Cyanuric triazide (C₃N₁₂ or (NCN₃)₃) is described as an environmentally friendly, low toxicity, and organic

primary explosive An explosive (or explosive material) is a reactive substance that contains a great amount of potential energy that can produce an explosion if released suddenly, usually accompanied by the production of light, heat, sound, and pressure. An ...

with a

detonation velocity Explosive velocity, also known as detonation velocity or velocity of detonation (VoD), is the velocity at which the shock wave front travels through a detonated explosive. Explosive velocities are always faster than the local speed of sound in t ...

of about 7,300 m s⁻¹, and ignition temperature at 205 °C. Primary research on this compound focuses on its use as a high energy density compound.

Structure

The cyanuric triazide molecule is planar and has three-fold axis symmetry – a triskelion with

molecular point group Molecular symmetry in chemistry describes the symmetry present in molecules and the classification of these molecules according to their symmetry. Molecular symmetry is a fundamental concept in chemistry, as it can be used to predict or explain m ...

''C''_3h. The 1,3,5-triazine (or cyanuric) ring consists of alternating carbon and nitrogen atoms with C–N bond lengths of 1.334 to 1.336 Å. The distance from the center of the ring to each ring carbon atom is 1.286 Å, while the corresponding distance to ring nitrogens is 1.379 Å. Azide groups are linked to the carbon atoms on the cyanuric ring by single bonds with an interatomic distance of 1.399 Å.

Occurrence

This compound is purely synthetic and therefore does not exist in nature.

Synthesis

Cyanuric triazide can be synthesized via nucleophilic aromatic substitution using cyanuric trichloride with an excess of sodium azide refluxed in

acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscib ...

solution. The white crystals can then be purified via crystallization in −20 °C

toluene Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon. It is a colorless, water-insoluble liquid with the smell associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) a ...

Decomposition reactions

This white polycrystalline solid was found to be stable under standard conditions but is extremely shock sensitive causing it to violently decompose when ground with a mortar. The thermodynamic properties of cyanuric triazide were studied using bomb calorimetry with a combustion enthalpy (H) of 2234 kJ mol⁻¹ under oxidizing conditions and 740 kJ mol⁻¹ otherwise. The former value is comparable to the military explosive RDX, (C₃N₃)(NO₃)₃H₆, but is not put into use due to its less than favorable stability. Melting point examination showed a sharp melting range to clear liquid at 94–95 °C, gas evolution at 155 °C, orange to brown solution discoloration at 170 °C, orange-brown solidification at 200 °C and rapid decomposition at 240 °C. The rapid decomposition at 240 °C results from the formation of elemental carbon as

graphite Graphite () is a crystalline form of the element carbon. It consists of stacked layers of graphene. Graphite occurs naturally and is the most stable form of carbon under standard conditions. Synthetic and natural graphite are consumed on lar ...

and the formation of

nitrogen Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at se ...

gas.

References

{{reflist Explosive chemicals Triazines Organoazides