Catalytic transformation of carbohydrates and lignin in ionic liquids

Wiley Interdisciplinary Reviews: Energy and Environment

Volumn 2, Issue 6, 2013, Pages 655-672

  Zhang, Z Conrad ^a  

^a KiOR Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOMASS; CARBOHYDRATES; CELLULOSE; CHLORINE COMPOUNDS; DISSOLUTION; HYDROGEN BONDS; LIGNIN;

BIOMASS COMPONENTS; CATALYST SYSTEM; CATALYTIC CONVERSION; CATALYTIC TRANSFORMATION; FUNCTIONAL PROPERTIES; HIGH SOLUBILITY; HYDROGEN-BOND BASICITY; LIGNOCELLULOSIC BIOMASS;

IONIC LIQUIDS;

EID: 84885902980     PISSN: 20418396     EISSN: 2041840X     Source Type: Journal    
DOI: 10.1002/wene.67     Document Type: Review

References (95)

1. U.S. Department of Energy. U.S. billion-ton update: biomass supply for a bioenergy and bioproducts industry. Perlack RD, Stokes BJ (Leads), ORNL/TM-2011/224. Oak Ridge, TN: Oak Ridge National Laboratory; 2011: 227.
2. U.S. Department of Energy. Biomass multi-year program plan. 2011. Available at: http://www1.eere.energy.gov/biomass/pdfs/mypp_november_2011.pdf. (Accessed December 18, 2012).
3. Fukuoka A, Dhepe PL. Catalytic conversion of cellulose into sugar alcohols. Angew Chem Int Ed 2006, 45:5161-5163.
4. Geboers J, Van de Vyver S, Carpentier K, de Blochouse K, Jacobs P, Sels B. Efficient catalytic conversion of concentrated cellulose feeds to hexitols with heteropoly acids and Ru on carbon. Chem Commun 2010, 46:3577-3579.
5. Palkovits R, Tajvidi K, Ruppert AM, Procelewska J. Heteropoly acids as efficient acid catalysts in the one-step conversion of cellulose to sugar alcohols. Chem Commun 2011, 47:576-578.
6. Luo C, Wang S, Liu H. Cellulose conversion into polyols catalyzed by reversibly formed acids and supported ruthenium clusters in hot water. Angew Chem Int Ed 2007, 46:7636-7639.
7. Deng W, Tan X, Fang W, Zhang Q, Wang Y. Conversion of cellulose into sorbitol over carbon nanotube-supported ruthenium catalyst. Catal Lett 2009, 133:167-174.
8. Ji N, Zhang T, Zheng M, Wang A, Wang H, Wang X, Chen JG. Direct catalytic conversion of cellulose into ethylene glycol using nickel-promoted tungsten carbide catalysts. Angew Chem Int Ed 2008, 47:8510-8513.
9. Ji N, Zhang T, Zheng M, Wang A, Wang H, Wang X, Shu Y, Stottlemyer AL, Chen JG. Catalytic conversion of cellulose into ethylene glycol over supported carbide catalysts. Catal Today 2009, 147:77-85.
10. Liu Y, Luo C, Liu H. Tungsten trioxide promoted selective conversion of cellulose into propylene glycol and ethylene glycol on a ruthenium catalyst. Angew Chem Int Ed 2012, 51:3249-3253.
11. Swatloski RP, Spear SK, Holbrey JD, Rogers RD. Dissolution of cellose with ionic liquids. J Am Chem Soc 2002, 124:4974-4975.
12. Pinkert A, Marsh KN, Pang S, Staiger MP. Ionic liquids and their interaction with cellulose. Chem Rev 2009, 109:6712-6728.
13. Pu Y, Jiang N, Ragauskas AJ, Wood J. Ionic liquid as a green solvent for lignin. Chem Technol 2007, 27:23-33.
14. Wang H, Gurau G, Rogers RD. Ionic liquid processing of cellulose. Chem Soc Rev 2012, 41:1519-1537.
15. Su Y, Brown HM, Huang XW, Zhou XD, Amonette JE, Zhang ZC. Single-step conversion of cellulose to 5-hydroxymethylfurfural (HMF), a versatile platform chemical. Appl Catal A 2009, 361:117-122.
16. Su Y, Brown HM, Li G, Zhou X-d, Amonette JE, Fulton JL, Camaioni DM, Zhang ZC. Accelerated cellulose depolymerization catalyzed by paired metal chlorides in ionic liquid solvent. Appl Catal A Gen 2011, 391:436-442.
17. Li CZ, Wang Q, Zhao ZK. Acid in ionic liquid: an efficient system for hydrolysis of lignocellulose. Green Chem 2008, 10:177-82.
18. Vancov T, Alston A-S, Brown T, McIntosh S. Use of ionic liquids in converting lignocellulosic material to biofuels. Renew Energy 2012, 45:1-6.
19. Seddon KR. Ionic liquids for clean technology. J Chem Technol Biotechnol 1997, 68:351-356.
20. Rogers RD, Seddon KR. Ionic liquids-solvents of the future? Science 2003, 302:792-793.
21. Welton T. Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem Rev 1999, 99:2071-2083.
22. Zhang ZC. Catalysis in ionic liquids. Adv Catal 2006, 49:153-237.
23. Fink HP, Weigel P, Purz HJ, Ganster J. Structure formation of regenerated cellulose materials from NMMO-solutions. Prog Polym Sci 2001, 26:1473-1524.
24. Qi H, Sui X, Yuan J, Wei Y, Zhang L. Electrospinning of cellulose-based fibers from NaOH/urea aqueous system. Macromol Mater Eng 2010, 295:695-700.
25. McCormick CL, Dawsey TR. Preparation of cellulose derivatives via ring-opening reactions with cyclic reagents in lithium chloride/N, N-dimethylacetamide. Macromolecules 1990, 23:3606-3610.
26. Zhang QH, Benoit M, Vigier KDO, Barrault J, Jerome F. Green and inexpensive choline-derived solvents for cellulose decrystallization. Chem Eur J 2012, 18:1043-1046.
27. Binder JB, Raines RT. Simple chemical transformation of lignocellulosic biomass into furans for fuels and chemicals. J Am Chem Soc 2009, 131:1979-1985.
28. Zhao HB, Holladay JE, Brown H, Zhang ZC. Metal chlorides in ionic liquid solvents convert sugars to 5-hydroxymethylfurfural. Science 2007, 316:1597-1600.
29. Zhang ZC. Emerging catalysis for 5-HMF formation from cellulosic carbohydrates. In: Suib SL, ed. New and Future Developments in Catalysis: Catalytic Biomass Conversion. In press.
30. Li GS, Camaioni DM, Amonette JE, Zhang ZC, Johnson TJ, Fulton JL. [CuCln](2-n) ion-pair species in 1-ethyl-3-methylimidazolium chloride ionic liquid-water mixtures: ultraviolet-visible, x-ray absorbtion fine structure, and density functional theory characterization. J Phys Chem B 2010, 114:12614-12622.
31. Brugger J, McPhail DC, Black J, Spiccia L. UV-Vis-NIR spectroscopic study of Cu(II) complexing in LiCl brines between 20°C and 90°C. Geochim Cosmochim Acta 2001, 65:2691-2708.
32. α from synchrotron x-ray and neutron fiber diffraction. J Am Chem Soc 2003, 125:14300-16306.
33. Notley SM, Pettersson B, Wagberg L. Direct measurement of attractive van der Waals' forces between regenerated cellulose surfaces in an aqueous environment. J Am Chem Soc 2004, 126:13930-13931.
34. Gan Q, Allen SJ, Taylor G. Analysis of process integration and intensification of enzymatic cellulose hydrolysis in a membrane bioreactor. J Chem Technol Biotechnol 2005, 80:688-698.
35. Saeman JF, Bubl JL, Harris EE. Quantitative saccharification of wood and cellulose. Ind Eng Chem Anal Ed 1945, 17:35-37.
36. Zhao H, Kwak JH, Zhang ZC, Brown HM, Arey BW, Holladay JE. Studying cellulose fiber structure by SEM, XRD, NMR and acid hydrolysis. Carbohydr Polym 2007, 68:235-241.
37. Sanchez G, Pilcher L, Roslander C, Modig T, Galbe M, Liden G. Dilute-acid hydrolysis for fermentation of the Bolivian straw material Paja Brava. Bioresour Technol 2004, 93:249-256.
38. Zhao H, Holladay JE, Kwak JH, Zhang ZC. Inverse temperature-dependent pathway of cellulose decrystallization in trifluoroacetic acid. J Phys Chem B 2007, 111:5295-5300.
39. Vassilev SV, Baxter D, Andersen LK, Vassileva CG, Morgan TJ. An overview of the organic and inorganic phase composition of biomass. Fuel 2012, 94:1-33.
40. Gierer J. Chemical aspects of kraft pulping. Wood Sci Technol 1980, 14:241-266.
41. Chakar FS, Ragauskas AJ. Review of current and future softwood kraft lignin process chemistry. Ind Crops Prod 2004, 20:131-141.
42. Adler E. Lignin chemistry-past, present and future. Wood Sci Technol 1977, 11:169-218.
43. Sluiter JB, Ruiz RO, Scarlata CJ, Sluiter AD, Templeton DW. Compositional analysis of lignocellulosic feedstocks. 1. Review and description of methods. J Agric Food Chem 2010, 58:9043-9053.
44. Pedersen M, Meyer AS. Lignocellulose pretreatment severity-relating pH to biomatrix opening. New Biotechnol 2010, 27:739-750.
45. Remsing RC, Swatloski RP, Rogers RD, Moyna G. Can ionic liquids dissolve wood? Chem Commun 2006, 1271-1273.
46. Zhao H, Jones CIL, Baker GA, Xia S, Olubajo O, Person VN. Regenerating cellulose from ionic liquids for an accelerated enzymatic hydrolysis. J Biotechnol 2009, 139:47-54.
47. Maki-Arvela P, Anugwom I, Virtanen P, Sjoholm R, Mikkola JP. Dissolution of lignocellulosic materials and its constituents using ionic liquids-a review. Ind Crop Prod 2010, 32:175-201.
48. Turner MB, Spear SK, Huddleston JG, Holbrey JD, Rogers RD. Ionic liquid salt-induced inactivation and unfolding of cellulase from Trichoderma reesei. Green Chem 2003, 5:443-447.
49. Erdmenger T, Haensch C, Hoogenboom R, Schubert US. Homogeneous tritylation of cellulose in 1-butyl-3-methylimidazolium chloride. Macromol Biosci 2007, 7:440-445.
50. Fukaya Y, Hayashi K, Wada M, Ohno H. Cellulose dissolution with polar ionic liquids under mild conditions: required factors for anions. Green Chem 2008, 10:44-46.
51. Zhao H, Baker GA, Song Z, Olubajo O, Crittle T, Peters D. Designing enzymecompatible ionic liquids that can dissolve carbohydrates. Green Chem. 2008, 10:696-705.
52. Weerachanchai P, Leong SSJ, Chang MW, Ching CB, Lee J-M. Improvement of biomass properties by pretreatment with ionic liquids for bioconversion process. Bioresour Technol 2012, 111:453-459.
53. Luo HM, Li YQ, Zhou CR. Study on the dissolubility of the cellulose in the functionalized ionic liquid. Polym Mater Sci Eng 2005, 21:233-235.
54. Awad WA, Gilman JW, Nyden M, Harris Jr. RH, Sutto TE, Callahan J, Trulove PC, De Long HC, Fox DM. Thermal degradation studies of alkyl-imidazolium salts and their application in nanocomposites. Thermochim Acta 2004, 409:3-11.
55. Kroon MC, Buijs W, Peters CJ, Witkamp G-J. Quantum chemical aided prediction of the thermal decomposition mechanisms and temperatures of ionic liquids. Thermochim Acta 2007, 465:40-47.
56. Wendler F, Todi L-N, Meister F. Thermostability of imidazolium ionic liquids as direct solvents for cellulose. Thermochim Acta 2012, 528:76-84.
57. Cruz H, Fanselow M, Holbrey JD, Seddon KR. Determining relative rates of cellulose dissolution in ionic liquids through in situ viscosity measurement. Chem Commun 2012, 48:5620-5622.
58. FitzPatrickm M, Champagne P, Cunningham MF. The effect of sub-critical carbon dioxide on the dissolution of cellulose in the ionic liquid 1-ethyl-3-methylimidazolium acetate. Cellulose 2012, 19:37-44.
59. Karatzos SK, Edye LA, Wellard RM. The undesirable acetylation of cellulose by the acetate ion of 1-ethyl-3-methylimidazolium acetate. Cellulose 2012, 19:307-312.
60. Zhao D, Li H, Zhang J, Fu LL, Liu MS, Fu JT, Ren PB. Dissolution of cellulose in phosphate-based ionic liquids. Carbohydr Polym 2012, 87:1490-1494.
61. Abe M, Fukaya Y, Ohno H. Fast and facile dissolution of cellulose with tetrabutylphosphonium hydroxide containing 40 wt% water. Chem Commun 2001, 48:1808-1810.
62. Wei LG, Li KL, Ma YC, Hou X. Dissolving lignocellulosic biomass in a 1-butyl-3-methylimidazolium chloride-water mixture. Ind Crops and Prod 2012, 37:227-234.
63. Kilpelainen I, Xie H, King A, Granstrom M, Heikkinen S, Argyropoulos DS. Dissolution of wood in ionic liquids. J Agric Food Chem 2007, 55:9142-9148.
64. Zavrel M, Bross D, Funke M, Buchs J, Spiess AC. High-throughput screening for ionic liquids dissolving (ligno-)cellulose. Bioresour Technol 2009, 100:2580-2587.
65. Mora-Pale M, Meli L, Doherty TV, Linhardt RJ, Dordick JS. Room temperature ionic liquids as emerging solvents for the pretreatment of lignocellulosic biomass. Biotechnol Bioeng 2011, 108:1229-1245.
66. Sun N, Jiang XY, Maxim ML, Metlen A, Rogers RD. Use of polyoxometalate catalysts in ionic liquids to enhance the dissolution and delignification of woody biomass. ChemSusChem 2011, 4:65-73.
67. Muhammas N, Man Z, Khalil MAB. Ionic liquid-a future solvent for the enhanced uses of wood biomass. Eur J Wood Prod 2012, 70:123-133.
68. Xie H, Shi T. Liquefaction of wood (Metasequoia glyp-tostroboides) in allyl alkyl imidazolium ionic liquids. Wood Sci Technol 2009, 44:119-128.
69. Li B, Asikkala J, Filpponen I, Argyropoulos DS. Factors affecting wood dissolution and regeneration of ionic liquids. Ind Eng Chem Res 2010, 49:2477-2484.
70. Miyafuji H, Miyata K, Saka S. Reaction behavior of wood in an ionic liquid, 1-ethyl-3-methylimidazolium chloride. J Wood Sci 2009, 55:215-219.
71. Sun N, Rahman M, Qin Y, Maxim ML, Rodriguez RH, Rogers RD. Complete dissolution and partial delignification of wood in the ionic liquid 1-ethyl-3-methylimidazolium acetate. Green Chem 2009, 11:646-655.
72. Nakamura A, Miyafuji H, Saka S. Influence of reaction atmosphere on the liquefaction and depolymerization of wood in an ionic liquid, 1-ethyl-3-methylimidazolium chloride. J Wood Sci 2010, 56:256-261.
73. Zhao HB, Brown HM, Holladay JE, Zhang ZC. Prominent roles of impurities in ionic liquid for catalytic conversion of carbohydrates. Top Catal 2012, 55:33-37.
74. Morales-delaRosa S, Campos-Martin JM, Fierro JLG. High glucose yields from the hydrolysis of cellulose dissolved in ionic liquids. Chem Eng J 2012, 181-182:538-541.
75. Binder JB, Raines RT. Fermentable sugars by chemical hydrolysis of biomass. Proc Natl Acad Sci USA 2010, 107:4516-4521.
76. Rinaldi R, Palkovits R, Schüth F. Depolymerization of cellulose by solid catalysts in ionic liquids. Angew Chem Int Ed 2008, 120:8047-8050.
77. Dwiatmoko AA, Choi JW, Suh DJ, Suh Y-W, Kung HH. Understanding the role of halogen-containing ionic liquids in the hydrolysis of cellobiose catalyzed by acid resins. Appl Catal A Gen 2010, 387:209-214.
78. Cai HL, Li CZ, Wang AQ, Xu GL, Zhang T. Zeolite-promoted hydrolysis of cellulose in ionic liquid, insight into the mutual behavior of zeolite, cellulose and ionic liquid. Appl Catal B Environ 2012, 123-124:333-338.
79. Wang P, Yu HB, Zhan SH, Wang SQ. Catalytic hydrolysis of lignocellulosic biomass into 5-hydroxymethylfurfural in ionic liquid. Bioresour Technol 2011, 102:4179-4183.
80. Dutta S, De S, Alam MI, Abu-Omar MM, Saha B. Direct conversion of cellulose and lignocellulosic biomass into chemicals and biofuel with metal chloride catalysts. J Catal 2012, 288:8-15.
81. Tao F, Song H, Chou L. Efficient conversion of cellulose into furans catalyzed by metal ions in ionic liquids. J Mol Catal A Chem 2012, 357:11-18.
82. Ding Z-D, Chi Z, Gu W-X, Gu S-M, Liu J-H, Wang H-J. Theoretical and experimental investigation on dissolution and regeneration of cellulose in ionic liquid. Carbohydr Polym 2012, 89:7-16
83. Ignatyev IA, Van Doorslaer C, Mertens PGN, Binnemans K, De Vos DE. Reductive splitting of cellulose in the ionic liquid 1-butyl-3-methylimidazolium chloride. ChemSusChem 2010, 3:91-96.
84. Hu L, Sun Y, Lin L. Efficient conversion of glucose into 5-hydroxymethylfurfural by chromium(III) chloride in inexpensive ionic liquid. Ind Eng Chem Res 2012, 51:1099-1104.
85. Yong G, Zhang YG, Ying JY. Efficient catalytic system for the selective production of 5-hydroxymethylfurfural from glucose and fructose. Angew Chem Int Ed 2008, 47:9345-9348.
86. 2+ dimers. Angew Chem Int Ed 2010, 49:2530-2534.
87. 4 in an ionic liquid. Green Chem 2009, 11:1746-1749.
88. Cox BJ, Jia SY, Zhang ZC, Ekerdt JG. Catalytic degradation of lignin model compounds in acidic imidazolium based ionic liquids: Hammett acidity and anion effects. Polym Degradat Stability 2011, 96:426-431.
89. Jia SY, Cox BJ, Guo XW, Zhang ZC, Ekerdt JG. Decomposition of a phenolic lignin model compound over organic N-bases in an ionic liquid. Holzforschung 2010, 64:577-580.
90. Jia SY, Cox BJ, Guo XW, Zhang ZC, Ekerdt JG. Hydrolytic cleavage of beta-O-4 ether bonds of lignin model compounds in an ionic liquid with metal chlorides. Ind Eng Chem Res 2011, 50:849-855.
91. Stark K, Taccardi N, Bçsmann A, Wasserscheid P. Oxidative depolymerization of lignin in ionic liquids. ChemSusChem 2010, 3:719-723.
92. Zakzeski J, Jongerius AL, Weckhuysen BM. Transition metal catalyzed oxidation of alcell lignin, soda lignin, and lignin model compounds in ionic liquids. Green Chem 2010, 12:1225-1236.
93. Feng JG, Zhu QJ, Ma D, Liu XM, Han XW. Direct conversion and NMR observation of cellulose to glucose and 5-hydroxymethylfurfural (HMF) catalyzed by the acidic ionic liquids. J Mol Catal A Chem 2011, 334:8-12.
94. Yu HM, Hu J, Fan J, Chang J. One-pot conversion of sugars and lignin in ionic liquid and recycling of ionic liquid. Ind Eng Chem Res 2012, 51:3452-3457.
95. Xin Q, Pfeiffer K, Prausnitz JM, Clark DS, Blanch HW. Extraction of lignins from aqueous-ionic liquid mixtures by organic solvents. Biotechnol Bioeng 2012, 109:346-352.