— 47 — 



Another fraction of the citronella oil with a density of 0,8330 (at 15°) 

 and opt. rot. — 29°59', when hydrated according to Enklaar's method and 

 saponified, yielded considerable first runnings and an alcohol possessing 

 the following characters: b. p. 78 to 80° (5 mm.), d 15 0,9180, « D — 9°44': 

 Faint terpineol-like odour. The phenylurethane, at first oily, finally turned 

 solid (m. p. 110 to 111°). Hence the alcohol was impure «-terpineol, 

 owing its generation probably to the dipentene or limonene which was 

 admixed to the fraction. Further particulars concerning the new terpene 

 must be reserved until after subsequent examination. 



The fractions with higher boiling points than the terpene fraction 

 consisted chiefly of citronellal, but they contained, besides considerable 

 proportions of borneol, certain other compounds with somewhat charac- 

 teristic odours, including a body with a peculiar linalool-like aroma, but 

 which was not identical with linalool. We have not yet succeeded in 

 identifying this body from its derivatives. It was discovered in the portions 

 boiling between 81 and 85°, sp. gr. 0,9122, after they had been freed from 

 citronellal with bisulphite, and from borneol by freezing. No phenyl- 

 urethane was formed, but oxidation with bichromate and sulphuric acid 

 gave rise to citral, b. p. 89 to 91° (3 to 4 mm.). The characteristic citral- 

 idene cyanoacetate had m. p. 120 to 121°. Another fraction, b. p. 71 to 75° 

 (d 15 o 0,8982) when acetylated, afforded an oil, b. p. 72 to 74° (4 mm.), with 

 an odour of linalyl acetate, but, again, the saponified product yielded no 

 phenylurethane, although it was oxidisable into citral. From the above 

 it may however be concluded (contrary to our previous experience) 1 ) that 

 linalool is not a constituent of citronella oil. We hope to be in a position, 

 later on, to make further communications on this subject. The chromic 

 acid oxidation-product mentioned above, which did not react with bisul- 

 phite, was found to contain an oil with a thujone-like odour, which 

 reacted in part with semicarbazide. Possibly the semicarbazone recrys- 

 tallised from methyl alcohol, m. p. 179 to 182°, was a derivative of thujone. 

 We also attempted, by oxidising with permanganate, to prepare from a 

 fraction boiling between 202 and 210° (d i5 o 0,9121), with a faint odour of 

 thujyl alcohol, the thuja keto acid, m. p. 76°, but were unsuccessful. 



The high Z-borneol content of the succeeding fractions greatly militated 

 against their being tested for other alcohols. Unfortunately our endeavours 

 to eliminate this troublesome product by chemical means, e. g. chloral 

 remained without the desired result. The Z-borneol, m. p. 200 to 203°, 

 fchich was obtained by freezing-out was found, when oximated, to be free 

 from camphor. 



In a fraction boiling between 218 and 230°, which had been freed 

 from borneol as far as possible, we ascertained the presence of nerol, 

 albeit in inconsiderable proportions. This body was accumulated in an 



*) Report October 1899, 16. 



