On again rectifying the 46 c.c. which distilled between 70 and 80 C., 

 15 c.c. were obtained boiling below 76 C. This portion consisted principally of 

 methyl and ethyl alcohols. The thermometer then rapidly rose to 78 C. ; 

 between 78 and 78-5 C. 15 c.c. distilled. This was found to consist mostly of 

 ethyl alcohol; it was readily oxidised to acetaldehyde and then to acetic acid; 

 it also formed ethyl acetate, and gave other chemical reactions for ethyl alcohol. 



To prove the presence of methyl alcohol, the portion distilling below 

 76 C. was carefully oxidised, the acids distilled off in the usual way, and their 

 barium salts prepared. The barium sulphate thus obtained was 95-18 per cent., 

 indicating 13-56 per cent, of barium formate, and 86-44 P er cen -t. barium acetate. 

 The presence of formic acid was proved by its characteristic reactions, and an 

 excellent silver mirror was obtained. Formic acid was also detected by M. Voiry 

 in the oil of E. globulns (Compt. Rend. 1888, 1419). See .also the article in this 

 work on the free acids of Eucalyptus 'oils. 



The liquid remaining in the flask, which had separated into two layers, 

 was then distilled, and the portion which came over below 99 C. removed. 

 On continuing the distillation, part of the "oily' layer came over with the 

 steam, and partly separated again in the receiver. It was added to the upper 

 portion still remaining in the flask. Valeraldehyde was shown to be present in 

 this oily layer, and it was removed by combining it with acid sodium sulphite, 

 and after separation oxidising it to valeric acid. The unacted-upon portion 

 formed esters in the ordinary way, amyl-acetate being readily detected. On 

 gentle oxidation the odour of butyric acid was obtained, but on energetic 

 oxidation the acids formed were acetic and valeric. Ethyl alcohol could hardly 

 have been present under the circumstances, so that the acetic acid shown to be 

 present was apparently obtained by the oxidation of one of the alcohols. This 

 points to the probable presence of iso-butyl alcohol existing as such in the original 

 oil. Valeric acid was readily detected by its characteristic objectionable odour, 

 when the salt was decomposed with sulphuric acid, and the formation of this 

 acid points to the prior presence of amyl alcohol. Iso-amyl alcohol is a frequent 

 constituent in Eucalyptus oils and is more pronounced in those intermediate 

 between the pinene oils and those richest in cineol. A determination of the 

 mixed barium salts of the oxidation product gave 86-8 per cent, barium sulphate, 

 indicating 79-81 per cent, barium acetate and 20-19 P er cen -t. barium valerate. 

 The results of this determination with the first distillate from Eucalyptus 

 phellandra indicated that methyl, ethyl, iso-butyl, and amyl alcohols were present. 

 Normal butyric acid has also been found in the oils of other species of Eucalyptus. 

 (See the article in this work on the Butyl ester of butyric acid.) Although the 

 presence of the above enumerated monohydric alcohols was thus demonstrated, 

 yet they were not in sufficient amount to account for the exceeding solubility 

 of the oil, a character evidently due to the influence of the higher boiling 

 alcohols. (See the article on the Terpineols of Eucalyptus oils.) 



