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Synthesis of ethanolamine dinitrate

Ethanolamine dinitrate is a powerful high explosive first prepared in 1929 by the Germans. While ethanolamine dinitrate is a powerful explosive it is also somewhat unstable, acidic, and hygroscopic; three properties that are undesirable in explosives. Nevertheless ethanolamine dinitrate has been used in explosive compositions along with other high explosives. More recently ethanolamine dinitrate has been used as an ingredient of liquid monopropellants used in rockets that are safe, inert, and nontoxic.


CxHyOz
b.p. def. 192 °C mass 169.1 g/mol
m.p. 103 °C CAS# 4665-58-1
den. 1.53 g/mL v.det. ? m/s

aminoethanol dinitrate
2-aminoethanol nitrate (ester), nitrate (salt)
2-aminoethanol nitrate nitrate
dinitrate d’ ´ethanolamine
ethanol, 2-amino-, nitrate (ester), mononitrate (salt) (9CI)
ethanol, 2-amino-, nitrate (ester), nitrate (8CI)
ethanol, 2-amino-, 1-nitrate, nitrate (1:1)
ethanol, 2-amino-, nitrate, nitrate (6CI)
Fourneau 2054
monoethanolamindinitrat
2-nitratoethylamine nitrate
2-nitratoethylammonium nitrate
O-nitromonoethanolamine nitrate salt
[2-(nitrooxy)ethyl]ammonium nitrate
nitroxyaminoethane nitrate
nitroxyethanolamine nitrate
β-nitroxyethylamine
2-nitroxyethylamine nitrate
2-nitroxyethylamine nitric acid salt
nitroxyethylammonium nitrate


ethanolamine dinitrate

ethanolamine dinitrate

Into a 1000-mL beaker place 300 mL of concentrated nitric acid (95-98%) and cool the acid to 0 C by immersing the beaker in a salt-ice bath.  Slowly add, with stirring, 100 g of MEAN while maintaining the temperature between 0 and 10 C.  After 15 minutes of stirring the reaction should be complete.  Pour 400 mL of ethyl ether into the beaker to precipitate the product.  Decant off as much of the acid ether mixture as possible before dumping the precipitate on a filter to collect it.  Wash the crystals of ethanolamine dinitrate with ice cold ethyl alcohol.  Final yield is around 97%.  Store the crystals in a desiccator as they will absorb moisture from the air.  The ether and nitric acid can be recovered and reused by distilling under vacuum.

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