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Process intensification of continuous-flow imine hydrogenation in catalyst-coated tube reactors
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Expósito, Antonio José, Bai, Yang, Tchabanenko, Kirill, Rebrov, Evgeny V. and Cherkasov, Nikolay (2019) Process intensification of continuous-flow imine hydrogenation in catalyst-coated tube reactors. Industrial & Engineering Chemistry Research, 58 (11). pp. 4433-4442. doi:10.1021/acs.iecr.8b06058
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WRAP-process-intensification-continuous-flow-imine-tube-reactors-2019.pdf - Accepted Version - Requires a PDF viewer. Download (824Kb) | Preview |
Official URL: https://doi.org/10.1021/acs.iecr.8b06058
Abstract
Hydrogenation of an imine (N-Cyclohexyl(benzylidene)imine) into a secondary amine (N-Benzylcyclohexylamine) was studied in catalyst-coated tube reactors to utilize the advantages of continuous-flow processes. Tetrahydrofuran (THF) was found to be an optimal solvent providing high reaction and low catalyst deactivation rates compared to toluene and isopropanol. Even in THF, however, the deactivation was noticeable, with a decrease in the imine hydrogenation rate of 80 and 47% during 20 h on stream over the Pd/C and Pd/SiO2 catalyst-coated tubes, respectively. After comparing various regeneration methods, we found that washing with isopropanol recovered the catalyst activity. The catalyst support affected regeneration: the Pd/SiO2 catalyst suffered from a permanent degradation, whereas the Pd/C was stable over multiple reaction-regeneration cycles. Process intensification study at a range of reaction temperatures allowed to establish the optimal secondary amine production temperature of 110 °C. The long-term stability test under the optimized conditions allowed reaching a turnover number (TON) of 150 000, an unprecedented value in heterogeneous imine hydrogenation. A reductive amination cascade reaction (aldehyde and amine condensation simultaneously with imine hydrogenation) showed the byproduct yield below 3%. The cascade reaction, however, decreased the reaction throughput by 45% compared to the direct imine hydrogenation still allowing for a throughput of 0.75 kg of product per day in a single 5 m catalyst-coated reactor opening a way for a multikilogram synthesis.
| Item Type: | Journal Article | ||||||||
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| Subjects: | T Technology > TP Chemical technology | ||||||||
| Divisions: | Faculty of Science > Engineering | ||||||||
| SWORD Depositor: | Library Publications Router | ||||||||
| Library of Congress Subject Headings (LCSH): | Flow chemistry, Imines, Amines, Hydrogenation | ||||||||
| Journal or Publication Title: | Industrial & Engineering Chemistry Research | ||||||||
| Publisher: | American Chemical Society (ACS) | ||||||||
| ISSN: | 1520-5045 | ||||||||
| Official Date: | 20 March 2019 | ||||||||
| Dates: |
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| Volume: | 58 | ||||||||
| Number: | 11 | ||||||||
| Page Range: | pp. 4433-4442 | ||||||||
| DOI: | 10.1021/acs.iecr.8b06058 | ||||||||
| Status: | Peer Reviewed | ||||||||
| Publication Status: | Published | ||||||||
| Publisher Statement: | “This document is the Accepted Manuscript version of a Published Work that appeared in final form in Industrial & Engineering Chemistry Research, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [insert ACS Articles on Request author-directed link to Published Work, see http://pubs.acs.org/page/policy/articlesonrequest/index.html].” | ||||||||
| Access rights to Published version: | Restricted or Subscription Access | ||||||||
| RIOXX Funder/Project Grant: |
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