1865.] Destmctive Distillation of the Sulphobenzolates. 353 



stance introduced into the retort should not exceed 25 to 30 grammes at 

 each distillation. 



Florence flasks can be used ; but, owing to their bad conducting-power 

 and the high boiling-point of the oil, the result is not so favourable. When 

 the distillation is properly conducted in a copper retort, the dried sodium- 

 salt yields from one-fourth to one-fifth of its weight of crude oil. 



The crude oil was separated from the supernatant layer of water, and 

 distilled in a retort furnished with a thermometer. It began to boil at 

 80 C., and then rose slowly to 110 C., the distillate between these tem- 

 peratures consisting of a small quantity of water and benzol. When the 

 water had all passed over, the boiling-point rose very rapidly to 290 C., at 

 which temperature the greater portion of the liquid distilled over, leaving 

 a black tarry residue in the retort. This black residue, when more strongly 

 heated, gave a further quantity of an oily body, which, when rectified, 

 first yielded the substance boiling at about 290 C., and above 300 C. a 

 liquid which on standing some weeks deposited a small quantity of crystals. 

 The quantity boiling between 290 and 300 C. was about two-thirds the 

 weight of the crude oil. 



The rectified oil between 290 and 300 C. was again distilled, when 

 nearly the whole of it came over at 292*5 C., the boiling-point being re- 

 markably constant. After another rectification in a current of hydrogen, 

 it was subjected to analysis the carbon and hydrogen being determined 

 by combustion with oxide of copper and a current of oxygen, and the sul- 

 phur by ignition with carbonate of sodium and oxide of mercury. 



I. -603 grm. oil gave 1'708 grm. CO a and -292 grm. H 2 O. 

 II. '595 grm. oil gave 1'679 grm. CO 2 and '288 grm. H 2 O. 

 III. -237 grm. oil gave '302 grm. sulphate of barium. 

 IV. ! 275 grm. oil gave '354 grm. sulphate of barium. 



Theory. I. II. III. IV. Mean. 



C 12 =144 77-41 77-25 76-98 ..- .. 77-12 



H 10 = 10 5-38 5-38 5-38 .. .. 5'38 



S = 32 17-20 .. .. 17-48 17'51 17'49 



186 99-99 



The formula C 12 H 10 S, deducible from these analyses, is that of sulphide 

 of phenyl, or a body isomeric with it. When pure it is nearly colourless, 

 having only a very faint yellow tinge, and an aromatic but slightly alliaceous 

 odour. It has a high refractive power, sp. gr. 1-119, and boils at 292-5. 

 It is insoluble in water, very soluble in hot spirit, from which it partially 

 separates on cooling, and is miscible in all proportions with ether, bisulphide 

 of carbon, and benzol. Its alcoholic solution, when mixed with bichloride 

 of platinum, gives a slight flocculent precipitate, which on standing resolves 

 itself into a reddish-coloured oil. Nitrate of silver and chloride of mercury 

 give no precipitate. 



When the oil \vas treated with sulphuric acid, it dissolved in small quan- 



