Inherent Ethyl Acetate Selectivity in a Trianglimine Molecular Solid. Issue 41 (27th May 2021)

• Record Type: Journal Article
• Authors: He, Donglin; Zhao, Chengxi; Chen, Linjiang; Little, Marc A.; Chong, Samantha Y.; Clowes, Rob; McKie, Katherine; Roper, Mark G.; Day, Graeme M.; Liu, Ming; Cooper, Andrew I.
• Is Part Of: Chemistry. Volume 27:Issue 41(2021)
• Page Start: 10589
• Page End: 10594
• Publication Date: 2021-05-27
• Subjects: crystal structure prediction -- dynamic separation -- macrocycles -- molecular crystals -- selective adsorption; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202101510
• Languages: English
• ISSNs: 0947-6539

Abstract

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. Abstract : The separation of ethyl acetate from its azeotropic mixtures with ethanol is of great importance in the industrial production of ethyl acetate. Current purification techniques include extractive distillation and azeotropic distillation are energy‐intensive. Guided by crystal structure prediction, a "templating" strategy was used to construct selective binding sites in a trianglimine macrocycle crystal for the solvent molecule. These crystals exhibit inherently high selectivity towards ethyl acetate, reasonable kinetics, and show promise for real‐life, practical dynamic separations.