Pentaerythritol tetranitrate

Pentaerythritol tetranitrate

Names
IUPAC name [3-Nitrooxy-2,2-bis(nitrooxymethyl)propyl] nitrate
Other names Pentaerythrityl tetranitrate Pentrite Pentrit
Identifiers
Jmol-3D images	Image
SMILES C(C(CO[N+](=O)[O-])(CO[N+](=O)[O-])CO[N+](=O)[O-])O[N+](=O)[O-]
Properties
Chemical formula	C5H8N4O12
Molar mass	316.14 g/mol
Appearance	White crystalline solid
Odor	Odorless
Density	1.77 g/cm3 (at 20 °C)
Melting point	141.3 °C (286.3 °F; 414.4 K)
Boiling point	180 °C (356 °F; 453 K) (decomp. begins > 150 °C)
Solubility in water	0.0043 mg/100 ml (at 20 °C)
Solubility	Very soluble in acetone Soluble in benzene, toluene Slightly soluble in methanol
Solubility in acetone	25.4 g/100 g (20 °C)
Solubility in ethyl acetate	10.619 g/100 g
Vapor pressure	~0 mmHg
Hazards
Safety data sheet	detotec
Lethal dose or concentration (LD, LC):
LD50 (Median dose)	25,000 mg/kg (rat, oral)
Related compounds
Related compounds	Erythritol tetranitrate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Pentaerythritol tetranitrate or PETN is an explosive material, widely used in military applications, mainly due to its good stability and general performances. It is a nitrated organic compound, with the chemical formula C₅H₈N₄O₁₂.

Properties

Chemical

PETN will burn if ignited in air, releasing carbon dioxide, water vapor and soot.

PETN does not hydrolyze in water at room temperature, though this changes at high temperatures.

Physical

PETN is a white crystalline solid, insoluble in water, but soluble in acetone and dimethylformamide (40 g/100 g at 40 °C), as well as benzene and toluene. It also shows good solubility in ethyl acetate (10.619 g/100 g EtOAc). It is also slightly soluble in alcohols, such as methanol and ethanol.

Explosive

Pentaerythritol tetranitrate is one of the most powerful explosive materials known, with a relative effectiveness (RE) factor of 1.66. Its average detonation velocity is 8400 m/s.

PETN is rarely used as a pure compound in explosive devices, instead it is mixed with various plasticizers, to form plastic explosives. When mixed with with RDX, binders (styrene-butadiene e.g.), plasticizers (such as n-octyl phthalate or tributyl citrate), antioxidants (N-phenyl-2-naphthylamine) and dyes (Sudan I or IV) it forms a very powerful plastic explosive called Semtex, widely used by various countries of the former Soviet block.

PETN is more difficult to detonate than primary explosives: dropping or igniting a block of PETN will not result in an explosion (at atmospheric pressure it is difficult to ignite and burns slow), however it is more sensitive to shock and friction than other secondary explosives such as TNT or tetryl.

Availability

PETN is sold in small amounts in pharmacies as a vasodilator, as treatment for heart conditions. The heart medicine Lentonitrat is nearly pure PETN.

Preparation

PETN can be prepared by nitrating pentaerythritol using concentrated nitric acid under controlled conditions.

Projects

• Make blasting charges
• Heart medication

Handling

Safety

PETN is a vasoldilator and ingestion should be avoided.

Storage

PETN should be stored in closed containers. Urea is sometimes added as a stabilizer.

Disposal

PETN can be safely neutralized with Fenton's reagent. Diluted solutions of PETN should be added slowly, to prevent splashing.

Powdered iron can be used as a reducing agent.

References

Relevant Sciencemadness threads

• PETN synth
• PETN?
• Question about PETN
• PETN recrystallisation procedure for LOW density
• PETN-based Cast Explosives
• initiate petn