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2 protocols using 1 butyl 3 methylimidazolium nitrate

1

Synthesis of Ionic Liquids and Reagents

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Acetonitrile
(99.9%), dichloromethane (99.8%), ethyl acetate (99.5%), 1-methylimidazole
(99%), 1-bromodecane (98%), 1-chlorobutane (98%), hexane (99.7%),
1-hexene (99.8%), 2-hexyne (99%), methyl tiglate (99%), PEG, silver
nitrate ([Ag+][NO3], 99%),
[Ag+][NTf2] (97%), silver
tetrafluoroborate ([Ag+][BF4], 98%), silver trifluoromethanesulfonate ([Ag+][TfO], 99%), 1-butyl-3-methylimidazolium nitrate ([BMIM+][NO3], 95%), [BMIM+][TfO] (95%), and [BMIM+][BF4] (97%) were purchased from Sigma-Aldrich (St.
Louis, MO, USA). Sodium tetrafluoroborate ([Na+][BF4], 97%) was purchased from Acros Organics
(Morris Plains, NJ, USA). [Li+][NTf2] (99.5%) salt was obtained from SynQuest Laboratories (Alachua,
FL, USA). Naphthalene (98%) and untreated fused silica capillary tubing
(I.D. 250 μm) were purchased from Supelco (Bellefonte, PA, USA).
All chemicals were used as received.
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2

Synthesis of Metal Complexes

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All chemicals of reagent grade quality were obtained from commercial sources and used without further purification. CoSO4·6H2O (50.0 mmol), Ce(NO3)3·6H2O (50.0 mmol), NiSO4·6H2O (50.0 mmol), and CuSO4·5H2O (50.0 mmol) were purchased from Merck (Milipore, Darmstadt, Germany). 1-Hydroxyethane-1,1-diphosphonic acid, sodium hydroxide, 1-butyl-3-methylimidazolium trifluoromethanesulfonate, 1-butyl-3-methylimidazolium nitrate, 1-butyl-3-methylimidazolium chloride, 1-hexyl-3-methyl-imidazolium chloride, 2,6-dimethylphenol, and 4,4′-dihydroxybiphenyl were obtained from Sigma-Aldrich Chemie GmbH (München, Germany), and urea from Alfa Aesar (Karlsruhe, Germany).
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