﻿THE TERPENE OILS OF MANILA ELEMI. 7 



it was found much better to distill the resin in a vacuum. It was also 

 found that the high-boiling oil could almost completely be removed from 

 the resin at a pressure varying from 8 to 15 millimeters, with practically 

 no decomposition of the latter. The resin, to introduce it into the distill- 

 ing flask, was first placed in a beaker and immersed in an oil bath which 

 was kept at a temperature of from 100° to 125°, depending on the ease 

 with which the resin became fluid.' The latter was then poured into the 

 flask and the terpene oil distilled over in vacuo, the pressure being 

 gradually decreased to 10 or 15 millimeters as the water in the resin 

 passed over; the oil bath was kept between 125° and 150°. The distilla- 

 tion was always made as quickly as possible and in no case was purified 

 terpene oil ever taken from a product which had been heated higher than 

 150°. Frequently a second distillate was then taken by heating to 200°, 

 at which temperature practically all of the terpene, but only a portion of 

 the high-boiling oil may be removed. If the resin is quite fresh, most of 

 the heavy oil will have passed over before the oil bath reaches 230°, but 

 with an old product it is difficult to maintain a high vacuum, so that the 

 oil bath must be heated to 250°. At this temperature, with fresh mate- 

 rial there is very little if any decomposition of the resin, but with that 

 which is old it is possible to remove only a small portion of the high- 

 boiling oil because of the increasing difficulty of maintaining a vacuum as 

 the temperature is raised beyond 200°. In several instances, the purified, 

 high-boiling oils derived from fresh resin at a temperature of 200° were 

 found to be identical with those obtained from the same samples when, 

 in some cases, it was raised as high as 250° ; so that it is quite certain 

 that no changes have been brought about in these oils by the high 

 temperature. 



Sample I was collected in July near Unisan, Tayabas Province, Luzon, 

 from a relatively young tree about -1-0 feet in height, having a diameter 

 of about 2 feet near the base. There was no fruit on the tree and its 

 owner said it never had borne any fruit. The resin, of which 1,035 

 grams were used, was drier than most of the samples. 



The first distillate (I,A) was taken at 140° and amounted to 54 grams; the 

 second up to 210° (I,B) amounted to 75 grams; and the third up to 250° (I,C) 

 was 45 grams. The terpene oil was distilled from I,B in vacuo and the residue 

 added to I,C. The total terpene oil amounted to 110 grams or 10.6 per cent, and 

 the total high -boiling oil to 04 grams or 6.2 per cent. 



I,A was redistilled twice at 54 millimeters; it passed over completely 

 the second time from 93° to 94° (I, A, purified), a ™= -f 99°. 6. The 

 oil gave no test for phellandrene and it was found that on the addition 

 of even 1 per cent of an oil known to be nearly pure phellandrene it 

 responded plainly to the test when the solution was kept very cold. 

 In the proportion of 1 to 200 no test could be obtained. With bromine 

 in acetic acid, .limonene tetrabromide was obtained; melting point, 



