﻿68 BACON AND FREER. 



compared with isopropyl alcohol was isolated. The high-boiling frac- 

 tions from the separation of the above substances gave pinakone, a small 

 quantity of phoron and, presumably, reduction products of the latter. 

 Mesityloxide could not oe isolated. A portion of the reaction product 

 of sodium on acetone was found to be soluble in ether, this on careful 

 evaporation gave a yellow powder, 5 which oxidized in the air with remark- 

 able readiness. This residue, on acidifying, separates some oil, which 

 was isolated, and the presence of acetone was afterwards proven in the 

 solution. The high-boiling portion of the residue was phoron. These 

 high-boiling oils react rapidly with phenyl hydrazine. No isopropyl 

 alcohol and but very little pinakone can be found among the products 

 of decomposition of this soluble portion obtained by the action of sodium 

 on acetone, but by far the greater part of the condensation products 

 produced by the action of sodium on acetone are found in this residue. 

 In proportion as such condensation products are produced, the percent- 

 age of sodium in sodium acetone will be increased. 



In a recent number of the Journal of the Chemical Society G Millieent 

 Taylor has returned to the subject and comes to the remarkable conclu- 

 sion that acetone-sodium "consists chiefly of caustic soda mixed with a 

 small proportion of the sodium derivatives of alcoholic reduction and 

 condensation products of acetone." 



Apart from the fact that in her discussion Miss Taylor completely 

 ignored the careful description given by one of us of all of the products 

 obtained by the action of sodium on acetone, the statement which she 

 makes that "so-called sodium acetone contains 50.4 per cent of sodium" 

 would in itself be sufficient to cause some doubt as to the accuracy of 

 her results. In our opinion the fact that the product of the action of 

 sodium on acetone, when all acetone and solvent have been removed, on 

 acidifying regenerates acetone in large amount is conclusive enough 

 evidence of the existence of sodium acetone, and this fact was repeatedly 

 emphasized in the first series of papers on this subject, but ignored by 

 Miss Taylor in her discussion. Nevertheless, we have deemed it neces- 

 sary to repeat the work, and here it may be said that at no time, even 

 with the absence of all of the usual precautions, were we able to encounter 

 as much as 50 per cent of sodium in the derivative of the action of 

 sodium on acetone; in ether we obtained 29.2 to 30.9 per cent of sodium 

 and the highest determination (in petroleum ether) gave us 35.5 per cent, 

 these results being in accord with those previously obtained by one of us. 

 In carefully reading Miss Taylor's paper it becomes evident that she 

 always had a red substance present after the action of sodium on acetone, 

 both in her experiments on the determination of the amount of sodium 



5 Our work shows that, under proper conditions, this residue is white. 

 "Journ. Chem. Soc. (1906), 89, 1258. 



