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Int. J. Mol. Sci. 2014, 15(5), 8656-8666; doi:10.3390/ijms15058656
Article

Geminal Brønsted Acid Ionic Liquids as Catalysts for the Mannich Reaction in Water

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Received: 21 March 2014 / Revised: 30 April 2014 / Accepted: 6 May 2014 / Published: 15 May 2014
(This article belongs to the Special Issue Ionic Liquids 2014 & Selected Papers from ILMAT 2013)
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Abstract

Quaternary ammonium geminal Brønsted acid ionic liquids (GBAILs) based on zwitterionic 1,2-bis[N-methyl-N-(3-sulfopropyl)-alkylammonium]ethane (where the carbon number of the alkyl chain is 4, 8, 10, 12, 14, 16, or 18) and p-toluenesulfonic acid monohydrate were synthesized. The catalytic ionic liquids were applied in three-component Mannich reactions with an aldehyde, ketone, and amine at 25 °C in water. The effects of the type and amount of catalyst and reaction time as well as the scope of the reaction were investigated. Results showed that GBAIL-C14 has excellent catalytic activity and fair reusability. The catalytic procedure was simple, and the catalyst could be recycled seven times via a simple separation process without noticeable decreases in catalytic activity.
Keywords: Mannich reaction; geminal ionic liquid; water; catalyst; emulsion Mannich reaction; geminal ionic liquid; water; catalyst; emulsion
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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He, L.; Qin, S.; Chang, T.; Sun, Y.; Zhao, J. Geminal Brønsted Acid Ionic Liquids as Catalysts for the Mannich Reaction in Water. Int. J. Mol. Sci. 2014, 15, 8656-8666.

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