Trinitroethylorthoformate

Last updated
Trinitroethylorthoformate
Trinitroethylorthoformate.png
Names
Preferred IUPAC name
2-[Bis(2,2,2-trinitroethoxy)methoxy]-1,1,1-trinitroethane
Other names
  • TNEOF
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C7H7N9O21/c17-8(18)5(9(19)20,10(21)22)1-35-4(36-2-6(11(23)24,12(25)26)13(27)28)37-3-7(14(29)30,15(31)32)16(33)34/h4H,1-3H2
    Key: NWWHXKXUBVOXEX-UHFFFAOYSA-N
  • C(C([N+](=O)[O-])([N+](=O)[O-])[N+](=O)[O-])OC(OCC([N+](=O)[O-])([N+](=O)[O-])[N+](=O)[O-])OCC([N+](=O)[O-])([N+](=O)[O-])[N+](=O)[O-]
Properties
C7H7N9O21
Molar mass 553.174
AppearanceColorless crystals
Melting point 128 °C (262 °F; 401 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Trinitroethylorthoformate also known as TNEOF is an explosive with excellent chemical stability. It does not have hygroscopicity, does not dissolve in water, and does not react with acids. It decomposes in aqueous sodium hydroxide solution to release formaldehyde odor. The explosion point of TNEOF is 229 °C, though it begins to decompose at 190 °C. Its explosion heat is 6.3076 J/g and specific volume is 682 L/kg. [1] Its structure is closely related to that of trinitroethylorthocarbonate (TNEOC). Both are highly explosive and very shock-sensitive, and may be dissolved in nitroalkanes to reduce their shock-sensitivity. [1]

Synthesis

Trinitroethanol is reacted with chloroform under a catalyst of FeCl3.

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2
H
4
O
. It is a cyclic ether and the simplest epoxide: a three-membered ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless and flammable gas with a faintly sweet odor. Because it is a strained ring, ethylene oxide easily participates in a number of addition reactions that result in ring-opening. Ethylene oxide is isomeric with acetaldehyde and with vinyl alcohol. Ethylene oxide is industrially produced by oxidation of ethylene in the presence of silver catalyst.

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4
F
or FOClO
3
. It is an extremely unstable gas that explodes spontaneously and has a penetrating odor.

Trinitroethylorthocarbonate Chemical compound

Trinitroethylorthocarbonate also known as TNEOC is an oxidizer with excellent chemical stability. Its explosion point is 238 °C, and it begins to be decomposed at 200 °C. Its explosion heat is 5.797 J/g and specific volume is 694 L/kg. Its structure is closely related to that of trinitroethylorthoformate (TNEOF). Both are highly explosive and very shock-sensitive, and may be dissolved in nitroalkanes to reduce their shock-sensitivity.

References

  1. 1 2 Liu, Jiping (2015). Liquid Explosives. Springer. pp. 5, 6, 8, 136, 309. ISBN   9783662458471 . Retrieved 26 March 2016.