Continuous niobium phosphate catalysed Skraup reaction for quinoline synthesis from solketal

Jin, Jing; Guidi, Sandro; Amara, Zacharias; Selva, Maurizio; George, Michael W.; Poliakoff, Martyn

Abstract

Solketal is derived from the reaction of acetone with glycerol, a by-product 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 the well-established Skraup reaction. This study shows that NbP can catalyse all 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 demonstrated here the application of our approach to synthesize both mono- and bis-quinolines from the commodity chemical, 4,4’-methylenedianiline.

Citation

Jin, J., Guidi, S., Amara, Z., Selva, M., George, M. W., & Poliakoff, M. (2017). Continuous niobium phosphate catalysed Skraup reaction for quinoline synthesis from solketal. Green Chemistry, 19(10), 2439-2447. https://doi.org/10.1039/C6GC03140D

• Journal Article Type: Article
• Acceptance Date: Apr 6, 2017
• Publication Date: Apr 28, 2017
• Deposit Date: Jul 17, 2017
• Publicly Available Date: Jul 17, 2017
• Journal: Green Chemistry
• Print ISSN: 1463-9262
• Electronic ISSN: 1463-9270
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 19
• Issue: 10
• Pages: 2439-2447
• DOI: https://doi.org/10.1039/C6GC03140D
• Keywords: Niobium phosphate, acid-catalysed, quinoline, Skraup reaction, Indole, Continuous
• Public URL: https://nottingham-repository.worktribe.com/output/857721
• Publisher URL: http://pubs.rsc.org/en/Content/ArticleLanding/2017/GC/C6GC03140D#!divAbstract
• Additional Information: 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 Reproduced from Green Chemistry with permission from The Royal Society of Chemistry.
• Contract Date: Jul 17, 2017