Even chain sodium alkanesulfonates from the Strecker reaction, odd chain sodium alkanesulfonates from the alkaline decarboxylation of ॅ‐sulfo acids, and sodium 1‐hydroxy‐2‐alkanesulfonates from the reduction of esters of ॅ‐sulfo acids were compared with respect to Krafft point, critical micelle concentration, detergency and foam height. Sodium alkanesulfonates and crude fusion products from the ॅ‐sulfo acids (mixtures of alkanesulfonates of one less carbon atom with a lesser amount of a soap of two less carbon atoms) are more soluble and have better detergent and foaming properties. Sodium 1‐hydroxy‐2‐alkanesulfonates resemble monosodium salts of ॅ‐sulfo acids.Alkanesulfonic acids and 1‐hydroxy‐2‐alkane‐sulfonic acids obtained from the sodium salts by ion exchange have lower Krafft points and are more readily soluble. The critical micelle concentrations of 1‐hydroxy‐2‐alkanesulfonic acids and ॅ‐sulfo acids are nearly the same and about equal to those of alkanesulfonic acids of one less carbon atom.

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.

SummaryA laboratory survey of the properties of a series of ethenoxylated fatty acids and alcohols containing about 10, 15, 20, 30, and 40 ethenoxy groups per molecule has brought together information on solubility, cloud point, surface and interfacial tension, detergency, and wetting, foaming and emulsifying properties.Ethenoxylated alcohols were generally more soluble and had better wetting and foaming properties than the acids. Ethenoxylated acids had generally lower surface and interfacial tension values. Both types of nonionics appeared to be excellent emulsifying agents. Most of the ethenoxylated acids and alcohols were equally effective as built detergents. Built ethenoxylated oleic acid (n=10) and built hydroxy‐, dihydroxy‐, phenyl‐, and xylylstearic acids (n=20) were the best detergents.Nonionic surface‐active agents derivable from animal fats appeared to have an optimum range in the average number of ethenoxy groups per molecule, with respect to certain properties. The optimum was in the range of about 14 to 18 for wetting properties, the foaming properties of ethenoxylated alcohols, and the interfacial tension of ethenoxylated acids. This range is about equal to the value suggested for adequate solubility [3 less than the number of carbon atoms in the parent alcohol (3)] but somewhat higher than the general rule for maximum detergency [2/3 the number of carbon atoms in the parent acid or alcohol (1,5)].The rate of the reaction of octadecanol and stearic acid with ethylene oxide was compared. The alcohol reacted faster, in a non‐specific manner. The acidity of the carboxyl group of stearic acid promoted conversion to ethylene glycol monostearate before further ethenoxylation occurred. After disappearance of the carboxylic acid the rate of the reaction of the ethenoxylated acid approached that for octadecanol. A reaction mechanism consistent with these results is proposed.

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K NOWLEDGE concerning the oxidation of the individual components of lard as well as their mixtures should be of value in disclosing the course of the development of oxidative rancidity. Furthermore the behavior of antioxidants with each component may help to reveal the nature of their protective action with lard.Although the exact individual components of lard are not available, they may be represented, approximately, by methyl oleate, methyl stearate, and methyl linoteate. A number of workers have investigated the oxygen absorption of fat acids and esters (1-12), but no single investigation has included all the methyl esters of the fat acids of lard and mixtures of these methyl esters.The usefulness of the Barcroft-Warburg apparatus in the study of the autoxidation of fats has been demonstrated (13,14) and it was our purpose to apply this convenient method to the methyl esters of fat acids representing the components of lard. Accordingly methyl oleate, methyl stearate, methyl linoleate, the distilled methyl esters of lard, and various mixtures of the individual methyl esters were prepared, and their oxygen absorption at 100 ° C. was determined. In addition, for general comparative purposes, measurements of the oxygen absorption of methyl linolenate were included.A group of antioxidants was evaluated with methyl linoleate, methyl oleate, methyl stearate, and the distilled methyl esters of lard. The antioxidants were a-tocopherol, nordihydroguaiaretic acid (NDGA), propyl gallate, benzylhydroquinone, and synergistic combinations with citric acid, d-isoascorbyl palmitate, and lecithin.As might be expected, methyl linolenate, methyl linoleate, the distilled methyl esters of lard, methyl oleate, and methyl stearate absorbed oxygen und developed peroxides, at relative rates in the order named. Mixtures of substrates absorbed oxygen at a rate which could be approximately predicted from the rate of oxygen absorption of the individual components. The order of effectiveness of the antioxidants varied somewhat with the different substrates but in each case the combinations of nordihydroguaiaretic acid and of propyl gallate with citric acid were the most powerful antioxidants. Preparation of the SubstratesN ETHYL oleate was prepared from the methyl esters of lard by a series of low-temperature fractional crystallizations and fractional vacuum distillations (15). The final product had an iodine nnmber of 85.5 (Wijs).Methyl stearate was prepared from hydrogenated soybean oil fat acids by esterification with methyl * One of the laboratories of the Bureau of Agricultural and Industrial Chemistry, Agricultural Research Administration, United States Department of Agriculture.alcohol; sulfuric acid was used as a catalyst. After fractional vacuum distillation and recrystallization the methyl stearate had a saponification equivalent of 300.4; a melting point of 39.0-39.4 ° ; and an iodine number of zero (Wijs).Methyl linoleate was prepared from the unsaturated fat acids of cottonseed oil (16) by the method of Rollett (17). Methyl lin...