— 48 — 



alcohol mixture which had been separated from the solution of the phthalic 

 ester salt by repeated treatment with calcium chloride, and after being 

 again purified by means of phthalic anhydride it was obtained after saponi- 

 fication in the form of an oil, b. p. 98 to 101° (6 to 7 mm.) to which a 

 faint borneol odour still adhered. It was positively identified as nerol 

 from the tetrabromide, m. p. 116 to 118°. The neryldiphenylurethane was 

 not obtained in an entirely pure form; it only melted between 55 and 57°. 

 The oil which contained nerol also contained a compound from which 

 water was given off when distilled under atmospheric pressure. It would 

 seem, however, that citronellol, which should have been present in these 

 fractions, did in fact not occur therein. In lieu of the silver salt of 

 the acid phthalate (m. p. about 126°) which is characteristic of citro- 

 nellol, repeated examination only afforded in every case the geraniol- 

 derivative melting at 133°. Hence, in corroboration of the results previ- 

 ously obtained by us 1 ), it may now be held to be tolerably certain that 

 Ceylon citronella oil contains no free citronellol. But on the other hand 

 we ascertained that citronellol is actually present in the oil in the form 

 of ^-citronellol, as esters (for instance, acetic ester), and certainly also as 

 butyric ester, in such proportions, indeed, that it can scarcely be over- 

 looked if the oil is carefully tested. The alcohol was isolated by treating 

 the saponified oil-portions boiling between 86 and 88° and between 88 

 and 94° (3 to 4 mm.) and sp. gr. 0,8805 to 0,8884 with phthalic anhydride 

 in benzene solution after previous elimination of the geraniol by calcium 

 chloride. The alcohol, which contained small proportions of borneol, 

 showed the following constants: b. p. 84° (3 mm.), di 5 o 0,8725, a D + 0°i3'; 

 b. p. 84 to 85° (3 mm.), di 5 o 0,8696, « D +I°17'. Another sample, which 

 had been further purified from primarily produced formiate possessed the 

 following properties: d 15 o 0,8661, « D + l°52 f , n D20O 1,45891, b. p. 92 to 93° 

 (5 mm.). The silver salt of the phthalate possessed the required m. p. of 

 125 to 126°. 



The present examination has also failed to supply any indications 

 of the presence of terpineol in citronella oil. When tested for geranyl 

 acetate it was found that it was possible to accumulate the oil only to 

 a very slight extent by fractionation in vacuo into those portions of which 

 the b. p. would indicate the presence of geranyl acetate (sap. v. 64 to 76), 

 because mixtures of borneol, nerol, geraniol, esters, a hydrocarbon, and 

 others, were present. But in any case, the odour of an acetic ester fraction, 

 b. p. 96 to 98° (4 to 5 mm.), sap. v. 85, together with the fact that th< 

 geraniol content was undoubtedly increased after saponification, warranted 

 the conclusion that geranyl acetate was also present in the fraction under 

 examination. 



x ) Report October 1899, 20. 



