RESINS 47 



The volatile portion of elemi resin is called elemi oil and 

 is usually obtained by steam-distilling the resin. Clover collected 

 samples of elemi resin from different trees. These samples were 

 distilled and the optical rotation, specific gravity, and refractive 

 index of these various distillates determined. The results 

 varied considerably. Clover concluded that the great variation 

 found in the different oils was due to a difference in the resin 

 obtained from different trees. The following experiments per- 

 formed with a sample of Manila elemi show the general proce- 

 dure followed throughout in working with this resin. 



Sample II was collected near Atimonan, Tayabas, from a tree having 

 a diameter of about 3 feet near the base and laden with unripe nuts. The 

 sample, of which 815 grams were used, was softer than the previous one. 



The first distillate at 125°, amounted to 50 grams (II, A) ; the second 

 at 210° (II, B), was 123 grams; the third at 250° (II, C), was 30 grams. 

 The terpene oil was distilled from II, B at reduced pressure and the residue 

 added to II, C. The total terpene oil was 132 grams or 16.2 per cent; the 

 high-boiling oil, 71 grams or 8.7 per cent. 



II, A was decanted from a small amount of water which collected with it. 

 It was then distilled twice at 36.5 millimeters, passing over the second 

 time almost completely between 82°. 5 and 83°. 5; three-fourths of it dis- 

 tilled at almost a constant temperature or at most within 0°.25 (II, A, 



30 

 purified), a— = +100°. The product gave no test for phellandrene. 



With bromine in acetic acid the 104° to 105° melting limonene tetrabromide 

 was obtained and a granular nitrosyl-chloride was also readily formed. 

 It also gave dipentene dihydrochloride melting at 50°. It was distilled 

 from metallic sodium, after which it boiled completely between 176° and 

 177°, accordingly at a slightly lower temperature than I, A, purified; 

 however, it possessed the same odor and, so far as could be determined, 

 was identical in all other respects. 



II, C stood for over a year and was then fractionated twice at reduced 

 pressure, whereupon about one-half of it was obtained as a light, yellowish- 

 green product, boiling completely from 167° to 169°. 5 at 35 millimeters 

 (II, C, purified). 



Sp. gr., ^^ = 0.9522. a^^=-2°.7. rt^ = 1.4973. 



Clover was able to isolate various terpenes such as dextro- 

 limonene, dextro-phellandrene, terpinene, and terpinolene from 

 different samples of the resin. 



Clover concluded that: 



The combined results obtained by a careful examination of the oils 

 obtained from 21 individual samples of resin establish the true composi- 

 tion of elemi oil so far as these samples may be considered as representa- 

 tive of the aggregate product. In several cases, notably in the last sample 

 examined, substances were obtained which were not encountered in any 

 other; it seems possible, therefore, that were the investigation continued, 

 still others would be found in which new constituents would appear, 



