Inherent Ethyl Acetate Selectivity in a Trianglimine Molecular Solid

Donglin He; Chengxi Zhao; Linjiang Chen; Marc A. Little; Samantha Y. Chong; Rob Clowes; Katherine McKie; Mark G. Roper; Graeme M. Day; Ming Liu; Andrew I. Cooper

doi:10.1002/chem.202101510

Inherent Ethyl Acetate Selectivity in a Trianglimine Molecular Solid

Donglin He, Chengxi Zhao, Linjiang Chen, Marc A. Little, Samantha Y. Chong, Rob Clowes, Katherine McKie, Mark G. Roper, Graeme M. Day, Ming Liu, Andrew I. Cooper^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

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Abstract

Ethyl acetate is an important chemical raw material and solvent. It is also a key volatile organic compound in the brewing industry and a marker for lung cancer. Materials that are highly selective toward ethyl acetate are needed for its separation and detection. Here, we report a trianglimine macrocycle (TAMC) that selectively adsorbs ethyl acetate by forming a solvate. Crystal structure prediction showed this to be the lowest energy solvate structure available. This solvate leaves a metastable, “templated” cavity after solvent removal. Adsorption and breakthrough experiments confirmed that TAMC has adequate adsorption kinetics to separate ethyl acetate from azeotropic mixtures with ethanol, which is a challenging and energy-intensive industrial separation.

Original language	English
Pages (from-to)	10589-10594
Number of pages	6
Journal	Chemistry - A European Journal
Volume	27
Issue number	41
Early online date	27 May 2021
DOIs	https://doi.org/10.1002/chem.202101510
Publication status	Published - 21 Jul 2021

Keywords

crystal structure prediction
dynamic separation
macrocycles
molecular crystals
selective adsorption

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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This output contributes to the following UN Sustainable Development Goals (SDGs)

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title = "Inherent Ethyl Acetate Selectivity in a Trianglimine Molecular Solid",

abstract = "Ethyl acetate is an important chemical raw material and solvent. It is also a key volatile organic compound in the brewing industry and a marker for lung cancer. Materials that are highly selective toward ethyl acetate are needed for its separation and detection. Here, we report a trianglimine macrocycle (TAMC) that selectively adsorbs ethyl acetate by forming a solvate. Crystal structure prediction showed this to be the lowest energy solvate structure available. This solvate leaves a metastable, “templated” cavity after solvent removal. Adsorption and breakthrough experiments confirmed that TAMC has adequate adsorption kinetics to separate ethyl acetate from azeotropic mixtures with ethanol, which is a challenging and energy-intensive industrial separation.",

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note = "Funding Information: The authors acknowledge the Engineering and Physical Sciences Research Council (EPSRC) (EP/N004884/1) and the Leverhulme Trust via the Leverhulme Research Centre for Functional Materials Design for funding. D. He thanks the Oversea Study Program of Guangzhou Elite Project provided by Guangzhou City, China for financial support. The authors acknowledge Diamond Light Source for access to beamlines I19 (CY21726) and I11 (EE17193). Via GMD's membership of the UK′s HEC Materials Chemistry Consortium, which is funded by the EPSRC (EP/L000202, EP/R029431), this work used the ARCHER UK National Supercomputing Service ( http://www.archer.ac.uk ). C. Zhao acknowledges the financial support received from the China Scholarships Council (No. 201806740038). Publisher Copyright: {\textcopyright} 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH",

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AU - McKie, Katherine

AU - Roper, Mark G.

AU - Day, Graeme M.

AU - Liu, Ming

AU - Cooper, Andrew I.

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AB - Ethyl acetate is an important chemical raw material and solvent. It is also a key volatile organic compound in the brewing industry and a marker for lung cancer. Materials that are highly selective toward ethyl acetate are needed for its separation and detection. Here, we report a trianglimine macrocycle (TAMC) that selectively adsorbs ethyl acetate by forming a solvate. Crystal structure prediction showed this to be the lowest energy solvate structure available. This solvate leaves a metastable, “templated” cavity after solvent removal. Adsorption and breakthrough experiments confirmed that TAMC has adequate adsorption kinetics to separate ethyl acetate from azeotropic mixtures with ethanol, which is a challenging and energy-intensive industrial separation.

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Inherent Ethyl Acetate Selectivity in a Trianglimine Molecular Solid

Abstract

Keywords

ASJC Scopus subject areas

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