— i6 — 
detection to the reaction products which portions of oil yield boiling 
between 215° and 220°. It is well known that the oil contains con- 
siderable quantities of camphor and safrol, i. e. two bodies whose boiling 
points lie so close to that of terpineol, that it is not possible to bring 
about a separation of this alcohol in a state which is at least to some 
extent pure, even if the fractional distillation is repeated over and over 
again. We have now succeeded in isolating terpineol from oil of 
camphor in the pure state, and that as a solid product, by removing 
in the first place the camphor as much as possible from the mixture 
of the three bodies. For this purpose, 600 grams of a camphor oil 
fraction whose boiling point was below that of safrol, were fractioned 
twice to three times in vacuo, and the portions boiling between 98° 
and 103° (10 mm pressure) thus obtained treated in alcoholic solution 
with hydroxylamine. After driving off the alcohol, the oil which had 
not reacted was separated by means of steam from the camphor 
oxime which had been formed. By repeated rectification of the oil 
at atmospheric pressure we obtained fractions boiling at 216° to 218°, 
218° to 219°, and 219° to 221°, of which particularly the last two, 
when kept in a freezing mixture, formed viscid oils, and congealed in 
crystal -form when inoculated with a terpineol crystal. The crystals, 
recrystallised from dilute alcohol, melted at 34° to 35°. The physical 
constants were as follows: d^50 =0,9391; 0^21° = — 2^45' (20 mm); 
boiling point 99^ to 100° (9 to 10 mm pressure). The isolated 
terpineol was therefore 1-terpineol of the melting point 35°. The 
mother liquors of the crystallised body served for the production of the 
phenyl urethane of the melting point 112°, and also of the nitroso-chloride. 
The piperidine derivative of the latter melted at 158° to 159°. 
The final proof of the presence of terpineol in camphor oil having 
now been supplied, we have taken pains to demonstrate once more 
the presence of camphene^). In 1894 this terpene had already been 
detected in our laboratory in oil of camphor 2), but, as the presence 
of large quantities of pinene renders the detection of camphene diffi- 
cult, the result obtained by us was not quite free from objection. A 
separation of these two hydrocarbons by fractional distillation is not 
possible, but this time, when working up the first runnings of a very 
large quantity of camphor oil, we were able by long-continued frac- 
tional distillation to separate two principal portions, of which the one 
consisted chiefly of pinene, whilst the other contained large quantities 
of camphene. 
The portion boiling between 155° and 157° was chiefly pinene; 
ap -[" 35'^ ^15° — o>S65. The nitroso chloride obtained from it, 
^) This examination was made in our laboratory by Mr. Zadig, of Malmo. 
2) Report April 1894, 69; Journ. f. prakt. Chemie II. 49 (1894), 19. 
