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(Michael S) #1
OTHER NITRO DERIVATIVES OF PHENOLS^531

from diquinoyltrioxime. The latter can exist in two isomeric forms, (Ia) and (Ib),
, which may be prepared by reacting hydroxylamine with dinitrosoresorcinol:


Tetranitrophenol forms by the action of 50% nitric acid followed by a 63%
acid on diquinoyltrioxime at a temperature lower than the room temperature. By
neutralizing the solution a sparingly soluble potassium salt is precipitated, which
in turn may be converted by double decomposition into a still less soluble barium
salt. From the latter, by the action of a calculated quantity of sulphuric acid, free
tetranitrophenol may be obtained.
A product of higher purity than that obtained by Nietzki was prepared by
Blanksma [21] by the nitration of m- nitrophenol with a mixture of nitric acid (sp.
gr. 1.52) and concentrated sulphuric acid. As shown later (van Duin and van Len-
nep [22]) the product, if of high purity, exhibits fairly high stability against heating.
It explodes at 245-251°C, whereas if it is contaminated it decomposes after it has
been brought to its melting point, i.e. to 140°C.
The nitro group in position 3 in tetranitrophenol is very reactive. On boiling
with water the compound yields trinitroresorcinol. With methyl alcohol it forms
trinitroresorcinol monomethyl ether. With an alcoholic ammonia solution, tetrani-
trophenol gives aminotrinitrophenol.
Tetranitrophenol is more sensitive to impact than tetryl (van Duin and van
Lennep [22]).

PENTANITROPHENOL
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