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Photosulfochlorination Synthesis and Physicochemical Properties of Methyl Ester Sulfonates Derived from Lauric and Myristic Acids

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Journal of Surfactants and Detergents

Abstract

The photosulfochlorination process has been used in earlier works to produce n-alkane sulfonates. In this work, this process was applied for the first time on lauric and myristic fatty acids, leading to methyl ester sulfonates (MESs). The operating conditions were optimized and the isolation method described. Apart from the known advantages of this reaction, namely the use of sulfuryl chloride, the visible light and short reaction time, this process led to a clear mono-sulfonate products and thus allowed avoiding the bleaching step. The chemical composition of these surfactants was determined and their structures characterized by Fourier transform infrared spectroscopy, liquid chromatography-electrospray ionization tandem mass spectrometry and proton nuclear magnetic resonance. The physicochemical properties of these surfactants such as surface tension, critical micelle concentration, maximum surface excess and minimum area per molecule of surfactant at the air/water interface were determined. The Krafft point was determined experimentally and compared to the MES literature data. The experimental and calculated hydrophilic–lipophilic balance values obtained compared well. The foaming power using Bartsch’s method was presented and the results obtained compared to those of similar structures and those of sodium dodecyl sulfate.

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Acknowledgments

The authors are grateful to Prof. María Rosa Infante, Department of Surfactant Technology, Institute of Advanced Chemistry of Catalonia-Spanich Council for Scientific Research (IQAC-CSIC), Barcelona, Spain, for the helpful discussions and advice concerning NMR measurements.

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Authors and Affiliations

  1. Laboratoire de Chimie Organique Appliquée, Faculté de Chimie, Université des Sciences et de la Technologie Houari Boumediene (USTHB), Bab Ezzouar, 16111, Algiers, Algeria

    Amel Asselah & Amel Tazerouti

  2. Département du Génie de l’Environnement, Faculté des Sciences de l’Ingénieur (FSI), Université M’Hamed Bougara de Boumerdes (UMBB), Avenue de l’Indépendance, 35000, Boumerdes, Algeria

    Amel Asselah

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  1. Amel Asselah
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  2. Amel Tazerouti
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Correspondence to Amel Tazerouti.

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Asselah, A., Tazerouti, A. Photosulfochlorination Synthesis and Physicochemical Properties of Methyl Ester Sulfonates Derived from Lauric and Myristic Acids. J Surfact Deterg 17, 1151–1160 (2014). https://doi.org/10.1007/s11743-014-1635-9

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  • DOI: https://doi.org/10.1007/s11743-014-1635-9

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