1868.] Destructive Distillation of the Sulphobenzolates. 65 



Phenylene Sulphide. 



The dark-coloured residue in the retort which did not come over at 

 300° C. was distilled from a copper retort having a bent glass tube luted 

 into it. The orange-coloured distillate, on standing a few days, deposited a 

 considerable quantity of large transparent plates. These were drained as 

 much as possible, and freed from adhering oil by pressure between paper. 

 The partly purified crystals were extracted with hot spirit to remove the 

 bisulphide of phenyl and other impurities, and then crystallized from benzol 

 or bisulphide of carbon. A crystallization from spirit rendered them quite 

 pure. 



I. *243 grm. gave *592 carbonic anhydride and "086 grm. water. 



II. *221 grm. gave "539 carbonic anhydride and '076 grm. water. 



III. *301 grm. gave '652 baric sulphate. 





Theory. 



I. 



II. 



III. 



Mean. 



C 6 = 72 , 



66-67 



66-45 



66-53 





66-49 



H 4 = 4 



3-70 



3-93 



3-82 





3-87 



S = 32 . 



. 29*63 







29-71 



29-71 



108 



100-00 











The analyses of this substance lead to the formula C G H 4 S, sulphide of 

 phenylene. It crystallized in long lustrous prisms, which are quite trans- 

 parent and colourless. Is insoluble in water, slightly soluble in cold al- 

 cohol (about 400 parts), but more so in hot. It is far more soluble in 

 benzol and bisulphide of carbon, from the latter of which it may be ob- 

 tained in fine crystals, sometimes half an inch or more in length. It melts 

 at 159° C. and solidifies at 153°C. It dissolves in concentrated sulphuric 

 acid, forming a solution of a magnificent purple colour, and which when 

 largely diluted with the concentrated acid appears purplish red. On the 

 addition of water the colour disappears, and a crystalline precipitate is 

 produced, apparently the unaltered phenylene sulphide. With concen- 

 trated nitric acid a reaction takes place, red fumes are evolved, and a crys- 

 talline substance produced, probably a nitro-substitution compound. This 

 I have at present under investigation. 



Sulphob?'omide of Phenylene. 



When crystals of the phenylene sulphide are exposed to bromine-vapour 

 they combine with it and turn black, forming sulphobromide of phenylene. 

 The best method, however, to obtain this pure, is to add perfectly dry 

 bromine in slight excess to a cold saturated solution of sulphide of pheny- 

 lene in dry bisulphide of carbon, when the compound is precipitated in 

 the form of minute black prisms. These are immediately collected, washed 

 with cold dry carbonic disulphide, pressed, and the bisulphide of carbon 

 removed by placing them under the receiver of an air-pump, rapidly ex- 

 hausting the air, and allowing it to reenter several times. It is then 



VOL. XVTT. F 



