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Synthesis of some acyclic quaternary ammonium compounds. Alkylation of secondary and tertiary amines in a two-phase system

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Abstract

A series of acyclic symmetrical and asymmetrical quaternary ammonium chlorides of the general formula R1R2R3N+AR4Cl– (R1 = Me, Bu; R2 = n-C12H25, PhCH2, C n H2n+1(OCH2CH2) m , n = 9 and 12, m = 1 and 2; R3 = n-C12H25, PhCH2, HOCH2CH2,–OOCCH2; R4 = n-C12H25, PhCH2; A = (CH2CH2O)1,2, CH2C(O)O) was synthesized by the alkylation of tertiary amines in a two-phase system containing water. A convenient method for the synthesis of the initial symmetrical and asymmetrical tertiary amines of the general formula MeNR1R2 (R1 = Me, Bu; R2 = n-C12H25, PhCH2, CnH2n+1(OCH2CH2) m , n = 9 and 12, m = 1 and 2) in an organic phase-aqueous phase heterogeneous system, which allows the use of aqueous solutions of alkali and amines, was developed. The improved method for the preparation of intermediate ethylene glycol and diethylene glycol monoethers is monoalkylation of glycols in dioxane using solid KOH in a two-phase system.

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Authors and Affiliations

  1. State Scientific-Research Institute of Chemical Reagents and High Purity Substances (IREA), 3 ul. Bogorodskii val, 107076, Moscow, Russian Federation

    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. A. V. Kharlamov
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  2. O. I. Artyushin
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  3. N. A. Bondarenko
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Correspondence to N. A. Bondarenko.

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Dedicated to Academician of the Russian Academy of Sciences Yu. N. Bubnov on the occasion of his 80th birthday and the 60th anniversary of the foundation of A. N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2445—2454, November, 2014.

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Kharlamov, A.V., Artyushin, O.I. & Bondarenko, N.A. Synthesis of some acyclic quaternary ammonium compounds. Alkylation of secondary and tertiary amines in a two-phase system. Russ Chem Bull 63, 2445–2454 (2014). https://doi.org/10.1007/s11172-014-0761-x

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  • DOI: https://doi.org/10.1007/s11172-014-0761-x

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