Propylene Oxide → 2-Propanol, 1,1'-[[2-[(2-hydroxypropyl)amino]ethyl]imino]bis-

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Reaction Steps

(V-a): Propylene oxide (181.6 g, 0.3 mol) in 25 mL of absolute ethanol was added dropwise for 4.5 hours to a solution of N,N'-bis(2-hydroxypropyl)ethylenediamine (IV-a) (55 g, 0.3 mol) in 50 mL each of absolute ethanol, methanol and distilled water at 80° C. The reaction mixture was cooled and concentrated to give a milky white viscous suspension. The suspension was dissolved in ether and dried over anhydrous sodium sulfate. Unreacted (IV-a) precipitated and was removed by filtration. Ether was removed from the clear filtrate to produce a viscous liquid. Fractional distillation of the oil produced N,N,N'-tris(2-hydroxypropyl)ethylenediamine[bp. 140° C. at 0.15 mm; yield 55 percent; IR(neet); 3350(broad OH); NMR(CDCl3): δ 3.8(broad m,3H); 2.5(broad m,10H); 1.1(d,9H)].

Provenance & Evidence