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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.

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Authors and Affiliations

  1. Department of Biological System Sciences, Graduate School of Comprehensive Scientific Research, Prefectural University of Hiroshima, 562 Nanatsuka-Cho, Shobara City, Hiroshima, 727-0023, Japan

    Yumi Katayama

  2. Department of Environmental Sciences, Prefectural University of Hiroshima, 562 Nanatsuka-Cho, Shobara City, Hiroshima, 727-0023, Japan

    Mitsuru Aoyagi, Takuya Matsumoto, Hiroyuki Harada, Naoyoshi Egashira & Yoshiharu Mitoma

  3. Department of Organic Chemistry, Politehnica University of Bucharest, 060042, Bucharest, Romania

    Alina M. Simion & Cristian Simion

Authors
  1. Yumi Katayama
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  2. Mitsuru Aoyagi
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  3. Takuya Matsumoto
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  4. Hiroyuki Harada
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  5. Alina M. Simion
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  6. Naoyoshi Egashira
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  7. Yoshiharu Mitoma
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  8. Cristian Simion
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Corresponding authors

Correspondence to Yoshiharu Mitoma or Cristian Simion.

Additional information

Responsible editor: Santiago V. Luis

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.

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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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  • DOI: https://doi.org/10.1007/s11356-016-7785-8

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