1-Nitrohydantoin and Derivatives
This is really only of interest because it is a simple urea-glycine condensation product. There is no published information on its explosive
properties that I am aware of.
There is a few bits published on urea glycine condensation, US Patent 4647694 looks to be the simplest route by simply heating glycine with excess
urea then cyclising with sulphuric acid. I only found this after I'd already done everything presented here, I went with Chinese patent CN1958569A,
which uses glycine + urea + sodium hydroxide for the initial condensation, followed by sulphuric acid in a 1 pot reaction over 12 hours. This goes
well, my yield was 53%, down from the 73% claim but I was quite aggressive with the washing.
I did initially try Chem. Heterocycl. Compd. 14, 70–72 (1978). which gives straight heating urea and glycine in sulphuric acid (1:1:0.5eq) but I
didn't get crystallisation. And British patent GB991644 by directly fusing solid urea with glycine, this is gross and ugly forget his route.
Theres little information on nitrohydantoin itself other than GB991644, where it's used as an intermediate to 1-aminohydantoin. Its nitration uses
fuming HNO3 + P2O5, add hydantoin at 10C then stir as it returns to room temperature over the next 4 hours then dump in ice water and filter. This
works fine, I got 66% yield. m.p. crudely measured on hotplate coinciding with the 173C from the patent.
I also tried sulphuric acid + KNO3 nitration, 40g KNO3 + 65mL H2SO4, cooled to 10C and 11g hydantoin added. This gets really thick by the end and had
to be raised to 16C for stirring. It was left 30min after last addition then dunked for 22% yield with the same melting point.
It dissolved readily in acetone but I couldn't get it to precipitate on addition of water.
These nitrations are very smooth, no noticeable exotherm and hydantoin readily dissolves. The low yield from KNO3/H2SO4 may well be because it was run
too cool and too short, I'd forget i'd left the HNO3/P2O5 for 4 hours and dunked the KNO3/H2SO4 too early.
It does not seem like a dinitro derivative is possible. Dinitrodimethylhydantoin is known however uses a novel nitration process (trichloroacetic
anhydride, ammonium nitrate in nitromethane). dimethylhydantoin is available OTC as its chloro-bromo compound for pools, presumably this can be
dehalogenated via heating with NaOH.
As previously said, 1-nitrohydantoin has no published explosive properties. It's closest relative is dinitroglycoluril (DNGU), 1-nitrohydantoin in
effect being half DNGU with an extra carbonyl group. If its detonatable its likely insensitive, and relatively low powered owing to its oxygen
balance. Its saving grace may be its density, which is unknown, but has the possibility of being high (DNGU is 1.99g/cm3). On ignition it does sustain
deflagration leaving black residue.
It's acidic, I dissolved it into 1eq of sodium hydroxide and precipitated the silver salt, attempt at a lead salt failed. The silver salt deflagrated
energetically but not explosively leaving silver fluff residue.
I have not tried to detonate it.
Speculating where else it can be taken; it could probably be chlorinated resulting in the retarded child of RDX and TCCA. It can likely be hydrolysed
to nitraminoacetamide, which might condense with hydrazine followed by nitrous acid to yield nitraminoacetylazide, but I'm not even sure if that is a
known compound.
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