Y:LANG-YLANG OIL. 81 



sample of first quality oil in which the solid formed by saponification was filtered, 

 well washed Avith absolute ether and decomposed by dilute acids, the resulting 

 substances being benzoic, salicylic, formic and acetic acids as well as a very small 

 quantity of phenols. 



The contents of the first tliree flasks were completely saponified by two hours' 

 heating on the steam bath with a reflux condenser, the last fraction by one week's 

 standing at room temperature. The procedure used in working up the product 

 was like that given in the details of experiment 1. 



The solid, acid portion : The total amount was 91 grams. The benzoic and 

 salicylic acids were separated by means of their esters,, salicylic methyl-ester 

 being soluble in a 10 per cent sodium hydroxide solution. The methyl esters after 

 this separation, boiled almost constantly at 195° and 224°, respectively, so that 

 there would seem to be no reason to suspect any acids other than benzoic and 

 salicylic to be present in the solid, acid portion. Tlie total quantities were 6 

 grams of salicylic acid and 85 of benzoic. 



The soluble acid portion: The alkaline, aqueous solution was first evaporated 

 to a small bulk in order to remove all neutral volatile substances. It was then 

 rendered acid with dilute sulphuric acid, and the volatile acids were distilled. 

 The total volatile acids, calculated as acetic acid, were 63.5 grams. Barium 

 salts were prepared and gave the following analytical data : 



0.6995 gram barium salt gave 0.6521 gram barium sulphate 



^ , Calculated (per cent) for 



Found " ' 



(percent). Ba(C2H30o)2HoO Ba(HC0o)2 



Ba 54.97 48.70 60.3 



Naturally, the percentage of barium found gives no clue to the relative propor- 

 tions of the two acids present because of the differing solubilities of the salts, 

 the acetate of barium being more soluble in water than the formate. The solu- 

 tion of the soluble acids reduces potassium permanganate and also mercuric 

 chloride, and as neutral salts have been prepared from the solution with a 

 greater percentage content of barium than is in the acetate, the only conclusion 

 is that formic acid is present. 



The formic acid was estimated according to the method of H. C. Jones '- by 

 heating with an excess of standard potassium permanganate in the presence of an 

 alkaline carbonate, then adding a known excess of o.xalio acid, and titrating back 

 with potassium permanganate. The result showed that from the original kilo 

 of oil there were separated 41.2 grams of acetic and 17.1 grams of formic acid. 



A portion of the barium salts of these acids was treated with ethyl alcohol 

 and concentrated sulphuric acid; the resulting esters possessed the characteristic 

 odor of ethyl acetate and formate and no odor was noted suggesting the presence 

 of acids other than those named. Reyehler" states that he has observed a 

 pronounced, rancid odor in the aqueous mother liquors, suggesting small amounts 

 of the higher fatty acids. I could confirm his observation and I believe there is 

 a trace of valerianic acid in the mother liquor. 

 . The phenol fraction. — This was in all 10 grams. The phenols gave a green 

 color with ferric chloride and an odor resembling that of kreosol (the 3-methyl 

 ether of homopyrocatechin (OcH3(C'H3)'(OCH3)^(OH)') was noted in this fraction. 

 There was separated from tliis fraction according (o the method of Baumann- 

 Schottcn by the action of beiiznyl chloride a sumll Miiiount of /K((((-krcsol ben- 



"Am. Chrin. J. (1895). 17, 539. 

 " Loc. cit. 

 69330 3 



