Catalytic activity of hierarchical beta zeolites in the Prins cyclization of (−)-isopulegol with acetone

Mathias Laluc; Roman Barakov; Päivi Mäki-Arvela; Nataliya Shcherban; Dmitry Yu Murzin

doi:10.1016/j.apcata.2021.118131

Catalytic activity of hierarchical beta zeolites in the Prins cyclization of (−)-isopulegol with acetone

Mathias Laluc, Roman Barakov, Päivi Mäki-Arvela, Nataliya Shcherban, Dmitry Yu Murzin^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Scientific › peer-review

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Abstract

Several hierarchical beta zeolites prepared via hydrothermal treatment of a concentrated zeolite gel-precursor were investigated in Prins cyclisation between (–)-isopulegol and acetone acting as a reactant and a solvent for production of a chromenol compound exhibiting antiviral activity. The catalysts were characterized by SEM, TEM, nitrogen physisorption, ammonia TPD, adsorption-desorption of pyridine and 2,4,6-tri-tert-butylpyridine with FTIR spectroscopy. For the Prins cyclization performed at 30 °C, the highest yield of the desired product was obtained over a zeolite catalyst containing a developed mesoporosity with a uniform mesopore size and an optimum ratio of Brønsted to Lewis acid sites.

Original language	English
Article number	118131
Journal	Applied Catalysis A: General
Volume	618
DOIs	https://doi.org/10.1016/j.apcata.2021.118131
Publication status	Published - 25 May 2021
MoE publication type	A1 Journal article-refereed

Funding

NS acknowledges the support of the National Research Foundation of Ukraine to the project “New effective zeolite catalysts for environmentally friendly processes of the conversion of renewable raw materials into valuable organic compounds” (project number 2020.02/0335). RB acknowledges the support of the Czech Science Foundation to the project EXPRO ( 19-27551X ). NS acknowledges the support of the National Research Foundation of Ukraine to the project ?New effective zeolite catalysts for environmentally friendly processes of the conversion of renewable raw materials into valuable organic compounds? (project number 2020.02/0335). RB acknowledges the support of the Czech Science Foundation to the project EXPRO (19-27551X). The authors express their gratitude to colleagues from L.V. Pisarzhevsky Institute of Physical Chemistry who contributed to the experimental part, in particular Pavel Yaremov for nitrogen adsorption measurements and Valentina Tsyrina for TPD of ammonia. The authors acknowledge the contribution of Dr. Igor Bezverkhyy (Universit? de Bourgogne, France), Dr. Mykola Skoryk (?NanoMedTech?, Ukraine), Dr. Sergii Sergiienko (University of Aveiro, Portugal), Kateryna Filatova (Tomas Bata University in Zl?n, Czech Republic) and Ang Li (Charles University in Prague) in carrying out SEM and TEM investigations.

Keywords

Chromenol
Hierarchical zeolite
Prins cyclisation
Tetrahydropyran ring structure

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10.1016/j.apcata.2021.118131

Prins cyclisation isopulegol and acetone 5_revised cleanAccepted author manuscript, 2.33 MBLicence: CC BY-NC-ND

https://urn.fi/URN:NBN:fi-fe2023050139608

Cite this

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title = "Catalytic activity of hierarchical beta zeolites in the Prins cyclization of (−)-isopulegol with acetone",

abstract = "Several hierarchical beta zeolites prepared via hydrothermal treatment of a concentrated zeolite gel-precursor were investigated in Prins cyclisation between (–)-isopulegol and acetone acting as a reactant and a solvent for production of a chromenol compound exhibiting antiviral activity. The catalysts were characterized by SEM, TEM, nitrogen physisorption, ammonia TPD, adsorption-desorption of pyridine and 2,4,6-tri-tert-butylpyridine with FTIR spectroscopy. For the Prins cyclization performed at 30 °C, the highest yield of the desired product was obtained over a zeolite catalyst containing a developed mesoporosity with a uniform mesopore size and an optimum ratio of Br{\o}nsted to Lewis acid sites.",

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AU - Laluc, Mathias

AU - Barakov, Roman

AU - Mäki-Arvela, Päivi

AU - Shcherban, Nataliya

AU - Murzin, Dmitry Yu

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N2 - Several hierarchical beta zeolites prepared via hydrothermal treatment of a concentrated zeolite gel-precursor were investigated in Prins cyclisation between (–)-isopulegol and acetone acting as a reactant and a solvent for production of a chromenol compound exhibiting antiviral activity. The catalysts were characterized by SEM, TEM, nitrogen physisorption, ammonia TPD, adsorption-desorption of pyridine and 2,4,6-tri-tert-butylpyridine with FTIR spectroscopy. For the Prins cyclization performed at 30 °C, the highest yield of the desired product was obtained over a zeolite catalyst containing a developed mesoporosity with a uniform mesopore size and an optimum ratio of Brønsted to Lewis acid sites.

AB - Several hierarchical beta zeolites prepared via hydrothermal treatment of a concentrated zeolite gel-precursor were investigated in Prins cyclisation between (–)-isopulegol and acetone acting as a reactant and a solvent for production of a chromenol compound exhibiting antiviral activity. The catalysts were characterized by SEM, TEM, nitrogen physisorption, ammonia TPD, adsorption-desorption of pyridine and 2,4,6-tri-tert-butylpyridine with FTIR spectroscopy. For the Prins cyclization performed at 30 °C, the highest yield of the desired product was obtained over a zeolite catalyst containing a developed mesoporosity with a uniform mesopore size and an optimum ratio of Brønsted to Lewis acid sites.

KW - Chromenol

KW - Hierarchical zeolite

KW - Prins cyclisation

KW - Tetrahydropyran ring structure

UR - https://www.scopus.com/pages/publications/85103702513

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ER -

Catalytic activity of hierarchical beta zeolites in the Prins cyclization of (−)-isopulegol with acetone

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Keywords

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