Styphnic acid

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Styphnic acid
Names
IUPAC name
2,4,6-Trinitrobenzene-1,3-diol
Other names
2,4-Dihydroxy-1,3,5-trinitrobenzene
2,4,6-Trinitro-1,3-benzenediol
2,4,6-Trinitroresorcinol
Properties
C6H3N3O8
Molar mass 245.11 g/mol
Appearance Yellow solid
Odor Odorless
Density 1.829 g/cm3 (20 °C)
Melting point 180 °C (356 °F; 453 K)
Boiling point Decomposes
0.54 g/100 ml (25 °C)
1.15 g/100 ml (62 °C)
3.326 g/100 ml (96 °C)[1]
Solubility Reacts with bases
Soluble in nitric acid[2]
Solubility in 1,2-Diacetoxy ethane 13 g/100 ml (20 °C)[3]
Solubility in acetone 31.3 g/100 ml (17 °C)
Solubility in benzene 47 g/100 ml (68 °C)
86 g/100 ml (80 °C)[4]
Solubility in carbon tetrachloride 0.5 g/100 ml[5]
Solubility in ethanol 5.1 g/100 ml (0 °C)
6.22 g/100 ml (17 °C)
14.65 g/100 ml (68 °C)[6]
Thermochemistry
-467.5 kJ/mol
Hazards
Safety data sheet None
Related compounds
Related compounds
Picric acid
Lead styphnate
Trinitrophloroglucinol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Styphnic acid or 2,4,6-trinitro-1,3-benzenediol (C6H3N3O8), is a yellow astringent acid (from Greek stryphnos "astringent") that forms hexagonal crystals.

Properties

Chemical

Like picric acid, it is a moderately strong acid, capable of displacing carbon dioxide from solutions of sodium carbonate, for example.

It can also react with weakly basic oxides, such as those of lead and silver, to form the corresponding salts.

Physical

Trinitroresorcinol is a yellowish, crystalline solid, insoluble in water but more soluble in organic solvents.

Explosive

Styphnic acid is itself a low sensitivity explosive, similar to picric acid, but explodes upon rapid heating.

Availability

Styphnic acid is not sold by suppliers and has to be made.

Preparation

It may be prepared by the nitration of resorcinol with a mixture of conc. nitric and sulfuric acid.[7]

Projects

Handling

Safety

Styphnic acid is explosive and may explode if ignited. Like all nitroaromatics, it is toxic and will absorb through skin, staining it yellow.

Storage

Do not store it for long.

Disposal

Unlike other aromatic energetic compounds, styphnic acid cannot be safely burned as it may explode.

To safely neutralize it, it must first be diluted then chemically neutralized to less harmful products. One patent indicates that bubbling chlorine in an acidified dil. solution containing styphnic acid will destroy the compound.[8]

References

  1. Yalkowsky S.H., Yan H. Handbook of aqueous solubility data. - CRC Press, 2003
  2. https://link.springer.com/chapter/10.1007%2F978-1-4899-0330-3_28
  3. Taylor; Rinkenbach; Journal of the American Chemical Society; vol. 48; (1926); p. 1309
  4. Орлова Е.Ю. Химия и технология бризантных взрывчатых веществ. - М., 1960 pp. 205
  5. Srinivasan; Mitra; Science and Culture; vol. 12; (1947); p. 502
  6. Орлова Е.Ю. Химия и технология бризантных взрывчатых веществ. - М., 1960 pp. 205
  7. http://www.powerlabs.org/chemlabs/styphnic.htm
  8. http://www.freepatentsonline.com/2487627.html

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