Effect of Acid Modification of Kaolin and Metakaolin on Brønsted Acidity and Catalytic Properties in the Synthesis of Octahydro-2H-Chromen-4-ol from Vanillin and Isopulegol | Sciact - CRIS-system of Boreskov Institute of Catalysis

Effect of Acid Modification of Kaolin and Metakaolin on Brønsted 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

(-)-Isopulegol, Acid activation, Kaolin, Octahydro-2H-chromen-4-ol, Prins cyclization reaction, 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	Boreskov Institute of Catalysis SB RAS, Prospekt Akad. Lavrentieva 5, 630090, Novosibirsk, Russian Federation
2	Novosibirsk State University, St. Pirogova 2, 630090, Novosibirsk, Russian Federation
3	Novosibirsk State Technical University, Prospekt K. Marksa 20, 630092, Novosibirsk, Russian Federation
4	Novosibirsk Institute of Organic Chemistry SB RAS, Prospect Akad. Lavrentieva 9, 630090, Novosibirsk, Russian Federation
5	Institute of Geology of Ore Deposits, Petrography, Mineralogy and Geochemistry RAS, Pr. Staromonetny 35, 119017, Moscow, Russian Federation
6	Moscow State University, Leninskie Gory 1, 119991, Moscow, Russian Federation
7	Department of Applied Chemistry, Public University of Navarra, 31006 Pamplona, Spain
8	Department of Inorganic Chemistry, University of Salamanca, Salamanca, Spain

Funding (4)

1	Federal Agency for Scientific Organizations	V.44.2.12.
2	Russian Foundation for Basic Research	14-03-00854
3	Russian Foundation for Basic Research	14-05-00297
4	Ministry of Economic Affairs and Digital Transformation	MAT2013-47811-C2-1-R, MAT2013-47811-C2-2-R

Natural kaolin and the metakaolin obtained by calcination of kaolin at 650 ºC were chemically activated using 0.25-3.0 mol/dm3 HCl solutions. Structural and textural properties of samples were characterized by X-ray diffraction, elemental analysis and N2-adsorption/desorption analyses. The amount of Brønsted 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 ºC. The reaction rate and the selectivity towards 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 towards octahydro-2H-chromen-4-ol was larger in the presence of HCl-metakaolin

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 Brønsted 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 ANCAN OpenAlex

Submitted:	Aug 10, 2015
Accepted:	Jan 9, 2016
Published online:	Jan 13, 2016
Published print:	Apr 1, 2016

Web of science:	WOS:000370914500019
Scopus:	2-s2.0-84955450079
Elibrary:	26843853
Chemical Abstracts:	2016:169186
Chemical Abstracts (print):	164:264517
OpenAlex:	W2233627262

DB	Citing
Web of science	33
Scopus	37
Elibrary	37
OpenAlex	35