﻿1 2 CLOVER. 



taken— (1) from 167°.5 to 169°; (2) from 169° to 172°. The first 

 fraction showed a rotation of -|-110 o .l and the second -|-113 .1. The 

 first fraction was also tested in a number of ways in the hope of isolating 

 a crystalline substance other than phellandrene nitrite, but with negative 

 results. On again distilling, its initial boiling point was lowered only 

 about 0°.5. Both fractions deposited crystals on standing which were 

 similar in appearance to those already noted in the oils derived from the 

 phellandrene-containing samples : 



VTI,B, was distilled at reduced pressure and after removal of the terpene 



oil, most of the remainder passed over within a few degrees. It was kept foi 



nearly a year before it was redistilled and it then yielded a product boiling 



from 165° to 168° at 35 millimeters, this constituting almost two-thirds of the 



original (VII,B, purified). The purified product was quite viscous, light-yellow 



30 30 



in color and of a mild, pleasant odor. Sp. gr., . =0.9730. n ',-. = 1.5015. 



VII, C, also stood a year before it was purified. After it had been distilled 

 twice, nearly all of the original substance was obtained as a product boiling 

 from 168° to 171° at 37 millimeters (VII,C, purified). Its boiling point is 

 seen to be a little higher than that of VII,B, purified, but there is very 

 little difference in the other physical properties, so that no marked distinction 

 exists between the two products due to the different temperatures at which they 



were removed from the resin. Sp. gr., 3 4 °=0.9689. <* p=— 2°.5. n ^ = 1.5005. 



The work with the following samples was carried out in essentially the 

 same manner as that already detailed, although no particular attention 

 was paid to the amounts of oil obtained. In the interim which occurred 

 at this point of the work, it was found that it was not necessary to use 

 great precaution as to temperature in removing limonene from the resin. 

 Therefore, when a sample was found to contain dextro-limonene, the 

 terpene was removed as completely as possible by heating the resin to 150° 

 or 160°. It was also found that phellandrene suffered a considerable 

 change at a temperature near its boiling point, and it was also thought that 

 terpinene as well would suffer alteration at a higher temperature, especially 

 when it was in contact with the resin. However, it was desirable to remove 

 all of the terpene possible, so that the purified product could be used for 

 further work. In those samples not containing dextro-limonene, the dis- 

 tillation was carried as far as possible at 125° and then the oil bath was 

 heated gradually to 150° and the distillation made as quickly as it could 

 be done. The entire distillate was taken in only two portions, and the 

 high-boiling part was seldom taken beyond a temperature of 235°. In 

 order to obtain the correct data for the physical properties of the terpene 

 oils, they were, unless otherwise stated, first shaken with a dilute solution 

 of potassium hydroxide which freed them from an unpleasant odor often 

 noticed, and then distilled twice in vacuo, allowed to stand over night 

 with solid potassium hydroxide and then carefully redistilled, discarding 

 the first 2 or 3 cubic centimeters of the distillate. In a few samples, the 

 high-boiling oil was disregarded entirely. The following samples were 



