4.8 Article

Continuous niobium phosphate catalysed Skraup reaction for quinoline synthesis from solketal

Journal

GREEN CHEMISTRY
Volume 19, Issue 10, Pages 2439-2447

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c6gc03140d

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Funding

  1. Companhia Brasileira de Metalurgia e Mineracao (CBMM)

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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 degrees 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.

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