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Catalytic reduction of aromatic polynitro compounds

1. Hydrogenation of 3,5-dinitrophenyl phenyl ether

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The liquid-phase catalytic hydrogenation of 3,5-dinitrophenyl phenyl ether to give 3,5-diaminophenyl phenyl ether in the presence of Group VIII metals as catalysts has been investigated. The main kinetic characteristics of the process have been established. The reduction occursvia the formation of 5-amino-3-nitrophenyl phenyl ether. In terms of their activity, the catalysts studied can be arranged in the following sequence: 1% Pd/Sibunit> 2 % Pd/C > Lindlare Pd > 5% Ru/Sibunit > Raney Ni. The selectivity of the process with respect to intermediate 5-amino-3-nitrophenyl phenyl ether depends on the relative adsorption abilities of mono- and dinitro compounds. A promoting effect of water during hydrogenation of 3,5-dinitrophenyl phenyl ether in isopropanol or 1,4-dioxane has been noted. Catalytic synthesis of 3,5-diaminophenyl phenyl ether has been carried out for the first time.

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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1716–1719, September, 1995.

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Zakharychev, D.P., Litvin, E.F. & Sharf, V.Z. Catalytic reduction of aromatic polynitro compounds. Russ Chem Bull 44, 1648–1650 (1995). https://doi.org/10.1007/BF01151284

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Key words

  • 3,5-dinitrophenyl phenyl ether
  • hydrogenation
  • Pd, Ru, and Ni catalysts
  • 5-amino-3-nitrophenyl phenyl ether
  • 3,5-diaminophenyl phenyl ether