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Synthesis of 1,5-Benzodiazepine from 1,2-Phenylenediamine and Acetone in the Presence of Catalytic Systems Based on Montmorillonite: Effect of the Surface Acidity Full article

Journal Reaction Kinetics, Mechanisms and Catalysis
ISSN: 1878-5190 , E-ISSN: 1878-5204
Output data Year: 2019, Volume: 127, Number: 1, Pages: 41-52 Pages count : 12 DOI: 10.1007/s11144-018-1454-5
Tags Montmorillonite; Acid activation; Pillared clays; 1,5-Benzodiazepine; 1,2-Phenylenediamine; Acetone
Authors Timofeeva Maria N. 1,2 , Petrova Ekaterina A. 1,2 , Mel’gunova Elena A. 1 , Gil Antonio 3 , Vicente Miguel A. 4 , Panchenko Valentina N. 1,2
Affiliations
1 Boreskov Institute of Catalysis SB RAS, Prospekt Akad. Lavrentieva 5, 630090 Novosibirsk, Russian Federation
2 Novosibirsk State Technical University, Prospekt K. Marksa 20, 630092 Novosibirsk, Russian Federation
3 Departamento de Quımica Aplicada, Universidad Publica de Navarra, 31006 Pamplona, Spain
4 Departamento de Quımica Inorganica, Universidad de Salamanca, Salamanca, Spain

Funding (2)

1 Federal Agency for Scientific Organizations 0303-2016-0007
2 Santander Bank

Abstract: The effect of the surface acidity of catalytic systems based on montmorillonite (Mt) on the formation of 1,5-benzodiazepine from 1,2-phenylenediamine and acetone was investigated. Two strategies were used for designing the acid sites in the framework of a Mt. The Brønsted type catalysts were prepared by clay modification, changing the nature of the treating acid (0.25 M solutions of HNO3, H2SO4, HOAc and HCl) or the concentration of the solution (0.125–3.0 M HNO3). The Lewis type catalysts were prepared by the pillaring method using bulky Al-hydroxypolycations (OH−/Al3+ = 2.4 mol/mol) and mixed Al, Fe-polycations (OH−/(Al3+ + Fe3+) = 2.4 mol/mol, Al3+/Fe3+ = 12/1 mol/mol), followed by calcination at 500 °C in air. The acidity of the catalysts, i.e., the type and amount of acid sites, was found to play a critical role in the cyclocondensation and dictated the performance of the catalysts. Acid-activated Mt materials gave high yield of 1,5-benzodiazepine in a shorter reaction time compared to Al- and Fe, Al-pillared Mts.
Cite: Timofeeva M.N. , Petrova E.A. , Mel’gunova E.A. , Gil A. , Vicente M.A. , Panchenko V.N.
Synthesis of 1,5-Benzodiazepine from 1,2-Phenylenediamine and Acetone in the Presence of Catalytic Systems Based on Montmorillonite: Effect of the Surface Acidity
Reaction Kinetics, Mechanisms and Catalysis. 2019. V.127. N1. P.41-52. DOI: 10.1007/s11144-018-1454-5 WOS Scopus РИНЦ ANCAN OpenAlex
Dates:
Submitted: May 4, 2018
Accepted: Aug 3, 2018
Published online: Aug 17, 2018
Published print: Jun 15, 2019
Identifiers:
Web of science: WOS:000468213500005
Scopus: 2-s2.0-85052212267
Elibrary: 41796097
Chemical Abstracts: 2018:1550291
Chemical Abstracts (print): 170:574356
OpenAlex: W2887121606
Citing:
DB Citing
Scopus 5
Web of science 4
Elibrary 5
OpenAlex 4
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