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Research Article Open access CC BY 4.0

N,N’-Dialkylimidazolium Dimethyl Phosphates – Promising Media and Catalysts at the Same Time for Condensation Reactions

S. Brica, L. Freimane, L. Kulikovska, A. Zicmanis

Chemical Science International Journal · pp. 1–9 · Published 22 Jun 2017

10.9734/CSJI/2017/34482

Abstract

The objective of the current work is the elaboration of an alternative method for synthesis of N,N’-dialkylimidazolium dimethyl phosphates – ionic liquids useful both as media and catalysts for condensation reactions in organic synthesis. The proposed method consists of alkylation of 1-substituted imidazoles with 1-alkyl chlorides in a closed steel cylinder followed by treating of obtained imidazolium chlorides with trimethyl phosphate. Data of qualitative analyses made by 1H NMR, quantitative analysis made by potentiometric titration, and thermal stability measured by thermogravimetry of these elaborated advanced materials are presented. Two successful examples of their use in the Knoevenagel condensation reactions are demonstrated.

Ionic liquids dimethyl phosphate anion synthesis condensation reaction

References (16)

  1. 1 Room-Temperature Ionic Liquids: Solvents for Synthesis and Catalysis. 2 [DOI]
  2. 2 Ionic Liquids in Synthesis [DOI]
  3. 3 Ionic Liquids in Synthesis [DOI]
  4. 4 Ionic liquids and catalysis: Recent progress from knowledge to applications [DOI]
  5. 5 Fluoride ion as a base in organic synthesis [DOI]
  6. 6 Direct conversion of glucose to 5-(hydroxymethyl)furfural in ionic liquids with lanthanide catalysts [DOI]
  7. 7 Imidazolium dialkylphosphates—a class of versatile, halogen-free and hydrolytically stable ionic liquids [DOI]
  8. 8 Knoevenagel Reaction in [MMIm][MSO4]: Synthesis of Coumarins [DOI]
  9. 9 Halogen-free synthesis of symmetrical 1,3-dialkylimidazolium ionic liquids using non-enolisable starting materials [DOI]
  10. 10 Organic Reactions in Ionic Liquids: Knoevenagel Condensation Catalyzed by Ethylenediammonium Diacetate [DOI]
  11. 11 Dialkylimidazolium dimethyl phosphates as solvents and catalysts for the Knoevenagel condensation reaction [DOI]
  12. 12 One-pot conversion of alkyl aldehydes into substituted propanoic acids via Knoevenagel condensation with Meldrum’s acid [DOI]
  13. 13 When Chlorides are the Most Reactive: A Simple Route towards Diverse Mono- and Dicationic Dimethyl Phosphate Ionic Liquids [DOI]
  14. 14 Studying of the Basicity of Ionic Liquids by Potentiometric Titration [DOI]
  15. 15 Organic Reactions in Ionic Liquids: Knoevenagel Condensation Catalyzed by Ethylenediammonium Diacetate. [DOI]
  16. 16 Designing highly efficient solvents for the Knoevenagel condensation: two novel dicationic dimethyl phosphate ionic liquids [DOI]

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