Citation: LI Xiang-Cheng, ZHANG Yu, XIA Yin-Jiang, HU Bi-Cheng, WANG Yan-Qin, LU Guan-Zhong. One-Pot Catalytic Conversion of Xylose to Furfural on Mesoporous Niobium Phosphate[J]. Acta Physico-Chimica Sinica, ;2012, 28(10): 2349-2354. doi: 10.3866/PKU.WHXB201207312 shu

One-Pot Catalytic Conversion of Xylose to Furfural on Mesoporous Niobium Phosphate

1.
Research Institute of Industrial Catalysis, East China University of Science and Technology, Shanghai 200237, P. R. China

Received Date: 11 June 2012
Available Online: 31 July 2012
Fund Project: 国家自然科学基金(20973058) (20973058)

The conversion of xylose to furfural normally involves two steps: the isomerization of xylose to xylulose catalyzed by an enzyme, a base or a Lewis acid, followed by the acid-catalyzed dehydration of xylulose to furfural. To allow a more efficient single-step conversion, a new water-tolerant solid acid catalyst, mesoporous niobium phosphate was synthesized. This synthesis was performed using a soft template approach, with cetyltriethylammonium bromide (CTAB) as the template. The structure and properties of the catalyst thus synthesized were investigated by X-ray diffraction (XRD), N₂ sorption, transmission electron microscopy (TEM), temperature-programmed desorption of NH₃ (NH₃-TPD), and pyridine sorption FTIR (Py-FTIR). These studies determined that the niobium phosphate not only had a large surface area (>200 m²·g^-1) and narrow pore size distribution (3.5 nm), but also had relatively strong Lewis and Brønsted acidity. This catalyst was found to be capable of producing furfural via a simple one-pot process, including the isomerization of xylose to xylulose and subsequent dehydration. The influence of several variables including temperature, mass ratio of xylose/catalyst, and reaction time on the extent of xylose conversion and furfural yield were studied. Under optimal conditions, the yield of furfural in aqueous solution reached 49.8% with 96.5% xylose conversion. It was further determined that both the yield and the separation of furfural could be improved by employing a methyl isobutyl ketone (MIBK)/water (volume ratio 7:3) biphase containing NaCl in the aqueous phase, resulting in a 68.4% yield.
- Mesoporous niobium phosphate,
- Brö,
- nsted acid,
- Lewis acid,
- Xylose,
- Furfural,
- Aqueous phase
1. [1]
  
  (1) Xu,W. J.;Wang, H. F.; Liu, X. H.; Ren, J.W.;Wang, Y. Q.; Lu,G. Z. Chem. Commun. 2011, 47, 3924. doi: 10.1039/c0cc05775d
2. [2]
  (2) Huber, G.W.; Chheda, J. N.; Barrett, C. J.; Dumesic, J. A.Science 2005, 308, 1446. doi: 10.1126/science.1111166
3. [3]
  (3) Alonso, D. M.; Bond, J. Q.; Dumesic, J. A. Green Chem. 2010,12, 1493. doi: 10.1039/c004654j
4. [4]
  (4) Choudhary, V.; Pinar, A. B.; Sandler, S. I.; Vlachos, D. G.;Lobo, R. F. ACS Catal. 2011, 1, 1724. doi: 10.1021/cs200461t
5. [5]
  (5) Dias, A. S.; Lima, S.; Carriazo, D.; Rives, V.; Pillinger, M.;Valente, A. A. J. Catal. 2006, 224, 230.
6. [6]
  (6) Yang, Y.; Hu, C.W.; Abu-Omar, M. M. ChemSusChem 2012, 5,405. doi: 10.1002/cssc.201100688
7. [7]
  (7) Nikolla, E.; Leshkov, Y. R.; Moliner, M.; Davis, M. E. ACS Catal. 2011, 1, 408. doi: 10.1021/cs2000544
8. [8]
  (8) Wang, H. Y.; Zhang, C. B.; He, H.;Wang, L. Acta Phys. -Chim. Sin. 2010, 26, 1873. [王华瑜, 张长斌, 贺泓, 王莲. 物理化学学报, 2010, 26, 1873.] doi: 10.3866/PKU.WHXB20100721
9. [9]
  (9) ng, Y. Y.; Liu, M.; Jia, S. Y.; Feng, J. P.; Song, C. S.; Guo, X.W. Acta Phys. -Chim. Sin. 2012, 28, 686. [公艳艳, 刘民, 贾松岩, 冯建萍, 宋春山, 郭新闻. 物理化学学报, 2012, 28, 686.]doi: 10.3866/PKU.WHXB201112292
10. [10]
  (10) Wang, J. J.; Xu,W. J.; Ren, J.W.; Liu, X. H.; Lu, G. Z.;Wang,Y. Q. Green Chem. 2011, 13, 2678. doi: 10.1039/c1gc15306d
11. [11]
  (11) Zhang, B. H.; Ren, J.W.; Liu, X. H.; Guo, Y.; Guo, Y. L.; Lu, G.Z.;Wang, Y. Q. Catal. Commun. 2010, 11, 629. doi: 10.1016/j.catcom.2010.01.010
12. [12]
  (12) Moreau, C.; Durand, R.; Razigade, S.; Duhamet, J.; Faugeras,P.; Rivalier, P.; Ros, P.; Avignonu, G. Appl. Catal. A 1996, 145,211. doi: 10.1016/0926-860X(96)00136-6
13. [13]
  (13) Lourvanij, K.; Rorrer, G. L. Ind. Eng. Chem. Res. 1993, 32, 11.doi: 10.1021/ie00013a002
14. [14]
  (14) Lourvanij, K.; Rorrer, G. L. Appl. Catal. A 1994, 109, 147. doi: 10.1016/0926-860X(94)85008-9
15. [15]
  (15) Shimizu, K. I.; Uozumi, R.; Satsuma, A. Catal. Commun. 2009,10, 1849. doi: 10.1016/j.catcom.2009.06.012
16. [16]
  (16) Qi, X. H.;Watanabe, M.; Aida, T. M.; Smith, R. L. J. Ind. Eng. Chem. Res. 2008, 47, 9234. doi: 10.1021/ie801016s
17. [17]
  (17) Watanabe, M.; Aizawa, Y.; Iida, T.; Nishimura, R.; Inomata, H.Appl. Catal. A 2005, 295, 150. doi: 10.1016/j. apcata.2005.08.007
18. [18]
  (18) Yan, H.; Yang, Y.; Tong, D.; Xiang, X.; Hu, C. Catal. Commun.2009, 10, 1558. doi: 10.1016/j.catcom.2009.04.020
19. [19]
  (19) Benvenuti, F.; Carlini, C.; Patrono, P.; Galletti, A. M. R.;Sbrana, G.; Massucci, M. A.; Galli, P. Appl. Catal. A 2000, 193,147. doi: 10.1016/S0926-860X(99)00424-X
20. [20]
  (20) Nowak, I.; Ziolek, M. Chem. Rev. 1999, 99, 3603. doi: 10.1021/cr9800208
21. [21]
  (21) Kozo, T. Catal. Today 2003, 78, 65. doi: 10.1016/S0920-5861(02)00343-7
22. [22]
  (22) Ziolek, M. Catal. Today 2003, 78, 47.
23. [23]
  (23) Nakajima, K.; Baba, Y.; Noma, R.; Kitano, M.; Kondo, J. N.;Hayashi, S.; Hara, M. J. Am. Chem. Soc. 2011, 133, 4224. doi: 10.1021/ja110482r
24. [24]
  (24) Armaroli, T.; Busca, G. J. Mol. Catal. A: Chem. 2000, 151, 233.doi: 10.1016/S1381-1169(99)00248-4
25. [25]
  (25) Sarkar, A.; Pramanik, P. Microporous Mesoporous Mat. 2009,117, 580. doi: 10.1016/j.micromeso.2008.08.001
26. [26]
  (26) Paolo, C.; Antonella, G.; Serena, B.; Aline, A. Catal. Today2006, 118, 373. doi: 10.1016/j.cattod.2006.07.024
1. [1]
  Haiping Wang . A Streamlined Method for Drawing Lewis Structures Using the Valence State of Outer Atoms. University Chemistry, 2024, 39(8): 383-388. doi: 10.12461/PKU.DXHX202401073
2. [2]
  Wenqi Gao , Xiaoyan Fan , Feixiang Wang , Zhuojun Fu , Jing Zhang , Enlai Hu , Peijun Gong . Exploring Nernst Equation Factors and Applications of Solid Zinc-Air Battery. University Chemistry, 2024, 39(5): 98-107. doi: 10.3866/PKU.DXHX202310026
3. [3]
  Bing LIU , Huang ZHANG , Hongliang HAN , Changwen HU , Yinglei ZHANG . Visible light degradation of methylene blue from water by triangle Au@TiO₂ mesoporous catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 941-952. doi: 10.11862/CJIC.20230398
4. [4]
  Yuanpei ZHANG , Jiahong WANG , Jinming HUANG , Zhi HU . Preparation of magnetic mesoporous carbon loaded nano zero-valent iron for removal of Cr(Ⅲ) organic complexes from high-salt wastewater. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1731-1742. doi: 10.11862/CJIC.20240077
5. [5]
  Qingying Gao , Tao Luo , Jianyuan Su , Chaofan Yu , Jiazhu Li , Bingfei Yan , Wenzuo Li , Zhen Zhang , Yi Liu . Refinement and Expansion of the Classic Cinnamic Acid Synthesis Experiment. University Chemistry, 2024, 39(5): 243-250. doi: 10.3866/PKU.DXHX202311074
6. [6]
  Yiling Wu , Peiyao Jin , Shenyue Tian , Ji Zhang . The Star of Sugar Substitutes: An Interview of Erythritol. University Chemistry, 2024, 39(9): 22-27. doi: 10.12461/PKU.DXHX202404034
7. [7]
  Yuena Yang , Xufang Hu , Yushan Liu , Yaya Kuang , Jian Ling , Qiue Cao , Chuanhua Zhou . The Realm of Smart Hydrogels. University Chemistry, 2024, 39(5): 172-183. doi: 10.3866/PKU.DXHX202310125
8. [8]
  Gaoyan Chen , Chaoyue Wang , Juanjuan Gao , Junke Wang , Yingxiao Zong , Kin Shing Chan . Heart to Heart: Exploring Cardiac CT. University Chemistry, 2024, 39(9): 146-150. doi: 10.12461/PKU.DXHX202402011
9. [9]
  Meijin Li , Xirong Fu , Xue Zheng , Yuhan Liu , Bao Li . The Marvel of NAD⁺: Nicotinamide Adenine Dinucleotide. University Chemistry, 2024, 39(9): 35-39. doi: 10.12461/PKU.DXHX202401027
10. [10]
  Keying Qu , Jie Li , Ziqiu Lai , Kai Chen . Unveiling the Mystery of Chirality from Tartaric Acid. University Chemistry, 2024, 39(9): 369-378. doi: 10.12461/PKU.DXHX202310091
11. [11]
  Yuhang Jiang , Weijie Liu , Jiaqi Cai , Jiayue Chen , Yanping Ren , Pingping Wu , Liulin Yang . A Journey into the Science and Art of Sugar: “Dispersion of Light and Optical Rotation of Matter” Science Popularization Experiment. University Chemistry, 2024, 39(9): 288-294. doi: 10.12461/PKU.DXHX202401054
12. [12]
  Zijian Zhao , Yanxin Shi , Shicheng Li , Wenhong Ruan , Fang Zhu , Jijun Jiang . A New Exploration of the Preparation of Polyacrylic Acid by Free Radical Polymerization Based on the Concept of Green Chemistry. University Chemistry, 2024, 39(5): 315-324. doi: 10.3866/PKU.DXHX202311094
13. [13]
  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
14. [14]
  Xiaowu Zhang , Pai Liu , Qishen Huang , Shufeng Pang , Zhiming Gao , Yunhong Zhang . Acid-Base Dissociation Equilibrium in Multiphase System: Effect of Gas. University Chemistry, 2024, 39(4): 387-394. doi: 10.3866/PKU.DXHX202310021
15. [15]
  Junke LIU , Kungui ZHENG , Wenjing SUN , Gaoyang BAI , Guodong BAI , Zuwei YIN , Yao ZHOU , Juntao LI . Preparation of modified high-nickel layered cathode with LiAlO₂/cyclopolyacrylonitrile dual-functional coating. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1461-1473. doi: 10.11862/CJIC.20240189
16. [16]
  Jizhou Liu , Chenbin Ai , Chenrui Hu , Bei Cheng , Jianjun Zhang . 六氯锡酸铵促进钙钛矿太阳能电池界面电子转移及其飞秒瞬态吸收光谱研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2402006-. doi: 10.3866/PKU.WHXB202402006
17. [17]
  Ke Li , Chuang Liu , Jingping Li , Guohong Wang , Kai Wang . 钛酸铋/氮化碳无机有机复合S型异质结纯水光催化产过氧化氢. Acta Physico-Chimica Sinica, 2024, 40(11): 2403009-. doi: 10.3866/PKU.WHXB202403009
18. [18]
  Yukun Chang , Haoqin Huang , Baolei Wang . Preparation of Trans-Cinnamic Acid via “One-Pot” Protocol of Aldol Condensation-Hydrolysis Reaction: Recommending an Improved Organic Synthesis Experiment. University Chemistry, 2024, 39(4): 322-328. doi: 10.3866/PKU.DXHX202309095
19. [19]
  Yang Chen , Peng Chen , Yuyang Song , Yuxue Jin , Song Wu . Application of Chemical Transformation Driven Impurity Separation in Experiments Teaching: A Novel Method for Purification of α-Fluorinated Mandelic Acid. University Chemistry, 2024, 39(6): 253-263. doi: 10.3866/PKU.DXHX202310077
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(900)
Abstract views(2399)
HTML views(31)

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