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Issue 10, 2017
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Continuous niobium phosphate catalysed Skraup reaction for quinoline synthesis from solketal

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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

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Publication details

The article was received on 14 Nov 2016, accepted on 06 Apr 2017 and first published on 28 Apr 2017


Article type: Paper
DOI: 10.1039/C6GC03140D
Citation: Green Chem., 2017,19, 2439-2447
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    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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