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Study of dehalogenation of halogenoanilines using Raney Al–Ni alloy in aqueous medium at room temperature

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Abstract

Dehalogenation of halogenated anilines by action of powdered aluminium–nickel alloy in aqueous alkaline solution at room temperature has been studied. The reaction course was monitored by means of 1H nuclear magnetic resonance (NMR) spectroscopy. The rates of dehalogenation of 4-bromo-, 4-chloro-, 4-fluoro- and 3-chloroaniline were compared under conditions of minimum necessary excess of Al–Ni alloy as reducing agent in edetane buffer medium at pH 10.9. The dehalogenation rates of halogenated anilines decreased in the following order: 3-chloroaniline > 4-bromoaniline ≥ 4-chloroaniline > 4-fluoroaniline. On the basis of the results obtained in buffers, the dehalogenation method of aqueous solutions of halogenoanilines was verified using NaOH as the base.

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Acknowledgments

We are grateful to the Grant Agency of the Czech Republic (203/07/P248) and Ministry of Education, Youth and Sports of the Czech Republic MSM 0021627502 for financial support.

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Authors and Affiliations

  1. Faculty of Chemical Technology, Institute of Environmental and Chemical Engineering, University of Pardubice, Studentska 573, 532 10, Pardubice, Czech Republic

    Tomáš Weidlich & Anna Krejčová

  2. Department of Chemistry, Faculty of Science, Masaryk University, Kotlarska 2, 611 37, Brno, Czech Republic

    Lubomír Prokeš

Authors
  1. Tomáš Weidlich
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  2. Anna Krejčová
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Correspondence to Tomáš Weidlich.

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Weidlich, T., Krejčová, A. & Prokeš, L. Study of dehalogenation of halogenoanilines using Raney Al–Ni alloy in aqueous medium at room temperature. Monatsh Chem 141, 1015–1020 (2010). https://doi.org/10.1007/s00706-010-0362-9

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  • DOI: https://doi.org/10.1007/s00706-010-0362-9

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