Selective Solid–Liquid and Liquid–Liquid Extraction of Lithium Chloride Using Strapped Calix[4]pyrroles

Qing He; Neil J. Williams; Ju Hyun Oh; Vincent M. Lynch; Sung Kuk Kim; Bruce A. Moyer; Jonathan L. Sessler

doi:10.1002/anie.201805127

Selective Solid–Liquid and Liquid–Liquid Extraction of Lithium Chloride Using Strapped Calix[4]pyrroles

Qing He, Neil J. Williams, Ju Hyun Oh, Vincent M. Lynch, Sung Kuk Kim, Bruce A. Moyer, Jonathan L. Sessler

Chemical Separations Group

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

87 Scopus citations

Abstract

LiCl is a classic “hard” ion salt that is present in lithium-rich brines and a key component in end-of-life materials (that is, used lithium-ion batteries). Its isolation and purification from like salts is a recognized challenge with potential strategic and economic implications. Herein, we describe two ditopic calix[4]pyrrole-based ion-pair receptors (2 and 3), that are capable of selectively capturing LiCl. Under solid–liquid extraction conditions, using 2 as the extractant, LiCl could be separated from a NaCl/KCl salt mixture containing as little as 1 % LiCl with circa 100 % selectivity, while receptor 3 achieved similar separations when the LiCl level was as low as 200 ppm. Under liquid–liquid extraction conditions using nitrobenzene as the non-aqueous phase, the extraction preference displayed by 2 is KCl>NaCl>LiCl. In contrast, 3 exhibits high selectivity towards LiCl over NaCl and KCl, with no appreciable extraction being observed for the latter two salts.

Original language	English
Pages (from-to)	11924-11928
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	57
Issue number	37
DOIs	https://doi.org/10.1002/anie.201805127
State	Published - Sep 10 2018

Funding

The work in Austin was supported by the Office of Basic Energy Sciences, U.S. Department of Energy (DOE) (grant DE-FG02-01ER15186 to J.L.S.). S.K.K. acknowledges the Basic Science Research Program of the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT & Future Planning (2017R1A4A1014595). Support from the Robert A. Welch Foundation (F-0018 to J.L.S.) is also acknowledged. B.A.M. (advice on binding and extractions) and N.J.W. (supporting extraction measurements) acknowledge support by the U.S. Department of Energy, Office of Science, Basic Energy Sciences, Chemical Sciences, Geosciences, and Biosciences Division.

Funders	Funder number
Basic Energy Sciences
National Research Foundation of Korea
Office of Basic Energy Sciences
U.S. Department of Energy	DE-FG02-01ER15186
Office of Science
Basic Energy Sciences
Chemical Sciences, Geosciences, and Biosciences Division
Ministry of Science, ICT and Future Planning	2017R1A4A1014595
National Research Foundation of Korea

Keywords

calix[4]pyrrole
ion-pair receptors
liquid–liquid extraction
lithium chloride
solid–liquid extraction

UN SDGs

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

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10.1002/anie.201805127

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title = "Selective Solid–Liquid and Liquid–Liquid Extraction of Lithium Chloride Using Strapped Calix[4]pyrroles",

abstract = "LiCl is a classic “hard” ion salt that is present in lithium-rich brines and a key component in end-of-life materials (that is, used lithium-ion batteries). Its isolation and purification from like salts is a recognized challenge with potential strategic and economic implications. Herein, we describe two ditopic calix[4]pyrrole-based ion-pair receptors (2 and 3), that are capable of selectively capturing LiCl. Under solid–liquid extraction conditions, using 2 as the extractant, LiCl could be separated from a NaCl/KCl salt mixture containing as little as 1 % LiCl with circa 100 % selectivity, while receptor 3 achieved similar separations when the LiCl level was as low as 200 ppm. Under liquid–liquid extraction conditions using nitrobenzene as the non-aqueous phase, the extraction preference displayed by 2 is KCl>NaCl>LiCl. In contrast, 3 exhibits high selectivity towards LiCl over NaCl and KCl, with no appreciable extraction being observed for the latter two salts.",

keywords = "calix[4]pyrrole, ion-pair receptors, liquid–liquid extraction, lithium chloride, solid–liquid extraction",

author = "Qing He and Williams, {Neil J.} and Oh, {Ju Hyun} and Lynch, {Vincent M.} and Kim, {Sung Kuk} and Moyer, {Bruce A.} and Sessler, {Jonathan L.}",

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AU - He, Qing

AU - Williams, Neil J.

AU - Oh, Ju Hyun

AU - Lynch, Vincent M.

AU - Kim, Sung Kuk

AU - Moyer, Bruce A.

AU - Sessler, Jonathan L.

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N2 - LiCl is a classic “hard” ion salt that is present in lithium-rich brines and a key component in end-of-life materials (that is, used lithium-ion batteries). Its isolation and purification from like salts is a recognized challenge with potential strategic and economic implications. Herein, we describe two ditopic calix[4]pyrrole-based ion-pair receptors (2 and 3), that are capable of selectively capturing LiCl. Under solid–liquid extraction conditions, using 2 as the extractant, LiCl could be separated from a NaCl/KCl salt mixture containing as little as 1 % LiCl with circa 100 % selectivity, while receptor 3 achieved similar separations when the LiCl level was as low as 200 ppm. Under liquid–liquid extraction conditions using nitrobenzene as the non-aqueous phase, the extraction preference displayed by 2 is KCl>NaCl>LiCl. In contrast, 3 exhibits high selectivity towards LiCl over NaCl and KCl, with no appreciable extraction being observed for the latter two salts.

AB - LiCl is a classic “hard” ion salt that is present in lithium-rich brines and a key component in end-of-life materials (that is, used lithium-ion batteries). Its isolation and purification from like salts is a recognized challenge with potential strategic and economic implications. Herein, we describe two ditopic calix[4]pyrrole-based ion-pair receptors (2 and 3), that are capable of selectively capturing LiCl. Under solid–liquid extraction conditions, using 2 as the extractant, LiCl could be separated from a NaCl/KCl salt mixture containing as little as 1 % LiCl with circa 100 % selectivity, while receptor 3 achieved similar separations when the LiCl level was as low as 200 ppm. Under liquid–liquid extraction conditions using nitrobenzene as the non-aqueous phase, the extraction preference displayed by 2 is KCl>NaCl>LiCl. In contrast, 3 exhibits high selectivity towards LiCl over NaCl and KCl, with no appreciable extraction being observed for the latter two salts.

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JO - Angewandte Chemie - International Edition

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ER -

Selective Solid–Liquid and Liquid–Liquid Extraction of Lithium Chloride Using Strapped Calix[4]pyrroles

Abstract

Funding

Keywords

UN SDGs

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