1998. ------. [LARSON, A. T.] (E. I. du Pont de Nemours & Co.). Amine Synthesis. United States Patent 2,497,310, Feb. 14, 1950. Chem. Abs., vol. 44, 1950, p. 4489.

Organic amines are prepared by treating an unsaturated compound containing a nonbenzenoid double bond with CO, H₂ and NH₃ or a substituted amine having at least 1 H attached to the amino N. At 160°-260° with 100-2,000 atm., Co, Ni, Ru, Fe, and Cu compounds, particularly carbonyls, are satisfactory catalysts. Et₂O (75 ml.), 17 gm. NH₃, 20 gm. fused Co catalyst, and 28 gm. C₂H₄ were heated 1.5 hr. at 170°-262° under 470-755 atm. of gas (4H₂:CO); distillation gave a mixture of propylamines. C₂H₄ (14 gm.), 17 gm. NH_3, 64 ml. cyclohexane, and 10 gm. reduced CuO catalyst heated in a Ag-lined pressure vessel 1 hr. at 246°-250° under 560-850 atm. gas (CO: 2H₂) gave on distillation 13.1 gm. Pr₂NH, b. 108°-125°, and a mixture of EtCONH₂ and 2-ethyl-3,5-dimethylpyridine.