Direct, high-yield conversion of cellulose into biofuel

Angewandte Chemie - International Edition

Volumn 47, Issue 41, 2008, Pages 7924-7926

  Mascal, Mark ^a   Nikitin, Edward B ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Biofuels; Carbohydrates; Cellulose; Furans; Sustainable chemistry

Indexed keywords

CELLULOSE; CELLULOSE DERIVATIVES; CHEMICAL REACTIONS; CHLORINE; DEWATERING; DOPING (ADDITIVES); ETHERS; ORGANIC COMPOUNDS; SUBSTITUTION REACTIONS;

CARBOHYDRATES; CHEMICAL EQUATIONS; FURANS; ORGANIC PHASE; SUSTAINABLE CHEMISTRY;

BIOFUELS;

CELLULOSE; FURAN DERIVATIVE; GASOLINE;

ARTICLE; CHEMISTRY; HYDROLYSIS; SYNTHESIS;

CELLULOSE; FURANS; GASOLINE; HYDROLYSIS;

CARBOHYDRATES; CELLULOSE; CELLULOSE DERIVATIVES; CHEMICAL REACTIONS; CHLORINE; DRAINAGE; ETHERS; FUELS; FURANS; ORGANIC COMPOUNDS;

EID: 54749101112     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200801594     Document Type: Article

References (29)

1. N. S. Lewis, D. G. Nocera, Proc. Natl. Acad. Sci. USA 2006 103, 15729.
2. A. J. Ragauskas, C. K. Williams, B. H. Davison, G. Britovsek, J. Cairney, C. A. Eckert, W. J. Frederick, Jr., J. P. Hallett, D. J. Leak, C. L. Liotta, J. R. Mielenz, R. Murphy, R. Templer, T. Tschaplinski, Science 2006, 311, 484.
3. For a thought-provoking article which examines both sides of this issue, see Chem. Eng. News, 2007, 8, 12.
4. See also: a) J. Hill, E. Nelson, D. Tilman, S. Polasky, D. Tiffany, Proc. Natl. Acad. Sci. USA 2006, 103, 11206;
5. b) R. Hammerschlag, Environ. Sci. Technol. 2006, 40, 1744;
6. c) A. E. Farrell, R. J. Plevin, B. T. Turner, A. D. Jones, M. O'Hare, D. M. Kammen, Science 2006, 311, 506;
7. d) D. Pimentel, T. W. Patzek, Nat. Resour. Res. 2005, 14, 65.
8. J. N. Chheda, G. W. Huber, J. A. Dumesic, Angew. Chem. 2007, 119, 7298;
9. Angew. Chem. Int. Ed. 2007, 46, 7164.
10. Y. Román-Leshkov, C. J. Barrett, Z. Y. Liu, J. A. Dumesic, Nature 2007, 447, 982.
11. H. Zhao, J. E. Holladay, H. Brown, Z. C. Zhang, Science 2007, 316, 1597.
12. J. N. Chheda, Y. Román-Leshkov, J. A. Dumesic, Green Chem. 2007, 9, 342.
13. J. Doerfler, H. V. Amorim, Zuckerindustrie 2007, 132, 694.
14. In practice this may not be a crucial parameter. Since the only reagent consumed in this process is hydrogen chloride, a flow reactor could be envisaged where the saccharide is continuously introduced, 1-4 are continuously removed, and the concentration of HCl is held constant by introduction of the gas into the reactor. A preliminary modeling study of this process is included in the Supporting Information.
15. G. J. M. Gruter, F. Dautzenberg, Eur. Pat. Appl., 2007, 1834950A1.
16. Avantium Technologies press release: http://www.avantium.com/index.php?p= 115&n=2.
17. The literature yield for this reaction is up to 95%, depending on which solvent is used: K. Hamada, G. Suzukamo, K. Fujisawa, Eur. Pat. Appl., 1982, 44186A1.
18. Jap. P. 58013576, 1983.
19. 13C NMR, and analysis by ASTM D4208 (oxygen bomb combustion selective electrode method) shows that the chlorine content is <0.5%.
20. J. M. de Man, Principles of Food Chemistry, 3rd ed., Springer, Heidelberg, 1999.
21. K. Michail, V. Matzi, A. Maier, R. Herwig, J. Greilberger, H. Juan, O. Kunert, R. Wintersteiger, Anal. Bioanal. Chem. 2007, 387, 2801.
22. H. J. H. Fenton, M. Gostling, J. Chem. Soc. Trans. 1901, 79, 807.
23. H. Hibbert, H. S. Hill, J. Am. Chem. Soc. 1923, 45, 176.
24. For example: K. Sanda, L. Rigal, A. Gaset, J. Chem. Technol. Biotechnol. 1992, 55, 139.
25. B. F. M. Kuster, H. J. C. Van der Steen, Staerke 1977, 29, 99.
26. HMFand CMFare also readily interconvertable: a) K. Sanda, L. Rigal, A. Gaset, Carbohydr. Res. 1989, 187, 15;
27. b) W. N. Haworth, W. G. M. Jones, J. Chem. Soc. 1944, 667.
28. 2-(2-Hydroxyacetyl)furan (3) is a well-known aroma component of several natural substances, for example, toasted oak in wine barrels: I. Cutzach, P. Chatonnet, R. Henry, D. Dubourdieu, J. Agric. Food Chem. 1999, 47, 1663.
29. Levulinic acid is a well-studied derivative of cellulosic biomass and is considered a promising building block for bio-derived polymers and fuel additives; see: Biorefineries-Industrial Processes and Products: Status Quo and Future Directions (Eds.: B. Kamm, P. R. Gruber, M. Kamm), Wiley-VCH, Weinheim, 2007.