

The Monohydric Alcohols of the CnH2n.f1 OH 

 Series occurring in Eucalyptus Oils. 



Tin abnormal solubility in alcohol shown by the oils oi some species in which 

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

 the occurreno ol an excess oi alcoholic bodies no1 present in the more distinctly 

 phellandrene I ■ iils oi other Eucalypts. The comparatively high percentage 



ol cineol in the oil oi E. phellandra over those oi 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 oi E. phellandra 

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

 characteristic of thai species. 



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

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

 alcohols were also present. Tin- 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 amy! alcohols had previously been determined 

 in a Eucalyptus oil stated to he that of E. globulus by Bouchardat and Olivier, 

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

 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 kepi distinct. In the oil we obtained from E. cinerea, alcohols boiling 

 below ioo° C. did not appear to be present; and that species yields an oil 

 belonging to the sum -roup as thai distilled from /:'. globulus. 



[Through the kindness oi the Australian Eucalyptus nil Company we were 



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



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



tralised, and the watei distilled, a Glynsky's fractionating column being used 



for tin- purpose. 



The lirst distillation gave 88 cubic centimetres boiling between 70 and 



90 ('., and 30 cc. between 1,0 and 95 C. (hi again fractionating the portion 



distilling between 70 and 90 C, 15 cc came over between 70 and 76' ( , 



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



id 79 C. no less than 26 cc. distilled, and 5 cc. more below So C. Although 



lining a small amount oi aldehyde, yet the greater portion oi the fractions 



a fou d i" be alcohols. As the lower boiling alcohols di tilled off, the liquid 



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



appe: 1 1 The 30 1 1 obtained in the first distillation, boiling 1 etwei n 91 



95° C, were then added, when the oily I. lin dissolved; on again removing 



the lower boiling alcohols th< oilj substance again separated. The upper la 

 whh h . ousted J ,)•;,,, ipally of the higher homologues, was investigated 1 parately, 



