The Chemistry of Powder and Explosives - Sciencemadness Dot Org

156 AROMATIC NITRO COMPOUNDS
trinitronaphthalene (glistening plates, m.p. 147°), and 5- or
1,2,5-trinitronaphthalene (m.p. 112-113°). The nitration of /3-dinitronaphthalene
yields /3- or 1,3,8-trinitronaphthalene (monoclinic
crystals, m.p. 218°), and the same substance, along with some
a-trinitronaphthalene, is formed by the nitration of y-dinitronaphthalene.
-NO,
NO2 NOa
-NO2
NO2
I
NO2
I
-NO2
NO,
NO2 NO2 NO2
s-
All these isomers occur in commercial trinitronaphthalene, known
as naphtite, which melts at about 110°.
The nitration of a-, /?-, and y-trinitronaphthalene yields y- or
1,3,5,8-tetranitronaphthalene (glistening tetrahedrons, m.p. 194-
195°). The nitration of the /3-compound also yields /?- or 1,3,6,8tetranitronaphthalene
(m.p. 203°), and that of the 5-trinitro
compound yields 5- or 1,2,5,8-tetranitronaphthalene (glistening
prisms which decompose at 270° without melting), a substance
which may be formed also by the introduction of a fourth nitro
group into y-trinitronaphthalene. The nitration of 1,5-dinitronaphthalene
45 yields a-tetranitronaphthalene (rhombic crystals,
m.p. 259°) (perhaps 1,3,5,7-tetranitronaphthalene), and this substance
is also present in the crude product of the tetranitration,
which, however, consists largely of the /?-, y-, and 5-isomers,
N<
NO* NO,
I I
-NO2
NO2 NO2
I I
NO2
7-
-NO2
NOj KO2
I
The crude product is impure and irregular in its appearance; it is
commonly purified by recrystallization from glacial acetic acid
45 Aguiar, Ber., 5, 374 (1872).