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Trinitroethylorthoformate

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Trinitroethylorthoformate
Names
Preferred IUPAC name 2--1,1,1-trinitroethane
Other names
  • TNEOF
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • 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,1-3H2Key: NWWHXKXUBVOXEX-UHFFFAOYSA-N
SMILES
  • C(C((=O))((=O))(=O))OC(OCC((=O))((=O))(=O))OCC((=O))((=O))(=O)
Properties
Chemical formula C7H7N9O21
Molar mass 553.174
Appearance Colorless 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 , 100 kPa). Infobox references
Chemical compound
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Find sources: "Trinitroethylorthoformate" – news · newspapers · books · scholar · JSTOR (May 2017)

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. 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.

Synthesis

Trinitroethanol is reacted with chloroform under a catalyst of FeCl3.

CHCl 3 chloroform + 3 HOCH 2 C ( NO 2 ) 3 Trinitroethanol → FeCl 3 TNEOF + 3 HCl {\displaystyle {\ce {{\overset {chloroform}{CHCl3}}+ {\overset {Trinitroethanol}{3HOCH2C(NO2)3}}-> {TNEOF}+ 3HCl}}}

References

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


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