It was finally transferred by suction or by pressure into tank-wagons.
At first lead-lined tanks were used, but later it was found that tanks
made of iron could be substituted. In order to take care of the small
amount of hydrobromic acid, which is slowly formed, a small amount of
magnesium oxide was added to the material. The amount of the oxide used
was approximately in the proportion of 1 part to 1000 parts of ketone.
When the magnesium oxide was used, it was found that the bromoketone
kept without appreciable decomposition for about 2 months. The yield of
the product from 580 kg. of acetone (10 kg.-mol. wts.) was 1,100 kg.
The yield from 720 kg. of methylethyl ketone (10 kg.-mol. wts.) was
1,250 kg.
HALOGENATED ESTERS
The use of ethyl iodoacetate was advocated at a time when the price of
bromine seemed prohibitive. Because of the relative price of bromine
and iodine under ordinary conditions, it is not likely that it would
be commonly used. However, it is an efficient lachrymator and is more
stable than the halogenated ketones, so that on a smaller scale it
might be advisable to use it.
It is prepared by the reaction of sodium iodide upon an alcoholic
solution of ethyl chloroacetate. It is a colorless oil, boiling at
178-180° C. (69° C. at 12 mm.) and having a density of about 1.8. It is
very much less volatile than bromoacetone, having a vapor pressure of
0.54 mm. of mercury at 20° C. Ethyl iodoacetate is about one-third as
toxic as bromoacetone, but has about the same lachrymatory value.
AROMATIC HALIDES
“Benzyl bromide” was also used during the early part of the war,
usually mixed with bromoacetone. The material was not pure benzyl
bromide, but the reaction product of bromine upon xylene, and should
perhaps be referred to as “xylyl bromide.”
Pure benzyl bromide is a colorless liquid, boiling at 198-199° C., and
having an odor reminiscent of water cress and then of mustard oil.
The war gas is probably a mixture of mono- and dibromo derivatives,
boiling at 210-220° C., and having a density at 20° C. of 1.3. The
mixture of benzyl and xylyl bromides used by the Germans was known as
“T-Stoff,” while the mixture of 88 per cent xylyl bromide and 12 per
cent bromoacetone was called “Green T-Stoff.”
As in the case of the halogenated acetones, it is necessary to use lead
lined shell for these compounds. Enamel and glass lined shell may be
used and give good results. While they are difficult of manufacture,
satisfactory methods were being developed at the close of the war.
“T-Stoff” may be detected by the nose in concentrations of one part in
one hundred million of air, and will cause profuse lachrymation with
one part in a million. It is a highly persistent material and may last,
under favorable circumstances, for several days. While it is relatively
non-toxic, French troops were rendered unconscious by it during certain
bombardments in the Argonne in the summer of 1915.
Public-domain text, read in full here on John Shaqi.
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