1868.] Destructive Distillation of the Sulphobenzolates. 63 



titled, gave a liquid boiling constantly at 1 72°*5. This was subjected to 

 analysis with the following results : — 



I. '5345 grm. oil gave 1*280 grm. carbonic anhydride and *265 grm. 

 water. 



Theory. I. 



C 6 =72 65-45 G5-33 



H G = 6 .... 5-45 5-51 

 S =32 29-10 



110 100-00 



C H 1 



The numbers obtained correspond very closely with the formula G jj 5 !■ S, 



phenyl-mercaptan. When pure it is colourless, having an aromatic but 

 somewhat alliaceous odour, although not at all offensive. It has a high re- 

 fractive index, and boils at l/2 0, 5 C. Insoluble in water, but readily miscible 

 with alcohol, ether, and benzol. It is readily oxidized, yielding bisulphide 

 of phenyl. This takes place even when exposed to the air in imperfectly 

 closed vessels. 



Vogt* has described an oil which he obtained by the action of zinc and 

 dilute sulphuric acid on sulphobenzolic chloride, C 6 H 5 CI S 2 , and calls 

 benzyl-mercaptan, C 6 H G S. He says it boils at "about 165° C, and has 

 an extremely offensive odour." 



Ottof, by the action of nascent hydrogen on sulphophenylenethylene, 

 C H S O 1 



6 c H j ' obtained phenyl-mercaptan, which he showed to be identical 



with Yogt's benzyl-mercaptan, but the boiling-point is " between 170° C. 

 and 173°C." 



From the description given by Vogt and Otto, it is evident that the 

 phenyl-mercaptan obtained by the destructive distillation of sulphobenzo- 

 late of sodium in an iron retort is identical with theirs, and that the offen- 

 sive odour ascribed to it by Vogt is due to some slight impurity, probably 

 arising from the phosphoric chloride employed in the preparation of the 

 sulphobenzolic chloride. 



Phenyl-mercaptide of lead. — On adding acetate of lead to an alcoholic 

 solution of the mercaptan, a bright yellow crystalline precipitate was formed. 

 This when heated fused, and at a higher temperature was decomposed. 



Phenyl-mercaptide of copper was prepared in a similar manner, substi- 

 tuting acetate of copper for acetate of lead. On exposure to the air in a 

 moist state it became oxidized, forming cupric oxide and bisulphide of 

 phenyl, C 6 H 5 S, which may be extracted and crystallized from boiling 

 spirit. 



The compounds with mercury, chloride of mercury, and silver are iden- 

 tical with those described by Vogt. 



* Ann. der Chem. und Pharm. vol. cxix. p. 144. 



f Ibid. vol. cxliii. p. 211. 



