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Issue 2, 2020
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Continuous flow synthesis of menthol via tandem cyclisation–hydrogenation of citronellal catalysed by scrap catalytic converters

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Abstract

A continuous flow synthesis of menthol starting from citronellal catalysed by scrap catalytic converters is reported. The reaction was conducted in a tandem system connecting in series two catalytic systems, with the first having Lewis acid properties (favouring the cyclisation of citronellal to isopulegols) and the second having hydrogenation catalytic activity (catalysing the hydrogenation of isopulegols to menthols). A Lewis acid catalyst was prepared by supporting iron oxide nanoparticles over a waste material, i.e. the ceramic core of scrap catalytic converters (SCATs) via a microwave assisted method. Most importantly, SCATs, containing a low residual noble metal content, could be directly employed in the second step as hydrogenation catalysts. The reaction was performed studying the influence on the yield and selectivity to (−)-menthol of various reaction parameters (T, p and flow rate). Under the best reaction conditions (at a flow rate of 0.1 mL min−1 and at 373 K and 413 K for cyclisation and hydrogenation steps respectively) a conversion of >99% of (+)-citronellal to (−)-menthol with 77% final yield was achieved.

Graphical abstract: Continuous flow synthesis of menthol via tandem cyclisation–hydrogenation of citronellal catalysed by scrap catalytic converters

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Article information


Submitted
19 Sep 2019
Accepted
20 Nov 2019
First published
25 Nov 2019

Green Chem., 2020,22, 379-387
Article type
Paper

Continuous flow synthesis of menthol via tandem cyclisation–hydrogenation of citronellal catalysed by scrap catalytic converters

A. Zuliani, C. M. Cova, R. Manno, V. Sebastian, A. A. Romero and R. Luque, Green Chem., 2020, 22, 379
DOI: 10.1039/C9GC03299A

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