Trinitroethylorthocarbonate

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| Name = Trinitroethylorthocarbonate

| IUPACName = 2,2,2-Trinitroethyl orthocarbonate

| PIN = 1,1,1-Trinitro-2-[tris(2,2,2-trinitroethoxy)methoxy]ethane

| OtherNames = {{Unbulleted list | TNEOC }}

| ImageFile = Trinitroethylorthocarbonate.png

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| CASNo = 14548-58-4

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| PubChem = 139779

| ChemSpiderID = 123272

| 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-]

| StdInChI = 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

| StdInChIKey = JPTHXHQVODRICI-UHFFFAOYSA-N

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| Appearance = Colorless crystals

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| Formula = {{chem2|C(OCH2C(NO2)3)4}}

| C=9|H=8|N=12|O=28

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| MeltingPtC = 161

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Trinitroethylorthocarbonate, also known as TNEOC, is an organic compound with the chemical formula {{chem2|C(OCH2C(NO2)3)4}}. It is an oxidizer with excellent chemical stability.{{Citation needed|reason=exellent chemical stability is a subjective term and any statement of stability needs to have contextual information given the statement later in the page about the highly explosive nature of this compound|date=May 2017}} 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.{{cite book|last1=Liu|first1=Jiping|title=Liquid Explosives|date=2015|publisher=Springer|isbn=9783662458471|pages=5, 6, 8, 136, 309|url=https://books.google.com/books?id=NGYiBgAAQBAJ&pg=PA8|accessdate=26 March 2016}} 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

TNEOC can be prepared by the reaction of trinitroethanol with carbon tetrachloride, catalyzed by FeCl3:{{cite journal | doi = 10.1070/mc2005v015n05abeh002157 | title = Synthesis of 2-R-2,2-dinitroethanol orthoesters in ionic liquids | date = 2005 | last1 = Sheremetev | first1 = Aleksei B. | last2 = Yudin | first2 = Igor L. | journal = Mendeleev Communications | volume = 15 | issue = 5 | pages = 204–205 }}

:{{chem2 | 4 HOCH2C(NO2)3 + CCl4 -> TNEOC + 4 HCl }}

References