Nitric Acid → 1,2-Ethanediamine, nitrate (1:2)

Participants

Reaction Steps

To a 3-liter, jacketed, round bottom flask with a bottom outlet and fitted with an addition funnel, stirrer, and thermometer were charged 790 grams of water and 339 grams of ethylenediamine. To this stirred solution was added, via the addition funnel, 1,006 grams of 70 weight percent HNO3. The temperature was maintained between 20° C. and 30° C. by circulating ice water through the jacket as the neutralization reaction proceeded and ethylenediamine dinitrate formed. The ethylenediamine dinitrate solution was then added, via the bottom outlet, to a 12-liter, round bottom flask fitted with a cooling bath and stirrer, which contained 6,145 grams of anhydrous, denatured ethanol cooled to about 3° C. The ethylenediamine dinitrate precipitated as a white crystalline solid. The slurry was stirred for 30 minutes, filtered, and the filter cake washed with about 1,000 grams of fresh denatured, anhydrous ethanol. On drying, 897 grams (95.4 percent yield, m.p. 187°-187.5° C.) of EDDN product was obtained. The EDDN was characterized by FT-IR (Fourier transform-infrared) spectroscopy, DSC (differential scanning calorimetry), and equivalent weight determination. The average particle size of the EDDN was measured using photomicrographs of the product, and was found to be 30 microns.

Provenance & Evidence