Desulfurization and denitrogenation from gasoline and diesel fuels by ...

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Desulfurization and denitrogenation from gasoline and diesel fuels by means of ionic liquids. Antje R. Hansmeier, G.Wytze Meindersma and André B. de Haan.
Electronic Supplementary Material (ESI) for Green Chemistry This journal is © The Royal Society of Chemistry 2011

Desulfurization and denitrogenation from gasoline and diesel fuels by means of ionic liquids Antje R. Hansmeier, G.Wytze Meindersma and André B. de Haan. Eindhoven University of Technology, SPS, P.O. Box 513, 5600 MB Eindhoven, The Netherlands Additional experimental data Table 4. Experimental results sulfur model feed at T = 313.15 K D toluene. [g/g]

D tetralin [g/g]

D thiophene . [g/g]

D DBT [g/g]

S toluene/ n-heptane

S tetralin/ n-heptane

S thiophene/ n-heptane

S DBT/ n-heptane

0.37

0.24

0.92

1.78

30.4

19.7

75.7

146.5

0.34

0.23

0.89

1.69

26.8

18.1

70.1

133.1

[4-mebupy] SCN

0.30

0.20

0.80

1.60

28.2

18.8

75.3

150.6

[bmim] N(CN) 2

0.28

0.18

0.74

1.10

28.7

18.4

75.7

112.6

Ionic Liquid [3-mebupy] N(CN) 2 [4-mebupy] N(CN) 2

[bmim] SCN

0.23

0.18

0.47

0.73

21.8

17.1

44.6

69.3

[bmim] C(CN) 3

0.39

0.28

0.92

1.79

33.1

23.7

70.2

136.6

sulfolane

0.35

0.40

0.77

1.17

20.8

23.8

45.8

69.6

Table 5. Experimental results sulfur model feed at T = 348.15 K D toluene. [g/g]

D tetralin [g/g]

D thiophene . [g/g]

D DBT [g/g]

S toluene/ n-heptane

S tetralin/ n-heptane

S thiophene/ n-heptane

S DBT/ n-heptane

0.33

0.24

0.74

1.21

26.2

19.0

58.7

96.0

0.32

0.23

0.73

1.10

24.6

17.7

56.2

84.6

[4-mebupy] SCN

0.27

0.20

0.72

1.05

20.3

15.0

54.1

78.9

[bmim] N(CN) 2

0.30

0.13

0.69

0.84

25.7

11.1

59.1

72.0

[bmim] [SCN]

0.21

0.10

0.45

0.53

15.7

7.5

33.7

39.7

[bmim] C(CN) 3

0.35

0.26

0.77

1.15

28.7

21.3

63.1

94.3

sulfolane

0.36

0.43

0.80

1.20

17.1

20.4

37.9

56.9

Ionic Liquid [3-mebupy] N(CN) 2 [4-mebupy] N(CN) 2

Table 6. Experimental results nitrogen model feed at T = 313.15 K Ionic Liquid [3-mebupy]N(CN) 2 [4-mebupy]N(CN) 2 [bmim]N(CN) 2 [bmim]C(CN) 3 sulfolane

824

S toluene/ n-heptane 26.7

S tetralin/ n-heptane 16.5

168

757

24.0

16.1

122

157

710

17.2

10.9

136

176

795

27.0

15.0

144

186

839

17.5

25.5

D toluene. [g/g]

D tetralin [g/g]

D pyrrol. [g/g]

D indole [g/g]

D carbazole [g/g]

0.27

0.16

140

180

0.24

0.16

130

0.17

0.11

0.27

0.15

0.35

0.51

1

Electronic Supplementary Material (ESI) for Green Chemistry This journal is © The Royal Society of Chemistry 2011

µV

ex emim alcl4 55i_2.DATA

ethylbenzene

220,000

tetralin

acetone

240,000

200,000 180,000 160,000 140,000 120,000 100,000

benzothiophene

60,000

heptane

SPW 0.10

40,000 20,000

dibenzothiophene

STH 5.00

80,000

0

RT [min] 0

1

2

3

4

5

6

7

8

9

10

11

12

13

14

15

16

17

18

Fig. 4. GC-chromatogram sulfur model feed

28,000 µV

ex emim alcl4 55i_2.DATA tetralin

26,000 24,000 22,000 20,000 18,000 16,000 14,000

benzothiophene

12,000 10,000 8,000 6,000 4,000 2,000 0 -2,000 -4,000 -6,000 -8,000 11

RT [min] 11.1

11.2

11.3

11.4

11.5

11.6

11.7

11.8

11.9

12

12.1

12.2

12.3

12.4

12.5

12.6

12.7

12.8

12.9

13

13.1

Fig. 5. GC-chromatogram sulfur model feed, detail: benzothiophene

2