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Amino- and hydrodefluorination of polyfluoroaromatic amines with aqueous ammonia in a steel autoclave. Synthesis of highly pure tetrafluorophenylenediamines

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Abstract

The action of aqueous ammonia on hexafluorobenzene in a steel autoclave at 180—220 °C yields a mixture of isomeric tetrafluorophenylenediamines and 2,4,5-trifluorophenylene-1,3-diamine. The content of the hydrodefluorination product significantly depends on the reaction temperature and time. Tetrafluorophenylene-1,3-diamine undergoes hydrodefluorination with aqueous ammonia in a steel autoclave at 200 °C to give 2,4,5-trifluorophenylene-1,3-diamine; when the additives of NH4F and/or FeCl3 are present, 2,5-difluorophenylene-1,3-diamine is additionally formed. The hydrodefluorination products are not formed during bis-aminodefluorination of hexafluorobenzene with aqueous ammonia in a glass reactor or with anhydrous ammonia (in a mixture with aprotic solvent) in a steel autoclave.

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Authors and Affiliations

  1. N N. Vorozhtsov Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent’eva, 630090, Novosibirsk, Russian Federation

    S. Z. Kusov, V. I. Rodionov, T. A. Vaganova, I. K. Shundrina & E. V. Malykhin

  2. Novosibirsk State University, 2 ul. Pirogova, 630090, Novosibirsk, Russian Federation

    E. V. Malykhin

Authors
  1. S. Z. Kusov
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  2. V. I. Rodionov
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  3. T. A. Vaganova
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  4. I. K. Shundrina
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  5. E. V. Malykhin
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Correspondence to E. V. Malykhin.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 806-810, April, 2009.

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Kusov, S.Z., Rodionov, V.I., Vaganova, T.A. et al. Amino- and hydrodefluorination of polyfluoroaromatic amines with aqueous ammonia in a steel autoclave. Synthesis of highly pure tetrafluorophenylenediamines. Russ Chem Bull 58, 823–827 (2009). https://doi.org/10.1007/s11172-009-0101-8

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  • DOI: https://doi.org/10.1007/s11172-009-0101-8

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