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2 protocols using 3 hydroxy 2 naphthoic acid

1

Synthesis and Preparation of Metal-Humate Complexes

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The IL precursors trihexyltetradecylphosphonium chloride (95%) and 3-hydroxy-2-naphthoic acid (98%) were purchased from Sigma-Aldrich (USA), methyl-trioctylphosphonium methylcarbonate (purum, 50% in methanol) and methyl-trioctylammonium methylcarbonate (purum, 50% in methanol) from Proionic (Austria). For synthesis and sample preparations, potassium hydroxide (p.a., 85%) from Merck (Germany), methanol (HPLC grade, 99.9%), dichloromethane (HPLC grade, 99.9%), sodium chloride (99%), nitric acid (p.a., 65%), and sodium hydroxide (98%) from Panreac (Spain), and humic acid sodium salt (technical grade) from Sigma-Aldrich were used. Standard solutions of metals Ag, Cd, Co, Cu, Mn, Ni, and Pb 1,000 mg L−1 in 2–4% (w/w) HNO3, purchased from Sigma-Aldrich, were used for atomic absorption spectroscopy measurements and to prepare feed solutions. Ultra-pure water of resistivity <18.2 MΩ cm was obtained from a Millipore Milli-Q Academic apparatus (Merck Millipore, USA).
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2

Synthesis of Phosphonium-Based Ionic Liquid Precursor

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For synthesis, the IL precursor trihexyltetradecylphosphonium chloride (95%) and 3-hydroxy-2-naphthoic acid (98%) were purchased from Sigma-Aldrich (USA) along with potassium hydroxide (p.a., ≥86%) and the solvents methanol (HPLC grade, ≥99.9%) and dichloromethane (p.a., ≥99.9%). Element standard solutions of La, Ce and Lu (1000 mg L−1 ± 4) in 2% (w/w) HNO3 for the preparation of the extraction solutions were purchased from Sigma-Aldrich (USA), Nd and Ho (999 μg mL−1 ± 5) in 5% (w/w) HNO3 from AlfaAesar. The Pt standard solution (1000 mg L−1 in 10% (w/w) HCl) used for sample preparations before TXRF measurements was purchased from VWR. A 3.0 g L−1 polyvinyl alcohol (PVA) solution was prepared from hydrolysed polyvinyl alcohol (86–89%) with low molecular weight (AlfaAesar). For pH adjustment and dilutions, we used sodium hydroxide (50% (w/w) in H2O, extra pure, Acros Organics) and nitric acid (>68%, PrimarPlus-trace analysis grade, Fisher Scientific). Ultra-pure water of resistivity >18.2 MΩ cm was obtained from a Millipore Milli-Q apparatus (Merck Millipore, USA).
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