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Cataytic Hydrogenation of o-Nitrochlorbenzene to 3,3'-Dichlorobenzidine


Abstract

2,2'-Dichlorohydroazobenzene was prepared by selective hydrogenation of o-nitrochlorobenzene with hydrogen in the presence of 0.8% and 5% Pd/C catalyst. O-Chloroaniline was a minor product in the catalytic hydrogenation of o-nitrochlorobenzene. The effects of base, Pd/C catalyst, and co-catalyst were discussed on catalytic hydrogenation. 2,2'-Dichlorohydroazobenzene, as an intermediate, was rearranged to 3,3'-dichlorobenzidine after reacting with HCl. It was shown that selectivity of catalytic hydrogenation of o-nitro-chlorobenzene is affected strongly by concentration of base, Pd/C catalyst, and co-catalyst. $^1Hand^{13}C$NMR spectroscopy confirmed the chemical structures of 2,2'-dichlorohydrazobenzene and 3,3'-dichlorobenzidine.

Keywords

References

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Cited by

  1. Effect of Preparation Conditions on the Hydrogenation Activity and Metal Dispersion of Pt/C and Pd/C Catalysts vol.26, pp.4, 2005, https://doi.org/10.5012/bkcs.2005.26.4.563
  2. Hydrogenation of o-chloronitrobenzene on a Pd/C catalyst doped with metal oxide nanoparticles vol.141, pp.1, 2002, https://doi.org/10.1016/j.cej.2008.04.006