Sustainable solvent systems for use in tandem carbohydrate dehydration hydrogenation

ACS Sustainable Chemistry and Engineering

Volumn 1, Issue 5, 2013, Pages 554-560

  Tucker, Mark H ^a   Alamillo, Ricardo ^a   Crisci, Anthony J ^a,b   Gonzalez, Gretchen M ^a   Scott, Susannah L ^b,c   Dumesic, James A ^a  

^a Wisconsin Electric Machines and Power Electronics Consortium   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c University of California   (United States)

Author keywords

5 Hydroxymethylfurfural; 13C NMR spectroscopy; Biomass; Fructose; Sustainable solvents; Tandem catalysis

Indexed keywords

5 HYDROXYMETHYL FURFURALS; AQUEOUS SOLVENTS; CATALYTIC HYDROGENATION; MIXED-SOLVENT SYSTEMS; TANDEM CATALYSIS; TETRA-HYDROFURAN; TETRAHYDROFURANS; TETRAHYDROFURFURYL ALCOHOLS;

BIOMASS; DEHYDRATION; FRUCTOSE; HYDROGENATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC SOLVENTS;

SOLVENTS;

EID: 84884213070     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/sc400044d     Document Type: Article

References (32)

1. Huber G. and Dale, B., The fuel of the future is grassoline. Sci. Am., 2009, 301.
2. Perlack, R. D.; Wright, L. L.; Turhollow, A. F.; Graham, R. L.; Stokes, B. J.; Erbach, D. C. Biomass as Feedstock for Bioenergy and Bioproducts Industry: The Technical Feasibility of a Billion-Ton Annual Supply; DOE/GO-102005-2135, ORNL/TM-2005/66; Office of Scientific and Technical Information, U.S. Department of Energy: Oak Ridge, TN, 2005.
3. Kuster, B. F. M. 5-Hydroxymethylfurfural (HMF). A review focussing on its manufacture. Starch/Staerke 1990, 42, 314-321.
4. Roman-Leshkov, Y.; Barrett, C. J.; Liu, Z. Y.; Dumesic, J. A. Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates. Nature 2007, 447, 982-985.
5. Roman-Leshkov, Y.; Cheda, J. N.; Dumesic, J. A. Phase modifiers promote efficient production of hydroxymethylfurfural from fructose. Science 2006, 312, 1933-1937.
6. van Dam, H. E.; Kieboom, A. P. G.; van Bekkum, H. The conversion of fructose and glucose in acidic media: Formation of hydroxymethylfurfural. Starch/Staerke 1986, 38, 95-101.
7. Roman-Leshkov, Y.; Chheda, J. N.; Dumesic, J. A. Phase modifiers promote efficient production of hydroxymethylfurfural from fructose. Science 2006, 312, 1933-1937.
8. Brown, D. W.; Floyd, A. J.; Kinsman, R. G.; Roshanali, Y. Dehydration reactions of fructose in non-aqueous media. J. Chem. Technol. Biotechnol. 1982, 32, 920-924.
9. Chheda, J. N.; Roman-Leshkov, Y.; Dumesic, J. A. Production of 5-hydroxymethylfurfural and furfural by dehydration of biomassderived mono-and poly-saccharides. Green Chem. 2007, 9, 342-350.
10. 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, 165-169.
11. Zhao, H. B.; Holladay, J. E.; Brown, H.; Zhang, Z. C. Metal chlorides in ionic liquid solvents convert sugars to 5-hydroxymethylfurfural. Science 2007, 316, 1597-1600.
12. Lai, L.; Zhang, Y. The production of 5-hydroxymethylfurfural from fructose in isopropyl alcohol: A green and efficient system. ChemSusChem 2011, 4, 1745-1748.
13. Tucker, M. H.; Crisci, A. J.; Wigington, B. N.; Phadke, N.; Alamillo, R.; Zhang, J.; Scott, S. L.; Dumesic, J. A. Acid-functionalized SBA-15-type periodic mesoporous organosilicas and their use in the continuous production of 5-hydroxymethylfurfural. ACS Catal. 2012, 2, 1865-1876.
14. Alamillo, R.; Tucker, M.; Chia, M.; Pagan-Torres, Y.; Dumesic, J. The selective hydrogenation of biomass-derived 5-hydroxymethylfurfural using heterogeneous catalysts. Green Chem. 2012, 14, 1413-1419.
15. Shimizu, K.-i.; Uozumi, R.; Satsuma, A. Enhanced production of hydroxymethylfurfural from fructose with solid acid catalysts by simple water removal methods. Catal. Comm. 2009, 10, 1849-1853.
16. Crisci, A.; Tucker, M.; Dumesic, J.; Scott, S. Bifunctional solid catalysts for the selective conversion of fructose to 5-hydroxymethylfurfural. Top. Catal. 2010, 53, 1185-1192.
17. Antal, M. J., Jr.; Mok, W. S.; Richards, G. N. Mechanism of formation of 5-(hydroxymethyl)-2-furaldehyde from D-fructose an sucrose. Carbohydr. Res. 1990, 199, 91-109.
18. Kuster, B. F. M. Dehydration of D-fructose (formation of 5-hydroxymethyl-2-furaldehyde and levulinic acid) 0.3. Influence of water concentration on dehydration of D-fructose. Carbohydr. Res. 1977, 54, 177-183.
19. Dais, P.; Perlin, A. S. Intramolecular hydrogen-bonding and solvation contributions to the relative stability of the beta-furanose form of D-fructose in dimethylsulfoxide. Carbohydr. Res. 1987, 169, 159-169.
20. Bicker, M.; Kaiser, D.; Ott, L.; Vogel, H. Dehydration of Dfructose to hydroxymethylfurfural in sub-and supercritical fluids. J. Supercrit. Fluids 2005, 36, 118-126.
21. Caratzoulas, S.; Vlachos, D. G. Converting fructose to 5-hydroxymethylfurfural: A quantum mechanics/molecular mechanics study of the mechanism and energetics. Carbohydr. Res. 2011, 346, 664-672.
22. Flood, A. E.; Johns, M. R.; White, E. T. Mutarotation of Dfructose in aqueous-ethanolic solutions and its influence on crystallisation. Carbohydr. Res. 1996, 288, 45-56.
23. Hyvonen, L.; Varo, P.; Koivistoinen, P. Tautomeric equilibria of D-glucose and D-fructose-NMR spectrometric measurements. J. Food Sci. 1977, 42, 657-659.
24. Patil, S. K. R.; Lund, C. R. F. Formation and growth of humans via aldol addition and condensation during acid-catalyzed conversion of 5-hydroxymethylfurfural. Energy Fuels 2011, 25, 4745-4755.
25. Gattuso, G.; Nepogodiev, S. A.; Stoddart, J. F. Synthetic cyclic oligosaccharides. Chem. Rev. 1998, 98, 1919-1958.
26. Pagan-Torres, Y. J.; Wang, T.; Gallo, J. M. R.; Shanks, B. H.; Dumesic, J. A. Production of 5-hydroxymethylfurfural from glucose using a combination of Lewis and Broønsted acid catalysts in water in a biphasic reactor with an alkylphenol solvent. ACS Catal 2012, 2, 930-934.
27. Barclay, T.; Ginic-Markovic, M.; Johnston, M. R.; Cooper, P.; Petrovsky, N. Observation of the keto tautomer of d-fructose in D2O using 1H NMR spectroscopy. Carbohydr. Res. 2012, 347, 136-141.
28. Amarasekara, A. S.; Williams, L. D.; Ebede, C. C. Mechanism of the dehydration of D-fructose to 5-hydroxymethylfurfural in dimethyl sulfoxide at 150 C: An NMR study. Carbohydr. Res. 2008, 343, 3021-3024.
29. Shimizu, K.-i.; Uozumi, R.; Satsuma, A. Enhanced production of hydroxymethylfurfural from fructose with solid acid catalysts by simple water removal methods. Catal. Commun. 2009, 10, 1849-1853.
30. Funcke, W.; von Sonntag, C.; Triantaphylides, C. Detection of the open-chain forms of D-fructose and L-sorbose in aqueous solution by using 13C NMR spectroscopy. Carbohydr. Res. 1979, 75, 305-309.
31. Schneider, B.; Lichtenthaler, F. W.; Steinle, G.; Schiweck, H. Studies on ketoses, 1 distribution of furanoid and pyranoid tautomers of D-fructose in water, dimethyl sulfoxide, and pyridine via 1H NMR intensities of anomeric hydroxy groups in [D6]DMSO. Liebigs Ann. Chem. 1985, 1985, 2443-2453.
32. Flood, A. E.; Johns, M. R.; White, E. T. Mutarotation of Dfructose in aqueous-ethanolic solutions and its influence on crystallisation. Carbohydr. Res. 1996, 288, 45-56.