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Progress in Chemistry 2021, Vol. 33 Issue (2): 303-317 DOI: 10.7536/PC200524 Previous Articles   Next Articles

• Review •

Lignin: A Potential Source of Biomass-Based Catalysts

Xiangyun Chen1, Bing Yuan1,*(), Fengli Yu1, Congxia Xie1, Shitao Yu2   

  1. 1 State Key Laboratory Base of Eco-Chemical Engineering, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology,Qingdao 266042, China
    2 College of Chemical Engineering, Qingdao University of Science and Technology,Qingdao 266042, China
  • Received: Revised: Online: Published:
  • Contact: Bing Yuan
  • About author:
    * Corresponding author e-mail:
  • Supported by:
    National Natural Science Foundation of China(31870554); National Natural Science Foundation of China(31470595); Shandong Key R&D Plan(Public Welfare Special Project)(2017GGX40105); Taishan Scholars Projects of Shandong(ts201511033)
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Lignin is one of the richest natural biomass, and more importantly, it is the only renewable resource containing aromatic structures in nature reserves. However, a large part of this resource are abandoned by far due to the complex structure, which makes the effective utilization of lignin quite difficult. It is well known that lignin can be transformed into a series of substitutes for petrochemical products via some redox processes. Beyond that, not only the oxygen-rich functional groups in lignin structure, but also the sulfur element introduced during the pulping process can provide effective active sites, making lignin resource a promising substrate of various catalysts. In this paper, following a brief summary of the species and structural characteristics of lignin resource, the applications of lignin-based catalysts in acid-base catalytic reactions, such as hydrolysis of biomass platform compounds, electrocatalysis reactions,oxidation-reduction reactions catalyzed by supported metal nanoparticles are summarized according to the catalytic mechanism and modification methods of lignin. The effects of lignin types, preparation or activation conditions on the performance of lignin-based catalytic materials are also discussed in detail. Besides, the current problems and future develop prospects of the development of lignin-based catalysts are also indicated.

Contents

1 Introduction

2 Application of lignin-based catalysts in acid-base catalytic systems

2.1 Lignosulfonic acid and its salts catalysts

2.2 Lignin-based acidic catalysts with hydroxyl groups as active groups

2.3 Lignin-based acidic resin catalysts

2.4 Lignin carbon-based acidic catalysts

2.5 Lignin-based acid-base synergistic catalysts

3 Application of lignin-based catalysts in redox catalytic systems

3.1 Lignin-based redox catalysts with quinone/ hydroquinone(Q/HQ) groups as active groups

3.2 Lignin supporting or stable redox catalysts

3.3 Lignin carbon-based redox catalysts

4 Conclusion and outlook

Key words: lignin, catalyst, acid-base catalyzed reaction, redox catalyzed reaction
Fig. 1 Schematic illustration of source and structural unit of natural lignin
Fig. 2 A craft summary for separation of lignin from lignocellulose
Table 1 Application of lignin-based acid catalyst prepared by ion exchange method
Catalyst Raw materials Preparation method Application ref
LSA SLS Ion exchange through an acid resin column Conversion of inulin and fructose into 5-HMF 54
Lignin based solid acid KL Stiring sulfuryl chloride with raw materials Esterification and hydration reaction 56
LSA SLS Ion exchange Conversion of xylose into 5-HMF 53
LSA SLS Ion exchange Synthesis of lignin-derived bisphenols 55
LSA SLS Ion exchange Multicomponent reactions 52
LSA Sulfomethylated lignin Ion exchange Wood furfurylation 57
Fig. 3 Solid catalysts prepared from lignosulfonate by ion exchange[58]
Table 2 Catalytic applications of lignin carbon-based solid acids
Raw
materials 		Synthesis conditions BET surface
area, m2·g-1 		Acid density, mmol·g-1 Reactions ref
Total acid —SO3H —COOH —OH
Enzymatic hydrolyzed residues(EHR) Pyrolysis carbonization:
N2, 400 ℃, 2 h
Sulfonation: H2SO4, 150 ℃, 10 h 		1.88 4.62 0.62 - - Transformation of cellulose into nanofibers and platform chemicals 66
Residual lignin Sulfonation: N2, H2SO4,
150 ℃, 1 h 		4.7 1.71 0.68 - - Esterification of
acidified soybean soapstocks 		67
SLS Sulfonation: H2SO4,
150~175 ℃, 0.5 h
(Sulfonation: 20% fuming H2SO4, 150~175 ℃, 12 h) 		3.19
(2.18) 		4.64
(5.90) 		0.96
(1.24) 		3.36
(3.66) 		0.92
(1.04) 		Esterification of
cyclohexanecarboxylic acid with anhydrous ethanol 		68
SLS Pyrolysis carbonization:
N2, 250 ℃, 6 h
Sulfonation: H2SO4, 130 ℃, 10 h
Oxidation: H2O2, 50 ℃, 1.5 h 		- 4.78 0.68 - - Hydrolysis of
hemicellulose in
corncob 		69
AL Pyrolysis carbonization:
Ar, 450 ℃, 1 h 		- 0.13 0.08 0.02 0.02 Hydrolysis of cellulose and woody biomass 70
Dealkali lignin(DAL) Hydrothermal carbonization: 265 ℃
Sulfonation: H2SO4, 150 ℃, 1 h 		- 1.15 0.74 0.27 0.83 Dehydration of inulin into HMF 71,72
DAL Carbonization:
supercritical ethanol,
260 ℃, 8.4 MPa, 20 h
Sulfonation: H2SO4, 150 ℃, 10 h 		113.1 5.05 1.41 - - Esterification of oleic acid, esterification and transesterification of plantoils 73
Kraft lignin Chemical activation: H3PO4, 1 h
Pyrolysis carbonization:
N2, 400 ℃, 1 h
Sulfonation: H2SO4, 200 ℃, 2 h 		54.8 1.30 - - - Esterification of oleic acid and conversion of non-pretreated Jatropha oil to biodiesel 74
AL Electrospun: NaOH
Pyrolysis carbonization:
N2, 900 ℃, 0.5 h
Sulfonation: H2SO4, 150 ℃, 20 h
Hydrothermal treated:
150 ℃, 5 atm 		475 0.88 0.56 - - Hydrolysis of highly crystalline rice straw cellulose 75
AL Impregnation: KOH
Pyrolysis carbonization:N2, 400 ℃, 1 h; 600 ℃, 2 h
Sulfonation: N2, H2SO4,
150 ℃, 10 h 		524.9 - 0.40 - - Hydrolysis of
pretreated rice straw 		76
Enzymatic hydrolysis lignin residue Impregnation: FeCl3, 5 h
Pyrolysis carbonization:
N2, 400 ℃, 1 h
Sulfonation: N2, H2SO4,
150 ℃, 10 h 		234.61
5.65(without impregnation) 		1.95
1.42(without impregnation) 		0.77
0.65(without impregnation) 		- - Dehydration of fructose into
5-HMF 		77
SLS Pretreatment: ice-templating
Pyrolysis carbonization:N2, 450 ℃,
1 hIon exchange: H2SO4 		122 3.49 1.21 - - Acetalization of
glycerol to bio-additives 		78
AL Polymerization and dispersion(F123 as template agent);Pyrolysis carbonization:N2, 900 ℃, 3 h
Sulfonation: H2SO4, 180 ℃, 12 h 		156 - 1.82 - - Hydrolysis of bagasse cellulose 79
Kraft lignin Impregnation: NaOH, F123 Pyrolysis carbonization: N2, 900 ℃, 3 h;Sulfonation: H2SO4, 180 ℃, 12 h 262 - 0.65 - - Fructose dehydration to 5-HMF 80
Fig. 4 dTG-MS spectra of SLS[88]
Fig. 5 (a) Possible schematic diagram of sulfonated carbonaceous solid acids decomposition[90];(b) Deactivation of sulfonated carbonaceous solid acids by adsorbed alcohols[91]
Fig. 6 Chemical structure of activated carbons[84]
Fig. 7 Reasonable structure of Hf-LigS and possible mechanism of 5-HMF reduction catalyzed by Hf-LigS[103]
Table 3 Lignin modified electrode for electrocatalytic reaction
Lignin type Electrode type Electrocatalytic reaction ref
AL Polycrystalline gold electrodes Ascorbic acid oxidation 106
SLS Glassy carbon(GC) electrode Reduction of nitrite 107
SL1 and SL2a GC Oxidation of reduced nicotinamide adenine dinucleotide(NADH) 50
Hydrolytic lignin(HL) Gold electrode Oxidation of NADH 108
Lignin oxidation Carbon paste electrodes Oxidation of dopamine and ascorbic acid; Reduction of nitrite and iodate 109
AL GC Oxidation of histamine 110
PPy/SL and PEDOT/SLb GC Electrooxidation of hydrazine 111
Ni-SL GC Oxidation of methanol 112
Manganese lignosulfonates GC Oxidation of hydrogen peroxide 113
ZCFc GC Oxidation of hydroquinone(HQ), CC, and resorcinol(RS) 114
Lignin GC Oxidation of caffeine 115
Scheme 1 Electrochemical activity of lignin and lignin-derived ruthenium mediated reduction of acidic nitrite[50,107]
Fig. 8 Lignin cross-links to prepare effective carriers and couple active centers[123?~125]
Scheme 2 Mechanism of preparation of metal NPs by lignin
Table 4 Preparation and application of lignin carbon-based redox catalyst
Raw
materials 		Catalysts Activator/dopant Processing
temperature,℃ 		BET surface
area, m2·g-1 		Reactions ref
AL N-S-C 900 - 900 486 Oxygen reduction reaction(ORR) 151
Lignin Lignin derived multi-doped(N, S, Cl) carbon materials NaCl/ZnCl2 1000 1289 ORR 152
Low-sulfur lignin Sulfur-nitrogen co-doped porous biocarbon catalyst NaCl/ZnCl2 1000 1218.68 Electrochemical CO2 reduction
reaction(ECRR) 		153
Lignin Pt/Lg-CDs-800 - 800 - Methanol electro-oxidation reaction(MOR) 154
Kraft lignin Pd-activated carbon catalysts H3PO4 900 1248 Suzuki-Miyaura cross-coupling
reaction and hydrogenation 		155
Eucalyptus lignin High-Performance Magnetic Activated Carbon KOH 800 2875 Magnetic activated carbons(MACE) 156
MACE High-Performance Magnetic Activated Carbon-NiMo Supports KOH 800 2875 Hydrodeoxygenation(HDO) 157
SLS Co3S4/C
NiS/C
MoS2/C
Co3Mo6S/C
NiMoS3/C
S/C 		Mg(OH)2 700 379
560
630
485
412
571 		HDO 158
DAL Mo-DAL - 800 19.7 Hydrogen production from formic acid 159
Lignin A single-atom cobalt over nitrogen-doped carbon(Co SAs/N@C) Zn(OAC)2·2H2O 900 - Transformation of 5-HMF and furfural into the carboxylic acids. 160
AL Co-Mn/N@C Dicyandiamide 800 - Aerobic oxidation of 5-
hydroxymethylfurfural to 2,5-
furandicarboxylic acid 		161
AL M SAs-N@C, M=Fe, Co, Ni, Cu Dicyandiamide
Zn(OAC)2·2H2O 		1000 - Oxidative esterification of primary alcohols 162
SLS N,S-doped hierarchical porous catalysts(Co-Nx/Sy-C) Thiourea 900 314 Peroxymonosulfate-based oxidative
degradation and borohydride-
mediated reductive amination of
several pollutants 		163
Fig. 9 Coordination directed assembly of metal-lignin complexes: Bottom-up strategy to synthesize atom-dispersed Co SAs/N@C catalyst and its use for 2,5-furandicarboxylic acid(FDCA) conversion[160]
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