80 



BACON. 



of CH3OH to form the metlij'l esters witli the 9.0 grams of solid acids which were 



found. 



Tlie neutral portion of the saponification product distilled in vacuo gave the 



following fractions: '^ 



30° 30° 



Number 1: 37 grams; B. P. 00° to 120° at 37 mm., a'-j^= — 16.5: N — 



= 1.478. 



Number 2: 15.5 grams; B. P. 120° to 130° at 34 mm.; A^=— 31.2°; 



N^ = 1.4797. 



30° ,_„„ 

 Number 3: 17.5 grams; B. P. 130° to 150° at 30 mm.; A -_q=— 7'-/ ; 



"10° 

 n2^ = 1.4943. 



Number 4 : 0.5 grams of resinous residue. 



Treatment of fraction 1 with dilute, aqueous potassium permanganate gives 

 benzoic acid melting at 122°, thus proving the presence of benzyl alcohol in this 

 fraction. 



The aljove results gave the composition of ylang-ylang oil as follows : 



Component. Per cent. 



Neutral 81.50 



Formic and acetic acids 5.54 



Benzoic acid 9.00 



Salicylic acid 0.60 



Methyl alcohol 2.02 



Total 



99.50 



Several attempts were made to isolate an aldehyde from ylang-ylang 

 oil, as treatment of the oil with fuchsine and sulphur dioxide gave the 

 color change characteristic of aldehydes, but phenylhydrazine shows no 

 trace of reaction with the oil and on shaking thoroughly with freslrly 

 prepared and very active sodiimi bisulpliite no such bodies could be 

 isolated by the usual means; so that no more than a trace of aldehydes 

 can be present in ylang-ylang oil. The work with 100 cubic centimeters 

 was repeated with 1,000 grams of ylang-ylang oil in the hope that the 

 decomposition of larger quantities would lead to the discover}^ of con- 

 stituents heretofore not recognized. 



Experiment 2. — One thousand grams of good quality ylang-ylang oil from 



Nueva Caceres and having the following constants: 



80° 

 Specific gravity, —-=0.912; 



.30° 

 A^ = -45.6° 



N^ = 1.4920; 



ester number. 100. were used. 



The oil was saponified in four lots, the first three by using 200 cubic centi- 

 meters of oil and 35 grams of potassium hydroxide dissolved in 150 cubic centi- 

 meters of 92 per cent alcohol the final one of 497 cubic centimeters of oil was 

 hydrolyzed with 60 grams of potassium hydroxide dissolved in 400 cubic centi- 

 meters of the same solvent. A'N'ithin a few minutes after the alcoholic potash was 

 added the oil became filled with crystals of the potassium salts of the acids. 

 No other solids separate. This was proved by a special experiment with a 



