Sustainable Phenylalanine-Derived SAILs for Solubilization of Polycyclic Aromatic Hydrocarbons

Illia V Kapitanov, Surya M Sudheer, Toshikee Yadav, Kallol K Ghosh, Nicholas Gathergood, Vijai K Gupta, Yevgen Karpichev

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)
18 Downloads (Pure)

Abstract

The solubilization capacity of a series of sustainable phenylalanine-derived surface-active ionic liquids (SAILs) was evaluated towards polycyclic aromatic hydrocarbons-naphthalene, anthracene and pyrene. The key physico-chemical parameters of the studied systems (critical micelle concentration, spectral properties, solubilization parameters) were determined, analyzed and compared with conventional cationic surfactant, CTABr. For all studied PAH solubilization capacity increases with extension of alkyl chain length of PyPheOCn SAILs reaching the values comparable to CTABr for SAILs with n = 10-12. A remarkable advantage of the phenylalanine-derived SAILs PyPheOCn and PyPheNHCn is a possibility to cleave enzymatically ester and/or amide bonds under mild conditions, to separate polycyclic aromatic hydrocarbons in situ. A series of immobilized enzymes was tested to determine the most suitable candidates for tunable decomposition of SAILs. The decomposition pathway could be adjusted depending on the choice of the enzyme system, reaction conditions, and selection of SAILs type. The evaluated systems can provide selective cleavage of the ester and amide bond and help to choose the optimal decomposition method of SAILs for enzymatic recycling of SAILs transformation products or as a pretreatment towards biological mineralization. The concept of a possible practical application of studied systems for PAHs solubilization/separation was also discussed focusing on sustainability and a green chemistry approach.
Original languageEnglish
Article number4185
JournalMolecules (Basel, Switzerland)
Volume28
Issue number10
Early online date19 May 2023
DOIs
Publication statusPrint publication - May 2023

Keywords

  • Solubilization
  • Sustainability
  • Biodegradability
  • polycyclic aromatic hydrocarbons (PAHs)
  • Enzymatic Decomposition
  • Surface-active Ionic Liquids (Sails)
  • biodegradability
  • solubilization
  • enzymatic decomposition
  • surface-active ionic liquids (SAILs)
  • sustainability

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