Skip to main content
Log in

Recovery of ionic liquids from methanol by pervaporation with polydimethylsiloxane membrane

  • Original Paper
  • Published:
Chemical Papers Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  • Bakhshi A, Mohammadi T, Aroujalian A (2008) Pervaporation separation of binary and ternary mixtures with polydimethylsiloxane membranes. J Appl Polym Sci 107:1777–1782

    Article  CAS  Google Scholar 

  • 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 352:47–53

    Article  CAS  Google Scholar 

  • 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 51:2178–2181

    Article  CAS  Google Scholar 

  • 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 62:816–824

    Article  CAS  Google Scholar 

  • 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 61:2299–2310

    Article  CAS  Google Scholar 

  • 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 58:1186–1192

    Article  CAS  Google Scholar 

  • 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 60:612–620

    Article  CAS  Google Scholar 

  • 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 53:15786–15791

    Article  CAS  Google Scholar 

  • 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 379:112–119

    Article  CAS  Google Scholar 

  • Hashitani M, Hirata M (1969) Salt effect in vapor–liquid equilibrium: acetic ester–alcohol with potassium acetate and zinc chloride. J Chem Eng Jpn 2:149–152

    Article  CAS  Google Scholar 

  • 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):577–584

    Article  Google Scholar 

  • 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 49:852–857

    Article  CAS  Google Scholar 

  • Lei Z, Chen B, Ding Z (2005) Special distillation processes. Elsevier, Amsterdam

    Google Scholar 

  • Lei Z, Chen B, Li C, Liu H (2008) Predictive molecular thermodynamic models for liquids, solid salts, polymers, and ionic liquids. Chem Rev 108:1419–1455

    Article  CAS  Google Scholar 

  • Lei Z, Li C, Chen B (2013) Extractive distillation: a review. Sep Purif Rev 32:121–213

    Article  Google Scholar 

  • 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):636–640

    CAS  Google Scholar 

  • Mai NL, Ahn K, Koo YM (2014) Methods for recovery of ionic liquids—a review. Process Biochem 49:872–881

    Article  CAS  Google Scholar 

  • 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 340:27–30

    Article  CAS  Google Scholar 

  • Nieuwoudt I, Van Dyk B (2000) Separation of methanol and methyl acetate from mixtures thereof by extractive distillation. WO Patent No. WO 2000044695 A1

  • Nieuwoudt I, Van Dyk B (2002) Separation of components from methanol mixtures by extractive distillation. U.S. Patent No. US 6383343 B1

  • 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 52:141–147

    Article  Google Scholar 

  • 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 52:915–920

    Article  Google Scholar 

  • Pereior AB, Rodríguez A (2008) Azeotrope-breaking using [BMIM][MeSO4] ionic liquid in an extraction column. Sep Purif Technol 62:733–738

    Article  Google Scholar 

  • Pereior AB, Rodríguez A (2009) Separation of ethanol-heptane azeotropic mixtures by solvent extraction with an ionic liquid. Ind Eng Chem Res 48:1579–1585

    Article  Google Scholar 

  • Pereior AB, Araújo JMM, Esperanca JMSS, Marrucho IM, Rebelo LPN (2012) Ionic liquids in separations of azeotropic systems—a review. J Chem Thermodynamics 46:2–28

    Article  Google Scholar 

  • 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 2002

  • Seiler M, Jork C, Kavarnou A, Arlt W, Hirsch R (2004) Separation of azeotropic mixtures using hyperbranched polymers or ionic liquids. AIChE J 50:2439–2454

    Article  CAS  Google Scholar 

  • 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 10:154–168

    Article  Google Scholar 

  • 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 46:1333–1337

    Article  CAS  Google Scholar 

  • 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 156:356–362

    Article  CAS  Google Scholar 

  • 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 44:52–58

    Article  CAS  Google Scholar 

  • Zhang Z, Li W, Jia P (2013) Method for separating methyl acetate–methanol mixture by mixed extractant. China Patent No. CN 103172491 A

  • 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 401:1–8

    Article  CAS  Google Scholar 

Download references

Acknowledgements

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

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Guangren Yu.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 20 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yang, Z., Gao, S., Cao, Z. et al. Recovery of ionic liquids from methanol by pervaporation with polydimethylsiloxane membrane. Chem. Pap. 74, 1331–1337 (2020). https://doi.org/10.1007/s11696-019-00971-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11696-019-00971-y

Keywords

Navigation