Conversion of platform chemical glycerol to cyclic acetals promoted by acidic ionic liquids

The condensation of glycerol, a platform chemical from renewable materials, with benzaldehyde to generate cyclic acetals was investigated using acidic ionic liquid as catalyst. Evidence was presented that the product mixture of 4-hydroxymethyl-2-phenyl-1,3-dioxolane and 5-hydroxyl-2-phenyl-1,3-dioxa...

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Veröffentlicht in:RSC advances 2014-01, Vol.4 (36), p.18917-18923
Hauptverfasser: Wang, Bo, Shen, Yue, Sun, Jiankui, Xu, Feng, Sun, Runcang
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Sprache:eng
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Zusammenfassung:The condensation of glycerol, a platform chemical from renewable materials, with benzaldehyde to generate cyclic acetals was investigated using acidic ionic liquid as catalyst. Evidence was presented that the product mixture of 4-hydroxymethyl-2-phenyl-1,3-dioxolane and 5-hydroxyl-2-phenyl-1,3-dioxane, with cisand transtwo stereo-isomers for each one identified by super(1)H NMR were obtained. Further modification of reaction conditions promoted by N-butyl-pyridinium bisulfate ([BPy]HSO sub(4)) led to the totally cyclic acetals with 99.8% yield at room temperature. A micro water-removal reactor constituted by ionic liquids was proposed, which favourably shifted the condensation equilibrium to the product side by transferring the produced water out of the organic phase in time, so that the water-carrying agent or reactive distillation was avoided. Moreover, the product separation made this methodology more accessible to sustainable green biomass chemistry.
ISSN:2046-2069
2046-2069
DOI:10.1039/c4ra01443j