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Artículo

A suitable synthesis of azlactones (4-benzylidene-2-phenyloxazolin-5-ones and 4-alkylidene-2-phenyloxazolin-5-ones) catalyzed by silica-alumina supported heteropolyacids

Romanelli, Gustavo PabloIcon ; Autino, Juan Carlos; Vázquez, P.; Pizzio, Luis ReneIcon ; Blanco, Mirta NoemiIcon ; Caceres, Carmen VictoriaIcon
Fecha de publicación: 01/2009
Editorial: Elsevier Science
Revista: Applied Catalysis A: General
ISSN: 0926-860X
Idioma: Inglés
Tipo de recurso: Artículo publicado
Clasificación temática:
Otras Ciencias Químicas

Resumen

Eleven examples of azlactones (4-benzylidene-2-phenyloxazolin-5-ones and 4-alkylidene-2-phenyloxazolin-5-ones) were prepared via an Erlenmeyer-type synthesis from aromatic aldehydes, hippuric acid and acetic anhydride was added to the hot solution as a dehydrating agent. Molybdophosphoric or tungstophosphoric acids supported on silica-alumina, obtained by the sol-gel method, catalyze the reaction. The prepared catalysts were characterized by X-ray diffraction and diffuse reflectance spectroscopy. The specific surface area of the catalysts was determined by the nitrogen adsorption/desorption at 196 °C technique, and the catalyst acidity was measured by potentiometric titration with n-butylamine. The heteropolyacid amount removed from the catalysts during the leaching with toluene was lower than 1%. The products were obtained with high conversion and selectivity. The yields were in the 87-96% range for the majority of the selected samples, with the exception of the azlactones synthesized from 2-nitrobenzaldehyde and cyclohexanone, which gave yields in the 70-80% range. The same catalysts were used several times without appreciable loss of their catalytic activity. A rational mechanism for the azlactone formation catalyzed by the supported heteropolyacid is proposed. © 2008 Elsevier B.V. All rights reserved.
Palabras clave: Azlactones , Catalysis , Condensation , Cyclodehydration , Keggin Heteropolyacids , Oxazolones
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info:eu-repo/semantics/openAccess Excepto donde se diga explícitamente, este item se publica bajo la siguiente descripción: Creative Commons Attribution-NonCommercial-ShareAlike 2.5 Unported (CC BY-NC-SA 2.5)
Identificadores
URI: http://hdl.handle.net/11336/54059
DOI: https://dx.doi.org/10.1016/j.apcata.2008.10.003
URL: https://www.sciencedirect.com/science/article/pii/S0926860X08006273
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Articulos(CINDECA)
Articulos de CENTRO DE INV EN CS.APLICADAS "DR.JORGE J.RONCO"
Citación
Romanelli, Gustavo Pablo; Autino, Juan Carlos; Vázquez, P.; Pizzio, Luis Rene; Blanco, Mirta Noemi; et al.; A suitable synthesis of azlactones (4-benzylidene-2-phenyloxazolin-5-ones and 4-alkylidene-2-phenyloxazolin-5-ones) catalyzed by silica-alumina supported heteropolyacids; Elsevier Science; Applied Catalysis A: General; 352; 1-2; 1-2009; 208-213
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