Experimental measurements of mutual solubility of cyclohexanone, cyclohexene and ionic liquid

  • Valeriy Zhuchkov
  • Alla Frolkova
  • Sergey Nazanskiy
Original Paper
  • 14 Downloads

Abstract

This work presents new experimental liquid–liquid equilibrium data for four ternary systems, containing cyclohexanone, cyclohexene and ionic liquids (1-butyl-3-methylimidazolium hexafluorophosphate, 1-butyl-3-methylimidazolium tetrafluoroborate, triethylammonium trifluoromethanesulfonate, 1-ethyl-3-methylimidazolium trifluoromethanesulfonate) at temperature 296.15 K and at atmospheric pressure. Compositions of ternary liquid mixtures were determined using refractometric methods. It was shown that 1-ethyl-3-methylimidazolium trifluoromethanesulfonate and 1-butyl-3-methylimidazolium hexafluorophosphate containing imidazole cations can be considered as solvent for oxidation of cyclohexene to cyclohexanone.

Keywords

Cyclohexanone Cyclohexene Ionic liquid Liquid–liquid equilibrium Binodal curve Refractometric analysis 

List of symbols

K

Coefficient of distribution of the component between layers

n

Refractive index

x

Weight fraction of the component

Subscripts

CYHAONE

For the cyclohexanone weight fraction and distribution coefficient

11

Cyclohexanone in upper layer

33

Ionic liquid in lower layer

Superscript

296.15

Temperature of the refractive index measurements

Notes

Acknowledgements

The work was carried out under support of the Russian Science Foundation 16-19-10632.

References

  1. ALDRICH Chemistry (2012–2014) SIGMA-ALDRICHGoogle Scholar
  2. Domańska U, Karpińska M, Wlazło M (2016) Separation of hex-1-ene/hexane and cyclohexene/cyclohexane compounds with [EMIM]-based ionic liquids. Fluid Phase Equilib 427:421–428.  https://doi.org/10.1016/j.fluid.2016.08.008 CrossRefGoogle Scholar
  3. Elvira O, Greiner C, Inoguchi Y (2016) Cyclohexanol and cyclohexanone. Chemical economics handbook. Stanford Research Institute, California, USAGoogle Scholar
  4. Frolkova AV, Balbenov SA, Frolkova AK, Akishina AA (2015a) Phase equilibrium in the system water-acetonitrile-cyclohexene-cyclohexanone. Russ Chem Bull 64(10):2330–2336.  https://doi.org/10.1007/S11172-015-1160-7 CrossRefGoogle Scholar
  5. Frolkova AK, Zhuchkov VI, Rum’eantsev PG (2015b) Ionic liquids as separating agents in extractive rectification. Chem Eng Res Des 99:215–219.  https://doi.org/10.1016/j.cherd.2015.06.004 CrossRefGoogle Scholar
  6. Frolkova AV, Zakharova DS, Frolkova AK, Balbenov SA (2016) Liquid-liquid and liquid–liquid–liquid equilibrium for ternary system water-acetonitrile-cyclohexene at 298.15 K. Fluid Phase Equilib 408:10–14.  https://doi.org/10.1016/j.fluid.2015.06.039 CrossRefGoogle Scholar
  7. Ghanadzadeh H, Ghanadzadeh A, Bahrpaima KH, Saadat S (2008) (Liquid + liquid) equilibria of (water + propionic acid + 2-ethyl-1-hexanol): experimental data and correlation. J Chem Thermodyn 40:879–884.  https://doi.org/10.1016/j.jct.2008.01.001 CrossRefGoogle Scholar
  8. Ghanadzadeh H, Ghanadzadeh A, Sangashekan M (2013) Tie-line data for the aqueous solutions of phenol with organic solvents at T = 298.2. K J Chem Thermodyn 58:142–148.  https://doi.org/10.1016/j.jct.2012.10.028 CrossRefGoogle Scholar
  9. Kuklin S, Maximov A, Zolotukhina A et al (2016) New approach for highly selective hydrogenation of phenol to cyclohexanone: combination of rhodium nanoparticles and cyclodextrins. J Cata Commun 73:63–68.  https://doi.org/10.1016/j.catcom.2015.10.005 CrossRefGoogle Scholar
  10. Marciniak A (2010) Influence of cation and anion structure of the ionic liquid on extraction processes based on activity coefficients at infinite dilution. A review. Fluid Phase Equilib 294:213–233.  https://doi.org/10.1016/j.fluid.2009.12.025 CrossRefGoogle Scholar
  11. Martynov IV, Efremov GE, Temkin ON (2017) Kinetic isotope effects in oxidation reaction of C2H4 and C2D4 by p-benzoquinone in the Pd2+–HClO4–CH3CN–H2O system. Russ Chem Bull 66(5):922–923.  https://doi.org/10.1007/s11172-017-1830-8 CrossRefGoogle Scholar
  12. Namboodiri V, Varma RS, Sahle-Demessie E, Pillai U (2002) Selective oxidation of styrene to acetophenone in the presence of ionic liquids. Green Chem 4:170–173.  https://doi.org/10.1039/b109534j CrossRefGoogle Scholar
  13. Othmer DF, Tobias PE (1942) Tie line correlation. Ind Eng Chem 34:690–692CrossRefGoogle Scholar
  14. Pei Y, Wang Q, Gong X et al (2015) Distribution of cyclohexanol and cyclohexanone between water and cyclohexane. J Fluid Phase Equilib. 394:129–139.  https://doi.org/10.1016/j.fluid.2015.02.029 CrossRefGoogle Scholar
  15. Ribeiro A, Martins L, Hazra S et al (2015) Catalytic oxidation of cyclohexane with hydrogen peroxide and a tetracopper (II) complex in an ionic liquid. J Comptes Rendus Chimie. 18(7):758–765.  https://doi.org/10.1016/j.crci.2015.03.018 CrossRefGoogle Scholar
  16. Schuur B (2015) Selection and design of ionic liquids as solvents in extractive distillation and extraction processes. Chem Pap 69(2):245–253.  https://doi.org/10.1515/chempap-2015-0016 CrossRefGoogle Scholar
  17. Temkin ON, Bruk LG, Zakharova DS, Odintsov KY et al (2010) Kinetics of cyclohexene oxidation by p-quinones in aqueous-organic solutions of cationic Palladium(II) Complexes. Kinet Catal 51(5):691–703.  https://doi.org/10.1134/S0023158410050101 CrossRefGoogle Scholar
  18. Welton T (2004) Ionic liquids in catalysis. Coord Chem Rev 248:2459–2477.  https://doi.org/10.1016/j.ccr.2004.04.015 CrossRefGoogle Scholar
  19. Zhuchkov VI, Rumyancev PG, Reshetov SA et al (2011) Experimental research of extractive distillation in the presence of ionic liquid. Vestnik MITHT VI(3):44–50 (in Russian) Google Scholar

Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2018

Authors and Affiliations

  • Valeriy Zhuchkov
    • 1
  • Alla Frolkova
    • 1
  • Sergey Nazanskiy
    • 1
  1. 1.Department of Chemistry and Technology of Basic Organic Synthesis, Institute of Fine Chemical TechnologyMoscow Technological UniversityMoscowRussia

Personalised recommendations