﻿THE ACTION OF SODIUM OiN ACETONE. 



By Raymond Foss Bacox and Paul C. Freer. 

 {From the Chemical Laboratory, Bureau of Science. 



A number of years ago one of us x described the action of sodium on 

 acetone, showing that in the presence of absolute ether a white sodium 

 derivative is obtained which has 30.1T per cent of sodium (calculated 

 for sodium acetone 28.75 per cent) and which, on being added to dilute 

 hydrochloric acid, regenerates acetone. Subsequently, 2 in a second discus- 

 sion of the subject it was demonstrated that hydrogen is evolved when 

 sodium acts on acetone, and the resulting sodium derivative is again 

 described as being white, but turning red rapidly on exposure to air and 

 moisture. It was also shown that when this sodium derivative is added 

 to dilute hydrochloric acid and repeatedly extracted with ether, no con- 

 densation products of acetone (or at least only traces) could be isolated. 

 The sodium derivative therefore does not contain these condensation prod- 

 uces to any great extent. The mother liquors from a number of opera- 

 tions in the preparation of sodium-acetone were carefully retained, united, 

 washed with water, extracted with ether, and the residue distilled, a very 

 small quantity of mesityloxide and some higher condensation products 

 of acetone being isolated. Again, in another discussion of the subject, 3 

 bv acting on sodium under xylene, with acetone, 62.7 per cent of the theo- 

 retical amount of hydrogen was obtained (this observation was subsequently 

 confirmed by Beckmann and Schliebs *), and in the same paper, in discus- 

 sing the preparation and analysis of the sodium derivative of acetone, 

 it was shown that delay during the preparation of this derivative always 

 resulted in increasing the percentage of sodium. A large number of 

 samples of acetone- sodium were prepared, decomposed by dilute, ice-cold 

 acetic acid and united until a sufficient amount had been collected to study 

 the reaction products; acetone (isolated as the sodium-bisulphite com- 

 pound), isopropyl and ethyl alcohols were indentified among these; under 

 favorable circumstances as much as twice the quantity of acetone, as 



1 Am. Chem. Journ. (1S90), 12, 355. 



2 Ibid. (1891), 13, 320. 



3 Ibid. (1893), 15, 585. Aim. Chem. (Liebig)i 278, 116. 

 'Ann. Chem. (Liebig) (1896), 289, SO. 



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