Prins cyclization of (-)-isopulegol with benzaldehyde for production of chromenols over organosulfonic clays

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Prins cyclization of (-)-isopulegol with benzaldehyde for production of chromenols over organosulfonic clays. / Li-Zhulanov, Nikolai; Mäki-Arvela, Päivi; Laluc, Mathias et al.

In: Molecular Catalysis, Vol. 478, 110569, 01.11.2019.

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

Harvard

Li-Zhulanov, N, Mäki-Arvela, P, Laluc, M, Peixoto, AF, Kholkina, E, Sandberg, T, Aho, A, Volcho, K, Salakhutdinov, N, Freire, C, Sidorenko, AY & Murzin, DY 2019, 'Prins cyclization of (-)-isopulegol with benzaldehyde for production of chromenols over organosulfonic clays', Molecular Catalysis, vol. 478, 110569. https://doi.org/10.1016/j.mcat.2019.110569

APA

Li-Zhulanov, N., Mäki-Arvela, P., Laluc, M., Peixoto, A. F., Kholkina, E., Sandberg, T., Aho, A., Volcho, K., Salakhutdinov, N., Freire, C., Sidorenko, A. Y., & Murzin, D. Y. (2019). Prins cyclization of (-)-isopulegol with benzaldehyde for production of chromenols over organosulfonic clays. Molecular Catalysis, 478, [110569]. https://doi.org/10.1016/j.mcat.2019.110569

Vancouver

Li-Zhulanov N, Mäki-Arvela P, Laluc M, Peixoto AF, Kholkina E, Sandberg T et al. Prins cyclization of (-)-isopulegol with benzaldehyde for production of chromenols over organosulfonic clays. Molecular Catalysis. 2019 Nov 1;478:110569. doi: 10.1016/j.mcat.2019.110569

Author

Li-Zhulanov, Nikolai ; Mäki-Arvela, Päivi ; Laluc, Mathias et al. / Prins cyclization of (-)-isopulegol with benzaldehyde for production of chromenols over organosulfonic clays. In: Molecular Catalysis. 2019 ; Vol. 478.

BibTeX

@article{2163dbfea2f1481086c894f3694fc9a6,

title = "Prins cyclization of (-)-isopulegol with benzaldehyde for production of chromenols over organosulfonic clays",

abstract = "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 Br{\o}nsted 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.",

keywords = "Chromenols, Isopulegol, Organosulfonic clays, Prins reaction, ACID, OCTAHYDRO-2H-CHROMEN-4-OL, ESTERIFICATION, ISOPULEGOL, ANALGESIC ACTIVITY, MECHANICAL-PROPERTIES, NANOCOMPOSITES, MODIFIED HALLOYSITE NANOTUBES, ABSORPTION, CATALYSTS",

author = "Nikolai Li-Zhulanov and P{\"a}ivi M{\"a}ki-Arvela and Mathias Laluc and Peixoto, {Andreia F.} and Ekaterina Kholkina and Thomas Sandberg and Atte Aho and Konstantin Volcho and Nariman Salakhutdinov and Cristina Freire and Sidorenko, {Alexander Yu} and Murzin, {Dmitry Yu}",

year = "2019",

month = nov,

day = "1",

doi = "10.1016/j.mcat.2019.110569",

language = "English",

volume = "478",

journal = "Molecular Catalysis",

issn = "2468-8231",

publisher = "Elsevier",

}

RIS

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

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