338 BROOKS. 



of the speeimeu passed quickly into solution on the addition of chloroform, but 

 there remained a large amount of white, amorphous, flocculent substance resem- 

 bling the insoluble amorphous compound often obtained bv heating a solution 

 of the crystals. This chloroform solution deposited crystals on the addition 

 of ligToin which were identical with the original substance. 



The conclusion that the crystalline substance undergoes pohTuerization 

 when heated, either alone or in solution, \-ielding the amorphous, in- 

 soluble compound, appears to be justified. The behavior of the com- 

 pound toward sodium acid sulphite supports the conclusion that one 

 substance only is present originally. I have found that, contrary to the 

 experiment described by Bacon, the crystalline substance reacts quan- 

 titatively M-ith sodium acid sulphite. 



Twenty grams of the substance were dissolved in a mixtui-e of alcohol and 

 benzene and vigorously shaken in a shaking machine for four hours with a 

 concentrated solution of sodium acid sulphite. On working up the reaction 

 mixture, the benzene solution on spontaneous evaporation gave 0.2 gram of 

 amorphous substance which apparently was identical with the polymerization 

 product. The original material therefore had passed practically quantitatively 

 into the aqueous acid sulphite layer. On treating t'le aqueous solution with 

 sodiruu carbonate in the usual manner, nothing separated, nor did any substance 

 separate on warming a small portion of the mixture. 



Sodium hydroxide failed to precipitate anything from another small test por- 

 tion. The solution was extracted with chloroform before and after making 

 alkaline, but with no result. The aqueous-alcoholic solution was then gently 

 evaporated on the steam bath. When quite concentrated, an oily layer was 

 salted out which was separated from the remaining solution. This viscous, syrupy 

 substance was exceedingly soluble in water. On standing iii vacuo over sulphuric 

 acid the mass slowly crystallized. Ignition of a small fragment on a platintmi 

 spatula showed it to be largely organic, the substance burning vigorously with 

 a smoky flame. The residue was sodium sulphate and sulphite. This exceed- 

 ingly soluble and stable substance is evidently a compouna of sodium acid sulphite 

 with the whole or at least the ketone part of the original substance. Hydrochloric 

 acid caused nothing to separate from concentrated solutions of the sodium com- 

 pound. The aqueous solution, slightly acidified with acetic acid, gave no pre- 

 cipitate after the addition of sodium acetate and phenylhydrazine acetate. 



What apparently is the free acid, of which the sodium compound is the salt, 

 was prspared by digesting a few giams of the salt on the steam bath with 

 glacial acetic acid. Sulphur dioxide was evolved, and after the mixture was 

 evaporated nearly to dryness it was extracted with chloroform. Addition of 

 ligroin to the concentrated chloroform solution gave a very small yield of an 

 oily substance, the physical properties of which were totally unlike that of the 

 original material. This oil could not be made to crystallize. 



Attempts to recrystallize the sodium salt from absolute or 9-5 per cent alcohol 

 were without result. 



A small amount of the sodivun salt in solution was slowly concentrated with 

 an approximately equivalent quantity of barium chloride. The crystals deposited 

 proved to be only barium chloride. 



The behavior of this ketone compound on treatment with sodium acid 

 sulphite, and the impossibility of regenerating th« original substance 



