﻿10 CLOVER. 



IY,B was distilled under reduced pressure and the low-boiling portion 

 was rcfractioned three times under the same conditions. On the third 

 distillation it passed over completely within a range of 2°. 5 or 3° and was 

 evidently not so pure a product as that obtained from IV,A, although 

 it gave a good yield of terpinene nitrite. Tt appears that in this case, 

 as well as with the samples containing phellandrene, there is some altera- 

 tion in the terpene when it is removed from the resin at higher 

 temperatures. 



IV,C stood for nearly a year; it was then redistilled twice in vacuo and a 

 product obtained which constituted the major portion of the original material 

 and which passed over completely between 171° and 174° at 39 millimeters 

 (IV,C, purified). It was of a light yellowish-green color and had a mild, 

 pleasant odor. It was much less viscous than any of the high-boiling oils pre- 

 viously isolated and also had a much higher specific gravity. It had very little 



optical activity. Sp. gr., 3 4 °=1.0315. a^= — 1°.2. n p=1.5159. 



Sample Y , which was moderately soft, was obtained from a tree stand- 

 ing close to that from which Sample II was taken. The tree was laden 

 with unripe nuts. 



One thousand grams of the resin were distilled, first at 125° and, 

 excluding 3 or 4 grams of water, the distillate amounted to 61 grams 

 (V,A). The second distillate was taken at 210°and weighed 124 grams 

 (V,B) ; the third was taken at 250° and was 70 grams (V,C). The total 

 terpene oil was 97 grams or 9.7 per cent and the high-boiling oil was 158 

 grams or 15.8 per cent. 



V,A was separated from water and redistilled twice at 43.5 millimeters. 

 On the second distillation it boiled almost completely from 82°. 7 to 84° 

 at this pressure (V,A, purified). Its odor was very pleasant and mark- 

 edly different from that of any of the terpene products previously 



obtained, a j?=-\- 122°. 6. It yielded a very heavy precipitate of phel- 

 landrene nitrite. Neither a solid bromide nor a uitrosyl-chloride could 

 be obtained by the methods ordinarily used. The product appears to be 

 almost pure phellandrene. Its boiling point can be seen to be 3° or 4° 

 below that of the limonene oils and about 2° below that of the terpinene 

 oil. On standing in a partly filled, glass-stoppered bottle, a small amount 

 of a good-sized, colorless, prismatic crystals appeared about the walls of 

 the bottle. 



V,B was distilled at reduced pressure, but after the removal of the terpene 

 oil the higher-boiling portion passed over gradually, indicating that only a 

 minor part of it could be isolated as a constant-boiling product. Unfortunately, 

 most of this high-boiling distillate was lost in an accident, but a small quantity 

 of it, on standing, deposited crystals similar to those found in V,A. 



Sample VI was obtained near Atimonan, Tayabas. The tree was an 

 unusually large one, being 5 or 6 feet in diameter near the base. A 

 large quantity of soft resin had accumulated from a number of cuts. 



