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Electrochemical Amination of Isomeric Chloroanilines in Aqueous Solutions of Sulfuric Acid

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Abstract

The processes of indirect cathodic amination of para, ortho, and meta-chloroanilines by means of the Ti(IV)–NH2OH system in aqueous solutions of 9–17 M sulfuric acid are studied. The efficiency and regioselectivity of radical cation substitution increase with the increase in electrolyte acidity and temperature. Functionalization of para-chloroaniline in 17 М H2SO4 produces 4-chloro-1,3-phenylenediamine with the mass fraction of 99.7%. Its yield corresponding to the complete conversion of hydroxylamine is 91%. The only side product of amination is para-phenylidenediamine.

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Funding

This study was supported in the frames of the State Program of RF on the Competitive Growth of the Kazan State University and also by the Russian Foundation for Basic Research (project no. 16-03-01061).

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Authors and Affiliations

  1. Kazan Federal University, Butlerov Chemical Institute, 420008, Kazan, Russia

    Yu. A. Lisitsyn & A. V. Sukhov

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  1. Yu. A. Lisitsyn
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  2. A. V. Sukhov
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Correspondence to Yu. A. Lisitsyn.

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The authors declare the absence of any conflict of interests.

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Translated by T. Safonova

Published on the basis of materials of the XIX All-Russian Conference “Electrochemistry of Organic Compounds” (EKHOS-2018) (with international participation), Novocherkassk, 2018.

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Lisitsyn, Y.A., Sukhov, A.V. Electrochemical Amination of Isomeric Chloroanilines in Aqueous Solutions of Sulfuric Acid. Russ J Electrochem 56, 426–430 (2020). https://doi.org/10.1134/S1023193520050080

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  • DOI: https://doi.org/10.1134/S1023193520050080

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