Room-Temperature Ionic Liquid System Converting Fructose into 5-Hydroxymethylfurfural in High Efficiency

ACS Sustainable Chemistry and Engineering

Volumn 3, Issue 12, 2015, Pages 3338-3345

  Zhang, Jing ^a   Yu, Xinxin ^a   Zou, Feixue ^a   Zhong, Yaohua ^a   Du, Na ^a   Huang, Xirong ^a  

^a SHANDONG UNIVERSITY   (China)

Author keywords

5 Hydroxymethylfurfural; Concerted mechanism; Fructose; Hydrogen bond; Ionic liquids

Indexed keywords

DEHYDRATION; FRUCTOSE; HYDROGEN BONDS; LIQUIDS; ORGANIC SOLVENTS; TEMPERATURE;

5 HYDROXYMETHYL FURFURALS; CONCERTED MECHANISM; HIGH-EFFICIENCY; IONIC LIQUID (ILS); LOW TEMPERATURES; ROOM TEMPERATURE IONIC LIQUIDS; TIME DEPENDENT; WEAK INTERACTIONS;

IONIC LIQUIDS;

EID: 84948977851     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/acssuschemeng.5b01015     Document Type: Article

References (54)

1. Mascal, M.; Nikitin, E. B. Direct, high-yield conversion of cellulose into biofuel Angew. Chem., Int. Ed. 2008, 47, 7924 10.1002/anie.200801594
2. Binder, J. B.; Raines, R. T. Simple chemical transformation of lignocellulosic biomass into furans for fuels and chemicals J. Am. Chem. Soc. 2009, 131, 1979 10.1021/ja808537j
3. Rosatella, A. A.; Simeonov, S. P.; Frade, R. F. M.; Afonso, C. A. M. 5-Hydroxymethylfurfural (HMF) as a building block platform: Biological properties, synthesis and synthetic applications Green Chem. 2011, 13, 754 10.1039/c0gc00401d
4. Gallezot, P. Conversion of biomass to selected chemical products Chem. Soc. Rev. 2012, 41, 1538 10.1039/C1CS15147A
5. van Putten, R.-J.; van der Waal, J. C.; de Jong, E.; Rasrendra, C. B.; Heeres, H. J.; de Vries, J. G. Hydroxymethylfurfural, a versatile platform chemical made from renewable resources Chem. Rev. 2013, 113, 1499 10.1021/cr300182k
6. Wang, T.; Nolte, M. W.; Shanks, B. H. Catalytic dehydration of C6 carbohydrates for the production of hydroxymethylfurfural (HMF) as a versatile platform chemical Green Chem. 2014, 16, 548 10.1039/C3GC41365A
7. Roman-Leshkov, Y.; Chheda, J. N.; Dumesic, J. A. Phase modifiers promote efficient production of hydroxymethylfurfural from fructose Science 2006, 312, 1933 10.1126/science.1126337
8. Xie, H.; Zhao, Z.; Wang, Q. Catalytic conversion of inulin and fructose into 5-hydroxymethylfurfural by lignosulfonic acid in ionic liquids ChemSusChem 2012, 5, 901 10.1002/cssc.201100588
9. Liu, F.; Barrault, J.; De Oliveira Vigier, K.; Jéroîme, F. Dehydration of highly concentrated solutions of fructose to 5-hydroxymethylfurfural in a cheap and sustainable choline chloride/carbon dioxide system ChemSusChem 2012, 5, 1223 10.1002/cssc.201200186
10. Richter, F. H.; Pupovac, K.; Palkovits, R.; Schüth, F. Set of acidic resin catalysts to correlate structure and reactivity in fructose conversion to 5-hydroxymethylfurfural ACS Catal. 2013, 3, 123 10.1021/cs3007439
11. Yi, X.; Delidovich, I.; Sun, Z.; Wang, S.; Wang, X.; Palkovits, R. A heteropoly acid ionic crystal containing Cr as an active catalyst for dehydration of monosaccharides to produce 5-HMF in water Catal. Sci. Technol. 2015, 5, 2496 10.1039/C4CY01555J
12. Pedersen, A. T.; Ringborg, R.; Grotkjær, T.; Pedersen, S.; Woodley, J. M. Synthesis of 5-hydroxymethylfurfural (HMF) by acid catalyzed dehydration of glucose-fructose mixtures Chem. Eng. J. 2015, 273, 455 10.1016/j.cej.2015.03.094
13. Tucker, M. H.; Alamillo, R.; Crisci, A. J.; Gonzalez, G. M.; Scott, S. L.; Dumesic, J. A. Sustainable solvent systems for use in tandem carbohydrate dehydration hydrogenation ACS Sustainable Chem. Eng. 2013, 1, 554 10.1021/sc400044d
14. Zhao, H.; Holladay, J. E.; Brown, H.; Zhang, Z. Metal chlorides in ionic liquid solvents convert sugars to 5-hydroxymethylfurfural Science 2007, 316, 1597 10.1126/science.1141199
15. Yong, G.; Zhang, Y.; Ying, J. Y. Efficient catalytic system for the selective production of 5-hydroxymethylfurfural from glucose and fructose Angew. Chem., Int. Ed. 2008, 47, 9345 10.1002/anie.200803207
16. Hu, S.; Zhang, Z.; Zhou, Y.; Han, B.; Fan, H.; Li, W.; Song, J.; Xie, Y. Conversion of fructose to 5-hydroxymethylfurfural using ionic liquids prepared from renewable materials Green Chem. 2008, 10, 1280 10.1039/b810392e
17. Qi, X.; Watanabe, M.; Aida, T. M.; Smith, R. L., Jr. Efficient process for conversion of fructose to 5-hydroxymethylfurfural with ionic liquids Green Chem. 2009, 11, 1327 10.1039/b905975j
18. Stahlberg, T.; Fu, W.; Woodley, J. M.; Riisager, A. Synthesis of 5-(hydroxymethyl)furfural in ionic liquids: Paving the way to renewable chemicals ChemSusChem 2011, 4, 451 10.1002/cssc.201000374
19. Zakrzewska, M. E.; Bogel-Lukasik, E.; Bogel-Lukasik, R. Ionic liquid-mediated formation of 5-hydroxymethylfurfural-A promising biomass-derived building block Chem. Rev. 2011, 111, 397 10.1021/cr100171a
20. Zhang, S.; Sun, J.; Zhang, X.; Xin, J.; Miao, Q.; Wang, J. Ionic liquid-based green processes for energy production Chem. Soc. Rev. 2014, 43, 7838 10.1039/C3CS60409H
21. 12 furoin and alkane fuel ACS Catal. 2014, 4, 1302 10.1021/cs500058p
22. Eminov, S.; Wilton-Ely, J. D. E. T.; Hallett, J. P. Highly selective and near-quantitative conversion of fructose to 5-hydroxymethylfurfural using mildly acidic ionic liquids ACS Sustainable Chem. Eng. 2014, 2, 978 10.1021/sc400553q
23. Jadhav, A. H.; Kim, H.; Hwang, I. T. Efficient selective dehydration of fructose and sucrose into 5-hydroxymethylfurfural(HMF) using dicationic room temperature ionic liquids as a catalyst Catal. Commun. 2012, 21, 96 10.1016/j.catcom.2012.02.007
24. Moreau, C.; Finiels, A.; Vanoye, L. Dehydration of fructose and sucrose into 5-hydroxymethylfurfural in the presence of 1-H-3-methyl imidazolium chloride acting both as solvent and catalyst J. Mol. Catal. A: Chem. 2006, 253, 165 10.1016/j.molcata.2006.03.046
25. Tong, X.; Li, Y. Efficient and selective dehydration of fructose to 5-hdroxymethylfurfural catalyzed by Brønsted-acidic ionic liquids ChemSusChem 2010, 3, 350 10.1002/cssc.200900224
26. Shi, J.; Liu, W.; Wang, N.; Yang, Y.; Wang, H. Production of 5-hydroxymethylfurfural from mono- and disaccharides in the presence of ionic liquids Catal. Lett. 2014, 144, 252 10.1007/s10562-013-1148-6
27. Ma, Y.; Qing, S.; Wang, L.; Islam, N.; Guan, S.; Gao, Z.; Mamat, X.; Li, H.; Eli, W.; Wang, T. Production of 5-hydroxymethylfurfural from fructose by a thermo-regulated and recyclable Brønsted acidic ionic liquid catalyst RSC Adv. 2015, 5, 47377 10.1039/C5RA08107F
28. Alam, M. I.; De, S.; Dutta, S.; Saha, B. Solid-acid and ionic-liquid catalyzed one-pot transformation of biorenewable substrates into a platform chemical and a promising biofuel RSC Adv. 2012, 2, 6890 10.1039/c2ra20574b
29. Li, Y.; Wang, J.; He, L.; Yang, Z.; Liu, A.; Yu, B.; Luan, C. Experimental and theoretical studies on imidazolium ionic liquid-promoted conversion of fructose to 5-hydroxymethylfurfural Green Chem. 2012, 14, 2752 10.1039/c2gc35845j
30. Abbott, A. P.; Boothby, D.; Davies, G. L.; Rasheed, R. K.; Capper, G. Deep eutectic solvents formed between choline chloride and carboxylic acids: versatile alternatives to ionic liquids J. Am. Chem. Soc. 2004, 126, 9142 10.1021/ja048266j
31. Smith, E. L.; Abbott, A. P.; Ryder, K. S. Deep eutectic solvents (DESs) and their applications Chem. Rev. 2014, 114, 11060 10.1021/cr300162p
32. Ilgen, F.; Ott, D.; Kralisch, D.; Reil, C.; Palmberger, A.; König, B. Conversion of carbohydrates into 5-hyfroxymethylfurfural in highly concentrated low melting mixtures Green Chem. 2009, 11, 1948 10.1039/b917548m
33. Hu, S.; Zhang, Z.; Zhou, Y.; Song, J.; Fan, H.; Han, B. Direct conversion of inulin to 5-hydroxymethylfurfural in biorenewable ionic liquids Green Chem. 2009, 11, 873 10.1039/b822328a
34. Assanosi, A. A.; Farah, M. M.; Wood, J.; Al-Duri, B. A facile acidic choline chloride-p-TSA DES-catalysed dehydration of fructose to 5-hydroxymethylfurfural RSC Adv. 2014, 4, 39359 10.1039/C4RA07065H
35. Chan, J. Y. G.; Zhang, Y. Selective conversion of fructose to 5-hydroxymethylfurfural catalyzed by tungsten salts at low temperatures ChemSusChem 2009, 2, 731 10.1002/cssc.200900117
36. 4 in DMSO and [Bmim]Cl system at room temperature Carbohydr. Polym. 2012, 88, 891 10.1016/j.carbpol.2012.01.032
37. Qi, X.; Watanabe, M.; Aida, T. M.; Smith, R. L. Efficient catalytic conversion of fructose into 5-hydroxymethylfurfural in ionic liquids at room temperature ChemSusChem 2009, 2, 944 10.1002/cssc.200900199
38. Lai, L.; Zhang, Y. The effect of imidazolium ionic liquid on the dehydration of fructose to 5-hydroxymethylfurfural, and a room temperature catalytic system ChemSusChem 2010, 3, 1257 10.1002/cssc.201000201
39. Lai, L.; Zhang, Y. The production of 5-hydroxymethylfurfural from fructose in isopropyl alcohol: A green and efficient system ChemSusChem 2011, 4, 1745 10.1002/cssc.201100489
40. Liu, J.; Tang, Y.; Wu, K.; Bi, C.; Cui, Q. Conversion of fructose into 5-hydroxymethylfurfural (HMF) and its derivatives promoted by inorganic salt in alcohol Carbohydr. Res. 2012, 350, 20 10.1016/j.carres.2011.12.006
41. Wang, H.; Kong, Q.; Wang, Y.; Deng, T.; Chen, C.; Hou, X.; Zhu, Y. Graphene oxide catalyzed dehydration of fructose into 5-hydroxymethylfurfural with isopropanol as cosolvent ChemCatChem 2014, 6, 728 10.1002/cctc.201301067
42. Kraus, G. A.; Guney, T. A direct synthesis of 5-alkoxymethylfurfural ethers from fructose via sulfonic acid-functionalized ionic liquids Green Chem. 2012, 14, 1593 10.1039/c2gc35175g
43. Balakrishnan, M.; Sacia, E. R.; Bell, A. T. Etherification and reductive etherification of 5-(hydroxymethyl)furfural: 5-(alkoxymethyl)furfurals and 2,5-bis(alkoxymethyl)furans as potential bio-diesel candidates Green Chem. 2012, 14, 1626 10.1039/c2gc35102a
44. Wang, H.; Deng, T.; Wang, Y.; Qi, Y.; Hou, X.; Zhu, Y. Efficient catalytic system for the conversion of fructose into 5-ethoxymethylfurfural Bioresour. Technol. 2013, 136, 394 10.1016/j.biortech.2013.02.110
45. Yuan, Z.; Zhang, Z.; Zheng, J.; Lin, J. Efficient synthesis of promising liquid fuels 5-ethoxymethylfurfural from carbohydrates Fuel 2015, 150, 236 10.1016/j.fuel.2015.02.020
46. Bohre, A.; Dutta, S.; Saha, B.; Abu-Omar, M. M. Upgrading furfurals to drop-in biofuels: An overview ACS Sustainable Chem. Eng. 2015, 3, 1263 10.1021/acssuschemeng.5b00271
47. Hu, X.; Westerhof, R. J. M.; Dong, D.; Wu, L. P.; Li, C. Acid-catalyzed conversion of xylose in 20 solvents: Insight into interactions of the solvents with xylose, furfural, and the acid catalyst ACS Sustainable Chem. Eng. 2014, 2, 2562 10.1021/sc5004659
48. Amarasekara, A. S.; Williams, L. D.; Ebede, C. C. Mechanism of the dehydration of D-fructose to 5-hydroxymethylfurfural in dimethyl sulfoxide at 150 degrees C: an NMR study Carbohydr. Res. 2008, 343, 3021 10.1016/j.carres.2008.09.008
49. 13C labeled D-fructose ACS Catal. 2012, 2, 1211 10.1021/cs300045r
50. Antal, M. J.; Mok, W. S. L.; Richards, G. N. Mechanism of formation of 5-(hydroxymethyl)-2-furaldehyde from D-fructose and sucrose Carbohydr. Res. 1990, 199, 91 10.1016/0008-6215(90)84096-D
51. Nikbin, N.; Caratzoulas, S.; Vlachos, D. G. A first principles-based microkinetic model for the conversion of fructose to 5-hydroxymethylfurfural ChemCatChem 2012, 4, 504 10.1002/cctc.201100444
52. Akien, G. R.; Qi, L.; Horváth, I. T. Molecular mapping of the acid catalysed dehydration of fructose Chem. Commun. 2012, 48, 5850 10.1039/c2cc31689g
53. Santos, L. S. Online mechanistic investigations of catalyzed reactions by electrospray ionization mass spectrometry: A tool to intercept transient species in solution Eur. J. Org. Chem. 2008, 2008, 235 10.1002/ejoc.200700723
54. Swatloski, R. P.; Spear, S. K.; Holbrey, J. D.; Rogers, R. D. Dissolution of cellose with ionic liquids J. Am. Chem. Soc. 2002, 124, 4974 10.1021/ja025790m