Solvent extraction of aqueous alkali and some heavy metal picrates with the title compounds showed that, with most cations except for Li+, Na+, and Ag+, the extractability decreases monotonically as the ring size increases from 12 to 16. However, 14-crown-4 showed the highest extractability and selectivity for Li+ over the larger alkali metals, while 15-crown-4 exhibited the highest Ag+/TI+ selectivity.
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Liu et al. (1990) studied this question.
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