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Preparation of Metal Corrosion Inhibitors from Arylamines and Butadiene

  • Organic Synthesis and Industrial Organic Chemistry
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Abstract

N- and С-octadienyl-substituted 1-, 2-naphthylamines and 6-aminoquinolines exhibiting anticorrosion activity in a hydrochloric acid medium were prepared. The reaction of 2-naphthylamine with butadiene in the presence of palladium complexes yields a mixture of 1- or 3-octadienyl-substituted derivatives. The first step of the reaction is the formation of an N-alkadienylated derivative, which subsequently undergoes the palladium-catalyzed Claisen aromatic amine rearrangement. The reaction of α-naphthylamine with butadiene in the presence of a palladium catalyst and trifluoroacetic acid yields N- and C-alkenylation products. In palladium-catalyzed reactions of butadiene with 6-aminoquinoline, N-(2,7-octadienyl)- or N,N-bis(2,7-octadienyl)aminoquinoline was obtained depending on the telomerization conditions.

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, Ufa, 450054, Bashkortostan, Russia

    R. N. Khusnitdinov & R. R. Gataullin

Authors
  1. R. N. Khusnitdinov
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  2. R. R. Gataullin
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Contributions

Both authors: experiments on the synthesis and isolation of the substances, calculations of the anticorrosion activity, and manuscript preparation; R.N. Khusnitdinov: sample preparation and anticorrosion activity tests; R.R. Gataullin: interpretation of the spectroscopic data.

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Correspondence to R. N. Khusnitdinov.

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The authors declare that they have no conflict of interest.

Additional information

Translated from Zhurnal Prikladnoi Khimii, No. 4, pp. 517–523, March, 2022 https://doi.org/10.31857/S0044461822040132

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Khusnitdinov, R.N., Gataullin, R.R. Preparation of Metal Corrosion Inhibitors from Arylamines and Butadiene. Russ J Appl Chem 95, 575–581 (2022). https://doi.org/10.1134/S1070427222040140

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  • DOI: https://doi.org/10.1134/S1070427222040140

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