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Synthesis of acyclic quaternary ammonium compounds containing ω-alkoxyethyl and 2-hydroxyethyl substituents at the nitrogen atom

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Abstract

A series of acyclic symmetric quaternary ammonium chlorides Me2(HOCH2CH2)N+(CH2CH2O)nR Cl– (n = 1, R = n-C9H19; n = 2, R = n-C6H13; n = 3, R = n-C3H7) was synthesized by alkylation of the corresponding tertiary amines Me2N(CH2CH2O)nR with ethylene chlorohydrin in a two-phase system, using water as a solvent. The tertiary amines were synthesized in a heterogeneous system organic phase—aqueous phase, using an aqueous solution of Me2NH and a solid alkali. The intermediate monoethers of ethylene, diand triethylene glycol were obtained in high yield via a phase-transfer alkylation in dioxane, using solid KOH. The proton and carbon atom signals in the NMR spectra of the synthesized amines and ammonium chlorides were assigned based on the data of heteronuclear correlations (1H, 13C).

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Authors and Affiliations

  1. State Scientific-Research Institute of Chemical Reagents and High Purity Substances, 3 Bogorodsky val, 107076, Moscow, Russian Federation

    K. V. Tcarkova, S. K. Belus’, A. V. Kharlamov & N. A. Bondarenko

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    O. I. Artyushin

Authors
  1. K. V. Tcarkova
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  2. S. K. Belus’
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  3. O. I. Artyushin
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  4. A. V. Kharlamov
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  5. N. A. Bondarenko
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Corresponding author

Correspondence to N. A. Bondarenko.

Additional information

To 90th birthday anniversary of the Corresponding Member of the Russian Academy of Sciences T. A. Mastryukova (1925—2006).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2697—2701, November, 2015.

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Tcarkova, K.V., Belus’, S.K., Artyushin, O.I. et al. Synthesis of acyclic quaternary ammonium compounds containing ω-alkoxyethyl and 2-hydroxyethyl substituents at the nitrogen atom. Russ Chem Bull 64, 2697–2701 (2015). https://doi.org/10.1007/s11172-015-1209-7

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  • DOI: https://doi.org/10.1007/s11172-015-1209-7

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