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Supplementary material (ESI) for Green Chemistry

This journal is © The Royal Society of Chemistry 2007

Supplementary Information

+ - 1、The NMR and ESI-MS spectra of [NMP] CH3SO3

2、The GC-MS spectra of (entries 1-19)

+ - The NMR and ESI-MS spectra of [NMP] CH3SO3

5000

4000

3000

2000

1000

0

15.0 10.0 5.0 ppm (t1)

The GC-MS spectra of esters (entries 1-19)

(1) The GC-MS spectrum of propyl

0.69min, of chloroform; 0.97min,

The MS spectra of propyl acetate (0.97min)

(2) The GC-MS spectrum of

1.98min, isopropyl acetate

The MS spectrum of isopropyl acetate (1.98min) (3) The GC-MS spectrum of

2.90min, butyl acetate

4(ZHANG) #665 RT: 3.61 AV: 1 NL: 2.56E7 T: + c Full ms [ 14.00-400.00] 72.85 100

90

80

70 85.85 41.88 60

50

40 Relative Abundance

57.88 30

20 100.93 10

135.97154.12 207.58 253.45 280.90 355.76 0 50 100 150 200 250 300 350 400 m/z The MS spectrum of butyl acetate (2.90min) (4) The GC-MS spectrum of isopentyl acetate

2.20min, isopentyl acetate

3(ZHANG) #405 RT: 2.98 AV: 1 NL: 2.71E7 T: + c Full ms [ 14.00-400.00] 86.89 100

90

80

70

60 41.86

50

40 85.90 Relative Abundance Relative 57.85 30

20 69.89

10 87.91

88.94 121.16 158.00 207.11 226.90 280.98 314.33 356.16 0 50 100 150 200 250 300 350 400 m/z The MS spectrum of isopentyl acetate (2.2min) (5) The GC-MS spectrum of pentyl acetate

3.54min, pentyl acetate

The MS spectrum of pentyl acetate (3.54min)

(6) The GC-MS spectrum of

4.15min, hexyl acetate

1 #920 RT: 3.08 AV: 1 NL: 5.24E7 T: + c Full ms [ 45.00-400.00] 72.88 100

90

80

70

60

50

40 Relative Abundance Relative

30 99.96

20

55.94 10 73.96 115.00 143.10178.92 206.98 249.13281.05 327.11 355.17 398.28 0 50 100 150 200 250 300 350 400 m/z The MS spectrum of hexyl acetate (4.15min)

(7) The GC-MS spectrum of heptyl acetate

4.71min, heptyl acetate

The MS spectrum of heptyl acetate (4.71min)

(8) The GC-MS spectrum of octyl acetate

5.91min, octyl acetate

The MS spectrum of octyl acetate (4.71min) (8) The GC-MS spectrum of ethyl benzoate

5.15 min, ethyl benzoate

The MS spectrum of ethyl benzoate (5.15min) (9) The GC-MS spectrum of

2.25min, ethyl propionate

The MS spectrum of ethyl propionate (2.25min)

(10) The GC-MS spectrum of butyl propionate

2.49min, butyl propionate

The MS spectrum of butyl propionate (2.49min) (11) The GC-MS spectrum of butyl 2-hydroxypropanoate

7.02min, butyl 2-hydroxypropanoate

The MS spectrum of butyl 2-hydroxypropanoate (7.02min)

(12) The GC-MS spectrum of dibutyl oxalate

6.00min, dibutyl oxalate

The MS spectrum of dibutyl oxalate (6.00min)

(13) The GC-MS spectrum of butyl 2-hydroxypropanoate

4.24min, butyl 2-hydroxypropanoate

9 #1655 RT: 4.23 AV: 1 NL: 1.56E7 T: + c Full ms [ 45.00-450.00] 56.9 100

90

80

70

60

50

40 Relative Abundance Relative 84.9 30

20 74.9

10 90.9

102.9 147.0 192.9 210.9 266.9 284.9 325.1 357.2 439.0 0 50 100 150 200 250 300 350 400 450 m/z

The MS spectrum of butyl 2-hydroxypropanoate (4.24min) (14)The GC-MS spectrum of ethyl cinnamate

6.60min, ethyl cinnamate

The MS spectrum of ethyl cinnamate (6.60min)

(15) The GC-MS spectrum of ethyl benzoate

5.15min, ethyl benzoate

The MS spectrum of ethyl benzoate (5.15min)

(16) The GC-MS spectrum of methyl dodecanoate

6.70min, ethyl dodecanoate

The MS spectrum of ethyl dodecanoate (6.70min)

(17) The GC-MS spectrum of ethyl dodecanoate

6.98min, ethyl dodecanoate

The MS spectrum of ethyl dodecanoate (6.98min) (18) The GC-MS spectrum of methyl stearate

8.97min, methyl stearate

The MS spectrum of ethyl dodecanoate (8.97min)

(19) The GC-MS spectrum of (E)-methyl octadec-9-enoate

8.83min, (E)-methyl octadec-9-enoate

The MS spectrum of (E)-methyl octadec-9-enoate (8.83min)