Development of a homogeneous/heterogeneous metal recovery system based on reversible association/dissociation between tris(2-aminoethyl)amine and 1,4-bis(hexafluoro-α-hydroxyisopropyl)benzene
Abstract We developed a novel metal recovery system that facilitates homogeneous coordination for metal recovery and then becomes heterogeneous, allowing separation after the recovery, based on reversible association/dissociation between tris(2-aminoethyl)amine (denoted as tren) and 1,4-bis(hexafluoro-α-hydroxyisopropyl)benzene (1,4-bisHFAB). Metal solution containing the tren/1,4-bisHFAB association complex is homogeneous at high temperature due to the scission of hydrogen bonds, which results in efficient coordination of tren to the metal ions. After coordination, the solution is heterogenized by cooling, which results in the regeneration of hydrogen bonds, and the mixture can be separated by filtration. The recovery behavior of Pd(OAc) 2 and CuBr(PPh 3 ) 3 using this system was examined, and the recovery efficiencies were found to be high (Pd II : 100% and Cu I : 100%). The system also allowed the recovery of Pd(OAc) 2 and CuBr(PPh 3 ) 3 catalysts after Suzuki-Miyaura coupling and Huisgen cycloaddition, respectively (Pd II : 100% and Cu I : 100%). Highlights Homogeneous coordination for metal recovery and then heterogeneous for separation. Recovery efficiencies of Pd II and Cu I were high (>99%). Recovery efficiency reached >99% even with a time of just 10s. Recovery of metal catalyst after Suzuki-Miyaura coupling and Huisgen cycloaddition. Graphical abstract [DISPLAY OMISSION]
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