Thermodynamic Study of 1,4-Bis(3-methylimidazolium-1-yl)butane Bis(trifluoromethylsulfonyl)imide ([C4(MIm)2][NTf2]2) from 6 to 350 K
Abstract
:1. Introduction
2. Results and Discussion
2.1. Heat Capacity Measurements
2.2. Thermodynamic Characteristics of Fusion and the Purity Determination
2.3. Standard Thermodynamic Functions
3. Materials and Methods
3.1. Synthesis of the Bromide Precursor ([C4(MIm)2][Br]2)
3.2. Synthesis of the Test Compound ([C4(MIm)2][NTf2]2)
3.3. Heat Capacity Experiments
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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T/K | Cp | T/K | Cp | T/K | Cp |
---|---|---|---|---|---|
Series 1 | |||||
6.52 | 14.1 | 17.14 | 67.49 | 47.73 | 220.5 |
6.85 | 14.7 | 17.61 | 70.68 | 49.37 | 226.6 |
7.22 | 16.1 | 18.09 | 73.60 | 51.01 | 232.6 |
7.52 | 17.1 | 18.57 | 76.49 | 52.66 | 238.5 |
7.81 | 18.3 | 19.05 | 79.79 | 54.31 | 244.5 |
8.21 | 19.6 | 19.53 | 83.09 | 56.40 | 251.7 |
8.74 | 21.4 | 20.01 | 86.29 | 58.11 | 257.3 |
9.21 | 23.7 | 20.99 | 92.56 | 60.12 | 263.9 |
9.78 | 25.8 | 22.45 | 102.1 | 61.81 | 269.1 |
10.33 | 28.2 | 23.94 | 110.9 | 63.62 | 274.8 |
10.89 | 30.3 | 25.45 | 120.0 | 65.11 | 279.4 |
11.35 | 32.7 | 26.98 | 128.7 | 66.31 | 282.8 |
11.84 | 35.0 | 28.51 | 137.8 | 67.63 | 286.7 |
12.14 | 36.4 | 30.07 | 145.0 | 69.30 | 291.2 |
12.61 | 38.8 | 31.64 | 153.3 | 71.17 | 296.8 |
13.08 | 41.9 | 33.21 | 161.1 | 73.23 | 302.3 |
13.44 | 43.5 | 34.80 | 167.8 | 75.42 | 307.6 |
13.90 | 46.1 | 36.39 | 175.0 | 78.25 | 315.9 |
14.35 | 49.0 | 37.99 | 182.2 | 81.23 | 323.8 |
14.81 | 52.0 | 39.60 | 188.5 | 83.84 | 330.3 |
15.27 | 55.41 | 41.21 | 195.0 | 87.31 | 338.1 |
15.73 | 57.90 | 42.84 | 201.1 | 90.88 | 347.3 |
16.20 | 60.93 | 44.46 | 207.8 | 93.85 | 355.0 |
16.67 | 64.26 | 46.35 | 215.2 | 96.81 | 362.0 |
Series 2 | |||||
83.12 | 328.0 | 149.78 | 484.5 | 236.12 | 669.0 |
85.67 | 334.8 | 151.97 | 489.5 | 240.86 | 678.9 |
87.77 | 340.0 | 154.14 | 493.8 | 245.59 | 688.3 |
89.88 | 344.9 | 156.31 | 498.1 | 250.33 | 700.1 |
91.99 | 350.4 | 158.47 | 503.9 | 255.07 | 711.4 |
94.10 | 355.4 | 160.64 | 509.6 | 260.91 | 725.5 |
96.21 | 360.6 | 162.82 | 513.8 | 265.13 | 736.3 |
98.33 | 365.9 | 164.99 | 517.5 | 269.88 | 747.5 |
100.45 | 371.2 | 167.17 | 522.9 | 274.63 | 760.7 |
102.57 | 376.5 | 169.34 | 527.7 | 279.39 | 773.3 |
104.69 | 380.8 | 171.52 | 532.1 | 284.15 | 787.4 |
106.81 | 386.3 | 173.70 | 537.0 | 288.89 | 804.2 |
108.94 | 390.9 | 175.88 | 541.1 | 293.65 | 817.5 |
111.07 | 395.9 | 178.06 | 545.3 | 298.38 | 834.1 |
113.20 | 401.3 | 180.24 | 550.0 | 303.10 | 850.9 |
115.34 | 405.8 | 182.42 | 554.7 | 307.81 | 870.5 |
117.49 | 411.0 | 184.61 | 560.0 | 312.50 | 890.8 |
119.63 | 415.6 | 186.82 | 566.0 | 317.18 | (917.5) |
121.77 | 421.4 | 189.01 | 569.8 | 321.84 | (958.9) |
123.91 | 425.8 | 191.20 | 574.4 | 326.35 | (1190) |
126.06 | 430.4 | 193.39 | 579.2 | 329.23 | (3998) |
128.21 | 435.7 | 196.12 | 586.2 | 331.24 | (9457) |
130.36 | 441.0 | 199.21 | 592.6 | 333.21 | (12,079) |
132.51 | 446.0 | 202.88 | 598.2 | 334.03 | (15,155) |
134.66 | 450.6 | 206.10 | 603.3 | 334.15 | (23,042) |
136.82 | 455.5 | 209.67 | 610.2 | 334.37 | (9651) |
138.98 | 460.0 | 213.71 | 619.0 | 336.21 | 1011 |
141.14 | 465.4 | 217.81 | 628.1 | 339.24 | 1013 |
143.29 | 469.6 | 222.02 | 637.8 | 342.21 | 1017 |
145.45 | 475.1 | 226.73 | 651.0 | ||
147.62 | 480.1 | 231.41 | 659.7 | ||
Series 3 | |||||
316.69 | 994 | 330.21 | 1007 | 345.41 | 1021 |
318.74 | 997 | 332.90 | 1008 | 347.51 | 1025 |
321.12 | 1000 | 335.42 | 1010 | 350.12 | 1032 |
323.49 | 1000 | 338.21 | 1013 | ||
327.52 | 1006 | 342.42 | 1017 | ||
Series 4 | |||||
266.13 | 738.0 | 327.28 | 1060 | 337.42 | 70,215 |
269.33 | 749.0 | 330.73 | 1280 | 337.48 | 72,541 |
271.92 | 754.0 | 331.80 | 1351 | 337.58 | 85,145 |
275.02 | 763.0 | 332.80 | 1460 | 337.58 | 120,451 |
278.42 | 771.0 | 334.65 | 1740 | 337.59 | 200,471 |
281.52 | 780.0 | 335.78 | 2011 | 337.60 | 243,321 |
284.34 | 788.0 | 336.52 | 4655 | 337.61 | 281,541 |
287.91 | 800.2 | 336.72 | 8858 | 337.64 | 180,451 |
290.31 | 808.0 | 336.82 | 9501 | 337.67 | 92,514 |
294.12 | 820.0 | 336.99 | 14,214 | 337.74 | 10,012 |
297.01 | 836.0 | 337.13 | 15,111 | 337.78 | 1010 |
308.54 | 880.0 | 337.24 | 22,154 | 338.82 | 1014 |
311.90 | 888.9 | 337.29 | 27,581 | 340.52 | 1015 |
316.27 | 915.9 | 337.37 | 30,145 | ||
320.16 | 956.7 | 337.40 | 35,214 |
T°i1/K | T°f1/K | ΔH°1/J | ΔH°2/J | ΔH°3/J g−1 | ΔH°4/J g−1 | ΔfusH°/J mol−1 |
---|---|---|---|---|---|---|
281.21 | 342.58 | 155.52 | 78.35 | 63.21 | 6.108 | 52,520 |
280.34 | 345.24 | 162.98 | 82.91 | 64.08 | 9.466 | 53,220 |
285.32 | 347.15 | 157.51 | 79.19 | 59.08 | 12.09 | 52,655 |
Mean value: | ||||||
(52.79 ± 0.28) kJ mol−1 |
T°F (exp.)/K | F | F−1 | T°F (calc.)/K |
---|---|---|---|
336.52 | 0.1276 | 7.835 | 336.52 |
336.72 | 0.1494 | 6.696 | 336.72 |
336.82 | 0.1645 | 6.078 | 336.82 |
336.99 | 0.2004 | 4.989 | 337.01 |
337.13 | 0.2350 | 4.255 | 337.14 |
337.24 | 0.2728 | 3.666 | 337.24 |
337.29 | 0.2943 | 3.398 | 337.29 |
337.37 | 0.3393 | 2.947 | 337.37 |
337.40 | 0.3538 | 2.826 | 337.39 |
337.42 | 0.3768 | 2.654 | 337.42 |
337.48 | 0.4528 | 2.209 | 337.50 |
337.58 | 0.5966 | 1.676 | 337.59 |
1 | 1.000 | 337.70 | |
∞ | 0.000 | 337.88 |
T/K | C°p(T)/J K−1 mol−1 | [H°(T) − H°(0)]/kJ mol−1 | S°(T)/J K−1 mol−1 | −[G°(T) − H°(0)]/kJ mol−1 |
---|---|---|---|---|
Solid | ||||
5 | 7.46 | 0.00995 | 2.68 | 0.00342 |
15 | 53.2 | 0.290 | 29.20 | 0.148 |
20 | 86.12 | 0.6383 | 48.99 | 0.3415 |
25 | 117.5 | 1.149 | 71.64 | 0.6424 |
30 | 145.1 | 1.807 | 95.56 | 1.060 |
35 | 168.9 | 2.593 | 119.8 | 1.598 |
40 | 190.1 | 3.491 | 143.7 | 2.257 |
45 | 210.0 | 4.492 | 167.3 | 3.035 |
50 | 228.9 | 5.590 | 190.4 | 3.929 |
60 | 263.6 | 8.056 | 235.3 | 6.059 |
70 | 293.2 | 10.84 | 278.2 | 8.628 |
80 | 320.2 | 13.91 | 319.1 | 11.62 |
90 | 345.4 | 17.24 | 358.3 | 15.00 |
100 | 370.0 | 20.82 | 396.0 | 18.78 |
110 | 393.6 | 24.64 | 432.3 | 22.92 |
120 | 416.7 | 28.69 | 467.6 | 27.42 |
130 | 439.9 | 32.97 | 501.8 | 32.27 |
140 | 462.8 | 37.49 | 535.3 | 37.45 |
150 | 485.1 | 42.23 | 568.0 | 42.97 |
160 | 507.0 | 47.19 | 600.0 | 48.82 |
170 | 528.7 | 52.37 | 631.4 | 54.97 |
180 | 550.3 | 57.76 | 662.2 | 61.44 |
190 | 572.0 | 63.37 | 692.5 | 68.21 |
200 | 593.3 | 69.20 | 722.4 | 75.29 |
210 | 611.6 | 75.22 | 751.8 | 82.66 |
220 | 633.7 | 81.45 | 780.8 | 90.32 |
230 | 655.9 | 87.89 | 809.4 | 98.27 |
240 | 677.6 | 94.56 | 837.8 | 106.5 |
250 | 699.6 | 101.4 | 865.9 | 115.0 |
260 | 722.7 | 108.6 | 893.8 | 123.8 |
270 | 748.0 | 115.9 | 921.5 | 132.9 |
280 | 775.8 | 123.6 | 949.2 | 142.3 |
290 | 806.3 | 131.5 | 977.0 | 151.9 |
298.15 | 836.0 | 138.1 | 999.7 | 159.9 |
300 | 841.8 | 139.7 | 1005 | 161.8 |
310 | 874.4 | 148.3 | 1033 | 172.0 |
320 | 907.0 | 157.2 | 1061 | 182.5 |
330 | 939.6 | 166.4 | 1090 | 193.2 |
337.88 | 963.8 | 173.9 | 1112 | 201.9 |
Liquid | ||||
337.88 | 1012 | 226.7 | 1269 | 201.9 |
340 | 1014 | 228.9 | 1275 | 204.6 |
350 | 1032 | 239.1 | 1304 | 217.5 |
Chemical Name | Source | Purification Method | Purity/% | Analysis Method |
---|---|---|---|---|
1,4-bis(3-methylimidazolium-1-yl)butane bis(trifluoromethylsulfonyl)imide [C4(MIm)2][NTf2]2 | Synthesis | Repeated washing with water; drying in vacuum | >99.0 (mole fraction) | 1H NMR spectroscopy, TG analysis, adiabatic calorimetry |
1,4-bis(3-methylimidazolium-1-yl)butane dibromide [C4(MIm)2][Br]2 | Repeated washing with ethyl acetate; drying in vacuum | 1H NMR spectroscopy | ||
1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide [C4MIm][NTf2] CAS No.: 174899-83-3 | Sigma-Aldrich | Without any purification | >99.0 (mass fraction) | — |
lithium bis(trifluoromethylsulfonyl)imide Li[NTf2] CAS No.: 90076-65-6 | ||||
1,4-dibromobutane C4H8Br2 CAS No.: 110-52-1 | ||||
1-methylimidazole C4H6N2 CAS No.: 616-47-7 | Purified by distillation |
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Markin, A.V.; Ciccioli, A.; Lapi, A.; Sologubov, S.S.; Smirnova, N.N.; Vecchio Ciprioti, S. Thermodynamic Study of 1,4-Bis(3-methylimidazolium-1-yl)butane Bis(trifluoromethylsulfonyl)imide ([C4(MIm)2][NTf2]2) from 6 to 350 K. Molecules 2024, 29, 4180. https://doi.org/10.3390/molecules29174180
Markin AV, Ciccioli A, Lapi A, Sologubov SS, Smirnova NN, Vecchio Ciprioti S. Thermodynamic Study of 1,4-Bis(3-methylimidazolium-1-yl)butane Bis(trifluoromethylsulfonyl)imide ([C4(MIm)2][NTf2]2) from 6 to 350 K. Molecules. 2024; 29(17):4180. https://doi.org/10.3390/molecules29174180
Chicago/Turabian StyleMarkin, Alexey V., Andrea Ciccioli, Andrea Lapi, Semen S. Sologubov, Natalia N. Smirnova, and Stefano Vecchio Ciprioti. 2024. "Thermodynamic Study of 1,4-Bis(3-methylimidazolium-1-yl)butane Bis(trifluoromethylsulfonyl)imide ([C4(MIm)2][NTf2]2) from 6 to 350 K" Molecules 29, no. 17: 4180. https://doi.org/10.3390/molecules29174180