Issue 7, 2024

One-pot mechanochemical hydrogenation and acetylation of 4-nitrophenol to 4-aminophenol and paracetamol

Abstract

The mechanochemical hydrogenation of 4-nitrophenol was examined in a ball mill reactor. Hydrogen gas flows through the reactor at ambient temperature and pressure in the presence of Pd/C catalyst and acetic anhydride. Under optimized conditions, simultaneous hydrogenation and acetylation in one pot increased paracetamol selectivity by avoiding undesirable side reactions of 4-aminophenol. Side product formation was further reduced through a novel bubbler configuration allowing for the delivery of acetic anhydride vapor to the reaction vessel. Ball mill results were compared to traditional stirred tank hydrogenations in a Parr reactor and shown to have superior yield and process mass intensity.

Graphical abstract: One-pot mechanochemical hydrogenation and acetylation of 4-nitrophenol to 4-aminophenol and paracetamol

Supplementary files

Article information

Article type
Paper
Submitted
05 Nov 2023
Accepted
23 Feb 2024
First published
29 Feb 2024
This article is Open Access
Creative Commons BY-NC license

Green Chem., 2024,26, 4079-4091

One-pot mechanochemical hydrogenation and acetylation of 4-nitrophenol to 4-aminophenol and paracetamol

J. Park, J. S. Maier, C. Evans, M. Hatzell, S. France, C. Sievers and A. S. Bommarius, Green Chem., 2024, 26, 4079 DOI: 10.1039/D3GC04281B

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