Advertisement

Recovery of ionic liquids from methanol by pervaporation with polydimethylsiloxane membrane

  • Zhe Yang
  • Shurong Gao
  • Zhongqi Cao
  • Xiaochun Chen
  • Guangren YuEmail author
Original Paper
  • 4 Downloads

Abstract

Pervaporation (PV) is a new membrane technology for the separation of liquid mixtures and has many advantages, such as high efficiency, low energy consumption, simple process and convenient operation. In this work, we investigated the recovery (separation) of ionic liquids (ILs) from methanol by PV with polydimethylsiloxane (PDMS) membrane for the first time. PDMS membrane was prepared using polyvinylidene fluoride (PVDF) membrane with sponge-like holes as base membrane. Five ILs were synthesized, i.e., 1,3-dimethylimidazolium dimethylphosphate ([MMIM][DMP]), 1-ethyl-3-methylimidazolium diethylphosphate ([EMIM][DEP]), 1-butyl-3-methylimidazolium dibutylphosphate ([BMIM][DBP], 1-butyl-3-methylimidazolium cholorate ([BMIM][Cl]), and 1-ethyl-3-methylimidazolium tetrafluoroborate ([EMIM][BF4]). The influences of temperature, IL concentration, and IL specifies were investigated. It is observed that ILs do not penetrate through PDMS membrane. The flux increases along with temperature while decreases along with IL concentration in feed. Also, the flux depends on ILs species, and decreases following the order [EMIM][BF4] > [BMIM][DBP] > [BMIM][Cl] > [EMIM][DEP] > [MMIM][DMP]. A stable flux of 1666–1746 g m−2 h−1 was observed in a continuous running of 100 h, showing that PDMS membrane has a good stability for recovery of ILs from methanol. This work shows the PV with PDMS membrane is a good new method for recovering ILs from organic solvents.

Keywords

Recovery Ionic liquid Methanol Pervaporation PDMS 

Notes

Acknowledgements

This work was financially supported by National Natural Science Foundation of China (21878010).

Supplementary material

11696_2019_971_MOESM1_ESM.docx (20 kb)
Supplementary material 1 (DOCX 20 kb)

References

  1. Bakhshi A, Mohammadi T, Aroujalian A (2008) Pervaporation separation of binary and ternary mixtures with polydimethylsiloxane membranes. J Appl Polym Sci 107:1777–1782CrossRefGoogle Scholar
  2. Cai F, Wu X, Chen C, Chen X, Asumana C, Haque MR, Yu G (2013) Isobaric vapor–liquid equilibrium for methanol + dimethyl carbonate + phosphoric-based ionic liquids. Fluid Phase Equilib 352:47–53CrossRefGoogle Scholar
  3. Calvar N, González B, Cómez E, Domínguez Á (2006) Vapor-liquid equilibria for the ternary system ethanol + water + 1-butyl-3-methylimidazolium chloride and the corresponding binary systems at 101.3 kPa. J Chem Eng Data 51:2178–2181CrossRefGoogle Scholar
  4. Cao J, Yu G, Chen X, Abdeltawab AA, Al-Enizi AM (2017) Determination of vapor–liquid equilibrium of methyl acetate + methanol + 1-alkyl-3-methylimidazolium dialkylphosphates at 101.3 kPa. J Chem Eng Data 62:816–824CrossRefGoogle Scholar
  5. Castro MC, Arce A, Soto A, Dodríguze H (2016) Thermophysical characterization of the mixtures of the ionic liquid 1-ethyl-3-methylimidazolium acetate with 1-propanol or 2-propanol. J Chem Eng Data 61:2299–2310CrossRefGoogle Scholar
  6. Chen X, Cai F, Wu X, Asumana C, Yu G (2013) Isobaric vapor–liquid equilibrium for methanol + dimethyl carbonate + 1-butyl-3-methylimidazolium dibutylphosphate. J Chem Eng Data 58:1186–1192CrossRefGoogle Scholar
  7. Chen X, Yang B, Abdeltawab AA, Al-Deyab SS, Yu G, Yong X (2015) Isobaric vapor–liquid equilibrium for acetone + methanol + phosphate ionic liquids. J Chem Eng Data 60:612–620CrossRefGoogle Scholar
  8. Dai C, Lei Z, Xi X, Zhu J, Chen B (2014) Extractive distillation with a mixture of organic solvent and ionic liquid as entrainer. Ind Eng Chem Res 53:15786–15791CrossRefGoogle Scholar
  9. Dhanalakshmi J, Sai PST, Balakrishnan AR (2014) Effect of bivalent cation Inorganic salts on isobaric vapor–liquid equilibrium of methyl acetate–methanol system. Fluid Phase Equilib 379:112–119CrossRefGoogle Scholar
  10. Hashitani M, Hirata M (1969) Salt effect in vapor–liquid equilibrium: acetic ester–alcohol with potassium acetate and zinc chloride. J Chem Eng Jpn 2:149–152CrossRefGoogle Scholar
  11. Huang K, Wu R, Cao Y, Li H, Wang J (2013) Recycling and reuse of ionic liquid in homogeneous cellulose acetylation. Chin J Chem Eng 21(5):577–584CrossRefGoogle Scholar
  12. Jork C, Seiler M, Beste Y, Arlt W (2004) Influence of ionic liquids on the phase behavior of aqueous azeotropic systems. J Chem Eng Data 49:852–857CrossRefGoogle Scholar
  13. Lei Z, Chen B, Ding Z (2005) Special distillation processes. Elsevier, AmsterdamGoogle Scholar
  14. Lei Z, Chen B, Li C, Liu H (2008) Predictive molecular thermodynamic models for liquids, solid salts, polymers, and ionic liquids. Chem Rev 108:1419–1455CrossRefGoogle Scholar
  15. Lei Z, Li C, Chen B (2013) Extractive distillation: a review. Sep Purif Rev 32:121–213CrossRefGoogle Scholar
  16. Li Q, Cao L, Sun X, Li L, Zhang Y (2013) Isobraic vapor-liquid equilibrium for methyl acetate-methanol-1-ethyl-3-methylimidazolium tetrafluoroborate system. Petrochem Technol 42(6):636–640Google Scholar
  17. Mai NL, Ahn K, Koo YM (2014) Methods for recovery of ionic liquids—a review. Process Biochem 49:872–881CrossRefGoogle Scholar
  18. Matsuda H, Liebert V, Tochigi K, Gmehling J (2013) Influence of sulfate-based anion ionic liquids on the separation fFactor of the binary azeotropic system acetone + methanol. Fluid Phase Equilib 340:27–30CrossRefGoogle Scholar
  19. Nieuwoudt I, Van Dyk B (2000) Separation of methanol and methyl acetate from mixtures thereof by extractive distillation. WO Patent No. WO 2000044695 A1Google Scholar
  20. Nieuwoudt I, Van Dyk B (2002) Separation of components from methanol mixtures by extractive distillation. U.S. Patent No. US 6383343 B1Google Scholar
  21. Orchillés AV, Miguel PJ, Vercher E, Martínez-Andreu A (2007a) Ionic liquids as entrainers in extractive distillation: isobaric vapor–liquid equilibria for acetone + methanol + 1-ethyl-3-methylimidazolium trifluoromethanesulfonate. J Chem Eng Data 52:141–147CrossRefGoogle Scholar
  22. Orchillés AV, Miguel PJ, Vercher E, Martínez-Andreu A (2007b) Isobaric vapor-liquid equilibria for methyl acetate + methanol +1-ethyl-3-methylimidazolium trifluoromethanesulfonate at 100 kPa. J Chem Eng Data 52:915–920CrossRefGoogle Scholar
  23. Pereior AB, Rodríguez A (2008) Azeotrope-breaking using [BMIM][MeSO4] ionic liquid in an extraction column. Sep Purif Technol 62:733–738CrossRefGoogle Scholar
  24. Pereior AB, Rodríguez A (2009) Separation of ethanol-heptane azeotropic mixtures by solvent extraction with an ionic liquid. Ind Eng Chem Res 48:1579–1585CrossRefGoogle Scholar
  25. Pereior AB, Araújo JMM, Esperanca JMSS, Marrucho IM, Rebelo LPN (2012) Ionic liquids in separations of azeotropic systems—a review. J Chem Thermodynamics 46:2–28CrossRefGoogle Scholar
  26. Seiler M, Jork C, Schneider W, Arlt W (2002) Ionic liquids and hyperbranched polymers-promising new classes of selective entrainers for extractive distillation. In: Proceedings of the international conference on distillation and absorption 2002Google Scholar
  27. Seiler M, Jork C, Kavarnou A, Arlt W, Hirsch R (2004) Separation of azeotropic mixtures using hyperbranched polymers or ionic liquids. AIChE J 50:2439–2454CrossRefGoogle Scholar
  28. Sun J, Shi J, Konda NVSNM, Campos D, Liu D, Nemser S, Shamshina J, Dutta T, Berton P, Gurau G, Rogers RD, Simmons BA, Singh S (2017) Efficent dehydration and recovery of ionic liquid after lignocellulosic processing using pervaporation. Biotechnol Biofuels 10:154–168CrossRefGoogle Scholar
  29. Topphoff M, Jörn Kiepe J, Gmehling J (2001) Effects of lithium nitrate on the vapor–liquid equilibria of methyl acetate + methanol and ethyl acetate + ethanol. J Chem Eng Data 46:1333–1337CrossRefGoogle Scholar
  30. Yu G, Zhang L, Alhumaydhi IA, Abdeltawab AA, Bagabas AA, Al-Megren HA, Al-Deyab SS, Chen X (2015) Separation of propylene and propane by alkylimidazolium thiocyanate ionic liquids with Cu + salt. Sep Purif Technol 156:356–362CrossRefGoogle Scholar
  31. Yu G, Fan S, Chen X, Abdeltawab AA, Al-Deyab SS (2016) CO2 absorption by binary mixture of ionic liquids-monoethanolamine at lower pressure. Int J Greenh Gas Control 44:52–58CrossRefGoogle Scholar
  32. Zhang Z, Li W, Jia P (2013) Method for separating methyl acetate–methanol mixture by mixed extractant. China Patent No. CN 103172491 AGoogle Scholar
  33. Zhang Z, Hu A, Zhang T, Zhang Q, Sun M, Sun D, Li W (2015) Separation of methyl acetate + methanol azeotropic mixture using ionic liquids as entrainers. Fluid Phase Equilib 401:1–8CrossRefGoogle Scholar

Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2019

Authors and Affiliations

  • Zhe Yang
    • 1
    • 2
  • Shurong Gao
    • 1
    • 3
  • Zhongqi Cao
    • 1
  • Xiaochun Chen
    • 1
  • Guangren Yu
    • 1
    Email author
  1. 1.Beijing Key Laboratory of Membrane Science and Technology and College of Chemical EngineeringBeijing University of Chemical TechnologyBeijingChina
  2. 2.College of Chemical EngineeringHebei Normal University of Science & TechnologyQinhuangdaoChina
  3. 3.Research Center of Engineering ThermophysicsNorth China Electric Power UniversityBeijingChina

Personalised recommendations