Synthesis of octahydro-2H-chromen-4-ol from vanillin and isopulegol over acid modified montmorillonite clays: Effect of acidity on the Prins cyclization

Synthesis of octahydro-2H-chromen-4-ol from vanillin and isopulegol over acid modified montmorillonite clays: Effect of acidity on the Prins cyclization Научная публикация

Журнал

Journal of Molecular Catalysis A: Chemical
ISSN: 1381-1169

Вых. Данные

Год: 2015, Том: 398, Страницы: 26-34 Страниц : 9 DOI: 10.1016/j.molcata.2014.11.016

Ключевые слова

Acid-activated montmorillonite; Prins cyclization reaction; Octahydro-2H-chromen-4-ol; (-)-Isopulegol; Vanillin

Авторы

Timofeeva Maria N. ^1,2,3 , Volcho Konstantin P. ^2,4 , Mikhalchenko Oksana S. ² , Panchenko Valentina N. ^1,2 , Krupskaya Victoria V. ^5,6 , Tsybulya Sergey V. ^1,2 , Gil Antonio ⁷ , Vicente Miguel A. ⁸ , Salakhutdinov Nariman F. ^2,4

Организации

1	(Данные Web of science) SB RAS, Boreskov Inst Catalysis, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia
3	(Данные Web of science) Novosibirsk State Tech Univ, Novosibirsk 630092, Russia
4	(Данные Web of science) SB RAS, Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
5	(Данные Web of science) RAS, Inst Geol Ore Deposits Petrog Mineral & Geochem, Moscow 119017, Russia
6	(Данные Web of science) Moscow MV Lomonosov State Univ, Moscow 119991, Russia
7	(Данные Web of science) Univ Publ Navarra, Dept Appl Chem, Pamplona 31006, Spain
8	(Данные Web of science) Univ Salamanca, Dept Inorgan Chem, E-37008 Salamanca, Spain

Two calcium-rich natural layered aluminosilicates containing 90-95 wt.% montmorillonite were chemically activated using 0.125-3.0 M HCl solutions. Structural and textural properties were characterized by X-ray diffraction, elemental analysis and N-2-adsorption/desorption analyses. According to infrared spectroscopy using pyridine as probe molecule, the amount of Bronsted acid sites increased when increasing HCl concentration. The catalytic performance of these materials was investigated in the Prins cyclization of (-)-isopulegol with vanillin to form octahydro-2H-chromen-4-ol, carried out in toluene at 35 degrees C. It was found that the amount of Bronsted acid sites and the microporosity of the catalysts are key factors for the control of the reaction rate and the selectivity towards octahydro-2H-chromen-4-ol. (C) 2014 Elsevier B.V. All rights reserved.

Timofeeva M.N. , Volcho K.P. , Mikhalchenko O.S. , Panchenko V.N. , Krupskaya V.V. , Tsybulya S.V. , Gil A. , Vicente M.A. , Salakhutdinov N.F.
Synthesis of octahydro-2H-chromen-4-ol from vanillin and isopulegol over acid modified montmorillonite clays: Effect of acidity on the Prins cyclization
Journal of Molecular Catalysis A: Chemical. 2015. V.398. P.26-34. DOI: 10.1016/j.molcata.2014.11.016 WOS Scopus РИНЦ

Опубликована в печати:

1 мар. 2015 г.

Web of science	WOS:000352115600004
Scopus	2-s2.0-84919345048
РИНЦ	24019505
OpenAlex	W2010932221