The Nitrogen Bases In Tasmanite Shale Oil

Although these 'tal' bases' are mainly derivatives of pyridine and/or quinoline, other compounds of a pyrrole nature have been reported to occur, for instance Petrie (1905) recorded the presence of pyrrole compounds in the oil obtained from the torbanites of New South "Vales, and aecounts of the shale oil from Colorado giving the same reaction have been reported by McKee (1£125). The first systematic work on the nitrogen compounds in shale oil was that of VVilliams (1854) on Dorsetshire shale. Williams wrote that they burnt with a sl'noky fian1P, possessed a very bad smell, were soluble in alcohol and gave a blue precipitate with cupric nitrate. He isolated pyridine and some of its lower homo!ogues. Garret and Smythe (1902) working on Scottish shale oil succeeded in isolating and identifying seven members of the pyridine series by oxidation to the corresponding acids with potassium permanganate and by the preparation of the aurichlorides of the bases. Robinson (187£1) recorded the presence of nitrogen compounds in Scottish shale oil bases, occurring in the fractions boiling between 270" C. and 8£10" C .. Hp proved that they were dicyclic compounds of the iso-quinoline series. In reference to the :formation of salts, Robinson writes 'attempts were made to get c.ry~ta!line salts from t.he mixed bases; the double chlorides of platinum, gold, cadmium, mercury, lead and zinc were tried but without sucees~, only resinous sticky maSEes being obtained. The same failure in getting cr~'stalline salts was experienced when the bases were tn~ated with sulphuric, hydrochloric, nitric and oxalic acids '. Kogerman (I0:;1) gives a detailed description of the methods used to obtain the purified bases from Estonian shale oil, and makes the statement that 'ThE' pure bases, separated from the shale oil, formed a reddish liquid with a quinolinelike odour, specific gl'avity--O·97~n at 15 0 and n" -1·589/19° '. He also states that