Identification of structure-biodegradability relationships for ionic liquids - clustering of a dataset based on structural similarity

Research output: Journal contributionsJournal articlesResearchpeer-review

Authors

Environmentally open applications as herbicides or active pharmaceutical ingredients are discussed for ionic liquids (ILs). Since most of the ILs are not readily biodegradable in the environment, they may persist there. To prevent the accumulation of persistent and toxic ILs, both the cation and anion need to be designed to completely mineralise in the environment. Several studies summarised structure-biodegradability relationships (SBRs) and gained rules of thumb for ILs’ biodegradability based on the available literature data. However, no study systematically analysed a dataset using an in silico tool. Therefore, to identify SBRs a dataset on the ready biodegradability of 508 ILs was clustered according to IL similarity by using the software Canvas by Schrödinger. The biodegradability was divided into three classes (biodegradation rates 0-19%, 20-59% and ≥60%). The identified SBRs were compared with the available rules of thumb from the literature. The results show that the cholinium cation and its derivatives acetylcholine, betaine and carnitine are promising candidates for designing environmentally mineralising ILs if a good biodegradable anion is chosen. Imidazolium and phosphonium ILs should be avoided. For pyrrolidinium and quaternary ammonium compounds cations containing ester or carboxyl groups in side chains and alkylsulphate anions should be tested to close gaps in SBRs and possibly design a mineralising IL. Due to the limited data of morpholinium, 1,4-diazabicyclo[2.2.2]octanium (DABCO), piperidinium, prolinium, piperazinium and thiazolium ILs, SBRs could not be clearly identified. Further research is needed on whether structural adjustments according to the findings can increase the biodegradability of not yet fully degrading (20-59%) ILs.

Original languageEnglish
JournalGreen Chemistry
Volume25
Issue number22
Pages (from-to)9226-9250
Number of pages25
ISSN1463-9262
DOIs
Publication statusPublished - 29.09.2023

Bibliographical note

Funding Information:
We would like to thank the German Federal Ministry for the Environment, Nature Conservation, Nuclear Safety and Consumer Protection (BMUV) and the German Umweltbundesamt (UBA) for their support with the International Sustainable Chemistry Collaborative Centre (ISC3) activities. We thank our colleagues Stefanie Lorenz and Morten Suk for fruitful discussions on the biodegradability of ILs and on clustering compounds.

Publisher Copyright:
© 2023 The Royal Society of Chemistry.

DOI

Recently viewed

Publications

  1. Supporting the Development and Realization of Data-Driven Business Models with Enterprise Architecture Modeling and Management
  2. Making an Impression Through Openness
  3. Parameters Estimation of a Lotka-Volterra Model in an Application for Market Graphics Processing Units
  4. Mechanism of dynamic recrystallization and evolution of texture in the hot working domains of the processing map for Mg-4Al-2Ba-2Ca Alloy
  5. Understanding Low-Code Evolution, Adoption and Ecosystem for Software Development
  6. Don’t underestimate the problems of user centredness in software development projectsthere are many!?
  7. Meta-Image – a collaborative environment for the image discourse
  8. HR practices and ambidexterity in small- and medium-sized consulting firms: An exploratory multi-case study
  9. Linear free vibrations with uncertain initial conditions
  10. Metrics for Experimentation Programs: Categories, Benefits and Challenges
  11. Distributable Modular Software Framework for Manufacturing Systems
  12. Fallstudie
  13. A robust model predictive control using a feedforward structure for a hybrid hydraulic piezo actuator in camless internal combustion engines
  14. Likelihood-based panel cointegration test in the presence of a linear time trend and cross-sectional dependence
  15. Learner pragmatics at the discourse level: Staying “on topic” in a telecollaborative eTandem task
  16. Mindsets and reflection in teacher education for inclusive language classrooms
  17. Application of novel constrained friction processing method to produce fine grained biomedical Mg-Zn-Ca alloy
  18. Risk Aversion and Sorting into Public Sector Employment
  19. Can guided introspection help avoid rationalization of meat consumption?
  20. Photodegradation of micropollutants using V-UV/UV-C processes
  21. Dynamic Semantic Web Content for Museum Guides
  22. NIF4OGGD - NLP interchange format for open German governmental data
  23. Mapping water ecosystem services: Evaluating InVEST model predictions in data scarce regions
  24. Knowledge Spaces of Globalization
  25. sPlotOpen – An environmentally balanced, open-access, global dataset of vegetation plots
  26. A Model Based Feedforward Regulator Improving PI Control of an Ice-Clamping Device Activated by Thermoelectric Cooler
  27. A new magnesium alloy system
  28. Heterogenous activation of dynamic recrystallization and twinning during friction stir processing of a Cu-4Nb alloy
  29. Secret Agents