One of the earliest lachrymators used was bromoacetone. Because of
the difficulty of obtaining pure material, the commercial product,
containing considerable dibromoacetone and probably higher halogenated
bodies, was used. The presence of these higher bromine derivatives
considerably decreased its efficiency as a lachrymator. The preparation
of bromoacetone involved the loss of considerable bromine in the form
of hydrobromic acid. This led the French to study various methods of
preparation, and they finally obtained a product containing 80 per
cent bromoacetone and 20 per cent chloroacetone, which they called
“martonite.” As the war progressed, acetone became scarce, and the
Germans substituted methylethylketone, for which there was little use
in other war activities. This led to the French “homomartonite.”
Various other halogen derivatives of ketones have been studied in the
laboratory, but none have proven of as great value as bromoacetone,
either from the standpoint of toxicity or lachrymatory power.
_Bromoacetone_ may be prepared by the action of bromine (liquid or
vapor) upon acetone (with or without a solvent). Aqueous solutions of
acetone, or potassium bromide solutions of bromine, have also been used.
Pure bromoacetone is a water clear liquid. There are great differences
in the properties ascribed to this body by different investigators.
This probably is due to the fact that the monobromo derivative is mixed
with those containing two or more atoms of bromine. A sample boiling at
126-127° and melting at -54°, had a specific gravity of 1.631 at 0°. It
has a vapor pressure of 9 mm. of mercury at 20°.
While bromoacetone is a good lachrymator, it possesses the disadvantage
that it is not very stable. Special shell linings are necessary, and
even then the material may be decomposed before the shell is fired.
The Germans used a lead-lined shell, while considerable work has been
carried out in this country with enamel lined shell. Glass lined shell
may also be used. It is interesting to note that, while bromoacetone
decomposes upon standing in the shell, it is stable upon detonation.
No decomposition products are found after the explosion, and even
unchanged liquid is found in the shell. It may be considered as having
a low persistency, since the odor entirely disappears from the surface
of the ground in twenty-four hours.
Bromoacetone was also used by the Germans in glass hand grenades
(Hand-a-Stink Kugel) and later in metal grenades. The metal grenades
weighed about two pounds and contained about a pound and a half of the
liquid.
_Martonite_ was prepared by the French in an attempt more completely
to utilize the bromine in the preparation of bromoacetone. They
regenerated the bromine by the use of sodium chlorate:
NaClO₃ + 6HBr = NaCl + 3Br₂ + 3H₂O
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