One Pot Synthesis of N-acetyl-p-aminophenol via Hydrogenation of Nitrobenzene
1. Coal Chemical R&D Center of Kailuan Group, Tangshan 063611, China;
2. Key Lab of Green Chemical Technology & High Efficient Energy Saving of Hebei Province, Hebei University of Technology, Tianjin 300130, China;
3. Hebei Provincial Engineering Technology Research Center of Coal-based Chemicals and Materials, Tangshan 063018, China
Abstract：Aiming at the problems in the existing industrial production of acetaminophenol (APAP) synthesis process, the new technology of one pot direct synthesis of APAP with nitrobenzene as raw material in acetic acid and zinc salts mixed solution was investigated. The acylation of p-aminophenol (PAP) and the coupling process of acylation and hydrogenation were studied and analyzed. The results showed that acetic acid and zinc salt had a synergistic effect on the promotion of PAP formation from phenylhydroxylamine rearrangement, which could significantly improve the selectivity of PAP in the hydrogenation reaction, and the selectivity was 76.8%. During the hydrogenation reaction, zinc sulfate had a significant inhibitory effect on the acylation of PAP with acetic acid, while the effect of zinc acetate was obviously smaller. When the concentration of zinc acetate was 170 mmol/L, the conversion of acetic acid to PAP acylation can reach more than 50%. After the completion of the hydrogenation reaction followed by cooling, the formed PAP was completely converted to APAP by the method of acylation with acetic anhydride, and the highest yield of APAP was over 70%.
Li Hongjuan 1,3,Guan Congcong 2 et al. One Pot Synthesis of N-acetyl-p-aminophenol via Hydrogenation of Nitrobenzene[J]. 化学反应工程与工艺, 2017, 33(3): 249-254.
