_Pinene._--The first fraction distilling below 160° C., and which
possessed an odor of turpentine, was tested for pinene by means of the
nitrochlorid reaction.[27] A deep blue coloration was obtained with
slight turbidity, indicating a possible trace of pinene.
_Cineol, or eucalyptol._--Tests were made in fractions 2, 3, 4, 5,
and 6 for cineol, which was easily recognized by its odor. For a
qualitative test the iodol reaction was used, crystals of cineol iodol
which melted at 111° to 112° C. forming in each fraction. Fractions
3, 4, and 5, which smelled strongly of cineol and which doubtless
contained the major portion of cineol in the oil, were assayed by
means of the phosphoric acid method, as directed in the United States
Pharmacopœia for 1900.[28] From these four fractions a total amount
of 22.5 per cent of cineol was obtained, calculated from the original
oil. This figure represents approximately the percentage of cineol in
the oil, although it is low rather than high, since fractions 2 and
6 both showed the presence of cineol by qualitative tests, but the
quantitative estimation in these fractions was impossible owing to the
preponderance of other constituents in the fractions.
A test for terpinene in fraction 6, by means of the terpinene
nitrosite reaction, produced a characteristic blue coloration, but the
crystalline nitrosite would not separate.
_Camphor._--A strong odor of camphor being distinguishable in fractions
7, 8, 9, 10, and in residue, a quantitative separation was made as
completely as possible by means of the “freezing-out” method. Between
186° and 190° C. some crystals of camphor began to form in the inner
tube of the condenser, and at 195° C. the condenser had to be kept
jacketed with steam to prevent clogging, so rapidly did the camphor
distill over. The fractions above 195° C. were practically solid. The
camphor which separated at ordinary temperature was filtered on a force
filter, and the liquid portion of the fractions subjected to freezing
successively until camphor no longer separated. It is apparent that the
separation of the camphor from these small fractions by freezing out is
rather inaccurate because of the losses in transferring and filtering.
From the above fractions, however, a quantity of camphor was obtained
corresponding to about 40 per cent of the original oil. This figure
is low, for the separation on a larger scale working with much larger
fractions would reduce to a considerable degree the loss of camphor
which is unavoidable in such small fractions.
The fractions distilling between 195° and 208° C. yielded crystals
when treated with bromin in a petroleum-ether solution of the oil.
The crystals melted at 130° C. Thujone tribromid melts at 122° C.
A trace of thujone is therefore probably present in the oil. It is
very possible, in view of the fact that the acetylization of the oil
disclosed some free alcohol, that the last fraction contained some
borneol, which boils at 212° C.