Ethylenediamine → 2-Propanol, 1,1'-(1,2-ethanediyldiimino)bis-

Participants

Reaction Conditions

Reaction Steps

(IV-a): Propylene oxide (142.4 g, 2.4 mol) was added dropwise over a period of 11 hours to a solution of ethylenediamine (71.9 g, 1.2 mol) in 25 mL absolute ethanol and 10 mL of nitrogen purged distilled water at 90° C. After addition, the reaction was maintained for an additional hour, then cooled to room temperature (about 20° C.). The reaction solution was concentrated by rotary evaporation to give a milky white suspension which, upon dissolution in anhydrous ether, produced a white precipitate of N,N'-bis(2-hydroxypropyl)ethylenediamine in 28.5 percent yield. The product was crystallized from methanol/ethanol [m.p. 132° C., IR(Nujol): 3250(OH); NMR(MeOHd4): δ3.8(m,2H); 2.6(t,8H); 1.2(d,6H)].

Provenance & Evidence