1 6 Henry G. Smith t 



(a) 1.5144 grams of this esterised oil, when boiled withi 

 alcoholic potash, required 0.056 gram KOH. S.N.= 

 36.9. 



(b) 1.5162 grams, when treated with alcoholic potash in the- 

 cold, with two hours' contact, required, 0.042 gram. 

 KOH. S.N. = 27.7. 



To confirm this result some cold saponified oil was steam dis- 

 tilled. Besides the terpenes an aromatic alcohol came over, which 

 ■was strongly indicative o^f geraniol. 



• Although the chief alcohol may be considered to be geraniol, yet 

 it is evident that other alcohols were also present. 



Determination of Combined Acids. 



A portion of the crude oil w^as boiled for two hours with an 

 aqueous solution of sodium hydroxide. The alkaline solution was 

 separated and acidified with sulphuric acid. The clear filtered 

 solution was distilled until volatile acids ceased to come over. The 

 distillate was neutralised wuth Barium hydrate solution, evapo- 

 rated to dryness and treated in the ordinary way. 



(a) 0.1868 gram Barium salt gave 0.1580 gram BaSO^ = 

 84.58 per cent. 



(b) 0.2306 gram Barium salt gave 0.1958 gram BaS04 = 

 84.91 per cent. 



On treating the Barium salt with sulphuric acid the odour of 

 butyric acid was noticeable; it is thus assumed that butyric acid 

 was also present. The results obtained arei equal to 59.8 per cent, 

 of Barium acetate, and 40.2 per cent. Barium butyrate. The 

 acetic acid was evidently in combination with the geraniol as 

 geranyl-acetate. 



The amount of free acid in the crude oil could not be satisfac- 

 torily determined for several reasons, and although a small 

 amount of a solid acid was eventually isolated, yet the saponifica- 

 tion number was under 2. 



Phenol and Free Solid Acid. 



A portion of the oil was shaken with dilute sodium hydroxide- 

 until extraction was complete. The aqueous solution was separated, 

 shaken with ether to remove adhering oil, acidified, and again 

 shaken with ether. The ether extract thus obtained was equal to 

 0.198 per cent., and was semi-crystalline, due to the presence of the 

 solid acid. 



