Effect of acid modification of kaolin and metakaolin on Bronsted acidity and catalytic properties in the synthesis of octahydro-2H-chromen-4-ol from vanillin and isopulegol

Effect of acid modification of kaolin and metakaolin on Bronsted acidity and catalytic properties in the synthesis of octahydro-2H-chromen-4-ol from vanillin and isopulegol Full article

Journal

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

Output data

Year: 2016, Volume: 414, Pages: 160-166 Pages count : 7 DOI: 10.1016/j.molcata.2016.01.010

Tags

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

Authors

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

Affiliations

1	(Данные Web of science) Boreskov Inst Catalysis SB RAS, Prospekt Akad Lavrentieva 5, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, St Pirogova 2, Novosibirsk 630090, Russia
3	(Данные Web of science) Novosibirsk State Tech Univ, Prospekt K Marksa 20, Novosibirsk 630092, Russia
4	(Данные Web of science) Novosibirsk Inst Organ Chem SB RAS, Prospect Akad Lavrentieva 9, Novosibirsk 630090, Russia
5	(Данные Web of science) Inst Geol Ore Deposits Petrog Mineral & Geochem R, Pr Staromonetny 35, Moscow 119017, Russia
6	(Данные Web of science) Moscow MV Lomonosov State Univ, Leninskie Gory 1, Moscow 119991, Russia
7	(Данные Web of science) Univ Publ Navarra, Dept Appl Chem, Los Acebos Bldg,Campus Arrosadia S-N, Pamplona 31006, Spain
8	(Данные Web of science) Univ Salamanca, Dept Inorgan Chem, E-37008 Salamanca, Spain

Natural kaolin and the metakaolin obtained by calcination of kaolin at 650 degrees C were chemically activated using 0.25-3.0 mol/dm(3) HCl solutions. Structural and textural properties of samples were characterized by X-ray diffraction, elemental analysis and N-2-adsorption/desorption analyses. The amount of Bronsted acid sites (BAS) was determined by infrared spectroscopy using pyridine as probe molecule. The amount of BAS for kaolin rose with increasing HCl concentration up to 1.0 M, and decreased for higher concentrations, that is related with the leaching of Al from the solid. Effect of HCl concentration on amount of BAS was negligible for metakaolin. 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 50 degrees C. The reaction rate and the selectivity toward octahydro-2H-chromen-4-ol depended on the Bronsted acidity, structural and textural properties of the catalysts. The reaction rate in the presence of kaolin modified by HCl correlated with the amount of BAS. HCl-kaolin samples were more active compared with HCl-metakaolin, while selectivity reaction toward octahydro-2H-chromen-4-ol was larger in the presence of HCl-metakaolin. (C) 2016 Elsevier B.V. All rights reserved.

Timofeeva M.N. , Panchenko V.N. , Volcho K.P. , Zakusin S.V. , Krupskaya V.V. , Gil A. , Mikhalchenko O.S. , Vicente M.A.
Effect of acid modification of kaolin and metakaolin on Bronsted acidity and catalytic properties in the synthesis of octahydro-2H-chromen-4-ol from vanillin and isopulegol
Journal of Molecular Catalysis A: Chemical. 2016. V.414. P.160-166. DOI: 10.1016/j.molcata.2016.01.010 WOS Scopus РИНЦ OpenAlex

Published print:

Apr 1, 2016

Web of science:	WOS:000370914500019
Scopus:	2-s2.0-84955450079
Elibrary:	26843853
OpenAlex:	W2233627262

DB	Citing
Web of science	33
Scopus	37
Elibrary	37
OpenAlex	36