The reductive amination of nonanal with ammonia over group 8 metals has been studied in ethanol at 50° C a nd 8 MPa-H2 to compare the selectivity of these metals for the formation of the primary amine (nonylamine), the secondary amine (dinonylamine) and the tertiary amine (trinonylamine). The yield of the primary amine increased in the order: Pd < Os < Pt < Rh < Ir < Raney Ni = Ru < Raney Co. High yields of the primary amine were obtained with Raney Co (94%), Raney Ni (87%) and Ru (87% ) as catalysts, while over Pd catalyst the yield was o nly 24% which was t he smallest of t he metals investigated. Over Pd and Os catalysts the secondary amine was formed in larger amounts than the primary amine (62 and 53%, respectively). The tertiary amine was formed only in small amounts over Pd an d Os catalysts (6 and 1 %, respectively). In general, the formation of t he primary amine was n ot increased by the addition of a mmonium chloride. On t he other hand, the formation of the tertiary amine was greatly increased over Pd catalyst from 6 % to 45% in the presence of ammonium chloride. The max imum amounts of the Schiff -base, N-nonylidenenonylamine, found as an intermediate during the reaction were 69% over Raney Ni, 67% over Raney Co a nd 53% over Ru which were in a ll cases much greater than the amounts of the secondary amine produced over the respective metals. These results in dicate that the reaction pathways leading to the formation of the primary amine involves t he one via th e Schiff base as the intermediate which may be decomposed into t he primary amine and 1-nonanimine, by the ad dition of ammonia. Significant amounts of N, N-dinonyl-1-nonenylamine, a tertiary amine precursor, were also formed as an intermediate during the reaction even w hen the tertiary amine was n ot formed at all. The results show that, similarly to t he Schiff base, the tertiary amine precursor may be decomposed into the secondary amine and the imine in the presence of ammonia. The different sel ectivities of catalyst metals for the formation of primary and secondary amines have been discussed on the basis of the reaction pathways which involve the isomerization of the Schiff base to the enamine.