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

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Reaction Steps

Example 1 was repeated using 2-butyl-2-ethyl-4-cyanobutanal as the starting material. To this end, 33.6 g per hour of 2-butyl-2-ethyl-4-cyanobutanal (purity 89.0%, 29.9 g, 0.165 mol) and 1344 ml (806 g, 47.4 mol) per hour of liquid ammonia were pumped at 250 bar and 60° C. through the imination reactor. The product stream was subsequently passed through the hydrogenation reactor from bottom to top at 250 bar and 120° C. while simultaneously passing 100 l(S.T.P.)/h (4.5 mol) of hydrogen through the reactor. The product stream was decompressed to atmospheric pressure and NH3 was removed by distillation. The product from 16.7 hours was separated 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 mmHg) and 267.5 g of 2-butyl- 2-ethylpentane-1,5-diamine (b.p.=105° C./2 mmHg). The diamine yield was 52.1% of theory.

Provenance & Evidence