Defined mechanochemical reductive dechlorination of 1,3,5-trichlorobenzene at room temperature in a ball mill

Research output: Journal contributionsJournal articlesResearch

Authors

1,3,5-Trichlorobenzene (TCB) is completely dechlorinated to benzene when treated with magnesium and n-butylamine at room temperature in a ball mill. A full mass balance is observed for its stepwise reductive dechlorination via the intermediates 1,3-dichlorobenzene (DCB) and monochlorobenzene (MCB). This mechanochemical (MC) reaction occurs due to ongoing, simultaneous comminution and mechanical activation of small particle size magnesium during milling. The base metal is utilized as the actual dechlorinating agent whereas n-butylamine as a hydrogen donor. A kinetic study reveals that consecutive and coupled one-pot Grignard-Zerewitinoff reactions occur: MC activated formations of intermediary Grignard components from 1,3,5-TCB, 1,3-DCB and MCB, take place each first, and then stepwise their protonation to DCB, MCB and benzene, respectively, by the amine, which reacts as a (weak) acid towards strong bases such as Grignard reagents. An appropriate reaction model comprising a corresponding set of rate equations (ordinary differential equations (ODEs) representing an initial value problem) could successfully be fitted to two data sets recorded for a representative model degradation reaction of 1,3,5-TCB at two different initial concentrations. The rate constants for the formation of the postulated intermediary Grignard components were computed, hence this method can readily be extended to determine Grignard formation rate constants in general as well. Results are in very good accordance to data recently reported for an analogous MC reductive dechlorination reaction of 1,3-DCB and correspond well, too, to other data previously reported elsewhere. In conclusion, MC reductive dechlorination employing base metals in combination with hydrogen donors can be applied as a promising non-combustion method to the environmentally friendly, defined and well characterized destruction of persistent organic pollutants (POPs) at room temperature.
Original languageEnglish
JournalFresenius Environmental Bulletin
Volume20
Issue number10a
Pages (from-to)2794-2805
Number of pages12
ISSN1018-4619
Publication statusPublished - 2011

    Research areas

  • Chemistry - 1,3,5-trichlorobenzene, Ball mill, Destruction, Grignard, Magnesium, Mechanochemistry, Non-combustion, Non-thermal, Persistent organic pollutants, Reductive dechlorination, Zerewitinoff

Recently viewed

Publications

  1. Attribution of Egoistic Versus Altruistic Motives to Acts of Helping
  2. Grenzarbeit in integrativer und grenzüberschreitender Forschung
  3. Similar factors underlie tree abundance in forests in native and alien ranges
  4. Public Value
  5. A leverage points perspective on Arctic Indigenous food systems research
  6. Identifying governance gaps among interlinked sustainability challenges
  7. Assessing participatory practices in community-based natural resource management: Experiences in community engagement from southern Africa
  8. On Knowing Too Much
  9. Leveraging Governance Performance to Enhance Climate Resilience
  10. An IAD framework analysis of minigrid institutions for sustainable rural electrification in East Africa
  11. Differences in isoprenoid-mediated energy dissipation pathways between coastal and interior Douglas-fir seedlings in response to drought
  12. Utilising learning analytics for study success
  13. Zur ‚Privatisierung‘ von gewaltsamem Protest
  14. Mentoring in schulischen Praxisphasen
  15. Discrete-Point Analysis of the Energy Demand of Primary versus Secondary Metal Production
  16. 2 Thessalonians as pseudepigraphic 'reading instruction' for 1 Thessalonians
  17. Effects of segregation of primary alloying elements on the creep response in magnesium alloys
  18. A path-centric account of action-oriented entrepreneurship training
  19. Understanding self-disclosure on social networking sites - a literature review
  20. Surveying the FAIRness of Annotation Tools: Difficult to find, difficult to reuse
  21. Rózsa Farkas
  22. Waving goodbye to conflict of laws? Recent developments in European Union consumer law
  23. Which Relationality? Whose Personhood?
  24. The roughness of neural networks. Jimi hendrix, holly herndon, GPT-3, timbre transfer and the promising failure aesthetics of musical AIs
  25. Comparison through conversation
  26. Deliberation by, with, and for University Students
  27. Die religiöse Konstante
  28. Analyzing pre- and in-service teachers’ feedback practice with microteaching videos