H On subjecting dicthylamino to the same method we produce tricthyl amine (C.11, N). Triethylamino unites directly with iodide of ethyl, and the result is the formation of the iodide of tetrethyl C,H, ammonium N,I= (C,II,), N,I. On now treating this iodide with freshly-precipitated oxide of silver, iodide of silver is formed, and the hydrated o.ride of ictrethylammonium set free. The latter body s a powerful base, comparable only with caustic potash or soda. It saponifies oils, precipitates metallic oxides from their salts, is not volatile without decomposition, rapidly absorbs .carbonic acid and water from the air, is itself crystalline, and forms crystalline salts with acids, turns red litmus-paper blue, dissolves the cuticle, and, in short, behaves as though it were an inorganic alkali. Ethylamine is a colour less, volatile liquid of sp. gr. 0.696; vapour density, soluble in water in all proportions; acts like ammonia upou solutions of metallic salts, but, unlike ammonia, it dissolves recently-precipitated alumina. Diethylamine is also colourless, volatile, inflammable, and caustic boiling point, Triethylamine resembles ethylamine and cliethylamine, and forms a beautiful orange-coloured crystalline salt with biehloride of platinum, containing ( (C,H,), N, H CI, So much for the general method of procuring the greater part of the organic bases. Of course the iodide, and sometimes the bromide or chloride, of any alcohol radical may be employed, the amines formed containing that radical in the place of the ethyl in the example quoted. Moreover a primary amine may be acted upon by the iodide of a radical other than that it already contains, and the secondary amine thus formed acted upon by the iodide of a third radical different from either of the two existing in it, and finally the tertiary amine thus produced may be made to unite with the iodide of a fourth alcohol radical, and an ammouium called into existence having the four equiva lents of hydrogen substituted by four different electropositive radicals.
This method is important, not only in producing new organic bases, but as a means of ascertaining the constitution of an organic base after its composition has been determined by organic analysis. For ob viously, if the base will only unite with one molecule of an alcohol radical, it must be a tertiary monamine ; if with two, a secondary monamine ; if with three, a primary monamine. The process does not, however, tell us in all cases whether the unknown radical already present in the body is monatomic, diatomic, or teratomic. The natural bases conine and codeine have in this way been shown to he secondary and tertiary monamines respectively, while nicotine, quinine, cinch°. nine, quinidine, brueine, and strychnine are either tertiary monamines or tertiary diamines.
The following organic bases, mostly formed by the above general method, have already been mentioned in this Cyclopedia, but for details concerning them, have been referred to the present article. Their general properties are similar to those of the ethyl derivatives fully described above; their special characteristics will only therefore be given.
Illethylemine (N,1I,, C,H,) is frequently met with in organic decom positions ; it is a gas, but may be condensed by a freezing mixture ; it is inflammable, and at 55° Fahr. water dissolves 1150 times its bulk. Mmethylamine has not been isolated in a puro state. Trimethylamine (N(C,H,),) may often be recognised by its odour in the roe of her rings ; it boils at 41* Fehr. and is inflammable. Tetramethylammonium,
hyd. ox. (N (0,1I,)„ 0, HO), cryatallises in deliquescent needles; its salts also crystallise well. Methyltriethylammcrnium, hyd. ox.
0, HO ) is crystalline; its salts are very soluble in water. Propylamine (NII,C,H,) has not been much studied. But ylanane is a colourless liquid, lighter than water ; boiling point about 176• Fehr.; it forms stable crystalline salts. A mylamine C,II„) boils at Fahr. ; has a specific gravity of 01503, and is in&mmable. Diamylamine ii)s) boils at 333° Fahr. Tri wnylamine boils at 494'.0 Fehr., and much resembles diamylamine. Methyl.ethylamylamine (NC,11,C,11,C,,,11,,) is a colour less oil of agreeable aromatic odour; boiling point, 275° Fahr. Diethyl amylamine (N(C,II,),C,„H„) boils at 309"2 Fahr., and with iodide of methyl gives the iodide of methyl-diethyl-amylammonium. Tetramyl ammonium, hyd. ox. (C,,,H„),0 110) occurs in deliquescent crystals. Amyl triethylammoninm, hyd. ox. (N(C,„H„) HO) forms crys talline salts, but is not crystalline itself. Tricetylamine (N(C„H„),) crystallises in colourless needles; melting point, 102.2° Fehr. Ally.
laming (N distils between and 374° Fahr. • A second method of forming organic bases is by the reduction of nitro-compounds. Many organic bodies suffer substitution of peroxide of nitrogen for hydrogen, when they are acted upon by nitric acid. The resulting nitro-compounds undergo a remarkable transformation when subjected to the influence of nascent hydrogen, sulphuretted hydrogen and other well-known reducing agents, NH, or II, taking the place of NO, or Thus benzole yields nitrobenzole (C„If,N0,) on being acted upon by nitric acid ; and nitrobenzol fur nishes the organic base phenylamine (NH,C„H,), or ANILESE, on being treated with sulphuretted hydrogen, thu.s In a similar manner there have been formed tolylamine (toluidine) (NII,C„H,) ; xylylamine (xylidine) (NH,C„II,) ; cumylamine (cumidine) (NH,C„H„); and naphtylamine, Many derivatives of these compounds have been formed by applying the substitutive pro cesses described under the first method : the following are the chief of them. Methyl.phenylamine (NIIC,H,C,,II,), a fragrant oil, boiling at Fahr. Ethyl-phenylamine (NHC,H,C,,II,), sp. gr. 0954; boiling point 400° Fahr. Met kyl-ethyl-phenylamine re sembles ethyl-phenylamine, but is not, like it, coloured blue by hypo chlorite of lime. Diethylph,enylamine (N sp. gr. 0.939; boiling point 416° Fahr. Ethyl-nitrophenylamine contains (NHC,H, [C,,H,N0,]). Amyl-pkenylamine C„Fl,) is soluble in ether and boils at 496°.4 Fahr. Methyl-amyl-phenylamine (N0,11, C,„H„ has an agreeable odour. Ethyl-amyl-phenylamine C„H,) boils at 503'4 Fahr. Diwnyl-phenylamine (N (C,,,H„),C,,H,) boils between 527° and 536° Fahr. Cetyl-phenyla mine (NHC„H„ C„H,) crystallises in plates, is not soluble in water, and melts at 107'6 Fehr. Dicelyl-phenylamine (N is more fusible than cetylphenylamine. Triethyl-phenyl-ammonium, hyd. ox. (N (C,H,),C„H, 0110) forms crystalline salts. Methyl-ethyl-amyl phenyl-ammonium hyd. ox. (N C,H, 0,11, OHO) much resembles the preceding organic base. Ethyl-tolylamine (NH 0,H„ C„H,) is a colourless MI, sp. gr. 0.939, boiling point 422°.6 Fahr. Diethyl-tolylamine boils at 444° Fahr. Triethyltolyl ammonium, hyd. ox. contains (N(C,H,), 0110).