Oxidative Degradation of Soda Lignin Assisted by Microwave Irradiation

Abstract

Abstract: The effects of oxidant dosage,oxidation temperature and time on the degradation of soda lignin by hydrogen peroxide with and without the presence of microwave irradiation were investigated.It is found that the oxidative degradation of lignin includes the cleavage of ether bond in β-O-4 structure,the partial destruction of aromatic ring,and the re-condensation of the degraded lignin.Compared to the conventionally heated oxidation of lignin,the microwave irradiation efficiently facilitates the degradation of the lignin with high molecular weight and the re-condensation of that with low molecular weight at a low oxidant dosage,low oxidation temperature,or a short oxidation time,which leads to the formation of the degraded lignin with narrower molecular weight distribution and lower molecular weight.Additionally,the lignin degraded in the presence of microwave irradiation has the characteristics of higher content of phenolic hydroxyl group,lower content of methoxyl group,and lower degree of condensation,which enhances the reactivity of lignin.Therefore,the oxidative degradation of lignin assisted by microwave irradiation may be a new pretreatment approach for efficiently utilizing the soda lignin.

Key words: oxidation, degradation, soda lignin, microwave irradiation

摘要： The effects of oxidant dosage,oxidation temperature and time on the degradation of soda lignin by hydrogen peroxide with and without the presence of microwave irradiation were investigated.It is found that the oxidative degradation of lignin includes the cleavage of ether bond in β-O-4 structure,the partial destruction of aromatic ring,and the re-condensation of the degraded lignin.Compared to the conventionally heated oxidation of lignin,the microwave irradiation efficiently facilitates the degradation of the lignin with high molecular weight and the re-condensation of that with low molecular weight at a low oxidant dosage,low oxidation temperature,or a short oxidation time,which leads to the formation of the degraded lignin with narrower molecular weight distribution and lower molecular weight.Additionally,the lignin degraded in the presence of microwave irradiation has the characteristics of higher content of phenolic hydroxyl group,lower content of methoxyl group,and lower degree of condensation,which enhances the reactivity of lignin.Therefore,the oxidative degradation of lignin assisted by microwave irradiation may be a new pretreatment approach for efficiently utilizing the soda lignin.

关键词: oxidation, degradation, soda lignin, microwave irradiation

OUYANG Xinping, LIN Zaixiong, DENG Yonghong, YANG Dongjie, QIU Xueqing. Oxidative Degradation of Soda Lignin Assisted by Microwave Irradiation[J]. , 2010, 18(4): 695-702.

欧阳新平, 林再雄, 邓永红, 杨东杰, 邱学青. Oxidative Degradation of Soda Lignin Assisted by Microwave Irradiation[J]. , 2010, 18(4): 695-702.

References

1 Lara,M.,Rodriguez-Malaver,J.,Rojas,O. J.,Holmquist,O.,Gonzalez,A.M.,Bullon,J.,Penaloza,N.,Araujo,E.,“Blackliquor lignin biodegradation by Trametes elegans”,Int.Biodeter.Biodegr.,52, 167-173(2003).
2 Pouteau,C.,Dole,P.,Cathala,B.,Averous,L.,Boquillon,N.,“Antioxidant properties of lignin in polypropylene”,Polym.Degrad. Stabil.,81,9-18(2003).
3 Gundersen,S.,Ese,M.,Sjoblom,J.,“Langmuir surface and inter face films of lignosulfonates and kraft lignins in the presence of electrolyte and asphaltenes:correlation to emulsion stability”,Colloid Surface:A,82,199-218(2001).
4 Huang,G.,Zhang,C.,Chen,Z.,“Catalytic activity of the black liquor and calcium mixture in CO₂ gasification of Fujian anthracite”, Chin.J.Chem.Eng.,15,670-679(2007).
5 Meister,J.,Lathia,A.,Chang,F.,“Solvent effects,species and extraction method effects,and coinitiator effects in the grafting of lignin”,J.Polym.Sci.Pol.Chem.,29,1465-1473(1991).
6 Guo,X.,Zhang,S.,Shan,X.,“Adsorption of metal ions on lignin”,J. Hazard.Mater.,151,134-142(2008).
7 Koshijima,T.,Muraki,E.,“Radical grafting on lignin.1.Radiationinduced grafting of styrene onto hydrochloric acid lignin”,J.Polym. Sci.Pol.Chem.,6,1431-1440(1968).
8 Mai,C.,Majcherczyk,A.,Huttermann,A.,“Chemo-enzymatic synthesisand characterization of graft copolymers from lignin and acrylic compounds”,Enzyme.Microb.Tech.,27,167-175(2000).
9 Xiao,B.,Sun,X.,Sun,R.,“The chemical modification of lignins with succinic anhydride in aqueous systems”,Polym.Degrad.Stabil., 71,223-231(2001).
10 Matsushita,Y.,Yasuda,S.,“Preparation and evaluation of lignosulfonates as a dispersant for gypsum paste from acid hydrolysis lignin”, Bioresource Technol.,96,465-470(2005).
11 Li,J.,Gellerstedt,G.,“Improved lignin properties and reactivity by modifications in the autohydrolysis process of aspen wood”,Ind. Crop.Prod.,27,175-181(2008).
12 Leonowicz,A.,Matuszewska,A.,Luterek,J.,Ziegenhagen,D., Wojtas-Wasilewska,M.,Cho,N.,Hofrichter,M.,Rogalski,J., “Biodegradation of lignin by white rot fungi“,Fungal Genet.Biol., 27,175-85(1999). 13 Hatakka,A.,“Biodegradation of lignin”,Biopolymers,1,129-180 (2001).
14 Pasquali,C.E.,Herrera,H.,“Pyrolysis of lignin and IR analysis of residues”,Thermochim.Acta,293,39-46(1997).
15 Sharma,R.,Wooten,J.,Baliga,V.,Lin,X.,Chan,W.,Hajaligol,M., “Characterization of chars from pyrolysis of lignin”,Fuel,83, 1469-1482(2004).
16 Tanaka,K.,Calanag,R.,Hisanaga,T.,“Photocatalyzed degradation of lignin on titanium dioxide”,J.Mol.Catal.A—Chem.,138,287-294 (1999).
17 Kansal,S.,Singh,M.,Sud,D.,“Studies on TiO₂/ZnO photocatalysed degradation of lignin”,J.Hazard.Mater.,153,412-417(2008).
18 Lin,S.,Dence,C.,Methods in Lignin Chemistry,Springer,Berlin, Germany,301-332(1992).
19 Zhang,Z.,Shan,Y.,Wang,J.,Ling,H.,Zang,S.,Gao,W.,Zhao,Z., Zhang,H.,“Investigation on the rapid degradation of congo red catalyzed by activated carbon powder under microwave irradiation”, J.Hazard.Mater.,147,325-333(2007).
20 Zhang,L.,Guo,X.,Yan,F.,Su,M.,Li,Y.,“Study of the degradation behaviour of dimethoate under microwave irradiation”,J.Hazard. Mater.,149,675-679(2007).
21 Ju,Y.,Yang,S.,Ding,Y.,Sun,C.,Gu,C.,He,Z.,Qin,C.,He,H., Xu,B.,“Microwave-enhanced H₂O₂-based process for treating aqueous malachite green solutions:Intermediates and degradation mechanism”,J.Hazard.Mater.,171,123-132(2009).
22 Mosier,N.,Wyman,C.,Dale,B.,Elander,R.,Lee,Y.Y.,Holtzapple, M.,Ladisch,M.,“Features of promising technologies for pretreatment of lignocellulosic biomass”,Bioresource Technol.,96,673-686 (2005).
23 Gidh,A.,Decker,S.,See,C.,Himmel,M.,Williford,C.,“Characterization of lignin using multi-angle laser light scatting and atomic force microscopy”,Anal.Chim.Acta.,555,250-258(2006).
24 Gosselink,R.,Ab?cherli,A.,Semke,H.,Malherbe,R.,K?uper,P., Nadif,A.,Van Dam,J.,“Analytical protocols for characterisation of sulphur-free lignin”,Ind.Crop.Prod.,19,271-281(2004).
25 Lin,S.,Dence,C.,Methods in Lignin Chemistry,Springer,Berlin, Germany,459-471(1992).
26 Himme,L.,Sopher,D.,“High performance size exclusion chromatography of low-molecular-weight lignins and model compounds”,J. Chromatogr.,267,249-265(1983).
27 Sun,R.,Tomkinson,J.,Ye,J.,“Physico-chemical and structural characterization of residual lignins isolated with TAED activated peroxide from ultrasound irradiated and alkali pre-treated wheat straw”,Polym.Degrad.Stabil.,79,241-251(2003).
28 Gavrilescu,D.,“On the importance of radical formation in pulp bleaching”,Cell Chem.Technol.,39,531-549(2005).
29 Shao,S.,Wen,G.,Jin,Z.,“Changes in chemical characteristics of bamboo(Phyllostachys pubescens)components during steam explosion”,Wood Sci.Technol.,42,439-451(2008).
30 Hawkes,G.,Smith,C.,Utley,J.,Vargas,V.,”A comparison of solution and solid state 13 C NMR spectra of lignin and lignin model compounds”,Holzforschung,47,302-312(1993).
31 Liitia,T.,Maunu,S.,Sipila,J.,Hortling,B.,“Application of solid-state 13 C NMR spectroscopy and dipolar dephasing technique to determine the extent of condensation in technical lignins”,Solid State Nucl.Mag.,21,171-186(2002).

[1]	Xia Miao, Xiaofan Pang, Shiyu Li, Haoguang Wei, Jianhao Yin, Xiangming Kong. Mechanical strength and the degradation mechanism of metakaolin based geopolymer mixed with ordinary Portland cement and cured at high temperature and high relative humidity [J]. Chinese Journal of Chemical Engineering, 2023, 60(8): 118-130.
[2]	Xiaolin Pan, Mengyuan Gao, Yun Wang, Yanping He, Tian Si, Yanlin Sun. Poly(lactic acid)-aspirin microspheres prepared via the traditional and improved solvent evaporation methods and its application performances [J]. Chinese Journal of Chemical Engineering, 2023, 60(8): 194-204.
[3]	Xun Tao, Fan Zhou, Xinlei Yu, Songling Guo, Yunfei Gao, Lu Ding, Guangsuo Yu, Zhenghua Dai, Fuchen Wang. Effect of carbon dioxide on oxy-fuel combustion of hydrogen sulfide: An experimental and kinetic modeling [J]. Chinese Journal of Chemical Engineering, 2023, 59(7): 105-117.
[4]	Zijie Zhang, Qianyu Zha, Ying Liu, Zhibing Zhang, Jia Liu, Zheng Zhou. Study on the epoxidation of olefins with H₂O₂ catalyzed by biquaternary ammonium phosphotungstic acid [J]. Chinese Journal of Chemical Engineering, 2023, 58(6): 146-154.
[5]	Chenyang Zhao, Yinhan Cheng, Guangfei Qu, Yongheng Yuan, Fenghui Wu, Ye Liu, Shan Liu, Junyan Li, Ping Ning. High-performance liquid-phase catalytic purification of phosphine in tail gas using Pd(II)/Cu(II) composite [J]. Chinese Journal of Chemical Engineering, 2023, 57(5): 98-108.
[6]	Hu Chen, Ying Wang, Puyu Wang, Yongkang Lv. Assessing quinoline removal performances of an aerobic continuous moving bed biofilm reactor (MBBR) bioaugmented with Pseudomonas citronellolis LV1 [J]. Chinese Journal of Chemical Engineering, 2023, 57(5): 132-140.
[7]	Yaqiao Liu, Shuozhen Hu, Xinsheng Zhang, Shigang Sun. Investigation of photoelectrocatalytic degradation mechanism of methylene blue by α-Fe₂O₃ nanorods array [J]. Chinese Journal of Chemical Engineering, 2023, 57(5): 162-172.
[8]	Bingxiao Feng, Lining Hao, Chaoting Deng, Jiaqiang Wang, Hongbing Song, Meng Xiao, Tingting Huang, Quanhong Zhu, Hengjun Gai. A highly hydrothermal stable copper-based catalyst for catalytic wet air oxidation of m-cresol in coal chemical wastewater [J]. Chinese Journal of Chemical Engineering, 2023, 57(5): 338-348.
[9]	Shengfeng Luo, Song Zhang, Yiping Zeng, Hui Zhang, Lili Zheng, Zhaopeng Xu. Study on oxygen transport and titanium oxidation in coating cracks under parallel gas flow based on LBM modelling [J]. Chinese Journal of Chemical Engineering, 2023, 56(4): 15-24.
[10]	Jiajun Wang, Wenbin Yang, Jiangtao Geng, Zhigang Shao, Wei Song. Experimental investigation on degradation mechanism of membrane electrode assembly at different humidity under automotive protocol [J]. Chinese Journal of Chemical Engineering, 2023, 56(4): 70-79.
[11]	Yuxi Chai, Yanan Zhang, Yannan Tan, Zhiwei Li, Huangzhao Wei, Chenglin Sun, Haibo Jin, Zhao Mu, Lei Ma. Life cycle assessment of high concentration organic wastewater treatment by catalytic wet air oxidation [J]. Chinese Journal of Chemical Engineering, 2023, 56(4): 80-88.
[12]	Peiyin Chen, Yanxiong Fang, Kaihong Xie, Yao Chen, Yang Liu, Hongliang Zuo, Weijian Lu, Baoyu Liu. Lacunary silicotungstic heteropoly salts as high-performance catalysts in oxidation of cyclopentene [J]. Chinese Journal of Chemical Engineering, 2023, 56(4): 152-159.
[13]	Iltaf Khan, Chunjuan Wang, Shoaib Khan, Jinyin Chen, Aftab Khan, Sayyar Ali Shah, Aihua Yuan, Sohail Khan, Mehwish K. Butt, Humaira Asghar. Bio-capped and green synthesis of ZnO/g-C₃N₄ nanocomposites and its improved antibiotic and photocatalytic activities: An exceptional approach towards environmental remediation [J]. Chinese Journal of Chemical Engineering, 2023, 56(4): 215-224.
[14]	Tinghao Jia, Yunbo Yu, Qing Liu, Yao Yang, Ji-Jun Zou, Xiangwen Zhang, Lun Pan. Theoretical and experimental study on the inhibition of jet fuel oxidation by diarylamine [J]. Chinese Journal of Chemical Engineering, 2023, 56(4): 225-232.
[15]	Da Ke, Minjia Wang, Jiancheng Ruan, Xinzhi Chen, Shaodong Zhou. Efficient, continuous oxidation of durene to pyromellitic dianhydride mediated by a V-Ti-P ternary catalyst: The remarkable doping effect [J]. Chinese Journal of Chemical Engineering, 2023, 55(3): 156-164.