Conversions of Cellobiose and Inulin to Deoxyfructosazine in Aqueous Solutions

Clean - Soil, Air, Water

Volumn 39, Issue 6, 2011, Pages 572-576

  Wu, Suxiang ^a   Fan, Honglei ^a   Zhang, Qian ^b   Cheng, Yan ^a   Wang, Qian ^a   Yang, Guanying ^a   Han, Buxing ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b CHINA NATIONAL PETROLEUM CORPORATION   (China)

Author keywords

Biomass; Cellobiose; Deoxyfructosazine; Inulin; Water

Indexed keywords

AMMONIUM; AQUEOUS SOLUTION; BIOMASS; HYDROLYSIS; PH;

EID: 79959370482     PISSN: 18630650     EISSN: 18630669     Source Type: Journal    
DOI: 10.1002/clen.201000074     Document Type: Article

References (34)

1. E. L. Kunkes, D. A. Simonetti, R. M. West, J. C. Serrano-Ruiz, et al., Catalytic Conversion of Biomass to Monofunctional Hydrocarbons and Targeted Liquid-Fuel Classes, Science 2008, 322, 417.
2. G. W. Huber, S. Iborra, A. Corma, Synthesis of Transportation Fuels from Biomass: Chemistry, Catalysts, and Engineering, Chem. Rev. 2006, 106, 4044.
3. G. W. Huber, J. N. Chheda, C. J. Barrett, J. A. Dumesic, Production of Liquid Alkanes by Aqueous-Phase Processing of Biomass-Derived Carbohydrates, Science 2005, 308, 1446.
4. Y. Román-Leshkov, J. A. Dumesic, Solvent Effects on Fructose Dehydration to 5-Hydroxymethylfurfural in Biphasic Systems Saturated with Inorganic Salts, Top. Catal. 2009, 52, 297.
5. X. H. Qi, M. Watanabe, T. M. Aida, R. L. Smith, Efficient Process for Conversion of Fructose to 5-Hydroxymethylfurfural with Ionic Liquids, Green Chem. 2009, 11, 1327.
6. M. Sasaki, Z. Fang, Y. Fukushima, T. Adschiri, et al., Dissolution and Hydrolysis of Cellulose in Subcritical and Supercritical Water, Ind. Eng. Chem. Res. 2000, 39, 2883.
7. C. Z. Li, Z. H. Zhang, Z. K. Zhao, Direct Conversion of Glucose and Cellulose to 5-Hydroxymethylfurfural in Ionic Liquid under Microwave Irradiation, Tetrahedron Lett. 2009, 50, 5403.
8. Y. Su, H. M. Brown, X. W. Huang, X. D. Zhou, et al., Single-Step Conversion of Cellulose to 5-Hydroxymethylfurfural (HMF), a Versatile Platform Chemical, Appl. Catal., A 2009, 361, 117.
9. Y. Román-Leshkov, J. N. Chheda, J. A. Dumesic, Phase Modifiers Promote Efficient Production of Hydroxymethylfurfural from Fructose, Science 2006, 312, 1933.
10. S. Q. Hu, Z. F. Zhang, Y. X. Zhou, B. X. Han, et al., Conversion of Fructose to 5-Hydroxymethylfurfural Using Ionic Liquids Prepared from Renewable Materials, Green Chem. 2008, 10, 1280.
11. T. Stàhlberg, M. G. Sørensen, A. Riisager, Direct Conversion of Glucose to 5-(Hydroxymethyl)furfural in Ionic Liquids with Lanthanide Catalysts, Green Chem. 2010, 12, 321.
12. J. B. Binder, R. T. Raines, Simple Chemical Transformation of Lignocellulosic Biomass into Furans for Fuels and Chemicals, J. Am. Chem. Soc. 2009, 131, 1979.
13. M. Mascal, E. B. Nikitin, Direct, High-Yield Conversion of Cellulose into Biofuel, Angew. Chem., Int. Ed. 2008, 47, 7924.
14. H. B. Zhao, J. E. Holladay, H. Brown, Z. C. Zhang, Metal Chlorides in Ionic Liquid Solvents Convert Sugars to 5-Hydroxymethylfurfural, Science 2007, 316, 1597.
15. Z. H. Zhang, Z. K. Zhao, Microwave-Assisted Conversion of Lignocellulosic Biomass into Furans in Ionic Liquid, Bioresour. Technol. 2010, 101, 1111.
16. 4 in an Ionic Liquid, Green Chem. 2009, 11, 1746.
17. Y. Román-Leshkov, C. J. Barrett, Z. Y. Liu, J. A. Dumesic, Production of Dimethylfuran for Liquid Fuels from Biomass-derived Carbohydrates, Nature 2007, 447, 982.
18. A. Fukuoka, P. L. Dhepe, Catalytic Conversion of Cellulose into Sugar Alcohols, Angew. Chem., Int. Ed. 2006, 45, 5161.
19. 6-Alcohols Using a Ruthenium Nanocluster Catalyst, J. Am. Chem. Soc. 2006, 128, 8714.
20. C. Luo, S. Wang, H. C. Liu, Cellulose Conversion into Polyols Catalyzed by Reversibly Formed Acids and Supported Ruthenium Clusters in Hot Water, Angew. Chem., Int. Ed. 2007, 46, 7636.
21. N. Ji, T. Zhang, M. Y. Zheng, A. Q. Wang, et al., Direct Catalytic Conversion of Cellulose into Ethylene Glycol Using Nickel-Promoted Tungsten Carbide Catalysts, Angew. Chem., Int. Ed. 2008, 47, 8510.
22. G. Bashiardes, J. C. Carry, M. Evers, US Patent 6, 392, 042B1, 2002.
23. G. Bashiardes, J. C. Carry, M. Evers, US Patent 6, 288, 066B1, 2001.
24. G. Bashiardes, J. C. Carry, M. Evers, US Patent 200402094890, 2004.
25. B. Richard, H. M. Charles, US Patent 2002119939, 2002.
26. Q. Li, Y. H. Ye, A. X. Yan, Y. W. Zhou, et al., Isolation, Identification and Physiological Activities of 2-(1', 2', 3', 4'-Tetrahydroxybutyl)-6-(2″, 3″, 4″-trihydroxybutyl)-pyrazine from Panax Notoginseng, Chem. J. Chin. Univ. 2001, 11, 1824.
27. A. P. Zhu, J. B. Huang, A. Clark, R. Romero, et al., 2, 5-Deoxyfructosazine, a D-Glucosamine Derivative, Inhibits T-Cell Interleukin-2 Production Better than D-Glucosamine, Carbohydr. Res. 2007, 342, 2745.
28. K. Sumoto, M. Irie, N. Mibu, S. Miyano, et al., Formation of Pyrazine Derivatives from D-Glucosamine and Their Deoxyribonucleic-Acid (DNA) Strand Breakage Activity, Chem. Pharm. Bull. 1991, 39, 792.
29. H. Tsuchida, M. Komoto, H. Kato, M. Fujimaki, Formation of Deoxy-Fructosazine and Its 6-Isomer on the Browning Reaction between Glucose and Ammonia in Weak Acidic Medium, Agric. Biol. Chem. 1973, 37, 2571.
30. H. Tsuchida, S. Tachibana, K. Kitamura, M. Komoto, Formation of Deoxyfructosazine and Its 6-Isomer by the Browning Reaction between Fructose and Ammonium Formate, Agric. Biol. Chem. 1976, 40, 921.
31. K. Agyei-Aye, M. X. Chian, J. H. Lauterbach, S. C. Moldoveanu, The Role of the Anion in the Reaction of Reducing Sugars with Ammonium Salts, Carbohydr. Res. 2002, 337, 2273.
32. A. K. Gupta, I. S. Bhatia, Glucofructosan Biosynthesis in Fusarium-Oxysporum-Regulation and Substrate-Specificity of Fructosyl Transferase and Invertase, Phytochemistry 1982, 21, 1249.
33. S. Q. Hu, Z. F. Zhang, Y. X. Zhou, J. L. Song, et al., Direct Conversion of Inulin to 5-Hydroxymethylfurfural in Biorenewable Ionic Liquids, Green Chem. 2009, 11, 873.
34. H. Z. Liu, T. Jiang, B. X. Han, S. G. Liang, Y. X. Zhou, Selective Phenol Hydrogenation to Cyclohexanone over a Dual Supported Pd-Lewis Acid Catalyst, Science 2009, 326, 1250.