Acid-catalyzed conversion of Xylose in 20 solvents: Insight into interactions of the solvents with Xylose, furfural, and the acid catalyst

ACS Sustainable Chemistry and Engineering

Volumn 2, Issue 11, 2014, Pages 2562-2575

  Hu, Xun ^a   Westerhof, Roel J M ^a   Dong, Dehua ^a   Wu, Liping ^a   Li, Chun Zhu ^a  

^a CURTIN UNIVERSITY   (Australia)

Author keywords

Acidic resin catalyst; Furfural; Levulinic acid; Polymerization; Reaction network; Solvents; Xylose

Indexed keywords

AROMATIC HYDROCARBONS; CATALYSIS; CATALYSTS; ESTERS; ETHERS; FURFURAL; KETONES; ORGANIC POLLUTANTS; POLYMERIZATION; REACTION INTERMEDIATES; RESINS; SOLVENTS; XYLOSE;

ACID-CATALYZED CONVERSIONS; ACIDIC RESIN; CARBONYL GROUPS; LEVULINIC ACID; PROLONGED REACTION; REACTION NETWORK; REACTIVE INTERMEDIATE; TRANSFER HYDROGENATIONS;

ALDEHYDES;

EID: 84908498297     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/sc5004659     Document Type: Article

References (47)

1. Alonso, D. M.; Wettstein, S. G.; Mellmer, M. A.; Gurbuz, E. I.; Dumesic, J. A. Integrated conversion of hemicellulose and cellulose from lignocellulosic biomass Energy Environ. Sci. 2013, 6, 76-80
2. Climent, M. J.; Corma, A.; Iborra, S. Conversion of biomass platform molecules into fuel additives and liquid hydrocarbon fuels Green Chem. 2014, 16, 516-547
3. Cheng, Y.-T.; Huber, G. W. Production of targeted aromatics by using Diels-Alder classes of reactions with furans and olefins over ZSM-5 Green Chem. 2012, 14, 3114-3125
4. Melero, J. A.; Iglesias, J.; Garcia, A. Biomass as renewable feedstock in standard refinery units. Feasibility, opportunities and challenges Energy Environ. Sci. 2012, 5, 7393-7420
5. Dias, A. S.; Pillinger, M.; Valente, A. A. Dehydration of xylose into furfural over micro-mesoporous sulfonic acid catalysts J. Catal. 2005, 229, 414-423
6. Lima, S.; Antunes, M. M.; Fernandes, A.; Pillinger, M.; Ribeiro, M. F.; Valente, A. A. Catalytic cyclodehydration of xylose to furfural in the presence of zeolite H-Beta and a micro/mesoporous Beta/TUD-1 composite material Appl. Catal. A-Gen. 2010, 388, 141-148
7. Lima, S.; Pillinger, M.; Valente, A. A. Dehydration of D-xylose into furfural catalysed by solid acids derived from the layered zeolite Nu-6 (1) Catal. Commun. 2008, 9, 2144-2148
8. ONeill, R.; Ahmad, M. N.; Vanoye, L.; Aiouache, F. Kinetics of aqueous phase dehydration of xylose into furfural catalyzed by ZSM-5 zeolite Ind. Eng. Chem. Res. 2009, 48, 4300-4306
9. 2-stripping Green Chem. 2012, 14, 3132-3140
10. Melero, J. A.; Iglesias, J.; Garcia, A. Biomass as renewable feedstock in standard refinery units. Feasibility, opportunities and challenges Energy Environ. Sci. 2012, 5, 7393-7420
11. Cai, C. M.; Zhang, T.; Kumar, R.; Wyman, C. E. THF co-solvent enhances hydrocarbon fuel precursor yields from lignocellulosic biomass Green Chem. 2013, 15, 3140-3145
12. Hu, X.; Lievens, C.; Li, C.-Z. Acid-Catalyzed conversion of xylose in methanol-rich medium as part of biorefinery ChemSusChem 2012, 5, 1427-1434
13. Karinen, R.; Vilonen, K.; Niemela, M. Biorefining: heterogeneously catalyzed reactions of carbohydrates for the production of furfural and hydroxymethylfurfural ChemSusChem 2011, 4, 1002-1016
14. Danon, B.; Marcotullio, G.; Jong, W. Mechanistic and kinetic aspects of pentose dehydration towards furfural in aqueous media employing homogeneous catalysis Green Chem. 2014, 16, 39-54
15. 3 in acetic acid steam Green Chem. 2013, 15, 727-737
16. Kobayashi, H.; Fukuoka, A. Synthesis and utilisation of sugar compounds derived from lignocellulosic biomass Green Chem. 2013, 15, 1740-1763
17. Hu, X.; Li, C.-Z. Levulinic esters from the acid-catalysed reactions of sugars and alcohols as part of a bio-refinery Green Chem. 2011, 13, 1676-1679
18. Climent, M. J.; Corma, A.; Iborra, S. Conversion of biomass platform molecules into fuel additives and liquid hydrocarbon fuels Green Chem. 2014, 16, 516-547
19. Hu, X.; Mourant, D.; Gunawan, R.; Wu, L.; Wang, Y.; Lievens, C.; Li, C.-Z. Production of value-added chemicals from bio-oil via acid catalysis coupled with liquid-liquid extraction RSC Adv. 2012, 2, 9366-9370
20. Weingarten, R.; Cho, J.; Conner, W. C., Jr.; Huber, G. W. Kinetics of furfural production by dehydration of xylose in a biphasic reactor with microwave heating Green Chem. 2010, 12, 1423-1429
21. Sádaba, I.; Lima, S.; Valente, A. A.; Granados, M. L. Catalytic dehydration of xylose to furfural: vanadyl pyrophosphate as source of active soluble species Carbohydr. Res. 2011, 346, 2785-2791
22. Qi, X.; Watanabe, M.; Aida, T. M.; Smith, R. L., Jr. Catalytic dehydration of fructose into 5-hydroxymethylfurfural by ion-exchange resin in mixed-aqueous system by microwave heating Green Chem. 2008, 10, 799-805
23. Li, B.; Varanasi, S.; Relue, P. High yield aldose-ketose transformation for isolation and facile conversion of biomass sugar to furan Green Chem. 2013, 15, 2149-2157
24. Saha, B.; Abu-Omar, M. M. Advances in 5-hydroxymethylfurfural production from biomass in biphasic solvents Green Chem. 2014, 16, 24-38
25. Chheda, J. N.; Román-Leshkov, Y.; Dumesic, J. A. Production of 5-hydroxymethylfurfural and furfural by dehydration of biomass-derived mono-and poly-saccharides Green Chem. 2007, 9, 342-350
26. Lam, E.; Majid, E.; Leung, A. C. W.; Chong, J. H.; Mahmoud, K. A.; Luong, J. H. T. Synthesis of furfural from xylose by heterogeneous and reusable nafion catalysts ChemSusChem 2011, 4, 535-541
27. Gürbüz, E. I.; Wettstein, S. G.; Dumesic, J. A. Conversion of hemicellulose to furfural and levulinic acid using biphasic reactors with alkylphenol solvents ChemSusChem 2012, 5, 383-387
28. Agirrezabal-Telleria, I.; Requies, J.; Güemez, M. B.; Arias, P. L. Pore size tuning of functionalized SBA-15 catalysts for the selective production of furfural from xylose Appl. Catal., B 2012, 115-116, 169-178
29. Dias, A. S.; Lima, S.; Pillinger, M.; Valente, A. A. Modified versions of sulfated zirconia as catalysts for the conversion of xylose to furfural Catal. Lett. 2007, 114, 151-160
30. Choudhary, V.; Pinar, A. B.; Sandler, S. I.; Vlachos, D. G.; Lobo, R. F. Xylose isomerization to xylulose and its dehydration to furfural in aqueous media ACS Catal. 2011, 1, 1724-1728
31. Brandt, A.; Gräsvik, J.; Hallett, J. P.; Welton, T. Deconstruction of lignocellulosic biomass with ionic liquids Green Chem. 2013, 15, 550-583
32. Stark, A. Ionic liquids in the biorefinery: A critical assessment of their potential Energy Environ. Sci. 2011, 4, 19-32
33. Dee, S.; Bell, A. T. Effects of reaction conditions on the acid-catalyzed hydrolysis of miscanthus dissolved in an ionic liquid Green Chem. 2011, 13, 1467-1475
34. Tadesse, H.; Luque, R. Advances on biomass pretreatment using ionic liquids: An overview Energy Environ. Sci. 2011, 4, 3913-3929
35. Hu, X.; Wu, L.; Wang, Y.; Mourant, D.; Lievens, C.; Gunawan, R.; Li, C.-Z. Mediating acid-catalyzed conversion of levoglucosan into platform chemicals with various solvents Green Chem. 2012, 14, 3087-3098
36. Maldonado, G. M. G.; Assary, R. S.; Dumesic, J.; Curtiss, L. A. Experimental and theoretical studies of the acid-catalyzed conversion of furfuryl alcohol to levulinic acid in aqueous solution Energy Environ. Sci. 2012, 5, 6981-6989
37. Hu, X.; Mourant, D.; Wang, Y.; Wu, L.; Chaiwat, W.; Gunawan, R.; Gholizadeh, M.; Lievens, C.; Garcia-Perez, M.; Li, C.-Z. Acid-catalysed treatment of the mallee leaf bio-oil with methanol: Effects of molecular structure of carboxylic acids and esters on their conversion Fuel Process. Technol. 2013, 106, 569-576
38. Wang, Y.; Li, X.; Mourant, D.; Gunawan, R.; Zhang, S.; Li, C.-Z. Formation of aromatic structures during the pyrolysis of bio-oil Energy Fuels 2012, 26, 241-247
39. Song, J.; Fan, H.; Ma, J.; Han, B. Conversion of glucose and cellulose into value-added products in water and ionic liquids Green Chem. 2013, 15, 2619-2635
40. Lange, J.-P.; Heide, E.; Buijtenen, J.; Price, R. Furfural-A promising platform for lignocellulosic biofuels ChemSusChem 2012, 5, 150-166
41. Wang, T.; Noltea, M. W.; Shanks, B. H. Catalytic dehydration of C 6 carbohydrates for the production of hydroxymethylfurfural (HMF) as a versatile platform chemical Green Chem. 2014, 16, 548-572
42. Marcotullio, G.; Jong, W. D. Chloride ions enhance furfural formation from D-xylose in dilute aqueous acidic solutions Green Chem. 2010, 12, 1739-1746
43. Hu, X.; Song, Y.; Wu, L.; Gholizadeh, M.; Li, C.-Z. One-pot synthesis of levulinic acid/ester from C5 carbohydrates in a methanol medium ACS Sustainable Chem. Eng. 2013, 1, 1593-1599
44. Hu, X.; Gunawan, R.; Mourant, D.; Li, X.; Zhang, S.; Li, C.-Z. Effects of temperature on the yields and properties of bio-oil from the fast pyrolysis of mallee bark Fuel 2012, 97, 512-522
45. Hu, X.; Wang, Y.; Mourant, D.; Gunawan, R.; Lievens, C.; Chaiwat, W.; Gholizadeh, M.; Wu, L.; Li, X.; Li, C.-Z. Polymerization on heating up of bio-oil: A model compound study AIChE J. 2013, 59, 888-900
46. Mohan, D.; Pittman, C. U., Jr.; Steele, P. H. Pyrolysis of wood/biomass for bio-oil: A critical review Energy Fuels 2006, 20, 848-889
47. Corain, B.; Zecca, M.; Jerabek, K. Catalysis and polymer networks-the role of morphology and molecular accessibility J. Mol. Catal. A: Chem. 2001, 177, 3-20