373 



The lower boiling fraction and the residue were discarded. The second 

 Eraction, too toi° C. a1 r.o millimetres, gave the following results : 



Boiling poinl 766 mm.) ... ... ... ... 218 220 C. coir. 



Spe< ific gravity at 15 C. ... ... ... ... = 0-93 



Rotation a B ... ... ... ... ... ... 5-0° < 



Refractive index at 20 C. ... ... ... ... [-4816. 



Nitrosochloride, melted at ... ... ... ... 1 1 ;° C. 



Phenylurethane, melted at ... ... ... ... iu°C. 



Both the nitrosochloritle and the urcthane. were readilj formed and in good 

 quantity. These results indicate that the alcohol was terpineol and that the 

 larvo-rotatorj modification predominated to a small extent in the oil oi this s] nicies. 

 rhe portion boiling between 101-110° C. was again fractionated al to 

 millimetres, when 30 c.c. were obtained boiling between r.08 110° C. ["his 

 Eraction had a distinct odour of geraniol. The specific gravitv at 15° = 0-9,1 »; 



rotation a 1-5°; refractive index at 20° = 1-4841, and yielded a ■- ! amounl 



ol a urethane, melting at 112°. It is thus evident that a considerable amount of 

 terpineol was also present in this portion. That it also contained geraniol was 

 shown by the formation of citral on oxidation. 



That geraniol is a common constituent in the oil of E. Australiana is also 

 suggested from the frequent presence of citral in the natural oil, and we have 

 isolated this aldehyde in a pure condition from the oil of this species distilled from 

 material growing in the Burraga district of New South Wales. 



Terpineol was also prepared from the second and third hour oils of this 

 species, distilled from material growing at Nerrigundah, New South Wales. 500 c.c. 

 boiling above 190° C. were repeatedly fractionated at 10 millimetres pressure, 

 the following fractions being eventually obtained (temperatures uncorrected) :— 

 Boiling between 70 and 99° C, amount was 180 c.c. 

 99 ,, ioi° C, „ ,, 144 c.c. 

 „ 101 ., 104° C, „ „ 5 c.c. 

 ,, 105 „ i09°C, ,, „ 30 c.c. 

 „ no „ 115° C, ,, „ 40 c.c. 

 The fraction 99-101 ° C. at 10 millimetres had :— 



Specific gravity at 15° C = 0-9362. 



Rotation a D - 3-8° 



Refractive index at 20 C. = 1-4816. 



Nitrosochloride melted at ... ... ... ... 113 



Nitrolpiperidine „ ... ... ... ... 159-160° 



Phenylurethane ,, ... ... ... ... 112°. 



When shaken with 5 per cent, sulphuric acid a iM>od yield oi terpin hydrate 

 was eventually obtained. 



The fractions 101-104° and 105-109° gave results agreeing with those 

 of the first sample, and geraniol was readily detected in the higher-boilini' 

 fraction. 



The terpineol from the Nerrigundah nil was thus in agreement with that 

 from the Youri material, although showing a slightly less kevo-rotation. There 

 was, however, a difference of four years in the dates of distillation of the two 

 samples. This species is probably the best of all the Eucalypts from which to 

 distil an oil containing the maximum amount oi terpineol. 



