— 72 — 
8 mm pressure at 88 to 93°. When distilled at ordinary pressure, the 
following fractions could be distinguished: 
I. First runnings — 205°, 2. 205 — 217°, 3. 217 — 221°, 
4. 221 — 224°. 
Of these fractions, the third solidified in the cold, the second and 
fourth only when a crystal of terpineol was introduced. The constants of 
the oil boiling at 217 to 221^ were as follows: specific gravity 0,9286; 
optical rotation -[-30^56'. The melting point of the solid terpineol 
was found at 34°. With phenyl isocyanate it formed a phenyl me- 
thane of the melting point 110°, which, after recrystallisation from 
alcohol, melted at 112°. 
The presence of free d-terpineol of the melting .point 35° in 
petitgrain oil has therefore been demonstrated. 
Fractions which came under consideration for the boiling point of 
citronellol, were heated for a prolonged time with concentrated formic 
acid, for the purpose of removing the other alcohols contained in them, 
such as geraniol, linalol, and terpineol. The reaction - product thus 
obtained was a thick oil, which commenced to boil at 195°, at 8 mm 
pressure, and which therefore only consisted of products of polymeri- 
sation of the above mentioned alcohols. 
Primary alcohols could not be isolated either by treating some of 
the fractions (especially the one boiling between 83 and 98° at 8 mm 
pressure) with phthalic anhydride. 
As Passy^) had already observed, geraniol and its acetic acid 
ester represent a not unimportant constituent of petitgrain oil. As, 
however, no proofs had yet been produced in support of this state- 
ment, we wish to add here briefly the results of our examination 
concerning these two bodies. 
When distilling the portions boiling above 90°, at 8 mm pressure, 
we arrived at fractions which, according to their odour, ought to 
consist of fairly pure geranyl acetate. A faint but yet clearly dis- 
cernible blue fluorescence, which was characteristic of all fractions 
passing over between 100 and 114° at reduced pressure, might per- 
haps be caused by an infinitesimal admixture of anthranilic acid ester. 
By sufficiently repeated fractionating in vacuo we succeeded in obtaining 
a fraction very rich in ester, whose constants are exceptionally close 
to those of pure geranyl acetate. The physical properties were as 
follows: Specific gravity 0,9178, optical rotation -|-i°6', saponifi- 
cation number 266,8, the latter corresponding to a content of 93,4 
per cent of geranyl acetate. The acid obtained by saponification of 
this fraction was converted into the silver salt, which, after recrystallis- 
^) Bull. Soc. chim. III. 17 (1897), 519. 
