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Towards sustainable manufacture of epichlorohydrin from glycerol using hydrotalcite-derived basic oxides

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Abstract

Commercial two-step processes to convert glycerol into epichlorohydrin are more benign compared to the predominant industrial route starting from propene in terms of materials requirements and CO2 emissions. Still, the use of alkali hydroxides in stoichiometric amounts in the second reaction, i.e., the dehydrochlorination of the dichloropropanol intermediate, leads to the formation of large amounts of salt wastes, thus limiting the greenness of the technology. Here, we show for the first time that the latter transformation can be selectively conducted in the gas phase in the presence of a heterogeneous hydrotalcite-derived mixed oxide of Al and Mg. Upon reaction, the lamellar solid is rehydrated to a hydrotalcite-like compound, which can effectively activate the alcoholic group of dichloropropanol owing to its strong Brønsted basic character and moderately high surface area. In-depth characterisation of the porous, compositional, structural and acid/base properties demonstrates that the HCl formed during the reaction causes the progressive exchange of interlayer OH groups by Cl atoms, thus gradually diminishing the reactivity of the material. Facile calcination restores the original mixed oxide structure and is shown to enable three equivalent consecutive reaction runs. Since the HCl evolved along with water upon regeneration can be recycled in the first step of the process, i.e., glycerol hydrochlorination, our approach paves the way for a waste-free and more atom efficient biobased epichlorohydrin production process.

Graphical abstract: Towards sustainable manufacture of epichlorohydrin from glycerol using hydrotalcite-derived basic oxides

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Publication details

The article was received on 25 Aug 2017, accepted on 16 Oct 2017 and first published on 16 Oct 2017


Article type: Paper
DOI: 10.1039/C7GC02610B
Citation: Green Chem., 2017, Advance Article
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    Towards sustainable manufacture of epichlorohydrin from glycerol using hydrotalcite-derived basic oxides

    G. M. Lari, G. Pastore, C. Mondelli and J. Pérez-Ramírez, Green Chem., 2017, Advance Article , DOI: 10.1039/C7GC02610B

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