1,2,4-Butanetriol trinitrate

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1,2,4-Butanetriol trinitrate
Names
IUPAC name
1,2,4-Butanetriol trinitrate
Other names
1,4-Dinitrooxybutan-2-yl nitrate
BTTN
Properties
C4H7N3O9
Molar mass 241.11 g/mol
Appearance Yellow clear liquid
Density 1.52 g/cm3 (at 25 °C)[1]
Melting point −27 °C (−17 °F; 246 K)
Boiling point 230 °C (446 °F; 503 K) (explosion temperature)
0.08 g/100 ml (at 20 °C)
0.15 g/100 ml (at 60 °C)
Solubility Soluble in acetone, diethyl ether, ethanol, methanol, methyl ethyl ketone
Hazards
Safety data sheet Cerilliant (as solution in MeCN)
Related compounds
Related compounds
Nitroglycerin
Erythritol tetranitrate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

1,2,4-Butanetriol trinitrate (1,2,4-BTTN), also called butanetriol trinitrate (BTTN), is an important military propellant, with better stability than nitroglycerin. It has the chemical formula C4H7N3O9.

While the isomer 1,2,3-butanetriol trinitrate is also known, the name butanetriol trinitrate is mostly used for the 1,2,4 isomer, as it's better studied.

Properties

Chemical

Butanetriol trinitrate explodes when subjected to high shock or strong heating.

Physical

1,2,4-Butanetriol trinitrate is a clear yellowish liquid explosive. It is poorly soluble in water (0.08 g/100 ml), but more soluble in acetone, diethyl ether, ethanol, methyl ethyl ketone.[2]

Explosive

1,2,4-Butanetriol trinitrate is less sensitive to shock and heat than nitroglycerin. It has an oxygen balance of -16.6%.

Availability

1,2,4-Butanetriol trinitrate is not sold by almost any entity and has to be made.

Preparation

1,2,4-Butanetriol trinitrate can be made by carefully nitrating 1,2,4-butanetriol.

Projects

  • Rocket propellent
  • Plasticizer in nitrocellulose based propellants

Handling

Safety

1,2,4-Butanetriol trinitrate is a dangerously and extremely powerful explosive. While less sensitive to mechanical forces than nitroglycerin, it can still be set off by a strong shock. Like all nitrate esters, it's a strong vasodilator, and exposure results in severe headaches. It's been shown that it's somewhat more toxic than nitroglycerin.

Storage

1,2,4-Butanetriol trinitrate should not be stored for long periods of time and used as soon as possible.

Disposal

Safe detonation in a remote area is possible, though a safer method involves strong dilution in an organic solvent followed by controlled incineration, small amounts at a time.

References

  1. http://www.dtic.mil/dtic/tr/fulltext/u2/a130875.pdf
  2. Jiping Liu (2015), Liquid Explosives, Springer, p. 261

Relevant Sciencemadness threads