Summary
Carboxylic acid amides of α-sulfopalmitic and α-sulfostearic acids were prepared from ammonia, ethylamine, ethanolamine, isopropylalcoholamine, diethanolamine, and N-methyltaurine, and were isolated as the sodium, ammonium, or ethanolammonium salt.
A satisfactory method was found to be the reaction of the sulfocarboxylic acid with an excess of thionyl chloride, and further reaction of the acid chloride with an amine in a chlorinated solvent. More work is needed on the application of direct amidation methods to the preparation of these compounds.
The solubility of the α-sulfonated amides increased with substitution of alkyl, hydroxyalkyl, and sulfoalkyl groups at the nitrogen atom. Ethanolammonium N-hydroxyethyl-α-sulfopalmitamide, ethanolammonium N-hydroxyethyl-α-sulfostearamide, sodium N-(2-hydroxypropyl)-α-sulfostearamide, sodium di-(N-hydroxyethyl)-α-sulfostearamide, and disodium N-methyl,N-(2-sulfoethyl)-α-sulfostearamide have aqueous solubility in excess of 10% at room temperature.
Most of the sodium salts of the α-sulfonated amides have good or excellent stability to calcium and other divalent ions and are excellent lime soap dispersing agents.
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Enstern Utilization Research and Development Division, Agricultural Research Service, U. S. Department of Agriculture.
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Weil, J.K., Stirton, A.J. & Bistline, R.G. Amides ofa-sulfonated palmitic and stearic acids. J Am Oil Chem Soc 37, 295–297 (1960). https://doi.org/10.1007/BF02631770
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DOI: https://doi.org/10.1007/BF02631770