173 



The resorcinol determinations for the cineol were always taken with the 

 fractionated oil in the portion distilling below 190 C., and calculated for the 

 crude oil. The results would be altogether too high if taken with the commercial 

 sample directly, because terpineol and other bodies are also absorbed; even in 

 the portion distilling below 190 C., substances other than cineol are absorbed 

 by the resorcinol, and the results are consequently too high when determined in 

 this way. 



The specific gravities were in all cases corrected for 15 C., the factor 

 0-00075 being employed for that purpose. 



" Second Hour Oil." A sample of the " second hour oil " was 

 forwarded to us by Mr. C. Gough, ot Yourie, and was portion of the " second 

 hour oil " he had commercially distilled. It was but little coloured, and had 

 quite an aromatic odour. It had specific gravity at 15 C. = 0-9291 ; rotation a D 

 + 2.2 ; refractive index at 20 = 1-4720 ; and was soluble in i-i volumes 70 per 

 cent, alcohol. On distillation, 64 per cent, came over between 172 and 193 (corr.). 

 This fraction had specific gravity at 15 = 0-9131 ; -rotation a D + 3-3 ; refractive 

 index at 20 = 1-4655, and contained 31 per cent, cineol by the phosphoric acid 

 method, representing 20 per cent, in the "second hour oil." 25 per cent, came 

 over as the second fraction, boiling between 193 and 227. This had a specific 

 gravity at 15 = 0-9283; rotation D 0-2; and refractive index at 20 = 1-4760. 



The saponification number for the esters in the " second hour oil " was 

 11-4, while in the acetylated oil it was 95-1. This latter figure represents 33 per 

 cent, of ester if calculated for a C IO H I7 OH alcohol, and if considered to consist 

 wholly of terpineol, there was 23 per cent, of that substance, at least, in the 

 free condition in the " second hour oil." 



" Third Hour Oil." A sample was also forwarded by Mr. Gough. It 

 showed but slight chemical differences from the oil of the second hour, except that 

 the alcohol was a little more pronounced. It had specific gravity at 15 C. = 0-9266 ; 

 rotation D + 2-6; refractive index at 20 1-4747, and was soluble in i-i 

 volumes 70 per cent, alcohol. Addition of more alcohol determined the presence 

 of paraffin in both the second and third hour oils. The saponification number 

 for the ester plus that of the free acid was 9-7 ; while with the acetylated oil 

 it was 116-03; representing 29-4 per cent, of free terpineol in the '' third 

 hour oil." 



On distillation, 55 per cent, came over below 193 C., and 35 per cent, 

 between 193 and 225. 26 per cent, ot cineol was found to be present in the first 

 fraction, determined by the phosphoric acid method. The specific gravity of the 

 first fraction at 15 C. : : 0-9145 ; and refractive index at 20 1-4669. The 

 second fraction had specific gravity at 15 = 0-9267; rotation 1-4; refractive 

 index at 20 = i'477O. The saponification number for the ester plus that of the 

 free acid was 9-4. A portion of the second fraction of the "third hour oil" was 

 acetylated, when the saponification number had increased to 124-5. This 

 represents an ester percentage oi 43-6, indicating 31-7 per cent, of free terpineol 

 at least in this portion. (For the determination of the Terpireol, see the article 

 on that substance in this work.) 



In February, 1930, through the kindness of Mr. R. H. McNeice, we 

 received material pf this species for distillation, from Black Springs, a locality 



