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Specific features of the Mannich synthesis of N-(dialkylaminomethyl)(meth)acrylamides based on higher amines

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Abstract

The influence of the structure of higher secondary linear amines (di-n-butylamine (DBA), di-n-octylamine (DOA)), amides (methacrylamide (MAA), acrylamide (AA)) and additives of surfactants of different nature on the synthesis of promising cationic monomers, higher N-(dialkylaminomethyl)(meth)acrylamides, via the Mannich reaction in two-phase water-organic systems was determined. At the initial equimolar ratio of DBA, formaldehyde, and MAA under mild conditions, a high yield of the target monomer (96%) is achieved, and the introduction of a surfactant leads to the initial acceleration of the reaction but does not almost increase the yield. This is due to the manifestation of the effect of “micellar autocatalysis” in the absence of surfactants, since the formed amphi-philic aminoamide has surfactant properties. When MAA is replaced by AA, the yield of the aminoamide monomer does not exceed 80% because of the side formation of secondary amine addition products to the C=C bonds of the starting or formed amide. When using DOA, the reaction does not proceed to an appreciable extent because of steric shielding of the reaction center in the aminomethylating intermediate.

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Authors and Affiliations

  1. R. E. Alekseev Nizhny Novgorod State Technical University, 24 ul. Minina, 603950, Nizhny Novgorod, Russian Federation

    I. R. Arifullin, O. A. Kazantsev, M. V. Savinova, S. A. Ozhogin & S. I. Kamorina

  2. N. I. Lobachevsky National Research Nizhny Novgorod State University, 23 prosp. Gagarina, 603022, Nizhny Novgorod, Russian Federation

    S. A. Ozhogin

Authors
  1. I. R. Arifullin
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  2. O. A. Kazantsev
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  3. M. V. Savinova
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  4. S. A. Ozhogin
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  5. S. I. Kamorina
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Corresponding author

Correspondence to I. R. Arifullin.

Additional information

This work was carried out in terms of state assignment in the sphere of scientific activity (theme No. FSWE-2020-0008, study of micellar catalysis effect) and financially supported by the grant of the President of the Russian Federation for young scientists and post-graduate students performing promising research and developments on priority directions of modernization of the Russian economy (SP-4035.2021.1, studies of the influence of the reagent structure on the Mannich reaction).

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izyestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 5, pp. 1178–1185, May, 2023.

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Arifullin, I.R., Kazantsev, O.A., Savinova, M.V. et al. Specific features of the Mannich synthesis of N-(dialkylaminomethyl)(meth)acrylamides based on higher amines. Russ Chem Bull 72, 1178–1185 (2023). https://doi.org/10.1007/s11172-023-3887-x

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  • DOI: https://doi.org/10.1007/s11172-023-3887-x

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