1869.] Mr. C. Schorleinmer on the Derivatives of Propane. 31 



which are formed are (1) the secondary chloride, (2) probably propylene 

 dichloride, and (3) trichlorhydrine*. 



In my last communication I have already called attention to the dif- 

 ferent behaviour of ethane and propane under the action of chlorine. A 

 further instance is the formation of trichlorhydrine, the chemical struc- 

 ture of which is most probably expressed by the formula C H 2 CI— C H CI 

 — C 2 HC1, whilst by substituting 3 atoms of hydrogen by chlorine in 

 ethane, the compound C H 3 — Cl 3 is formed. 



The liquid from which I had separated the trichlorhydrine was again 

 treated with chlorine in the direct sunlight for several days. On distilling 

 it afterwards, it came over between 200° and 250°. The portion boiling 

 between 200° and 205° solidified in the receiver as a white, crystalline 

 mass. In order to remove from it an oily liquid which it contained, it was 

 pressed between filter-paper and recrystallized repeatedly from alcohol. 

 The analysis conducted to the formula C 3 H 4 Cl 4 . 



(1) 0*1462 gave 0*5460 silver chloride and 0*0035 silver. 



(2) 0*1282 gave 0*4051 silver chloride. 



Found. 



Calculated for C 3 H 4 Cl 4 . I. II. 



78*01 per cent. 78*02 per cent. 78*24 per cent. 



Tetrachloipropane, as this compound may be called, crystallizes from a 

 hot alcoholic solution in small needles, four or eight of which are generally 

 grouped together, forming a regular star. Its smell strongly resembles 

 that of camphor. Exposed to the air, it volatilizes pretty quickly ; heated 

 in a test-tube, it fuses, subliming rapidly at the same time. In a sealed 

 capillary tube it melted at 177°-178°, and solidified again at 176°-175°. 



The liquid boiling between 205° and 250° was very little acted upon by 

 chlorine even in the brightest sunshine and presence of iodine • also treat- 

 ment with potassium chlorate and fuming hydrochloric acid produced little 

 effect, as, after acting upon it for several days, the liquid boiled again 

 between 220° and 250°. The portion boiling between 243° and 250° was 

 analyzed : — 



0*1926 gave 0*6580 silver chloride and 0*0034 silver. 



Calculated for C 3 H 2 Cl 6 . Found. 

 84*86 per cent. CI. 85^04 per cent. 



This compound is therefore hexachlorpropane, C 3 H 2 Cl 6 , a colourless, 

 heavy liquid, which smells somewhat like camphor, and boils without 

 decomposition at about 250°. 



From these experiments it would appear that in propane we cannot re- 

 place by direct substitution more than six atoms of hydrogen by chlorine. 

 This observation gains in interest by the fact that in sextane (hexyl- 

 hydride) C 6 H 14 , from petroleum also not more than six atoms of hydrogen 



* Annal. Chem. Pharm. vol. cxxxvi. p. 48, and vol. cxxxix. p. 17. 



