C9-H · C9 C10 C11 170 150 130 110 90 70 50 30 10 f1 (ppm) 13.55 19.16 26.23 31.94 35.75 48.60...

4
Supplementary Data Anionic Structural Effect on the Dissolution of Arabinoxylan-Rich Hemicellulose in 1-Butyl-3-Methylimidazolium Carboxylate-Based Ionic Liquids Qi Xia a, b , Hong Peng a, b , Lin Yuan a, b , Lifang Hu a, b , Yu Zhang a, b , Roger Ruan a, b , a Engineering Research Center of Biomass Conversion, Ministry of Education, Nanchang University, Nanchang, Jiangxi 330047, P R. China; b State Key Laboratory of Food Science and Technology, Nanchang University, Nanchang, Jiangxi 330031, P R. China. 0 1.5 2.5 3.5 4.5 5.5 6.5 7.5 8.5 9.5 f1 (ppm) 0.83 1.20 1.74 3.88 4.19 7.78 7.86 8.50 9.61 C2-H C11-H C4-H C5-H C6-H C7-H C8-H C9-H C10-H 0.5 1.5 2.5 3.5 4.5 5.5 6.5 7.5 8.5 9.5 10.5 f1 (ppm) 0.82 1.19 1.61 1.73 3.90 4.21 7.95 8.03 10.34 C2-H C4-H C5-H C7-H C6-H C8-H C9-H C10-H C12-H 0.5 1.5 2.5 3.5 4.5 5.5 6.5 7.5 8.5 9.5 f1 (ppm) 0.83 0.88 1.20 1.73 1.87 3.90 4.21 7.86 7.94 10.05 C2-H C4-H C5-H C7-H C6-H C12-H C8-H C13-H C10-H C9-H 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 9.0 10.0 f1 (ppm) 0.77 0.84 1.20 1.42 1.74 1.87 3.90 4.21 7.86 7.94 10.05 C2-H C4-HC5-H C7-H C6-H C8-H C9-H C10-H C14-H C12-H C13-H Fig. S1 1 H NMR spectrum of pure ILs. [Bmim]acetate [Bmim]formate [Bmim]propionate [Bmim]butyrate [Bmim]formate [Bmim]acetate Electronic Supplementary Material (ESI) for RSC Advances. This journal is © The Royal Society of Chemistry 2020

Transcript of C9-H · C9 C10 C11 170 150 130 110 90 70 50 30 10 f1 (ppm) 13.55 19.16 26.23 31.94 35.75 48.60...

Page 1: C9-H · C9 C10 C11 170 150 130 110 90 70 50 30 10 f1 (ppm) 13.55 19.16 26.23 31.94 35.75 48.60 122.79 124.03 138.56 174.05 C2 C5 C4 C7 C6 C8 C9 C10 C11 C12 170 150 130 110 90 70 50

Supplementary DataAnionic Structural Effect on the Dissolution of Arabinoxylan-Rich Hemicellulose in 1-Butyl-3-Methylimidazolium Carboxylate-Based Ionic LiquidsQi Xia a, b, Hong Peng a, b, Lin Yuan a, b, Lifang Hu a, b, Yu Zhang a, b, Roger Ruan a, b, a Engineering Research Center of Biomass Conversion, Ministry of Education, Nanchang University,

Nanchang, Jiangxi 330047, P R. China;b State Key Laboratory of Food Science and Technology, Nanchang University, Nanchang, Jiangxi 330031,

P R. China.

0.51.52.53.54.55.56.57.58.59.5

f1 (ppm)

0.83

1.20

1.74

3.88

4.19

7.78

7.86

8.50

9.61

C2-H

C11-H

C4-

HC

5-H

C6-H

C7-HC8-HC9-H

C10-H

0.51.52.53.54.55.56.57.58.59.510.5f1 (ppm)

0.82

1.19

1.61

1.73

3.90

4.21

7.95

8.03

10.3

4

C2-H C4-H C5-H C7-H

C6-H

C8-H C9-

H

C10-H

C12-H

0.51.52.53.54.55.56.57.58.59.5f1 (ppm)

0.83

0.88

1.20

1.73

1.87

3.90

4.21

7.86

7.94

10.0

5

C2-H C4-H C5-HC7-H

C6-H

C12-H

C8-

H

C13

-HC

10-H

C9-

H

0.01.02.03.04.05.06.07.08.09.010.0f1 (ppm)

0.77

0.84

1.201.

421.

741.

87

3.90

4.21

7.86

7.94

10.0

5

C2-H C4-HC5-H C7-H

C6-HC

8-H

C9-

HC

10-H C14

-H

C12

-H

C13

-H

Fig. S1 1H NMR spectrum of pure ILs.

[Bmim]acetate[Bmim]formate

[Bmim]propionate [Bmim]butyrate

[Bmim]formate [Bmim]acetate

Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2020

Page 2: C9-H · C9 C10 C11 170 150 130 110 90 70 50 30 10 f1 (ppm) 13.55 19.16 26.23 31.94 35.75 48.60 122.79 124.03 138.56 174.05 C2 C5 C4 C7 C6 C8 C9 C10 C11 C12 170 150 130 110 90 70 50

1030507090110130150170

f1 (ppm)

13.5

419

.14

31.8

335

.96

48.8

2

122.

7012

3.99

137.

50

166.

45

C2

C5 C4C6

C7

C8C9

C10

C11

1030507090110130150170f1 (ppm)

13.5

519

.16

26.2

331

.94

35.7

548

.60

122.

7912

4.03

138.

56174.

05 C2

C5 C4C7

C6C8

C9C10

C11

C12

1030507090110130150170

f1 (ppm)

11.5

913

.55

19.1

731

.97

35.8

548

.71

122.

7212

4.01

138.

20

177.

65 C2

C5 C4C6

C7

C8C9

C10C13

C11

1030507090110130150170f1 (ppm)

13.5

514

.69

19.1

820

.06

31.9

935

.85

41.0

848

.72

122.

7212

3.99

138.

18176.

82

C11

C2

C5 C4C7

C12

C6

C8 C13

C9 C14 C10

62667074788286909498102106f1 (ppm)

63.7

573.0

874

.48

75.8

2

102.

22

XC1

XC

4X

C3

XC

2

XC5

Fig. S2 13C NMR spectra of pure ILs and original hemicellulose.

[Bmim]propionate [Bmim]butyrate

Original hemicellulose

Page 3: C9-H · C9 C10 C11 170 150 130 110 90 70 50 30 10 f1 (ppm) 13.55 19.16 26.23 31.94 35.75 48.60 122.79 124.03 138.56 174.05 C2 C5 C4 C7 C6 C8 C9 C10 C11 C12 170 150 130 110 90 70 50

0.51.52.53.54.55.56.57.58.59.5

f1 (ppm)

0.83

1.201.74

3.87

4.18

7.77

7.85

8.49

9.57

3.04.05.0

Hemicellulose

1.02.03.04.05.06.07.08.09.010.0f1 (ppm)

0.83

1.19

1.62

1.73

3.89

4.20

7.88

7.95

10.0

7

Hemicellulose

3.04.05.0

0.51.52.53.54.55.56.57.58.59.510.5

f1 (ppm)

0.83

0.88

1.21

1.73

1.88

3.89

4.20

7.84

7.92

9.96

3.04.05.0

Hemicellulose

0.51.52.53.54.55.56.57.58.59.510.5f1 (ppm)

0.77

0.84

1.41

1.74

1.88

3.89

4.21

7.84

7.92

9.96

3.04.05.0

Hemicellulose

Fig. S3 1H NMR spectra of the mixtures of 10 wt% hemicellulose and ILs.

1030507090110130150170

f1 (ppm)

13.5

419.1

431

.82

35.9

748

.83

63.7

873

.55

74.6

975

.78

102.

25

122.

6912

3.99

137.

46

166.

54 6080100

63.7

873

.55

74.6

975

.78

102.

25

Hemicellulose

1030507090110130150170f1 (ppm)

13.5

819

.17

25.9

531

.93

35.8

448

.69

63.8

574

.05

74.9

075

.81

102.

46

122.

7412

4.02

138.

22

174.

49

6080100

63.8

574

.05

74.9

075

.81

102.

46

Hemicellulose

1030507090110130150170190

f1 (ppm)

11.5

313.5

519

.18

31.9

635

.87

48.7

4

63.8

773

.95

74.8

575

.79

102.

43

122.

7112

4.01

138.

07

177.

87 6080100

63.8

773

.95

74.8

575

.79

102.

43

Hemicellulose

1030507090110130150170f1 (ppm)

13.5

614

.6619.1

920

.02

31.9

835

.87

63.8

473

.95

74.8

875

.76

102.

42

122.

7212

4.00

138.

06

177.

05

658095

63.8

473

.95

74.8

875

.76

102.

42

Hemicellulose

Fig. S4 13C NMR spectra of the mixtures of 10 wt% hemicellulose and ILs.

[Bmim]formate [Bmim]acetate

[Bmim]propionate [Bmim]butyrate]

[Bmim]formate[Bmim]acetate

[Bmim]propionate [Bmim]butyrate]

Page 4: C9-H · C9 C10 C11 170 150 130 110 90 70 50 30 10 f1 (ppm) 13.55 19.16 26.23 31.94 35.75 48.60 122.79 124.03 138.56 174.05 C2 C5 C4 C7 C6 C8 C9 C10 C11 C12 170 150 130 110 90 70 50

0.01.02.03.04.05.06.07.08.09.010.0

f1 (ppm)

0.83

1.20

1.62

1.73

3.89

4.21

7.88

7.96

10.0

8

Hemicellulose

3.04.05.0

0.01.02.03.04.05.06.07.08.09.010.0f1 (ppm)

0.83

1.21

1.63

1.74

3.89

4.20

7.86

7.94

9.99

3.04.05.0

Hemicellulose

0.01.02.03.04.05.06.07.08.09.010.0

f1 (ppm)

0.84

1.22

1.63

1.74

3.89

4.20

7.83

7.91

9.86

3.04.05.0

Hemicellulose

0.01.02.03.04.05.06.07.08.09.010.0f1 (ppm)

0.84

1.22

1.64

1.74

3.89

4.19

7.82

7.89

9.78

3.04.05.0

Hemicellulose

Fig. S5 1H NMR spectra of the mixture of hemicellulose and [Bmim]acetate as a function of the mass ratio of hemicellulose to [Bmim]acetate.

1030507090110130150170

f1 (ppm)

13.5

719

.18

25.9

531

.93

35.8

439

.93

48.6

963

.82

74.0

774

.93

75.8

2

102.

48

122.

7512

4.03

138.

26

174.

52 6080100

63.8

274

.07

74.9

375

.82

102.

48

Hemicellulose

1030507090110130150170f1 (ppm)

13.5

919

.19

25.8

431

.92

35.8

739

.9248

.71

63.8

773

.98

74.9

275

.77

102.

44

122.

7312

4.01

138.

12

174.

70

Hemicellulose

6080100

63.8

773

.98

74.9

275

.77

102.

44

1030507090110130150170

f1 (ppm)

13.6

019

.19

25.7

131

.91

35.9

239

.9248

.76

63.8

773

.88

74.8

375

.72

102.

41

122.

7212

4.02

137.

96

174.

93 6080100

63.8

773

.88

74.8

375

.72

102.

41

Hemicellulose

1030507090110130150170f1 (ppm)

13.6

019

.19

25.6

231

.91

35.9

439

.92

48.7

963

.93

73.8

474

.80

75.6

9

102.

38

122.

7112

4.02

137.

86

175.

09 6080100

63.9

373

.84

74.8

075

.69

102.

38

Hemicellulose

Fig. S6 13C NMR spectra of the mixture of hemicellulose and [Bmim]acetate as a function of the mass ratio of hemicellulose to [Bmim]acetate.

20 wt% 30 wt%

40 wt% 50 wt%

20 wt% 30 wt%

40 wt% 50 wt%