Surface tension studies on novel allylic mono‐and dihydroxy fatty compounds. A method to distinguisherythro/threo diastereomers

Abstract

AbstractThe suitability of the selenium dioxide/tert.‐butyl‐hydroperoxide system for obtaining allylic mono‐ and dihydroxy fatty compounds has recently been reported. The surface tension of some selected products was determined in 1N NaOH and compared to that of some known materials, such as ricinoleic acid. The surface properties of the novel monohydroxy fatty acids are comparable or better than those of the reference materials. The critical micelle concentrations of the novel monohydroxy acids are in the range 10−4–10−3 mol/L, depending on their structure. Furthermore, the monohydroxy acids were more effective when the hydroxy group was closer to the functional group at C1. Allylic dihydroxy acids also lowered the surface tension but less so than the monohydroxy compounds. Theerythro andthreo diastereomers of the allylic dihydroxy acids can be distinguished by surface tension, with thethreo diastereomers possessing better surfactant properties. Mixtures of the novel hydroxy fatty acids are also effective, thus obviating the need for complete purification of the products. Side products such as enones, which are formed during the allylic hydroxylations, also lower the surface tension. The products may be suitable for use in microemulsions or as additives in various commercial products.