Syntheses with acrylonitrile. IX. Reaction of acrylonitrile with ammonia and preparation of trimethylenediamine was written by Terent’ev, A. P.;Chursina, K. I.;Kost, A. N.. And the article was included in Zhurnal Obshchei Khimii in 1950.Safety of 3,3′,3”-Nitrilotripropanenitrile This article mentions the following:
Reaction of CH2:CHCN (I) with NH3 involves consecutive equilibrium with H2NCH2CH2CN, HN(CH2CH2CN)2, and N(CH2CH2CN)3. Slow addition of 95 g. I to 950 ml. 32% NH4OH with cooling 2 hrs. below 35° and stirring 30 min. gave 30% β-aminopropionitrile and 47.2% β, β’-iminodipropionitrile, and a small amount of the trisubstitution product. Decrease of the amount of NH4OH lowers the primary product yield, but if the concentration of the mixture is done in an NH3 stream the yield rises to 34-6%. H2NCH2CH2CN, b14 77-8°, b18 84-6°, b23 89°, nD20 1.4390, d420 0.9584 [HCl salt, m. 163-3.5° (from EtOH)]; HN(CH2CH2CN)2, b14 177-9 °, b22 209-11°, nD20 1.4630, d420 1.0196 [HCl salt, m. 147-8° (from MeOH), gives with BzCl in C6H6 BzN(CH2CH2CN)2, m. 112° (from MeOH); PhSO2Cl gave the PhSO2 analog, m. 88° (from MeOH)]. Heating 6.2 g. HN(CH2CH2CN)2 and 8 g. I in an ampul 60 hrs. at 160-80° gave 40% N(CH2CH2CN)3, m. 57-8° (from EtOH-Et2O-H2O). Addition of 14 g. H2NCH2CH2CN in 450 ml. BuOH to 30 g. Na-K alloy (2% K) and rapid heating gave, after the usual steam distillation from acidified solution, 81% trimethylenediamine-HCl, m. 242° (from EtOH); use of old nitrile or of iso-AmOH gave lower yields; free base, readily obtained in 74% yield from the HCl salt with NaOH and Et2O, b756 136-8°, b735 134-6°, nD20 1.4590, d420 0.8834 (dried over Na before distillation); BaO or Na2O gave lower yields. Similar reduction of HN(CH2CH2CN)2 in BuOH gave 22-5% HN(CH2CH2CH2NH2)2, b5-6 105-6°, b9 108°, b17 114-17°, nD20 1.4846, d420 0.9386; HCl salt, decompose 259° (from aqueous MeOH); tripicrate, decompose 226-7° (from H2O). In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Safety of 3,3′,3”-Nitrilotripropanenitrile).
3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Safety of 3,3′,3”-Nitrilotripropanenitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts