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Reductive alkylation of p-nitroaniline with butanone over Cu–Cr–Ca/γ-Al2O3 to give N,N′-di-sec-butyl-p-phenylenediamine

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Abstract

Several Cu-based catalysts were prepared and investigated for reductive alkylation of p-nitroaniline with butanone. Performance of Cu–Cr–Ca/γ-Al2O3 was excellent. N,N’-di-sec-butyl-p-phenylenediamine was obtained in approximately 98.0 % yield under mild conditions. Results from XRD, XPS, and NH3-TPD characterization revealed that introduction of Cr remarkably improved the dispersion of Cu0 active sites whereas addition of Ca partly reduced the strong acid capacity of the catalyst. The reaction conditions, including reaction temperature and hydrogen pressure, were also optimized and the catalyst performed well for 100 h under the optimized conditions.

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Authors and Affiliations

  1. School of Chemical Engineering and Technology, Tianjin University, Tianjin, 300072, People’s Republic of China

    Liang Lu, Yifan Duan, Jun Tian, Ge Song & Yang Li

  2. School of Pharmaceutical Science and Technology, Tianjin University, Tianjin, 300072, People’s Republic of China

    Xiangjin Kong

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  1. Liang Lu
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  2. Xiangjin Kong
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  3. Yifan Duan
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  4. Jun Tian
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  5. Ge Song
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  6. Yang Li
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Correspondence to Yang Li.

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Lu, L., Kong, X., Duan, Y. et al. Reductive alkylation of p-nitroaniline with butanone over Cu–Cr–Ca/γ-Al2O3 to give N,N′-di-sec-butyl-p-phenylenediamine. Res Chem Intermed 41, 549–557 (2015). https://doi.org/10.1007/s11164-013-1209-x

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