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

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

2,* , 2
1 School of Chemical Engineering, Hebei University of Technology, Tianjin 300130, China 2 Key Laboratory for Resource Exploration Research of Hebei Province, Hebei University of Engineering, Handan 056038, China These authors contributed equally to this work.
* Authors to whom correspondence should be addressed.
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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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 (CC BY 3.0).

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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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