﻿THE TERPENE OILS OF MANILA ELEMI. 15 



Sample XIII was a large accumulation, somewhat incrusted, taken from 

 a medium-sized tree with no fruit. The purified terpene oil was found to be 

 pure dextro-limonene. Boiling point, 176°. 5 to 177°. 5; *??= -j- 100°. 1 

 (XIII A Purified). 



From the high-boiling oil, after distilling three times, a minor portion 'was iso- 

 lated which boiled completely within 3°. Sp. gr., 3 .°=0.9969; /* '^=1.5968 

 (XIII,B, purified). 



Sample XIV was taken from a medium-sized tree containing fruit. 

 The resin was moderately soft. The purified terpene oil boiled 



from 91°. 5 to 93° at 60 millimeters. Sp. gr., 3 4 °=0.8322;ag=+105°l; 



on 



n jy =1.4694 (XIV, A, purified). The oil gave a heavy precipitate 



of phellandrene nitrite which, when recrystallized twice from acetic 

 ester without warming., melted at 119° to 120°. To judge from the 

 boiling point, the oil appears to be nearly pure phellandrene although 

 the rotation is considerably lower than that of the phellandrene from 

 Sample V. 



The purified heavy oil, which constituted three-fourths of the total, boiled 

 from 167°.5 to 170°.5 at 35 millimeters (XIV,B, purified). Sp. gr., 3 4 °=0.9482; 

 a 't) = — 2°; n "p. =1.4957. It was quite viscous and yellow in color. 



Sample XV was obtained from a very large tree containing no fruit. 

 It was quite soft. The purified terpene oil boiled from 88 s to 91° at 60 



millimeters. Sp. gr., 3 4 °= 0.8336; a g= +112°. 7; n'^= 1.4678. The 



initial boiling point was a little below that of phellandrene and the 

 product was evidently a mixture. It gave a heavy precipitate of phel- 

 landrene nitrite which, when purified by recrystallization from acetic 

 ester without warming, melted at 119°. 5 to 120°. 5. The oil redistilled 

 at ordinary pressure from 169°. 3 to 172°. The distillate was divided 

 into two fractions which showed practically the same rotation, a trifle 

 lower than the original. Xo other crystalline derivatives could be 

 obtained from the oil. The odor is at once suggestive of the oils from 

 Samples VII and X, which this oil resembles in most respects. During 

 the purification, crystals were noted in the small residue contained in the 

 distilling flask. Crystals also separated from the heavy oil which had 

 been redistilled once and allowed to stand. 



Sample XVI was obtained from a good-sized tree about 3J feet in 

 diameter near the base, and containing no fruit. The resin was fresh 

 and soft. The purified terpene oil boiled completely from 89° to 90°.S 

 at 56.5 millimeters, most of it going over at almost a constant temper- 

 ature (XVI, A, purified), a p = -f 129°. 8; in a 5-centimeter tube the 



