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Improving the efficiency of the Diels-Alder process by using flow chemistry and zeolite catalysis

(2017) GREEN CHEMISTRY . 19(1). p.237-248
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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.
Keywords
LEWIS-ACID CATALYSTS, ANOMALOUS ENDO/EXO SELECTIVITIES, CHIRAL SUPRAMOLECULAR CATALYSTS, LARGE-PORE ZEOLITES, IONIC LIQUIDS, P-BENZOQUINONE, ALPHA, BETA-UNSATURATED ALDEHYDES, MICROENGINEERED REACTORS, ORGANIC TRANSFORMATIONS, METHYL-METHACRYLATE

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Chicago
Seghers, Sofie, L Protasova, S Mullens, Joris Thybaut, and Chris Stevens. 2017. “Improving the Efficiency of the Diels-Alder Process by Using Flow Chemistry and Zeolite Catalysis.” Green Chemistry 19 (1): 237–248.
APA
Seghers, Sofie, Protasova, L., Mullens, S., Thybaut, J., & Stevens, C. (2017). Improving the efficiency of the Diels-Alder process by using flow chemistry and zeolite catalysis. GREEN CHEMISTRY , 19(1), 237–248.
Vancouver
1.
Seghers S, Protasova L, Mullens S, Thybaut J, Stevens C. Improving the efficiency of the Diels-Alder process by using flow chemistry and zeolite catalysis. GREEN CHEMISTRY . 2017;19(1):237–48.
MLA
Seghers, Sofie, L Protasova, S Mullens, et al. “Improving the Efficiency of the Diels-Alder Process by Using Flow Chemistry and Zeolite Catalysis.” GREEN CHEMISTRY 19.1 (2017): 237–248. Print.
@article{8509814,
  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.},
  author       = {Seghers, Sofie and Protasova, L and Mullens, S and Thybaut, Joris and Stevens, Chris},
  issn         = {1463-9262},
  journal      = {GREEN CHEMISTRY },
  keywords     = {LEWIS-ACID CATALYSTS,ANOMALOUS ENDO/EXO SELECTIVITIES,CHIRAL SUPRAMOLECULAR CATALYSTS,LARGE-PORE ZEOLITES,IONIC LIQUIDS,P-BENZOQUINONE,ALPHA,BETA-UNSATURATED ALDEHYDES,MICROENGINEERED REACTORS,ORGANIC TRANSFORMATIONS,METHYL-METHACRYLATE},
  language     = {eng},
  number       = {1},
  pages        = {237--248},
  title        = {Improving the efficiency of the Diels-Alder process by using flow chemistry and zeolite catalysis},
  url          = {http://dx.doi.org/10.1039/c6gc02334g},
  volume       = {19},
  year         = {2017},
}

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