interactions between the thiophene and the aromatic core of the ILs cation 28

Interactions between the thiophene and the aromatic

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interactions between the thiophene and the aromatic core of the ILs cation. 28 The solubility values of heptane and thiophene in the studied ILs are represented by the first and last tie-lines (IL-rich phase). The large difference between heptane and thiophene solubility in the ILs indicates that both [ 1 E 3 M 5 M 2 PPy][NTf 2 ] and [ 1 B 3 M 5 M 2 PPy][NTf 2 ] could achieve a good extraction of thiophene from heptane. Comparison of heptane solubility in both ILs shows that it is more soluble in [ 1 B 3 M 5 M 2 PPy][NTf 2 ] ( x 1 = 0.242) than in [ 1 E 3 M 5 M 2 PPy][NTf 2 ] ( x 1 = 0.156), which indicates that an increase in the alkyl chain length located in position 1, leads to a higher alkane solubility. 2770 | Green Chem. , 2011, 13 , 2768–2776 This journal is © The Royal Society of Chemistry 2011 Published on 18 August 2011. Downloaded by Memorial University of Newfoundland on 12/22/2018 10:10:24 PM. View Article Online
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Table 3 Experimental liquid–liquid equilibrium data in mole fraction, and values of the solute distribution ratio ( b ) and selectivity ( S ) for the ternary systems (heptane (1) + thiophene (2) + [ 1 E 3 M 5 M 2 PPy][NTf 2 ] (3)) at T = 298.15 K and atmospheric pressure Alkane-rich phase (I) Ionic liquid-rich phase (II) x 1 x 2 x 3 x 1 x 2 x 3 b S 1.000 0.000 0.000 0.156 0.000 0.844 0.983 0.017 0.000 0.152 0.077 0.771 4.53 29.29 0.942 0.058 0.000 0.124 0.199 0.677 3.43 26.06 0.924 0.076 0.000 0.124 0.248 0.628 3.26 24.32 0.885 0.115 0.000 0.109 0.325 0.566 2.83 22.95 0.809 0.191 0.000 0.094 0.427 0.479 2.24 19.24 0.740 0.260 0.000 0.094 0.504 0.402 1.94 15.26 0.621 0.379 0.000 0.085 0.590 0.325 1.56 11.37 0.500 0.500 0.000 0.083 0.647 0.270 1.29 7.80 0.356 0.644 0.000 0.078 0.709 0.213 1.10 5.02 0.205 0.795 0.000 0.069 0.775 0.156 0.97 2.90 0.062 0.938 0.000 0.035 0.838 0.127 0.89 1.58 0.000 1.000 0.000 0.000 0.889 0.111 0.89 Table 4 Experimental liquid–liquid equilibrium data in mole fraction, and values of the solute distribution ratio ( b ) and selectivity ( S ) for the ternary systems (heptane (1) + thiophene (2) + [ 1 B 3 M 5 M 2 PPy][NTf 2 ] (3)) at T = 298.15 K and atmospheric pressure Alkane-rich phase (I) Ionic liquid-rich phase (II) x 1 x 2 x 3 x 1 x 2 x 3 b S 1.000 0.000 0.000 0.242 0.000 0.758 0.987 0.013 0.000 0.225 0.069 0.706 5.31 23.28 0.967 0.033 0.000 0.207 0.139 0.654 4.21 19.68 0.934 0.066 0.000 0.175 0.242 0.583 3.67 19.57 0.883 0.117 0.000 0.141 0.355 0.504 3.03 19.00 0.823 0.177 0.000 0.149 0.426 0.425 2.41 13.29 0.626 0.374 0.000 0.126 0.591 0.283 1.58 7.85 0.499 0.501 0.000 0.120 0.657 0.223 1.31 5.45 0.407 0.593 0.000 0.111 0.694 0.195 1.17 4.29 0.284 0.716 0.000 0.097 0.744 0.159 1.04 3.04 0.130 0.870 0.000 0.064 0.819 0.117 0.94 1.91 0.054 0.946 0.000 0.032 0.867 0.101 0.92 1.55 0.000 1.000 0.000 0.000 0.910 0.090 0.91 Fig. 1 Experimental and correlated tie-lines for the LLE at 25 C for the ternary system (heptane + thiophene + [ 1 E 3 M 5 M 2 PPy][NTf 2 ]). Solid lines and full points indicate experimental tie-lines, and dashed lines and empty squares indicate calculated data from NRTL model. The solubility of thiophene is shown to be also higher in [ 1 B 3 M 5 M 2 PPy][NTf 2 ] ( x 2 = 0.910) than in [ 1 E 3 M 5 M 2 PPy][NTf 2 ] ( x 2 = 0.889), although in this case the difference is not so large. Similar behaviour was shown by Arce et al. studying the Fig. 2 Experimental and correlated tie-lines for the LLE at 25 C for the ternary system (heptane + thiophene + [ 1 B 3 M 5 M 2 PPy][NTf 2 ]). Solid lines and full points indicate experimental tie-lines, and dashed lines and empty squares indicate calculated data from NRTL model. separation of benzene from hexane by extraction with several 1- alkyl-3-methylimidazolium bis(trifluoromethanelsulfonyl)imide ILs as solvents. 29 This journal is © The Royal Society of Chemistry 2011 Green Chem. , 2011, 13 , 2768–2776 | 2771 Published on 18 August 2011. Downloaded by Memorial University of Newfoundland on 12/22/2018 10:10:24 PM.
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