﻿THE TERPENE OILS OF MANILA ELEMI. 9 



(III,A) and then at 210° (III,B). In all, 1SG grams of distillate were 

 obtained from 900 grams of resin. A further distillation was not made. 

 Ill, A was separated from a little water and redistilled three times 

 in vacuo. On the third distillation it passed over completely from 

 89° to 90° at 47 millimeters, a g= + 100°. 7. The purified oil had the 



same odor, boiling point, and optical rotation as the two previous terpene 

 products. 



III,B was fractionated once at reduced pressure and the high-boiling portion 

 was preserved for over a year. On redistilling, the major part was obtained as 

 an oil boiling completely from 1C0°.5 to 169° at 34.5 millimeters (III,B, pur- 

 ified). It was light yellow in color. 



Sp. gr., 3 4 °= 0.9887, a ^ = — 2°. 5. n p =1.5055. 



Sample IV was collected -near Unisan, Tayabas, from a good-sized tree, 

 nearly 3 feet in diameter near the base. The tree, which at the same time 

 bore no fruit, contained 8 or 10 pounds of soft resin. 



One thousand and eighty grams of the sample were distilled, first 

 at 125° (IV,A), then at 210° (IV,B), and finally at 250° (IV,C). 

 The total terpene oil obtained from this sample was 152 grams or 14 

 per cent, and of high-boiling oil, 145 grams or 13.4 per cent. 



IV,A was redistilled twice at 65.5 -millimeters and on the second dis- 

 tillation it passed over completely at this pressure from 95°. 5 to 9 7°. 5 



on 



( IV, A, purified) . It was almost optically inactive, a' D = -|- 4°. It gave 



no test for phellandrene and in a check experiment in which a very small 

 proportion of phellandrene was added to the oil, this was easily detected. 

 No crystalline hydrochloride could be obtained on treatment with hydro- 

 chloric acid gas in cold, glacial acetic acid, nor could a crystalline bromide 

 be separated on saturation with bromine, either in acetic acid or in a 

 mixture of amyl alcohol and ether, as has been recommended by Baeyer 

 and Yilliger. 11 No solid nitrosyl-chloride could be formed. A good 

 quantity of terpinene nitrite was obtained by using the method recom- 

 mended by Wallach, the crystals appearing in a short time. When 

 recrystallized from alcohol, this substance melted at 155°, softening a 

 little below that temperature. The oil was distilled over metallic sodium, 

 after which it boiled completely from 174° to 176°. It stood nearly a 

 year in a partially filled, glass-stoppered bottle ; it was then redistilled with 

 steam, separated from water and dried over solid caustic potash. 

 Boiling point, 174° to 175°. 5. Sp. gr., 3 4 °= 0.8358. a ^ f 4°.3. 



n 



30 



^=1.4756. The product still gave a good yield of terpinene nitrite 

 and in all other respects it behaved as it had one year previously. It 

 appears to be almost pure terpinene. 



n l!n: <l. chem. Ges. (1894), 27, 448. 



