Catalytic hydrogenation of o-nitrochlorobenzene to 3,3′-dichlorobenzidine

Kaihua Shen, Shude Li, Dong Hoon Choi

Research output: Contribution to journalArticle

3 Citations (Scopus)

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-nitrochlorobenzene is affected strongly by concentration of base, Pd/C catalyst, and co-catalyst. 1H and 13C NMR spectroscopy confirmed the chemical structures of 2,2′-dichlorohydrazobenzene and 3,3′-dichlorobenzidine.

Original languageEnglish
Pages (from-to)1785-1789
Number of pages5
JournalBulletin of the Korean Chemical Society
Volume23
Issue number12
Publication statusPublished - 2002 Dec 20
Externally publishedYes

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2-chloronitrobenzene
Hydrogenation
Catalysts
Nuclear magnetic resonance spectroscopy
Hydrogen

Keywords

  • 3,3′-Dichlorobenzidine
  • Hydrogenation
  • O-Nitrochlorobenzene
  • Pd/C catalyst

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Catalytic hydrogenation of o-nitrochlorobenzene to 3,3′-dichlorobenzidine. / Shen, Kaihua; Li, Shude; Choi, Dong Hoon.

In: Bulletin of the Korean Chemical Society, Vol. 23, No. 12, 20.12.2002, p. 1785-1789.

Research output: Contribution to journalArticle

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N2 - 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-nitrochlorobenzene is affected strongly by concentration of base, Pd/C catalyst, and co-catalyst. 1H and 13C NMR spectroscopy confirmed the chemical structures of 2,2′-dichlorohydrazobenzene and 3,3′-dichlorobenzidine.

AB - 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-nitrochlorobenzene is affected strongly by concentration of base, Pd/C catalyst, and co-catalyst. 1H and 13C NMR spectroscopy confirmed the chemical structures of 2,2′-dichlorohydrazobenzene and 3,3′-dichlorobenzidine.

KW - 3,3′-Dichlorobenzidine

KW - Hydrogenation

KW - O-Nitrochlorobenzene

KW - Pd/C catalyst

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