PHILIPPINE TERPENES AND ESSENTIAL OILS, III. 123 



The distillation residue is a hard, rellow, lustrous resin, soluble to the 

 extent of about 75 per cent in alcohol or turpentine, the solutions giving 

 liard, lustrous varnish coatings. This resin dissolves completely in two 

 Tolunies of linseed oil and two of turpentine, giving a varnish which 

 ■dries slowly (five days) to a tough, hard coating. The resin was further 

 tested as to its solubility in the following solvents : petroleum ether hot 

 or cold, very slight; cold acetone 75 per cent soluble, no more soluble 

 ■on heating; almost completely soluble in cold xylol, chlorofomi, carbon 

 tetrachloride and amyl acetate; in benzol it is but slightly soluble, hot 

 ■or cold ; it is 75 per cent soluble in ethyl acetate and 50 per cent soluble 

 in cold chloral hydrate, the latter solvent taking it up with a red color. It 

 is completely soluble on warming, the color being darker, approaching 

 hlue. 



( 3 ) Five hundred and seventy grams halao resin ■were carefully lieated in a 

 large evaporating dish over a free flame, the temperature being noted by means of 

 a thermometer thrust into the resin. At 100° there was much foaming, due to 

 ■\vater separation. Tlie mass was kept at 100° for one liour, then gradually raised 

 from 110° to 120°. Water continued to be given off and there was a very marked 

 thickening of the mass, but no especial evidence of decomposition. In the next 

 half hour, during which time the temperature had risen to 180°, the mass 

 gradually became thicker and more solid, with constant evolution of water. At 

 this stage 75 grams had been lost, and the acid number was 20.0 as compared to 

 18. G for the original resins. The corresponding saponification numbers were 

 25.4 and 23.0. All these differences may readily be credited to the loss of water 

 and show that this heating has no effect on thes6 two factors. The solubility 

 in alcohol seems to be somewhat increased over that of the unheated resin, but 

 this may be due to the water loss. The temperature was finally raised and 

 maintained at 200° to 220° for one hour. The resin melted and on cooling 

 solidified to a hard, brittle, lustrous mass. The loss finally was 240 grams or 42 

 per cent. 



(4) Three hundred grams halao, 700 cubic centimeters alcohol, and 50 grams 

 potassium hydrate were heated to 100° for one hour with a reflux condenser. 

 Almost complete solution had taken place upon saponification. The mass was 

 poured into water and separated into neutral and acid portions. Fifty-two grams 

 of solid, crystalline acids were separated from the alkaline extract on treating 

 with hydrochloric acid. These acids were only partly soluble in ether, and this 

 solvent therefore gives a means of separation. The neutral oils were shaken out 

 witli ether. At first all were soluble, but after the ether solution had stood for 

 two days, 60 grams of a cr3'stalline solid separated; this was filtered. The ether 

 was then dried and evaporated, whereupon the residual oil distilled in vacuo gave 

 75 grams of sesquiterpene, boiling between 130° and 134° at 15 millimeters, nearly 



all passing over at 130°; specific gravitv. ^'^° =0.9111 ; N§5! 1.4969; a5?°= 



^ " • 4° D D 



+ 108.7. There remained in the distilling flask 70 grams of hard, yellow resiu 



with properties similar to those detailed under experiment 3. 



(5) Acid and saponification numbers of two samples of balao. 



Acid number 

 Saponification number 



(1) 



13.0 



(2) 

 lO.O 



18.5 



34.16 



