Trinitroethylorthocarbonate

Trinitroethylorthocarbonate
Names
	IUPAC name 2,2,2-Trinitroethyl orthocarbonate
	Preferred IUPAC name 1,1,1-Trinitro-2-[tris(2,2,2-trinitroethoxy)methoxy]ethane
	Other names TNEOC;
Identifiers
CAS Number	14548-58-4;
3D model (JSmol)	Interactive image;
ChemSpider	123272;
PubChem CID	139779;
	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/h1-4H2 Key: JPTHXHQVODRICI-UHFFFAOYSA-N;
	SMILES 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-])OCC([N+](=O)[O-])([N+](=O)[O-])[N+](=O)[O-];
Properties
Chemical formula	C(OCH2C(NO2)3)4
Molar mass	732.219 g·mol−1
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 [77 °F], 100 kPa). Infobox references

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.^[1] 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.^[1]

Synthesis

TNEOC can be prepared by the reaction of trinitroethanol with carbon tetrachloride, catalyzed by FeCl₃:^[2]

4 HOCH₂C(NO₂)₃ + CCl₄ → TNEOC + 4 HCl

References

^ ^a ^b Liu, Jiping (2015). Liquid Explosives. Springer. pp. 5, 6, 8, 136, 309. ISBN 9783662458471. Retrieved 26 March 2016.
^ Sheremetev, Aleksei B.; Yudin, Igor L. (2005). "Synthesis of 2-R-2,2-dinitroethanol orthoesters in ionic liquids". Mendeleev Communications. 15 (5): 204–205. doi:10.1070/mc2005v015n05abeh002157.

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

[2] Sheremetev, Aleksei B.; Yudin, Igor L. (2005). "Synthesis of 2-R-2,2-dinitroethanol orthoesters in ionic liquids". Mendeleev Communications. 15 (5): 204–205. doi:10.1070/mc2005v015n05abeh002157.

[1]

[2]