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14 November 2019

Aqueous Micellar Systems Formed by Surfactant Ionic Liquids. Application in Diels-Alder Reactions †

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and
IQAL (UNL-CONICET), Laboratorio Fisicoquímica Orgánica, Facultad de Ingeniería Química, University Nacional del Litoral, Santiago del Estero 2829, Santa Fe 3000, Argentina
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Authors to whom correspondence should be addressed.
Presented at the 23rd International Electronic Conference on Synthetic Organic Chemistry, 15 November–15 December 2019; Available online: https://ecsoc-23.sciforum.net/.

Abstract

In the present work, our objective is to take advantage of the property presented by Ionic Liquids (ILs) based on 1-alkyl-3-methylimidazolium cations by having amphiphilic character when the alkyl group is a long hydrocarbon chain. These ILs can act as surfactants forming micelles in aqueous solution. In this sense, the micellar effect on a Diels-Alder reaction (DA) was analyzed taken as a reference. The reactive system studied consists of maleic anhydride and isoprene, variables such as diene:dienophile ratio and reaction temperatura among the most important were optimized. N,N-dodecylmethylimidazolium bromide was used at the critical micellar concentration (CMC) of 1 × 10−2 M. These “new systems” microheterogeneous would allow, in addition to better solubilization of non-polar substrates, to adopt milder reaction conditions.

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