Ammonia → 2-Butyl-2-ethyl-1,5-pentanediamine

Participants

Reaction Steps

Example 1 was repeated using 2-butyl-2-ethyl-4-cyanobutanal as a starting material. 33.6 g of 2-ethyl-2-butyl-4-cyanobutanal (purity: 89.0%, 29.9 g, 0.165 mol) and 1,344 ml (806 g, 47.4 mol) of liquid ammonia were pumped per hour at 250 bar and 60° C. through the imination reactor. The product was then passed through the hydrogenation reactor from bottom to top at 250 bar and 120° C. while simultaneously passing through 100 l (s.t.p.)/h (4.5 mol) of hydrogen. After decompression to atmospheric pressure, NH3 is removed by distillation. The product from 16.7 hours was separated into its components by fractional distillation on a 30 cm packed column (3 mm glass rings), giving 166.8 g of 3-butyl-3-ethylpiperidine (b.p.=73° to 75° C./2 mm Hg) and 267.5 g of 2-ethyl-2-butylpentane-1,5-diamine (b.p.=105° C./2 mm Hg). The yield of diamine was 52.1% of theory.

Provenance & Evidence