A comparison of the catalytic hydrogenation of 2-amylanthraquinone and 2-ethylanthraquinone over a Pd/Al ₂O₃ catalyst

Abstract

The hydrogenation of 2-ethylanthraquinone (eAQ), 2-tert-amylanthraquinone (taAQ) and their mixtures with molar ratios of 1:1 and 1:2 to the corresponding hydroquinones (eAQH₂ and taAQH₂) were studied over a Pd/Al₂O₃ catalyst in a semi-batch slurry reactor at 60 °C and at 0.3 MPa. Compared to eAQ, TaAQ exhibited a significantly slower hydrogenation rate (about half) but had a higher maximum yield of H₂O₂ and a smaller amount of degradation products. This can be ascribed to the longer and branched side chain in taAQ, which limits its accessibility to the Pd surface and its diffusion through the pores of the catalyst. Density functional theory calculations showed that it is more difficult for taAQ to adsorb onto a Pd (111) surface than for eAQ. The hydrogenation of the eAQ/taAQ mixtures had the slowest rates, lowest H₂O₂yields and the highest amounts of degradation products.

Graphical abstract

Keywords

hydrogenation / hydrogen peroxide / anthraquinone / Pd catalyst / AO process

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Acknowledgements

This work is supported by financial support from the National Natural Science Foundation of China (Grant No. 21676184).

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