Chinese Journal of Applied Chemistry ›› 2019, Vol. 36 ›› Issue (9): 1044-1052.DOI: 10.11944/j.issn.1000-0518.2019.09.190036

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Solubility Properties of 1-Alkyl-4-amino-1,2,4-triazolium Energetic Ionic Liquids

GAO Boa(),YANG Hongweia,TIAN Shaopenga,ZHAO Yuzhena,TIAN Tianb*()   

  1. aSchool of Science,Xijing University,Xi'an 710123,China
    bMaterials Science and Engineering,Hebei University of Engineering,Handan,Hebei 056038,China
  • Received:2019-02-13 Accepted:2019-05-28 Published:2019-09-05 Online:2019-09-05
  • Contact: Tian TIAN
  • Supported by:
    Supported by the Special Scientific Research Project of Shaanxi Provincial Education Department(No.18Jk1205), and the Natural Science Foundation Youth Fund Project of Hebei(No. E2018402211)

Abstract:

Based on NO3-, ClO4-, N(CN)2-, [2,4,5-TNI]-, [3,5-DNTZ]- anions, a series of 1-alkyl-4-amino-1,2,4-triazolium energetic ionic liquids(EILs) were synthesized. The structures were characterized by 1H NMR spectroscopy. The interaction energies of EILs-solvents and dipole moment of the 1-alkyl-4-amino-1,2,4-triazolium EILs were calculated using ab initio at MP2/6-311G++(2d,p). The relationships between the solubility and molecular structure, common solvents, and the interaction energies of EILs-solvents, etc., were discussed systematically. The results showed that the |ΔE| between [BATZ]NO3 and water had the biggest value of 40.7 kJ/mol with the different cations and the |ΔE| of [BATZ][3,5-DNTZ] and water possessed the biggest value of 45.1 kJ/mol with the same cation. The dipole moment of the above EILs was in the following order:[BATZ][3,5-DNTZ]>[BATZ][2,4,5-TNI]>[BATZ]N(CN)2>[BATZ]ClO4>[RATZ]NO3. The solubility of the title energetic ionic liquids increased with decreasing dielectric constant of solvent. With the increase of the alkyl chain length, the interaction energies of EILs-solvents, the anion size , and the solubility in polar solvents all decreased. The solubility in polar solvents was in the following order:[BATZ][3,5-DNTZ]>[BATZ][2,4,5-TNI]>[BATZ]NO3>[BATZ]ClO4>[BATZ]N(CN)2>[PATZ]NO3>[HATZ]NO3>[DATZ]NO3, and [BATZ][2,4,5-TNI] had the highest solubility of 10.0327 g/10 g in water.

Key words: energetic ionic liquids, density functional methods, solubility, dielectric constant