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 | Sciact - CRIS-system of Boreskov Institute of Catalysis

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

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.

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

Submitted:	May 4, 2018
Accepted:	Aug 3, 2018
Published online:	Aug 17, 2018
Published print:	Jun 15, 2019

Web of science:	WOS:000468213500005
Scopus:	2-s2.0-85052212267
Elibrary:	41796097
Chemical Abstracts:	2018:1550291
Chemical Abstracts (print):	170:574356
OpenAlex:	W2887121606

DB	Citing
Scopus	5
Web of science	4
Elibrary	5
OpenAlex	4