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Effect of glucose on lowering Al–Ni alloy consumption in dehalogenation of halogenoanilines

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Abstract

Glucose was tested as a substance increasing the conversion of the hydrodehalogenation reaction applied to industrially important halogenoanilines in aqueous alkaline solution by action of the Raney Al–Ni alloy at room temperature. The quantity of reducing Al–Ni alloy can be decreased down to one half using glucose additive as compared with the dehalogenations performed without its addition. Complete dehalogenation of the tested halogenoanilines is already achieved with the mass ratio of halogenoaniline:NaOH:glucose:Al:Ni = 1:13:5:1.3:0.55. Further, the reaction mixture after dehalogenation, adjusting of pH with phosphoric acid and filtration can already be described as biodegradable. The course of reduction of 2-chloro-, 3-chloro-, and 4-bromoaniline was monitored using 1H NMR spectroscopy.

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Acknowledgments

We are grateful to the Technological Agency of Czech Republic (project No.: TA01010606) for financial support.

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Authors and Affiliations

  1. Institute of Environmental and Chemical Engineering, Faculty of Chemical Technology, University of Pardubice, Pardubice, Czech Republic

    Tomáš Weidlich, Jakub Opršal & Anna Krejčová

  2. Department of Graphic Arts and Photophysics, Faculty of Chemical Technology, University of Pardubice, Pardubice, Czech Republic

    Bohumil Jašúrek

Authors
  1. Tomáš Weidlich
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  2. Jakub Opršal
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  3. Anna Krejčová
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  4. Bohumil Jašúrek
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Correspondence to Tomáš Weidlich.

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Weidlich, T., Opršal, J., Krejčová, A. et al. Effect of glucose on lowering Al–Ni alloy consumption in dehalogenation of halogenoanilines. Monatsh Chem 146, 613–620 (2015). https://doi.org/10.1007/s00706-014-1344-0

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  • DOI: https://doi.org/10.1007/s00706-014-1344-0

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