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Trinitroethylorthocarbonate

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Trinitroethylorthocarbonate
Names
IUPAC name 2,2,2-Trinitroethyl orthocarbonate
Preferred IUPAC name 1,1,1-Trinitro-2-ethane
Other names
  • TNEOC
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
InChI
  • InChI=1S/C9H8N12O28/c22-10(23)5(11(24)25,12(26)27)1-46-9(47-2-6(13(28)29,14(30)31)15(32)33,48-3-7(16(34)35,17(36)37)18(38)39)49-4-8(19(40)41,20(42)43)21(44)45/h1-4H2Key: JPTHXHQVODRICI-UHFFFAOYSA-N
SMILES
  • C(C((=O))((=O))(=O))OC(OCC((=O))((=O))(=O))(OCC((=O))((=O))(=O))OCC((=O))((=O))(=O)
Properties
Chemical formula C(OCH2C(NO2)3)4
Molar mass 732.219 g·mol
Appearance Colorless crystals
Melting point 161 °C (322 °F; 434 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Trinitroethylorthocarbonate also known as TNEOC is an organic compound with the chemical formula C(OCH2C(NO2)3)4. It 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.

Synthesis

Trinitroethanol reacts with carbon tetrachloride under a catalyst of FeCl3.

CCl 4 Carbon   tetrachloride + 4 HOCH 2 C ( NO 2 ) 3 Trinitroethanol → FeCl 3 TNEOC + 4 HCl {\displaystyle {\ce {{\underset {Carbon\ tetrachloride}{CCl4}}+{\underset {Trinitroethanol}{4HOCH2C(NO2)3}}->{TNEOC}+4HCl}}}

References

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


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