Sample preparation Synthesis of Protic Phosphonium cation based ILs Tributyl phosphonium bis(trifluoromethane sulphonyl) amide (P 444H NTf 2 ) was synthesized via reaction scheme 1. Scheme 1 A typical procedure for synthesis of P 444H NTf 2 is as follows: 6.0 g (0.021 mol) LiNTf 2 (3M, all chemicals were used as received, except as otherwise specified) was dissolved in 5 ml distilled water, 5.0 g (0.021 mol) tri-isobutyl phosphonium chloride (Cytec) was dissolved in 20 ml distilled water, these

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... two solutions were mixed and the mixture was stirred at room temperature for about 3 hrs; P 444H NTf 2 was deposited as white solid from the solution, separated by filtering and washed with distilled water for three times; the product was dried by vacuum at ~70 °C; 9 g of P 444H NTf 2 was obtained with a yield of 92 %. Electrospray mass spectroscopy (cone ±35V), m/z (relative intensity, %): ES + , 203.3 ([C 4 H 9 ] 3 HP + , 100); ES -, 279.9 ([CF 3 SO 2 ] 2 N -, 100). H 1 NMR (400.