Micellar-Improved Synthesis of bis-Quaternary Ammonium Salts by the Epichlorohydrin Route
A convenient procedure for the synthesis of bis-quaternary ammonium salts from long-chain alkyldimethylamines and epichlorohydrin is studied. An improved preparation of bis-quaternary ammonium salts from N,N-dimethyloctylamine, N,N-dimethyldodecylamine or N,N-dimethyloleylamine, their amine hydrochl...
| Autores: | , , , |
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| Formato: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2003 |
| País: | Argentina |
| Recursos: | Consejo Nacional de Investigaciones Científicas y Técnicas |
| Repositorio: | CONICET Digital (CONICET) |
| Idioma: | inglés |
| OAI Identifier: | oai:ri.conicet.gov.ar:11336/28566 |
| Acesso em linha: | http://hdl.handle.net/11336/28566 |
| Access Level: | acceso abierto |
| Palavra-chave: | Aqueous Micellar Medium Bis-Quaternary Ammonium Salt Epichlorohydrin Functional Surfactant Quaternization Reaction https://purl.org/becyt/ford/2.4 https://purl.org/becyt/ford/2 |
| Resumo: | A convenient procedure for the synthesis of bis-quaternary ammonium salts from long-chain alkyldimethylamines and epichlorohydrin is studied. An improved preparation of bis-quaternary ammonium salts from N,N-dimethyloctylamine, N,N-dimethyldodecylamine or N,N-dimethyloleylamine, their amine hydrochlorides, and epichlorohydrin can be achieved by carrying out the reaction in an aqueous micellar medium. The amine hydrochlorides are used as functional surfactants to produce the self-micellization and solubilization of reactants. The formation of micelles is a necessary condition for a successful quaternization. Comparison of the quaternization performance in ethanol, ethanol/water mixtures, and aqueous micellar medium leads to the conclusion that this micellar-improved synthesis enables easier and cheaper access to bis-quaternary ammonium salts by avoiding the formation of the mono-quaternary ammonium salts as intermediates, and by using water as solvent under mild reaction conditions. Mechanistic aspects of the quaternization reaction in micellized medium are also suggested. |
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