The Chemistry of Powder and Explosives - Sciencemadness Dot Org

TRINITROPHENOXYETHYL NITRATE 227
methyl alcohol, chloroform, benzene, and glacial acetic acid. It
is immiscible, or only slightly soluble, in ethyl alcohol, carbon
tetrachloride, and carbon disulfide. It is slightly hygroscopic and
is soluble in water to the extent of about 4.1 grams per liter of
water at 24°. It can be ignited only with difficulty, and in small
quantity is not readily exploded by heat. It is less sensitive than
nitroglycol in the drop test. It is so insensitive to initiation that
it will not propagate its own detonation under conditions where
nitroglycol and nitroglyccrin will do it. In 50/50 mixture however
with either of these substances it detonates satisfactorily
"and shows an explosive effect but little less than that of either
of these compounds." It has a vapor pressure of about 0.007 mm.
of mercury at 22.4°, and produces headaches similar to those produced
by nitroglycerin.
Trinitrophenoxyethyl Nitrate
Another explosive which is preparable from glycol and which
may perhaps be of interest for special purposes in the future is
the /3-2,4,6-trinitrophenoxyethyl nitrate described by Wasmer 60
in 1938. Glycol is converted into its monosodium derivative, and
this is made to react with dinitrochlorobenzene at 130° for the
production of /3-dinitrophenoxyethyl alcohol which gives the explosive
by nitration with mixed acid.
NO,
CH2-0H CHj-O-/~~\-NO,
/CHS-OH
^CH,-ONa' CH,-O—( }— NO,
CHj-OH NO,
CH,- ONO,
Trinitrophenoxyethyl nitrate is procured as a white powder, m.p.
104.5°, insoluble in water and readily soluble in acetone. It gelatinizes
collodion nitrocotton, and is intennediatc between picric
acid and tetryl in its sensitivity to mechanical shock.
50 Mem. poudres, 28, 171 (1938).