Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Abstract Only
Publication Acceptance Date: 5/1/1996
Publication Date: N/A
Technical Abstract: Fatty compounds with isolated double bonds react with the selenium dioxide / tert.-butylhydroperoxide system to afford two allylic monohydroxy compounds and erythro / threo diastereomers of allylic dihydroxy compounds. Especially some allylic monohydroxy compounds are very effective surfactants and compare favorably with naturally occurring materials such as ricinoleic acid. For example, 8-hydroxy-6(E)-octadecenoic acid lowers the surface tension of a 1N NaOH solution to 32.9 mN/m at a critical micelle concentration of 5x10-5 mol/L while ricinoleic acid lowers the surface tension to 33.5 mN/m at 5x10-4 mol/L. The mathematical evaluation of the NMR spectra of the allylic monohydroxy compounds can present a method to analyze mixtures of fatty compounds.