A series of esters of the general formula RCH(SO3Na)‐CO2R′ of 14–19 carbon atoms prepared by the α‐sulfonation of propionic, butyric, pelargonic, lauric, myristic, palmitie, and stearic acids and esterification with normal primary alcohols were compared for critical micelle concentration, surface and interfacial tension, Ca++ stability, wetting properties, foam height, detergency, and lime soap dispersing properties. Comparison of position isomers showed that as the hydrophilic portion moved from the center toward either end, cmc and wetting efficiency decreased, surface and interfacial tension increased, and Ca++ stability and lime soap dispersing properties improved.
A coconut oil fatty acid forerun sulfonated with SO3 vapor and esterified with 2‐ethylhexanol gave a product with useful wetting properties in soft and hard water.
Summary
Existing ultraviolet spectrophotometric methods have been modified for application primarily to the detection and estimation of low proportions of conjugated and nonconjugated unsaturated constituents in fats, oils, and soaps. The method is applicable also to fatty materials having high proportions of these constituents.
Modifications include corrections for absorption by interfering substances, use of alkaline glycerol as an isomerization medium in the analytical procedure, and correction of absorption data on the isomerized product for absorption by conjugated constituents in the material before isomerization.
The presence of small proportions of highly unsaturated conjugated and nonconjugated compounds is established in lards, tallows, tallow soaps, and highly purified esters and acids. Tall oil fatty acids are shown to contain approximately 10% of conjugated diene acids and a small amount of linolenic acid.
Direct sulfonation of higher fatty acids with sulfur trioxide or ehlorosulfonie acid, without use of solvent, is possible, but the product must then be isolated as the sodium salt. Use of a ehlori~l~ted soIvent permits ~solation of the ~-sulfo acid. Sulfonation with dioxane sulfur trioxide in place of sulfur trioxide gave a nearly colorless a-sulfostearie acid.Substituted stearic acids derived from oleic or elaidie acids (phenyl-, 9,10-dichloro-, and 9,10-dihydroxystearie acids) were a-sulfonated with dioxane sulfur trioxide. Solubility, detergent, and surface-active properties were examined and related to structure.The surface-active properties of sodium a-sulfopelargonie acid are not very evident, but the oetyl ester, with a much lower critic,fl micelle concentration (0.08% compared to 11.00%), was found to be a very efficient wetting agent.
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