KETONE FROM OLEIC ACID. 157 



Oleic acid is an unsaturated acid which is produced commercially 

 in ever>^ city in Australasia, and is therefore available in large 

 quantity. Hence it appeared that it would be interesting to study the 

 action of heat upon barium oleate in order to find whether a ketone 

 of the type CnHoii — 40 could be obtained, and what compounds other 

 than the ketone would be produced. Further, it appeared that if oleone 

 is capable of existence, it should be a compound of interest from the 

 following points of view : — 



I. It should, according to the Wislicenus hypothesis, be capable of 

 existence in three stei-eo-isomeric forms, there being two ethylene 

 linkages in the compound. Two of these should yield one oxime each, 

 the mixed ketone should yield two oximes. 



II. The ketone should yield a tetra brom. compound which might 

 be expected to give up hydro-bromic acid yielding a still more un- 

 saturated ketone of the type CnHoii — SO, of which no members are 

 known. 



III. Since the distillation of a mixture of the barium salts of two 

 different saturated acids produces a mixed, ketone, the distillation of a 

 mixture of the barium salt of oleic acid with the barium salt of a 



saturated acid might be expected to yieid a ketone, ^CO, 



containing only one ethylene linkage. 



The following is a sinnmary of the results so far obtained : — 

 On distillation of barium oleate under diminished pressure an oily 

 liquid was produced, which, on cooling, deposited ciystals. The disr 

 tiliate was fractionated under diminished pressure, and the higher 

 boiling point products were cooled and filtered. The crystalline product 

 thus obtained was recrystallised from alcohol, and was shown by the 

 analysis and molecular weight determination to have the formula 

 CajHggO, thus agreeing with that calculated for oleone. From this 

 compound an oxime was prepared and a determination of the nitrogen 

 made. The value obtained indicated that the nitrogen compound was 

 an oxime C34HggC = NOH. 



A determination of the bromine absorption of the ketone in 

 cliloroform solution showed that it had combined with two molecules 

 of bromine. It was considered possible that the filtrate from the 

 crystalline ketone might contain an isomeric liquid ketone. An 

 analysis of this filtrate indicated that its composition could almost be 

 represented by the formula C35llg(;0 ; the bromine absorption, how- 

 ever, was somewhat lower than that required by the pure ketone. 



The lower boiling point fractions obtained in the distillation of 

 the barium oleate were refractioned repeatedly, but with the quantities 

 available no product of constant boiling point could be isolated. 



Attempts to prepare mixed ketones from mixtures of the barium 

 salts of oleic acid with the salts of acetic and benzoic acids were un- 

 successful. 



