Cleavage of Covalent Bonds in the Pyrolysis of Lignin, Cellulose, and Hemicellulose

Energy and Fuels

Volumn 29, Issue 9, 2015, Pages 5773-5780

  Liu, Muxin ^a,b,d   Yang, Jianli ^a   Liu, Zhenyu ^c   He, Wenjing ^c   Liu, Qingya ^c   Li, Yunmei ^a   Yang, Yong ^a,d  

^a INSTITUTE OF COAL CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^c BEIJING UNIVERSITY OF CHEMICAL TECHNOLOGY   (China)

^d SYNFUELS CHINA CO   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; ALUMINUM; CELLULOSE; COVALENT BONDS; LIGNIN;

9 ,10-DIHYDROPHENANTHRENE; CELLULOSE AND HEMICELLULOSE; HYDROGEN DONOR SOLVENT; STABLE RADICALS; UNIT STRUCTURE; WEAK BOND;

HYDROGEN BONDS;

EID: 84941931805     PISSN: 08870624     EISSN: 15205029     Source Type: Journal    
DOI: 10.1021/acs.energyfuels.5b00983     Document Type: Article

References (38)

1. Aburas, H.; Demirbas, A. Evaluation of beech for production of bio-char, bio-oil and gaseous materials Process Saf. Environ. Prot. 2015, 94, 29-36 10.1016/j.psep.2014.12.004
2. Luo, Z.; Wang, S.; Liao, Y.; Zhou, J.; Gu, Y.; Cen, K. Research on biomass fast pyrolysis for liquid fuel Biomass Bioenergy 2004, 26, 455-462 10.1016/j.biombioe.2003.04.001
3. Cao, J.; Xiao, X.; Zhang, S.; Zhao, X.; Sato, K.; Ogawa, Y.; Wei, X.; Takarada, T. Preparation and characterization of bio-oils from internally circulating fluidized-bed pyrolyses of municipal, livestock, and wood waste Bioresour. Technol. 2011, 102, 2009-2015 10.1016/j.biortech.2010.09.057
4. Drage, T. C.; Vane, C. H.; Abbott, G. D. The closed system pyrolysis of b-O-4 lignin substructure model compounds Org. Geochem. 2002, 33, 1523-1531 10.1016/S0146-6380(02)00119-5
5. Custodis, V. B. F.; Hemberger, P.; Ma, Z.; van Bokhoven, J. A. Mechanism of fast pyrolysis of lignin: studying model compounds J. Phys. Chem. B 2014, 118, 8524-8531 10.1021/jp5036579
6. Chu, S.; Subrahmanyam, A. V.; Huber, G. W. The pyrolysis chemistry of a β-O-4 type oligomeric lignin model compound Green Chem. 2013, 15, 125-136 10.1039/C2GC36332A
7. Lin, T.; Goos, E.; Riedel, U. A sectional approach for biomass: Modelling the pyrolysis of cellulose Fuel Process. Technol. 2013, 115, 246-253 10.1016/j.fuproc.2013.03.048
8. Liu, C.; Zhang, Y.; Huang, X. Study of guaiacol pyrolysis mechanism based on density function theory Fuel Process. Technol. 2014, 123, 159-165 10.1016/j.fuproc.2014.01.002
9. Zhang, M.; Geng, Z.; Yu, Y. Density functional theory (DFT) study on the dehydration of cellulose Energy Fuels 2011, 25, 2664-2670 10.1021/ef101619e
10. Bährle, C.; Custodis, V.; Jeschke, G.; van Bokhoven, J. A.; Vogel, F. In situ observation of radicals and molecular products during lignin pyrolysis ChemSusChem 2014, 7, 2022-2029 10.1002/cssc.201400079
11. Kim, K. H.; Bai, X.; Cady, S.; Gable, P.; Brown, R. C. Quantitative investigation of free radicals in bio-oil and their potential role in condensed-phase polymerization ChemSusChem 2015, 8, 894-900 10.1002/cssc.201403275
12. Zheng, S.; Feng, J.; Maciel, G. E. In situ high-temperature electron paramagnetic resonance (EPR) investigation of the charring of cellulose and cellulose/Na2CO3 mixtures and the O2-induced and H2O-induced behaviors of these chars Energy Fuels 2005, 19, 1201-1210 10.1021/ef040084n
13. Avni, E.; Suib, S. L.; Coughlin, R. W. Free radical formation in lignin during pyrolysis Holzforschung 1985, 39, 33-40 10.1515/hfsg.1985.39.1.33
14. Kibet, J.; Khachatryan, L.; Dellinger, B. Molecular products and radicals from pyrolysis of lignin Environ. Sci. Technol. 2012, 46, 12994-13001 10.1021/es302942c
15. Hedegaard, R. V.; Liu, L.; Skibsted, L. H. Quantification of radicals formed during heating of β-lactoglobulin with glucose in aqueous ethanol Food Chem. 2015, 167, 185-190 10.1016/j.foodchem.2014.06.118
16. Schulten, Z.; Schulten, K. The generation, diffusion, spin motion, and recombination of radical pairs in solution in the nanosecond time domain J. Chem. Phys. 1977, 66, 4616-4634 10.1063/1.433719
17. Fowler, T. G.; Bartle, K. D.; Kandiyoti, R. Limitations of electron spin resonance spectroscopy in assessing the role of free radicals in the thermal reactions of coal Energy Fuels 1989, 3, 515-522 10.1021/ef00016a015
18. He, W.; Liu, Q.; Shi, L.; Liu, Z.; Ci, D.; Lievens, C.; Guo, X.; Liu, M. Understanding the stability of pyrolysis tars from biomass in a view point of free radicals Bioresour. Technol. 2014, 156, 372-375 10.1016/j.biortech.2014.01.063
19. He, W.; Liu, Z.; Liu, Q.; Ci, D.; Lievens, C.; Guo, X. Behaviors of radical fragments in tar generated from pyrolysis of 4 coals Fuel 2014, 134, 375-380 10.1016/j.fuel.2014.05.064
20. Beauchet, R.; Pinard, L.; Kpogbemabou, D.; Laduranty, J.; Lemee, L.; Lemberton, J. L.; Bataille, F.; Magnoux, P.; Ambles, A.; Barbier, J. Hydroliquefaction of green wastes to produce fuels Bioresour. Technol. 2011, 102, 6200-6207 10.1016/j.biortech.2011.02.043
21. Vasilakos, N. P.; Austgen, D. M. Hydrogen-Donor Solvents in Biomass Liquefaction Ind. Eng. Chem. Process Des. Dev. 1985, 24, 304-311 10.1021/i200029a015
22. Zhang, J.; Chen, T.; Wu, J.; Wu, J. Multi-Gaussian-DAEM-reaction model for thermal decompositions of cellulose, hemicellulose and lignin: Comparison of N2 and CO2 atmosphere Bioresour. Technol. 2014, 166, 87-95 10.1016/j.biortech.2014.05.030
23. Kamiya, Y.; Nagae, S. Relative reactivity of hydrogen donor solvent in coal liquefaction Fuel 1985, 64, 1242-1245 10.1016/0016-2361(85)90182-6
24. Wu, W.; Mei, Y.; Zhang, L.; Liu, R.; Cai, J. Effective Activation Energies of Lignocellulosic Biomass Pyrolysis Energy Fuels 2014, 28, 3916-3923 10.1021/ef5005896
25. Pandey, M. P.; Kim, C. S. Lignin depolymerization and conversion: a review of thermochemical methods Chem. Eng. Technol. 2011, 34, 29-41 10.1002/ceat.201000270
26. Fernández-Costas, C.; Gouveia, S.; Sanromán, M. A.; Moldes, D. Structural characterization of Kraft lignins from different spent cooking liquors by 1D and 2D Nuclear Magnetic Resonance spectroscopy Biomass Bioenergy 2014, 63, 156-166 10.1016/j.biombioe.2014.02.020
27. Kim, H.; Ralph, J. Solution-state 2D NMR of ball-milled plant cell wall gels in DMSO-d6/pyridine-d5 Org. Biomol. Chem. 2010, 8, 576-591 10.1039/B916070A
28. Samuel, R.; Foston, M.; Jiang, N.; Allison, L.; Ragauskas, A. J. Structural changes in switchgrass lignin and hemicelluloses during pretreatments by NMR analysis Polym. Degrad. Stab. 2011, 96, 2002-2009 10.1016/j.polymdegradstab.2011.08.015
29. Luo, Y. Handbook of Bond Dissociation Energies in Organic Compounds; Science Press: Beijing, 2005; p 209.
30. Shi, L.; Liu, Q.; Guo, X.; Wu, W.; Liu, Z. Pyrolysis behavior and bonding information of coal - A TGA study Fuel Process. Technol. 2013, 108, 125-132 10.1016/j.fuproc.2012.06.023
31. Brebu, M.; Vasile, C. Thermal degradation of lignin-A review Cellul. Chem. Technol. 2010, 44, 353-363
32. Younker, J. M.; Beste, A.; Buchanan, A. C., III Computational study of bond dissociation enthalpies for substituted β-O-4 lignin model compounds ChemPhysChem 2011, 12, 3556-3565 10.1002/cphc.201100477
33. Kim, S.; Chmely, S. C.; Nimlos, M. R.; Bomble, Y. J.; Foust, T. D.; Paton, R. S.; Beckham, G. T. Computational study of bond dissociation enthalpies for a large range of native and modified lignins J. Phys. Chem. Lett. 2011, 2, 2846-2852 10.1021/jz201182w
34. Shen, D. K.; Gu, S.; Bridgwater, A. V. The thermal performance of the polysaccharides extracted from hardwood: Cellulose and hemicellulose Carbohydr. Polym. 2010, 82, 39-45 10.1016/j.carbpol.2010.04.018
35. Wrigstedt, P.; Kylli, P.; Pitkänen, L.; Nousiainen, P.; Tenkanen, M.; Sipilä, J. Synthesis and antioxidant activity of hydroxycinnamic acid xylan esters J. Agric. Food Chem. 2010, 58, 6937-6943 10.1021/jf9043953
36. Geng, Z. Theoretical and Experimental Study on Mechanism of Cellulose Pyrolysis. Doctoral Dissertation, Tianjin University, Tianjin, China, 2010.
37. Wang, Z.; McDonald, A. G.; Westerhof, R. J. M.; Kersten, S. R. A.; Cuba-Torres, C. M.; Ha, S.; Pecha, B.; Garcia-Perez, M. Effect of cellulose crystallinity on the formation of a liquid intermediate and on product distribution during pyrolysis J. Anal. Appl. Pyrolysis 2013, 100, 56-66 10.1016/j.jaap.2012.11.017
38. Zhang, X.; Yang, W.; Blasiak, W. Thermal decomposition mechanism of levoglucosan during cellulose pyrolysis J. Anal. Appl. Pyrolysis 2012, 96, 110-119 10.1016/j.jaap.2012.03.012