The Chemistry of Powder and Explosives - Sciencemadness Dot Org

PENTRYL 229
Another portion of the free nitrate radical apparently reacts with
itself and with water as indicated below, and the oxygen which
becomes available enters into the reaction with the consequent
formation of dinitrodiglycol.
2NO3 > N2O6 + [01
CH2-ONO2
N2O6 + H20 > 2HNO3 I
c :H2
CH2
\
" + [01 + 2NO3 > 0
CH/
0N02
A platinum gauze anode is used. It is immersed in an acetone
solution of calcium nitrate which is kept continuously saturated
with ethylene which is bubbled through in such manner that it
sweeps over the surface of the platinum gauze. An aluminum
cathode is used, in a catholyte consisting of a nitric acid solution
of calcium nitrate, and the cathode compartment is filled to a
higher level since the liquid moves into the anode compartment
as the electrolysis progresses. After the electrolysis, the cathode
liquid is fortified with nitric acid for use again. The anode liquid
is neutralized with slaked lime, and distilled in vacuum for the
recovery of the acetone, and the residue, after the removal of
calcium nitrate, washing, and drying, consists of a mixture of
nitroglycol and dinitrodiglycol and is known as Oxinite. Dynamites
made from Oxinite differ but little from those made from
nitroglycerin.
Pentryl
Pentryl, or 2,4,6-trinitrophenylnitraminoethyl nitrate, is another
explosive which is derived from ethylene. It is a nitric ester,
an aromatic nitro compound, and a nitroamine. The substance
was described in 1925 by Moran 54 who prepared it by the action
of mixed acid on 2,4-dinitrophenylethanolamine (large orangeyellow
crystals from alcohol, m.p. 92°) procured by the interaction
of dinitrochlorobenzene with ethanolamine. von Herz later
prepared pentryl by the nitration of /3-hydroxyethylaniline, a
material which is more commonly called phenylethanolamine and
is now available commercially in this country, and was granted
5 *U. S. Pat. 1,560,427 (1925).