Thermal degradation of polybrominated diphenyl ethers over as-prepared Fe3O4 micro/nano-material and hypothesized mechanism

Environ Sci Pollut Res Int. 2016 Jan;23(2):1540-51. doi: 10.1007/s11356-015-5400-z. Epub 2015 Sep 16.

Abstract

The thermal degradation of decabromodiphenyl ether (BDE-209) featuring fully substituted bromines was investigated over an as-prepared Fe3O4 micro/nano-material at 300 °C. Degradation followed pseudo-first-order kinetics with kobs = 0.15 min(-1) higher than that for decachlorobiphenyl (CB-209). Twenty-six newly produced polybrominated diphenyl ether (PBDE) congeners were identified using the available PBDE standards, while four PBDE congener products were predicted using third-order polynomial regression equation. Analysis of the products indicated that BDE-209 underwent stepwise hydrodebromination over as-prepared Fe3O4. Similar to the case for CB-209, two initial hydrodebromination steps are favored at the BDE-209 meta-positions, giving the major products BDE-207 and BDE-197. However, the variance about the preferred products began to emerge from the start of heptabromodiphenyl ethers (hepta-BDEs). The majorly produced hepta-BDE isomer with BDE-183 is unbrominated at one ortho-position. However, this is different from the reported degradation of CB-209, which always produced the products chlorinated at all four ortho-positions until the ortho-position had to be removed for the formation of trichlorobiphenyls and dichlorobiphenyl still majorly chlorinated at three or two ortho-positions. The early BDE-209 hydrodebromination steps appear to be strongly influenced by steric effects, whereas subsequent hydrodebromination steps, as more bromine atoms are removed, will be gradually governed more by thermodynamics.

Keywords: Degradation pathway; Fe3O4 micro/nano-material; Hydrodebromination products; Polybrominated diphenyl ether; Steric effect; Thermodynamics.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bromine / chemistry
  • Halogenated Diphenyl Ethers / chemistry*
  • Nanostructures*
  • Polybrominated Biphenyls / chemistry*

Substances

  • Halogenated Diphenyl Ethers
  • Polybrominated Biphenyls
  • 2,2',3,3',4,4',6,6'-octabromodiphenyl ether
  • 2,2',3,4,4',5',6-heptabromodiphenyl ether
  • 2,2',3,3',4,4',5,6,6'-nonabromodiphenyl ether
  • decabromobiphenyl ether
  • Bromine