Promises in direct conversion of cellulose and lignocellulosic biomass to chemicals and fuels: Combined solvent-nanocatalysis approach for biorefinary

Biomass and Bioenergy

Volumn 62, Issue , 2014, Pages 182-197

  Dutta, Saikat ^a   Pal, Sharmistha ^b  

^a INSTITUTE OF NANO SCIENCE AND TECHNOLOGY   (India)

^b ICAR INDIAN INSTITUTE OF SOIL AND WATER CONSERVATION   (India)

Author keywords

Biofuel; Biorefinery; Cellulose; Furanics; Isosorbide; Valerolactone

Indexed keywords

5 HYDROXYMETHYL FURFURALS; BIOREFINERIES; FUNCTIONALIZED NANOPARTICLES; FURANICS; ISOSORBIDE; LIGNOCELLULOSE CONVERSIONS; LIGNOCELLULOSIC BIOMASS; VALEROLACTONE;

BIOFUELS; DISTILLATION; FATTY ACIDS; IONIC LIQUIDS; LIQUID FUELS; LOCAL AREA NETWORKS; MESOPOROUS MATERIALS; ORGANIC ACIDS; SURVEYS;

CELLULOSE;

BIOFUEL; BIOMASS POWER; BIOTECHNOLOGY; CATALYSIS; CATALYST; CELLULOSE; CRYSTALLINITY; DISTILLATION; ENVIRONMENTAL ISSUE; ESTER; LIGNIN; REFINING INDUSTRY; SOLVENT; SUSTAINABILITY; TRANSFORMATION;

EID: 84896732296     PISSN: 09619534     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.biombioe.2013.12.019     Document Type: Review

References (98)

1. Nel W.P., Cooper C.J. Implications of fossil fuel constraints on economic growth and global warming. Energy Policy 2009, 37:166-180.
2. Shafiee S., Topal E. When will fossil fuel reserves be finished. Energy Policy 2009, 37:181-189.
3. Gandini A., Silvestre A.J.D., Neto C.P., Sousa A.F., Gomes M. The furan counterpart of poly (ethylene terephthalate): an alternative material based on renewable resources. J Polym Sci A Polym Chem 2009, 47:295-298.
4. Binder J.B., Cefali A.V., Blank J.J., Raines R.T. Synthesis of furfural from xylose and xylan. Energy Environ Sci 2010, 3:765-771.
5. Román-Leshkov Y., Chheda J.N., Dumesic J.A. Phase modifiers promote efficient production of hydroxymethylfurfural from fructose. Science 2006, 213:1933-1937.
6. Chheda J.N., Huber G.W., Dumesic J.A. Water-tolerant Mesoporous-carbon-supported ruthenium catalysts for the hydrolysis of cellulose to glucose. Angew Chem Int Ed 2007, 46:7164-7183.
7. Saha B., Dutta S., Abu-Omar M.-M. Aerobic oxidation of 5-hydroxylmethylfurfural with homogeneous and nanoparticulate catalysts. Catal Sci Technol 2012, 2:79-81.
8. Pasini T., Piccinini M., Blosi M., Bonelli R., Albonetti S., Dimitratos N., et al. Selective oxidation of 5-hydroxymethyl-2-furfural using supported gold-copper nanoparticles. Green Chem 2011, 13:2091-2099.
9. Zhong S., Daniel R., Xu H., Zhang J., Turner D., Wyszynski M.L., et al. Combustion and emissions of 2, 5-dimethylfuran in a direct-injection spark-ignition engine. Energy Fuels 2010, 24:2891-2899.
10. Tian G., Daniel R., Li H., Xu H., Shuai S., Richards P. Laminar burning velocities of 2,5-dimethylfuran compared with ethanol and gasoline. Energy Fuels 2010, 24:3898-3905.
11. Rinaldi R., Schüth F. Acid hydrolysis of cellulose as the entry point into biorefinery schemes. ChemSusChem 2009, 2:1096-1107.
12. Geilen F.M.A., Engendahl B., Harwardt A., Marquardt W., Klankermayer J., Leitner W. Selective and flexible transformation of biomass-derived platform chemicals by a multifunctional catalytic system. Angew Chem Int Ed 2010, 49:5510-5514.
13. Somerville C., Youngs H., Taylor C., Davis S.C., Long S.P. Feedstocks for lignocellulosic biofuels. Science 2010, 329:790-792.
14. Taarning E., Osmundsen C.M., Yang X.B., Voss B., Andersen S.I., Christensen C.H. Zeolite-catalyzed biomass conversion to fuels and chemicals. Energy Environ Sci 2011, 4:793-804.
15. Loerbroks C., Rinaldi R., Thiel W. The electronic nature of the 1,4-β-glycosidic bond and its chemical environment: DFT insights into cellulose chemistry. Chem Eur J 2013, 10.1002/chem.201301366.
16. Meine N., Rinaldi R., Schüth F. Solvent-free catalytic depolymerization of cellulose to water-soluble oligosaccharides. ChemSusChem 2012, 5:1449-1454.
17. Klemm D., Heublein B., Fink H., Bohn A. Cellulose conversion into polyols catalyzed by reversibly formed acids and supported ruthenium clusters in hot water. Angew Chem Int Ed 2005, 44:3358-3393.
18. Nishiyama Y., Sugiyama J., Chanzy H., Langan P. Crystal structure and hydrogen bonding system in cellulose from synchrotron X-ray and neutron fiber diffraction. J Am Chem Soc 2003, 125:14300-14306.
19. Mohan D., Pittman C.U., Steele P.H. Pyrolysis of wood/biomass for bio-oil: a critical review. Energy Fuels 2006, 20:848-889.
20. Eichhorn S.J. Cellulose nanowhiskers: promising materials for advanced applications. Soft Mat 2011, 7:303-315.
21. Danner H., Braun R. Biotechnology for the production of commodity chemicals from biomass. Chem Soc Rev 1999, 28:395-405.
22. Bozell J.J., Petersen G.R. Technology development for the production of biobased products from biorefinery carbohydrates-the US department of energy's "top 10" revisited. Green Chem 2010, 12:539-544.
23. Kwon K.C., Mayfield H., Marolla T., Nichols B., Mashburn M. Catalytic deoxygenation of liquid biomass for hydrocarbon fuels. Renew Energy 2011, 36:907-915.
24. Zhang Y.P., Lynd L.R. Catalytic conversion of cellulose into sugar alcohols. Biotechnol Bioeng 2004, 88:797-824.
25. Bharadwaj R., Wong A., Knierim B., Singh Holmes B.M., Auer M., Simmons B.A., et al. High-throughput enzymatic hydrolysis of lignocellulosic biomass via in-situ regeneration. Biores Tech 2011, 102:1329-1337.
26. Stöcker M. Biofuels and biomass-to-liquid fuels in the biorefinery: catalytic conversion of lignocellulosic biomass using porous materials. Angew Chem Int Ed 2008, 47:9200-9211.
27. Zhou C.-H., Xia X., Lin C.-X., Tong D.-S., Beltramini J. Hydrogenolysis of lignosulfonate into phenols over heterogeneous nickel catalysts. Chem Soc Rev 2011, 40:5588-5617.
28. Gallezot P. Conversion of biomass to selected chemical products. Chem Soc Rev 2012, 41:1538-1558.
29. Dutta S. Catalytic materials that improve selectivity of biomass conversions. RSC Adv 2012, 2:12575-12593.
30. De Vyver S.V., Geboers J., Jacobs P.A., Sels B.F. Recent advances in the catalytic conversion of cellulose. ChemCatChem 2011, 3:82-94.
31. Zhao H., Holladay J.E., Brown H., Zhang Z.C. Metal chlorides in ionic liquid solvents convert sugars to 5-hydroxymethylfurfural. Science 2007, 316:1597-1600.
32. Binder J.B., Raines R.T. Simple chemical transformation of lignocellulosic biomass into furans for fuels and chemicals. J Am Chem Soc 2009, 131:1979-1985.
33. Dee S.J., Bell A. Study of the acid-catalyzed hydrolysis of cellulose dissolved in ionic liquids and the factors influencing the dehydration of glucose and the formation of humins. ChemSusChem 2011, 4:1166-1173.
34. Kono T., Matsuhisa H., Maehara H., Horie H., Matsuda K. Chemical transformation of lignocellulosic biomass into fuels and chemicals. Jpn Pat Appl 2005, 2005232116.
35. Su Y., Brown H.M., Huang X., Zhou X.D., Amonette J.E., Zhang Z.C. Single-step conversion of cellulose to 5-hydroxymethylfurfural (HMF), a versatile platform chemical. Appl Catal A Gen 2009, 361:117-122.
36. Zhang Y., Du H., Qian X., Chen E.-Y.-X. Ionic liquid-water mixtures: enhanced Kw for efficient cellulosic biomass conversion. Energy Fuels 2010, 24:2410-2417.
37. Li C., Zhang Z., Zhao Z.K. Direct conversion of glucose and cellulose to 5-hydroxymethylfurfural in ionic liquid under microwave irradiation. Tetrahedron Lett 2009, 50:5403-5405.
38. Qi X., Watanabe M., Aida T.M., Smith R.L. Fast transformation of glucose and di-/polysaccharides into 5-hydroxymethylfurfural by microwave heating in an ionic liquid/catalyst system. ChemSusChem 2010, 3:1071-1077.
39. Kim Z., Jeong J., Lee D., Sangyong K., Yoon H.-J., Lee Y.-S., et al. Direct transformation of cellulose into 5-hydroxymethyl-2-furfuralusing a combination of metal chlorides in imidazolium ionic liquid. Green Chem 2011, 13:1503-1506.
40. Wang P., Yu H., Zhan S., Wang S. Catalytic hydrolysis of lignocellulosic biomass into 5-hydroxymethylfurfural in ionic liquid. Biores Tech 2011, 102:4179-4183.
41. Tao F., Song H., Chou L. Catalytic conversion of cellulose to chemicals in ionic liquid. Carbohydr Res 2011, 346:58-63.
42. Tao F., Song H., Yang J., Chou L. Degradation and conversion of cellulose in ionic liquids. Carbohydr Polym 2011, 85:363-368.
43. Jiang F., Zhu Q., Ma D., Liu X., Han X. 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.
44. Tan M., Zhao L., Zhang Y. Production of 5-hydroxymethyl furfural from cellulose in CrCl2/Zeolite/BMIMCl system. Biomass Bioenergy 2011, 35:1367-1370.
45. Gen Y., Zhang Y.G., Ying J.Y. Efficient catalytic system for the selective production of 5-hydroxymethylfurfural from glucose and fructose. Angew Chem Int Ed 2008, 47:9345-9348.
46. Mascal M., Niktin E.B. High-yield conversion of plant biomass into the key value added feedstocks 5-(hydroxymethyl)furfural, levulinic acid, and levulinic esters via 5-(chloromethyl)furfural. Green Chem 2010, 12:370-373.
47. Hick S.M., Griebel C., Restrepo D.T., Truitt J.H., Buker E.J., Bylda C., et al. Mechanocatalysis for biomass-derived chemicals and fuels. Green Chem 2010, 12:468-474.
48. Peng W.-H., Lee Y.-Y., Wu C., Wu K.C.W. Acid-base bi-functionalized, large-pored mesoporous silica nanoparticles for cooperative catalysis of one-pot cellulose-to-HMF conversion. J Math Chem 2012, 22:23181-23185.
49. Caes B.R., Palte M.J., Raines R.T. Orgaocatalytic conversion of cellulose into a platform chemical. Chem Sci 2013, 4:196-199.
50. Van de Vyver S., Thomas J., Geboers J., Keyzer S., Smet M., Dehaen W., et al. Catalytic production of levulinic acid from cellulose and other biomass-derived carbohydrates with sulfonated hyperbranched poly(arylene oxindole)s. Energy Environ Sci 2011, 4:3601-3610.
51. Zhao S., Cheng M., Li J., Tian J., Wang X. One pot production of 5-hydroxymethylfurfural with high yield from cellulose by a Brønsted-Lewis-surfactant-combined heteropolyacid catalyst. Chem Commun 2011, 47:2176-2178.
52. Tian C., Bao C., Binder A., Zhu Z., Hu B., Guo Y., et al. An efficient and reusuable "hairy" particle acid catalyst for the synthesis of 5-hydroxymethylfurfural from dehydration of fructose in water. Chem Commun 2013, 49:8668-8670.
53. Shi N., Liu Q., Zhang Q., Wang T., Ma L. High yield production of 5-hydroxymethylfurfural from cellulose by high concentration of sulfates in biphasic system. Green Chem 2013, 15:1967-1974.
54. De S., Dutta S., Saha B. Microwave assisted conversion of carbohydrates and biopolymers to 5-hydroxymethylfurfural with aluminum chloride catalyst in water. Green Chem 2011, 13:2859-2868.
55. Alonso D.M., Wettstein S.G., Bond J.Q., Root T.W., Dumesic J.A. Production of biofuels from cellulose and corn stover using alkylphenol solvents. ChemSusChem 2011, 4:1078-1081.
56. Sievers C., Musin I., Marzialetti T., Olarte M.B.V., Agrawal P.K., Jones C.W. Acid-catalyzed conversion of sugars and furfurals in an ionic-liquid phase. ChemSusChem 2009, 2:665-671.
57. Kumar P., Barrett D.M., Delwiche M.J., Stroeve P. Methods for pretreatment of lignocellulosic biomass for efficient hydrolysis and biofuel production. Ind Eng Chem Res 2009, 48:3713-3729.
58. Carrasquillo-Flores R., Kaldstrom M., Schuth F., Dumesic J.A., Rinaldi R. Mechanocatalytic depolymerization of dry (lingo)cellulose as an entry process for high-yield production of furfurals. ACS Catal 2013, 3:993-997.
59. Fan J., De bruyn M., Budarin V.L., Gronnow M.J., Shuttleworth P.S., Breeden S., et al. Direct microwave-assisted hydrothermal depolymerization of cellulose. J Am Chem Soc 2013, 135:11728-11731.
60. Rose M., Palkovits R. Isosorbide as a renewable platform chemical for versatile applications-Quo vadis. ChemSusChem 2012, 5:167-176.
61. Lub J., Nijssen W.P.M., Wegh R.T., Vogels J.P.A., Ferrer A. Synthesis and properties of photoisomerizable derivatives of isosorbide and their use in cholesteric filters. Adv Funct Mater 2005, 15:1961-1972.
62. Van Buu O.N., Aupoix A., VoThanh G. Synthesis of novel chiral imidazolium-based ionic liquids derived from isosorbide and their applications in asymmetric aza Diels-Alder reaction. Tetrahedron 2009, 65:2260-2265.
63. Fenouillot F., Rousseau A., Colomines G., Saint-Loup S., Pascault J.P. Sugar-based chemicals for environmentally sustainable applications. Prog Polym Sci 2010, 35:578-622.
64. Stoss P., Hemmer R. 1,4:3,6-dianhydrohexitols. Adv Carbohydr Chem Biochem 1991, 49:93-173.
65. Fléche G., Huchette M. Isosorbide. preparation, properties and chemistry. Starch/Staerke 1986, 38:26-30.
66. Wu J., Eduard P., Thiyagarajan J.V., Haveren D.S., Van Es C.E., Koning M., et al. Isohexide derivatives from renewable resources as chiral building blocks. ChemSusChem 2011, 4:599-603.
67. Almeida RM, Rene C, Rabello K. Diesel cycle fuel compositions containing dianhydrohexitols and related products. US Pat 2010, 0064574 A1,12/538, 451.
68. (accessed September 2013). http://www.roquette.com.
69. (accessed September 2013). http://www.icis.com.
70. DeAlmeida R.M., Li J., Nederlof C., O'Connor P., Makkee M., Moulijn J.A. Cellulose conversion to isosorbide in molten salt hydrate media. ChemSusChem 2010, 3:325-328.
71. Fischer S., Leipner H., Thümmler K., Brendler E., Peters J. Molten inorganic salts as reaction medium for cellulose. Cellulose 2003, 10:227-236.
72. 3: identification of reaction intermediates. J Catal 2010, 270:48-59.
73. Yamaguchi A., Hiyoshi N., Sato O., Shirai M. Sorbitol dehydration in high temperature liquid water. Green Chem 2011, 13:873-881.
74. Liang G., Wu C., He L., Ming J., Cheng H., Zhuo L., et al. Selective conversion of concentrated microcrystalline cellulose to isosorbide over Ru/C catalyst. Green Chem 2011, 13:839-842.
75. Sun P., Long X., He H., Xia C., Li F. Conversion of cellulose into isosorbide over bifunctional ruthenium nanoparticles supported on niobium phosphate. ChemSusChem 2013, 10.1002/cssc.201300701.
76. De Beek B.O., Geboers J., De Vyver S.V., Lishout J.V., Snelders J., Huijgen W.J.J., et al. Conversion of (ligno)cellulose feeds to isosorbide with heteropoly acids and Ru on carbon. ChemSusChem 2013, 6:199-208.
77. Ragauskas A.J., Williams C.K., Davidson B.H., Britovsek G., Cairney J., Eckert C.A., et al. The path forward for biofuels and biomaterials. Science 2006, 311:484-489.
78. Román-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.
79. Barlow M.T., Smith D.J., Steward D.G. 2,5-dimethylfuran in a direct-injection spark-ignition engine. Eur Pat 1983, EP0082689.
80. De S., Dutta S., Saha B. One-pot conversions of lignocellulosic and algal biomass into liquid fuels. ChemSusChem 2012, 5:1826-1833.
81. Yang W., Sen A. One-step catalytic transformation of carbohydrates and cellulosic biomass to 2,5-dimethyltetrahydrofuran for liquid fuels. ChemSusChem 2010, 3:597-603.
82. Sen AS, Yang W. One-step catalytic conversion of biomass-derived carbohydrates to liquid fuels. US Pat 2010, 8440870 B2,12/455, 816.
83. Mascal M., Nikitin E.B. Direct, high-yield conversion of cellulose into biofuel. Angew Chem Int Ed 2008, 47:7924-7926.
84. Gruter G.J.M., Dautzenberg F. Dramatic advancements. Eur Pat Appl 2007, 1834950A1.
85. Avantium Technologies press release: http://www.avantium.com/index.php?p=115%26n=2.
86. Mascal M., Nikitin E.B. Dramatic advancements in the saccharide to 5-(chloromethyl)furfural conversion reaction. ChemSusChem 2009, 2:859-861.
87. Dutta S., De S., Alam M.I., Abu-Omar M.M., Saha B. Direct conversion of cellulose and lignocellulosic biomass into chemicals and biofuel with metal chloride catalysts. J Catal 2012, 288:8-15.
88. Kim B., Jeong J., Shin S., Lee D., Kim S., Yoon H.-Y., et al. Facile single-step conversion of macroalgal polymeric carbohydrates into biofuels. ChemSusChem 2010, 3:1273-1275.
89. Gürbüz E.I., Alonso D.M., Bond J.Q., Dumesic J.A. Reactive extraction of levulinate esters and conversion to γ-valerolactone for production of liquid fuels. ChemSusChem 2011, 4:357-361.
90. Horváth I.T., Mehdi H., Fábos V., Boda L., Mika L.T. γ-Valerolactone-a sustainable liquid for energy and carbon-based chemicals. Green Chem 2008, 10:238-242.
91. Bozell J.J. Connecting biomass and petroleum processing with a chemical bridge. Science 2010, 329:522-523.
92. Lange J.-P., Price R., Ayoub P.M., Louis J., Petrus L., Clarke L., et al. Valeric biofuels: a platform of cellulosic transportation fuels. Angew Chem Int Ed 2010, 49:4479-44483.
93. Palkovits R. Pentenoic acid pathways for cellulosic biofuels. Angew Chem Int Ed 2010, 49:4336-4338.
94. 2 supply. Angew Chem Int Ed 2009, 48:6529-6532.
95. Bond J.Q., Alonso D.M., Wang D., West R.M., Dumesic J.A. Integrated catalytic conversion of γ-valerolactone to liquid alkenes for transportation fuels. Science 2010, 327:1110-1114.
96. Yuan J., Li S.-S., Liu Y.-M., Cao Y., He H.-Y., Fan K.-N. Copper-based catalysts for the efficient conversion of carbohydrate biomass into γ-valerolactone in the absence of externally added hydrogen. Energy Environ Sci 2013, 6:3308-3313.
97. 2 nanospheres via aspartic acid templating pathway and its catalytic application for 5-hydroxymethyl-furfural synthesis. J Math Chem 2011, 21:17505-17510.
98. 2 nanoparticles. Appl Catal A Gen 2011, 409/410:133-139.