Biomass Chemical Engineering ›› 2020, Vol. 54 ›› Issue (2): 40-50.doi: 10.3969/j.issn.1673-5854.2020.02.007
• Review Comment • Previous Articles Next Articles
Qian YANG,Guifeng LIU,Guomin WU,Zhenwu KONG*()
Received:
2019-05-13
Online:
2020-03-30
Published:
2020-04-16
Contact:
Zhenwu KONG
E-mail:kongzwlhs@163.com
Supported by:
CLC Number:
Qian YANG,Guifeng LIU,Guomin WU,Zhenwu KONG. Research Progress of Lignin Chemical Degradation and Its Applications in Polymer Materials[J]. Biomass Chemical Engineering, 2020, 54(2): 40-50.
Table 1
The relative content of the basic structural elements of lignin from different materials"
结构单元 constitutional unit | 结构单元质量分数mass fraction of structural units/% | ||
针叶木softwood | 阔叶木hardwood | 草本植物herbage | |
对羟基苯基型p-hydroxyphenyl(H) | 0.5~3.5 | 微量trace | 10~25 |
愈创木基型guaiacyl(G) | 90~95 | 25~50 | 25~50 |
紫丁香基型syringyl(S) | 0~1 | 50~75 | 25~50 |
Table 3
Physicochemical properties of lignin"
木质素种类 lignin | 元素组成 element composition | 官能团 functional group | 相对分子质量 relative molecular weight | 溶解性 solubility |
木质素磺酸盐 lignin sulfonate | C、H、O、S | OH、OCH3、SO3H | 1000~61000 | 水、乙二醇、二甲基亚砜等 water, DMSO, ethylene glycol, etc |
硫酸盐木质素 kraft lignin | C、H、O、S | OH、OCH3、SH | 1000~15000 | 碱性溶液(pH>10)、丙酮、二甲酰胺等 alkaline solutions(pH>10), dimethyl amide, acetone, etc. |
碱木质素alkali lignin | C、H、O | OH、OCH3 | 800~3000 | 碱性溶液alkaline solutions |
有机溶剂可溶木质素 organosolv lignin | C、H、O | OH、OCH3、COOR | 500~5000 | 稀碱性溶液、有机溶剂 dilute alkaline solutions,organic solvents |
Table 4
The yield and product from nitrobenzene oxidation of different lignin"
植物种类 floristics | 氧化产物得率yield of oxidation products/% | 芳香醛物质的量分数fraction of aromatic aldehydes/% | |||||
香草醛 vanillin | 紫丁香醛 syringaldehyde | 对羟基苯甲醛 p-hydroxy benzaldehyde | 香草醛 vanillin | 紫丁香醛 syringaldehyde | 对羟基苯甲醛 p-hydroxy benzaldehyde | ||
云杉spruce | 33.9 | 微量trace | 微量trace | 100.0 | 0 | 0 | |
桦树birch | 14.1 | 34.2 | — | 29.4 | 70.6 | 0 | |
稻草rice straw | 16.0 | 6.8 | 11.7 | 43.5 | 17.4 | 39.1 | |
枫香树liquidambar formosana hance | 10.3 | 23.4 | — | 30.3 | 69.7 | 0 | |
毛竹 phyllostachys pubescens | 19.0 | 25.7 | 7.9 | 35.7 | 50.0 | 14.3 | |
麦草wheat straw | 7.0 | 6.2 | 1.5 | 50.0 | 35.0 | 15.0 |
1 | FIGUEIREDO P , LINTINEN K , HIRVONEN J T , et al. Properties and chemical modifications of lignin:Towards lignin-based nanomaterials for biomedical applications[J]. Progress in Materials Science, 2018, 93, 233- 269. |
2 |
ROOPAN S M . An overview of natural renewable bio-polymer lignin towards nano and biotechnological applications[J]. International Journal of Biological Macromolecules, 2017, 103, 508- 514.
doi: 10.1016/j.ijbiomac.2017.05.103 |
3 |
LAURICHESSE S , AVÉROUS L . Chemical modification of lignins:Towards biobased polymers[J]. Progress Polymer Science, 2014, 39 (7): 1266- 1290.
doi: 10.1016/j.progpolymsci.2013.11.004 |
4 |
ZAKZESKI J , BRUIJNINCX P C A , JONGERIUS A L , et al. The catalytic valorization of lignin for the production of renewable chemicals[J]. Chemical Reviews, 2010, 110 (6): 3552- 3599.
doi: 10.1021/cr900354u |
5 |
DE S , SAHA B , LUQUE R . Hydrodeoxygenation processes:Advances on catalytic transformations of biomass-derived platform chemicals into hydrocarbon fuels[J]. Bioresource Technology, 2015, 178, 108- 118.
doi: 10.1016/j.biortech.2014.09.065 |
6 |
YANG X J , FENG M Q , CHOI J S , et al. Depolymerization of corn stover lignin with bulk molybdenum carbide catalysts[J]. Fuel, 2019, 244, 528- 535.
doi: 10.1016/j.fuel.2019.02.023 |
7 | DESSBESELL L, PALEOLOGOU M, LEITCH M, et al.Global lignin supply overview and kraft lignin potential as an alternative for petroleum-based polymers.Renewable and Sustainable Energy Reviews, 2020, 123: 109768. |
8 | AN L L , SI C L , WANG J H , et al. Enhancing the solubility and antioxidant activity of high-molecular-weight lignin by moderate depolymerization via in situ ethanol/acid catalysis[J]. Industrial Crops & Products, 2019, 128, 177- 185. |
9 |
ZHAO X H , ZHANG Y J , HU H Y , et al. Effect of mechanical activation on structure changes and reactivity in further chemical modification of lignin[J]. International Journal of Biological Macromolecules, 2016, 91, 1081- 1089.
doi: 10.1016/j.ijbiomac.2016.06.074 |
10 | CHATEL G , ROGERS R D . Review:Oxidation of lignin using ionic liquids-an innovative strategy to produce renewable chemicals[J]. ACS Sustainable Chemistry & Engineering, 2013, 2 (3): 322- 339. |
11 |
SUN Y , QIU X , LIU Y . Chemical reactivity of alkali lignin modified with laccase[J]. Biomass and Bioenergy, 2013, 55, 198- 204.
doi: 10.1016/j.biombioe.2013.02.006 |
12 |
ZHAO X H , ZHANG Y J , HU H Y , et al. Effect of mechanical activation on structure changes and reactivity in further chemical modification of lignin[J]. International Journal of Biological Macromolecules, 2016, 91, 1081- 1089.
doi: 10.1016/j.ijbiomac.2016.06.074 |
13 |
WANG J , CAO F , SU E , et al. Improvement of animal feed additives of Ginkgo leaves through solid-state fermentation using Aspergillus niger[J]. International Journal of Biological Sciences, 2018, 14 (7): 736- 747.
doi: 10.7150/ijbs.24523 |
14 |
CHIO C L , SAIN M , QIN W S . Lignin utilization:A review of lignin depolymerization from various aspects[J]. Renewable and Sustainable Energy Reviews, 2019, 107, 232- 249.
doi: 10.1016/j.rser.2019.03.008 |
15 |
NANAYAKKARA S , PATTI A F , SAITO K . Chemical depolymerization of lignin involving the redistribution mechanism with phenols and repolymerization of depolymerized products[J]. Green Chemistry, 2014, 16 (4): 1897- 1903.
doi: 10.1039/C3GC41708E |
16 |
MA J F , YANG H Y , KUN W , et al. Structural modification of hemicelluloses and lignin based on the biorefinery process with white-rot fungal[J]. Carbohydrate Polymers, 2016, 153, 7- 13.
doi: 10.1016/j.carbpol.2016.07.085 |
17 |
付伟, 廖祥儒, 王俊峰, 等. 植物体内的木质素[J]. 生物学通报, 2004, 39 (2): 12- 14.
doi: 10.3969/j.issn.0006-3193.2004.02.004 |
18 | 邱学青, 欧阳新平, 杨东杰. 工业木质素高效利用的改性理论与技术[M]. 北京: 科学出版社, 2013: 1- 3. |
19 | 蒋挺大. 木质素[M]. 北京: 化学工业出版社, 2009: 1- 4. |
20 | HATAKEYAMA H , HATAKEYAMA T . Lignin structure, properties, and applications[J]. Advances in Polymer Science, 2010, 232, 1- 63. |
21 | 黄进, 付时雨. 木质素化学及改性材料[M]. 北京: 化学工业出版社, 2014: 26- 71. |
22 |
EI MANSOURI N E , SALVADÓ J . Analytical methods for determining functional groups in various technical lignins[J]. Industrial Crops and Products, 2007, 26 (2): 116- 124.
doi: 10.1016/j.indcrop.2007.02.006 |
23 |
KUN D , PUKÁNSZKY B . Polymer/lignin blends:Interactions, properties, applications[J]. European Polymer Journal, 2017, 93, 618- 641.
doi: 10.1016/j.eurpolymj.2017.04.035 |
24 |
ESPINOZA-ACOSTA J L , TORRES-CHÁVEZ P I , OLMEDO-MARTÍNEZ J L , et al. Lignin in storage and renewable energy applications:A review[J]. Journal of Energy Chemistry, 2018, 27 (5): 1422- 1438.
doi: 10.1016/j.jechem.2018.02.015 |
25 |
DOHERTY W O S , MOUSAVIOUN P , FELLOWS C M . Value-adding to cellulosic ethanol:Lignin polymers[J]. Industrial Crops and Products, 2011, 33, 259- 276.
doi: 10.1016/j.indcrop.2010.10.022 |
26 |
MATSUSHITA Y . Conversion of technical lignins to functional materials with retained polymeric properties[J]. Journal of Wood Science, 2015, 61 (3): 230- 250.
doi: 10.1007/s10086-015-1470-2 |
27 |
ZAKZESKI J , BRUIJNINCX P C , JONGERIUS A L , et al. The catalytic valorization of lignin for the production of renewable chemicals[J]. Chemical Reviews, 2010, 110 (6): 3552- 3599.
doi: 10.1021/cr900354u |
28 |
TRIBOT A , AMER G , ALIO M A , et al. Wood-lignin:Supply, extraction processes and use as bio-based material[J]. European Polymer Journal, 2019, 112, 228- 240.
doi: 10.1016/j.eurpolymj.2019.01.007 |
29 |
GALKIN M V , SAMEC J S . Lignin valorization through catalytic lignocellulose fractionation:A fundamental platform for the future biorefinery[J]. ChemSusChem, 2016, 9 (13): 1544- 1558.
doi: 10.1002/cssc.201600237 |
30 | VISHTAL A , KRASLAWSKI A . Challenges in industrial applications of technical lignins[J]. BioResources, 2011, 6 (3): 3547- 3568. |
31 |
AZADI P , INDERWILDI O R , FAMOOD R , et al. Liquid fuels, hydrogen and chemicals from lignin:A critical review[J]. Renewable and Sustainable Energy Reviews, 2013, 21, 506- 523.
doi: 10.1016/j.rser.2012.12.022 |
32 | ERDOCIA X , TOLEDANO A , CORCUERA M A , et al. Organosolv black liquor hydrolysis to obtain low molecular weight phenolic compounds[J]. Chemical Engineer Transform, 2012, 29, 535- 540. |
33 |
HUANG S H , MAHMOOD N , TYMCHYSHYN M , et al. Reductive depolymerization of Kraft lignin for chemicals and fuels using formic acid as an in-situ hydrogen source[J]. Bioresource Technology, 2014, 171, 95- 102.
doi: 10.1016/j.biortech.2014.08.045 |
34 | DORRESTIJN E , LAARHOVEN L J J , ARENDS L W C E , et al. The occurrence and reactivity of phenoxyl linkages in lignin and low rank coal[J]. Journal of Analytical and Applied Pyrolysis, 2000, 54 (1/2): 153- 192. |
35 | XU C B , FERDOSIAN F . Conversion of lignin into bio-based chemicals and materials:Chapter 3 degradation of lignin by depolymerization[J]. Green Chemistry and Sustainable Technology, 2017, 35, 1- 20. |
36 | 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. |
37 |
GALKIN M V , SMIT A T , SUBBOTINA E , et al. Hydrogen-free catalytic fractionation of woody biomass[J]. ChemSusChem, 2016, 9 (23): 3280- 3287.
doi: 10.1002/cssc.201600648 |
38 |
ZHANG S M , SHU L , LIU L , et al. Degradation on hydrogenolysis of soda lignin using CuO/SO42-/ZrO2 as catalyst[J]. Industrial Crops and Products, 2015, 77, 451- 457.
doi: 10.1016/j.indcrop.2015.07.039 |
39 |
HAKONEN K J , GONZÁLEZ ESCOBEDO J L , MERIÖ-TALVIO H , et al. Ethanol organosolv lignin depolymerization with hydrogen over a Pd/C catalyst[J]. ChemistrySelect, 2018, 3 (6): 1761- 1771.
doi: 10.1002/slct.201702701 |
40 |
LI W Z , DOU X M , ZHU C Z , et al. Production of liquefied fuel from depolymerization of Kraft lignin over a novel modified nickel/H-beta catalyst[J]. Bioresource Technology, 2018, 269, 346- 354.
doi: 10.1016/j.biortech.2018.08.125 |
41 |
GÓMEZ-MONEDERO B , PILAR RUIZ M , BIMBELA F , et al. Selective depolymerization of industrial lignin-containing stillage obtained from cellulosic bioethanol processing[J]. Fuel Processing Technology, 2018, 173, 165- 172.
doi: 10.1016/j.fuproc.2018.01.021 |
42 |
LIU X D , JIANG Z C , FENG S S , et al. Catalytic depolymerization of organosolv lignin to phenolic monomers and low molecular weight oligomers[J]. Fuel, 2019, 244, 247- 257.
doi: 10.1016/j.fuel.2019.01.117 |
43 |
SHU R Y , XU Y , MA L L , et al. Controllable production of guaiacols and phenols from lignin depolymerization using Pd/C catalyst cooperated with metal chloride[J]. Chemical Engineering Journal, 2018, 338, 457- 464.
doi: 10.1016/j.cej.2018.01.002 |
44 |
YUAN Z S , TYMCHYSHYN M , XU C B . Reductive depolymerization of Kraft and organosolv lignin in supercritical acetone for chemicals and materials[J]. ChemCatChem, 2016, 8 (11): 1968- 1976.
doi: 10.1002/cctc.201600187 |
45 |
ZHOU M H , SHARMA B K , LI J , et al. Catalytic valorization of lignin to liquid fuels over solid acid catalyst assisted by microwave heating[J]. Fuel, 2019, 239, 239- 244.
doi: 10.1016/j.fuel.2018.10.144 |
46 |
RAHIMI A , ULBRICH A , COON J J , et al. Formic-acid-induced depolymerization of oxidized lignin to aromatics[J]. Nature, 2014, 515 (7526): 249- 252.
doi: 10.1038/nature13867 |
47 | KLEINERT M , BARTH T . Phenols from lignin[J]. Chemical Engineering & Technology, 2010, 31 (5): 736- 745. |
48 |
HU J , ZHANG S H , RUI X , et al. Catalytic transfer hydrogenolysis of lignin into monophenols over platinum-rhenium supported on titanium dioxide using isopropanol as in situ hydrogen source[J]. Bioresource Technology, 2019, 279, 228- 233.
doi: 10.1016/j.biortech.2019.01.132 |
49 |
HUANG S H , MAHMOOD N , ZHANG Y S , et al. Reductive de-polymerization of Kraft lignin with formic acid at low temperatures using inexpensive supported Ni-based catalysts[J]. Fuel, 2017, 209, 579- 586.
doi: 10.1016/j.fuel.2017.08.031 |
50 | FGHALI E , CARROT G , THUÉRY P , et al. Convergent reductive depolymerization of wood lignin to isolated phenol derivatives by metal-free catalytic hydrosilylation[J]. Energy & Environmental Science, 2015, 8 (9): 2734- 2743. |
51 |
MONSIGNY L , FEGHALI E , BERTHET J C , et al. Efficient reductive depolymerization of hardwood and softwood lignins with Brookhart's iridium(Ⅲ) catalyst and hydrosilanes[J]. Green Chemistry, 2018, 20 (9): 1981- 1986.
doi: 10.1039/C7GC03743K |
52 |
WU Z , ZHAO X X , ZHANG J , et al. Ethanol/1, 4-dioxane/formic acid as synergistic solvents for the conversion of lignin into high-value added phenolic monomers[J]. Bioresource Technology, 2019, 278, 187- 194.
doi: 10.1016/j.biortech.2019.01.082 |
53 |
MA R , 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 |
54 |
CHAN F D , NGUYEN K L , WALLIS A F A . Contribution of lignin sub-structures to nitrobenzene oxidation products[J]. Journal of Wood Chemistry and Technology, 1995, 15 (3): 329- 347.
doi: 10.1080/02773819508009514 |
55 |
TARABAN-KO V E , KOROPATCHINSKAYA N V , KUZNETSOV B V , et al. Influence of lignin origin on the efficiency of the catalytic oxidation of lignin into vanillin and syringaldehyde[J]. Russian Chemical Bulletin, 1995, 44 (2): 367- 371.
doi: 10.1007/BF00702154 |
56 |
VILLAR J C , CAPEROS A , GARCÍA O F . Oxidation of hardwood Kraft-lignin to phenolic derivatives, nitrobenzene and copper oxide as oxidants[J]. Journal of Wood Chemistry and Technology, 1997, 17 (3): 259- 285.
doi: 10.1080/02773819708003131 |
57 | MASINGALE M P , ALVES E F , BOSE S K , et al. An oxidant to replace nitrobenzene in lignin analysis[J]. BioResources, 2009, 4 (3): 1139- 1146. |
58 |
HANSON S K , BAKER R T . Knocking on wood:Base metal complexes as catalysts for selective oxidation of lignin models and extracts[J]. Accounts of Chemical Research, 2015, 48 (7): 2037- 2048.
doi: 10.1021/acs.accounts.5b00104 |
59 | HDIDOU L , KHALLOUK K , MANOUN B , et al. Synthesis of CoFeO mixed oxide via alginate gelation process as an efficient heterogeneous catalyst for lignin depolymerization in water[J]. Catalysis Science & Technology, 2018, 8 (21): 5445- 5453. |
60 | ZHANG Y Q , FATEHI P . Periodate oxidation of carbohydrate-enriched hydrolysis lignin and its application as coagulant for aluminum oxide suspension[J]. Industrial Crops & Products, 2019, 130, 81- 95. |
61 |
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 |
62 |
HAO Z K , LI S Y , SUN J R , et al. Efficient visible-light-driven depolymerization of oxidized lignin to aromatics catalyzed by an iridium complex immobilized on mesocellular silica foams[J]. Applied Catalysis B:Environmental, 2018, 237, 366- 372.
doi: 10.1016/j.apcatb.2018.05.072 |
63 |
MAZARJI M , ALVARADO-MORALES M , TSAPEKOS P , et al. Graphene based ZnO nanoparticles to depolymerize lignin-rich residues via UV/iodide process[J]. Environment International, 2019, 125, 172- 183.
doi: 10.1016/j.envint.2018.12.062 |
64 |
MAGALLANES G , KÄRKÄS M D , BOSQUE I , et al. Selective C-O bond cleavage of lignin systems and polymers enabled by sequential palladium-catalyzed aerobic oxidation and visible-light photoredox catalysis[J]. ACS Catalysis, 2019, 9, 2252- 2260.
doi: 10.1021/acscatal.8b04172 |
65 | LONG J X , XU Y , WANG T J , et al. Hydrothermal depolymerization of lignin:Understanding the structural evolution[J]. BioResources, 2014, 9 (4): 7162- 7175. |
66 | YUAN Z S , CHENG S N , LEITCH M , et al. Hydrolytic degradation of alkaline lignin in hot-compressed water and ethanol[J]. Bioresource Technology, 2010, 101 (23): 9308- 9313. |
67 |
MAHMOOD N , YUAN Z S , SCHMIDT J , et al. Hydrolytic depolymerization of hydrolysis lignin:Effects of catalyst and solvents[J]. Bioresource Technology, 2015, 190, 416- 419.
doi: 10.1016/j.biortech.2015.04.074 |
68 |
DEEPA A K , DHEPE P L . Lignin depolymerization into aromatic monomers over solid acid catalysts[J]. ACS Catalysis, 2015, 5 (1): 365- 379.
doi: 10.1021/cs501371q |
69 |
YOSHIKAWA T , YAGI T , SHINOHARA S , et al. Production of phenols from lignin via depolymerization and catalytic cracking[J]. Fuel Processing Technology, 2013, 108, 69- 75.
doi: 10.1016/j.fuproc.2012.05.003 |
70 | OKUDA K , UMETSU M , TAKAMI S , et al. Disassembly of lignin and chemical recovery rapid depolymerization of lignin without char formation in water-phenol mixtures[J]. Fuel Processing Technology, 2004, 85 (8): 803- 813. |
71 |
ZHANG L B , ZHENG W X , WANG Z M , et al. Efficient degradation of lignin in raw wood via pretreatment with heteropoly acids in γ-valerolactone/water[J]. Bioresource Technology, 2018, 261, 70- 75.
doi: 10.1016/j.biortech.2018.03.141 |
72 | CAI Z P , LI Y W , HE H Y , et al. Catalytic depolymerization of organosolv lignin in a novel water/oil emulsion reactor:Lignin as the self-surfactant[J]. Industrial & Engineering Chemistry Research, 2015, 54 (46): 11501- 11510. |
73 | DAS A , RAHIMI A , UIBRICH A , et al. Lignin conversion to low-molecular-weight aromatics via an aerobic oxidation-hydrolysis sequence:comparison of different lignin sources[J]. ACS Sustainable Chemistry & Engineering, 2018, 6 (3): 3367- 3374. |
74 | AN L L , SI C L , WANG G H , et al. Enhancing the solubility and antioxidant activity of high-molecular-weight lignin by moderate depolymerization via in situ ethanol/acid catalysis[J]. Industrial Crops & Products, 2019, 128, 177- 185. |
75 |
PRADO R , ERDOCIA X , LABIDI J . Study of the influence of reutilization ionic liquid on lignin extraction[J]. Journal of Cleaner Production, 2016, 111, 125- 132.
doi: 10.1016/j.jclepro.2015.04.003 |
76 |
MOGHADDAM L , ZHANG Z Y , WELLARD R M , et al. Characterization of lignins isolated from sugarcane bagasse pretreated with acidified ethylene glycol and ionic liquids[J]. Biomass and Bioenergy, 2014, 70, 498- 512.
doi: 10.1016/j.biombioe.2014.07.030 |
77 | XUE L Y , YAN L C , CUI Y H , et al. Degradation of lignin in ionic liquid with HCl as catalyst[J]. Environmental Progress & Sustainable Energy, 2016, 35 (3): 809- 814. |
78 | TIAN J Y , FU S Y , LUCIA L A . Ionic liquid-based molecular oxygen oxidation of eucalyptus Kraft lignin to obtain a suite of monomeric aromatic by-products[J]. Journal of Wood Chemistry and Technology, 2015, 35 (4): 280- 290. |
79 |
NINOMIYA K , OCHIAI K , EGUCHI M , et at . Oxidative depolymerization potential of biorefinery lignin obtained by ionic liquid pretreatment and subsequent enzymatic saccharification of eucalyptus[J]. Industrial Crops and Products, 2018, 111, 457- 461.
doi: 10.1016/j.indcrop.2017.10.056 |
80 | ZHANG S M , LIU L , FANG G Z , et al. Hydrogenolysis and activation of soda lignin using[BMIM]Cl as a catalyst and solvent[J]. Polymers, 2017, 9 (7): 279- 290. |
81 |
TOLESA L D , GUPTA B S , LEE M J . Degradation of lignin with aqueous ammonium-based ionic liquid solutions under milder conditions[J]. New Journal of Chemistry, 2019, 43, 3357- 3365.
doi: 10.1039/C8NJ05185B |
82 | WANG X H , WANG N N , NGUYEN T T , et al. Catalytic depolymerization of lignin in ionic liquid using a continuous flow fixed-bed reaction system[J]. Industrial & Engineering Chemistry Research, 2018, 57, 16995- 17002. |
83 | POLAT Y , STOJANOVSKA E , NEGAWO T , et al. Lignin as an additive for advanced composites[J]. Green Energy and Technology, 2017, 71- 89. |
84 |
PISHNAMAZI M , CASILAGAN S , CLANCY C , et al. Microcrystalline cellulose, lactose and lignin blends:Process mapping of dry granulation via roll compaction[J]. Powder Technology, 2019, 341, 38- 50.
doi: 10.1016/j.powtec.2018.07.003 |
85 | CULEBRAS M , BEAUCAMP A , WANG Y , et al. Biobased structurally compatible polymer blends based on lignin and thermoplastic elastomer polyurethane as carbon fiber precursors[J]. ACS Sustainable Chemistry & Engineering, 2018, 6 (7): 8816- 8825. |
86 | THAKUR V K , THAKUR M K , RAGHAVAN P , et al. Progress in green polymer composites from lignin for multifunctional applications:A review[J]. ACS Sustainable Chemistry & Engineering, 2014, 2 (5): 1072- 1092. |
87 |
FERDOSIAN F , YUAN Z S , ANDERSON M , et al. Synthesis of lignin-based epoxy resins:Optimization of reaction parameters using response surface methodology[J]. RSC Advances, 2014, 4 (60): 31745- 31753.
doi: 10.1039/C4RA03978E |
88 |
JIANG Y , DING D C , ZHAO S , et al. Renewable thermoset polymers based on lignin and carbohydrate derived monomers[J]. Green Chemistry, 2018, 20 (5): 1131- 1138.
doi: 10.1039/C7GC03552G |
89 |
VAN DE PAS D J , TORR K M . Bio-based epoxy resins from deconstructed native softwood lignin[J]. Biomacromolecules, 2017, 18 (8): 2640- 2648.
doi: 10.1021/acs.biomac.7b00767 |
90 |
FERDOSIAN F , ZYUAN Z S , ANDERSON M , et al. Thermal performance and thermal decomposition kinetics of lignin-based epoxy resins[J]. Journal of Analytical and Applied Pyrolysis, 2016, 119, 124- 132.
doi: 10.1016/j.jaap.2016.03.009 |
91 |
FERDOSIAN F , ZHANG Y S , YUAN Z S , et al. Curing kinetics and mechanical properties of bio-based epoxy composites comprising lignin-based epoxy resins[J]. European Polymer Journal, 2016, 82, 153- 165.
doi: 10.1016/j.eurpolymj.2016.07.014 |
92 |
KAIHO A , MAZZARELLA D , SATAKE M , et al. Construction of the di(trimethylolpropane) cross linkage and the phenylnaphthalene structure coupled with selective β-O-4 bond cleavage for synthesizing lignin-based epoxy resins with a controlled glass transition temperature[J]. Green Chemistry, 2016, 18 (24): 6526- 6535.
doi: 10.1039/C6GC02211A |
93 |
YAN L C , CUI Y H , GOU G J , et al. Liquefaction of lignin in hot-compressed water to phenolic feedstock for the synthesis of phenol-formaldehyde resins[J]. Composites Part B:Engineering, 2017, 112, 8- 14.
doi: 10.1016/j.compositesb.2016.10.094 |
94 | MA C , MEI X W , FAN Y M , et al. Oxidative depolymerization of Kraft lignin and its application in the synthesis of lignin-phenol-formaldehyde resin[J]. BioResources, 2018, 13 (1): 1223- 1234. |
95 |
LI B , WANG Y Y , MAHMOOD N , et al. Preparation of bio-based phenol formaldehyde foams using depolymerized hydrolysis lignin[J]. Industrial Crops and Products, 2017, 97, 409- 416.
doi: 10.1016/j.indcrop.2016.12.063 |
96 |
LI J J , ZHANG J Z , ZHANG S F , et al. Alkali lignin depolymerization under eco-friendly and cost-effective NaOH/urea aqueous solution for fast curing bio-based phenolic resin[J]. Industrial Crops and Products, 2018, 120, 25- 33.
doi: 10.1016/j.indcrop.2018.04.027 |
97 |
SOLT P , RÖБIGER B , KONNERTH J , et al. Lignin phenol formaldehyde resoles using base-catalysed depolymerized Kraft lignin[J]. Polymers, 2018, 10 (10): 1162.
doi: 10.3390/polym10101162 |
98 |
MAHMOOD N , YUAN Z S , SCHMIDT J , et al. Depolymerization of lignins and their applications for the preparation of polyols and rigid polyurethane foams:A review[J]. Renewable and Sustainable Energy Reviews, 2016, 60, 317- 329.
doi: 10.1016/j.rser.2016.01.037 |
99 | HATAKEYAMA T , MATSUMOTO Y , ASANO Y , et al. Glass transition of rigid polyurethane foams derived from sodium lignosulfonate mixed with diethylene, triethylene and polyethylene glycols[J]. Thermochimica Acta, 2004, 416 (1/2): 29- 33. |
100 | MAHMOOD N , YUAN Z S , SCHMIDT J , et al. Valorization of hydrolysis lignin for polyols and polyurethane foams[J]. Journal Science Technology Forest Product Processes, 2013, 3 (5): 26- 31. |
101 |
ZHOU W P , CHEN F G , ZHANG H , et al. Preparation of a polyhydric aminated lignin and its use in the preparation of polyurethane film[J]. Journal of Wood Chemistry and Technology, 2017, 37 (5): 323- 333.
doi: 10.1080/02773813.2017.1299185 |
102 | MAHMOOD N , YUAN Z S , SCHMIDT J , et al. Preparation of bio-based rigid polyurethane foam using hydrolytically depolymerized Kraft lignin via direct replacement or oxypropylation[J]. European Polymer Journal, 2015, 68, 1- 9. |
103 | WYOSOCKA K , SZYMONA K , MCDONALD A G , et al. Characterization of thermal and mechanical properties of ligninsulfonate and hydrolysed lignosulfonate-based polyurethane foams[J]. BioResources, 2016, 11 (3): 7355- 7364. |
[1] | Xue LIU,Shujun LI,Shouxin LIU,Jian LI,Zhijun CHEN. Research Progress in Preparation and Functional Application of Lignin-based Nanoparticles [J]. Biomass Chemical Engineering, 2020, 54(5): 53-65. |
[2] | Ruizhen WANG,Liuming SONG,Peng LIU,Kui WANG,Junming XU. Study of Lignin-based Surfactant [J]. Biomass Chemical Engineering, 2020, 54(3): 61-68. |
[3] | Jianan WANG,Ying YI,Yongjun BIAN,Yuanyuan MA,Zhiming LIU. Preparation, Characterization and Adsorption Performance of Hydroxymethylated Lignin/Cellulose Aerogel Particles [J]. Biomass Chemical Engineering, 2020, 54(1): 16-22. |
[4] | Huanhuan MA,Yiling WAN,Lingxiang XIE,Fanrui MENG,Jianbin ZHOU. Structural Characterization and Pyrolysis Characteristics of Apricot Shell Lignin [J]. Biomass Chemical Engineering, 2019, 53(6): 27-32. |
[5] | Jiaxing ZHOU,Zhiming LIU,Xu LI. Effect of Aluminum Hypophosphite Addition on Flame Retardancy of Alkali Lignin Based Polyurethane Foam [J]. Biomass Chemical Engineering, 2019, 53(2): 1-6. |
[6] | Erqiang YIN,Shichao WANG,Hengxue XIANG,Zhe ZHOU,Meifang ZHU. Preparation and Properties of Melt-spun Kraft Hardwood Lignin-based Activated Carbon Fibers [J]. Biomass Chemical Engineering, 2019, 53(2): 26-34. |
[7] | HU Ping, WANG Lifang, JIA Boran, LIU Ying, SHA Xiaoling, REN Shixue. Degradation Performances of Poly(vinylalcohol)/Wheat Straw Alkali Lignin Foaming Material with Formaldehyde Crosslinker [J]. bce, 2018, 52(4): 29-35. |
[8] | GUO Tengfei, GAO Shishuai, WANG Chunpeng. Synthesis and Application of Melamine Urea Formaldehyde Monolithic Resin Modified by Enzymolysis Lignin [J]. bce, 2018, 52(3): 35-39. |
[9] | WANG Shiwei, CHEN Keyu, WANG Qibao. Preparation and Emulsifying Performance of Acid-soluble Aminated Lignin [J]. bce, 2018, 52(2): 1-6. |
[10] | WU Kai, YING Wenjun, ZHENG Zhifeng, SHI Zhengjun, YANG Haiyan, YANG Jing. Effect of Two Kinds of Lignin on Enzymatic Hydrolysis of Cellulose [J]. bce, 2018, 52(2): 29-34. |
[11] | TAN Yang, MA Chunfu. Mechanism Study of Black Liquor Alkali Lignin Pyrolysis by Using TG-FTIR [J]. bce, 2018, 52(2): 35-41. |
[12] | ZHAO Xinkun, LI Helong, SHE Diao, SUN Runcang. Status and Prospect of Lignin Model Compounds Synthesis [J]. bce, 2018, 52(1): 41-52. |
[13] | SONG Yaoguang, LIU Junli, XU Wei, SUN Kang. Research Progress on Synthesis of Lignin-derived Mesoporous Carbon Materials via Template Strategy [J]. bce, 2018, 52(1): 60-68. |
[14] | PENG Feng, FU Genque, WANG Xiaojun, HU Yajie, YUE Panpan. Isolation and Characterization of Water-soluble and Alkali-soluble Lignin from Bagasse [J]. bce, 2017, 51(4): 1-7. |
[15] | ZHANG Cuimei, CUI Xuejing, SUN Yanni, JIANG Ruiyu, ZHAO Jiruo, FENG Ying. Characteristic of Alkali Lignin Filling Natural Rubber [J]. bce, 2017, 51(3): 33-40. |
Viewed | ||||||
Full text |
|
|||||
Abstract |
|
|||||