Solubility determinations in anhydrous ethylenediamine
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Although the preparation of ethylenediamine is reported in the literature as early as 1853, the first isolation of the pure anhydrous compound was performed by A. W. Hoffmann in 1858. He prepared the pure diamine by repeated distillations from metallic sodium, and reported on the great stability of the 111ono-hydrate as a hindrance to obtaining the compound in a pure state, More recently, in 1934, Bailar at the University of Illinois reacted the crude diamine with zinc oxalate to give a salt which is stable at room temperature and may be heated to 200° in vacuo (all temperatures in degrees Centigrade unless otherwise noted) where it decomposes and ethylenediamine distills over. He obtained the pure compound by redistilling from sodium, and identified the salt as being zinc oxalate with one molecule of ethylenediamine attached. Wilson2 in 1935 recommended the use of sodium hydroxide as a dehydrating agent before distilling from metallic sodium. Although considerable work has been done with ethylenediamine in aqueous solutions, 9, 12 and many complex compounds have been formed with other substances and ethylenediamine, 10, 11, 13 relatively little bas been done with the compound in an anhydrous condition. Putnam and Kobe3 have reported on the conductances and solubilities of several salts in anhydrous ethylenediamine. Kobe also worked with Isbin8 using ethylenediamine, ethanol amine, and ethylene glycol to relate the solvent action of these three related compounds on the same salts. Bromley and Luder9 have studied the conductances of potassium iodide and several silver salts in the anhydrous ethylenediamine.