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Cascade Dehydrative Amination of Glycerol to Oxazoline

Abstract

Transformation of biomass into valuable nitrogen containing compounds is highly desired, yet less explored. Here, we report a simple and efficient method for the direct conversion of bioglycerol to oxazoline involving glycerol dehydration to acetol followed by its amination using an aqueous solution of ammonia. For two step strategy a non-noble metal, Cu-Zr catalyst developed giving glycerol conversion of 78% to acetol followed by amination separately with 95% selectivity to oxazoline. Moreover, we have demonstrated a single pot oxazoline synthesis using Ru/C as most stable catalyst to achieve 95% selectivity to oxazoline without any leaching. XPS studies revealed the co-existence of multivalence Ru species in different percentages depending on the nature and structure of the support. These multivalence species (RuO2 and RuO3) have synergistic effect for activation of carbonyl group whereas Ru0 is an active site for ammonia dissociation. NH3-TPD and Py-IR results also suggest that presence of relatively moderate acid sites and higher Brønsted/Lewis acid ratio in the catalyst promote selective production of oxazoline. The reaction pathway involves first, the glycerol dehydration to acetol. In the subsequent step, NH3 was dissociatively adsorbed on the catalyst surface and the imine thus formed condensed with a second molecule of acetol to obtain oxazoline. The studied catalyst could be recycled successfully without any significant loss of catalytic activity.

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Publication details

The article was received on 25 Jan 2018, accepted on 29 Apr 2018 and first published on 30 Apr 2018


Article type: Paper
DOI: 10.1039/C8CY00185E
Citation: Catal. Sci. Technol., 2018, Accepted Manuscript
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    Cascade Dehydrative Amination of Glycerol to Oxazoline

    R. Pandya, R. B. Mane and C. V. Rode, Catal. Sci. Technol., 2018, Accepted Manuscript , DOI: 10.1039/C8CY00185E

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