Highly Selective Hydrogenation of Adiponitrile to Hexamethyleneimine Catalyzed by Carbon Nitrogen Composited Nickel Catalysts

doi:10.7503/cjcu20240003

Abstract

Abstract:

Hexamethyleneimine（HMI） is a crucial intermediate in the production of pharmaceuticals and agrochemicals， including penicillin， herbicides， and fungicides. In this study， supported Ni-based catalysts were prepared using solvent-assisted mechanochemical ball milling and pyrolysis， and the catalytic performance for the hydrogenation of 1，6-adiponitrile（ADN） to HMI was evaluate. The results demonstrated that the supported Ni-based catalyst Ni/IM-C（R） exhibited high activity for the hydrogenation of ADN to HMI in 98% yield. The catalyst Ni/IM-C（R） was prepared by co-ball milling nickel acetate， 2-methylimidazole and activated carbon， followed by calcination in N₂ and then reduced by H₂. The surface structures and the chemical properties of the Ni/IM-C（R） catalyst were characterized via various techniques， including X-ray diffraction， X-ray photoelectron spectroscopy， scanning electron microscopy， energy-dispersive X-ray spectroscopy， transmission electron microscope， and N₂ adsorption-desorption measurements. The characterization results indicated that nitrogen-doped carbon improved the dispersion of Ni nanoparticles in the Ni/IM-C（R） catalyst. The catalyst Ni/IM-C（R） displayed small Ni nanoparticles with high surface， which directed the high activity for the hydrogenation of ADN to HMI. Without additives， the Ni/IM-C（R） catalyzed hydrogenation of ADN exhibited excellent activity and high selectivity towards HMI. The Ni/IM-C（R） catalyst is stable and recyclable for several times without deactivation. The Ni/IM-C（R） catalyst is simple to be prepared and the Ni/IM-C（R） catalyzed hydrogenation of ADN is promising for industrial applications.

Key words: Hexamethyleneimine, Adiponitrile, Nickel catalyst, Selective hydrogenation

CLC Number:

O643

TrendMD:

ZHANG Chenyang, JIA Chenxu, HUANG Jun. Highly Selective Hydrogenation of Adiponitrile to Hexamethyleneimine Catalyzed by Carbon Nitrogen Composited Nickel Catalysts[J]. Chem. J. Chinese Universities, 2024, 45(4): 20240003.

Figures/Tables 13

References 31

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Reaction	Ni content ^a /leaching ^b （mass fraction， %）
Fresh catalyst	0/＜0.05
1st recycle	0/＜0.05
2nd recycle	0/＜0.05

Reaction	Ni content ^a /leaching ^b （mass fraction， %）
Fresh catalyst	0/＜0.05
1st recycle	0/＜0.05
2nd recycle	0/＜0.05

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