Issue 7, 2024

Direct amination of poly(p-phenylene oxide) to substituted anilines over bimetallic Pd–Ru catalysts

Abstract

Chemical upcycling of plastic waste offers a promising opportunity for synthesizing value-added products. Despite its potential, transforming poly(phenylene oxide) (PPO) into nitrogen-based chemicals remains underexplored. To that end, we report the direct conversion of PPO to dimethylanilines over bimetallic Pd–Ru/CNT in a mixture of octane and aqueous ammonia. In a one-pot manner, PPO is initially converted into substituted phenols, and then is aminated, yielding 30% dimethylanilines over Pd7Ru3/CNT under optimum conditions. The bimetallic catalyst outperforms its monometallic equivalents. Transmission electron microscopy (TEM), powder X-ray diffraction (XRD) and energy-dispersive X-ray spectroscopy (EDX) unveiled the features of well dispersed and small-sized metallic nanoparticles. Control experiments using deuterium indicated a high reliance of hydrogen and water for the amination step and the hydrogenolysis step, respectively. Furthermore, we demonstrated product isolation through a straightforward acid–base treatment and extraction. This work introduces a viable route for upcycling PPO into valuable nitrogen-containing compounds.

Graphical abstract: Direct amination of poly(p-phenylene oxide) to substituted anilines over bimetallic Pd–Ru catalysts

Supplementary files

Article information

Article type
Paper
Submitted
05 Okt 2023
Accepted
28 Jan 2024
First published
30 Jan 2024
This article is Open Access
Creative Commons BY-NC license

Green Chem., 2024,26, 3949-3957

Direct amination of poly(p-phenylene oxide) to substituted anilines over bimetallic Pd–Ru catalysts

P. T. T. Nguyen, G. Gözaydın, J. Ma, B. Yao, Q. He and N. Yan, Green Chem., 2024, 26, 3949 DOI: 10.1039/D3GC03757F

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