DERIVATIVES OF ETHYL ALCOHOL. 59 



Takes up oxygen very rapidly, and occasionally takes 

 fire in contact with the air. Combines with sulphur 

 and carbon bisulphide, forming liquid compounds. Dis- 

 solves readily in all acids. The salts crystallize with 

 difficulty, with the exception of the hydriodate. The 

 salts are not decomposed by water. Oxidized by 

 means of nitric acid, it yields diethylphosphinic acid 

 (C 2 H 5 ) 2 PO.OH, a liquid. 



Triethylphosphine, (C 2 H 5 ) 3 P,is formed, when phos- 

 phorus terchloride is added drop by drop to an ethereal 

 solution of zinc ethyl and the resulting viscid com- 

 pound of zinc chloride with the phosphorus base dis- 

 tilled with potassa. Is most readily obtained by 

 heating 1 molecule of iodophosphonium, PH 4 I, with 

 3 molecules of absolute alcohol for eight hours 

 in sealed tubes at 180. On the addition of caustic 

 soda to the solution, it is precipitated. Colorless, 

 strongly refracting liquid, which possesses an almost 

 narcotic odor (in a dilute condition like hyacinthes), 

 perfectly insoluble in water, mixes with alcohol and 

 ether in every proportion ; specific gravity, 0.812 ; 

 boiling point, 127. 5. Combines slowly with acids 

 forming very easily soluble salts, which crystallize 

 badly. In contact with the air it forms triethylphos- 

 phine oxide (C 2 H 5 ) 3 PO, this being accompanied by an 

 increase in temperature and an assimilation of oxy- 

 gen. It crystallizes in needles, is exceedingly deli- 

 quescent, and boils at 240. Sulphur is also dissolved 

 by the free base, forming triethylphosphine sulphide 

 (C 2 H 5 ) 3 PS. This crystallizes from water in long, bril- 

 liant, white needles, which fuse at 94. 



Phosphethylium iodide, (C 2 H 5 ) 4 PL Is produced 

 when an ethereal solution of triethylphosphine is 

 mixed with ethyl iodide ; is also formed in the pre- 

 paration of triethylphosphine from iodophosphonium 

 and alcohol, and crystallizes from the liquid after the 

 addition of caustic soda and evaporation. Crystals, 

 easily soluble in water. Is not decomposed by caustic 



