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Issue 10, 2017

Continuous niobium phosphate catalysed Skraup reaction for quinoline synthesis from solketal

Author affiliations

Abstract

Solketal is derived from the reaction of acetone with glycerol, a by-product of the biodiesel industry. We report here the continuous reaction of solketal with anilines over a solid acid niobium phosphate (NbP), for the continuous generation of quinolines in the well-established Skraup reaction. This study shows that NbP can catalyse all the stages of this multistep reaction at 250 °C and 10 MPa pressure, with a selectivity for quinoline of up to 60%. We found that the catalyst eventually deactivates, most probably via a combination of coking and reduction processes but nevertheless we show the promise of this approach. We demonstrate here the application of our approach to synthesize both mono- and bis-quinolines from the commodity chemical, 4,4′-methylenedianiline.

Graphical abstract: Continuous niobium phosphate catalysed Skraup reaction for quinoline synthesis from solketal

Supplementary files

Article information


Submitted
14 Nov 2016
Accepted
06 Apr 2017
First published
28 Apr 2017

Green Chem., 2017,19, 2439-2447
Article type
Paper

Continuous niobium phosphate catalysed Skraup reaction for quinoline synthesis from solketal

J. Jin, S. Guidi, Z. Abada, Z. Amara, M. Selva, M. W. George and M. Poliakoff, Green Chem., 2017, 19, 2439 DOI: 10.1039/C6GC03140D

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