Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
Prins cyclization of (-)-isopulegol with benzaldehyde for production of chromenols over organosulfonic clays. / Li-Zhulanov, Nikolai; Mäki-Arvela, Päivi; Laluc, Mathias и др.
в: Molecular Catalysis, Том 478, 110569, 01.11.2019.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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TY - JOUR
T1 - Prins cyclization of (-)-isopulegol with benzaldehyde for production of chromenols over organosulfonic clays
AU - Li-Zhulanov, Nikolai
AU - Mäki-Arvela, Päivi
AU - Laluc, Mathias
AU - Peixoto, Andreia F.
AU - Kholkina, Ekaterina
AU - Sandberg, Thomas
AU - Aho, Atte
AU - Volcho, Konstantin
AU - Salakhutdinov, Nariman
AU - Freire, Cristina
AU - Sidorenko, Alexander Yu
AU - Murzin, Dmitry Yu
N1 - Publisher Copyright: © 2019 Elsevier B.V. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.
PY - 2019/11/1
Y1 - 2019/11/1
N2 - Prins cyclization of (-)-isopulegol with benzaldehyde was investigated with sulphur containing halloysite nanotubes, K10 clays and Cloisite clays. The catalysts were characterized by TEM, SEM, XRD, XPS, pyridine adsorption desorption by FTIR, nitrogen adsorption. The most active catalyst was K10 modified with chlorosulphonic acid giving 95% selectivity to the desired chromenol at 90% conversion and 30 °C. Selectivity to chromenol was increasing with increasing Lewis acid site concentration while no linear correlation of chromenol selectivity with the Brønsted acid sites concentration was observed. The diastereoisomer R/S ratio of chromenols was the highest, 11.5, at 70 °C and 90% conversion over sulphur modified halloysite nanotubes exhibiting rather low acidity. A higher stability of the R-isomer confirmed by quantum mechanical calculations can partially explain preferential formation of the R diastereomer. Successful catalyst reuse was demonstrated with the best performing catalyst, organosilylated sulphur containing K10.
AB - Prins cyclization of (-)-isopulegol with benzaldehyde was investigated with sulphur containing halloysite nanotubes, K10 clays and Cloisite clays. The catalysts were characterized by TEM, SEM, XRD, XPS, pyridine adsorption desorption by FTIR, nitrogen adsorption. The most active catalyst was K10 modified with chlorosulphonic acid giving 95% selectivity to the desired chromenol at 90% conversion and 30 °C. Selectivity to chromenol was increasing with increasing Lewis acid site concentration while no linear correlation of chromenol selectivity with the Brønsted acid sites concentration was observed. The diastereoisomer R/S ratio of chromenols was the highest, 11.5, at 70 °C and 90% conversion over sulphur modified halloysite nanotubes exhibiting rather low acidity. A higher stability of the R-isomer confirmed by quantum mechanical calculations can partially explain preferential formation of the R diastereomer. Successful catalyst reuse was demonstrated with the best performing catalyst, organosilylated sulphur containing K10.
KW - Chromenols
KW - Isopulegol
KW - Organosulfonic clays
KW - Prins reaction
KW - ACID
KW - OCTAHYDRO-2H-CHROMEN-4-OL
KW - ESTERIFICATION
KW - ISOPULEGOL
KW - ANALGESIC ACTIVITY
KW - MECHANICAL-PROPERTIES
KW - NANOCOMPOSITES
KW - MODIFIED HALLOYSITE NANOTUBES
KW - ABSORPTION
KW - CATALYSTS
UR - http://www.scopus.com/inward/record.url?scp=85071402620&partnerID=8YFLogxK
U2 - 10.1016/j.mcat.2019.110569
DO - 10.1016/j.mcat.2019.110569
M3 - Article
AN - SCOPUS:85071402620
VL - 478
JO - Molecular Catalysis
JF - Molecular Catalysis
SN - 2468-8231
M1 - 110569
ER -
ID: 21343933