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

Park, Jimin; Maier, Jacob S.; Evans, Caria; Hatzell, Marta; France, Stefan; Sievers, Carsten; Bommarius, Andreas S.

doi:10.1039/d3gc04281b

Green Chem.

2024

DOI: 10.1039/d3gc04281b

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

Jimin Park,

Jacob S. Maier,

Caria Evans

et al.

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...

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Cited by 3 publications

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Renewables-Based Routes to Paracetamol: A Green Chemistry Analysis

Park,

Evans,

Maier

et al. 2024

ACS Sustainable Chem. Eng.

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Three potential routes for paracetamol synthesis from renewable phenol feedstock were examined and compared to each other and existing industrial routes with respect to Green Chemistry metrics and industrial viability. The routes tested were the acetamidation of hydroquinone, the imination and reduction of benzoquinone, and the hydrogenation of 4-nitrophenol. The hydroquinone and benzoquinone routes suffered from poor conversion and selectivity. The 4-nitrophenol route achieved good conversion, yield, and Green Chemistry metrics and is the most industrially viable of the three routes. When compared to existing routes, the 4-nitrophenol route is comparable or superior in terms of reactor metrics, Green Chemistry considerations, and raw material costs.

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Renewables-Based Routes to Paracetamol: A Green Chemistry Analysis

Park,

Evans,

Maier

et al. 2024

ACS Sustainable Chem. Eng.

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Comparison of traditional and mechanochemical production processes for nine active pharmaceutical ingredients (APIs)

Leitão

2024

RSC Sustain.

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Sequential Copper-Catalyzed Amidation and Hydroxylation for Acetaminophen Synthesis

Yoo,

Kim,

Seo

2024

Synlett

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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...

Cited by 3 publications

References 43 publications

Renewables-Based Routes to Paracetamol: A Green Chemistry Analysis

Renewables-Based Routes to Paracetamol: A Green Chemistry Analysis

Comparison of traditional and mechanochemical production processes for nine active pharmaceutical ingredients (APIs)

Sequential Copper-Catalyzed Amidation and Hydroxylation for Acetaminophen Synthesis

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