Ethylenediamine → Propanenitrile, 3,3',3'',3'''-(1,2-ethanediyldinitrilo)tetrakis-

Temperature

25 °C

Acrylonitrile (110 g, 137 cm3, 2.08 mol) was added to a vigorously stirred mixture of ethylenediamine (25 g, 27.8 cm3, 0.416 mol) and water (294 cm3) at 40° C. over 30 min. During the addition, it was necessary to cool the mixture with a 25° C. water bath to maintain temperature at 40° C. The mixture was then stirred for additional 2 hours at 40° C. and 2 hours at 80° C. Excess acrylonitrile and half of the water were evaporated off and the residue, on cooling to room temperature, gave a white solid which was recrystallised from MeOH-water (9:1) to give pure product 3,3′,3″,3′″-(ethane-1,2-diylbis(azanetriyl))tetrapropanenitrile (86.6 g, 76.4%) as white crystals, mp 63-65° C.

1. additionDuring the addition, it
2. temperatureto maintain temperature at 40° C
3. customExcess acrylonitrile and half of the water were evaporated off
4. temperaturethe residue, on cooling to room temperature
5. customgave a white solid which
6. customwas recrystallised from MeOH-water (9:1)

ORD record

ord-e2d94c2294cb43d19944cab8fff96316

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08802609B2