An advanced approach for the recovery of acetic acid from its aqueous media: deep eutectic liquids versus ionic liquids

  • Selin ŞahinEmail author
  • Ebru Kurtulbaş
Original Article


Green chemistry era forces scientists to develop and apply new media in recovery of high-added value materials. It is interesting to utilize deep eutectic liquids (DELs), which have advantages of biodegradability and very low toxicity and ease of use, in separating these fine materials from a complex environment. DELs have been specially designed and used for the extraction of recovery of acetic acid (AA) from its aqueous solutions. Two DELs containing the same hydrogen bond donor-HBD (glycerol) and two different hydrogen bond acceptor-HBA (a quaternary ammonium salt and an amine-based) have been designed with a molar ratio of 1:2. The tailor-designed extractants were diluted with diethyl adipate (DEA), diethyl malonate (DEM), and diethyl succinate (DES), respectively. Extraction efficiency of the diluents has been increased more than 4 times. To compare the results with that of the ionic liquid (IL), 1-hexyl-3-methylimidazolium bromide has been used in the same organic solvents. Efficiencies of the DELs have surpassed 1.4 to 4 times over the IL.

Graphical abstract


Extraction Reactive extraction Ionic liquids Deep eutectic liquid Green chemistry Carboxylic acid 


Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.


  1. 1.
    Zhang Q, De Oliveira VK, Royer S, Jérôme F (2012) Deep eutectic solvents: syntheses, properties and applications. Chem Soc Rev 41:7108. CrossRefGoogle Scholar
  2. 2.
    Tang B, Zhang H, Row KH (2015) Application of deep eutectic solvents in the extraction and separation of target compounds from various samples. J Sep Sci 38:1053–1064. CrossRefGoogle Scholar
  3. 3.
    Radošević K, Cvjetko Bubalo M, Gaurina Srček V et al (2015) Evaluation of toxicity and biodegradability of choline chloride based deep eutectic solvents. Ecotoxicol Environ Saf 112:46–53. CrossRefGoogle Scholar
  4. 4.
    Smith EL, Abbott AP, Ryder KS (2014) Deep eutectic solvents (DESs) and their applications. Chem Rev 114:11060–11082. CrossRefGoogle Scholar
  5. 5.
    Paiva A, Craveiro R, Aroso I et al (2014) Natural deep eutectic solvents – solvents for the 21st century. ACS Sustain Chem Eng 2:1063–1071. CrossRefGoogle Scholar
  6. 6.
    Andrew P. Abbott *, David Boothby, Glen Capper, et al (2004) Deep eutectic solvents formed between choline chloride and carboxylic Acids: Versatile Alternatives to Ionic Liquids. doi: CrossRefGoogle Scholar
  7. 7.
    Durand E, Lecomte J, Villeneuve P (2013) Deep eutectic solvents: synthesis, application, and focus on lipase-catalyzed reactions. Eur J Lipid Sci Technol 115:379–385. CrossRefGoogle Scholar
  8. 8.
    Hong YK, Hong WH, Han DH (2001) Application of reactive extraction to recovery of carboxylic acids. Biotechnol Bioprocess Eng 6:386–394. CrossRefGoogle Scholar
  9. 9.
    Cas -Caval, D, Lenut -A Kloetzer † (2011) Influence of organic phase polarity on interfacial mechanism and efficiency of reactive extraction of acetic acid with tri-n-octylamine. J Chem Eng Data 56:2521–2526. doi: CrossRefGoogle Scholar
  10. 10.
    Hong YK, Hong WH (2005) Removal of acetic acid from aqueous solutions containing succinic acid and acetic acid by tri-n-octylamine. Sep Purif Technol 42:151–157. CrossRefGoogle Scholar
  11. 11.
    Mahfud FH, van Geel FP, Venderbosch RH, Heeres HJ (2008) Acetic acid recovery from fast pyrolysis oil. An exploratory study on liquid-liquid reactive extraction using aliphatic tertiary amines. Sep Sci Technol 43:3056–3074. CrossRefGoogle Scholar
  12. 12.
    Rasrendra CB, Girisuta B, van de Bovenkamp HH et al (2011) Recovery of acetic acid from an aqueous pyrolysis oil phase by reactive extraction using tri-n-octylamine. Chem Eng J 176–177:244–252. CrossRefGoogle Scholar
  13. 13.
    Yang G, Jahan MS, Ahsan L, Zheng L, Ni Y (2013) Recovery of acetic acid from pre-hydrolysis liquor of hardwood Kraft-based dissolving pulp production process by reactive extraction with triisooctylamine. Bioresour Technol 138:253–258. CrossRefGoogle Scholar
  14. 14.
    Li X, Kersten SRA, Schuur B (2017) Extraction of acetic acid, glycolaldehyde and acetol from aqueous solutions mimicking pyrolysis oil cuts using ionic liquids. Sep Purif Technol 175:498–505. CrossRefGoogle Scholar
  15. 15.
    Duan L, Dou L-L, Guo L, et al Comprehensive evaluation of deep eutectic solvents in extraction of bioactive natural products. doi: CrossRefGoogle Scholar
  16. 16.
    Uslu H (2009) Reactive extraction of formic acid by using tri octyl amine (TOA). Sep Sci Technol 44:1784–1798. CrossRefGoogle Scholar
  17. 17.
    Uslu H, I ˙ Smail Kırbas¸larkırbas¸lar S¸, Wasewar KL Reactive extraction of levulinic acid by amberlite LA-2 extractant. doi: CrossRefGoogle Scholar
  18. 18.
    Kırbaşlar Şİ, Şahin S, Bilgin M (2006) (liquid + liquid) equilibria of (water + propionic acid + alcohol) ternary systems. J Chem Thermodyn 38:1503–1509. CrossRefGoogle Scholar
  19. 19.
    Wasewar KL, Heesink ABM, Versteeg GF, Pangarkar VG (2002) Reactive extraction of lactic acid using alamine 336 in MIBK: equilibria and kinetics. J Biotechnol 97:59–68. CrossRefGoogle Scholar
  20. 20.
    Ahin S, Bayazit S, Bilgin M, et al Investigation of formic acid separation from aqueous solution by reactive extraction: effects of extractant and diluent. doi: CrossRefGoogle Scholar
  21. 21.
    Uslu H, Datta D (2015) Experimental and theoretical investigations on the reactive extraction of itaconic (2-methylidenebutanedioic) acid using trioctylamine (N,N-dioctyloctan-1-amine). doi: CrossRefGoogle Scholar
  22. 22.
    Deetlefs M, Seddon KR (2009) Assessing the greenness of some typical laboratory ionic liquid preparations. CrossRefGoogle Scholar
  23. 23.
    Romero A, Santos A, Tojo J, Rodríguez A (2008) Toxicity and biodegradability of imidazolium ionic liquids. J Hazard Mater 151:268–273. CrossRefGoogle Scholar
  24. 24.
    Plechkova NV, Seddon KR (2008) Applications of ionic liquids in the chemical industry. Chem Soc Rev 37:123–150. CrossRefGoogle Scholar
  25. 25.
    Cvjetko Bubalo M, Radošević K, Radojčić Redovniković I et al (2014) A brief overview of the potential environmental hazards of ionic liquids. Ecotoxicol Environ Saf 99:1–12. CrossRefGoogle Scholar
  26. 26.
    Şahin S, Elhussein EAA, Bilgin M et al (2018) Investigation of extractive interaction between ionic liquids and carbamazepine. J Mol Liq 268:523–528. CrossRefGoogle Scholar
  27. 27.
    AlOmar MK, Hayyan M, Alsaadi MA et al (2016) Glycerol-based deep eutectic solvents: physical properties. J Mol Liq 215:98–103. CrossRefGoogle Scholar
  28. 28.
    Infrared Spectroscopy Absorption Table - Chemistry LibreTextsGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2020

Authors and Affiliations

  1. 1.Chemical Engineering DepartmentIstanbul University-CerrahpaşaIstanbulTurkey

Personalised recommendations