Issue 23, 2021

Plastic waste to drug intermediate: targeted cleavage of C–O bonds in polyphenylene oxide to 3,5-dimethyl phenol

Abstract

While making fuels and chemicals via plastic upcycling has become an important research topic recently, integrating waste plastic into the drug supply chain is exceedingly rare. Here, starting from polyphenylene oxide plastic, the selective production of 3,5-dimethyl phenol as an important pharmaceutical intermediate was achieved over Ru/Nb2O5, which is the first example of integrating waste plastic into the drug supply chain. It is found that the small-sized Ru particles and the Brønsted acid sites play key roles in the selective production of 3,5-dimethyl phenol. One the one hand, the small-sized Ru particles on 0.05% Ru/Nb2O5 inhibit the saturation of the aromatic ring (no ring saturation products were detected) and the removal of the phenolic hydroxyl group, resulting in a high selectivity to phenolic products. On the other hand, the Brønsted acid sites in Ru/Nb2O5 can stabilize the carbocation intermediates in the C(o)–O cleavage process, affording a distinct selectivity to 3,5-dimethyl phenol. This catalyst was also capable of handling common polyphenylene oxide plastics to selectively prepare 3,5-dimethyl phenol, adding new options for the synthesis of 3,5-dimethyl phenol.

Graphical abstract: Plastic waste to drug intermediate: targeted cleavage of C–O bonds in polyphenylene oxide to 3,5-dimethyl phenol

Supplementary files

Article information

Article type
Paper
Submitted
03 Aga 2021
Accepted
26 Okt 2021
First published
26 Okt 2021

Green Chem., 2021,23, 9640-9645

Plastic waste to drug intermediate: targeted cleavage of C–O bonds in polyphenylene oxide to 3,5-dimethyl phenol

B. Feng, Y. Jing, Y. Guo, X. Liu and Y. Wang, Green Chem., 2021, 23, 9640 DOI: 10.1039/D1GC02767K

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