纤维素典型热解产物生成机理研究进展

doi:10.3969/j.issn.1673-5854.2019.05.010

Abstract

Abstract:

It received increasing attentions to adopt the pyrolysis of biomass to produce liquid fuels and value-added chemicals. Study of the pyrolysis mechanism of biomass individual components could provide a better understanding of the biomass pyrolysis and was helpful for the regulation of the pyrolysis process. In this paper, the mechanisms of the cellulose pyrolysis and some typical products formation pathway were reviewed. And that further research should choose the representative model compounds was pointed out and the cellulose pyrolysis mechanism under different kinds of catalysts should be investigated.

Key words: cellulose, levoglucosan, levoglucosenone, 5-HMF, isotopic labeling

CLC Number:

TQ35
TK6

Zixiang GAO,Shengnan ZHANG,Weiming YI. Research Progress in Formation Mechanism of Typical Pyrolysis Products of Cellulose[J]. Biomass Chemical Engineering, 2019, 53(5): 57-66.

Figures/Tables 6

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References 63

1	BAHNG M , MUKARAKATE C , ROBICHAUD D J , et al. Current technologies for analysis of biomass thermochemical processing:A review[J]. Analytica Chimica Acta, 2009, 651 (2): 117- 138. doi: 10.1016/j.aca.2009.08.016
2	KERSTEN S , GARCIA-PEREZ M . Recent developments in fast pyrolysis of ligno-cellulosic materials[J]. Current Opinion in Biotechnology, 2013, 24 (3): 414- 420. doi: 10.1016/j.copbio.2013.04.003
3	BASSILAKIS R , CARANGELO R M , WO M A . TG-FTIR analysis of biomass pyrolysis[J]. Fuel, 2001, 80 (12): 1765- 1786. doi: 10.1016/S0016-2361(01)00061-8
4	SHAFIZADEH F . Introduction to pyrolysis of biomass[J]. Journal of Analytical and Applied Pyrolysis, 1982, 3 (4): 283- 305. doi: 10.1016/0165-2370(82)80017-X
5	HABIBI Y , LUCIA L A , ROJAS O J . Cellulose nanocrystals:Chemistry, self-assembly, and applications[J]. Chemical Reviews, 2010, 110 (6): 3479- 3500. doi: 10.1021/cr900339w
6	WATANABE A , MORITA S , OZAKI Y . Temperature-dependent structural changes in hydrogen bonds in microcrystalline cellulose studied by infrared and near-infrared spectroscopy with perturbation-correlation moving-window two-dimensional correlation analysis[J]. Applied Spectroscopy, 2006, 60 (6): 611- 618. doi: 10.1366/000370206777670549
7	WATANABE A , MORITA S , OZAKI Y . Study on temperature-dependent changes in hydrogen bonds in cellulose Iβ by infrared spectroscopy with perturbation-correlation moving-window two-dimensional correlation spectroscopy[J]. Biomacromolecules, 2006, 7 (11): 3164- 3170. doi: 10.1021/bm0603591
8	WANG S , DAI G , RU B , et al. Influence of torrefaction on the characteristics and pyrolysis behavior of cellulose[J]. Energy, 2017, 120, 864- 871. doi: 10.1016/j.energy.2016.11.135
9	YANG H , YAN R , CHEN H , et al. Characteristics of hemicellulose, cellulose and lignin pyrolysis[J]. Fuel, 2007, 86 (12/13): 1781- 1788.
10	ZHU G , ZHU X , XIAO Z , et al. Study of cellulose pyrolysis using an in situ visualization technique and thermogravimetric analyzer[J]. Journal of Analytical and Applied Pyrolysis, 2012, 94, 126- 130. doi: 10.1016/j.jaap.2011.11.016
11	XIN S , YANG H , CHEN Y , et al. Chemical structure evolution of char during the pyrolysis of cellulose[J]. Journal of Analytical and Applied Pyrolysis, 2015, 116, 263- 271. doi: 10.1016/j.jaap.2015.09.002
12	BOON J J , PASTOROVA I , BOTTO R E , et al. Structural studies on cellulose pyrolysis and cellulose chars by PyMS, PyGCMS, FTIR, NMR and by wet chemical techniques[J]. Biomass and Bioenergy, 1994, 7, 25- 32. doi: 10.1016/0961-9534(94)00044-T
13	BRADBURY A G W , SAKAI Y , SHAFIZADEH F . A kinetic model for pyrolysis of cellulose[J]. Journal of Applied Polymer Science, 1979, 23 (11): 3271- 3280.
14	BOUTIN O , FERRER M , LÉDÉ J . Radiant flash pyrolysis of cellulose:Evidence for the formation of short life time intermediate liquid species[J]. Journal of Analytical and Applied Pyrolysis, 1998, 47 (1): 13- 31. doi: 10.1016/S0165-2370(98)00088-6
15	刘倩, 王树荣, 王凯歌, 等. 纤维素热裂解过程中活性纤维素的生成和演变机理[J]. 物理化学学报, 2008, 24 (11): 1957- 1963.
16	MATSUOKA S , KAWAMOTO H , SAKA S . Thermal glycosylation and degradation reactions occurring at the reducing ends of cellulose during low-temperature pyrolysis[J]. Carbohydrate Research, 2011, 346 (2): 272- 279. doi: 10.1016/j.carres.2010.10.018
17	MATSUOKA S , KAWAMOTO H , SAKA S . What is active cellulose in pyrolysis? An approach based on reactivity of cellulose reducing end[J]. Journal of Analytical and Applied Pyrolysis, 2014, 106, 138- 146. doi: 10.1016/j.jaap.2014.01.011
18	MATSUOKA S , KAWAMOTO H , SAKA S . Reactivity of cellulose reducing end in pyrolysis as studied by methyl glucoside-impregnation[J]. Carbohydrate Research, 2016, 420, 46- 50. doi: 10.1016/j.carres.2015.11.010
19	ZHENG M , WANG Z , LI X , et al. Initial reaction mechanisms of cellulose pyrolysis revealed by ReaxFF molecular dynamics[J]. Fuel, 2016, 177, 130- 141. doi: 10.1016/j.fuel.2016.03.008
20	KWON G J , KIM D Y , KIMURA S , et al. Rapid-cooling, continuous-feed pyrolyzer for biomass processing.Preparation of levoglucosan from cellulose and starch[J]. Journal of Analytical and Applied Pyrolysis, 2007, 80 (1): 1- 5. doi: 10.1016/j.jaap.2006.12.012
21	PATWARDHAN P R , DALLUGE D L , SHANKS B H , et al. Distinguishing primary and secondary reactions of cellulose pyrolysis[J]. Bioresource Technology, 2011, 102 (8): 5265- 5269. doi: 10.1016/j.biortech.2011.02.018
22	PATWARDHAN P R , SATRIO J A , BROWN R C , et al. Product distribution from fast pyrolysis of glucose-based carbohydrates[J]. Journal of Analytical and Applied Pyrolysis, 2009, 86 (2): 323- 330. doi: 10.1016/j.jaap.2009.08.007
23	WANG S , GUO X , LIANG T , et al. Mechanism research on cellulose pyrolysis by Py-GC/MS and subsequent density functional theory studies[J]. Bioresource Technology, 2012, 104, 722- 728. doi: 10.1016/j.biortech.2011.10.078
24	SHEN D K , GU S . The mechanism for thermal decomposition of cellulose and its main products[J]. Bioresource Technology, 2009, 100 (24): 6496- 6504. doi: 10.1016/j.biortech.2009.06.095
25	PONDER G R , RICHARDS G N , STEVENSON T T . Influence of linkage position and orientation in pyrolysis of polysaccharides:A study of several glucans[J]. Journal of Analytical and Applied Pyrolysis, 1992, 22 (3): 217- 229. doi: 10.1016/0165-2370(92)85015-D
26	ZHANG X , YANG W , DONG C . Levoglucosan formation mechanisms during cellulose pyrolysis[J]. Journal of Analytical and Applied Pyrolysis, 2013, 104, 19- 27. doi: 10.1016/j.jaap.2013.09.015
27	董晓晨.综纤维素单糖热解生成糠醛与脱水糖衍生物的机理研究[D].北京:华北电力大学, 2017.
28	AWAD L , DEMANGE R , ZHU Y H , et al. The use of levoglucosenone and isolevoglucosenone as templates for the construction of C-linked disaccharides[J]. Carbohydrate Research, 2006, 341 (10): 1235- 1252. doi: 10.1016/j.carres.2006.04.008
29	FU Q , ARGYROPOULOS D S , TILOTTA D C , et al. Understanding the pyrolysis of CCA-treated wood.Part Ⅱ.Effect of phosphoric acid[J]. Journal of Analytical and Applied Pyrolysis, 2008, 82 (1): 140- 144. doi: 10.1016/j.jaap.2008.02.007
30	CASONI A I , NIEVAS M L , MOYANO E L , et al. Catalytic pyrolysis of cellulose using MCM-41 type catalysts[J]. Applied Catalysis A:General, 2016, 514, 235- 240. doi: 10.1016/j.apcata.2016.01.017
31	LU Q , YE X M , ZHANG Z B , et al. Catalytic fast pyrolysis of cellulose and biomass to produce levoglucosenone using magnetic SO₄^2-/TiO₂-Fe₃O₄[J]. Bioresource Technology, 2014, 171, 10- 15. doi: 10.1016/j.biortech.2014.08.075
32	WEI X , WANG Z , WU Y , et al. Fast pyrolysis of cellulose with solid acid catalysts for levoglucosenone[J]. Journal of Analytical and Applied Pyrolysis, 2014, 107, 150- 154. doi: 10.1016/j.jaap.2014.02.015
33	ZHANG H , MENG X , LIU C , et al. Selective low-temperature pyrolysis of microcrystalline cellulose to produce levoglucosan and levoglucosenone in a fixed bed reactor[J]. Fuel Processing Technology, 2017, 167, 484- 490. doi: 10.1016/j.fuproc.2017.08.007
34	RUTKOWSKI P . Catalytic effects of copper(Ⅱ) chloride and aluminum chloride on the pyrolytic behavior of cellulose[J]. Journal of Analytical and Applied Pyrolysis, 2012, 98, 86- 97. doi: 10.1016/j.jaap.2012.07.010
35	LU Q , YANG X C , DONG C Q , et al. Influence of pyrolysis temperature and time on the cellulose fast pyrolysis products:Analytical Py-GC/MS study[J]. Journal of Analytical and Applied Pyrolysis, 2011, 92 (2): 430- 438. doi: 10.1016/j.jaap.2011.08.006
36	LU Q , ZHANG Y , DONG C Q , et al. The mechanism for the formation of levoglucosenone during pyrolysis of β-D-glucopyranose and cellobiose:A density functional theory study[J]. Journal of Analytical and Applied Pyrolysis, 2014, 110 (1): 34- 43.
37	LIN Y , CHO J , TOMPSETT G A , et al. Kinetics and mechanism of cellulose pyrolysis[J]. Journal of Physical Chemistry C, 2009, 113 (46): 20097- 20107. doi: 10.1021/jp906702p
38	MANCINI I , DOSI F , DEFANT A , et al. Upgraded production of (1R, 5S)-1-hydroxy-3, 6-dioxa-bicyclo[3.2.1]octan-2-one from cellulose catalytic pyrolysis and its detection in bio-oils by spectroscopic methods[J]. Journal of Analytical and Applied Pyrolysis,, 2014, 110 (1): 285- 290.
39	FABBRI D , TORRI C , BARAVELLI V . Effect of zeolites and nanopowder metal oxides on the distribution of chiral anhydrosugars evolved from pyrolysis of cellulose:An analytical study[J]. Journal of Analytical and Applied Pyrolysis, 2007, 80 (1): 24- 29. doi: 10.1016/j.jaap.2006.12.025
40	SHAFIZADEH F , FURNEAUX R H , STEVENSON T T , et al. Acid-catalyzed pyrolytic synthesis and decomposition of 1, 4:3, 6-dianhydro-α-D-glucopyranose[J]. Carbohydrate Research, 1978, 61 (1): 519- 528. doi: 10.1016/S0008-6215(00)84510-3
41	SHAFIZADEH F , FURNEAUX R H , STEVENSON T T , et al. 1, 5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose and other pyrolysis products of cellulose[J]. Carbohydrate Research, 1978, 67 (2): 433- 447. doi: 10.1016/S0008-6215(00)84131-2
42	FURNEAUX R H , MASON J M , MILLER I J . A novel hydroxylactone from the lewis acid catalysed pyrolysis of cellulose[J]. Journal of the Chemical Society Perkin Transactions, 1988, 1 (1): 49- 51.
43	张阳, 陆强, 廖航涛, 等. 葡萄糖热解生成5-羟甲基糠醛机理[J]. 燃烧科学与技术, 2015, 21 (1): 89- 95.
44	MAYES H B , NOLTE M W , BECKHAM G T , et al. The alpha-bet(a) of glucose pyrolysis:Computational and experimental investigations of 5-hydroxymethylfurfural and levoglucosan formation reveal implications for cellulose pyrolysis[J]. ACS Sustainable Chemistry and Engineering, 2014, 2 (6): 1461- 1473. doi: 10.1021/sc500113m
45	HUANG J , LIU C , WEI S , et al. Density functional theory studies on pyrolysis mechanism of β-D-glucopyranose[J]. Journal of Molecular Structure:Theochem, 2010, 958 (1/2/3): 64- 70.
46	ZHANG Y , LIU C , XIE H . Mechanism studies on β-D-glucopyranose pyrolysis by density functional theory methods[J]. Journal of Analytical and Applied Pyrolysis, 2014, 105, 23- 34. doi: 10.1016/j.jaap.2013.09.016
47	PONDER G R , RICHARDS G N . Pyrolysis of inulin, glucose and fructose[J]. Carbohydrate Research, 1993, 244 (2): 341- 359. doi: 10.1016/0008-6215(83)85012-5
48	PAINE J B , PITHAWALLA Y B , NAWORAL J D . Carbohydrate pyrolysis mechanisms from isotopic labeling.Part 4.The pyrolysis of D-glucose:The formation of furans[J]. Journal of Analytical and Applied Pyrolysis, 2008, 83 (1): 37- 63. doi: 10.1016/j.jaap.2008.05.008
49	JADHAV H , PEDERSEN C M , SØLLING T , et al. 3-deoxy-glucosone is an intermediate in the formation of furfurals from D-glucose[J]. ChemSusChem, 2011, 4 (8): 1049- 1051. doi: 10.1002/cssc.201100249
50	KATŌ K . Pyrolysis of cellulose.Part Ⅲ.Comparative studies of the volatile coupounds from pyrolysates of cellulose and its related compounds[J]. Agricultural and Biological Chemistry, 1967, 31 (6): 657- 663.
51	廖艳芬, 郭振戈, 曹亚文, 等. 5-羟甲基糠醛热解机理的PY-GC-MS及原位红外法分析[J]. 华南理工大学学报(自然科学版), 2015, 43 (6): 15- 21. doi: 10.3969/j.issn.1000-565X.2015.06.003
52	NIKOLOV P Y , YAYLAYAN V A . Thermal decomposition of 5-(hydroxymethyl)-2-furaldehyde(HMF) and its further transformations in the presence of glycine[J]. Journal of Agricultural and Food Chemistry, 2011, 59 (18): 10104- 10113. doi: 10.1021/jf202470u
53	WANG M , LIU C , XU X , et al. Theoretical investigation on the carbon sources and orientations of the aldehyde group of furfural in the pyrolysis of glucose[J]. Journal of Analytical and Applied Pyrolysis, 2016, 120, 464- 473. doi: 10.1016/j.jaap.2016.06.019
54	PAINE J B , PITHAWALLA Y B , NAWORAL J D , et al. Carbohydrate pyrolysis mechanisms from isotopic labeling.Part 1:The pyrolysis of glycerin:Discovery of competing fragmentation mechanisms affording acetaldehyde and formaldehyde and the implications for carbohydrate pyrolysis[J]. Journal of Analytical and Applied Pyrolysis, 2007, 80 (2): 297- 311. doi: 10.1016/j.jaap.2007.03.007
55	PAINE J B , PITHAWALLA Y B , NAWORAL J D . Carbohydrate pyrolysis mechanisms from isotopic labeling.Part 2.The pyrolysis of D-glucose:General disconnective analysis and the formation of C1 and C2 carbonyl compounds by electrocyclic fragmentation mechanisms[J]. Journal of Analytical and Applied Pyrolysis, 2008, 82 (1): 10- 41.
56	PAINE J B , PITHAWALLA Y B , NAWORAL J D . Carbohydrate pyrolysis mechanisms from isotopic labeling.Part 3.The pyrolysis of D-glucose:Formation of C3 and C4 carbonyl compounds and a cyclopentenedione isomer by electrocyclic fragmentation mechanisms[J]. Journal of Analytical and Applied Pyrolysis, 2008, 82 (1): 42- 69. doi: 10.1016/j.jaap.2007.12.005
57	ZHANG M , GENG Z , YU Y . Density functional theory(DFT) study on the pyrolysis of cellulose:The pyran ring breaking mechanism[J]. Computational and Theoretical Chemistry, 2015, 1067, 13- 23. doi: 10.1016/j.comptc.2015.05.001
58	MATSUOKA S , KAWAMOTO H , SAKA S . Retro-aldol-type fragmentation of reducing sugars preferentially occurring in polyether at high temperature:Role of the ether oxygen as a base catalyst[J]. Journal of Analytical and Applied Pyrolysis, 2012, 93, 24- 32. doi: 10.1016/j.jaap.2011.09.005
59	SHAFIZADEH F , LAI Y Z . Thermal degradation of 1, 6-anhydro-β-D-glucopyranose[J]. Journal of Organic Chemistry, 1972, 37 (2): 278- 284. doi: 10.1021/jo00967a020
60	HEYNS K , KLIER M . Bräunungsreaktionen und fragmentierungen von kohlenhydraten:Teil Ⅳ.Vergleich der flüchtigen abbauprodukte bei der pyrolyse von mono-, oligo- und polysacchariden[J]. Carbohydrate Research, 1968, 6 (4): 436- 448. doi: 10.1016/S0008-6215(00)81239-2
61	LU Q , TIAN H Y , HU B , et al. Pyrolysis mechanism of holocellulose-based monosaccharides:The formation of hydroxyacetaldehyde[J]. Journal of Analytical and Applied Pyrolysis, 2016, 120, 15- 26. doi: 10.1016/j.jaap.2016.04.003
62	PONDER G R , RICHARDS G N . Pyrolysis of some ¹³C-labeled glucans:A mechanistic study[J]. Carbohydrate Research, 1993, 244 (1): 27- 47. doi: 10.1016/0008-6215(93)80003-W
63	HOUMINER Y , PATAI S . Pyrolytic reactions of carbohydrates.Part Ⅱ.Thermal decomposition of D-glucose[J]. Israel Journal of Chemistry, 1969, 7, 513- 524. doi: 10.1002/ijch.196900068

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Research Progress in Formation Mechanism of Typical Pyrolysis Products of Cellulose

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