Tetrethylphosphonium and their Decomposition by Heat. 195 



acid, and not changed when warmed with caustic soda. As 

 this liquid seemed to consist of at least two substances, more 

 of the benzoate was decomposed, in order to obtain enough of 

 the mixture to be separated satisfactorily bj fractional dis- 

 tillation. This did not prove difficult, as one of the constituents 

 boiled below 100° C, while the other possessed a boiling- 

 point slightly above 200° C. Eventually two liquids were 

 obtained, one boiling from 80°-85°, and the other boiling from 

 210°-215° C. The former had an aromatic sweet smell, and 

 was insoluble in water. A combustion gave the following 

 results : — 



0-286 grm. gave '960 CO, and -213 H 2 0. 

 0=91-54:, H = 8*27. 

 Calculated Found 



for C 6 H 6 . 



C = 92-30 .... 91-54 

 H = 7-69 .... 8-27 

 Thus indicating that the substance was the hydrocarbon 

 benzol. 



The liquid possessing the high boiling-point of 210°-215° 

 C. had a sweet pleasant odour, and bearing in mind the results 

 obtained when the acetate was heated, we expected to find 

 phenylethyl ketone, which boils at 210° C, and yields on 

 oxidation acetic and benzoic acids. The liquid was therefore 

 boiled for some time with bichromate of potash and sulphuric 

 acid, and then distilled. The first portions of the distillate 

 were strongly acid, and were neutralized with ammonia. The 

 ammonia salt thus obtained gave with nitrate of silver a 

 crystalline salt, which was recrystallized and analyzed. 

 0'360 grm. gave 0*225 Ag. . =62*5 per cent. Ag. 

 Ag(C 2 H 3 2 ) .... = 64*6 per cent. Ag. 



The low percentage of silver found is possibly due to benzoate 

 of silver being present. The chromic-acid solution remaining 

 after the distillation was shaken out with ether, and the etherial 

 solution evaporated. A crystalline acid remained, possessing 

 the characteristic odour of benzoic acid. It was neutralized 

 with ammonia, and precipitated with nitrate of silver solution. 

 The resulting silver salt on analysis gave the following 

 numbers : — 



0*345 grm. salt gave *165 Ag. . =47*82 per cent. Ag. 

 Ag(C 7 H 5 2 ) =47*16 per cent. Ag. 



As the ketone seemed to be formed in fair amount by this 

 reaction, a considerable quantity of the benzoate was prepared 

 and subjected to the action of heat. In one experiment 

 10 grms. of salt gave 500 cub. centims. of gas (consisting 



O 2 



