The fate of fluoroarenes in the environment has become an increasing concern due to the higher use of fluoroarenes in pharmaceuticals and industrial processes. One way to help alleviate this environmental concern is to explore ways in which fluoroarenes are degraded to benign compounds. Fluorinated aromatic compounds are hydrodefluorinated using a heterogeneous 5 wt % rhodium on alumina catalyst under mild conditions (1 atm. H2, 25°C). The catalytic hydrodehalogenation mechanism and substrate scope were explored by looking at a variety of substituted fluoroarenes. The effects of electron-withdrawing and electron-donating substituents as well as the position of the substituents to the fluorine atom (ortho, meta, para) were examined. The substrate degradation rates were monitored using GC/MS. When possible the intermediate(s), and product formation was examined as well. The fluorophenols are the quickest to undergo degradation with an average rate of 5 +/- 2 x10-3 min-1mg-1 Rh/Al2O3 and the fluoronitrobenzenes, with an average rate of 0.9 + 0.8 x10-3 min-1mg-1 Rh/Al2O3, are the slowest.

Rhodium catalyzed hydrogenation of fluoroarenes in mild condition

251st National Meeting (2016)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.