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Issue 22, 2016
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Direct C–C coupling of bio-ethanol into 2,3-butanediol by photochemical and photocatalytic oxidation with hydrogen peroxide

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Abstract

Theoretically, selective C–H manipulation in ethanol can result in a direct C–C coupling synthesis of 2,3-butanediol (2,3-BDO). However, this process is typically extremely difficult to achieve because of the high complexity of the involved chemical bonds. In this work, we determine that hydroxide radicals generated from the photolysis of H2O2 can selectively attack the α-hydrogen atom in ethanol aqueous solutions and crack the C–H bond to produce hydroxyethyl radicals, which subsequently undergo C–C coupling to form 2,3-BDO. This selective C–H breakage is determined by the reaction rate, which is primarily controlled by the local H2O2 concentration at a given irradiation intensity. At a moderate reaction rate of ethanol (37 mmol h−1), the 2,3-BDO selectivity reaching as high as 91% can be obtained. The introduction of a catalyst can further increase ethanol conversion and enhance the 2,3-BDO formation rate by controlling the reaction rate. This result provides an environment-friendly approach to convert bio-ethanol directly to 2,3-BDO and to manipulate a single bond selectively in complex bonding situations.

Graphical abstract: Direct C–C coupling of bio-ethanol into 2,3-butanediol by photochemical and photocatalytic oxidation with hydrogen peroxide

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Publication details

The article was received on 29 Mar 2016, accepted on 14 Jun 2016 and first published on 31 Aug 2016


Article type: Paper
DOI: 10.1039/C6GC00883F
Citation: Green Chem., 2016,18, 6029-6034
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    Direct C–C coupling of bio-ethanol into 2,3-butanediol by photochemical and photocatalytic oxidation with hydrogen peroxide

    N. Li, W. Yan, P. Yang, H. Zhang, Z. Wang, J. Zheng, S. Jia and Z. Zhu, Green Chem., 2016, 18, 6029
    DOI: 10.1039/C6GC00883F

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