Mechanisms and energetics for brønsted acid-catalyzed glucose condensation, dehydration and isomerization reactions

Topics in Catalysis

Volumn 55, Issue 3-4, 2012, Pages 218-226

  Qian, Xianghong ^a  

^a 3202 Bell Engineering Center   (United States)

Author keywords

Condensation reaction; Dehydration reaction; Glucose; HMF; Isomerization; Mutarotation

Indexed keywords

DEHYDRATION REACTIONS; GLUCOSE REACTIONS; HMF; ISOMERIZATION REACTION; MUTAROTATION; OPEN CHAIN; SOLVENT INDUCED; SOLVENT MOLECULES;

BIOCONVERSION; CONDENSATION; CONDENSATION REACTIONS; DEHYDRATION; FRUCTOSE; ISOMERIZATION; MECHANISMS; PROTONATION;

GLUCOSE;

EID: 84865996450     PISSN: 10225528     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11244-012-9790-6     Document Type: Conference Paper

References (36)

1. Chheda JN, Roman-Leshkov Y, Dumesic JA (2007) Production of 5-hydroxymethylfurfural and furfural by dehydration of biomass-derived mono- and poly-saccharides. Green Chem 9: 342-350
2. Corma A, Iborra S, Velty A (2007) Chemical routes for the transformation of biomass into chemicals. Chem Rev 107:2411-2502 (Pubitemid 47033769)
3. Bicker M, Hirth J, Vogel H (2003) Dehydration of fructose to 5-hydroxymethylfurfural in sub- and supercritical acetone. Green Chem 5:280-284 (Pubitemid 37487496)
4. Chheda JN, Huber GW, Dumesic JA (2007) Liquid-phase catalytic processing of biomass-derived oxygenated hydrocarbons to fuels and chemicals. Angew Chem Int Ed 46:7164-7183 (Pubitemid 47517906)
5. Chheda JN, Dumesic JA (2007) An overview of dehydration, aldol-condensation and hydrogenation processes for production of liquid alkanes from biomass-derived carbohydrates. Catal Today 123:59-70 (Pubitemid 46756168)
6. Zhao HB, Holladay JE, Brown H, Zhang ZC (2007) Metal chlorides in ionic liquid solvents convert sugars to 5-hydroxymethylfurfural. Science 316:1597-1600 (Pubitemid 46982028)
7. van Damm HE, Kieboom APG, van Bekkum H (1986) The conversion of fructose and glucose in acidic media: formation of hydroxymethylfurfural. Starch 38:95-101
8. Szmant HH, Chundury DD (1981) The preparation of 5- hydroxymethylfurfuraldehyde from high fructose corn syrup and other carbohydrates. J Chem Technol Biotechnol 31:135-145
9. Seri K, Inoue Y, Ishida H (2001) Catalytic activity of Lanthanide( III) ions for the dehydration of hexose to 5-hydroxymethyl- 2-furaldehyde in water. Bull Chem Soc Jpn 74:1145-1150 (Pubitemid 32702735)
10. Kuster BFM (1990) 5-Hydroxymethylfurfural (HMF). A Review focussing on its manufacture. Starch 42:314-321
11. Chheda JN, Barrett CJ, Huber GW, Dumesic JA (2006) Production of large, water-soluble intermediates from carbohydratederived compounds by sequential condensation/hydrogenation. Abs Pap Am Chem Soc 231:1
12. Liu DJ, Nimlos MR, Johnson DK, Himmel ME, Qian XH (2010) Free energy landscape for glucose condensation reactions. J Phys Chem A 114:12936-12944
13. Qian XH (2011) Mechanisms and energetics for acid catalyzed beta-D-glucose conversion to 5-hydroxymethylfurfurl. J Phys Chem A 115:11740-11748
14. Qian XH, Nimlos MR, Johnson DK, Himmel ME (2005) Acidic sugar degradation pathways. Appl Biochem Biotechnol 121: 989-997
15. Qian XH, Nimlos MR, Davis M, Johnson DK, Himmel ME (2005) Ab initio molecular dynamics simulations of beta-D-glucose and beta-D-xylose degradation mechanisms in acidic aqueous solution. Carbohydr Res 340:2319-2327 (Pubitemid 41268656)
16. Qian X, Nimlos MR (2008) Mechanisms of xylose and xylooligomer degradation during acid pretreatment. In: Himmel M (ed) Biomass recalcitrance. Blackwell Publishing Ltd, Oxford
17. Dong H, Nimlos MR, Himmel ME, Johnson DK, Qian X (2009) The effects of water on b-D-xylose condensation reactions. J Phys Chem A 113:8577-8585
18. Qian XH, Johnson DK, Himmel ME, Nimlos MR (2010) The role of hydrogen-bonding interactions in acidic sugar reaction pathways. Carbohydr Res 345:1945-1951
19. Yong G, Zhang YG, Ying JY (2008) Efficient catalytic system for the selective production of 5-hhydroxymethylfurfural from glucose and fructose. Angew Chem Int Ed 47:9345-9348
20. Binder JB, Raines RT (2009) Simple chemical transformation of lignocellulosic biomass into furans for fuels and chemicals. J Am Chem Soc 131:1979-1985
21. Li CZ, Zhang ZH, Zhao ZBK (2009) Direct conversion of glucose and cellulose to 5-hydroxymethylfurfural in ionic liquid under microwave irradiation. Tetrahedron Lett 50:5403-5405
22. Hu SQ, Zhang ZF, Song JL, Zhou YX, Han BX (2009) Efficient conversion of glucose into 5-hydroxymethylfurfural catalyzed by a common Lewis acid SnCl(4) in an ionic liquid. Green Chem 11:1746-1749
23. Kim B, Jeong J, Lee D, Kim S, Yoon H-J, Lee Y-S, Cho JK (2011) Direct transformation of cellulose into 5-hydroxymethyl- 2-furfural using a combination of metal chlorides in imidazolium ionic liquid. Green Chem 13:1503-1506
24. Zhang YT, Du HB, Qian XH, Chen EYX (2010) Ionic liquidwater mixtures: enhanced K-w for efficient cellulosic biomass conversion. Energy Fuels 24:2410-2417
25. Moliner M, Roman-Leshkov Y, Davis ME (2010) Tin-containing zeolites are highly active catalysts for the isomerization of glucose in water. Proc Natl Acad Sci USA 107:6164-6168
26. CarR,ParrinelloM(1985)Unified approach formolecular dynamics and density-functional theory. Phys Rev Lett 55:2471-2474
27. Iannuzzi M, Laio A, Parrinello M (2003) Efficient exploration of reactive potential energy surfaces using car-parrinello molecular dynamics. Phys Rev Lett 90:238302
28. Dong H, Qian X (2011) Ab initio molecular dynamics investigation of xylan hydrolysis. In Nimlos MR, Crowley MF (eds) Computational modeling in lignocellulosic biofuel production. ACS Symposium Series
29. Antal MJ, Leesomboon T, Mok WS, Richards GN (1991) Mechanism of formation of 2-furaldehyde from D-xylose. Carbohydr Res 217:71-85
30. Pilath HM, Nimlos MR, Mittal A, Himmel ME, Johnson DK (2010) Glucose reversion reaction kinetics. J Agric Food Chem 58:6131-6140
31. Ballash NM, Robertso Eb (1973) Mutarotation of glucose in dimethylsulfoxide and water mixtures. Can J Chem Revue Canadienne De Chimie 51:556-564
32. Antal MJ, Mok WSL, Richards GN (1990) Kinetic-studies of the reactions of ketoses and aldoses in water at high-temperature. 1. Mechanism of formation of 5-(hydroxymethyl)-2-furaldehyde from D-fructose and sucrose. Carbohydr Res 199:91-109
33. Feather MS (1970) The conversion of D-xylose and D-glucuronic acid to 2-furaldehyde. Tetrahedron Lett 48:4143-4145
34. Feather MS, Harris DW, Nichols SB (1972) Routes of conversion of D-xylose, hexuronic acids, and L-ascorbic acid to 2-furaldehyde. J Org Chem 37:1606-1608
35. Feather MS, Harris JF (1970) Mechanism of conversion of hexoses into 5-(hydroxymethyl)-2-furaldehyde and metasaccharinic acid. Carbohydr Res 15:304-309
36. Harris DW, Feather MS (1974) Intramolecular c-2 - c-1 hydrogen transfer-reactions during conversion of aldoses to 2-furaldehydes. J Org Chem 39:724-725