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Communication | Regular issue | Vol 16, No. 11, 1981, pp.1863-1871
Published online, 1st January, 1970
DOI: 10.3987/R-1981-11-1863
■ Isomerization and Hydrogenation of Nitrogen-containing Organic Compounds Catalyzed by Heterogeneous Catalysts

Hideshi Hattori and Kozo Tanabe*

*Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan

Abstract

The double-bond isomerization of 1-N-pyrrolidino-2-propene and N,N-dimethyl-2-propenylamine were studied at 40°C over MgO, CaO, SrO, BaO, La2O3, ThO2, ZrO2, ZnO etc. It was found that MgO and CaO which have strong basic sites on the surfaces exhibited a high catalytic activity, the selectivity for the formation of 1-N-pyrrolidino-1-propene being more than 80 %. The double-bond migration of the allylamines is suggested to proceed via anionic intermediates in which the cis form is much more stable than the trans form. For the hydrogenation of N,N-dimethyl-2-propenylamine, the activity as well as the selectivity of nickel catalysts supported on MgO, CaO, La2O3, ThO2, TiO2, ZrO2 etc. was examined at 0°C. Nickel on MgO was found to give 100 % conversion and almost 100 % selectivity for the formation of N,N-dimethylpropenylamine. It is suggested that nickel catalyst becomes active when supported on basic oxides. The reaction path is discussed on the basis of experiments using deuterium as a tracer.