Selective Solid-liquid Extraction and Liquid-liquid Extraction of Lithium Chloride using Strapped Calix[4]pyrroles

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

doi:10.1002/anie.201805127

Title: Selective Solid-liquid Extraction and Liquid-liquid Extraction of Lithium Chloride using Strapped Calix[4]pyrroles

Journal Article · Fri May 25 00:00:00 EDT 2018 · Angewandte Chemie (International Edition)

DOI:https://doi.org/10.1002/anie.201805127· OSTI ID:1439936

He, Qing ^[1];

^[2]; Oh, Ju ^[3]; Lynch, Vincent M. ^[1]; Kim, Sung Kuk ^[3];

^[2]; Sessler, Jonathan L. ^[4]

Univ. of Texas, Austin, TX (United States)
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Chemical Sciences Division
Gyeongsang National University (GNU), Jinju (Korea). Chemistry and Research Institute of Natural Science
Univ. of Texas, Austin, TX (United States). Department of Chemistry

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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Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States); Univ. of Texas, Austin, TX (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences, and Biosciences Division

Grant/Contract Number:: AC05-00OR22725; FG02-01ER15186

OSTI ID:: 1439936

Alternate ID(s):: OSTI ID: 1455075; OSTI ID: 1598669

Journal Information:: Angewandte Chemie (International Edition), Vol. 57, Issue 37; ISSN 1433-7851

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 68 works

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Cited By (5)

Removal of Anions from Aqueous Media by Means of a Thermoresponsive Calix[4]pyrrole Amphiphilic Polymer Ji, Xiaofan; Guo, Chenxing; Chen, Wei Chemistry - A European Journal, Vol. 24, Issue 59 https://doi.org/10.1002/chem.201804335	journal	September 2018
Optimizing radionuclide sequestration in anion nanotraps with record pertechnetate sorption Sun, Qi; Zhu, Lin; Aguila, Briana Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-09630-y	journal	April 2019
Highly efficient synthesis of hydrogen-bonded aromatic tetramers as macrocyclic receptors for selective recognition of lithium ions Guo, Xuwen; Yang, Yizhou; Peng, Zhiyong Organic Chemistry Frontiers, Vol. 6, Issue 15 https://doi.org/10.1039/c9qo00612e	journal	January 2019
Cesium halide ion pair recognition by a pyrrole strapped Calix[4]pyrrole Yang, Ju Ho; Lynch, Vincent M.; Sessler, Jonathan L. Supramolecular Chemistry, Vol. 31, Issue 3 https://doi.org/10.1080/10610278.2018.1535711	journal	October 2018
The Effect of Substitution Pattern on Binding Ability in Regioisomeric Ion Pair Receptors Based on an Aminobenzoic Platform Jagleniec, Damian; Ziach, Krzysztof; Dąbrowa, Kajetan Molecules, Vol. 24, Issue 16 https://doi.org/10.3390/molecules24162990	journal	August 2019

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
36 MATERIALS SCIENCE
ion-pair receptor
solid-liquid extraction
lithium choride
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CCDC 1821810: Experimental Crystal Structure Determination: QIDHAP : aqua-(chloro)-[1,22,27,27,36,36-hexamethyl-5,18-dioxa-41,42,43,44,45,48-hexaazanonacyclo[20.9.9.47,16.123,26.128,31.132,35.137,40.010,47.013,46]octatetraconta-7(48),8,10(47),11,13(46),14,16(45),23,25,28,30,32,34,37,39-pentadecaene-6,17-dione]-lithium acetonitrile solvate He, Qing; Williams, Neil; Oh, Ju Hyun https://doi.org/10.5517/ccdc.csd.cc1z4r2y The current record is supplemented by this dataset	dataset	February 2018
CCDC 1821811: Experimental Crystal Structure Determination: QIDHET : chloro-[48,50-bis(methoxy)-1,25,30,30,39,39-hexamethyl-5,21,44,45,46,47,49-heptaazanonacyclo[23.9.9.16,10.111,15.116,20.126,29.131,34.135,38.140,43]pentaconta-6(50),7,9,11(49),12,14,16(48),17,19,26,28,31,33,35,37,40,42-heptadecaene-4,22-dione]-(methanol)-lithium acetonitrile solvate He, Qing; Williams, Neil; Oh, Ju Hyun https://doi.org/10.5517/ccdc.csd.cc1z4r3z The current record is supplemented by this dataset	dataset	February 2018
CCDC 1821812: Experimental Crystal Structure Determination: QIDHIX : (48,50-dimethoxy-1,25,30,30,39,39-hexamethyl-5,21,44,45,46,47,49-heptaazanonacyclo[23.9.9.16,10.111,15.116,20.126,29.131,34.135,38.140,43]pentaconta-6(50),7,9,11(49),12,14,16(48),17,19,26,28,31,33,35,37,40,42-heptadecaene-4,22-dione)-methanol-chloro-lithium dichloromethane acetonitrile solvate He, Qing; Williams, Neil; Oh, Ju Hyun https://doi.org/10.5517/ccdc.csd.cc1z4r40 The current record is supplemented by this dataset	dataset	February 2018
CCDC 1821813: Experimental Crystal Structure Determination: QIDHOD : 48,50-dimethoxy-1,25,30,30,39,39-hexamethyl-5,21,44,45,46,47,49-heptaazanonacyclo[23.9.9.16,10.111,15.116,20.126,29.131,34.135,38.140,43]pentaconta-6(50),7,9,11(49),12,14,16(48),17,19,26,28,31,33,35,37,40,42-heptadecaene-4,22-dione methanol solvate tetrahydrate Space Group: P 1 (2), Cell: a 11.6417(6)Å b 13.7047(7)Å c 16.6041(8)Å, α 77.987(4)° β 86.663(4)° γ 67.729(5)° He, Qing; Williams, Neil J.; Oh, Ju Hyun https://doi.org/10.5517/ccdc.csd.cc1z4r51 The current record is supplemented by this dataset	dataset	February 2018
CCDC 1821814: Experimental Crystal Structure Determination: QIDHUJ : triethylammonium flouride 48,50-dimethoxy-1,25,30,30,39,39-hexamethyl-5,21,44,45,46,47,49-heptaazanonacyclo[23.9.9.16,10.111,15.116,20.126,29.131,34.135,38.140,43]pentaconta-6(50),7,9,11(49),12,14,16(48),17,19,26,28,31,33,35,37,40, dichloromethane solvate monohydrate Space Group: P 21/c (14), Cell: a 20.7251(2)Å b 14.87716(17)Å c 22.5212(3)Å, α 90° β 90.9933(11)° γ 90° He, Qing; Williams, Neil J.; Oh, Ju Hyun https://doi.org/10.5517/ccdc.csd.cc1z4r62 The current record is supplemented by this dataset	dataset	February 2018
CCDC 1821815: Experimental Crystal Structure Determination: QIDJAR : 1,22,27,27,36,36-hexamethyl-5,18-dioxa-41,42,43,44,45,48-hexaazanonacyclo[20.9.9.47,16.123,26.128,31.132,35.137,40.010,47.013,46]octatetraconta-7,9,11,13,15,23,25,28,30,32,34,37,39,45,47-pentadecaene-6,17-dione chloroform solvate trihydrate He, Qing; Williams, Neil J.; Oh, Ju Hyun https://doi.org/10.5517/ccdc.csd.cc1z4r73 The current record is supplemented by this dataset	dataset	February 2018
CCDC 1821816: Experimental Crystal Structure Determination: QIDJEV : bis(acetonitrile)-chloro-[48,50-bis(methoxy)-1,25,30,30,39,39-hexamethyl-5,21,44,45,46,47,49-heptaazanonacyclo[23.9.9.16,10.111,15.116,20.126,29.131,34.135,38.140,43]pentaconta-6(50),7,9,11(49),12,14,16(48),17,19,26,28,31,33,35,37,40,42-heptadecaene-4,22-dione]-caesium He, Qing; Williams, Neil J.; Oh, Ju Hyun https://doi.org/10.5517/ccdc.csd.cc1z4r84 The current record is supplemented by this dataset	dataset	February 2018
CCDC 1821817: Experimental Crystal Structure Determination: QIDJIZ : potassium chloride 48,50-dimethoxy-1,25,30,30,39,39-hexamethyl-5,21,44,45,46,47,49-heptaazanonacyclo[23.9.9.16,10.111,15.116,20.126,29.131,34.135,38.140,43]pentaconta-6(50),7,9,11(49),12,14,16(48),17,19,26,28,31,33,35,37,40,42-heptadecaene-4,22-dione acetonitrile methanol solvate trihydrate Space Group: P 1 (2), Cell: a 15.4462(4)Å b 18.2070(5)Å c 38.9452(11)Å, α 82.322(2)° β 89.561(2)° γ 81.621(2)° He, Qing; Williams, Neil J.; Oh, Ju Hyun https://doi.org/10.5517/ccdc.csd.cc1z4r95 The current record is supplemented by this dataset	dataset	February 2018