Abstract
By sequences involving fractional distillation, thiourea adduction, gas chromatography and crystallization of solid derivatives, there have been isolated from the naphthenic acids of a California petroleum four acyclic acids of isoprenoid structure: 2,6,10-trimethylhendecanoic acid, 3,7,11-trimethyldodecanoic acid, 2,6,10,14-tetramethylpentadecanoic acid, 3,7,11,15-tetramethylhexadecanoic acid. Structures were deduced by interpretation of spectra and confirmed by comparison with samples of the synthetic acids. Starting material for synthesis of the C 14 acid was farnesol, while phytol was starting material for synthesis of the C 19 and C 20 acids. No optical rotation could be observed for the acids isolated from petroleum. In mass spectrometry of amides of these acids, in addition to the set of fragments containing the amido grouping, there was also observed a complete set of irons containing the nitrile grouping.
Published Version
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