4.7 Article

The effect of the hydroxyl group position on the electrochemical reactivity and product selectivity of butanediol electro-oxidation

Journal

DALTON TRANSACTIONS
Volume 51, Issue 38, Pages 14491-14497

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2dt02450k

Keywords

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Funding

  1. Singapore Ministry of Education Tier 2 Grants [MOE-T2EP10220-0001]
  2. Singapore National Research Foundation under its Campus for Research Excellence and Technological Enterprise (CREATE) programme [NRF-NRFF2017-04]
  3. Centre of Advanced Catalysis Science and Technology, Nanyang Technological University
  4. Agency for Science, Technology and Research (Central Research Fund Award)
  5. Singapore National Research Foundation under its NRF Fellowship [NRF-NRFF2017-04]

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This article presents a study on the effect of the hydroxyl group position on the electro-oxidation of butanediols. The results show that the reactivity of butanediols increases with the proximity of the hydroxyl groups, resulting in a lower anodic potential. The study also provides insights into reactant selection for the electrochemical synthesis of value-added chemicals.
This article presents a study on the effect of the hydroxyl group position on the electro-oxidation of butanediols, including 1,2-butanediol, 2,3-butanediol, 1,3-butanediol, and 1,4-butanediol. The effect of the hydroxyl group position in butanediols on their electro-oxidation reactivities is investigated by cyclic voltammetry, linear sweep voltammetry, chronopotentiometry and chronoamperometry in 1.0 M KOH. The results show that the closer the two hydroxyl groups are, the higher the reactivity, and the lower the anodic potential butanediol has. Moreover, the oxidation products from chronoamperometry are analyzed by means of HPLC and NMR. Some value-added products, such as 3-hydroxypropionic acid/3-hydroxypropionate, are produced. The DFT calculation indicates that the oxidation of vicinal diols responds to the conversion from a hydroxyl group to a carboxylate group, followed by C-C bond cleavage, where the carbon charge decreases. These results provide an insight into reactant selection for the electrochemical synthesis of value-added chemicals.

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