Citation: MA Hao, LONG Jin-Xing, WANG Fu-Rong, WANG Le-Fu, LI Xue-Hui. Conversion of Cellulose to Butyl Levulinate in Bio-Butanol Medium Catalyzed by Acidic Ionic Liquids[J]. Acta Physico-Chimica Sinica, ;2015, 31(5): 973-979. doi: 10.3866/PKU.WHXB201503171 shu

Conversion of Cellulose to Butyl Levulinate in Bio-Butanol Medium Catalyzed by Acidic Ionic Liquids

1.
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China

Received Date: 20 January 2015
Available Online: 17 March 2015
Fund Project: 国家自然科学基金(21336002, 21276094) (21336002, 21276094)教育部博士点基金(20130172110043)资助项目 (20130172110043)

Butyl levulinate (BL) is one of the most important biochemicals derived from cellulose, and it is of particular interest in industrial applications. Efficient synthesis of BL from cellulose in bio-butanol (bio-BuOH) medium has been investigated in the presence of acidic SO₃H-functionalized ionic liquid (SFIL) catalysts. The results showed that the acid strength of the SFILs, catalyst dosage, reaction temperature, reaction time, and solvent composition significantly affected the conversion of cellulose and the yield of the target products. Using the strongest acidic SFIL 1- (4-sulfobutyl)-3-methylimidazolium hydrosulfate ([C₄H₈SO₃Hmim]HSO₄) as the catalyst, 98.4% of cellulose could be converted into 31.1% of BL accompanied with 33.4%, 20.6%, and 23.8% of butyl formate (BF), water soluble products (WSPs), and biofuel (Biof), respectively, under the optimized conditions. This catalytic system was water-tolerant, and the addition of 0.2 mL water did not significantly decrease its ability for conversion of cellulose. Furthermore, this acidic SFIL catalyst could be recycled up to six consecutive times without loss of catalytic activity.
- SO₃H-functionalized ionic liquid,
- Cellulose,
- Butyl levulinate,
- Butyl formate,
- Biofuel
1. [1]
  
  (1) Gallezot, P. Chem. Soc. Rev. 2012, 41 (4), 1538. doi: 10.1039/ C1CS15147A
2. [2]
  (2) Christensen, E.; Williams, A.; Paul, S.; Burton, S.; McCormick, R. L. Energ. Fuel. 2011, 25 (11), 5422. doi: 10.1021/ef201229j
3. [3]
  (3) Du, X. L.; Bi, Q. Y.; Liu, Y. M.; Cao, Y.; Fan, K. N. ChemSusChem 2011, 4 (12), 183.
4. [4]
  (4) Démolis, A.; Essayem, N.; Rataboul, F. ACS Sustain. Chem. Eng. 2014, 2 (6), 1338. doi: 10.1021/sc500082n
5. [5]
  (5) Bozell, J. J.; Petersen, G. R. Green Chem. 2010, 12 (4), 539.
6. [6]
  (6) Rackemann, D.W.; Doherty, W. O. S. Biofuel. Bioprod. Bior. 2011, 5 (2), 198. doi: 10.1002/bbb.v5.2
7. [7]
  (7) Qureshi, N.; Ezeji, T. C. Biofuel. Bioprod. Bior. 2008, 2 (4), 319. doi: 10.1002/bbb.v2:4
8. [8]
  (8) Durre, P. Biotechnol. J. 2007, 2 (12), 1525.
9. [9]
  (9) Sah, P. P. T.; Ma, S.Y. J. Am. Chem. Soc. 1930, 52 (12), 4880. doi: 10.1021/ja01375a033
10. [10]
  (10) Bart, H. J.; Reidetschlager, J.; Schatka, K.; Lehmann, A. Ind. Eng. Chem. Res. 1994, 33 (1), 21.
11. [11]
  (11) Yadav, G. D.; Borkar, I. V. Ind. Eng. Chem. Res. 2008, 47 (10), 3358. doi: 10.1021/ie800193f
12. [12]
  (12) Dharne, S.; Bokade, V. V. J. Nat. Gas Chem. 2011, 20 (1), 18. doi: 10.1016/S1003-9953 (10)60147-8
13. [13]
  (13) Maheria, K. C.; Kozinski, J.; Dalai, A. Catal. Lett. 2013, 143 (11), 1220. doi: 10.1007/s10562-013-1041-3
14. [14]
  (14) Zhang, Z.; Dong, K.; Zhao, Z. ChemSusChem 2011, 4 (1), 112.
15. [15]
  (15) Wang, G.; Zhang, Z.; Song, L. Green Chem. 2014, 16 (3), 1436. doi: 10.1039/C3GC41693C
16. [16]
  (16) Cara, P. D.; Ciriminna, R.; Shiju, N. R.; Rothenberg, G.; Pagliaro, M. ChemSusChem 2014, 7 (3), 835. doi: 10.1002/cssc.201301027
17. [17]
  (17) Bianchi, D.; Romano, A. M. Process for the Production of Esters of Levulinic Acid from Biomasses. US Patent Appl.13/000498, 2009.
18. [18]
  (18) Hishikawa, Y.; Yamaguchi, M.; Kubo, S.; Yamada, T. J. Wood Sci. 2013, 59 (2), 179.
19. [19]
  (19) Wu, Y.; Fu, Z.; Yin, D.; Xu, Q.; Liu, F.; Lu, C.; Mao, L. Green Chem. 2010, 12 (4), 696. doi: 10.1039/b917807d
20. [20]
  (20) Kobayashi, H.; Ohta, H.; Fukuoka, A. Catal. Sci. Technol. 2012, 2 (5), 869. doi: 10.1039/c2cy00500j
21. [21]
  (21) Wang, J. X.; Wu, Q.; Li, H. S.; Zhen, B. Chem. Ind. Eng. Prog. 2008, 27 (10), 1574. [王敬娴, 吴芹, 黎汉生, 甄彬. 化工进展, 2008, 27 (10), 1574.]
22. [22]
  (22) Taheri, A.; Liu, C.; Lai, B.; Cheng, C.; Pan, X.; Gu, Y. Green Chem. 2014, 16 (8), 3715. doi: 10.1039/C4GC00840E
23. [23]
  (23) He, Z. C.; Wu, Z. M.; Li, Y. F.; Wang, Q.; Pan, L. S.; Liu, Y. J. J. Mol. Catal. 2014, 28 (6), 535. [何志成, 吴志民, 李勇飞, 王庆, 潘浪胜, 刘跃进. 分子催化, 2014, 28 (6), 535.]
24. [24]
  (24) Tao, F.; Song, H.; Chou, L. Bioresour. Technol. 2011, 102, 9000. doi: 10.1016/j.biortech.2011.06.067
25. [25]
  (25) Ren, H.; Zhou, Y.; Liu, L. Bioresour. Technol. 2013, 129, 616. doi: 10.1016/j.biortech.2012.12.132
26. [26]
  (26) Long, J. X.; Guo, B.; Li, X. H.; Wang, F. R.; Wang, L. F. Acta Phys. -Chim. Sin. 2011, 27 (5), 995. [龙金星, 郭斌, 李雪辉, 王芙蓉, 王乐夫. 物理化学学报, 2011, 27 (5), 995.] doi: 10.3866/PKU.WHXB20110506
27. [27]
  (27) Long, J.; Guo, B.; Li, X.; Jiang, Y.; Wang, F.; Tsang, S. C.; Wang, L.; Yu, K. M. K. Green Chem. 2011, 13 (9), 2334. doi: 10.1039/c1gc15597k
28. [28]
  (28) Long, J.; Guo, B.; Teng, J.; Yu, Y.; Wang, L.; Li, X. Bioresour. Technol. 2011, 102, 10114. doi: 10.1016/j.biortech.2011.08.043
29. [29]
  (29) Long, J.; Li, X.; Guo, B.; Wang, F.; Yu, Y.; Wang, L. Green Chem. 2012, 14 (7), 1935. doi: 10.1039/c2gc35105f
30. [30]
  (30) Guo, B.; Long, J. X.; Wang, F. R.; Wang, L. F.; Li, X. H. J. Ind. Eng. Chem. 2012, 63 (8), 2425. [郭斌, 龙金星, 王芙蓉, 王乐夫, 李雪辉. 化工学报, 2012, 63 (8), 2425.]
31. [31]
  (31) Cole, A. C.; Jensen, J. L.; Ntai, I.; Tran, K. L. T.; Weaver, K. J.; Forbes, D. C.; Davis, J. H. J. Am. Chem. Soc. 2002, 124 (21), 5962. doi: 10.1021/ja026290w
32. [32]
  (32) Garves, K. J. Wood Chem. Technol. 1988, 8 (1), 121.
33. [33]
  (33) Peng, L.; Lin, L.; Li, H.; Yang, Q. Appl. Energ. 2011, 88 (12), 4590. doi: 10.1016/j.apenergy.2011.05.049
34. [34]
  (34) Dora, S.; Bhaskar, T.; Singh, R.; Naik, D. V.; Adhikari, D. K. Bioresour. Technol. 2012, 120, 318. doi: 10.1016/j.biortech.2012.06.036
35. [35]
  (35) Hu, X.; Lievens, C.; Larcher, A.; Li, C. Z. Bioresour. Technol. 2011, 102, 10104. doi: 10.1016/j.biortech.2011.08.040
36. [36]
  (36) Lu, Z.; Zheng, H.; Fan, L.; Liao, Y.; Ding, B.; Huang, B. Bioresour. Technol. 2013, 142, 579. doi: 10.1016/j. biortech.2013.05.091
37. [37]
  (37) Hausser, N.; Marinkovic, S.; Estrine, B. Cellulose 2013, 20 (5), 2179. doi: 10.1007/s10570-013-9990-7
38. [38]
  (38) Nel, R. J.; de Klerk, A. Ind. Eng. Chem. Res. 2009, 48 (11), 5230. doi: 10.1021/ie801930r
39. [39]
  (39) Stephenson, R.; Stuart, J. J. Chem. Eng. Data 1986, 31 (1), 56. doi: 10.1021/je00043a019
40. [40]
  (40) Valley, R. B. Text. Res. J. 1955, 25 (11), 930. doi: 10.1177/004051755502501104
41. [41]
  (41) Deng, W.; Liu, M.; Zhang, Q.; Tan, X.; Wang, Y. Chem. Commun. 2010, 46 (15), 2668. doi: 10.1039/b925723c
42. [42]
  (42) Mascal, M.; Nikitin, E. B. ChemSusChem 2010, 3 (12), 1349. doi: 10.1002/cssc.201000326
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