Synthesis of ethylene glycol dinitrate

Preparation of ethylene glycol dinitrate

Alternative Names: Ethylene dinitrate; 1,2-Ethanediol, dinitrate; Dinitroglycol; Ethylene nitrate; Glycol dinitrate; Nitroglycol;

Preparation of ethylene glycol dinitrate

Preparation of ethylene glycol dinitrate

Ethylene glycol dinitrate is prepared similarly as nitroglycerin. 100 g of anhydrous glycol is slowly added to 625 g of mixed acid containing 40% nitric acid (>99% d=1.52 g/ml), 60% sulfuric acid  (>99% d=1.98 g/ml) at 10-12° C with constant stirring. When the nitration is complete the reaction mixture is poured in ice water. The oily layer is separated, washed with water, sodium carbonate and dried over calcium carbonate in a desiccator.   Yield 222 g.

Ethylene glycol dinitrate is formed in considerable quantities when a current of dry ethylene is passed through a concentrated mixture of nitric and sulfuric acids, the latter being constantly shaken or mechanically stirred.

Preparation of ethylene glycol dinitrate by nitrating ethylene

Preparation of ethylene glycol dinitrate by nitrating ethylene

A mixed acid containing about 32% nitric acid is used. The yield amounts to 350% of the gas absorbed composed of 40% nitroglycol and 60% nitroethyl nitrate, or about 70% of the theoretical yield.

Nitroglycerine and Nitroglycerine Explosives, by P Naoum, 218-222, 1928

IUPAC Name

2-nitrooxyethyl nitrate

InChI

InChI=1S/C2H4N2O6/c5-3(6)9-1-2-10-4(7)8/h1-2H2

InChI Key

UQXKXGWGFRWILX-UHFFFAOYSA-N

Canonical SMILES

C(CO[N+](=O)[O-])O[N+](=O)[O-]

MeSH Synonyms

ethylene glycol dinitrate, nitroglycol

Depositor-Supplied Synonyms

Ethylene dinitrate, 1,2-Ethanediol, dinitrate, Dinitroglycol, Ethylene nitrate, Glycol dinitrate, Nitroglycol, EGDN, Ethylene glycol, dinitrate, Ethanediol dinitrate, Dinitroglicol, Glycoldinitraat, Glykoldinitrat, Nitroglykol, ethane-1,2-diyl dinitrate, 628-96-6, Ethylenglykoldinitrat, Nitroglykol [Czech], 1,2-Ethanediol, 1,2-dinitrate, 2-nitrooxyethyl nitrate, Dinitroglicol [Italian], Glycoldinitraat [Dutch], Glykoldinitrat [German], 1,2-Ethanediol dinitrate, Ethylenglykoldinitrat [Czech], HSDB 537, Glycol (dinitrate de) [French], Dinitrato de etilenglicol [Spanish], EINECS 211-063-0, Dinitrate d’ethylene glycol [French], Ethylene glycol dinitrate [Forbidden], BRN 1709055, egnd, Dinitroglycoe, EGDe, Nitroglycol (NGce, Glycol (dinitrate de), Dinitrato de etilenglicol, 1,2-Bis(nitrooxy)ethane, 2-(nitrooxy)ethyl nitrate, UNII-9CZ6PE9E3J, Dinitrate d’ethylene glycol, AC1Q28VT, 9CZ6PE9E3J, Ex123, SCHEMBL417312, AC1L24J7, UQXKXGWGFRWILX-UHFFFAOYSA-N, ZINC5178846, AKOS006277312, AN-22049, LS-68538, OR040415, OR309940, 4-01-00-02413 (Beilstein Handbook Reference), 3B1-006826, 121749-11-9

Removed Synonyms

ETHYLENE GLYCOL DINITRATE, CID40818

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