Paper
Green Chemistry
Table 3 Kinetic parameters of the glucose conversion using [IMEP]Cl
10 M. Bicker, S. Endres, L. Ott and H. Vogel, J. Mol. Catal. A:
Chem., 2005, 239, 151.
Parameter
Value
11 H. Kishida, F. M. Jin, X. Y. Yan, T. Moriya and H. Enomoto,
Carbohydr. Res., 2006, 341, 2619.
12 X. Yan, F. Jin, K. Tohji, T. Moriya and H. Enomoto, J. Mater.
Sci., 2007, 42, 9995.
Reaction order, n
Activation energy, E
Pre-exponential factor, A (min
Correlation coefficient
1
(kJ mol−
1
)
62.66
1.7 × 10
0.9751
a
−
1
8
)
1
3 X. Y. Yan, F. M. Jin, K. Tohji, A. Kishita and H. Enomoto,
AIChE J., 2010, 56, 2727.
moderate temperatures, minimizing the energy consumption 14 C. B. Rasrendra, I. G. B. N. Makertihartha, S. Adisasmito
and undesirable sugar degradation pathways.
and H. J. Heeres, Top. Catal., 2010, 53, 1241.
5 D. Esposito and M. Antonietti, ChemSusChem, 2013, 6, 989.
6 Y. Wang, F. Jin, M. Sasaki, Wahyudiono, F. Wang, Z. Jing
and M. Goto, AIChE J., 2013, 59, 2096.
1
1
4
. Conclusions
17 A. Onda, T. Ochi, K. Kajiyoshi and K. Yanagisawa, Catal.
An efficient synthesis of LA from glucose has been achieved
Commun., 2008, 9, 1050.
using [IMEP]Cl as catalysts in an alkaline solution. Several 18 A. Onda, T. Ochi, K. Kajiyoshi and K. Yanagisawa, Appl.
factors including the alkalinity, [IMEP]Cl loading, temperature
Catal., A, 2008, 343, 49.
and atmosphere influenced the yield. The optimal LA yield 19 G. Epane, J. C. Laguerre, A. Wadouachi and D. Marek,
was 63%. Meanwhile, good activity was exhibited during the
Green Chem., 2010, 12, 502.
conversion of other monosaccharides. A possible reaction 20 M. S. Holm, S. Saravanamurugan and E. Taarning, Science,
mechanism for the conversion of glucose was proposed. The
2010, 328, 602.
−
1
activation energy of the glucose conversion was 62.66 kJ mol
21 F. de Clippel, M. Dusselier, R. Van Rompaey, P. Vanelderen,
J. Dijkmans, E. Makshina, L. Giebeler, S. Oswald,
G. V. Baron, J. F. M. Denayer, P. P. Pescarmona, P. A. Jacobs
and B. F. Sels, J. Am. Chem. Soc., 2012, 134, 10089.
8
−1
with a pre-exponential factor of 1.7 × 10 min . The excellent
performance of [IMEP]Cl suggests that it might be used as
catalysts for carbohydrate conversion.
2
2 Y. L. Wang, W. P. Deng, B. J. Wang, Q. H. Zhang, X. Y. Wan,
Z. C. Tang, Y. Wang, C. Zhu, Z. X. Cao, G. C. Wang and
H. L. Wan, Nat. Commun., 2013, 4, 2141.
Acknowledgements
2
3 N. T. M. Hai, J. Oderrnatt, V. Grimaudo, K. W. Kraemer,
A. Fluegel, M. Arnold, D. Mayer and P. Broekmann, J. Phys.
Chem. C, 2012, 116, 6913.
This project was sponsored by the National Natural Science
Foundation of China under grant number 20806007 and the
National Basic Research Program of China (973 Program) 24 J. Howarth, K. Hanlon, D. Fayne and P. McCormac, Tetra-
(2010CB226902).
hedron Lett., 1997, 38, 3097.
2
2
2
5 W. E. Eckles and T. W. Starinshak, US Pat., 4 038 161, 1977.
6 W. A. Rogers and J. E. Woehst, US Pat., 3 320 317, 1967.
7 T. W. Smith, M. Zhao, F. Yang, D. Smith and P. Cebe,
Macromolecules, 2013, 46, 1133.
Notes and references
1
A. Corma, S. Iborra and A. Velty, Chem. Rev., 2007, 107, 28 L. C. Branco, J. N. Rosa, J. J. Moura Ramos and
411. C. A. Afonso, Chem. – Eur. J., 2002, 8, 3671.
S. G. Karp, A. H. Igashiyama, P. F. Siqueira, J. C. Carvalho, 29 Z. Shen, F. M. Jin, Y. L. Zhang, B. Wu, A. Kishita, K. Tohji
L. P. S. Vandenberghe, V. Thomaz-Soccol, J. Coral, and H. Kishida, Ind. Eng. Chem. Res., 2009, 48, 8920.
J. L. Tholozan, A. Pandey and C. R. Soccol, Bioresour. 30 A. Kanazawa, T. Ikeda and T. Endo, J. Polym. Sci., Part A:
Technol., 2011, 102, 1765. Polym. Chem., 1993, 31, 1099.
Z. Zhang, B. Du, L. J. Zhang, Y. X. Da, Z. J. Quan, L. J. Yang 31 F. M. Jin, J. Yun, G. M. Li, A. Kishita, K. Tohji and
and X. C. Wang, RSC Adv., 2013, 3, 9201. H. Enomoto, Green Chem., 2008, 10, 612.
Y. Yang, C. Hu and M. M. Abu-Omar, J. Mol. Catal. A: 32 C. B. Rasrendra, B. A. Fachri, I. G. B. N. Makertihartha,
2
2
3
4
Chem., 2013, 376, 98.
S. Adisasmito and H. J. Heeres, ChemSusChem, 2011, 4,
5
6
Y. Hayashi and Y. Sasaki, Chem. Commun., 2005, 2716.
768.
M. Dusselier, P. Van Wouwe, A. Dewaele, E. Makshina and 33 L. J. Chen, A. W. Zeng, H. B. Dong, Q. Li and C. C. Niu,
B. F. Sels, Energy Environ. Sci., 2013, 6, 1415. Bioresour. Technol., 2012, 112, 280.
R. P. John, K. M. Nampoothiri and A. Pandey, Appl. Micro- 34 C. Bamford, D. Bamford and J. Collins, Proc. R. Soc.
biol. Biotechnol., 2007, 74, 524.
P. T. Anastas and M. M. Kirchhoff, Acc. Chem. Res., 2002,
7
8
9
London, Ser. A, 1950, 204, 85; C. Bamford and J. Collins,
Proc. R. Soc. London, Ser. A, 1955, 228, 100; R. Montgomery,
Ind. Eng. Chem. Res., 1953, 45, 1144.
3
5, 686.
J. Song, H. Fan, J. Ma and B. Han, Green Chem., 2013, 15, 35 Y. S. Qu, Y. L. Song, C. P. Huang, J. Zhang and B. H. Chen,
619. Ind. Eng. Chem. Res., 2012, 51, 13008.
2
4240 | Green Chem., 2014, 16, 4234–4240
This journal is © The Royal Society of Chemistry 2014