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Updated: Jun 26, 2025

Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants
Published on: October 19, 2017
Comprehensive extraction study using N,N-dioctylthiodiglycolamic acid: effect of S donor on metal extraction
Kojiro Shimojo1, Iori Fujiwara2,3, Takumi Saito4
1Materials Sciences Research Center, Japan Atomic Energy Agency (JAEA), 1-1-1 Koto, Sayo-cho, Sayo-gun, Hyogo, 679-5148, Japan. shimojo.kojiro@jaea.go.jp.
N,N-dioctylthiodiglycolamic acid (T-DODGAA) shows superior metal ion extraction capabilities compared to its oxygen analog, DODGAA. This sulfur-donor ligand demonstrates enhanced performance, particularly for soft metal ions, with potential applications in hydrometallurgy and metal recycling.
Area of Science:
- * Coordination Chemistry
- * Analytical Chemistry
- * Materials Science
Background:
- * Investigating novel ligands for selective metal ion extraction is crucial for advancing hydrometallurgy and recycling processes.
- * N,N-dioctylthiodiglycolamic acid (T-DODGAA), a sulfur-donor ligand, presents unique properties due to its thioether linkage.
- * Comparison with N,N-dioctyldiglycolamic acid (DODGAA), an oxygen-donor analog, provides insights into donor atom effects on extraction efficiency.
Purpose of the Study:
- * To comprehensively evaluate the metal ion extraction ability of T-DODGAA for 56 different metal ions.
- * To compare the extraction performance of T-DODGAA with DODGAA.
- * To assess the practical feasibility of T-DODGAA in selective separation of rare metal ions for hydrometallurgy and recycling.
Main Methods:
- * Potentiometric titration was employed to determine the acid dissociation constant (pKa) of T-DODGAA in an aqueous solution.
- * Solvent extraction experiments were conducted using T-DODGAA in isooctane to extract various metal ions via a proton-exchange mechanism.
- * Selective separation tests were performed on mixed metal systems, including rare metal ions.
Main Results:
- * T-DODGAA was found to be a slightly weaker acid than DODGAA, with pKa values of 3.71 and 3.54, respectively.
- * T-DODGAA demonstrated superior extraction performance over DODGAA for several metal ions, including Hf(IV), Cr(III), Fe(III), Ni(II), Cu(II), Pd(II), Ag(I), Au(III), Hg(II), Al(III), and Ga(III), especially for soft metal ions.
- * Successful selective separation of rare metal ions such as Sc(III), Ni(II), Co(II), Pd(II), Au(III), In(III), and Ga(III) was achieved in mixed-ion systems.
Conclusions:
- * T-DODGAA is an effective ligand for the extraction of a wide range of metal ions, exhibiting enhanced selectivity for soft metal ions.
- * The sulfur donor atom in T-DODGAA contributes to its superior extraction capabilities compared to the oxygen donor in DODGAA.
- * T-DODGAA shows significant potential for practical applications in hydrometallurgy and metal recycling due to its efficient and selective metal ion separation properties.
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