电化学催化木质素解聚的研究进展

doi:10.3969/j.issn.0253-2417.2022.01.015

Abstract

Abstract:

In this article, the research progress of electrochemical technology of lignin depolymerization recently, including micro electrochemical expression of lignin depolymerization, types of catalysts, electrode materials and electrode mechanism of electrochemical reactor and other strategies, were reviewed. The frontier research of lignin depolymerization by electrochemical technology combined with ionic liquid catalysis system, biological enzyme catalysis system and photocatalysis technology were analyzed. The influences of electrode material and current density on electrocatalytic efficiency were summarized, and the challenges as well as the opportunities of the application of electrochemical technology were presented.

Key words: electrochemical, lignin depolymerization, organic compounds, electrode, reactors

CLC Number:

TQ35
O641

Chunhui MA, Jifang ZHANG, Wei LI, Sha LUO, Shouxin LIU, Jian LI. Research Progress in Electrochemically Catalyzed Depolymerization of Lignin[J]. Chemistry and Industry of Forest Products, 2022, 42(1): 110-122.

Figures/Tables 4

References 60

1	雷学军, 罗梅健. 生物质能转化技术及资源综合开发利用研究[J]. 中国能源, 2010, 32 (1): 22- 28, 46. doi: 10.3969/j.issn.1003-2355.2010.01.005
	LEI X J , LUO M J . Analysis on biomass energy conversion technology and resource comprehensive development and utilization[J]. Energy of China, 2010, 32 (1): 22- 28, 46. doi: 10.3969/j.issn.1003-2355.2010.01.005
2	LYU X Y , LI Q X , JIANG Z C , et al. Structure characterization and pyrolysis behavior of organosolv lignin isolated from corncob residue[J]. Journal of Analytical and Applied Pyrolysis, 2018, 136, 115- 124. doi: 10.1016/j.jaap.2018.10.016
3	陈冰玉, 郝国夏, 张瀚文, 等. 木质素水热解聚研究进展[J]. 化学与黏合, 2018, 40 (6): 435- 439. doi: 10.3969/j.issn.1001-0017.2018.06.013
	CHEN B Y , HAO G X , ZHANG H W , et al. Research progress on hydrothermal depolymerization of lignin[J]. Chemistry and Adhesion, 2018, 40 (6): 435- 439. doi: 10.3969/j.issn.1001-0017.2018.06.013
4	刘光勇, 王倩, 张雅琴, 等. 离子液体中催化解聚木质素研究现状[J]. 中国科学: 化学, 2020, 50 (2): 259- 270.
	LIU G Y , WANG Q , ZHANG Y Q , et al. Degradation of lignin in ionic liquids: A review[J]. Scientia Sinica Chimica, 2020, 50 (2): 259- 270.
5	麦富航. 木质素及其模型化合物高选择性地转化为芳香族化学品[D]. 天津: 天津大学, 2018.
	MAI F H. Lignin and its model compounds are highly selectively transformed into aromatic chemicals[D]. Tianjin: Tianjin University, 2018.
6	AGARWAL A , RANA M , PARK J . Advancement in technologies for the depolymerization of lignin[J]. Fuel Processing Technology, 2018, 181, 115- 132. doi: 10.1016/j.fuproc.2018.09.017
7	KUZNETSOV B N , GARYNTSEVA N V , KUZNETSOVA S A , et al. Green catalytic processing of native and organosolv lignins[J]. Catalysis Today, 2018, 309, 18- 30. doi: 10.1016/j.cattod.2017.11.036
8	BUTTI S K , VELVIZHI G , SULONEN M L K , et al. Microbial electrochemical technologies with the perspective of harnessing bioenergy: Maneuvering towards upscaling[J]. Renewable and Sustainable Energy Reviews, 2016, 53, 462- 479. doi: 10.1016/j.rser.2015.08.058
9	MOVIL-CABRERA O , RODRIGUEZ-SILVA A , ARROYO-TORRES C , et al. Electrochemical conversion of lignin to useful chemicals[J]. Biomass and Bioenergy, 2016, 88, 89- 96. doi: 10.1016/j.biombioe.2016.03.014
10	MA R S , GUO M , ZHANG X . Recent advances in oxidative valorization of lignin[J]. Catalysis Today, 2018, 302, 50- 60. doi: 10.1016/j.cattod.2017.05.101
11	BAWARETH B , DI MARINO D , NIJHUIS T A , et al. Unravelling electrochemical lignin depolymerization[J]. ACS Sustainable Chemistry & Engineering, 2018, 6 (6): 7565- 7573.
12	LAHIVE C W , KAMER P C J , LANCEFIELD C S , et al. An introduction to model compounds of lignin linking motifs; synthesis and selection considerations for reactivity studies[J]. ChemSusChem, 2020, 13 (17): 4238- 4265. doi: 10.1002/cssc.202000989
13	CHEN J , YANG H L , FU H Q , et al. Electrochemical oxidation mechanisms for selective products due to C-O and C-C cleavages of β-O-4 linkages in lignin model compounds[J]. Physical Chemistry Chemical Physics, 2020, 22 (20): 11508- 11518. doi: 10.1039/D0CP01091J
14	SHIRAISHI T , TAKANO T , KAMITAKAHARA H , et al. Studies on electrooxidation of lignin and lignin model compounds.Part 1:Direct electrooxidation of non-phenolic lignin model compounds[J]. Holzforschung, 2012, 66 (3): 303- 309.
15	SHIRAISHI T , TAKANO T , KAMITAKAHARA H , et al. Studies on electro-oxidation of lignin and lignin model compounds.Part 2:N-Hydroxyphthalimide(NHPI)-mediated indirect electro-oxidation of non-phenolic lignin model compounds[J]. Holzforschung, 2012, 66 (3): 311- 315.
16	GAO W , LAM C , SUN B , et al. Selective electrochemical C-O bond cleavage of β-O-4 lignin model compounds mediated by iodide ion[J]. Tetrahedron, 2017, 73 (17): 2447- 2454. doi: 10.1016/j.tet.2017.03.027
17	BATENI F , GHAHREMANI R , STASER J A . Electrochemical oxidative valorization of lignin by the nanostructured PbO₂/MWNTs electrocatalyst in a low-energy depolymerization process[J]. Journal of Applied Electrochemistry, 2020, 51, 65- 78.
18	YAN K L , ZHANG Y , TU M B , et al. Electrocatalytic valorization of organosolv lignin utilizing a nickel-based electrocatalyst[J]. Energy & Fuels, 2020, 34 (10): 12703- 12709.
19	WIJAYA Y P , SMITH K J , KIM C S , et al. Synergistic effects between electrocatalyst and electrolyte in the electrocatalytic reduction of lignin model compounds in a stirred slurry reactor[J]. Journal of Applied Electrochemistry, 2018, 72 (11): 951- 960.
20	GHAHREMANI R, STASER J A. Electrochemical oxidation of lignin for the production of value-added chemicals on Ni-Co bimetallic electrocatalysts[J/OL]. Holzforschung, 2018: 1-10[2020-09-15]. https://doi.org/10.1515/hf-2018-0041.
21	ZIRBES M , WALDVOGEL S R . Electro-conversion as sustainable method for the fine chemical production from the biopolymer lignin[J]. Current Opinion in Green and Sustainable Chemistry, 2018, 14, 19- 25. doi: 10.1016/j.cogsc.2018.05.001
22	GAREDEW M , LIN F , SONG B , et al. Greener routes to biomass waste valorization: Lignin transformation through electrocatalysis for renewable chemicals and fuels production[J]. ChemSusChem, 2020, 13 (17): 4214- 4237. doi: 10.1002/cssc.202000987
23	韩笑, 兰春杏, 沈大宇, 等. 诱导基团参与电化学降解甘蔗渣木质素[J]. 应用化工, 2019, 48 (10): 2316- 2319. doi: 10.3969/j.issn.1671-3206.2019.10.011
	HAN X , LAN C X , SHEN D Y , et al. Participation of induced-group in electrochemical degradation of bagasse lignin[J]. Applied Chemical Industry, 2019, 48 (10): 2316- 2319. doi: 10.3969/j.issn.1671-3206.2019.10.011
24	HORN E J , ROSEN B R , CHEN Y , et al. Scalable and sustainable electrochemical allylic C-H oxidation[J]. Nature, 2016, 533 (7601): 77- 81. doi: 10.1038/nature17431
25	DU X , LIU W , ZHANG Z , et al. Low-energy catalytic electrolysis for simultaneous hydrogen evolution and lignin depolymerization[J]. ChemSusChem, 2017, 10 (5): 847- 854. doi: 10.1002/cssc.201601685
26	SANNAMI Y, KAMITAKAHARA H, TAKANO T. TEMPO-mediated electro-oxidation reactions of non-phenolic β-O-4 type lignin model compounds[J/OL]. Holzforschung, 2017, 71(2): 1-9[2020-09-15]. https://doi.org/10.1515/hf-2016-0117.
27	袁露. 在碱性溶液中电催化氢化降解竹木质素生成间二乙苯的研究[D]. 天津: 河北工业大学, 2015.
	YUAN L. Study on electrocatalytic hydrogenation of bamboo lignin to m-diethylbenzene in alkaline solution[D]. Tianjin: Hebei University of Technology, 2015.
28	ZHANG Y M , PENG Y , YIN X L , et al. Degradation of lignin to BHT by electrochemical catalysis on Pb/PbO₂ anode in alkaline solution[J]. Journal of Chemical Technology, 2014, 89 (12): 1954- 1960.
29	XU H, YUAN Q S, SHAO D, et al. Fabrication and characterization of PbO₂ electrode modified with[Fe(CN)₆] ^3- and its application on electrochemical degradation of alkali lignin[J]. Journal of Hazardous Materials, 2015, 286: 509-516.
30	张一鸣. 碱性均相体系中Pb/PbO₂电极电催化降解木质素制备2, 6-二叔丁基-4-甲基苯酚的研究[D]. 天津: 河北工业大学, 2013.
	ZHANG Y M. Preparation of 2, 6-ditertbutyl-4-methylphenol by electrocatalytic degradation of lignin on Pb/PbO₂ electrode in alkaline homogeneous system[D]. Tianjin: Hebei University of Technology, 2013.
31	SHEN D Y , YU X Q , YUAN L , et al. Selective production of 1, 3-diethylbenzene by electrocatalytic hydrocracking of bamboo lignin in alkaline solution[J]. ChemistrySelect, 2019, 4 (35): 10430- 10435. doi: 10.1002/slct.201902429
32	WANG Y S , YANG F , LIU Z H , et al. Electrocatalytic degradation of aspen lignin over Pb/PbO₂ electrode in alkali solution[J]. Catalysis Communications, 2015, 67, 49- 53. doi: 10.1016/j.catcom.2015.03.033
33	CAI P , FAN H X , CAO S , et al. Electrochemical conversion of corn stover lignin to biomass-based chemicals between Cu/Ni-Mo-Co cathode and Pb/PbO₂ anode in alkali solution[J]. Electrochimica Acta, 2018, 264, 128- 139. doi: 10.1016/j.electacta.2018.01.111
34	刘苗苗. 在Pb/PbO₂和Cu电极间电催化氧化还原降解碱性竹木质素制备有价值化学品的研究[D]. 天津: 河北工业大学, 2017.
	LIU M M. Preparation of valuable chemicals from alkaline bamboo lignin by electrocatalytic oxidation-reduction between Pb/PbO₂ and Cu electrodes[D]. Tianjin: Hebei University of Technology, 2017.
35	PAN K , TIAN M , JIANG Z H , et al. Electrochemical oxidation of lignin at lead dioxide nanoparticles photoelectrodeposited on TiO₂ nanotube arrays[J]. Electrochimica Acta, 2012, 60, 147- 153. doi: 10.1016/j.electacta.2011.11.025
36	尚园园. 碱性溶液中在镍电极上电催化降解玉米秸秆木质素转化为芳香化合物的研究[D]. 天津: 河北工业大学, 2017.
	SHANG Y Y. Electrocatalytic degradation of lignin from corn stover to aromaticity on nickel electrode in alkaline solution[D]. Tianjin: Hebei University of Technology, 2017.
37	LAN C X , FAN H X , SHANG Y Y , et al. Electrochemically catalyzed conversion of cornstalk lignin to aromatic compounds: an integrated process of anodic oxidation of a Pb/PbO₂ electrode and hydrogenation of a nickel cathode in sodium hydroxide solution[J]. Sustainable Energy & Fuels, 2020, 4 (4): 1828- 1836.
38	MICHAEL Z , DOMINIK S , NICOLE B , et al. Anodic degradation of lignin at active transition metal-based alloys and performance-enhanced anodes[J]. ChemElectroChem, 2019, 6 (1): 155- 161. doi: 10.1002/celc.201801218
39	ANDRE C , FLORENCE C , PAUL J , et al. Electrocatalytic hydrogenation of lignin models at Raney nickel and palladium-based electrodes[J]. Canadian Journal of Chemistry, 2000, 78, 307- 315. doi: 10.1139/v00-009
40	MAHDAVI B , LAFRANCE A , MARTEL A , et al. Electrocatalytic hydrogenolysis of lignin model dimers at Raney nickel electrodes[J]. Journal of Applied Electrochemistry, 1997, 27, 605- 611. doi: 10.1023/A:1018463131891
41	TOLBA R , TIAN M , WEN J , et al. Electrochemical oxidation of lignin at IrO₂-based oxide electrodes[J]. Journal of Electroanalytical Chemistry, 2010, 649 (1): 9- 15.
42	SHAO D , LIANG J , CUI X , et al. Electrochemical oxidation of lignin by two typical electrodes: Ti/SbSnO₂ and Ti/PbO₂[J]. Chemical Engineering Journal, 2014, 244, 288- 295. doi: 10.1016/j.cej.2014.01.074
43	SINGH S , GHATAK H R . Vanillin formation by electrooxidation of lignin on stainless steel anode: Kinetics and by-products[J]. Journal of Wood Chemistry and Technology, 2017, 37 (6): 407- 422. doi: 10.1080/02773813.2017.1310899
44	彭莹. Ti/SnO₂-Sb₂O₃/α-PbO₂/β-PbO₂电极电催化降解碱木质素的研究[D]. 天津: 河北工业大学, 2014.
	PENG Y. Electrocatalytic degradation of alkali lignin on Ti/SnO₂-Sb₂O₃/α-PbO₂/β-PbO₂ electrode[D]. Tianjin: Hebei University of Technology, 2014.
45	汪永生. 在三维电极反应器中电催化降解杨木木质素碱溶液制备对甲基苯甲醚的研究[D]. 天津: 河北工业大学, 2015.
	WANG Y S. Preparation of p-methyl anisole from alkali solution of poplar lignin by electrocatalytic degradation in a three-dimensional electrode reactor[D]. Tianjin: Hebei University of Technology, 2015.
46	STIEFEL S , LOLSBERG J , KIPSHAGEN L , et al. Controlled depolymerization of lignin in an electrochemical membrane reactor[J]. Electrochemistry Communications, 2015, 61, 49- 52. doi: 10.1016/j.elecom.2015.09.028
47	MARINO D D , ANIKO V , STOCCO A , et al. Emulsion electro-oxidation of Kraft lignin[J]. Green Chemistry, 2017, 19 (20): 4778- 4784. doi: 10.1039/C7GC02115A
48	CARAVACA A , GARCIA L W E , GIL S , et al. Towards a sustainable technology for H₂ production: Direct lignin electrolysis in a continuous-flow polymer electrolyte membrane reactor[J]. Electrochemistry Communications, 2019, 100, 43- 47. doi: 10.1016/j.elecom.2019.01.016
49	彭汪锋. 碱性溶液中电催化还原竹木质素生成叔丁基对苯二酚的研究[D]. 天津: 河北工业大学, 2016.
	PENG W F. Electrocatalytic reduction of bamboo lignin to tert-butyl hydroquinone in alkaline solution[D]. Tianjin: Hebei University of Technology, 2016.
50	许仃仃, 王守娟, 孔凡功, 等. 工业针叶木硫酸盐木质素的电化学氧化降解研究[J]. 中国造纸, 2019, 38 (6): 20- 26.
	XU D D , WANG S J , KONG F G , et al. Electrochemical degradation of industrial softwood Kraft lignin[J]. China Pulp & Paper, 2019, 38 (6): 20- 26.
51	POPOVA O V , MALTSEVA T A , MAREVA E A , et al. Electrochemical oxidation of hydrolytic lignins in fluoride-containing aqueous electrolytes[J]. Russian Journal of General Chemistry, 2018, 88 (16): 1331- 1336.
52	许仃仃. 针叶木硫酸盐木素的电化学降解及改性研究[D]. 济南: 齐鲁工业大学, 2019.
	XU D D. Study on electrochemical degradation and modification of softwood sulfate lignin[D]. Jinan: Qilu University of Technology, 2019.
53	REICHERT E , WINTRINGER R , VOLMER D A , et al. Electro-catalytic oxidative cleavage of lignin in a protic ionic liquid[J]. Physical Chemistry Chemical Physics, 2012, 14 (15): 5214- 5221. doi: 10.1039/c2cp23596j
54	朱媛. 催化氢解与酶解/氧化降解木质素制备单酚类化合物[D]. 广州: 华南理工大学, 2017.
	ZHU Y. Preparation of monophenols by catalytic hydrogenolysis and enzymatic/oxidative degradation of lignin[D]. Guangzhou: South China University of Technology, 2017.
55	崔晓敏, 梁继东, 霍欣, 等. 电化学氧化与生物法联合降解木质素的影响因素[J]. 环境工程学报, 2016, 10 (5): 2407- 2412.
	CUI X M , LIANG J D , HUO X , et al. Influencing factors of lignin degradation by combination of electrochemical oxidation and biodegradation[J]. Chinese Journal of Environmental Engineering, 2016, 10 (5): 2407- 2412.
56	SHIRAISHI T , SANNAMI Y , KAMITAKAHARA H , et al. Comparison of a series of laccase mediators in the electro-oxidation reactions of non-phenolic lignin model compounds[J]. Electrochimica Acta, 2013, 106, 440- 446.
57	李敏, 张得伟, 王瑞凯, 等. 用于木质素解聚反应的光催化材料应用研究进展[J]. 山东化工, 2019, 48 (10): 65- 69. doi: 10.3969/j.issn.1008-021X.2019.10.024
	LI M , ZHANG D W , WANG R K , et al. Research progress of catalytic materials in photocatalytic depolymerization of lignin[J]. Shandong Chemical Industry, 2019, 48 (10): 65- 69. doi: 10.3969/j.issn.1008-021X.2019.10.024
58	ZHENG M, HUANG Y, ZHAN L W, et al. Visible-light-induced C-C bond cleavage of lignin model compounds with cyanobenziodoxolone[J/OL]. Tetrahedron Letters, 2020, 61(42): 1-6[2020-09-15]. https://doi.org/10.1016/j.tetlet.2020.152420.
59	WANG J Q , YAN C , ZHU L Y , et al. Solar binary chemical depolymerization of lignin for efficient production of small molecules and hydrogen[J]. Bioresource Technology, 2019, 272, 249- 258. doi: 10.1016/j.biortech.2018.10.032
60	LI T F , MO J Y , WEEKES D M , et al. Photoelectrochemical decomposition of lignin model compound on a BiVO₄ photoanode[J]. ChemSusChem, 2020, 13 (14): 3622- 3626. doi: 10.1002/cssc.202001134

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Research Progress in Electrochemically Catalyzed Depolymerization of Lignin

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