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Surface tension studies on novel allylic mono‐and dihydroxy fatty compounds. A method to distinguish erythro/threo diastereomers
Author(s) -
Knothe G.,
Dunn R. O.,
Bagby M. O.
Publication year - 1995
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02635777
Subject(s) - allylic rearrangement , diastereomer , chemistry , ricinoleic acid , surface tension , pulmonary surfactant , organic chemistry , critical micelle concentration , micelle , fatty acid , aqueous solution , catalysis , biochemistry , physics , quantum mechanics , castor oil
The 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. The erythro and threo diastereomers of the allylic dihydroxy acids can be distinguished by surface tension, with the threo 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.