Abstract
Thianaphthene, naphthalene, and their methyl homologues were identified from the cut 2 (boiling range 215 -250°) of the NTU Colorado shale oil. First, cut 2 was finely fedistilled into narrow subfractions of A, B, and C. After aliphatic hydrocarbons in the fraction A were removed by means of silica gel column chromatography, the concentrated thianaphthene and naphthalene mixture was separated by alumina column chromatography. It was found that naphthalene was adsorbed on alumina slightly more weakly than thianaphthene. Each of thianaphthene and naphthalene enriched fractions was purified by preparative gas chromatography, and these two compounds were identified with the authentic specimen by nuclear magnetic resonance, ultraviolet, and infrared spectra. Similarly, 6-methylthianaphthene, 1- and 2-methylnaphthene, and diphenyl were isolated from the fraction B and identified. Further, 2, 6- and 1, 6-dimethylnaphthalenes were identified in the fraction C.
