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

Anna Parus; Oskar Zdebelak; Tomasz Ciesielski; Radosław Szumski; Marta Woźniak-Karczewska; Grzegorz Framski; Daniel Baranowski; Michał Niemczak; Joanna Zembrzuska; Tomáš Cajthaml; Hermann J. Heipieper; Łukasz Chrzanowski

doi:10.1016/j.molliq.2022.120981

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Title

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

Authors

Anna Parus (WTCH) ^{[ 1 ][ 7.6 ][ P ]}
Oskar Zdebelak (WTCH) ^{[ 1 ][ S ]}
Tomasz Ciesielski (WTCH) ^{[ 1 ][ 7.6 ][ SzD ]}
Radosław Szumski (WTCH) ^{[ 1 ][ S ]}
Marta Woźniak-Karczewska (WTCH) ^{[ 1 ][ 7.6 ][ P ]}
Grzegorz Framski
Daniel Baranowski
Michał Niemczak (WTCH) ^{[ 1 ][ 7.6 ][ P ]}
Joanna Zembrzuska (WTCH) ^{[ 2 ][ 7.6 ][ P ]}
Tomáš Cajthaml
Hermann J. Heipieper
Łukasz Chrzanowski (WTCH) ^{[ 1 ][ 7.6 ][ P ]}

^{[ 1 ]} Instytut Technologii i Inżynierii Chemicznej, Wydział Technologii Chemicznej, Politechnika Poznańska | ^{[ 2 ]} Instytut Chemii i Elektrochemii Technicznej, Wydział Technologii Chemicznej, Politechnika Poznańska | ^{[ P ]} employee | ^{[ S ]} student | ^{[ SzD ]} doctoral school student

Scientific discipline (Law 2.0)

[7.6] Chemical sciences

Year of publication

2023

Published in

Journal of Molecular Liquids

Journal year: 2023 | Journal volume: vol. 370

Article type

scientific article

Publication language

english

Keywords

EN

Ionic bond energy
Ion integrity
Phytotoxicity
Sorption isotherm
Synthesis
Toxicity

Abstract

EN 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] Kf4000 > [C12Chol] Kf3000 > [Chol] Kf3 (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.

Pages (from - to)

120981-1 - 120981-12

DOI

10.1016/j.molliq.2022.120981

URL

https://www.sciencedirect.com/science/article/pii/S016773222202520X

Comments

Article number: 120981

License type

CC BY (attribution alone)

Ministry points / journal

100