UTILISATION OF RESIDUES OF ESSENTIAL OIL. 221 
derivative meiting at 72—73°'C. The phenol is, therefore, 
australol. 
The filtrate was repeatedly frozen until no more crystals 
were obtained. It gave a purple colouration with ferric 
chloride in alcoholic solution, but on distillation at 10 mm. 
it boiled at 115-—116° C. and a careful examination of its 
chemical and physical characters showed it to be australol 
contaminated with a trace of a dextro-rotatory body. In 
the subsequent experiments dealing with germicidal values 
it is described as the ‘liquid phenol.’ The co-efficient 
shows in a striking manner the slight deviation from the 
pure solid australol in the lowering of the number due to 
the impurity. 
Aldehydes.—1000 c.c. of the crude oil, after removal of 
phenol, was shaken with 1000 c.c. 33% sodium bisulphite 
solution, and after 24 hours the emulsion was filtered with 
suction. The solid crystalline cake obtained was washed 
with ether-alcohol until free from oil and dried on a porous 
plate. It weighed 120 grams and on treatment with 
sodium carbonate solution and steam distillation 48 c.cs. 
of aldehyde were obtained possessing the following charac- 
ters:—Specific gravity t2° C. 0°9792, optical rotation — 7°6°, 
and refractive index, 20° C. 1°5271. On examination by 
the method described by one of us (A.R.P.)' it was found 
to consist approximately of 94% cuminic aldehyde with 67% 
phellandral. The aqueous bisulphite filtrate from the solid 
compound was separated from the oil and decomposed with 
sodium hydroxide solution when 180 c.c. crude cryptal was 
obtained. All three aldehydes were purified and gave 
similar constants to those described in the above mentioned 
paper, with the exception that the optical rotation of the 
cryptal was slightly lower, — 68°2’, 


1 Journal of the Chemical Society, London, Vol. 121, (1922) p. 266-269. 
