Screening of functional solvent system for automatic aldehyde and ketone separation in aldol reaction: A combined COSMO-RS and experimental approach

Zhang C, Song Z, Jin C, Nijhuis J, Zhou T, Noel T, Gröger H, Sundmacher K, van Hest J, Hessel V (2020)
CHEMICAL ENGINEERING JOURNAL 385: 123399.

Zeitschriftenaufsatz | E-Veröff. vor dem Druck | Englisch
 
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Autor*in
Zhang, Chenyue; Song, Zhen; Jin, Can; Nijhuis, Job; Zhou, Teng; Noel, Timothy; Gröger, HaraldUniBi; Sundmacher, Kai; van Hest, Jan; Hessel, Volker
Abstract / Bemerkung
An integrated reaction-separation process based on only solvents is presented, and thus without the need for related technical equipment (reactor-separator). Both product purification and reactant recovery are achieved automatically for an asymmetric aldol reaction employing a biphasic solvent system as compartmentalizing soft matter. Firstly, COSMO-RS based simulation is introduced as a theoretical guidance in the solvent selection for the reactant 3-chlorobenzaldehyde and non-solvent selection for the R-aldol product, (R) 4 (3 chlorophenyl)-4-hydroxybutan-2-one. This encompasses solubility as core critical parameter, as well as chemo-physical properties and environmental profiling. Such criteria-cascaded screening could effectively reduce a 7665 solvents-database into 1 candidate solvent, which is dodecane, before experimental process assessment. Secondly, this screening's top candidate was validated as the best reaction solvent by first a solubility test and then by a batch reaction, in which a conversion of 69% was achieved. As desired, the mono-phase reaction yielded spontaneously the product layer and the separate dodecane phase as the second layer, which indeed allowed facile separation of the product from the residual reactant. In a third step, a segmented flow process was developed giving a highest product yield of 63% and a total conversion 92% respectively after a 2 h residence time.
Stichworte
Process intensification; Microflow; Computer-aided solvent selection; Automatic separation; Biphasic and triphasic system; Integrated; reactor-separator
Erscheinungsjahr
2020
Zeitschriftentitel
CHEMICAL ENGINEERING JOURNAL
Band
385
Art.-Nr.
123399
ISSN
1385-8947
eISSN
1873-3212
Page URI
https://pub.uni-bielefeld.de/record/2940695

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Zhang C, Song Z, Jin C, et al. Screening of functional solvent system for automatic aldehyde and ketone separation in aldol reaction: A combined COSMO-RS and experimental approach. CHEMICAL ENGINEERING JOURNAL. 2020;385: 123399.
Zhang, C., Song, Z., Jin, C., Nijhuis, J., Zhou, T., Noel, T., Gröger, H., et al. (2020). Screening of functional solvent system for automatic aldehyde and ketone separation in aldol reaction: A combined COSMO-RS and experimental approach. CHEMICAL ENGINEERING JOURNAL, 385, 123399. doi:10.1016/j.cej.2019.123399
Zhang, C., Song, Z., Jin, C., Nijhuis, J., Zhou, T., Noel, T., Gröger, H., Sundmacher, K., van Hest, J., and Hessel, V. (2020). Screening of functional solvent system for automatic aldehyde and ketone separation in aldol reaction: A combined COSMO-RS and experimental approach. CHEMICAL ENGINEERING JOURNAL 385:123399.
Zhang, C., et al., 2020. Screening of functional solvent system for automatic aldehyde and ketone separation in aldol reaction: A combined COSMO-RS and experimental approach. CHEMICAL ENGINEERING JOURNAL, 385: 123399.
C. Zhang, et al., “Screening of functional solvent system for automatic aldehyde and ketone separation in aldol reaction: A combined COSMO-RS and experimental approach”, CHEMICAL ENGINEERING JOURNAL, vol. 385, 2020, : 123399.
Zhang, C., Song, Z., Jin, C., Nijhuis, J., Zhou, T., Noel, T., Gröger, H., Sundmacher, K., van Hest, J., Hessel, V.: Screening of functional solvent system for automatic aldehyde and ketone separation in aldol reaction: A combined COSMO-RS and experimental approach. CHEMICAL ENGINEERING JOURNAL. 385, : 123399 (2020).
Zhang, Chenyue, Song, Zhen, Jin, Can, Nijhuis, Job, Zhou, Teng, Noel, Timothy, Gröger, Harald, Sundmacher, Kai, van Hest, Jan, and Hessel, Volker. “Screening of functional solvent system for automatic aldehyde and ketone separation in aldol reaction: A combined COSMO-RS and experimental approach”. CHEMICAL ENGINEERING JOURNAL 385 (2020): 123399.