I looked up the literature again today, and I’m puzzled as to why my textbook states that the reaction between sodium hypochlorite and
hexamethylenetetramine only yields DPT, in which both nitro groups are replaced by chlorine atoms. This is the same outcome as the reaction of
hexamethylenetetramine with nitrous acid: at pH ≤ 1 it forms the R salt, while between pH 3 and 6 it forms a DPT analogue (where each nitro group is
replaced by a nitroso group). Because a near-neutral environment makes further ring opening difficult, the failure to obtain RDX actually seems more
reasonable. Perhaps adding a small amount of acid would allow formation of the six-membered ring, but excessive acidity would lead to the formation of
nitrogen trichloride, which would result in immediate detonation. Therefore, this system likely needs to be handled with great caution.
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