The subject was investigated by Dakin and Dunham,[7] who first tried
chloramine-T (sodium toluene-_p_-sulphochloramide). It was found that
heavily contaminated waters, and particularly those containing much
carbonates, required a comparatively high concentration of the
disinfectant: 40 parts per million of chloramine-T were necessary in
some cases and such an amount was distinctly unpalatable. By adding
tartaric acid or citric acid the effective concentration could be
reduced to 4 p.p.m. but the mixture could not be made into a tablet
without decomposition and a two-tablet system was deemed undesirable.
Toluene sulphodichloramines were next tried. Excellent bacteriological
results were obtained but the manufacture of tablets again presented
difficulties. When the necessary quantity of dichloramine was mixed with
what were assumed to be inert salts--sodium chloride for example--the
normal slow rate of decomposition was accelerated. The dichloramine, in
tablet form, was also found to be too insoluble to effect prompt
sterilisation.
The most suitable substance found by Dakin and Dunham was "halazone" or
_p_-sulphodichloraminobenzoic acid (Cl_{2}N·O_{2}S·C_{6}H_{4}·COOH).
This compound is easily prepared from cheap readily available materials
and was found to be effective and reasonably stable.
The starting point in the preparation of halazone is
_p_-toluenesulphonic chloride, a cheap waste product in the manufacture
of saccharine. By the action of ammonia, _p_-toluene sulphonamide is
produced and is subsequently oxidised by bichromate and sulphuric acid
to _p_-sulphonamidobenzoic acid. This acid, on chlorination at low
temperatures, yields _p_-sulphondichloraminobenzoic acid (halazone). The
reactions may be expressed as follows:
CH_{3} COOH COOH
/ \ / \ / \
| | --> | | --> | |
\ / \ / \ /
SO_{2}·NH_{3} SO_{2}·NH_{2} SO_{2}·NCl_{2}
Halazone is a white crystalline solid, sparingly soluble in water and
chloroform, and insoluble in petroleum. It readily dissolves in glacial
acetic acid from which it crystallizes in prisms (M.P. 213° C.).
The purity of the compound can be ascertained by dissolving in glacial
acetic acid, adding potassium iodide, and titrating with thiosulphate;
0.1 gram should require 14.8 to 14.9 c.cms. of N/10 sodium thiosulphate.
Each chlorine atom in halazone is equivalent to 1 molecule of
hypochlorous acid and the "available" chlorine content is consequently
52.5 per cent or double the actual chlorine content.
>SO_{2}·NCl_{2} + 4HI = >SO_{2}·NH_{2} + 2HCl + 2I_{2}.
From the bacteriological results given by Dakin and Dunham it would
appear that 3 parts per million of halazone (1.5 p.p.m. available
chlorine) are sufficient to sterilise heavily polluted waters in thirty
minutes and that this concentration can be relied upon to remove
pathogenic organisms.
Public-domain text, read in full here on John Shaqi.
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