426 CHEMISTRY AND TECHNOLOGY OF EXPLOSIVES
Experiments on the nitration of naphthalene with nitrogen dioxide were carried
out by Leeds [22] and more recently by Topchiyev [23]. The latter, in his experiments
under various nitration conditions, obtained different products. At room temperature
FIG. 106. Pascal’s diagram of the nitration dinitronaphthalene-limits of formation:
I - TNN, II - TetraNN [20a].and with an excess of nitrogen dioxide, α− nitronaphthalene was obtained in a yield
amounting to 96%; at 60°C, 1,5-dinitronaphthalene was formed (12% yield),
along with α− nitronaphthalene (80% yield). At 150°C, in addition to these (in 30%
and 36% yields) 1,8-dinitronaphthalene and a certain amount of 1,3,8-trinitro-
naphthalene were obtained (18% and 2% yields respectively).
Lantz [23a] has studied the nitration of naphthalene sulphonic acids (mono-,
di- and tri-sulphonic acids). He stated that no displacement of the sulphonic groups
with nitro groups occurs. By using nitrating concentrated mixtures he was able
to introduce nitro groups so that the number of both SO 3 H and NO 2 groups reached
a maximum of four.MONONITRO DERIVATIVES OF NAPHTHALENE
Both the mononitro isomers, α and β, are known:
αα