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

Chenyue Zhang, Zhen Song, Can Jin, Job Nijhuis, Teng Zhou, Timothy Noël, Harald Gröger, Kai Sundmacher, Jan van Hest, Volker Hessel (Corresponding author)

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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.

Originele taal-2Engels
Artikelnummer123399
Aantal pagina's10
TijdschriftChemical Engineering Journal
Volume385
DOI's
StatusGepubliceerd - 1 apr 2020

Vingerafdruk

ketone
aldehyde
Ketones
Aldehydes
Screening
solubility
Solubility
Separators
Purification
purification
3-hydroxybutanal
screening
residence time
Physical properties
physical property
product
Recovery
simulation

Citeer dit

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title = "Screening of functional solvent system for automatic aldehyde and ketone separation in aldol reaction: a combined COSMO-RS and experimental approach",
abstract = "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.",
keywords = "Automatic separation, Biphasic and triphasic system, Computer-aided solvent selection, Integrated reactor-separator, Microflow, Process intensification",
author = "Chenyue Zhang and Zhen Song and Can Jin and Job Nijhuis and Teng Zhou and Timothy No{\"e}l and Harald Gr{\"o}ger and Kai Sundmacher and {van Hest}, Jan and Volker Hessel",
year = "2020",
month = "4",
day = "1",
doi = "10.1016/j.cej.2019.123399",
language = "English",
volume = "385",
journal = "Chemical Engineering Journal",
issn = "1385-8947",
publisher = "Elsevier",

}

Screening of functional solvent system for automatic aldehyde and ketone separation in aldol reaction : a combined COSMO-RS and experimental approach. / Zhang, Chenyue; Song, Zhen; Jin, Can; Nijhuis, Job; Zhou, Teng; Noël, Timothy; Gröger, Harald; Sundmacher, Kai; van Hest, Jan; Hessel, Volker (Corresponding author).

In: Chemical Engineering Journal, Vol. 385, 123399, 01.04.2020.

Onderzoeksoutput: Bijdrage aan tijdschriftTijdschriftartikelAcademicpeer review

TY - JOUR

T1 - Screening of functional solvent system for automatic aldehyde and ketone separation in aldol reaction

T2 - a combined COSMO-RS and experimental approach

AU - Zhang, Chenyue

AU - Song, Zhen

AU - Jin, Can

AU - Nijhuis, Job

AU - Zhou, Teng

AU - Noël, Timothy

AU - Gröger, Harald

AU - Sundmacher, Kai

AU - van Hest, Jan

AU - Hessel, Volker

PY - 2020/4/1

Y1 - 2020/4/1

N2 - 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.

AB - 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.

KW - Automatic separation

KW - Biphasic and triphasic system

KW - Computer-aided solvent selection

KW - Integrated reactor-separator

KW - Microflow

KW - Process intensification

UR - http://www.scopus.com/inward/record.url?scp=85075344557&partnerID=8YFLogxK

U2 - 10.1016/j.cej.2019.123399

DO - 10.1016/j.cej.2019.123399

M3 - Article

AN - SCOPUS:85075344557

VL - 385

JO - Chemical Engineering Journal

JF - Chemical Engineering Journal

SN - 1385-8947

M1 - 123399

ER -