Continuous flow synthesis of β-amino α, β-unsaturated esters in aqueous medium : Green Processing and Synthesis

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Green Sciences

Green Processing and Synthesis

Editor-in-Chief: Hessel, Volker

Editorial Board Member: Akay, Galip / Arends, Isabel / Cann, Michael C. / Cheng, Yi / Cravotto, Giancarlo / Gruber-Wölfler, Heidrun / Kralisch, Dana / D. P. Nigam, Krishna / Saha, Basudeb / Serra, Christophe A. / Zhang, Wei


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Continuous flow synthesis of β-amino α, β-unsaturated esters in aqueous medium

Ramesh A. Joshi1 / Rohini R. Joshi1 / Jagdish Tibhe2 / Nayana T. Nivangune2 / 2

1Organic Chemistry Division, National Chemical Laboratory, Pune, 411008, India

2Chemical Engineering and Process Development Division, National Chemical Laboratory, Pune, 411008, India

Corresponding author

Citation Information: Green Processing and Synthesis. Volume 1, Issue 2, Pages 205–210, ISSN (Online) 2191-9550, ISSN (Print) 2191-9542, DOI: 10.1515/gps-2011-0002, April 2012

Publication History

Received:
2012-01-30
Accepted:
2012-03-06

Abstract

Continuous flow synthesis of many β-amino α, β-unsaturated esters has been demonstrated, through the reaction of a β-ketoester compound with ammonia and primary amines. Several combinations have been studied in detail in batch mode and a few have been taken for continuous flow synthesis based on their suitability. Upon studying the feasibility of continuous flow synthesis of different β-amino crotonates, the synthesis of methyl amino crotonate in the presence of a recyclable and reusable homogeneous acid catalyst has been studied in detail. Tubular reactors were seen to overcome the heat and mass transfer limitations, thereby providing a simple device for even a pilot scale production. A similar approach can be used for the synthesis of other β-amino crotonates. The continuous flow synthesis approach for producing methyl amino crotonate, in the absence of any external solvent, makes it a green process technology.

Keywords: β-amino crotonate; continuous flow synthesis; Hantzsch synthesis; microreactor

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