215 



however, a large amount of aldehyde separated, which was 

 extracted with benzene, the latter being evaporated off. This 

 constitutes aldehyde C. The oil which was not absorbed by 

 the sodium bisulphite contains cineol, cymene, terpenes, and 

 sesquiterpenes, and was used for the separation of the 

 sesquiterpene. This separation of aldehydes was performed 

 on the last fractions of steam distillations A 3 and A 4, and 

 also on the final fractions of a steam distillation of 2 litres of 

 the crude oil. These latter are indicated by the letters 

 c and d in the table which follows (Table 1). The results 

 tabulated below are calculated for 100 ccs. of oil used. 



Table 1. 



Sample 



Aldehyde A 



Aldehyde B 



Aldehyde C 



Unabsorbed Oil 



No. 



Distl.JFr'ct. 



Rotat. 



Amt. 

 in 



CCS. 



Eotat. 



Amt. 

 in 



CCS. 



Eotat. 



Amt. 

 in Rotat. 



CC3. 



Amt. 

 in 



CCS. 



Rotat. 



a 

 b 

 c 

 d 



A3 



A 4 



P'n'lt 



final 



e 



d 



imate 



—26-15 

 —26-18 

 —24-68 

 —25-7 



14-2 —50-0 

 16-0 —53-6 

 13-3 -43-9 

 16-4 -54-9 



3-9 

 2-2 

 3-9 

 4-6 



-88-5 

 -86-8 

 -90-0 



66 

 7-8 

 4-8 

 3-6 



-79-3 

 —74-3 

 -74-1 



50-0 

 500 

 58-6 

 51-5 



-8-3 



—15-1 



—9.5 



As the yield of the separate aldehydes was so small when 

 w^orking o^n these fractions, a quantity of the higher boiling 

 fractions (called the residual oil) which remain in the still 

 after refining the oil on a commercial scale was obtained 

 from Kangaroo Island. This residual oil was obtained from 

 Eucalyptifs en eori folia only. 



The oil was steam distilled, and the distillate had a 

 rotation of -27*88°. Several separations as described above 

 were performed on tliis oil, and the results tabulated are 

 calculated for 100 ccs. used. 







Table 



2. 









No. 



Aldehyde A _ Aldehyde B 



Aldehyde C 



Unabsorbed Oil 



i 



Amount 

 in ccs. 



Rotation 



A^^"f Rotation 

 m ccs. 



e 

 f 



16-0 -20-65 

 U-7 —15-8 

 11-4 : -12-75 



2-2 i — 

 07 1 — 



1-9 ! -99-7 



1 

 1 



11-5 

 250 

 27-3 



-60-0 

 -62-7 

 —63 8 



38-2 

 35-0 

 32-4 



—4-15 

 -2-31 

 -2-55 



The semicarbozone prepared from aldehyde A (Experi- 

 ment g) melted constantly at 208° C. That prepared from 

 aldehyde B (Experiment g) melted constantly at 199° C. 



The various aldehyde portions separated were then 

 -examined individually. 



