338 Messrs. M. M. Pattison Muir and S. Sugiura on 



without being treated with sodium. The greater portion 

 came over below 210°. After repeated fractionation and 

 removal of the solid matter which separated out on standing, 

 the main portion of this liquid boiled between 198° and 203°. 



After each fractionation^ however, a considerable quantity 

 of resinous matter remained in the flask ; and it was only 

 when this had been repeatedly removed that it was found pos- 

 sible to distil the liquid entirely below 203°. It would thus 

 appear that the liquid contained compounds which became 

 polymerized by the action of heat alone ; in this respect it 

 agrees with the behaviour noticed in the case of many other 

 essential oils. After repeated distillation over sodium, the 

 fraction which, on the second distillation, boiled below 190°, 

 was split up, for the most part, into two portions : — a smaller, 

 boiling from 156° to 158°; and a larger, boiling from 166° to 

 168°. During the fractionation a very considerable quantity 

 of yellowish-red resin was formed, chiefly, it seemed, by the 

 action of the sodium upon the oil. This resin was decom- 

 posed by agitation with water ; the oil obtained was separated, 

 dried, and again fractionated. From the fractions of higher 

 boiling-points a large portion of the solid matter already 

 noticed separated on standing at the ordinary temperature. 



In the first distillation of the oil, boiling was discontinued 

 upon the temperature reaching 215°; that which remained 

 was a thick, very dark-coloured liquid. This liquid was now 

 submitted to distillation ; about one half distilled below 250°, 

 leaving a semisolid, nearly black mass in the retort. On 

 fractionating the distillate, solid matter was deposited from 

 those fractions which boiled below 220°, but not from the 

 higher fractions. After the removal of all matter volatile 

 below 240° a dark-brown liquid, with distinct green fluores- 

 cence, remained in the flask. This liquid v/as subjected to 

 distillation in a current of superheated steam. About one 

 eighth of the total liquid was obtained in the distillate, the 

 remainder having become almost solid. The distillate, after 

 drying and fractionation, was found to consist almost com- 

 pletely of the solid matter already referred to, held in solution 

 by hydrocarbons. 



The oil was thus separated into four main portions : — 



(1) A liquid boiling at 156° to 158°' 



(2) A liquid boihng at 166° to 168°. 



(3) A liquid boiling at 198° to 203°. 



(4) A solid deposited chiefly from those fi'actions 

 of the oil boihng from 190° to 220°. 



The resinous matter which remained after the final distil- 



