Biomass Chemical Engineering ›› 2022, Vol. 56 ›› Issue (4): 67-76.doi: 10.3969/j.issn.1673-5854.2022.04.009
• Review Comment • Previous Articles
Haohan JIANG, Shuangming LI(), Sansan YU
Received:
2021-05-06
Online:
2022-07-30
Published:
2022-07-23
Contact:
Shuangming LI
E-mail:lishuangming@syuct.edu.cn
CLC Number:
Haohan JIANG, Shuangming LI, Sansan YU. Research Progress on Lignin Depolymerization and Liquid Phase Catalytic Degradation[J]. Biomass Chemical Engineering, 2022, 56(4): 67-76.
1 | 陈冰玉, 邸明伟. 木质素解聚研究新进展[J]. 高分子材料科学与工程, 2019, 35 (6): 157- 164. |
2 |
陶用珍, 管映亭. 木质素的化学结构及其应用[J]. 纤维素科学与技术, 2003, 11 (1): 42- 55.
doi: 10.3969/j.issn.1004-8405.2003.01.009 |
3 | 赵丽莎. 木质素结构及加氢解聚对其抗氧化活性的影响[D]. 广州: 华南理工大学, 2020. |
4 | JOFFRES B , LAURENTI D , CHARON N , et al. Thermochemical conversion of lignin for fuels and chemicals: A review[J]. Oil & Gas Science & Technology, 2013, 68 (4): 753- 763. |
5 | 陆强, 张栋, 朱锡锋. 四种金属氯化物对纤维素快速热解的影响(Ⅱ) 机理分析[J]. 化工学报, 2010, 61 (4): 1025- 1032. |
6 | SCHLOTZHAUER W S , SCHMELTZ I , HICKEY L C . Pyrolytic formation of phenols from some high molecular weight tobacco leaf sonstituents and related non-tobacco materials[J]. Top Science, 1967, 11, 31- 34. |
7 | CABALLERO J A , FONT R , MARCILLA A . Study of the primary pyrolysis of Kraft lignin at high heating rates: Yields and kinetics[J]. Journal of Analytical & Applied Pyrolysis, 1996, 36 (2): 159- 178. |
8 | ALÉN R , KUOPPALA E , OESCH P . Formation of the main degradation compound groups from wood and its components during pyrolysis[J]. Journal of Analytical & Applied Pyrolysis, 1996, 36 (2): 137- 148. |
9 | NUNN T R , HOWARD J B , LONGWELL J P , et al. Product compositions and kinetics in the rapid pyrolysis of milled wood lignin[J]. Industrial & Engineering Chemistry Process Design & Development, 1985, 24 (3): 844- 852. |
10 | IATRIDIS B , GAVALAS G R . Pyrolysis of a precipitated kraft lignin[J]. Industrial & Engineering Chemistry Product Research & Development, 1979, 18 (2): 127- 130. |
11 | BRITT P F , BUCHANAN A C , THOMAS K B , et al. Pyrolysis mechanisms of lignin: Surface-immobilized model compound investigation of acid-catalyzed and free-radical reaction pathways[J]. Journal of Analytical & Applied Pyrolysis, 1995, 33, 1- 19. |
12 |
DWIVEDI U N , SINGH P , PANDEY V P , et al. Structure-function relationship among bacterial, fungal and plant laccases[J]. Journal Molecular Catalysis B: Enzymatic, 2011, 68 (2): 117- 128.
doi: 10.1016/j.molcatb.2010.11.002 |
13 | 王晋东. 多元复合金属氧化物催化解聚木质素的研究[D]. 合肥: 中国科学技术大学, 2020. |
14 |
熊乙, 杨富裕, 倪奎奎, 等. 微生物在木质纤维素降解中的应用进展[J]. 草学, 2019, (5): 1- 7.
doi: 10.3969/j.issn.2096-3971.2019.05.001 |
15 |
付春霞, 付云霞, 邱忠平, 等. 木质素生物降解的研究进展[J]. 浙江农业学报, 2014, 26 (4): 1139- 1144.
doi: 10.3969/j.issn.1004-1524.2014.04.53 |
16 | JIN L , DUNIERE L , LYNCH J P , et al. Impact of ferulic acid esterase producing lactobacilli and fibrolytic enzymes on conservation characteristics, aerobic stability and fiber degradability of barley silage[J]. Animal Feed Science & Technology, 2015, 207, 62- 74. |
17 |
GONZALO G D , COLPA D I , HABIB M , et al. Bacterial enzymes involved in lignin degradation[J]. Journal of Biotechnology, 2016, 236, 110- 119.
doi: 10.1016/j.jbiotec.2016.08.011 |
18 |
ZHANG X S , LEI H W , CHEN S L , et al. Catalytic co-pyrolysis of lignocellulosic biomass with polymers: A critical review[J]. Green Chemistry, 2016, 18, 4145- 4169.
doi: 10.1039/C6GC00911E |
19 | CZERNIK S. Catalytic Pyrolysis of Biomass[M]//LEE J W. Advanced Biofuels and Bioproducts. New York: Springer, 2013: 119-127 |
20 | SESHAN K. Catalytic Pyrolysis of Lignocellulosic Biomass[M]//SA J. Fuel Production with Heterogeneous Catalysis. Boca Raton: CRC Press, 2014: 253-280 |
21 | AHO A, SALMI T, MURZIN D Y, et al. Catalytic Pyrolysis of Lignocellulosic Biomass[M]//TRIANTAFYLLIDIS K S, LAPPAS A A, STÖCKER M. The Role of Catalysis for the Sustainable Production of Bio-fuels and Bio-chemicals, Amsterdam: Elsevier, 2013: 137-159. |
22 |
MA Z , CUSTODIS V , HEMBERGER P , et al. Chemicals from lignin by catalytic fast pyrolysis, from product control to reaction mechanism[J]. Chimia, 2015, 69 (10): 597- 602.
doi: 10.2533/chimia.2015.597 |
23 | MA Z Q , TROUSSARD E , VAN BOKHOVEN J A . Controlling the selectivity to chemicals from lignin via catalytic fast pyrolysis[J]. Applied Catalysis A: General, 2012, 423/424 (18): 130- 136. |
24 |
MIHALCIK D J , MULLEN C A , BOATENG A A , et al. Screening acidic zeolites for catalytic fast pyrolysis of biomass and its components[J]. Journal of Analytical and Applied Pyrolysis, 2011, 92 (1): 224- 232.
doi: 10.1016/j.jaap.2011.06.001 |
25 | NGUYEN J D, MATSUURA B S, STEPHENSON C R J. ChemInform abstract: A photochemical strategy for lignin degradation at room temperature[J/OL]. ChemInform, 2014, 45(34): 032[2021-04-20]. https://doi.org/10.1002/chin.201434032. |
26 |
NGUYEN J D , MATSUURA B S , STEPHENSON C R J . A photochemical strategy for lignin degradation at room temperature[J]. Journal of the American Chemical Society, 2014, 136 (4): 1218- 1221.
doi: 10.1021/ja4113462 |
27 |
廖声甫, 刘琪英, 马隆龙. 蒽醌-2-羧酸作为光催化剂催化解聚木质素[J]. 新能源进展, 2020, 8 (5): 339- 349.
doi: 10.3969/j.issn.2095-560X.2020.05.001 |
28 |
WU X J , FAN X T , XIE S J , et al. Solar energy-driven lignin-first approach to full utilization of lignocellulosic biomass under mild conditions[J]. Nature Catalysis, 2018, 1 (10): 772- 780.
doi: 10.1038/s41929-018-0148-8 |
29 |
陈云平, 傅艳斌, 杨平, 等. 纳米TiO2光催化降解碱木质素研究[J]. 生物质化学工程, 2009, 43 (6): 31- 35.
doi: 10.3969/j.issn.1673-5854.2009.06.007 |
30 |
王静, 石燕, 杨宏旻, 等. 木质素共溶剂热解液化动力学研究[J]. 南京师范大学学报(工程技术版), 2017, 17 (4): 86- 92.
doi: 10.3969/j.issn.1672-1292.2017.04.014 |
31 |
HONG-SHIK L , JUNGHO J , JEONG-MYEONG H , et al. Hydro- and solvothermolysis of kraft lignin for maximizing production of monomeric aromatic chemicals[J]. Bioresource Technology, 2016, 203, 142- 149.
doi: 10.1016/j.biortech.2015.12.022 |
32 |
VAQUERIZO L , ABAD-FERNÁNDEZ N , MATO R B , et al. Redefining conventional biomass hydrolysis models by including mass transfer effects.Kinetic model of cellulose hydrolysis in supercritical water[J]. Chemical Engineering Journal, 2018, 350, 463- 473.
doi: 10.1016/j.cej.2018.05.077 |
33 | 包守庆, 孙剑飞, 银建中. 超/亚临界水中木质纤维素水解转化制化学品[J]. 应用科技, 2020, 47 (5): 100- 106. |
34 | 曹禹. 钴基催化剂催化解聚木质素的研究[D]. 淮南: 安徽理工大学, 2019. |
35 | 刘振, 谢梅竹, 赵绘婷, 等. 木质素液相催化解聚研究现状[J]. 林产工业, 2020, 57 (10): 1- 7. |
36 | 宋武林. 铈基催化剂在木质素催化解聚中的应用[D]. 昌吉: 昌吉学院, 2020. |
37 | 汤志远. 钼基海泡石催化剂解聚木质素的研究[D]. 淮南: 安徽理工大学, 2020. |
38 | STURGEON M R , KIM S , LAWRENCE K , et al. A mechanistic investigation of acid-catalyzed cleavage of aryl-ether linkages: Implications for lignin depolymerization in acidic environments[J]. ACS Sustainable Chemistry & Engineering, 2013, 2 (3): 472- 485. |
39 |
GIERER J . Chemistry of delignification[J]. Wood Science and Technology, 1985, 19 (4): 289- 312.
doi: 10.1007/BF00350807 |
40 | FEARON O, KUITUNEN S, RUUTTUNEN K, et al. Detailed modeling of kraft pulping chemistry: Carbohydrate reactions[J/OL]. AIChE Journal, 2020, 66(8): e16252[2021-04-20]. https://doi.org/10.1002/aic.16251. |
41 |
GOMES V J , JAMEEL H , CHANG H M , et al. Effects of lignin chemistry on oxygen delignification performance[J]. Tappi Journal, 2018, 17 (7): 373- 381.
doi: 10.32964/TJ17.07.373 |
42 |
STURGEON M R , O'BRIEN M H , CIESIELSKI P N , et al. Lignin depolymerisation by nickel supported layered-double hydroxide catalysts[J]. Green Chemistry, 2014, 16, 824- 835.
doi: 10.1039/C3GC42138D |
43 |
KRUGER J S C N S , HANG S , ET A L . Lignin depolymerization with nitrate-intercalated hydrotalcite catalysts[J]. Acs Catalysis, 2016, 6 (2): 1316- 1328.
doi: 10.1021/acscatal.5b02062 |
44 | CHAUDHARY R , DHEPE P L . Solid base catalyzed depolymerization of lignin into low molecular weight products[J]. Green Chemistry, 2016, 19, 778- 788. |
45 | RUI K , MITTAL A , MCKINNEY K , et al. Evaluation of clean fractionation pretreatment for the production of renewable fuels and chemicals from corn stover[J]. Chemical & Pharmaceutical Bulletin, 2014, 2 (6): 1364- 1376. |
46 | LI C Z , ZHENG M Y , WANG A Q , et al. One-pot catalytic hydrocracking of raw woody biomass into chemicals over supported carbide catalysts: Simultaneous conversion of cellulose, hemicellulose and lignin[J]. Energy & Environmental Science, 2012, 5 (4): 6383- 6390. |
47 |
BEAUCHET R , MONTEIL-RIVERA F , LAVOIE J M . Conversion of lignin to aromatic-based chemicals(L-chems) and biofuels(L-fuels)[J]. Bioresource Technology, 2012, 121, 328- 334.
doi: 10.1016/j.biortech.2012.06.061 |
48 | TOLEDANO A , SERRANO L , LABIDI J , et al. Organosolv lignin depolymerization with different base catalysts[J]. Journal of Chemical Technology & Biotechnology, 2012, 87 (11): 1593- 1599. |
49 | GALKIN M V , SAWADJOON S , ROHDE V , et al. Mild heterogeneous palladium-catalyzed cleavage of β-O-4'-ether linkages of lignin model compounds and native lignin in air[J]. ChemCatChem, 2014, 6 (1): 179- 184. |
50 | GALKIN M V , SAWADJOON S , ROHDE V , et al. ChemInform abstract: Mild heterogeneous palladium-catalyzed cleavage of β-O-4'-ether linkages of lignin model compounds and native lignin in air[J]. ChemInform, 2014, 45 (30): 179- 184. |
51 | MOTTWEILER J. Transition metal-catalyzed oxidative cleavage of lignin and lignin β-O-4 model compounds[D]. Aachen, Germany: RWTH Aachen University, 2016. |
52 | ZHU Y T, JING Y R, LIU C B, et al. Cleavage of the β-O-4 bond of bignin model compounds catalyzed by an acidic ionic liquid, 1-H-3-methylimidazolium chloride: A DFT study[C]//中国化学会. 第十三届全国量子化学会议论文集——第一分会: 电子结构理论与计算方法. 大连: 中国化学会, 2017. |
53 | PARSELL T H , OWEN B C , KLEIN I , et al. Cleavage and hydrodeoxygenation(HDO) of C—O bonds relevant to lignin conversion using Pd/Zn synergistic catalysis[J]. Chemical Science, 2013, 4 (2): 806- 813. |
54 | SAHA B , KLEIN I , PARSELL T , et al. Catalytic Hydrodeoxygenation of Lignin Model compounds[M]. Singapore: Springer, 2016. |
55 | PARSELL T H , OWEN B C , KLEIN I , et al. Cleavage and hydrodeoxygenation(HDO) of C-O bonds relevant to lignin conversion using Pd/Zn synergistic catalysis[J]. Chemical Science, 2013, 4 (2): 806- 813. |
56 | GUO H , LI C , QI Z , et al. Tungsten-based catalysts for lignin depolymerization: The role of tungsten species in C—O bond cleavage[J]. Catalysis Science & Technology, 2019, 9, 2144- 2151. |
57 | GUO H W , ZHANG B , LI C Z , et al. Tungsten carbide: A remarkably efficient catalyst for the selective cleavage of lignin C—O Bonds[J]. ChemSusChem, 2016, 9 (22): 3220- 3229. |
58 | MA Y Y , DU Z T , LIU J X , et al. Selective oxidative C—C bond cleavage of a lignin model compound in the presence of acetic acid with a vanadium catalyst[J]. Green Chemistry, 2015, 17, 4968- 4973. |
59 | FARGUES C , MATHIAS L , RODRIGUES A . Kinetics of vanillin production from Kraft lignin oxidation[J]. Industrial & Engineering Chemistry Research, 1996, 35 (1): 313- 314. |
60 | FARGUES C , MATHIAS L , SILVA J , et al. Kinetics of vanillin oxidation[J]. Chemical Engineering & Technology, 2010, 19 (2): 127- 136. |
61 | FAWZY A, ZAAFARANY I. Kinetics and mechanism of oxidation of vanillin by chromium(VI) in sulfuric acid medium[J/OL]. Modern Chemistry & Applications, 2016, 4(2): 179[2021-04-20]. https://doi.org/10.4172/2329-6798.1000179. |
62 | TARABANKO V E , HENDOGINA Y V , PETUHOV D V , et al. On the role of retroaldol reaction in the process of lignin oxidation into vanillin.Kinetics of the vanillideneacetone cleavage in alkaline media[J]. Reaction Kinetics and Catalysis Letters, 2000, 69 (2): 361- 368. |
63 | GIERER J . Chemistry of delignification.Part 2:Reactions of lignins during bleaching[J]. Wood Science & Technology, 1986, 20 (1): 1- 33. |
64 | GIERER J . The chemistry of delignification.A General Concept[J]. Holzforschung, 1982, 36 (1): 43- 51. |
65 | SHAO Y, XIA Q, DONG L, et al. Selective production of arenes via direct lignin upgrading over a niobium-based catalyst[J]. Nature Communications, 2017, 8: 16104[2021-04-20]. https://doi.org/10.1038/ncomms16104. |
66 | 李昌志, 郭海威, 王爱琴, 等. 富氧空位氧化钨负载催化剂在木质素解聚中的应用: CN111215090A[P]. 2020-06-02 |
67 | 郑云武, 王继大, 刘灿, 等. Ni-P/HZSM-5催化木质素降解制备酚类化学品[J]. 化工进展, 2020, 39 (5): 1792- 1802. |
68 | 杨倩, 刘贵峰, 金灿, 等. 路易斯酸复合Pt/ZrO2协同催化碱木质素还原降解制备酚类低聚物[J]. 林产化学与工业, 2020, 40 (6): 37- 49. |
69 | 刘晓乐, 李淑君, 任世学, 等. H3PW12O40/ZrO2催化降解酶解木质素及抗氧化性的研究[J]. 太阳能学报, 2020, 41 (4): 249- 256. |
[1] | Lei WANG, Xinyuan BI, Fei YE, Yibei LIU, Min WU, Peng LU. Research Progress of Biomass-based Porous Materials on Thermal Insulation Materials [J]. Biomass Chemical Engineering, 2022, 56(4): 58-66. |
[2] | Ning LI, Jingyi LIU, Chunpeng WANG, Fuxiang CHU, Yuzhi XU. Preparation and Properties of Soybean Meal Adhesives Modified by Lignin Amine [J]. Biomass Chemical Engineering, 2022, 56(3): 23-28. |
[3] | Jurong REN, Yunhong SU, Hao YING, Yunjuan SUN, Wei XU, Hang YIN. Research Progress of Biomass Gasification for Hydrogen-rich Syngas [J]. Biomass Chemical Engineering, 2022, 56(3): 39-46. |
[4] | Kaixin ZHANG, Yalan YU, Yuting DUAN, Changwei WU, Lei XUE, Pengfei HUO. Demethylation/Hydroxyethylation Combined Modification of Corn Straw Lignin [J]. Biomass Chemical Engineering, 2022, 56(2): 9-13. |
[5] | Hao SUN, Yunjuan SUN, Mingzhe MA, Kang SUN, Jianchun JIANG. Development Trend and Strategic Countermeasures of Forestry Resources Gasification, Heat Supply and Power Generation Industry [J]. Biomass Chemical Engineering, 2022, 56(2): 40-48. |
[6] | Haodong FAN, Dongwang ZHANG, Bin ZHAO, Man ZHANG, Yan JIN. Summary of Corrosion Characteristics and Inhibition Methods of Biomass Fluidized Bed [J]. Biomass Chemical Engineering, 2022, 56(1): 30-36. |
[7] | Meijuan ZHONG, Xing′e LIU, Lili SHANG, Genlin TIAN, Shumin YANG, Jianfeng MA. Research Advance on Adjustment of Pore Structure of Plant-based Activated Carbon [J]. Biomass Chemical Engineering, 2022, 56(1): 57-66. |
[8] | Meiling XIA, Yunpu WANG, Shumei ZHANG, Yuan ZENG, Yuhuan LIU, Roger RUAN. Research Progress on Comprehensive Utilization of Camellia oleifera Abel Shell [J]. Biomass Chemical Engineering, 2021, 55(6): 26-38. |
[9] | Yang LI, Kai LI, Zhenxi ZHANG, Shiyu FENG, Bin HU, Qiang LU. Research Progress on Catalytic Pyrolysis of Biomass with Alkaline Earth Metal Oxide-based Catalysts [J]. Biomass Chemical Engineering, 2021, 55(6): 39-48. |
[10] | Yanchun FU, Tengfei GAO, Liping ZHANG, Ruihong MENG, Yang YANG, Xiongwei LI. Advance on Bio-refining for the Production of Furfural [J]. Biomass Chemical Engineering, 2021, 55(6): 59-66. |
[11] | Junna BIAN, Jian CHEN, Guomin WU, Zhenwu KONG. Progress of Itaconic Acid Light Curable Resins [J]. Biomass Chemical Engineering, 2021, 55(5): 53-59. |
[12] | Xiaolu WANG, Xuefeng YAO, Yuxin CHEN, Huacong ZHOU, Quansheng LIU. Research Progress on Zirconium/Hafnium Based Hydrogen Transfer Catalyst [J]. Biomass Chemical Engineering, 2021, 55(4): 66-76. |
[13] | Dongyang HE, Guowei LIANG, Xinyang LI, Shuangyi WU, Miaomiao NIU. Research Review on Cracking and Removal of Tar Catalyzed by Biomass Coke [J]. Biomass Chemical Engineering, 2021, 55(4): 77-84. |
[14] | Dichao WU, Chao CHEN, Xinglong HOU, Kang SUN. Effect of Pyrolysis Temperature on Structures of Chars Forming from Cellulose and Lignin [J]. Biomass Chemical Engineering, 2021, 55(3): 1-9. |
[15] | Xiaojin HU, Tao YANG, Sanju LIU, Jun LIU, Shoujun ZHANG, Yirui LI. Effect of Gasification Temperature of Circulating Fluidized Bed on Solid Product Feature of Rice Husk Gasification [J]. Biomass Chemical Engineering, 2021, 55(3): 23-28. |
Viewed | ||||||
Full text |
|
|||||
Abstract |
|
|||||