyst containing an optimum amount of strong acid sites and mesopores, being 12 fold larger than the size of the desired product.

Key words: Micro-mesoporous material, Prins cyclisation, Tetrahydropyran