Premium
Amides of a ‐sulfonated palmitic and stearic acids
Author(s) -
Weil J. K.,
Stirton A. J.,
Bistline R. G.
Publication year - 1960
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02631770
Subject(s) - chemistry , diethanolamine , ethanolamine , solubility , ethylamine , sodium , aqueous solution , stearic acid , organic chemistry , thionyl chloride , solvent , ammonium , inorganic chemistry , nuclear chemistry , chloride
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.