374 



Mr. Schorlemmer on the Hydrocarbons 



[May 14, 



into a red resinous substance. It dissolves very easily in fuming nitric 

 acid ; on boiling this solution for some time the oil is converted into a 

 white solid, which separates as crystalline powder on addition of water, and 

 which crystallizes from alcohol in large flat needles, I did not obtain suffi- 

 cient of this compound for a satisfactory analysis ; also the quantity of suc- 

 cinic acid obtained is always very small in comparison to the amount of 

 hydrocarbon used, which is to the greatest part oxidized to water and car- 

 bonic dioxide. 



The distillate obtained after the oxidation contains, besides unaltered 

 hydrocarbon and diluted nitric acid, also a small quantity of fatty acids and 

 of nitriles. I have only examined those which were derived from diamyl. 

 The liquid was neutralized with sodium-carbonate, the diamyl separated 

 and distilled ; after the hydrocarbon had passed over, the thermometer rose, 

 and between 230°-235° a small quantity of a yellowish liquid passed over, 

 which had the characteristic smell of the nitriles of the fatty acids. On 

 heating it with an alcoholic potash solution, ammonia was given off. I tried 

 to convert the potassium-salt thus obtained into the silver-salt, but obtained 

 the latter only in small quantity and in an impure state, so that I could 

 not analyze it. The boiling-point of the nitrile agrees with that calculated 

 for caprinitrile, C^^ H^^ N. The solution of the sodium-salts was evaporated, 

 and the residue distilled with a small quantity of nitric acid ; the acid dis- 

 tillate, on which oily drops swam, smelt of valerianic acid. It was neu- 

 tralized with ammonia, and precipitated with silver-nitrate in three fractions. 



(1) Fraction contained 45*27 per cent, of silver. 



(2) „ „ 46-84 



(3) „ „ 49-50 



Silver-oenanthylate contains 45-57 per cent. Ag, and silver-valerate 51-67 

 per cent. Ag. The fatty acids, which were formed by oxidizing diamyl 

 with nitric acid, consisted therefore of oenanthylic, valerianic, and no doubt 

 also caproic acids. 



I have further examined the products which are obtained by oxidizing 

 the amyl acohol derived from petroleum. As I have shown in a former 

 communication*, the amyl compounds obtained from fusel-oil appear to 

 be identical with those from petroleum, as they have the same specific gra- 

 vity and the same boiling-points ; the only difference which I found is that 

 the boiling-point of amylhydride is about 4° higher than that derived from 

 the fermentation alcohol. The whole quantity of amyl alcohol which I had 

 prepared from petroleum was only 3 grammes. As oxidizing mixture I 

 used a solution of two parts of potassium bichromate in ten parts of water, 

 to which was added three parts of sulphuric acid. The alcohol was added 

 to the cold liquid, and the reaction moderated by surrounding the flask with 

 cold water. As soon as the reaction was finished the liquid was distilled, 

 and the acid distillate, which smelt strongly of valerianic acid, neutralized 

 * Proceedings of the Royal Society, vol. xv. p. 131. 



