Tetrabutylammonium prolinate-based ionic liquids: A combined asymmetric catalysis, antimicrobial toxicity and biodegradation assessment

Research output: Journal contributionsJournal articlesResearchpeer-review

Authors

  • Nadege Ferlin
  • Matthieu Courty
  • Albert Nguyen Van Nhien
  • Sylvain Gatard
  • Milan Pour
  • Bríd Quilty
  • Mukund Ghavre
  • A. Haiß
  • K. Kümmerer
  • Nicholas Gathergood
  • Sandrine Bouquillon

Chiral ionic liquids (CILs) tetrabutylammonium-(S)-prolinate, tetrabutylammonium-(R)-prolinate and tetrabutylammonium trans-4-hydroxy-(S)- prolinate were investigated as chiral additives in the Pd-catalyzed enantioselective hydrogenation of α,β-unsaturated ketones. These CILs were easily prepared in one step from the aminoacid and tetrabutylammonium hydroxide and characterized (NMR, IR, optical rotation, elemental analysis, DSC, viscosity, decomposition temperature). The research strategy was to assess the antimicrobial toxicity (>20 strains) and biodegradability (OECD 301D) of the CILs at the same time as undertaking the asymmetric catalysis study. The Pd-catalyzed enantioselective hydrogenation of the carbon-carbon double bond of α,β-unsaturated ketones under mild conditions (room temperature, 1 atm of H 2) in different solvents with CILs present. The best results were obtained in i-PrOH after 18 hours of reaction with a i-PrOH/IL ratio of 5. While all three CILs have low antimicrobial toxicity to a wide range of bacteria and fungi, tetrabutylammonium-(S)-prolinate, tetrabutylammonium-(R)-prolinate and tetrabutylammonium trans-4-hydroxy-(S)-prolinate did not pass the Closed Bottle biodegradation test.

Original languageEnglish
JournalRSC Advances
Volume3
Issue number48
Pages (from-to)26241-26251
Number of pages11
DOIs
Publication statusPublished - 28.12.2013

Bibliographical note

This work was supported by the Fondation du Site Paris Reims
(post doctoral fellowship for Nad`ege Ferlin) and the FEDER for
material funds. This work was also supported by Enterprise
Ireland (EI TD/07/328, Ian Beadham and Mukund Ghave). The
antibacterial and antifungal screening was supported by the
Czech Science Foundation (project no. P207/10/2048) (Milan
Pour, 20 Strains).

    Research areas

  • Chemistry - Asymmetric catalysis, Carbon-carbon double bonds, Chiral ionic liquids, Closed bottle biodegradation tests, Decomposition temperature, Enantioselective hydrogenation, Tetrabutylammonium hydroxides, Unsaturated ketones

DOI

Recently viewed

Publications

  1. Using Multi-Label Classification for Improved Question Answering
  2. Towards a socio-cognitive approach to knowledge transfer
  3. The internal audience of external communications
  4. Vorräte - Schätzung des Fertigstellungsgrades bei der Percentage of Completion Methode
  5. Der Zentrale Runde Tisch der DDR: Wortprotokoll und Dokumente
  6. The Lüneburg Sustainable University Project in international comparison
  7. A multivariate, multilevel analysis of the relationship between cognitive abilities and scholastic achievement
  8. "There is no alternative"
  9. Conservatives are less accurate than liberals at recognizing false climate statements, and disinformation makes conservatives less discerning
  10. Wissenschaftliche Kommunikation im Netz 2013
  11. Techniques to Control Microbial Contaminants in Nonsterile Microalgae Cultivation
  12. Wie gesprochen werden?
  13. Modeling approach of thermal decomposition of salt-hydrates for heat storage systems
  14. Processability of Mg-Gd Powder via Friction Extrusion
  15. Lernende in der Hauptschule
  16. Does reference to COVID-19 improve climate change communication? Investigating the influence of emotions and uncertainty in persuasion messages
  17. Soziale und kulturelle Differenz
  18. Enterprise Integration
  19. The influence of teacher-trainings on in-service teachers’ expertise: a teacher-training-study on formative assessment in competency-oriented mathematics
  20. Error management or error prevention
  21. Coresets for Archetypal Analysis
  22. Branding the campus
  23. Notting Hill Gate 4 Basic
  24. Exhibiting Earth History
  25. Influence of three different balance shoes on EMG-activity during one-leg standing
  26. Who are the workers who never joined a union?
  27. Knowledge Graph Question Answering Leaderboard
  28. Alternatives to Organizational Downsizing
  29. Gab es wirklich eine Sintflut?
  30. Integration eines Open-Source-Lernmanagementsystems an der Medizinischen Fakultät der LMU München
  31. Transformations of pesticides in the atmosphere
  32. Gefühle, Affekte, Feminisierung
  33. Alex Adriaansens
  34. Multiple Glacial Refugia of the Low-Dispersal Ground Beetle Carabus irregularis:
  35. Virtuelles Ohr
  36. Demand response aggregators as institutional entrepreneurs in the European electricity market
  37. Scale-dependent effects of conspecific negative density dependence and immigration on biodiversity maintenance
  38. Strategisches Logistikmanagement
  39. Don't ignore the floor
  40. Gender Equality in Academia
  41. Sustainability Accounting and Reporting
  42. Modulating immune responses and inflammation
  43. Understanding and explaining populist radical right parties’ commitment to animal welfare in Western Europe