Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
Preparation of chiral isobenzofurans from 3-carene in the presence of modified clays. / Sidorenko, A. Yu; Il'ina, I. V.; Kravtsova, A. V. и др.
в: Molecular Catalysis, Том 459, 01.11.2018, стр. 38-45.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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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