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( Rey Eliseo C. Torrejos ),( Grace M. Nisola ),( Sang Hoon Min ),( Jeong Woo Han ),( Khino J. Parohinog ),( Seongpoong Lee ),( Wook-jin Chung ) 한국폐기물자원순환학회(구 한국폐기물학회) 2019 ISSE 초록집 Vol.2019 No.-
Dihydroxy-dithia-, -trithia-, and -tetrathia-14-crown-4 ether derivatives (2g-2m) were effectively synthesized by bis-epoxide ring-opening cyclization reaction with 1,2-benzenedithiol using a mild base triethylamine and LiCl as template in water. Experimental liquid-liquid extraction (LLE) and density functional theory (DFT) calculations reveal that the cavity size and denticity of the synthesized thiacrown ethers (CEs) affected their selectivity towards palladium (Pd) and platinum (Pt). Among the CE derivatives, bidentate dihydroxy-dibenzo-dioxadithia-14-crown ether (2i) with a calculated cavity size of 1.58-1.65 Ǻ was most selective towards Pd (1.56 Ǻ) whereas tetradentate dihydroxy-benzo-dimethyl-tetrathia-14-crown-4 ether (2m) with a cavity size of 1.31-1.60 Ǻ towards Pt (1.48 Ǻ), due to the CE cavity size-match relationship. The metals, M<sup>n+</sup> (Pd or Pt) are situated perfectly inside the CE cavity with an S4 CE-M<sup>n+</sup>complex coordination geometry and the lowest DFT calculated binding energies (ΔE<sub>CE-M</sub> <sup>n+</sup>).The dihydroxy thiacrown ethers can be further modified by alkylation for LLE application or polymerized via epoxy functionalization for solid-liquid extraction application of Pd or Pt from highly acidic auto-catalyst leachate. LLE performance of 2i in toluene-water system showed 99.99% Pd extraction efficiency with selectivity up to 10<sup>5</sup> in comparison to other competing metals from highly acidic auto-catalyst leachate. Epoxy-polymerization of epoxide functionalized CEs with diamine as curing agent to afford highly selective adsorbents for Pd or Pt separation were also investigated and showed excellent Pd and Pt separation performance. This work was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (No. 2017R1D1A1B03028102).