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Issue 1, 2017
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Improving the efficiency of the Diels–Alder process by using flow chemistry and zeolite catalysis

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Abstract

The industrial application of the Diels–Alder reaction for the atom-efficient synthesis of (hetero)cyclic compounds constitutes an important challenge. Safety and purity concerns, related to the instability of the polymerization prone diene and/or dienophile, limit the scalability of the production capacity of Diels–Alder products in a batch mode. To tackle these problems, the use of a high-pressure continuous microreactor process was considered. In order to increase the yields and the selectivity towards the endo-isomer, commercially available zeolites were used as a heterogeneous catalyst in a microscale packed bed reactor. As a result, a high conversion (≥95%) and endo-selectivity (89 : 11) were reached for the reaction of cyclopentadiene and methyl acrylate, using a 1 : 1 stoichiometry. A throughput of 0.87 g h−1 during at least 7 h was reached, corresponding to a 3.5 times higher catalytic productivity and a 14 times higher production of Diels–Alder adducts in comparison to the heterogeneous lab-scale batch process. Catalyst deactivation was hardly observed within this time frame. Moreover, complete regeneration of the zeolite was demonstrated using a straightforward calcination procedure.

Graphical abstract: Improving the efficiency of the Diels–Alder process by using flow chemistry and zeolite catalysis

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Publication details

The article was received on 21 Aug 2016, accepted on 24 Oct 2016 and first published on 25 Oct 2016


Article type: Paper
DOI: 10.1039/C6GC02334G
Citation: Green Chem., 2017,19, 237-248
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    Improving the efficiency of the Diels–Alder process by using flow chemistry and zeolite catalysis

    S. Seghers, L. Protasova, S. Mullens, J. W. Thybaut and C. V. Stevens, Green Chem., 2017, 19, 237
    DOI: 10.1039/C6GC02334G

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