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Synthesis 2022; 54(16): 3605-3612
DOI: 10.1055/a-1807-3188
DOI: 10.1055/a-1807-3188
paper
Flow Hydrogenation of 1,3,5-Trinitrobenzenes over Cu-Based Catalysts as an Efficient Approach for the Preparation of Phloroglucinol Derivatives
This work was supported by the Russian Science Foundation (grant no. 22-23-00127).
Abstract
An environmentally friendly and safe synthesis of phloroglucinol and its derivatives through the flow hydrogenation of 1,3,5-trinitrobenzenes on heterogeneous copper catalysts is reported. It was found that hydrogenation of 1,3,5-trinitrobenzene, 2,4,6-trinitrotoluene, 2,4,6-trinitroxylene, and 2,4,6-trinitromesitylene in methanol over Cu–Al mixed oxides derived from layered double hydroxides led to selective formation of the corresponding triaminobenzenes, which were isolated from the reaction mixture in the form of double salts with sulfuric acid and were stable in storage. Subsequent hydrolysis in aqueous solution gave the phloroglucinol derivatives in good yields (75–82%).
Key words
trinitrobenzenes - hydrogenation - flow reactor - heterogeneous catalysis - mixed oxides - layered double hydroxides - phloroglucinol derivativesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1807-3188.
- Supporting Information
Publication History
Received: 02 March 2022
Accepted after revision: 23 March 2022
Accepted Manuscript online:
23 March 2022
Article published online:
17 May 2022
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