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Issue 25, 2019
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Aerobic oxidation of C4–C6 α,ω-diols to the diacids in base-free medium over zirconia-supported (bi)metallic catalysts

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Abstract

Oxidation of aliphatic α,ω-diols is a potentially interesting route to the production of valuable α,ω-diacids or ω-hydroxy acids for various polymer synthesis. 1,4-Butanediol (BDO), 1,5-pentanediol (PDO) and 1,6-hexanediol (HDO) are particularly attractive since they may be obtained from lignocellulosic biomass. The aqueous aerobic oxidation of these diols to the corresponding diacids was investigated in water over a set of Au, Pt, Au–Pt and Au–Pd catalysts supported on zirconia at 70 °C or 90 °C under 40 bar air. The nature of the metallic catalyst influenced the distribution of products as oxidation proceeded. The longer the carbon chain linking the terminal alcohol groups, the higher the yield of the diacid. The best yields of succinic acid, glutaric acid and adipic acid reached 83, 84 and 96% from BDO, PDO and HDO, respectively, over Au–Pt/ZrO2. There was some evidence of decarbonylation of the α,ω-hydroxyaldehyde at the early stage of the reaction. The presence of the hydroxyl substituent in 1,2,6-hexanetriol significantly slowed the oxidation rates compared with HDO. Besides, oxidation of PDO or HDO was highly selective to the ω-hydroxycarboxylate in moderate alkaline medium (NaOH/diol = 2) over Au/ZrO2 (90–93%).

Graphical abstract: Aerobic oxidation of C4–C6 α,ω-diols to the diacids in base-free medium over zirconia-supported (bi)metallic catalysts

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Publication details

The article was received on 02 Apr 2019, accepted on 18 May 2019 and first published on 20 May 2019


Article type: Paper
DOI: 10.1039/C9NJ01695C
New J. Chem., 2019,43, 9873-9885

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    Aerobic oxidation of C4–C6 α,ω-diols to the diacids in base-free medium over zirconia-supported (bi)metallic catalysts

    M. Mounguengui-Diallo, A. Sadier, D. Da Silva Perez, C. Nikitine, L. Puchot, Y. Habibi, C. Pinel, N. Perret and M. Besson, New J. Chem., 2019, 43, 9873
    DOI: 10.1039/C9NJ01695C

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