Characterization of the nonvolatile compounds formed during the thermal oxidation of triolein

Triolein was subjected to thermal oxidation at 200 C for 24 hr with an air flow of 0.15 ml/min/gm. The oxidized material was saponified and converted to its corresponding methyl ester. Nonoxidized materials were separated from nonvolatile oxidation products using preparative thin layer chromatography. Further separation of these fractions was achieved using gas chromatography, gel filtration chromatography and solvent‐solvent extraction. Several compounds were isolated in this manner and their structures determined with the aid of nuclear magnetic resonance and mass spectrometry, as well as by supplementary chemical methods and by comparison with known compounds. These compounds were: (1) 2‐cyclohexyldodec‐5‐enoic acid and isomers; (2) a mixture of 2‐, 8‐, 9‐, and 10‐monohydroxystearic acid; (3) 9,10‐dihydroxystearic acid; (4) 1‐decyl‐2‐(dec‐6‐enyl)‐cyclohexane; (5) a mixture of isomers corresponding to a cyclic monomer of oleic acid containing both exocyclic and endocyclic unsaturation.