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Micellar-improved synthesis of bis-quaternary ammonium salts by the epichlorohydrin route

  • Published:
Journal of Surfactants and Detergents

Abstract

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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Abbreviations

b.p.:

boiling point

HPLC:

high-performance liquid chromatography

m.p.:

melting point

NMR:

nuclear magnetic resonance

UV:

ultraviolet

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Authors and Affiliations

  1. Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET), Technological Institute for Development of the Chemical Industry, Güemes 3450, 3000, Santa Fe, Argentina

    C. G. Ricci, M. I. Cabrera, J. A. Luna & R. J. Grau

  2. Universidad Nacional del Litoral (UNL), Technological Institute for Development of the Chemical Industry, Güemes 3450, 3000, Santa Fe, Argentina

    M. I. Cabrera, J. A. Luna & R. J. Grau

Authors
  1. C. G. Ricci
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  2. M. I. Cabrera
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  3. J. A. Luna
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  4. R. J. Grau
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Correspondence to R. J. Grau.

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Ricci, C.G., Cabrera, M.I., Luna, J.A. et al. Micellar-improved synthesis of bis-quaternary ammonium salts by the epichlorohydrin route. J Surfact Deterg 6, 231–237 (2003). https://doi.org/10.1007/s11743-003-0266-1

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  • DOI: https://doi.org/10.1007/s11743-003-0266-1

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