232 Royal Society :— 
Nov. 17, 1859.—Sir Benjamin C. Brodie, Bart., Pres., in the Chair. 
. The following communication was read :— 
« Notes of Researches on the Poly-Ammonias.”—No. VI. New 
Derivatives of Phenylamine and Ethylamine. By A. W. Hofmann, 
LL.D., F.R.S. &c. 
Some time ago* I communicated to the Royal Society some re- 
sults obtained in studying the action of dibromide of ethylene upon 
phenylamine. The principal product of this reaction was found to 
be a well-defined crystalline compound with basic characters. By 
the analysis of the base itself, and of several of its combinations, it 
had been proved that the formula 
0,1, N= GH)" 1 x 
10) Oo C,, H, 
is the simplest atomic expression for the new substance ; but the 
action of iodide of methyle and of ethyle upon this body having given 
rise to compounds i 
—=— 18 i, N \ 
C,, H,, N, Cs H, N C, H, I 
ais C,, H, N 
= ~16 79 1H L 
CH, NI= 6" HN | CoH 
I was induced to assume the formula 
C H " 
C,, H,, N=. Ht), \ N, 
as representing the true constitution of the basic body, which thus 
appears as a diammonia, in which 2 equivs. of hydrogen are replaced 
by 2 equivs. of phenyle, and 4 equivs. of hydrogen by 2 molecules of 
diatomic ethylene. 
This view involves the existence of a basic compound, 
(C, H,)" 
C,, H,, N,= (CF H,), N,, 
H, 
i.e. of a diphenyl-diamine in which only one molecule of diatomic 
ethylene has been substituted for hydrogen. 
Experiment has not failed to realize the body pointed out by 
theory. A mixture of dibromide of ethylene with a large excess of 
phenylamine (1 vol. of dibromide of ethylene and 4 vols. of phenyl- 
amine) rapidly solidifies to a crystalline mass. Treatment with 
water removes from this mixture a very considerable proportion of 
hydrochlorate of phenylamine, leaving a brown resinous substance, 
which gradually but imperfectly solidifies. This substance forms a 
hydrochlorate which is difficultly soluble in concentrated hydro- 
chloric acid, and which may be readily purified by repeated crystal- 
lizations from boiling alcohol. The “pure hydrochlorate dissolved 
in water, and mixed with potassa or ammonia, furnishes the free base, 
which generally separates as an oil, rapidly solidifying into a cry- 
* Phil. Mag, vol, xvii. p. 66. 
