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Preparation of chiral isobenzofurans from 3-carene in the presence of modified clays. / Sidorenko, A. Yu; Il'ina, I. V.; Kravtsova, A. V. et al.

In: Molecular Catalysis, Vol. 459, 01.11.2018, p. 38-45.

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

Harvard

Sidorenko, AY, Il'ina, IV, Kravtsova, AV, Aho, A, Ardashov, OV, Li-Zhulanov, NS, Volcho, KP, Salakhutdinov, NF, Murzin, DY & Agabekov, VE 2018, 'Preparation of chiral isobenzofurans from 3-carene in the presence of modified clays', Molecular Catalysis, vol. 459, pp. 38-45. https://doi.org/10.1016/j.mcat.2018.07.025

APA

Sidorenko, A. Y., Il'ina, I. V., Kravtsova, A. V., Aho, A., Ardashov, O. V., Li-Zhulanov, N. S., Volcho, K. P., Salakhutdinov, N. F., Murzin, D. Y., & Agabekov, V. E. (2018). Preparation of chiral isobenzofurans from 3-carene in the presence of modified clays. Molecular Catalysis, 459, 38-45. https://doi.org/10.1016/j.mcat.2018.07.025

Vancouver

Sidorenko AY, Il'ina IV, Kravtsova AV, Aho A, Ardashov OV, Li-Zhulanov NS et al. Preparation of chiral isobenzofurans from 3-carene in the presence of modified clays. Molecular Catalysis. 2018 Nov 1;459:38-45. doi: 10.1016/j.mcat.2018.07.025

Author

Sidorenko, A. Yu ; Il'ina, I. V. ; Kravtsova, A. V. et al. / Preparation of chiral isobenzofurans from 3-carene in the presence of modified clays. In: Molecular Catalysis. 2018 ; Vol. 459. pp. 38-45.

BibTeX

@article{077a52306c41406fb0de8215a22f1958,
title = "Preparation of chiral isobenzofurans from 3-carene in the presence of modified clays",
abstract = "Isomerization of 3-carene to the reaction mixture, containing 2-carene and its further utilization in the synthesis of chiral isobenzofurans, was investigated in the presence of acid-modified clays at 140 °C. The catalysts were characterized by XRF, FTIR with pyridine and nitrogen adsorption. Quantification of the effect of the type and concentration of acid sites in different clays comprising commercial montmorillonite and natural illite on the yield of 2-carene as well as by-products was obtained for the first time. It was established that selectivity to 2-carene decreased with an increase of the Lewis to Br{\o}nsted acid sites ratio. The largest amount of 2-carene in the mixture (15.0 wt.%) with the highest ratio of 2-carene to menthadienes (0.63) was observed at 50% 3-carene conversion over a commercial montmorillonite K-30 clay, which has a moderate (100 μmol/g) acidity. It was demonstrated for the first time that the mixture containing 2-carene can be effectively used as a starting material in the reaction with vanillin resulting in chiral isobenzofurans. The products obtained in this reaction exhibit neuroprotective activity in an animal Parkinson's disease model. It was established that isobenzofurans yield decreased with an increase in the Lewis to Br{\o}nsted acid sites ratio. The largest yield of these products was obtained in the presence of a commercial K-10 clay (59.8%), which is higher than using 2-carene per se. Catalytic synthesis of isobenzofurans based on a readily available monoterpene 3-carene instead of expensive 2-carene was thus developed.",
keywords = "2-Carene, 3-Carene, Clays, Isobenzofuran, Isomerization, K-10 montmorillonite, ACID CATALYSTS, OCTAHYDRO-2H-CHROMEN-4-OL, ISOMERIZATION, ALDEHYDES, ISOPULEGOL, ANALGESIC ACTIVITY, MONOTERPENES, (+)-3-CARENE, ALPHA-PINENE, VAPOR-PHASE",
author = "Sidorenko, {A. Yu} and Il'ina, {I. V.} and Kravtsova, {A. V.} and A. Aho and Ardashov, {O. V.} and Li-Zhulanov, {N. S.} and Volcho, {K. P.} and Salakhutdinov, {N. F.} and Murzin, {D. Yu} and Agabekov, {V. E.}",
note = "Publisher Copyright: {\textcopyright} 2018 Elsevier B.V.",
year = "2018",
month = nov,
day = "1",
doi = "10.1016/j.mcat.2018.07.025",
language = "English",
volume = "459",
pages = "38--45",
journal = "Molecular Catalysis",
issn = "2468-8231",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Preparation of chiral isobenzofurans from 3-carene in the presence of modified clays

AU - Sidorenko, A. Yu

AU - Il'ina, I. V.

AU - Kravtsova, A. V.

AU - Aho, A.

AU - Ardashov, O. V.

AU - Li-Zhulanov, N. S.

AU - Volcho, K. P.

AU - Salakhutdinov, N. F.

AU - Murzin, D. Yu

AU - Agabekov, V. E.

N1 - Publisher Copyright: © 2018 Elsevier B.V.

PY - 2018/11/1

Y1 - 2018/11/1

N2 - Isomerization of 3-carene to the reaction mixture, containing 2-carene and its further utilization in the synthesis of chiral isobenzofurans, was investigated in the presence of acid-modified clays at 140 °C. The catalysts were characterized by XRF, FTIR with pyridine and nitrogen adsorption. Quantification of the effect of the type and concentration of acid sites in different clays comprising commercial montmorillonite and natural illite on the yield of 2-carene as well as by-products was obtained for the first time. It was established that selectivity to 2-carene decreased with an increase of the Lewis to Brønsted acid sites ratio. The largest amount of 2-carene in the mixture (15.0 wt.%) with the highest ratio of 2-carene to menthadienes (0.63) was observed at 50% 3-carene conversion over a commercial montmorillonite K-30 clay, which has a moderate (100 μmol/g) acidity. It was demonstrated for the first time that the mixture containing 2-carene can be effectively used as a starting material in the reaction with vanillin resulting in chiral isobenzofurans. The products obtained in this reaction exhibit neuroprotective activity in an animal Parkinson's disease model. It was established that isobenzofurans yield decreased with an increase in the Lewis to Brønsted acid sites ratio. The largest yield of these products was obtained in the presence of a commercial K-10 clay (59.8%), which is higher than using 2-carene per se. Catalytic synthesis of isobenzofurans based on a readily available monoterpene 3-carene instead of expensive 2-carene was thus developed.

AB - Isomerization of 3-carene to the reaction mixture, containing 2-carene and its further utilization in the synthesis of chiral isobenzofurans, was investigated in the presence of acid-modified clays at 140 °C. The catalysts were characterized by XRF, FTIR with pyridine and nitrogen adsorption. Quantification of the effect of the type and concentration of acid sites in different clays comprising commercial montmorillonite and natural illite on the yield of 2-carene as well as by-products was obtained for the first time. It was established that selectivity to 2-carene decreased with an increase of the Lewis to Brønsted acid sites ratio. The largest amount of 2-carene in the mixture (15.0 wt.%) with the highest ratio of 2-carene to menthadienes (0.63) was observed at 50% 3-carene conversion over a commercial montmorillonite K-30 clay, which has a moderate (100 μmol/g) acidity. It was demonstrated for the first time that the mixture containing 2-carene can be effectively used as a starting material in the reaction with vanillin resulting in chiral isobenzofurans. The products obtained in this reaction exhibit neuroprotective activity in an animal Parkinson's disease model. It was established that isobenzofurans yield decreased with an increase in the Lewis to Brønsted acid sites ratio. The largest yield of these products was obtained in the presence of a commercial K-10 clay (59.8%), which is higher than using 2-carene per se. Catalytic synthesis of isobenzofurans based on a readily available monoterpene 3-carene instead of expensive 2-carene was thus developed.

KW - 2-Carene

KW - 3-Carene

KW - Clays

KW - Isobenzofuran

KW - Isomerization

KW - K-10 montmorillonite

KW - ACID CATALYSTS

KW - OCTAHYDRO-2H-CHROMEN-4-OL

KW - ISOMERIZATION

KW - ALDEHYDES

KW - ISOPULEGOL

KW - ANALGESIC ACTIVITY

KW - MONOTERPENES

KW - (+)-3-CARENE

KW - ALPHA-PINENE

KW - VAPOR-PHASE

UR - http://www.scopus.com/inward/record.url?scp=85052880420&partnerID=8YFLogxK

U2 - 10.1016/j.mcat.2018.07.025

DO - 10.1016/j.mcat.2018.07.025

M3 - Article

AN - SCOPUS:85052880420

VL - 459

SP - 38

EP - 45

JO - Molecular Catalysis

JF - Molecular Catalysis

SN - 2468-8231

ER -

ID: 16481844