Tetra-n-butylphosphonium type ionic liquids with fumarate anion and maleate anion exhibit different physico-chemical properties and different solubility to water in their cis and trans conformations; fumarate showed the usual upper critical solution temperature (UCST) behavior, whereas maleate had highly unusual lower critical solution temperature (LCST) behavior after mixing with water.
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Fukaya et al. (2007) studied this question.
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