Citation: MEN Nan, BAI Xue, WANG Jing-yun, ZHOU Ming-dong. Degradation of cellulose catalyzed by imidazolium perrhenate[J]. Journal of Fuel Chemistry and Technology, ;2017, 45(12): 1449-1455. shu

Degradation of cellulose catalyzed by imidazolium perrhenate

College of Chemistry, Chemical Engineering and Environmental Engineering, Liaoning Shihua University, Fushun 113001, China

Corresponding author: WANG Jing-yun, jingyun.wang@lnpu.edu.cn
Received Date: 14 June 2017
Revised Date: 16 October 2017

Fund Project: Research Project Fund of Liaoning Provincial Department of Education L2017LFW011Talent Scientific Research Fund of LSHU 2016XJJ-063The project was supported by the Natural Science Foundation of Liaoning Province (20170540590), Research Project Fund of Liaoning Provincial Department of Education(L2017LFW011) and Talent Scientific Research Fund of LSHU (2016XJJ-063) for the Financial Supportsthe Natural Science Foundation of Liaoning Province 20170540590

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Imidazolium perrhenate was applied as the catalyst to promote the degradation of microcrystalline cellulose (MCC) with the solvent of ionic liquid 1-allyl-3-methyl imidazolium chloride ([Amim]Cl). The effects of reaction temperature, reaction time, reactant concentration, the amount and structure of catalyst on the degradation of cellulose were studied in details. When using 5% of [mim-(CH₂)₃SO₃H]ReO₄, 70μL of water, 0.1g cellulose and 2.0g [Amim]Cl under microwave irradiation for 30min at 160℃, 89.6% of total reducing sugar (TRS) and 46.7% of glucose yield can be obtained. The degradation mechanism of cellulose catalyzed by imidazolium perrhenate was also studied.The hydrogen bonding between hydroxyl groups of cellulose and ReO₄ anion and aromatic ring cation of catalyst is assumed to be the key step for depolymerization of cellulose.
- imidazolium perrhenate,
- cellulose,
- total reducing sugar,
- glucose
1. [1]
  ZHAO Bo, HU Shang-lian, GONG Dao-yong, LI Hui-ping. New advances on hydrolysis of cellulose to glucose by solid acid[J]. Chem Ind Eng Prog, 2017,36(2):555-567.
2. [2]
  SHEN Shu-guang, LI Huan-mei, WANG Tao, CAI Bei, QIN Hai-feng, WANG Chun-yan. Effect of coal rank on structure of coal-based solid acids and their catalytic performance in cellulose hydrolysis[J]. J Fuel Chem Technol, 2013,41(12):1466-1472.
3. [3]
  KIM S J, DWIATMOKO A A, CHOI J W, SUH Y W, SUH D J, OH M. Cellulose pretreatment with 1-n-butyl-3-methylimidazolium chloride for solidacid-catalyzed hydrolysis[J]. Bioresour Technol, 2010,101(21):8273-8279. doi: 10.1016/j.biortech.2010.06.047
4. [4]
  LAI D M, DENG L, Li J, LIAO B, GUO Q X, FU Y. Hydrolysis of cellulose into glucose by magnetic solid acid[J]. ChemSusChem, 2011,4(1):55-58. doi: 10.1002/cssc.v4.1
5. [5]
  ONDA A, OCHI T, YANAGISAWA K. Selective hydrolysis of cellulose into glucose over solid acid catalysts[J]. Green Chem, 2008,10(10):1033-1037. doi: 10.1039/b808471h
6. [6]
  FENG Jian-ping, LIU Min, JIA Song-yan, GONG Yan-yan, SONG Chun-shan, GUO Xin-wen. Effectively catalytic hydrolysis of cellulose to glucose in the presence of pyrrolidonium-based acidic ionic liquids[J]. Acta Pet Sin(Pet Process Sect), 2012,28(5):775-782.
7. [7]
  AMARASEKARA A S, OWEREH O S. Hydrolysis and decomposition of cellulose in Brønsted acidic ionic liquids under mild conditions[J]. Ind Eng Chem Res, 2009,48(22):10152-10155. doi: 10.1021/ie901047u
8. [8]
  LONG J X, GUO B, TENG J J, LI X H. SO₃H-functionalized ionic liquid:Efficient catalyst for bagasse liquefaction[J]. Bioresour Technol, 2011,102(21):10114-10123. doi: 10.1016/j.biortech.2011.08.043
9. [9]
  JIANG Feng, MA Ding, BAO Xin-he. Acid ionic liquid catalyzed hydrolysis of cellulose[J]. Chin J Catal, 2009,30(4):279-283.
10. [10]
  BEATTIE I R, JONES P J. Methyltrioxorhenium. An air-stable compound containing a carbon-rhenium bond[J]. Inorg Chem, 1979,18(8):2318-2319. doi: 10.1021/ic50198a056
11. [11]
  HERRMANN W A, FISCHER R W, MARZ D W. Methyltrioxorhenium als katalysator für die olefin-oxidation[J]. Angew Chem, 1991,103(12):1706-1709. doi: 10.1002/(ISSN)1521-3757
12. [12]
  JAIN K R, KVHN F E. Immobilization of organorhenium (Ⅶ) oxides[J]. J Organomet Chem, 2007,692(25):5532-5540. doi: 10.1016/j.jorganchem.2007.09.015
13. [13]
  KVHN F E, SCHERBAUM A, HERRMANN W A. Methyltrioxorhenium and its applications in olefin oxidation, metathesis and aldehyde olefination[J]. J Organomet Chem, 2004,689(24):4149-4164. doi: 10.1016/j.jorganchem.2004.08.018
14. [14]
  HOU J L, CHEN Y, MA D M, CORDES B, WANG J Y, WANG X, KVHN F E, GUO H, ZHOU M D. Methyltrioxorhenium-catalyzed highly selective dihydroxylation of 1, 2-allenylic diphenyl phosphine oxides[J]. Chem Commun, 2015,51(35):7439-7442. doi: 10.1039/C5CC01160D
15. [15]
  WANG J Y, ZHOU M D, YUAN Y G, ZHANG Q, FANG X C, ZANG S L. Hydrolysis of cellulose catalyzed by quaternary ammonium perrhenates in 1-allyl-3-methylimidazolium chloride[J]. Bioresour Technol, 2015,197:42-47. doi: 10.1016/j.biortech.2015.07.110
16. [16]
  YUAN Y G, WANG J Y, FU N H, ZANG S L. Hydrolysis of cellulose in 1-allyl-3-methylimidazolium chloride catalyzed by methyltrioxorhenium[J]. Catal Commun, 2016,76:46-49. doi: 10.1016/j.catcom.2015.12.024
17. [17]
  MARKOVITS I I E, EGER W A, YUE S, COKOJA M, MüNCHMEYER C J, ZHANG B., ZHOU M D, GENEST A, MINK J, ZANG S L, RÖSCH N, KVHN F E. Activation of hydrogen peroxide by ionic liquids:Mechanistic studies and application in the epoxidation of olefins[J]. Chem Eur J, 2013,19:5972-5979. doi: 10.1002/chem.201203208
18. [18]
  MILLER G L. Use of dinitrosalicylic acid reagent for determination of reducing sugar[J]. Anal Chem, 1959,31(3):426-428. doi: 10.1021/ac60147a030
19. [19]
  ZHANG Qiang, YU Peng-qiu, LI Lin, LE Zhi-ping. Preparation of 5-HMF from cellulose catalyzed by SnCl₄ under microwave in ZnCl₂ solution[J]. J Fuel Chem Technol, 2017,45(3):317-322.
20. [20]
  MOULTHROP J S, SWATLOSKI R P, MOYNA G, ROGERS R D. High-resolution ¹³C NMR studies of cellulose and cellulose oligomers in ionic liquid solutions[J]. Chem Commun, 2005(12):1557-1559. doi: 10.1039/b417745b
21. [21]
  REMSING R C, SWATLOSKI R P, ROGERS R D, MOYNA G. Mechanism of cellulose dissolution in the ionic liquid 1-n-butyl-3-methylimidazolium chloride:A ¹³C and ^35/37Cl NMR relaxation study on model systems[J]. Chem Commun, 2006(12):1271-1273. doi: 10.1039/b600586c
22. [22]
  ZHANG J M, ZHANG H, WU J, ZHANG J, XIANG J F. NMR spectroscopic studies of cellobiose solvation in EmimAc aimed to understand the dissolution mechanism of cellulose in ionic liquids[J]. Phys Chem Chem Phys, 2010,12(8):1941-1947. doi: 10.1039/b920446f
23. [23]
  JIA L Y, PEDERSEN C M, QIAO Y, DENG T S, ZUO P P, GE W Z, QIN Z F, HOU X L, WANG Y X. Glucosamine condensation catalyzed by 1-ethyl-3-methylimidazolium acetate:Mechanistic insight from NMR spectroscopy[J]. Phys Chem Chem Phys, 2015,17:23173-23182. doi: 10.1039/C5CP02169C
24. [24]
  WANG Ying-xiong, HOU Xiang-lin, ZHU Yu-lei. The catalytic conversion of sugar derivatives to oxygen containing liquid fuel and fine chemicals[J]. Biotechnol Business, 2017,3(5):48-55.
25. [25]
  HU R, LIN L, LIU T J, LIU S J. Dilute sulfuric acid hydrolysis of sugar maple wood extract at atmospheric pressure[J]. Bioresour Technol, 2010,101(10):3586-3594. doi: 10.1016/j.biortech.2010.01.005
26. [26]
  ZHANG B, LI S, YUE S, COKOJA M, ZHOU M D, ZANG S L, KVHN F E. Imidazolium perrhenate ionic liquids as efficient catalysts for the selective oxidation of sulfides to sulfones[J]. J Organomet Chem, 2013,744:108-112. doi: 10.1016/j.jorganchem.2013.05.043
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