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Inherent ethyl acetate selectivity in a trianglimine molecular solid

Inherent ethyl acetate selectivity in a trianglimine molecular solid
Inherent ethyl acetate selectivity in a trianglimine molecular solid
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.
0947-6539
10589-10594
He, Donglin
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Zhao, Chengxi
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Chen, Linjiang
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Little, M.A.
268d77e5-79dc-49ed-91da-2f3fe19299e9
Chong, Samantha Y.
2e23eea0-c8eb-48bb-8e69-7f3a50d0e812
Clowes, Rob
11e42a35-d9b1-44be-84af-10a5bac63b00
Katherine, McKie
0e7d289b-f805-417c-86b1-baad6e904ac1
Mark G., Roper
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Day, Graeme M.
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Liu, Ming
7479eb11-ab96-437f-bcc0-f7f6294563c8
Cooper, Andrew I.
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He, Donglin
4f764eb9-1ea9-4eb5-a08d-635e7ae52d7f
Zhao, Chengxi
93801e81-0a4a-4543-9128-69fbb727e7b0
Chen, Linjiang
112dafcc-0bcc-44c0-8441-11c02f048aa4
Little, M.A.
268d77e5-79dc-49ed-91da-2f3fe19299e9
Chong, Samantha Y.
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Clowes, Rob
11e42a35-d9b1-44be-84af-10a5bac63b00
Katherine, McKie
0e7d289b-f805-417c-86b1-baad6e904ac1
Mark G., Roper
19ed6ece-4475-4417-aa19-a5e0534d5560
Day, Graeme M.
e3be79ba-ad12-4461-b735-74d5c4355636
Liu, Ming
7479eb11-ab96-437f-bcc0-f7f6294563c8
Cooper, Andrew I.
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He, Donglin, Zhao, Chengxi, Chen, Linjiang, Little, M.A., Chong, Samantha Y., Clowes, Rob, Katherine, McKie, Mark G., Roper, Day, Graeme M., Liu, Ming and Cooper, Andrew I. (2021) Inherent ethyl acetate selectivity in a trianglimine molecular solid. Chemistry - A European Journal, 27 (41), 10589-10594. (doi:10.1002/chem.202101510).

Record type: Article

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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Inherent Selectivity in Trianglimine Solid - Accepted Manuscript
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Accepted/In Press date: 28 April 2021
e-pub ahead of print date: 30 April 2021
Published date: 21 July 2021

Identifiers

Local EPrints ID: 448871
URI: http://eprints.soton.ac.uk/id/eprint/448871
ISSN: 0947-6539
PURE UUID: f751d192-8f8e-4efd-847f-6121cf1503b3
ORCID for Graeme M. Day: ORCID iD orcid.org/0000-0001-8396-2771

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Date deposited: 07 May 2021 16:32
Last modified: 17 Mar 2024 03:29

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Contributors

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

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