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Dehydrogenative Coupling of Toluene Promoted by Multi-Walled Carbon Nanotubes

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Abstract

We report here the formation of carbon–carbon bonds via carbon-hydrogen bond activation catalysed by multi-walled carbon nanotubes (mwcnts), the catalytic activity of which is influenced by nanocarbon morphology and structure. Control of nanocarbon defects and edges allows the realisation of a high-performance carbon-based catalyst that can replace its metal-based counterparts.

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Notes

  1. The reaction produces isomeric o-, m-, and p-substituted products in a 4:1:5 ratio regardless of the conditions.

  2. MWCNTs (1 g) were placed in a ceramic container and heated in an electric furnace at 850 °C for 4 h in air. The residue (~ 1 mg) was analyzed by EDX, leading to the detection of Fe and other metals (Fig. S1).

  3. Although XPS did not show the difference before and after mCPBA treatment, thermo-gravimetric analysis (TGA) showed increased weight loss for ox-MWCNTs at 200 °C and 530 °C. Such an increased weight loss would suggest the formation of oxygenated functional groups and defects on MWCNTs. Results of TGA and zeta potential analysis of the recovered MWCNT are also shown in Fig S2 and Table S1.

  4. Products of homolytic C–C, C–O, and O–O bond cleavage of mCPBA (m-chlorobenzoic acid, benzyl m-chlorobenzoate, 3,3'-dichloro-1,1'-biphenyl) were observed in the reaction mixture. Therefore, the type of radical mainly contributing to the reaction is unclear.

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Acknowledgements

The authors gratefully acknowledge W. Chen for his contribution to XPS measurements, T. Yamazaki for his contribution to ESR measurements and H. Suzuki for his contribution to NMR. This work was financially supported by JST SICORP, ANR (ANR-15-JTIC-0002-01), and the Egyptian government.

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Authors and Affiliations

  1. Research Core for Interdisciplinary Sciences, Okayama University, Tsushimanaka, Kita-ku, Okayama, 700-8530, Japan

    Soliman I. El-Hout & Yuta Nishina

  2. Nanomaterials and Nanotechnology Department, Central Metallurgical Research and Development Institute (CMRDI), P.O. 87, Helwan, 11421, Egypt

    Soliman I. El-Hout

  3. Graduate School of Natural Science and Technology, Okayama University, Tsushimanaka, Kita-ku, Okayama, 700-8530, Japan

    Yang Zhou, Jun Kano & Yuta Nishina

  4. Graduate School of Engineering Science, Osaka University, 1-3 Machikaneyama-cho, Toyonaka, Japan

    Yoshiaki Uchida

  5. Precursory Research for Embryonic Science and Technology, Japan Science and Technology Agency, 4-1-8 Honcho, Kawaguchi, Saitama, 332-0012, Japan

    Yoshiaki Uchida & Yuta Nishina

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  1. Soliman I. El-Hout
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  2. Yang Zhou
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  3. Jun Kano
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  4. Yoshiaki Uchida
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Correspondence to Soliman I. El-Hout or Yuta Nishina.

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El-Hout, S.I., Zhou, Y., Kano, J. et al. Dehydrogenative Coupling of Toluene Promoted by Multi-Walled Carbon Nanotubes. Catal Lett 150, 256–262 (2020). https://doi.org/10.1007/s10562-019-02951-z

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  • DOI: https://doi.org/10.1007/s10562-019-02951-z

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