Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1...
Transcript of Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1...
![Page 1: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/1.jpg)
1
Supporting Information
Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability
Farzad Atefi, M. Teresa Garcia, Robert D. Singer and Peter J. Scammells
Table of Contents 1H NMR (DMSO-d6, 300 MHz) Tricyclohexyl(propoxycarbonylmethyl)phosphonium bromide 2a 3 13C NMR (DMSO-d6, 150 MHz) Tricyclohexyl(propoxycarbonylmethyl)phosphonium bromide 2a 4 31P NMR (DMSO-d6, 121 MHz) Tricyclohexyl(propoxycarbonylmethyl)phosphonium bromide 2a 5 1H NMR (DMSO-d6, 300 MHz) Tricyclohexyl(pentoxycarbonylmethyl)phosphonium bromide 3a 6 13C NMR (DMSO-d6, 150 MHz) Tricyclohexyl(pentoxycarbonylmethyl)phosphonium bromide 3a 7 31P NMR (DMSO-d6, 121 MHz) Tricyclohexyl(pentoxycarbonylmethyl)phosphonium bromide 3a 8 1H NMR (DMSO-d6, 300 MHz) Tricyclohexyl(heptoxycarbonylmethyl)phosphonium bromide 4a 9 13C NMR (DMSO-d6, 150 MHz) Tricyclohexyl(heptoxycarbonylmethyl)phosphonium bromide 4a 10 31P NMR (DMSO-d6, 121 MHz) Tricyclohexyl(heptoxycarbonylmethyl)phosphonium bromide 4a 11 1H NMR (DMSO-d6, 300 MHz) Tricyclohexyl(acetoxybutyl))phosphonium iodide 5a 12 13C NMR (DMSO-d6, 150 MHz) Tricyclohexyl(acetoxybutyl))phosphonium iodide 5a 13 31P NMR (DMSO-d6, 121 MHz) Tricyclohexyl(acetoxybutyl))phosphonium iodide 5a 14 1H NMR (DMSO-d6, 300 MHz) Tricyclohexyl(propoxycarbonylmethyl)phosphonium triflimide 2b 15 13C NMR (DMSO-d6, 150 MHz) Tricyclohexyl(propoxycarbonylmethyl)phosphonium triflimide 2b 16 31P NMR (DMSO-d6, 121 MHz) Tricyclohexyl(propoxycarbonylmethyl)phosphonium triflimide 2b 17 1H NMR (DMSO-d6, 300 MHz) Tricyclohexyl(propoxycarbonylmethyl)phosphonium octylsulfate 2c 18 13C NMR (DMSO-d6, 150 MHz) Tricyclohexyl(propoxycarbonylmethyl)phosphonium octylsulfate 2c 19 31P NMR (DMSO-d6, 121 MHz) Tricyclohexyl(propoxycarbonylmethyl)phosphonium octylsulfate 2c 20 1H NMR (DMSO-d6, 300 MHz) Tricyclohexyl(pentoxycarbonylmethyl)phosphonium triflimide 3b 21 13C NMR (DMSO-d6, 150 MHz) Tricyclohexyl(pentoxycarbonylmethyl)phosphonium triflimide 3b 22 31P NMR (DMSO-d6, 121 MHz) Tricyclohexyl(pentoxycarbonylmethyl)phosphonium triflimide 3b 23 1H NMR (DMSO-d6, 300 MHz) Tricyclohexyl(pentoxycarbonylmethyl)phosphonium octylsulfate 3c 24 13C NMR (DMSO-d6, 150 MHz) Tricyclohexyl(pentoxycarbonylmethyl)phosphonium octylsulfate 3c 25 31P NMR (DMSO-d6, 121 MHz) Tricyclohexyl(pentoxycarbonylmethyl)phosphonium octylsulfate 3c 26 1H NMR (DMSO-d6, 300 MHz) Tricyclohexyl(heptoxycarbonylmethyl)phosphonium triflimide 4b 27 13C NMR (DMSO-d6, 150 MHz) Tricyclohexyl(heptoxycarbonylmethyl)phosphonium triflimide 4b 28 31P NMR (DMSO-d6, 121 MHz) Tricyclohexyl(heptoxycarbonylmethyl)phosphonium triflimide 4b 29 1H NMR (DMSO-d6, 300 MHz) Tricyclohexyl(heptoxycarbonylmethyl)phosphonium octylsulfate 4c 30 13C NMR (DMSO-d6, 150 MHz) Tricyclohexyl(heptoxycarbonylmethyl)phosphonium octylsulfate 4c 31 31P NMR (DMSO-d6, 121 MHz) Tricyclohexyl(heptoxycarbonylmethyl)phosphonium octylsulfate 4c 32 1H NMR (DMSO-d6, 300 MHz) Tricyclohexyl(acetoxybutyl))phosphonium triflimide 5b 33 13C NMR (DMSO-d6, 150 MHz) Tricyclohexyl(acetoxybutyl))phosphonium triflimide 5b 34 31P NMR (DMSO-d6, 121 MHz) Tricyclohexyl(acetoxybutyl))phosphonium triflimide 5b 35 1H NMR (DMSO-d6, 300 MHz) Tricyclohexyl(acetoxybutyl))phosphonium octylsulfate 5c 36 13C NMR (DMSO-d6, 150 MHz) Tricyclohexyl(acetoxybutyl))phosphonium octylsulfate 5c 37 31P NMR (DMSO-d6, 121 MHz) Tricyclohexyl(acetoxybutyl))phosphonium octylsulfate 5c 38 1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(propoxycarbonylmethyl)phosphonium bromide 7a 39 13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(propoxycarbonylmethyl)phosphonium bromide 7a 40 31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(propoxycarbonylmethyl)phosphonium bromide 7a 41 1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(pentoxycarbonylmethyl)phosphonium bromide 8a 42 13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(pentoxycarbonylmethyl)phosphonium bromide 8a 43 31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(pentoxycarbonylmethyl)phosphonium bromide 8a 44 1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(heptoxycarbonylmethyl)phosphonium bromide 9a 45 13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(heptoxycarbonylmethyl)phosphonium bromide 9a 46 31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(heptoxycarbonylmethyl)phosphonium bromide 9a 47 1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(acetoxybutyl))phosphonium iodide 10a 48 13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(acetoxybutyl))phosphonium iodide 10a 49
![Page 2: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/2.jpg)
2
31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(acetoxybutyl))phosphonium iodide 10a 50 1H NMR (DMSO-d6, 300 MHz) Tri-n-hexylallylphosphonium bromide 11a 51 13C NMR (DMSO-d6, 150 MHz) Tri-n-hexylallylphosphonium bromide 11a 52 31P NMR (DMSO-d6, 121 MHz) Tri-n-hexylallylphosphonium bromide 11a 53 1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(methoxymethyl)phosphonium chloride 12a 54 13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(methoxymethyl)phosphonium chloride 12a 55 31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(methoxymethyl)phosphonium chloride 12a 56 1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(2-hydroxyethyl)phosphonium bromide 13a 57 13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(2-hydroxyethyl)phosphonium bromide 13a 58 31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(2-hydroxyethyl)phosphonium bromide 13a 59 1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(propoxycarbonylmethyl)phosphonium triflimide 7b 60 13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(propoxycarbonylmethyl)phosphonium triflimide 7b 61 31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(propoxycarbonylmethyl)phosphonium triflimide 7b 62 1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(propoxycarbonylmethyl)phosphonium octylsulfate 7c 63 13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(propoxycarbonylmethyl)phosphonium octylsulfate 7c 64 31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(propoxycarbonylmethyl)phosphonium octylsulfate 7c 65 1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(pentoxycarbonylmethyl)phosphonium triflimide 8b 66 13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(pentoxycarbonylmethyl)phosphonium triflimide 8b 67 31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(pentoxycarbonylmethyl)phosphonium triflimide 8b 68 1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(pentoxycarbonylmethyl)phosphonium octylsulfate 8c 69 13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(pentoxycarbonylmethyl)phosphonium octylsulfate 8c 70 31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(pentoxycarbonylmethyl)phosphonium octylsulfate 8c 71 1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(heptoxycarbonylmethyl)phosphonium triflimide 9b 72 13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(heptoxycarbonylmethyl)phosphonium triflimide 9b 73 31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(heptoxycarbonylmethyl)phosphonium triflimide 9b 74 1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(heptoxycarbonylmethyl)phosphonium octylsulfate 9c 75 13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(heptoxycarbonylmethyl)phosphonium octylsulfate 9c 76 31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(heptoxycarbonylmethyl)phosphonium octylsulfate 9c 77 1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(acetoxybutyl))phosphonium triflimide 10b 78 13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(acetoxybutyl))phosphonium triflimide 10b 79 31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(acetoxybutyl))phosphonium triflimide 10b 80 1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(acetoxybutyl))phosphonium octylsulfate 10c 81 13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(acetoxybutyl))phosphonium octylsulfate 10c 82 31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(acetoxybutyl))phosphonium octylsulfate 10c 83 1H NMR (DMSO-d6, 300 MHz) Tri-n-hexylallylphosphonium triflimide 11b 84 13C NMR (DMSO-d6, 150 MHz) Tri-n-hexylallylphosphonium triflimide 11b 85 31P NMR (DMSO-d6, 121 MHz) Tri-n-hexylallylphosphonium triflimide 11b 86 1H NMR (DMSO-d6, 300 MHz) Tri-n-hexylallylphosphonium octylsulfate 11c 87 13C NMR (DMSO-d6, 150 MHz) Tri-n-hexylallylphosphonium octylsulfate 11c 88 31P NMR (DMSO-d6, 121 MHz) Tri-n-hexylallylphosphonium octylsulfate 11c 89 1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(methoxymethyl)phosphonium triflimide 12b 90 13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(methoxymethyl)phosphonium triflimide 12b 91 31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(methoxymethyl)phosphonium triflimide 12b 92 1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(methoxymethyl)phosphonium octylsulfate 12c 93 13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(methoxymethyl)phosphonium octylsulfate 12c 94 31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(methoxymethyl)phosphonium octylsulfate 12c 95 1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(2-hydroxyethyl)phosphonium triflimide 13b 96 13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(2-hydroxyethyl)phosphonium triflimide 13b 97 31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(2-hydroxyethyl)phosphonium triflimide 13b 98 1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(2-hydroxyethyl)phosphonium octylsulfate 13c 99 13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(2-hydroxyethyl)phosphonium octylsulfate 13c 100 31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(2-hydroxyethyl)phosphonium octylsulfate 13c 101
![Page 3: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/3.jpg)
3
1H NMR (DMSO-d6, 300 MHz) Tricyclohexyl(propoxycarbonylmethyl)phosphonium bromide (2a)
ppm (f1)
0.501.001.502.002.503.003.504.00
4.14
4.12
4.10
3.89
3.85
2.73
2.69
2.65
2.61
1.92
1.80
1.68
1.66
1.64
1.61
1.50
1.46
1.42
1.37
1.33
1.30
1.24
0.96
0.93
0.91
2.00
1.95
2.98
5.93
6.01
5.06
15.29
2.90
![Page 4: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/4.jpg)
4
13C NMR (DMSO-d6, 150 MHz) Tricyclohexyl(propoxycarbonylmethyl)phosphonium bromide (2a)
ppm (t1)
255075100125150
![Page 5: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/5.jpg)
5
31P NMR (DMSO-d6, 121 MHz) Tricyclohexyl(propoxycarbonylmethyl)phosphonium bromide (2a)
ppm (t1)
-75-50-250255075
35.3
![Page 6: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/6.jpg)
6
1H NMR (DMSO-d6, 300 MHz) Tricyclohexyl(pentoxycarbonylmethyl)phosphonium bromide (3a)
ppm (f1)
0.000.501.001.502.002.503.003.504.00
4.18
4.16
4.14
3.90
3.85
2.74
2.70
2.66
2.62
1.92
1.79
1.70
1.67
1.65
1.63
1.61
1.50
1.46
1.42
1.37
1.33
1.32
1.30
1.24
0.90
0.88
0.86
2.00
2.00
3.13
6.29
6.63
5.34
19.40
2.99
![Page 7: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/7.jpg)
7
13C NMR (DMSO-d6, 150 MHz) Tricyclohexyl(pentoxycarbonylmethyl)phosphonium (3a)
ppm (t1)
255075100125150
![Page 8: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/8.jpg)
8
31P NMR (DMSO-d6, 121 MHz) Tricyclohexyl(pentoxycarbonylmethyl)phosphonium bromide (3a)
ppm (f1)
-50-250255075
35.3
![Page 9: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/9.jpg)
9
1H NMR (DMSO-d6, 300 MHz) Tricyclohexyl(heptoxycarbonylmethyl)phosphonium bromide (4a)
ppm (t1)
0.501.001.502.002.503.003.504.004.50
4.17
4.15
4.13
3.88
3.84
2.73
2.69
2.65
2.61
1.92
1.79
1.70
1.67
1.62
1.60
1.50
1.46
1.41
1.37
1.32
1.30
1.28
1.26
0.86
0.84
2.00
2.00
3.17
6.34
6.59
5.39
3.19
23.63
![Page 10: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/10.jpg)
10
13C NMR (DMSO-d6, 150 MHz) Tricyclohexyl(heptoxycarbonylmethyl)phosphonium bromide (4a)
ppm (t1)
255075100125150
![Page 11: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/11.jpg)
11
31P NMR (DMSO-d6, 121 MHz) Tricyclohexyl(heptoxycarbonylmethyl)phosphonium bromide (4a)
ppm (f1)
-75-50-250255075
35.3
![Page 12: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/12.jpg)
12
1H NMR (DMSO-d6, 300 MHz) Tricyclohexyl(acetoxybutyl))phosphonium iodide (5a)
ppm (f1)
0.000.501.001.502.002.503.003.504.00
4.09
4.07
4.05
2.62
2.58
2.54
2.49
2.35
2.31
2.29
2.25
2.01
1.88
1.77
1.72
1.69
1.66
1.51
1.47
1.44
1.41
1.37
1.34
2.00
3.61
2.03
3.07
6.31
8.09
6.36
14.51
![Page 13: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/13.jpg)
13
13C NMR (DMSO-d6, 150 MHz) Tricyclohexyl(acetoxybutyl))phosphonium iodide (5a)
ppm (t1)
255075100125150
![Page 14: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/14.jpg)
14
31P NMR (DMSO-d6, 121 MHz) Tricyclohexyl(acetoxybutyl))phosphonium iodide (5a)
ppm (f1)
-50-2502550
34.2
![Page 15: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/15.jpg)
15
1H NMR (DMSO-d6, 300 MHz) Tricyclohexyl(propoxycarbonylmethyl)phosphonium triflimide (2b)
ppm (f1)
0.501.001.502.002.503.003.504.00
4.15
4.13
4.10
3.85
3.80
2.70
2.66
2.62
2.58
1.91
1.81
1.71
1.69
1.67
1.64
1.62
1.50
1.46
1.41
1.37
1.32
1.30
1.26
1.24
0.96
0.94
0.91
2.00
1.92
2.94
5.81
6.30
5.26
15.37
3.12
![Page 16: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/16.jpg)
16
13C NMR (DMSO-d6, 150 MHz) Tricyclohexyl(propoxycarbonylmethyl)phosphonium triflimide (2b)
ppm (t1)
255075100125150
![Page 17: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/17.jpg)
17
31P NMR (DMSO-d6, 121 MHz) Tricyclohexyl(propoxycarbonylmethyl)phosphonium triflimide (2b)
ppm (f1)
-50-250255075
35.2
![Page 18: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/18.jpg)
18
1H NMR (DMSO-d6, 300 MHz) Tricyclohexyl(propoxycarbonylmethyl)phosphonium octylsulfate (2c)
ppm (f1)
0.501.001.502.002.503.003.504.00
4.14
4.12
4.10
3.86
3.81
3.69
3.66
3.64
2.69
2.65
2.62
2.58
1.91
1.80
1.70
1.69
1.66
1.64
1.62
1.49
1.45
1.41
1.36
1.32
1.29
1.28
1.25
0.96
0.93
0.91
0.88
0.86
0.84
2.00
2.03
3.17
6.18
6.57
5.54
27.06
2.93
2.99
2.03
![Page 19: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/19.jpg)
19
13C NMR (DMSO-d6, 150 MHz) Tricyclohexyl(propoxycarbonylmethyl)phosphonium octylsulfate (2c)
ppm (t1)
255075100125150
![Page 20: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/20.jpg)
20
31P NMR (DMSO-d6, 121 MHz) Tricyclohexyl(propoxycarbonylmethyl)phosphonium octylsulfate (2c)
ppm (f1)
-50-250255075
35.3
![Page 21: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/21.jpg)
21
1H NMR (DMSO-d6, 300 MHz) Tricyclohexyl(pentoxycarbonylmethyl)phosphonium triflimide (3b)
ppm (f1)
0.000.501.001.502.002.503.003.504.00
4.19
4.16
4.14
3.85
3.80
2.70
2.66
2.62
2.58
1.92
1.81
1.71
1.68
1.66
1.64
1.61
1.50
1.46
1.41
1.37
1.36
1.34
1.32
1.31
1.24
0.91
0.89
0.86
2.00
1.97
3.10
6.05
6.43
5.06
19.49
3.10
![Page 22: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/22.jpg)
22
13C NMR (DMSO-d6, 150 MHz) Tricyclohexyl(pentoxycarbonylmethyl)phosphonium triflimide (3b)
ppm (t1)
255075100125150
![Page 23: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/23.jpg)
23
31P NMR (DMSO-d6, 121 MHz) Tricyclohexyl(pentoxycarbonylmethyl)phosphonium triflimide (3b)
ppm (f1)
-50-250255075
35.2
![Page 24: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/24.jpg)
24
1H NMR (DMSO-d6, 300 MHz) Tricyclohexyl(pentoxycarbonylmethyl)phosphonium octylsulfate (3c)
ppm (f1)
0.000.501.001.502.002.503.003.504.00
4.18
4.16
4.14
3.85
3.81
3.69
3.67
3.65
2.71
2.67
2.63
2.59
1.92
1.80
1.71
1.68
1.66
1.63
1.61
1.50
1.48
1.46
1.41
1.37
1.36
1.33
1.32
1.31
1.29
1.25
0.91
0.88
0.86
0.84
2.00
1.95
2.10
3.04
6.09
6.42
5.28
31.66
6.26
![Page 25: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/25.jpg)
25
13C NMR (DMSO-d6, 150 MHz) Tricyclohexyl(pentoxycarbonylmethyl)phosphonium octylsulfate (3c)
ppm (f1)
255075100125150
![Page 26: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/26.jpg)
26
31P NMR (DMSO-d6, 121 MHz) Tricyclohexyl(pentoxycarbonylmethyl)phosphonium octylsulfate (3c)
ppm (f1)
-50-250255075
35.3
![Page 27: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/27.jpg)
27
1H NMR (DMSO-d6, 300 MHz) Tricyclohexyl(heptoxycarbonylmethyl)phosphonium triflimide (4b)
ppm (f1)
0.501.001.502.002.503.003.504.00
4.18
4.16
4.14
3.85
3.80
2.70
2.66
2.62
2.58
1.91
1.81
1.71
1.68
1.65
1.63
1.61
1.50
1.46
1.41
1.37
1.32
1.30
1.28
1.27
0.89
0.87
0.84
2.00
2.05
3.05
6.00
6.30
5.37
23.50
3.14
![Page 28: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/28.jpg)
28
13C NMR (DMSO-d6, 150 MHz) Tricyclohexyl(heptoxycarbonylmethyl)phosphonium triflimide (4b)
ppm (f1)
255075100125150
![Page 29: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/29.jpg)
29
31P NMR (DMSO-d6, 121 MHz) Tricyclohexyl(heptoxycarbonylmethyl)phosphonium triflimide (4b)
ppm (f1)
-50-250255075
35.2
![Page 30: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/30.jpg)
30
1H NMR (DMSO-d6, 300 MHz) Tricyclohexyl(heptoxycarbonylmethyl)phosphonium octylsulfate (4c)
ppm (f1)
0.000.501.001.502.002.503.003.504.00
4.18
4.16
4.14
3.85
3.81
3.69
3.67
3.65
2.71
2.67
2.63
2.59
1.92
1.80
1.72
1.70
1.67
1.65
1.63
1.60
1.50
1.48
1.46
1.43
1.41
1.37
1.32
1.30
1.28
1.25
0.88
0.87
0.86
0.84
2.00
2.12
1.91
2.90
5.93
6.58
5.30
36.64
6.58
![Page 31: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/31.jpg)
31
13C NMR (DMSO-d6, 150 MHz) Tricyclohexyl(heptoxycarbonylmethyl)phosphonium octylsulfate (4c)
ppm (f1)
255075100125150
![Page 32: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/32.jpg)
32
31P NMR (DMSO-d6, 121 MHz) Tricyclohexyl(heptoxycarbonylmethyl)phosphonium octylsulfate (4c)
ppm (f1)
-50-250255075
35.3
![Page 33: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/33.jpg)
33
1H NMR (DMSO-d6, 300 MHz) Tricyclohexyl(acetoxybutyl))phosphonium triflimide (5b)
ppm (f1)
0.000.501.001.502.002.503.003.504.00
4.10
4.08
4.06
2.58
2.54
2.50
2.46
2.32
2.28
2.27
2.23
2.01
1.90
1.87
1.79
1.74
1.72
1.71
1.68
1.63
1.51
1.47
1.43
1.40
1.35
1.33
1.27
1.24
2.00
3.64
2.09
3.08
20.50
14.18
![Page 34: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/34.jpg)
34
13C NMR (DMSO-d6, 150 MHz) Tricyclohexyl(acetoxybutyl))phosphonium triflimide (5b)
ppm (f1)
255075100125150
![Page 35: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/35.jpg)
35
31P NMR (DMSO-d6, 121 MHz) Tricyclohexyl(acetoxybutyl))phosphonium triflimide (5b)
ppm (f1)
-50-250255075
34.0
![Page 36: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/36.jpg)
36
1H NMR (DMSO-d6, 300 MHz) Tricyclohexyl(acetoxybutyl))phosphonium octylsulfate (5c)
ppm (f1)
0.000.501.001.502.002.503.003.504.00
4.10
4.08
4.05
3.69
3.67
3.65
2.59
2.55
2.51
2.48
2.33
2.29
2.28
2.24
2.01
1.91
1.88
1.79
1.74
1.72
1.70
1.67
1.63
1.50
1.48
1.44
1.40
1.36
1.33
1.25
0.88
0.86
0.84
1.89
3.87
2.17
3.13
20.33
26.17
2.67
2.00
![Page 37: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/37.jpg)
37
13C NMR (DMSO-d6, 150 MHz) Tricyclohexyl(acetoxybutyl))phosphonium octylsulfate (5c)
ppm (f1)
255075100125150
![Page 38: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/38.jpg)
38
31P NMR (DMSO-d6, 121 MHz) Tricyclohexyl(acetoxybutyl))phosphonium octylsulfate (5c)
ppm (f1)
-50-250255075
34.0
![Page 39: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/39.jpg)
39
1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(propoxycarbonylmethyl)phosphonium bromide (7a)
ppm (f1)
0.000.501.001.502.002.503.003.504.00
4.11
4.09
4.07
3.95
3.90
2.41
2.38
2.36
2.35
2.31
1.68
1.66
1.64
1.61
1.59
1.55
1.53
1.52
1.50
1.48
1.45
1.39
1.37
1.35
1.32
1.29
1.28
1.27
0.93
0.90
0.89
0.88
0.86
0.84
2.00
1.94
6.03
8.30
12.16
18.38
![Page 40: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/40.jpg)
40
13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(propoxycarbonylmethyl)phosphonium bromide (7a)
ppm (f1)
255075100125150
![Page 41: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/41.jpg)
41
31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(propoxycarbonylmethyl)phosphonium bromide (7a)
ppm (f1)
-50-250255075
34.1
![Page 42: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/42.jpg)
42
1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(pentoxycarbonylmethyl)phosphonium bromide (8a)
ppm (f1)
0.000.501.001.502.002.503.003.504.00
4.15
4.13
4.10
3.90
3.86
2.38
2.35
2.34
2.33
2.28
1.63
1.60
1.58
1.53
1.50
1.39
1.37
1.29
1.28
1.27
0.89
0.87
0.86
2.00
1.84
5.86
12.22
22.02
8.11
![Page 43: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/43.jpg)
43
13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(pentoxycarbonylmethyl)phosphonium bromide (8a)
ppm (f1)
255075100125150
![Page 44: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/44.jpg)
44
31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(pentoxycarbonylmethyl)phosphonium bromide (8a)
ppm (f1)
-50-250255075
34.2
![Page 45: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/45.jpg)
45
1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(heptoxycarbonylmethyl)phosphonium bromide (9a)
ppm (f1)
0.000.501.001.502.002.503.003.504.004.50
4.15
4.13
4.10
3.95
3.90
2.41
2.38
2.36
2.36
2.34
2.31
1.62
1.60
1.58
1.56
1.53
1.51
1.48
1.45
1.39
1.37
1.35
1.29
1.28
1.27
1.26
0.89
0.87
0.86
0.84
5.96
1.91
2.00
8.66
26.07
12.85
![Page 46: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/46.jpg)
46
13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(heptoxycarbonylmethyl)phosphonium bromide (9a)
ppm (f1)
255075100125150
![Page 47: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/47.jpg)
47
31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(heptoxycarbonylmethyl)phosphonium bromide (9a)
ppm (f1)
-50-250255075
34.1
![Page 48: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/48.jpg)
48
1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(acetoxybutyl))phosphonium iodide (10a)
ppm (t1)
0.000.501.001.502.002.503.003.504.00
4.05
4.03
4.01
2.00
1.75
1.72
1.70
1.68
1.66
1.59
1.57
1.52
1.50
1.48
1.45
1.43
1.40
1.38
1.36
1.34
1.30
1.29
1.28
0.89
0.86
0.84
2.35
2.29
2.27
2.25
2.24
2.20
2.00
3.06
2.10
9.59
7.93
26.18
![Page 49: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/49.jpg)
49
13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(acetoxybutyl))phosphonium iodide (10a)
ppm (f1)
255075100125150
![Page 50: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/50.jpg)
50
31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(acetoxybutyl))phosphonium iodide (10a)
ppm (f1)
-50-250255075
35.0
![Page 51: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/51.jpg)
51
1H NMR (DMSO-d6, 300 MHz) Tri-n-hexylallylphosphonium bromide (11a)
ppm (f1)
0.000.501.001.502.002.503.003.504.004.505.005.50
5.92
5.90
5.89
5.87
5.87
5.86
5.85
5.84
5.83
5.82
5.81
5.80
5.79
5.79
5.78
5.77
5.76
5.75
5.74
5.48
5.47
5.46
5.46
5.42
5.42
5.41
5.40
5.35
5.35
5.34
5.32
5.31
5.31
3.36
3.33
3.31
3.28
2.32
2.29
2.27
2.26
2.25
2.22
1.55
1.52
1.50
1.47
1.39
1.37
1.34
1.32
1.29
1.28
1.27
0.88
0.86
0.84
1.04
1.13
1.00
6.42
6.20
18.24
9.54
![Page 52: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/52.jpg)
52
13C NMR (DMSO-d6, 150 MHz) Tri-n-hexylallylphosphonium bromide (11a)
ppm (f1)
255075100125150
![Page 53: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/53.jpg)
53
31P NMR (DMSO-d6, 121 MHz) Tri-n-hexylallylphosphonium bromide (11a)
ppm (f1)
-50-250255075
33.3
![Page 54: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/54.jpg)
54
1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(methoxymethyl)phosphonium chloride (12a)
ppm (f1)
0.000.501.001.502.002.503.003.504.004.50
4.55
4.53
3.41
2.39
2.36
2.34
2.33
2.28
1.52
1.51
1.50
1.47
1.44
1.37
1.35
1.33
1.28
1.27
1.26
0.87
0.85
0.83
3.10
6.00
2.11
9.21
5.91
18.18
![Page 55: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/55.jpg)
55
13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(methoxymethyl)phosphonium chloride (12a)
ppm (f1)
255075100125150
![Page 56: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/56.jpg)
56
31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(methoxymethyl)phosphonium chloride (12a)
ppm (f1)
-50-2502550
33.0
![Page 57: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/57.jpg)
57
1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(2-hydroxyethyl)phosphonium bromide (13a)
ppm (f1)
0.000.501.001.502.002.503.003.504.00
3.80
3.78
3.76
3.74
3.72
3.70
3.68
3.66
3.64
3.47
3.45
3.43
2.51
2.49
2.47
2.45
2.43
2.31
2.29
2.27
2.26
2.24
2.21
1.57
1.54
1.52
1.49
1.47
1.44
1.39
1.37
1.35
1.32
1.29
1.28
1.27
1.25
0.88
0.86
0.84
6.00
9.49
6.27
18.18
3.14
2.08
![Page 58: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/58.jpg)
58
13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(2-hydroxyethyl)phosphonium bromide (13a)
ppm (f1)
255075100125150
![Page 59: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/59.jpg)
59
31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(2-hydroxyethyl)phosphonium bromide (13a)
ppm (f1)
-50-250255075
34.4
![Page 60: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/60.jpg)
60
1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(propoxycarbonylmethyl)phosphonium triflimide (7b)
ppm (f1)
0.000.501.001.502.002.503.003.504.00
4.13
4.11
4.08
3.81
3.77
2.33
2.31
2.29
2.28
2.26
2.23
1.68
1.65
1.63
1.61
1.56
1.53
1.51
1.48
1.41
1.39
1.37
1.34
1.31
1.30
1.29
1.26
0.94
0.92
0.90
0.89
0.88
0.86
2.00
1.95
5.98
26.62
12.51
![Page 61: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/61.jpg)
61
13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(propoxycarbonylmethyl)phosphonium triflimide (7b)
ppm (f1)
255075100125150
![Page 62: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/62.jpg)
62
31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(propoxycarbonylmethyl)phosphonium triflimide (7b)
ppm (f1)
-50-2502550
34.2
![Page 63: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/63.jpg)
63
1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(propoxycarbonylmethyl)phosphonium octylsulfate (7c)
ppm (f1)
0.501.001.502.002.503.003.504.00
4.12
4.10
4.08
3.84
3.80
3.70
3.68
3.66
2.36
2.33
2.31
2.31
2.26
1.67
1.65
1.62
1.60
1.55
1.53
1.51
1.48
1.40
1.38
1.36
1.30
1.28
1.25
0.94
0.91
0.88
0.86
0.84
2.00
1.92
2.19
5.94
15.62
10.85
28.67
![Page 64: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/64.jpg)
64
13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(propoxycarbonylmethyl)phosphonium octylsulfate (7c)
ppm (f1)
255075100125150
![Page 65: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/65.jpg)
65
31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(propoxycarbonylmethyl)phosphonium octylsulfate (7c)
ppm (t1)
-50-250255075
34.2
![Page 66: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/66.jpg)
66
1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(pentoxycarbonylmethyl)phosphonium triflimide (8b)
ppm (f1)
0.000.501.001.502.002.503.003.504.00
4.16
4.14
4.12
3.81
3.76
2.33
2.31
2.29
2.28
2.23
1.62
1.60
1.56
1.53
1.51
1.48
1.41
1.39
1.37
1.33
1.31
1.30
1.29
0.90
0.88
0.86
2.00
1.88
5.91
30.28
12.54
![Page 67: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/67.jpg)
67
13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(pentoxycarbonylmethyl)phosphonium triflimide (8b)
ppm (f1)
255075100125150
![Page 68: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/68.jpg)
68
31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(pentoxycarbonylmethyl)phosphonium triflimide (8b)
ppm (f1)
-50-250255075
34.2
![Page 69: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/69.jpg)
69
1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(pentoxycarbonylmethyl)phosphonium octylsulfate (8c)
ppm (f1)
0.501.001.502.002.503.003.504.00
4.15
4.13
4.11
3.84
3.79
3.70
3.68
3.66
2.36
2.33
2.31
2.30
2.29
2.26
1.64
1.62
1.59
1.58
1.55
1.53
1.51
1.48
1.46
1.40
1.38
1.36
1.33
1.30
1.29
1.28
1.25
0.90
0.88
0.88
0.86
0.85
2.00
1.92
1.99
5.97
10.59
32.67
15.32
![Page 70: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/70.jpg)
70
13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(pentoxycarbonylmethyl)phosphonium octylsulfate (8c)
ppm (f1)
255075100125150
![Page 71: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/71.jpg)
71
31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(pentoxycarbonylmethyl)phosphonium octylsulfate (8c)
ppm (f1)
-50-250255075
34.2
![Page 72: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/72.jpg)
72
1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(heptoxycarbonylmethyl)phosphonium triflimide (9b)
ppm (f1)
0.000.501.001.502.002.503.003.504.00
4.16
4.14
4.12
3.81
3.76
2.33
2.30
2.28
2.28
2.26
2.23
1.64
1.61
1.59
1.56
1.53
1.51
1.48
1.41
1.39
1.36
1.31
1.30
1.29
1.28
0.90
0.88
0.87
0.86
2.00
1.85
5.95
8.31
26.08
12.20
![Page 73: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/73.jpg)
73
13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(heptoxycarbonylmethyl)phosphonium triflimide (9b)
ppm (f1)
255075100125150
![Page 74: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/74.jpg)
74
31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(heptoxycarbonylmethyl)phosphonium triflimide (9b)
ppm (f1)
-50-250255075
34.2
![Page 75: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/75.jpg)
75
1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(heptoxycarbonylmethyl)phosphonium octylsulfate (9c)
ppm (f1)
0.501.001.502.002.503.003.504.00
4.15
4.13
4.11
3.83
3.78
3.70
3.68
3.66
2.36
2.33
2.31
2.30
2.29
2.26
1.63
1.61
1.59
1.56
1.53
1.51
1.48
1.40
1.38
1.36
1.30
1.29
1.28
1.25
0.90
0.88
0.87
0.86
0.85
0.84
1.87
2.00
2.08
5.84
10.03
36.25
15.33
![Page 76: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/76.jpg)
76
13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(heptoxycarbonylmethyl)phosphonium octylsulfate (9c)
ppm (f1)
255075100125150
![Page 77: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/77.jpg)
77
31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(heptoxycarbonylmethyl)phosphonium octylsulfate (9c)
ppm (f1)
-50-250255075
34.2
![Page 78: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/78.jpg)
78
1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(acetoxybutyl))phosphonium triflimide (10b)
ppm (f1)
0.000.501.001.502.002.503.003.504.00
4.07
4.05
4.02
2.28
2.23
2.23
2.21
2.19
2.18
2.13
2.00
1.76
1.73
1.71
1.69
1.67
1.61
1.59
1.56
1.55
1.53
1.50
1.48
1.45
1.44
1.42
1.40
1.37
1.35
1.31
1.30
1.29
0.90
0.88
0.86
2.00
8.21
3.04
2.15
26.10
9.31
![Page 79: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/79.jpg)
79
13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(acetoxybutyl))phosphonium triflimide (10b)
ppm (f1)
255075100125150
![Page 80: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/80.jpg)
80
31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(acetoxybutyl))phosphonium triflimide (10b)
ppm (f1)
-50-250255075
35.0
![Page 81: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/81.jpg)
81
1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(acetoxybutyl))phosphonium octylsulfate (10c)
ppm (f1)
0.000.501.001.502.002.503.003.504.004.50
4.06
4.04
4.02
3.70
3.68
3.66
2.31
2.26
2.23
2.21
2.20
2.16
2.00
1.75
1.73
1.70
1.68
1.66
1.59
1.56
1.52
1.50
1.48
1.45
1.41
1.39
1.36
1.34
1.31
1.30
1.29
1.25
0.90
0.88
0.86
0.84
1.82
2.00
8.58
3.11
2.30
38.61
12.38
![Page 82: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/82.jpg)
82
13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(acetoxybutyl))phosphonium octylsulfate (10c)
ppm (f1)
255075100125150
![Page 83: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/83.jpg)
83
31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(acetoxybutyl))phosphonium octylsulfate (10c)
ppm (f1)
-50-250255075
35.0
![Page 84: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/84.jpg)
84
1H NMR (DMSO-d6, 300 MHz) Tri-n-hexylallylphosphonium triflimide (11b)
ppm (f1)
0.501.001.502.002.503.003.504.004.505.005.50
5.87
5.85
5.85
5.84
5.83
5.82
5.81
5.80
5.80
5.79
5.78
5.77
5.76
5.76
5.75
5.74
5.73
5.72
5.46
5.45
5.44
5.44
5.40
5.40
5.39
5.37
5.35
5.34
3.22
3.20
3.17
3.14
2.23
2.21
2.19
2.18
2.16
2.13
1.56
1.53
1.50
1.48
1.42
1.39
1.37
1.35
1.32
1.31
1.29
1.27
0.91
0.88
0.86
1.00
2.00
2.01
5.90
5.92
18.15
9.00
![Page 85: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/85.jpg)
85
13C NMR (DMSO-d6, 150 MHz) Tri-n-hexylallylphosphonium triflimide (11b)
ppm (f1)
255075100125150
![Page 86: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/86.jpg)
86
31P NMR (DMSO-d6, 121 MHz) Tri-n-hexylallylphosphonium triflimide (11b)
ppm (f1)
-50-250255075
33.4
![Page 87: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/87.jpg)
87
1H NMR (DMSO-d6, 300 MHz) Tri-n-hexylallylphosphonium octylsulfate (11c)
ppm (f1)
0.501.001.502.002.503.003.504.004.505.005.506.00
5.88
5.86
5.85
5.85
5.84
5.83
5.82
5.81
5.80
5.80
5.79
5.78
5.77
5.76
5.76
5.75
5.74
5.72
5.46
5.46
5.45
5.44
5.41
5.40
5.39
5.39
5.37
5.36
5.35
5.33
5.33
5.32
3.71
3.68
3.66
3.26
3.23
3.20
3.18
2.26
2.23
2.21
2.20
2.19
2.16
1.55
1.52
1.50
1.47
1.45
1.40
1.38
1.36
1.36
1.33
1.31
1.29
1.28
1.27
1.25
0.90
0.88
0.86
0.85
0.84
1.00
2.00
1.84
2.00
5.91
8.19
27.91
11.77
![Page 88: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/88.jpg)
88
13C NMR (DMSO-d6, 150 MHz) Tri-n-hexylallylphosphonium octylsulfate (11c)
ppm (f1)
255075100125150
![Page 89: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/89.jpg)
89
31P NMR (DMSO-d6, 121 MHz) Tri-n-hexylallylphosphonium octylsulfate (11c)
ppm (f1)
-50-250255075
33.3
![Page 90: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/90.jpg)
90
1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(methoxymethyl)phosphonium triflimide (12b)
ppm (f1)
0.501.001.502.002.503.003.504.00
4.38
4.36
3.44
2.28
2.25
2.23
2.22
2.21
2.20
2.17
1.59
1.57
1.54
1.51
1.50
1.49
1.46
1.44
1.41
1.39
1.37
1.35
1.31
1.30
1.29
1.27
0.91
0.88
0.86
2.00
3.02
6.00
6.39
18.65
9.32
![Page 91: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/91.jpg)
91
13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(methoxymethyl)phosphonium triflimide (12b)
ppm (f1)
255075100125150
![Page 92: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/92.jpg)
92
31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(methoxymethyl)phosphonium triflimide (12b)
ppm (f1)
-50-250255075
33.1
![Page 93: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/93.jpg)
93
1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(methoxymethyl)phosphonium octylsulfate (12c)
ppm (f1)
0.000.501.001.502.002.503.003.504.00
4.42
4.40
3.71
3.69
3.67
3.43
2.30
2.28
2.26
2.25
2.23
2.20
1.58
1.56
1.53
1.51
1.49
1.40
1.38
1.36
1.30
1.29
1.28
1.25
0.90
0.88
0.86
0.84
2.00
2.07
3.03
6.15
8.00
28.20
12.31
![Page 94: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/94.jpg)
94
13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(methoxymethyl)phosphonium octylsulfate (12c)
ppm (f1)
255075100125150
![Page 95: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/95.jpg)
95
31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(methoxymethyl)phosphonium octylsulfate (12c)
ppm (f1)
-50-250255075
33.0
![Page 96: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/96.jpg)
96
1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(2-hydroxyethyl)phosphonium triflimide (13b)
ppm (f1)
0.000.501.001.502.002.503.003.504.004.50
3.82
3.80
3.78
3.76
3.74
3.72
2.45
2.43
2.41
2.38
2.36
2.25
2.22
2.20
2.19
2.15
1.53
1.51
1.48
1.45
1.41
1.39
1.31
1.30
1.29
0.90
0.88
0.86
2.00
2.04
6.18
6.12
18.68
9.39
![Page 97: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/97.jpg)
97
13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(2-hydroxyethyl)phosphonium triflimide (13b)
ppm (f1)
255075100125150
![Page 98: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/98.jpg)
98
31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(2-hydroxyethyl)phosphonium triflimide (13b)
ppm (f1)
-50-250255075
34.5
![Page 99: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/99.jpg)
99
1H NMR (DMSO-d6, 300 MHz) Tri-n-hexyl(2-hydroxyethyl)phosphonium octylsulfate (13c)
ppm (f1)
0.000.501.001.502.002.503.003.504.00
3.82
3.80
3.78
3.76
3.73
3.71
3.69
3.66
2.47
2.45
2.43
2.41
2.39
2.27
2.24
2.22
2.21
2.19
2.17
1.57
1.55
1.52
1.50
1.49
1.47
1.45
1.40
1.38
1.36
1.31
1.29
1.28
1.25
0.90
0.87
0.86
0.84
1.92
4.00
6.03
8.28
28.51
12.36
![Page 100: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/100.jpg)
100
13C NMR (DMSO-d6, 150 MHz) Tri-n-hexyl(2-hydroxyethyl)phosphonium octylsulfate (13c)
ppm (f1)
255075100125150
![Page 101: Supporting Informationdigital.csic.es/bitstream/10261/28643/2/Atefi_Farzad_et_al_2.pdf · 1 Supporting Information Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability](https://reader035.fdocuments.us/reader035/viewer/2022081612/5f0f5f607e708231d443d5a6/html5/thumbnails/101.jpg)
101
31P NMR (DMSO-d6, 121 MHz) Tri-n-hexyl(2-hydroxyethyl)phosphonium octylsulfate (13c)
ppm (f1)
-50-250255075
34.4