The Monohydric Alcohols of the Cnlrhn + 1 OH 

 Scries occurring in Eucalyptus Oils. 



THE abnormal solubility in alcohol shown by the oils of some species in which 

 cineol is not pronounced, and phellandrene present in some quantity, points to 

 the occurrence of an excess of alcoholic bodies not present in the more distinctly 

 phellandrene-bearing oils of other Eucalypts. The comparatively high percentage 

 of cineol in the oil of E. phcllandra over those of E. dives, E. radiata and similar 

 species, naturally assists this solubility, but that constituent is not present in 

 sufficient amount to alone place the oil in the same class, as regards solubility, 

 with those richest in cineol. The odour possessed by the oil of E. phellandra 

 is somewhat aromatic, largely due to the presence of terpineol, and is perhaps 

 characteristic of that species. 



It was this peculiarity of solubility that induced us to carry out investiga- 

 tions in order to determine whether the earlier members of the monohydric 

 alcohols were also present. The lower boiling aldehydes only occur in this 

 oil in very small amount, and the peppermint ketone, piperitone, is not pro- 

 nounced, so that those constituents cannot influence the solubility to any 

 great extent. Both ethyl and amyl alcohols had previously been determined 

 in a Eucalyptus oil (stated to be that of E. globulns] by Bouchardat and Olivier, 

 and if no doubt exist as to the origin of the material worked upon by them, then 

 these alcohols are more frequently present in the oils of the various species than 

 has been supposed. Unfortunately, the products of the several species have not 

 always been kept distinct. In the oil we obtained from E. cinerea, alcohols boiling 

 below 100 C. did not appear to be present, and that species yields an oil 

 belonging to the same group as that distilled from E. globulus. 



Through the kindness of the Australian Eucalyptus Oil Company we were 

 supplied with two litres of the water which first distilled on rectifying the 

 oil of E. phcllandra by direct distillation. The free acetic acid was first 

 neutralised, and the water distilled, a Glynsky's fractionating column being used 

 for the purpose. 



The first distillation gave 88 cubic centimetres boiling between 70 and 

 90 C., and 30 c.c. between go and 95 C. On again fractionating the portion 

 distilling between 70 and 90 C., 15 c.c. came over between 70 and 76 C. ; 

 between 76 and 78 C. only a. very small amount was obtained; but between 

 78 and 79 C. no less than 26 c.c. distilled, and 5 c.c. more below 80 C. Although 

 containing a small amount of aldehyde, yet the greater portion of the fractions 

 was found to be alcohols. As the lower boiling alcohols distilled off, the liquid 

 remaining in the flask separated into two layers," the upper one having an oily 

 appearance. The 30 c.c. obtained in the first distillation, boiling between 90 and 

 0,5 C., were then added, when the oily layer again dissolved; on again removing 

 the lower boiling alcohols the oily substance again separated. The upper layer, 

 which consisted principally of the higher homologues, was investigated separately. 



