Structural elucidation of sorghum lignins from an integrated biorefinery process based on hydrothermal and alkaline treatments

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 32, 2014, Pages 8120-8128

  Sun, Shao Long ^a   Wen, Jia Long ^a   Ma, Ming Guo ^a   Sun, Run Cang ^a,b  

^a BEIJING FORESTRY UNIVERSITY   (China)

^b SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

alkaline treatment; hydrothermal pretreatment; lignin; nuclear magnetic resonance (NMR); structural feature; sweet sorghum stem

Indexed keywords

CONDENSATION REACTIONS; DELIGNIFICATION; REFINING; SUBSTRATES; NUCLEAR MAGNETIC RESONANCE;

ALKALINE TREATMENT; HYDROTHERMAL PRETREATMENT; NUCLEAR MAGNETIC RESONANCE(NMR); STRUCTURAL FEATURE; SWEET SORGHUM STEMS;

LIGNIN;

CONDENSATION; DELIGNIFICATION; LIGNINS; NUCLEAR MAGNETIC RESONANCE; REFINING; SUBSTRATES; SORGHUM; STEMS;

BIOFUEL; CAUSTIC AGENT; LIGNIN; SODIUM HYDROXIDE; WATER VAPOR;

CHEMICAL STRUCTURE; CHEMISTRY; CHINA; COMPARATIVE STUDY; CROP; ECONOMICS; ENERGY CONSERVATION; HEAT; HYDROLYSIS; ISOLATION AND PURIFICATION; KINETICS; MOLECULAR WEIGHT; PLANT STEM; SORGHUM; WATER VAPOR;

BIOFUELS; CAUSTICS; CHINA; CONSERVATION OF ENERGY RESOURCES; CROPS, AGRICULTURAL; HOT TEMPERATURE; HYDROLYSIS; KINETICS; LIGNIN; MOLECULAR STRUCTURE; MOLECULAR WEIGHT; PLANT STEMS; SODIUM HYDROXIDE; SORGHUM; STEAM;

EID: 84906218568     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf501669r     Document Type: Article

References (43)

1. Ragauskas, A. J.; Beckham, G. T.; Biddy, M. J.; Chandra, R.; Chen, F.; Davis, M. F. Lignin valorization: improving lignin processing in the biorefinery. Science 2014, 344, DOI: 10.1126/science.1246843.
2. Liu, S.; Lu, H.; Hu, R.; Shupe, A.; Lin, L.; Liang, B. A sustainable woody biomass biorefinery Biotechnol. Adv. 2012, 30, 785-810
3. Alfani, F.; Gallifuoco, A.; Saporosi, A.; Spera, A.; Cantarella, M. J. Comparison of SHF and SSF processes for the bioconversion of steam-exploded wheat straw J. Ind. Microbiol. Biotechnol. 2000, 25, 184-192
4. Liu, C.; van der Heide, E.; Wang, H.; Li, B.; Yu, G.; Mu, X. Alkaline twin-screw extrusion pretreatment for fermentable sugar production Biotechnol. Biofuels 2013, 6, 97
5. Ishizawa, C. I.; Davis, M. F.; Schell, D. F.; Johnson, D. K. Porosity and its effect on the digestibility of dilute sulfuric acid pretreated corn stover J. Agric. Food Chem. 2007, 55, 2575-2581
6. Karagöz, S.; Bhaskar, T.; Muto, A.; Sakata, Y. Comparative studies of oil compositions produced from sawdust, rice husk, lignin and cellulose by hydrothermal treatment Fuel 2005, 84, 875-884
7. Walch, E.; Zemann, A.; Schinner, F.; Bonn, G.; Bobleter, O. Enzymatic saccharification of hemicellulose obtained from hydrothermally pretreated sugar cane bagasse and beech bark Bioresour. Technol. 1992, 39, 173-177
8. Cybulska, I.; Lei, H.; Julson, J. Hydrothermal pretreatment and enzymatic hydrolysis of prairie cord grass Energy Fuels 2009, 24, 718-727
9. Pronyk, C.; Mazza, G.; Tamaki, Y. Production of carbohydrates, lignins, and minor components from triticale straw by hydrothermal treatment J. Agric. Food Chem. 2011, 59, 3788-3796
10. Prakasham, R. S.; Nagaiah, D.; Vinutha, K. S.; Uma, A.; Chiranjeevi, T.; Umakanth, A. V. Sorghum biomass: a novel renewable carbon source for industrial bioproducts Biofuels 2014, 5, 159-174
11. Lu, H.; Hu, R.; Ward, A.; Amidon, T. E.; Liang, B.; Liu, S. Hot-water extraction and its effect on soda pulping of aspen woodchips Biomass Bioenergy 2012, 39, 5-13
12. 4-catalyzed hydrothermal pretreatment of rapeseed straw for bioconversion to ethanol: focusing on pretreatment at high solids content Bioresour. Technol. 2009, 100, 3048-3053
13. Gould, J. M. Alkaline peroxide delignification of agricultural residues to enhance enzymatic saccharification Biotechnol. Bioeng. 1984, 26, 46-52
14. Dang, V. Q.; Nguyen, K. L. A universal kinetic equation for characterising the fractal nature of delignification of lignocellulosic materials Cellulose 2007, 14, 153-160
15. Kaparaju, P.; Felby, C. Characterization of lignin during oxidative and hydrothermal pre-treatment processes of wheat straw and corn stover Bioresour. Technol. 2010, 101, 3175-3181
16. Doherty, W. O.; Mousavioun, P.; Fellows, C. M. Value-adding to cellulosic ethanol: lignin polymers Ind. Crops Prod. 2011, 33, 259-276
17. Zhao, J.; Wilkins, R. M. Controlled release of the herbicide, fluometuron, from matrix granules based on fractionated organosolv lignins J. Agric. Food Chem. 2003, 51, 4023-4028
18. Zhang, X.; Tu, M.; Paice, M. G. Routes to potential bioproducts from lignocellulosic biomass lignin and hemicelluloses Bioenergy Res. 2011, 4, 246-257
19. Sluiter, A.; Hames, B.; Ruiz, R.; Scarlata, C.; Sluiter, J.; Templeton, D.; Crocker, D. Determination of Structural Carbohydrates and Lignin in Biomass; Technical Report NREL/TP-510-42618; National Renewable Energy Laboratory: Golden, CO, USA, 2008.
20. Sun, S. L.; Wen, J. L.; Ma, M. G.; Li, M. F.; Sun, R. C. Revealing the structural inhomogeneity of lignins from sweet sorghum stem by successive alkali extractions J. Agric. Food Chem. 2013, 61, 4226-4235
21. Granata, A.; Argyropoulos, D. S. 2-Chloro-4,4,5,5-tetramethyl-1,3,2- dioxaphospholane, a reagent for the accurate determination of the uncondensed and condensed phenolic moieties in lignins J. Agric. Food Chem. 1995, 43, 1538-1544
22. Wen, J. L.; Sun, S. L.; Yuan, T. Q.; Xu, F.; Sun, R. C. Structural elucidation of lignin polymers of eucalyptus chips during organosolv pretreatment and extended delignification J. Agric. Food Chem. 2013, 61, 11067-11075
23. Samuel, R.; Cao, S.; Das, B. K.; Hu, F.; Pu, Y.; Ragauskas, A. J. Investigation of the fate of poplar lignin during autohydrolysis pretreatment to understand the biomass recalcitrance RSC Adv. 2013, 3, 5305-5309
24. Sannigrahi, P.; Kim, D.-H.; Jung, S.; Ragauskas, A. Pseudo-lignin and pretreatment chemistry Energy Environ. Sci. 2011, 4, 1306-1310
25. Leschinsky, M.; Zuckerstätter, G.; Weber, H. K.; Patt, R.; Sixta, H. Effect of autohydrolysis of Eucalyptus globulus wood on lignin structure. Part 1: comparison of different lignin fractions formed during water prehydrolysis Holzforschung 2008, 62, 645-652
26. Wen, J. L.; Xue, B. L.; Xu, F.; Sun, R. C.; Pinkert, A. Unmasking the structural features and property of lignin from bamboo Ind. Crops Prod. 2013, 42, 332-343
27. Faix, O. Classification of lignins from different botanical origins by FT-IR spectroscopy Holzforschung 1991, 45, 21-28
28. Sun, S. L.; Wen, J. L.; Ma, M. G.; Sun, R. C.; Jones, G. L. Structural features and antioxidant activities of degraded lignins from steam exploded bamboo stem Ind. Crops Prod. 2014, 56, 128-136
29. Wen, J. L.; Sun, S. N.; Yuan, T. Q.; Xu, F.; Sun, R. C. Fractionation of bamboo culms by autohydrolysis, organosolv delignification and extended delignification: understanding the fundamental chemistry of the lignin during the integrated process Bioresour. Technol. 2013, 150, 278-286
30. Del Río, J. C.; Rencoret, J.; Prinsen, P.; Martínez, A. N. T.; Ralph, J.; Gutiérrez, A. Structural characterization of wheat straw lignin as revealed by analytical pyrolysis, 2D-NMR, and reductive cleavage methods J. Agric. Food Chem. 2012, 60, 5922-5935
31. Martínez, á. T.; Rencoret, J.; Marques, G.; Gutiérrez, A.; Ibarra, D.; Jiménez-Barbero, J.; Del Río, J. C. Monolignol acylation and lignin structure in some nonwoody plants: a 2D NMR study Phytochemistry 2008, 69, 2831-2843
32. Ralph, J.; Lundquist, K.; Brunow, G.; Lu, F.; Kim, H.; Schatz, P. F. Lignins: natural polymers from oxidative coupling of 4-hydroxyphenyl-propanoids Phytochem. Rev. 2004, 3, 29-60
33. Sun, S. N.; Cao, X. F.; Xu, F.; Sun, R. C.; Jones, G. L. Structural features and antioxidant activities of lignins from steam exploded bamboo (Phyllostachys pubescens) J. Agric. Food Chem. 2014, 62, 5939-5947
34. Wen, J. L.; Sun, S. L.; Xue, B. L.; Sun, R. C. Recent advances in characterization of lignin polymer by solution-state nuclear magnetic resonance (NMR) methodology Materials 2013, 6, 359-391
35. Wen, J. L.; Xue, B. L.; Xu, F.; Sun, R. C. Quantitative structural characterization of the lignins from the stem and pith of bamboo (Phyllostachys pubescens) Holzforschung 2013, 67, 613-627
36. Wen, J. L.; Sun, S. L.; Xue, B. L.; Sun, R. C. Quantitative structures and thermal properties of birch lignins after ionic liquid pretreatment J. Agric. Food Chem. 2013, 61, 635-645
37. Sette, M.; Wechselberger, R.; Crestini, C. Elucidation of lignin structure by quantitative 2D NMR Chem.-Eur. J. 2011, 17, 9529-9535
38. El Hage, R.; Chrusciel, L.; Desharnais, L.; Brosse, N. Effect of autohydrolysis of Miscanthus × giganteus on lignin structure and organosolv delignification Bioresour. Technol. 2010, 101, 9321-9329
39. 31P NMR in biomass lignin and biofuel precursors characterization J. Energy Environ. Sci. 2011, 4, 3154-3166
40. 31P and 2D NMR spectroscopy. The occurrence of ester bonds and α- O -4 substructures J. Agric. Food Chem. 1997, 45, 1212-1219
41. Hodgson, E.; Nowakowski, D.; Shield, I.; Riche, A.; Bridgwater, A. V.; Clifton-Brown, J. C. Variation in Miscanthus chemical composition and implications for conversion by pyrolysis and thermo-chemical bio-refining for fuels and chemicals Bioresour. Technol. 2011, 102, 3411-3418
42. Sun, R. C.; Tomkinson, J.; Jones, G. J. Fractional characterization of ash-AQ lignin by successive extraction with organic solvents from oil palm EFB fibre Polym. Degrad. Stab. 2000, 68, 111-119
43. Raveendran, K.; Ganesh, A.; Khilar, K. C. Influence of mineral matter on biomass pyrolysis characteristics Fuel 1995, 74, 1812-1822