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Hydrodehalogenation of hexachloro- and hexabromobenzene by metallic calcium in ethanol, in the presence of Rh/C catalyst

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Abstract

Both hexachlorobenzene and hexabromobenzene were successfully hydrodehalogenated to the monohalogenated derivative and ultimately to benzene (which was subsequently reduced to cyclohexane) using a mixture of metallic Ca, ethanol, and Rh/C, by simple stirring in diethyl ether, at room or mild temperature (60 °C). Various experiments were performed in order to assess the role of the solvent and Rh/C catalyst, as well as for elucidating the reaction pathway.

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Acknowledgment

The authors wish to express their thanks to Asuka Takagi and Hiromi Hasegawa from the Mitsubishi Chemical Engineering Corporation as technical experts for measurements by GC and GC-FID.

Author information

Correspondence to Yoshiharu Mitoma or Cristian Simion.

Additional information

Highlights

• Hydrodehalogenation occurs for both hexachloro- and hexabromobenzene, in mild conditions;

• Ultimate reaction product is cyclohexane and/or benzene;

• For the reaction to occur, both Ca and ethanol reagents, as well as Rh/C catalyst are necessary;

• No side-products (e.g., polyaromatic compounds) were recorded.

Responsible editor: Santiago V. Luis

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Katayama, Y., Aoyagi, M., Matsumoto, T. et al. Hydrodehalogenation of hexachloro- and hexabromobenzene by metallic calcium in ethanol, in the presence of Rh/C catalyst. Environ Sci Pollut Res 24, 591–597 (2017). https://doi.org/10.1007/s11356-016-7785-8

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Keywords

  • Hexachlorobenzene
  • Hexabromobenzene
  • Hydrodehalogenation
  • Metallic Ca
  • Ethanol
  • Rh/C