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.
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.
SummaryThe alkali‐catalyzed reaction of ethylene oxide or propylene oxide with fatty acids was shown to be complex. Mono‐ and diesters were formed in comparable amounts even at an early stage when only about one equivalent of the cyclic ether had been condensed.The following compounds were isolated in a pure state: ethylene glycol monolaurate, ethylene glycol dilaurate, diethylene glycol dilaurate, ethylene glycol distearate, 1,2‐propylene glycol dilaurate, and 1,2‐propylene glycol distearate. A monoester from propylene oxide was shown to be a mixture of the 1‐and 2‐monolaurate [C11H23CO2CH2CHOHCH3 and C11H23CO2CH(CH3)CH2OH].
TETRAPHENYLDISTIBYL 1025 hydroxide was poured into a large beaker, heated almost to the boiling point and stirred vigorously with a mechanical stirrer. 4-Toluenesulfonechloride was then added in small portions. A vigorous reaction ensued with each addition of the chloride. After all of the material had been added the clear solution was cooled, whereupon the amide precipitated. The latter was separated, dissolved in boiling water and treated with charcoal. After filtration the sulfonamide separated from the cold, concentrated solution in the form of colorless crystals.
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