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

Researchers

  1. Isabel Albrecht

Publications

  1. Proxies
  2. Visualization of the Plasma Frequency by means of a Particle Simulation using a Normalized Periodic Model
  3. A Wavelet Packet Algorithm for Online Detection of Pantograph Vibrations
  4. Active and semi-supervised data domain description
  5. Modelling and implementation of an Order2Cash Process in distributed systems
  6. Preventive Diagnostics for cardiovascular diseases based on probabilistic methods and description logic
  7. Top-down contingent attentional capture during feed-forward visual processing
  8. Robust approximate fixed-time tracking control for uncertain robot manipulators
  9. Other spaces
  10. Distributable Modular Software Framework for Manufacturing Systems
  11. The Open Anchoring Quest Dataset: Anchored Estimates from 96 Studies on Anchoring Effects
  12. Developing a Complex Portrait of Content Teaching for Multilingual Learners via Nonlinear Theoretical Understandings
  13. Learning and Re-learning from net- based cooperative learning discourses
  14. Combining flatness based feedforward action with a fractional PI regulator to control the intake valve engine
  15. Learning in the "Third Space"
  16. Reciprocal Relationships Between Dispositional Optimism and Work Experiences
  17. Robustness of coherent sets computations
  18. Generative 3D reconstruction of Ti-6Al-4V basketweave microstructures by optimization of differentiable microstructural descriptors
  19. Intraspecific trait variation increases species diversity in a trait-based grassland model
  20. Group formation in computer-supported collaborative learning
  21. Tree species and genetic diversity increase productivity via functional diversity and trophic feedbacks
  22. Differences in the sophistication of Value-based Management
  23. The Augmented Theorist - Toward Automated Knowledge Extraction from Conceptual Models
  24. Global fern and lycophyte richness explained: How regional and local factors shape plot richness
  25. Function, flexibility, and responsibility
  26. Enterprise Architecture Management Support for Digital Transformation Projects in Very Large Enterprises
  27. Visual-Inertial Navigation Systems and Technologies
  28. Erroneous examples as desirable difficulty
  29. Theme zones in English media discourse
  30. Error handling in office work with computers
  31. Intraindividual variability in identity centrality
  32. Analyzing Talk and Text II: Thematic Analysis
  33. I share because of who I am: values, identities, norms, and attitudes explain sharing intentions
  34. Data quality assessment framework for critical raw materials. The case of cobalt
  35. Analysing clickstream data
  36. Managing (in) times of uncertainty
  37. Introduction: The representative turn in EU Studies
  38. The 1986 Principles Relating to Remote Sensing of the Earth from Outer Space (RS Princi­ples)
  39. Fluorometer controlled apparatus designed for long-duration algal-feeding experiments and environmental effect studies with mussels