Erythritol tetranitrate

Erythritol tetranitrate

Names
IUPAC name [(2R,3R)-1,3,4-Trinitrooxybutan-2-yl] nitrate
Systematic IUPAC name Erythritol tetranitrate
Other names Meso-1,2,3,4-tetrakis-nitrooxy-butane Erythrityl tetranitrate ETN Tetra-O-nitro-erythritol
Identifiers
Jmol-3D images	Image
SMILES C(C(C(CO[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-]
Properties
Chemical formula	C4H6N4O12
Molar mass	302.11 g/mol
Appearance	White solid
Density	1.827 g/cm3
Melting point	61 °C (142 °F; 334 K)
Boiling point	160 °C (320 °F; 433 K) (decomposes)
Solubility in water	Insoluble
Solubility	Soluble in acetone, diethyl ether, ethanol, methanol, isopropanol
Hazards
Related compounds
Related compounds	Methyl nitrate Ethylene glycol dinitrate Nitroglycerin
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Erythritol tetranitrate or ETN is an explosive compound. Unlike other explosive materials, such as TNT, PETN, ETN is much easier to manufacture and has positive oxygen balance, which gives it a better performance.

Properties

Chemical

ETN is about 3 times more sensitive than PETN and is more sensitive to friction than the former mentioned compound. The decomposition of ETN is oxygen positive:

C₄H₆N₄O₁₂ → 4 CO₂ + 3 H₂O + N₂ + 3/2 O₂

Physical

Erythritol tetranitrate is an odorless white solid compound. It is insoluble in water, but very soluble in acetone and other ketones, as well as alcohol. Its solubility in alcohol decreases as the alcohol weight increases.

Explosive

ETN has a high velocity of detonation (VOC) of 8000–8100 m/s, at a density of 1.6 g/cm³. As an explosive, ETN is somewhat sensitive to shock and friction, though less so than most common sensitive explosives.

Erythritol tetranitrate is known for having a very long shelf life, samples stored at room temperature show no signs of decomposition even after after four years.

Availability

Erythritol tetranitrate is not sold by almost any entities, even big chemical suppliers like Sigma-Aldrich don't have it in their stock.

Preparation

Erythritol tetranitrate can be prepared by nitrating erythritol using a nitrating mixture. It can be extracted from the reaction product by dissolving it in ethanol and then adding water, which causes it to precipitate.

It's recommended to obtain the final product as powder rather than large crystals, as it's less sensitive.

Projects

• Make blasting charge

Handling

Safety

Erythritol tetranitrate is sensitive to strong shock and friction, and may explode. If consumed, it results in severe headaches, due to being a strong vasodilator, property seen in other nitrated organic compounds.

Storage

ETN should be stored in closed non-metal spark free containers, preferably in special cabinets. For safety and legal reasons avoid storing large amounts. Try to use it as soon as you make it.

Disposal

ETN can be neutralized with an excess solution of sodium hydroxide, at low temperatures.

References

Relevant Sciencemadness threads

• Erythritol Tetranitrate
• erythritol tetranitrate recrystallization
• ETN synthesis problem