Art. LXXX.–Preliminary Note on the Production of one or more Alkaloids from Fixed Oils, by the Aniline Process.
[Read before the Wellington Philosophical Society, 17th and 31st August, 1878.]
My late successful production of alkaloids from our petroleums * induced me to apply the same process I used in that instance to the fixed oils, that is the process I name in the title of this paper, for brevity, the “Aniline Process;” one which, I may remind you, consists in first warming the petroleum, etc., to be treated, with nitric acid, by which numerous nitro compounds are produced; and, in the second place, deoxidizing these by nascent hydrogen, by which any hydro-carbons of the benzol series present
[Footnote] * Vide supra, Art. LXXVIII.
have a portion of their hydrogen replaced by the elements of nitrous acid, and subsequently, a portion of the oxygen of this acid removed, the ultimate result being that a nitrogenous substance is, produced which is a true alkaloid, in fact an amide, that is, a substance constructed upon the ammonia type, and which, in case of those produced from petroleum, has one equivalent of hydrogen of ammonia substituted by a hydro-carbon.
Now, so far as I know, this process has not been applied with any success to a fixed oil or fat, if applied at all; every constituent of such substances is indeed held to be constructed so differently to the petroleums and their allies, that we should not expect results upon them at all similar to those we get by the same means as applied to the petroleums.
However, by employing this process very carefully upon the purest olive oil I could get, I obtained as a resultant a liquid which manifested, to all the tests I could apply, the reaction of one containing an alkaloid.
By employing Stras's process to this liquid I separated an oily body which was in great part dissolved by weak acetic acid; the solution in this acid afforded dense precipitates with tannin, mercuro-iodide of potassium, sulpho-cyanide of potassium and zinc, a reddish precipitate with free iodine, and when evaporated with platino-chloride of potassium a granular yellow precipitate; this precipitate, when washed well with alcohol to dissolve any oil present in a free state, partially fused when gently heated, and then blackened, and as the heat was raised the black matter was consumed, and a grey mass of platina left.
These results clearly show that an alkaloid had been obtained from the oil used.
Several other vegetable oils gave similar results to these, and among the animal oils, cod-liver oil and sperm oil. The former oil was obtained from the fish by steam, so that the alkaloid produced is not to be referred to any product of decomposition made by securing the oil. That this alkaloid is not to be referred to the glycerine of these oils is proved by my inability to obtain an alkaloid in this way from glycerine itself; and further by the fact that Price's stearine, as sold in his candles, also affords me this alkaloidal substance. These candles do not contain glycerine, and are the best representation of a pure fat which I can at present get.
These facts open up a very interesting field for research, as they show one of two things, viz.:—First, that there are one or more hydro-carbons of the benzol or naphthaline series in our fixed oils and fats:—second, or that the acids of these substances are in part capable of furnishing alkaloids to the aniline process.
Whichever way it may prove to be, the matter is of an equal interest, for that there should be pure hydro-carbons mixed with the fixed vegetable and animal oils named, would be just as important a fact to know, as that
our oxygenated oils yield alkaloids to a process which hitherto has been considered applicable to hydro-carbon oils alone, and even of these but very few.
I should inform you that none of the oils, etc., cited above, when tested for alkaloidal matter gave any indication of its presence, although I operated in each case upon the same quantity of oil as that I used for the aniline process.
The constitution and precise character of the alkaloid or alkaloids I have thus formed I cannot at present describe to you, as I have not yet the leisure to prosecute this investigation to the end. I hope to take up this subject on some future day, but in the meantime I shall be glad to hear of any one continuing the research, as it can hardly fail to give results of great interest.
Postscript.–I have further pursued my investigations of this subject, and of the two alternatives I have submitted to you in respect to the derivation of the alkaloid I produce by this process, I accept that which assumes it to be a product of some hydro-carbon or hydro-carbons present in the oil or fat employed. I have produced alkaloids by this process from well-washed butter, the purest sperm, and olive oils; and I now make the general statement that there is present in all the fixed oils or fats, whether of vegetable or animal origin, whether in the organism or removed from it, a small quantity of one or more hydro-carbon oils, and that these, or at least some of them, are homologous with benzol.