木质素催化降解液化的研究进展

doi:10.11896/j.issn.1005-023X.2017.05.018

Abstract
Figure/Table
References
Related Citation (15)

Download:

Full Text ( PDF ) (1261KB)
Export: BibTeX | EndNote (RIS)

Abstract Lignin is the second abundant natural organic polymer, only second to cellulose, which is a complex three-dimensional amorphous polymer, consisting of three different monomer units (sinapyl, coniferyl , and p-coumaryl alcohols) linked with various C-C and C-O-C linkages. It is the richest source of renewable aromatic compounds on planet, and harbors great potential for the production of industrially relevant aromatic bulk and fine chemicals. However, its inherent complexity of chemical linkages makes it difficult to achieve selectivity in chemical transformations. In recent years, the research on catalytic degradation liquefaction of lignin has attracted more and more attention. In this paper, the advances in the field of catalytic degradation liquefaction of lignin are reviewed, and the mesoporous solid acid catalysts loaded with metal particles are put forward to be an efficient way for the degradation liquefaction of lignin. Based on the analysis of the size and morphology of lignin molecules in the solution, the matching mesoporous catalysts loaded with acid and metal particles are designed, which can realize the catalytic degradation of lignin in finite channels and restrain the repolymerization of the degradation fragments considerably.

Key words： lignin catalysis degradation liquefaction

Published: 02 May 2018

CLC number:	O469
	TB324

	Service
	E-mail this article
	Add to my bookshelf
	Add to citation manager
	E-mail Alert
	RSS
	Articles by authors
	CUI Yuhu
	WANG Qi
	GOU Guangjun
	JIANG Man
	ZHOU Zuowan
	ZHANG Shengli
	FU Jinli

Cite this article:

CUI Yuhu,WANG Qi,GOU Guangjun, et al. Advances in Catalytic Degradation Liquefaction of Lignin[J]. Materials Reports, 2017, 31(5): 112-116.

URL:

http://www.mater-rep.com/EN/10.11896/j.issn.1005-023X.2017.05.018 OR http://www.mater-rep.com/EN/Y2017/V31/I5/112

1 Amidon T E, Shijie L. Water-based woody biorefinery[J]. Biotechnol Adv,2009,27(5):542.
2 Perlack R D, Wright L L, Turhollow A F, et al. Biomass as feedstock for a bioenergy and bioproducts industry: The technical feasibi-lity of a billion-ton annual supply[R]. Oak Ridge: U.S. Department of Energy,2005.
3 Joseph Z, Pieter C A, Bruijnincx Anna L J, et al. The catalytic valorization of lignin for the production of renewable chemicals[J]. Chem Rev,2010,110(6):3552.
4 Li C, Zhao X, et al. Catalytic transformation of lignin for the production of chemicals and fuels[J]. Chem Rev,2015,115(21):11559.
5 Ma Z, Ekaterina T, Jeroen A B. Controlling the selectivity to che-micals from lignin via catalytic fast pyrolysis [J]. Appl Catal A: General,2012,423(424):130.
6 D`Aleio G F. Process of preparing a lignin-phenol-formaldehyde resin dispersion: US2357090[P].1944-08-29.
7 Christoph A G, Gregor H, Andreas S, et al. Multi-catalysis reactions: New prospects and challenges of biotechnology to valorize lignin[J]. Appl Microbiol Biot,2012,95(5):1115.
8 Davinia S, Eric M K, Claire T N, et al. Towards lignin consolidated bioprocessing: Simultaneous lignin depolymerization and product generation by bacteria [J]. Green Chem,2015,17:4951.
9 Phillip F B, et al. Pyrolysis mechanisms of lignin: Surface-immobilized model compound investigation of acid-catalyzed and free-radical reaction pathways [J]. J Anal Appl Pyrol,1995,33:1.
10 Peter J D, Martin S, Fanny T, et al. Aromatic monomers by in situ conversion of reactive intermediates in the acid-catalyzed depolyme-rization of lignin[J]. J Am Chem Soc,2015,137(23):7456.
11 Zeng J, GeunYoo C, Wang F, et al. Biomimetic fenton-catalyzed lignin depolymerization to high value aromatics and dicarboxylic acids[J]. ChemSusChem, 2015, 8(5): 861.
12 Yuan Z S, Mathew L, et al. Hydrolytic degradation of alkaline lignin in hot-compressed water and ethanol[J]. Bioresource Technol,2010,101(23):9308.
13 Blair J C, John G E. Depolymerization of oak wood lignin under mild conditions using the acidic ionic liquid 1-H-3-methylimidazolium chloride as both solvent and catalyst [J]. Bioresource Technol,2012,118:584.
14 Huang X M, Tamás I K, Michael D B, et al. Ethanol as capping agent and formaldehyde scavenger for efficient depolymerization of lignin to aromatics [J]. Green Chem,2015,17:4941.
15 Chen F, Meng X, Xiao F S. Mesoporous solid acid catalysts [J]. Catal Surv Asia,2011,15(1):37.
16 Xie W,Qi C, Wang H, et al. Phenylsulfonic acid functionalized mesoporous SBA-15 silica: A heterogeneous catalyst for removal of free fatty acids in vegetable oil [J]. Fuel Process Technol,2014,119:98.
17 Lilis H, Ahmad Z A, Abdul R M. Synthesis of monoglyceride through glycerol esterification with lauric acid over propyl sulfonic acid post-synthesis functionalized SBA-15 mesoporous catalyst [J]. Chem Eng J,2011,174(2-3):668.
18 Zwo D, James L, Dan C, et al. Sulfonic acid functionalized mesoporous SBA-15 catalysts for biodiesel production [J]. Appl Catal B-Environ,2013,129:342.
19 Gabriel M L, Fernando B, et al. Low-grade oils and fats: Effect of several impurities on biodiesel production over sulfonic acid heterogeneous catalysts [J]. Bioresource Technol,2011,102(20):9571.
20 Elisabetta M U, Maria F S, Daniela M, et al. Sulfonic acid-functio-nalized mesoporous silicas: Microcalorimetric characterization and catalytic performance toward biodiesel synthesis [J]. Microp Mesop Mat,2013,179:54.
21 Gabriel M, L Fernando B, Juan A M, et al. Biodiesel production from crude palm oil using sulfonic acid-modified mesostructured catalysts [J]. Chem Eng J,2010,161(3):323.
22 Isa K M, Kyle J M, Brent H S. Acidic mesoporous silica for the ca-talytic conversion of fatty acids in beef tallow [J]. Ind Eng Chem Res,2006,45(9):3022.
23 Michikazu H. Biodiesel production by amorphous carbon bearing SO₃H, COOH and phenolic OH groups, a solid Brnsted acid catalyst [J]. Top Catal,2010,53(11):805.
24 Ayillath K D, Paresh L D. Lignin depolymerization into aromatic monomers over solid acid catalysts [J]. ACS Catal,2015,5(1):365.
25 Fan C, Guan H, Zhang H, et al. Conversion of fructose and glucose into 5-hydroxymethylfurfural catalyzed by a solid heteropolyacid salt [J]. Biomass Bioenerg,2011,35(7):2659.
26 Matthew T, Chunbao (Charles) X. Liquefaction of bio-mass in hot-compressed water for the production of phenolic compounds [J]. Bioresource Technol,2010,101(7):2483.
27 Ana T, Luis S, Jalel L. Organosolv lignin depolymerization with different base catalysts [J]. J Chem Technol Biotechnol,2012,87(11):1593.
28 Zhang J, Jason T, Chen X, et al. A series of NiM (M= Ru, Rh, and Pd) bimetallic catalysts for effective lignin hydrogenolysis in water [J]. ACS Catal,2014,4(5):1574.
29 Shu R, Long J, Yuan Z, et al. Efficient and product-controlled depolymerization of lignin oriented by metal chloride cooperated with Pd/C [J]. Bioresource Technol,2015,179:84.
30 Trasarti A F, Segobia D J, Apesteguía C R, et al. Selective hydrogenation of soybean oil on copper catalysts as a tool towards improved bioproducts [J]. J Am Oil Chem Soc,2012,89(12):2245.
31 Irina L S, Olga A S, Anatoliy V R, et al. Hydrogenation of vegetable oils over Pd on nanocomposite carbon catalysts[J]. Ind Eng Chem Res,2008,47(19):7219.
32 Tarit N, Ron C R, Susan E E, et al. Upgrading of lignin-derived compounds: Reactions of eugenol catalyzed by HY zeolite and by Pt/γ-Al₂O₃ [J]. Catal Lett,2012,142:151.
33 Li H, Yu D, Yu Y, et al. Effect of preparation method on the structure and catalytic property of activated carbon supported nickel oxide catalysts [J]. Carbon,2010,48(15):4547.
34 Daniel F, Ursel H, Philipp K, et al. Influence of RANEY nickel on the formation of intermediates in the degradation of lignin [J]. Int J Chem Eng,2012,2012:8.
35 Ning Y, Chen Z, Paul J D, et al. Selective degradation of wood lignin over noble metal catalysts in a two-step process [J]. ChemSusChem,2008,1(7):626.
36 Susan K H, Baker R T. Knocking on wood: Base metal complexes as catalysts for selective oxidation of lignin models and extracts [J]. Acc Chem Res,2015,48(7):2037.
37 Tian S,Li Y,Li M, et al. Structural isomerism in gold nanoparticles revealed by X-ray crystallography [J]. Nat Commun,2015,6:1.
38 James M P, Harold H. Studies on lignin and related compounds. Lxxxvii. High pressure hydrogenation of maple wood [J]. J Am Chem Soc,1948,70(1):67.
39 Ernest W, Enrique L M, Charles S S. Nickel-induced conversion of carbon-oxygen into carbon-carbon bonds. One-step transformations of enol ethers into olefins and aryl ethers into biaryls[J]. J Am Chem Soc,1979,101(8):2246.
40 Alexey G S, John F H. Selective, nickel-catalyzed hydrogenolysis of aryl ethers [J]. Science, 2011,332(6028):439.
41 Michèle B, Pierre G, Catherine P. Conversion of biomass into che-micals over metal catalysts [J]. Chem Rev,2014,114(3):1827.
42 Armindo R G, José A F G, Dmitry V E, et al. Alternatives for lignocellulosic pulp delignification using polyoxometalates and oxygen: A review [J]. Green Chem,2007,9:717.
43 Magario I, Einschlag F S García, Rueda E H, et al. Mechanisms of radical generation in the removal of phenol derivatives and pigments using different Fe-based catalytic systems [J]. J Mol Catal A-Chem,2012,352:1.
44 Ning Y, Yuan Y, Ryan D, et al. Hydrodeoxygenation of lignin berived phenols into alkanes by using nanoparticle catalysts combined with Brønsted acidic ionic liquids [J]. Angrew Chem Int Ed,2010,49(32):5549.
45 Hai W, Melvin T, Yun J. Recent development in chemical depolymerization of lignin: A review [J]. J Appl Chem,2013,2013:1.
46 Yang Y, Fan H, Song J, et al. Free radical reaction promoted by io-nic liquid: A route for metal-free oxidation depolymerization of lignin model compound and lignin [J]. Chem Commun,2015,51:4028.
47 Lu Z, Zheng H, Fan L, et al. Direct liquefaction of biomass in a 1-(4-Sulfobutyl)-3-methylmidazolium hydrosulfate ionic liquid/1-octanol catalytic system [J]. Energy Fuel,2014,28:1139.
48 Bin L, Ilari F, Dimitris S A. Acidolysis of wood in ionic liquids [J]. Ind Eng Chem Res,2010,49(7):3126.
49 Jia S, Cox B J, et al. Hydrolytic cleavage of beta-O-4 ether bonds of lignin model compounds in an ionic liquid with metal chlorides [J]. Ind Eng Chem Res,2011,50(2):849.
50 Yu H, Hu J, Fan J, et al. One-pot conversion of sugars and lignin in ionic liquid and recycling of ionic liquid [J]. Ind Eng Chem Res,2012,51(8):3452.
51 Joseph Z, Anna L J, Bert M W. Transition metal catalyzed oxidation of Alcell lignin, soda lignin, and lignin model compounds in ionic li-quids [J]. Green Chem,2010,12:1225.
52 Fernández-Prinia R, Laura J M, Ernesto M. Near-critical and supercritical dilute solutions viewed from macroscopic and molecular-scale perspectives [J]. J Supercrit Fluid,2010,55(2):472.
53 Kruse A, Dinjus E. Hot compressed water as reaction medium and reactant: Properties and synthesis reactions [J]. J Supercrit Fluid,2007,41(3):361.
54 Saqib S T, Lasse R, Andreas R. Hydrothermal liquefaction of biomass: A review of subcritical water technologies [J]. Energy,2011,36(5):2328.
55 Jae-Young K Jeesu P, Hyewon H, Jeong K K, et al. Catalytic depolymerization of lignin macromolecule to alkylated phenols over va-rious metal catalysts in supercritical tert-butanol [J]. J Anal Appl Pyrol,2015,113:99.
56 Huang X, Ceylanpinar A, Tamás I K, et al. Role of Cu-Mg-Al mixed oxide catalysts in lignin depolymerization in supercritical ethanol [J]. ACS Catal,2015,5(12):7359.
57 Richard J A G, Wouter T, Jan E G D, et al. Lignin depolymerisation in supercritical carbon dioxide/acetone/water fluid for the production of aromatic chemicals [J]. Bioresource Technol,2012,106:173.
58 Edita J G, Matjaž K, Claudia C. Lignin structural changes during liquefaction in acidified ethylene glycol [J]. J Wood Chem Technol,2012,32(4):342.
59 Ane S, Luis S, Rodrigo B, et al. Lignin liquefaction under microwave heating [J]. J Appl Sci,2013,130(5):3292.
60 Matjaž K,Edita J,NataŠa C.Ultrasonically assisted liquefaction of lignocellulosic materials [J].Bioresource Technol,2012,103(1):360.
61 Shaveta, Harshpinder K, Palwinder S. Microwave assisted degradation of lignin to monolignols [J]. Pharm Anal Acta,2014,5:308.