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
1. [1]
  Dan Li , Hui Xin , Xiaofeng Yi . Comprehensive Experimental Design on Ni-based Catalyst for Biofuel Production. University Chemistry, 2024, 39(8): 204-211. doi: 10.3866/PKU.DXHX202312046
2. [2]
  Jinghua Wang , Yanxin Yu , Yanbiao Ren , Yesheng Wang . Integration of Science and Education: Investigation of Tributyl Citrate Synthesis under the Promotion of Hydrate Molten Salts for Research and Innovation Training. University Chemistry, 2024, 39(11): 232-240. doi: 10.3866/PKU.DXHX202402057
3. [3]
  Ling Liu , Haibin Wang , Genrong Qiang . Curriculum Ideological and Political Design for the Comprehensive Preparation Experiment of Ethyl Benzoate Synthesized from Benzyl Alcohol. University Chemistry, 2024, 39(2): 94-98. doi: 10.3866/PKU.DXHX202304080
4. [4]
  Xiaoning TANG , Junnan LIU , Xingfu YANG , Jie LEI , Qiuyang LUO , Shu XIA , An XUE . Effect of sodium alginate-sodium carboxymethylcellulose gel layer on the stability of Zn anodes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1452-1460. doi: 10.11862/CJIC.20240191
5. [5]
  Guang Huang , Lei Li , Dingyi Zhang , Xingze Wang , Yugai Huang , Wenhui Liang , Zhifen Guo , Wenmei Jiao . Cobalt’s Valor, Nickel’s Foe: A Comprehensive Chemical Experiment Utilizing a Cobalt-based Imidazolate Framework for Nickel Ion Removal. University Chemistry, 2024, 39(8): 174-183. doi: 10.3866/PKU.DXHX202311051
6. [6]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
7. [7]
  Fengqiao Bi , Jun Wang , Dongmei Yang . Specialized Experimental Design for Chemistry Majors in the Context of “Dual Carbon”: Taking the Assembly and Performance Evaluation of Zinc-Air Fuel Batteries as an Example. University Chemistry, 2024, 39(4): 198-205. doi: 10.3866/PKU.DXHX202311069
8. [8]
  Shuying Zhu , Shuting Wu , Ou Zheng . Improvement and Expansion of the Experiment for Determining the Rate Constant of the Saponification Reaction of Ethyl Acetate. University Chemistry, 2024, 39(4): 107-113. doi: 10.3866/PKU.DXHX202310117
9. [9]
  Ruitong Zhang , Zhiqiang Zeng , Xiaoguang Zhang . Improvement of Ethyl Acetate Saponification Reaction and Iodine Clock Reaction Experiments. University Chemistry, 2024, 39(8): 197-203. doi: 10.3866/PKU.DXHX202312004
10. [10]
  Shijie Li , Ke Rong , Xiaoqin Wang , Chuqi Shen , Fang Yang , Qinghong Zhang . Design of Carbon Quantum Dots/CdS/Ta₃N₅ S-Scheme Heterojunction Nanofibers for Efficient Photocatalytic Antibiotic Removal. Acta Physico-Chimica Sinica, 2024, 40(12): 2403005-. doi: 10.3866/PKU.WHXB202403005
11. [11]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
12. [12]
  Bingliang Li , Yuying Han , Dianyang Li , Dandan Liu , Wenbin Shang . One-Step Synthesis of Benorilate Guided by Green Chemistry Principles and in vivo Dynamic Evaluation. University Chemistry, 2024, 39(6): 342-349. doi: 10.3866/PKU.DXHX202311070
13. [13]
  Yifeng TAN , Ping CAO , Kai MA , Jingtong LI , Yuheng WANG . Synthesis of pentaerythritol tetra(2-ethylthylhexoate) catalyzed by h-MoO₃/SiO₂. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2155-2162. doi: 10.11862/CJIC.20240147
14. [14]
  Jiaojiao Yu , Bo Sun , Na Li , Cong Wen , Wei Li . Improvement of Classical Organic Experiment Based on the “Reverse-Step Optimization Method”: Taking Synthesis of Ethyl Acetate as an Example. University Chemistry, 2025, 40(3): 333-341. doi: 10.12461/PKU.DXHX202405177
15. [15]
  Qiaoqiao BAI , Anqi ZHOU , Xiaowei LI , Tang LIU , Song LIU . Construction of pressure-temperature dual-functional flexible sensors and applications in biomedicine. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2259-2274. doi: 10.11862/CJIC.20240128
16. [16]
  Ying Zhang , Fang Ge , Zhimin Luo . AI-Driven Biochemical Teaching Research: Predicting the Functional Effects of Gene Mutations. University Chemistry, 2025, 40(3): 277-284. doi: 10.12461/PKU.DXHX202412104
17. [17]
  Wenjun Zheng . Application in Inorganic Synthesis of Ionic Liquids. University Chemistry, 2024, 39(8): 163-168. doi: 10.3866/PKU.DXHX202401020
18. [18]
  Lirui Shen , Kun Liu , Ying Yang , Dongwan Li , Wengui Chang . Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment. University Chemistry, 2024, 39(8): 212-220. doi: 10.3866/PKU.DXHX202312035
19. [19]
  Wei HE , Jing XI , Tianpei HE , Na CHEN , Quan YUAN . Application of solar-driven inorganic semiconductor-microbe hybrids in carbon dioxide fixation and biomanufacturing. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 35-44. doi: 10.11862/CJIC.20240364
20. [20]
  Meiqing Yang , Lu Wang , Haozi Lu , Yaocheng Yang , Song Liu . Recent Advances of Functional Nanomaterials for Screen-Printed Photoelectrochemical Biosensors. Acta Physico-Chimica Sinica, 2025, 41(2): 100018-. doi: 10.3866/PKU.WHXB202310046

Get Citation

PDF

XML

Metrics

PDF Downloads(325)
Abstract views(582)
HTML views(4)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142