SURFACE-TENSION STUDIES ON NOVEL ALLYLIC MONOHYDROXY AND DIHYDROXY FATTY COMPOUNDS - A METHOD TO DISTINGUISH ERYTHRO THREO DIASTEREOMERS

The suitability of the selenium dioxide/tert.-butyl-hydroperoxide syst em for obtaining allylic mono- and dihydroxy fatty compounds has recen tly been reported. The surface tension of some selected products was d etermined in 1 N NaOH and compared to that of some known materials, su ch as ricinoleic acid. The surface properties of the novel monohydroxy fatty acids are comparable or better than those of the reference mate rials. The critical micelle concentrations of the novel monohydroxy ac ids are in the range 10(-4)-10(-3) mol/L, depending on their structure . Furthermore, the monohydroxy acids were more effective when the hydr oxy group was closer to the functional group at C1. Allylic dihydroxy acids also towered the surface tension but less so than the monohydrox y compounds. The erythro and three diastereomers of the allylic dihydr oxy acids can be distinguished by surface tension, with the three dias tereomers possessing better surfactant properties. Mixtures of the nov el 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 sur face tension. The products may be suitable for use in microemulsions o r as additives in various commercial products.