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 exp ...

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 higher than the local speed of sound in t ...

of about 7,300 m s⁻¹ and a

autoignition temperature The autoignition temperature or self-ignition temperature, often called spontaneous ignition temperature or minimum ignition temperature (or shortly ignition temperature) and formerly also known as kindling point, of a substance is the lowest tem ...

of 205 °C.

Structure

The cyanuric triazide molecule exists as a planar

triskelion A triskelion or triskeles is an ancient motif consisting either of a triple spiral exhibiting rotational symmetry or of other patterns in triplicate that emanate from a common center. The spiral design can be based on interlocking Archimedean s ...

with

molecular point group In chemistry, molecular symmetry 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 explai ...

''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.

Synthesis

Cyanuric triazide can be synthesized via the

nucleophilic aromatic substitution A nucleophilic aromatic substitution (SNAr) is a substitution reaction in organic chemistry in which the nucleophile displaces a good leaving group, such as a halide, on an aromatic ring. Aromatic rings are usually nucleophilic, but some aromatic c ...

of cyanuric trichloride with an excess of

sodium azide Sodium azide is an inorganic compound with the formula . This colorless salt is the gas-forming component in some car airbag systems. It is used for the preparation of other azide compounds. It is highly soluble in water and is acutely poisonou ...

in heated

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

. The white crystals can then be purified via recrystallization from −20 °C

toluene Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon with the chemical formula , often abbreviated as , where Ph stands for the phenyl group. It is a colorless, water Water is an inorganic compound with the c ...

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 RDX (Research Department Explosive or Royal Demolition Explosive) or hexogen, among other names, is an organic compound with the formula (CH2N2O2)3. It is white, odorless, and tasteless, widely used as an explosive. Chemically, it is classified ...

, (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 Crystallinity, crystalline allotrope (form) of the element carbon. It consists of many stacked Layered materials, layers of graphene, typically in excess of hundreds of layers. Graphite occurs naturally and is the most stable ...

and the formation of

nitrogen Nitrogen is a chemical element; it has Symbol (chemistry), symbol N and atomic number 7. Nitrogen is a Nonmetal (chemistry), nonmetal and the lightest member of pnictogen, group 15 of the periodic table, often called the Pnictogen, pnictogens. ...

gas.

References

{{reflist Explosive chemicals Triazines Trimers (chemistry) Organoazides