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Title (Primary) Can ionic liquids exist in the soil environment? Effect of quaternary ammonium cations on glyphosate sorption, mobility and toxicity in the selected herbicidal ionic liquids
Author Parus, A.; Zdebelak, O.; Ciesielski, T.; Szumski, R.; Woźniak-Karczewska, M.; Framski, G.; Baranowski, D.; Niemczak, M.; Zembrzuska, J.; Cajthaml, T.; Heipieper, H.J.; Chrzanowski, Ł.
Journal Journal of Molecular Liquids
Year 2023
Department ISOBIO; UBT
Volume 370
Page From art. 120981
Language englisch
Topic T7 Bioeconomy
Keywords Ionic bond energy; Ion integrity; Phytotoxicity; Sorption isotherm; Synthesis; Toxicity
Abstract

Ionic liquids (ILs) are described as low-impact green chemicals in which the cation can influence the properties of the anion through ion pair formation. We decided to see how stable ILs are in the soil environment. Herbicidal ILs consisting of hydrophilic glyphosate [Glyph] paired with hydrophilic choline [Chol], hydrophobic C12 alkyl modified choline [C12Chol] and hydrophobic quaternary ammonium cation [C16TMA] were synthesized. The calculated interaction energies between ions (75.9–88.9 kcal/mol) were typical for ILs. The results showed independent sorption of cations and anions and no statistical effect of cations on anion sorption. Hydrophobic [C16TMA], [C12Chol] cations followed 99 % adsorption, and hydrophilic [Chol] revealed 42–45 % adsorption. The Freundlich constants were [C16TMA] Kf≈4000 > [C12Chol] Kf≈3000 > [Chol] Kf≈3 (mg1-1/n L1/n g-1). The preferential sorption of hydrophobic cations was also visible during leaching experiments and resembles the behavior of cationic surfactants. [Glyph] sorption was higher in organic-rich agricultural soil (approx. 45 %) compared to reference OECD soil (30 %), and the Kf values were constant, regardless of the presence of cations. The lack of ionic pair integrity was also visualized by the toxicity and phytotoxicity results. In the soil environment, ILs are a mixture of independent cations and anions rather than a novel emerging contaminant.

Persistent UFZ Identifier https://www.ufz.de/index.php?en=20939&ufzPublicationIdentifier=26925
Parus, A., Zdebelak, O., Ciesielski, T., Szumski, R., Woźniak-Karczewska, M., Framski, G., Baranowski, D., Niemczak, M., Zembrzuska, J., Cajthaml, T., Heipieper, H.J., Chrzanowski, Ł. (2023):
Can ionic liquids exist in the soil environment? Effect of quaternary ammonium cations on glyphosate sorption, mobility and toxicity in the selected herbicidal ionic liquids
J. Mol. Liq. 370 , art. 120981