382 Action of Pentachloride of Phosphorus on Malic Acid. 



The distillate was then transferred to a retort and heated. 

 Large quantities of liquid came over at 110° C, which consisted 

 of oxychloride of phosphorus : after a time the thermometer 

 began gradually to rise ; when it had reached 160°, the retort 

 and contents were allowed to cool to 120°; dry air was then 

 passed, in order to separate as much oxychloride of phosphorus as 

 possible ; heat was again applied, and the product distilled. It 

 commenced distiUing at about 170°, the thermometer gradually 

 rising ; in fact no fixed boiling-point could be obtained, as the 

 product decomposed with evolution of hydrochloric acid. 



The substance thus obtained is a colourless mobile liquid, 

 heavier than water ; when added to cold water, it sinks as an oil. 



With alcohol it reacts poMerfuUy, producing an etherial body j 

 with ammonia it forms a white, nearly insoluble substance. 



We have not been able to obtain this body sufficiently pure 

 for analysis, consequently have had to content ourselves with 

 the analysis of its derivatives. 



Action of Water on thi/t Chloride. 



This body, when exposed to atmospheric moisture for a few 

 days, is entirely converted into a white solid mass. A similar 

 result is obtained if it be heated with water. Hydrochloric acid 

 is formed, and, on cooling, the liquid deposits the new body ; 

 this, when washed with cold water and recrystallized from boil- 

 ing water, is obtained in a state of purity. Two combustions of 

 this substance gave the following numbers : — 



I. '3715 of substance gave -5597 of carbonic acid and -1233 

 of water. 



IT. -4200 substance gave '6372 of carbonic acid and 'ISGS 

 of water. 



Pcr-centage composition : — 



I. II. 



Carbon . . . 41-07 41-2 



Hydrogen. . . 3'60 3-6 



These numbers agree with the formula C^ H"* 0^ as may be 

 seen from the following Table : — 



Theory. Mean of experiment. 



41-13 

 3-60 



116 1000 



This acid is e^ndently fumaric acid ; it cannot be maleic, as it 

 is difficultly soluble in water. 

 The ether obtained by the action of the above chloride on 



