木素模型物及其在制浆中的应用研究进展
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摘要
木素是自然界储量仅次于纤维素和甲壳素的天然大分子聚合物。从化学结构上看,木素由愈创木基、对羟苯基和紫丁香基三种结构单元以醚键和碳碳双键连接而成,结构十分复杂,且在植物原料中,木素与纤维素和半纤维素紧密地联系在一起,利用现有手段很难分离出纯木素。木素对制浆过程,尤其是对蒸煮和纸浆漂白有重要影响,为深入理解木素在制浆过程中发生的化学反应机理及其结构变化,需要借助木素模型物进行木素的相关研究。本文综述了国内外木素模型物的研究现状,论述了木素模型物在制浆过程中木素-碳水化合物复合体(LCC)的生成及漂白过程中反应机理等相关研究中的应用情况。
Lignin,the natural macromolecular polymer,is the third largest biomass in nature reserves and under the reserves of cellulose and chitin. Lignin contains three structural units i. e. guaiacyl,syringyl and p-hydroxyphenol,which are connected by the bond of ether and CC,and ultimately formed complex chemical structures. Besides,lignin is closely associated with cellulose and hemicellulose in plants material,so it is difficult to isolate pure lignin by existing means. Pulping process is seriously affected by lignin,especially the processes of cooking and bleaching. In order to understand the chemical reaction mechanism and structural changes of lignin during pulpingprocess,the lignin model compounds should be used in the study. This paper reviews the recent developments of lignin model compounds. In addition,it particaly discusses the application of lignin model compounds in the researches of bleaching reaction mechanism and the formation of LCC in cooking process.
Lignin,the natural macromolecular polymer,is the third largest biomass in nature reserves and under the reserves of cellulose and chitin. Lignin contains three structural units i. e. guaiacyl,syringyl and p-hydroxyphenol,which are connected by the bond of ether and CC,and ultimately formed complex chemical structures. Besides,lignin is closely associated with cellulose and hemicellulose in plants material,so it is difficult to isolate pure lignin by existing means. Pulping process is seriously affected by lignin,especially the processes of cooking and bleaching. In order to understand the chemical reaction mechanism and structural changes of lignin during pulpingprocess,the lignin model compounds should be used in the study. This paper reviews the recent developments of lignin model compounds. In addition,it particaly discusses the application of lignin model compounds in the researches of bleaching reaction mechanism and the formation of LCC in cooking process.
引文
[1] Jiang Tingda. Lignin[M]. The 2nd edition. Beijing:Chemical Industry Press,2009.蒋挺大.木质素[M]. 2版.北京:化学工业出版社,2009.
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[3] Yang Shuhui. Plant Fiber Chemistry[M]. Beijing:China light industry press,2010.杨淑蕙.植物纤维化学[M].北京:中国轻工业出版社,2010.
[4] Dong Tan. Extraction and application of lignin in[J]. Guangxi chemical,1994(4):6.谭东.木质素的提取及应用[J].广西化工,1994(4):6.
[5] Kishimoto T. Synthesis of Lignin Model Compounds and Their Application to Wood Research[J]. Journal of the Japan Wood Research Society,2009,55(4):187.
[6] OU Guo-long,XIE Yi-min,ZHAO Hua-ping. Synthesis ofβ-O-4type lignin model compounds and their changes in GIF biodegrading system(I)[J]. Transactions of China Pulp and Paper,2001,16(2):29.欧国隆,谢益民,赵华平,et al.β-O-4型木素模型化合物的合成及其在GIF型仿酶降解体系中的变化(Ⅰ)[J].中国造纸学报,2001,16(2):29.
[7] Ouyang Xin-Ping,Yang Yun,et al. Radical synthesis of tetrameric lignin model compound[J]. Chinese Chemical Letters,2015,26(8):980.
[8] Ouyang X P,Liu C L,Pang Y X,et al. Synthesis of a trimeric lignin model compound composed ofα-O-4 andβ-O-4 linkages under microwave irradiation[J]. Chinese Chemical Letters, 2013, 24(12):1091.
[9] Deng Riling,Zhou Xuefei. Optimization of Synthesis Process Conditions of Polymeric Guaiacyl-type Lignin Model Compound[J]. Paper Science&Technology,2009,28(1):12.邓日灵,周学飞.愈创木基型多聚体木素模型物合成工艺条件的优化[J].造纸科学与技术,2009,28(1):12.
[10] Mostaghni F,Teimouri A,Mirshokraei S A. Synthesis,spectroscopic characterization and DFT calculations ofβ-O-4 type lignin model compounds[J]. Spectrochim Acta A Mol Biomol Spectrosc,2013,110(8):430.
[11] Nie M C,Huo S P,Kong Z W. Research progress of lignin model compounds[J]. Chemistry&Industry of Forest Products,2010,30(5):115.
[12] Gellerstedt G,Hardell H L,Lindfors E L. ChemInform Abstract:The Reactions of Lignin with Alkaline Hydrogen Peroxide. Part IV.Products from the Oxidation of Quinone Model Compounds[J].Cheminform,1981,12(16):669.
[13] Sun Yuanfang,Xie Yimin,Gao Honggui,et al. The 5-5'structure lignin model compound and the dehydropolymerization of P hydroxycinnamic acid under the action of laccase[J]. China Pulp and Paper Industry,2010,31(8):30.孙媛芳,谢益民,高洪贵,等.漆酶作用下5-5'结构木素模型化合物与对-羟基肉桂酸的脱氢聚合反应[J].中华纸业,2010,31(8):30.
[14] Deng Riling. Study on the mechanism of catalytic oxidation of lignin model compounds Co-salen complexes[D]. Kunming:Kunming University of Science and Technology,2009.邓日灵. Co-salen配合物催化氧化木素模型化合物的机理研究[D].昆明:昆明理工大学,2009.
[15] Mukhtar A,Zaheer M,Saeed M,et al. Synthesis of lignin model compound containing aβ-O-4 linkage[J]. Zeitschrift Für Naturforschung B,2017,72(2):119.
[16] Zakzeski J,Jongerius A L,Weckhuysen B M. Transition metal catalyzed oxidation of Alcell lignin,soda lignin,and lignin model compounds in ionic liquids[J]. Green Chemistry,2010,12(7):1225.
[17] Muheim A,Fiechter A,Harvey P J,et al. On the Mechanism of Oxidation of Non-Phenolic Lignin Model Compounds by the LaccaseABTS Couple[J]. Holzforschung,2017,46(2):121.
[18] Huang J,Liu C,Wu D,et al. Density functional theory studies on pyrolysis mechanism ofβ-O-4 type lignin dimer model compound[J]. Journal of Analytical&Applied Pyrolysis,2014,109:98.
[19] Yong S C,Singh R,Jing Z,et al. Pyrolysis reaction networks for lignin model compounds:unraveling thermal deconstruction ofβ-O-4andα-O-4 compounds[J]. Green Chemistry,2016,18(6):1762.
[20] Kishimoto T. Synthesis of lignin model compounds and Their Application to Wood Research[J]. Mokuzai Gakkaish, 2009, 55(4):187.
[21] Mattinen M L,Maijala P,Nousiainen P,et al. Oxidation of lignans and lignin model compounds by laccase in aqueoussolvent systems[J]. Journal of Molecular Catalysis B Enzymatic,2011, 72(3):122.
[22] Holmgren A,Norgren M,Zhang L,et al. On the role of the monolignol gamma-carbon functionality in lignin biopolymerization[J].Phytochemistry,2009,70(1):147.
[23] Matsushita Y,Yasuda S. Reactivity of a condensed-type lignin model compound in the Mannich reaction and preparation of cationic surfactant from sulfuric acid lignin[J]. Journal of Wood Science,2003,49(2):166.
[24] LIU Zu-guang,CHEN Zhao-hui,WANG Di-zhen. Research ProgressonMannichreactionoflignin[J]. Transactions of China Pulp and Paper,2007,22(1):104刘祖广,陈朝晖,王迪珍.木质素的Mannich反应研究进展[J].中国造纸学报,2007,22(1):104.
[25] Zhou Yan,Yang Zhiyong,Xie Yimin. The Research about the Formation of LCC during Kraft Cooking of Phenolic Lignin Model Compound[J]. Paper Science&Technology,2014,33(4):6.周燕,杨志勇,谢益民.酚型木素模型物硫酸盐法蒸煮过程中LCC形成的研究[J].造纸科学与技术,2014,33(4):6.
[26] YANG Zhi-yong,XIE Yi-min,ZHOU Yan. Using the phenolic lignin model to study the formation of LCC during the process of kraft cooking[J]. Transactions of China Pulp and Paper,2014,29(1):6.杨志勇,谢益民,周燕.利用酚型木素模型物研究硫酸盐法蒸煮过程中LCC的形成[J].中国造纸学报,2014,29(1):6.
[27] Xiao B,Sun X F,Sun R C. The chemical modification of lignins with succinic anhydride in aqueous systems[J]. Polymer Degradation&Stability,2001,71(2):223.
[28] Bj9rkman A. Studies of finely divided wood. Part 1. Extraction of lignin with neutral solvents[J]. Svensk Papperstidning,1956,59(13):477.
[29] ZHOU Yan,XIE Yi-min,GAN Ding-neng,et al. Synthesis of a condensed lignin model and changes in LCC[J]. Transactions of China Pulp and Paper,2006,21(1):5.周燕,谢益民,甘定能,等.缩合型木素模型物的合成及LCC的变化情况[J].中国造纸学报,2006,21(1):5.
[30] ZHANG Chun-yun,HU Hui-chao,CHAI Xin-sheng. A New Kinetics Model of Oxygen Delignification of Fast-growing Eucalyptus Kraft Pulp[J]. China Pulp&Paper,2012,31(6):1.张春云,胡会超,柴欣生.描述桉木硫酸盐氧脱木素过程动力学的新模型[J].中国造纸,2012,31(6):1.
[31] ZHU Bei-lei. The Reaction of Lingin and Lingin Model with Ozen[J]. China Pulp&Paper,1981(1):58.朱蓓蕾.木素和木素模型化合物与臭氧的反应[J].中国造纸,1981(1):58.
[32] Yan Z. Synthesis of Condensed Lignin Model Compound and Formation Mechanism of LCC during Kraft Cooking[J]. Journal of Cellulose Science&Technology,2006:220.
[33] Vikkula A,Vuorinen T. The formation of LC and other aromatic endgroup structures in O-alkyl-substituted cellulose during kraft pulping conditions[J]. Journal of Wood Science,2007,53(3):229.
[34] Nylander F. Lignin-carbohydrate complexes:Model compounds synthesis[J]//publications. lib. chalmers. se,2015.
[35] Tokimatsu T,Umezawa T,Shimada M. Synthesis of Four Diastereomeric Lignin Carbohydrate Complexes(LCC)Model Compounds Composed of a-O-4 Lignin Model Linked to Methyl-D-Glucoside[J]. Holzforschung,2009,50(2):156.
[36] Kovur S R. Synthesis and Enzymatic Oxidation of Model Lignin Carbohydrate Complexes[J]. Research Gate,2008.
[37] Mai T T N. Synthesis and Oxidation of Lignin-Carbohydrate Model Compounds[J]. Fisheries Science,2008,72(5):1066.
[38] Paice M G,Bourbonnais R,Reid I D. Bleaching kraft pulps with oxidative enzymes and alkaline hydrogen peroxide[J]. Tappi Journal,1995,78(9):161.
[39] An Junjian,Dai Zhongyi,Li Hui,et al. Study on degradation of lignin model compound guaiacol[J]. Heilongjiang paper,2015,43(4):1.安俊健,代中逸,黎辉,等.木素模型物愈创木酚的降解研究[J].黑龙江造纸,2015,43(4):1.
[40] Liu Haitang,Pei Jicheng. Using the lignin model to study the reaction of lignin in pulping from the molecular level[J]. paper and paper,2009,28(8):36.刘海棠,裴继诚.借助木素模型物从分子水平研究木素在制浆中的反应[J].纸和造纸,2009,28(8):36.
[41] Northey R A. A Review of Lignin Model Compound Reactions under Oxygen Bleaching Conditions[J]. Acs Symposium,2001,785:44.
[42] Ohmura S,Yokoyama T,Matsumoto Y. Significance of Side Chain Oxidation in the Reaction ofβ-O-4 Type Lignin Model Compounds with Active Oxygen Species Under Oxygen Bleaching Conditions[C]. Tianjin:16th1SWFPC,2011.
[43] Sippola V O,Krause A O I. Bis(o-phenanthroline)copper-catalysed oxidation of lignin model compounds for oxygen bleaching of pulp[J]. Catalysis Today,2005,100(3/4):237.
[44] Posoknistakul P,Akiyama T,Yokoyama T,et al. Predominant formation of aromatic aldehyde and acid from a dimericβ-O-4-type lignin model compound under hydrogen peroxide bleaching conditions with high pH levels[J]. Journal of Wood Science,2017,63(2):173.
[45] Daneault C,Robert S. Use of Taed as Activator to Increase Peroxide Bleaching-Lignin Model Compound and Optimized Conditions[C].Tianjin:16th1SWFPC,2011.
[46] Gonzlezriopedre G,Fernndezgarcía M I,Gómezfórneas E,et al.Biomimetic Catalysts for Oxidation of Veratryl Alcohol,a Lignin Model Compound[J]. Catalysts,2013,3(1):232.
[47] ZHANG Sheng-you,CAO Ying-ge,SU Zhen-hua,et al. The Source of AOX in Pulp and Paper Products and Its Reduction Measurements[J]. China Pulp&Paper,2015,2015,34(7):1.张升友,曹瀛戈,苏振华,等.我国制浆造纸AOX的来源分析及其减量化建议[J].中国造纸,2015,34(7):1.
[48] Nie S,Liu X,Wu Z,et al. Kinetics study of oxidation of the lignin model compounds by chlorine dioxide[J]. Chemical Engineering Journal,2014,241(142):410.
[49] Ni Y,Shen X,Arp V H. Studies on the reactions of phenolic and non-phenolic lignin model compounds with chlorine dioxide[J].Journal of Wood Chemistry&Technology,1994,14(2):243.
[2] Zhou Yan,Yang Zhiyong. Synthesis ofα-~13C labelledβ-O-4 lignin model compounds[C]. 2008(fifteenth)National Conference on Development and Application of Papermaking Chemicals,2008.周燕,杨志勇.α-~(13)C标记的β-O-4型木素模型化合物的合成[C].'2008(第十五届)全国造纸化学品开发应用技术研讨会论文集,2008.
[3] Yang Shuhui. Plant Fiber Chemistry[M]. Beijing:China light industry press,2010.杨淑蕙.植物纤维化学[M].北京:中国轻工业出版社,2010.
[4] Dong Tan. Extraction and application of lignin in[J]. Guangxi chemical,1994(4):6.谭东.木质素的提取及应用[J].广西化工,1994(4):6.
[5] Kishimoto T. Synthesis of Lignin Model Compounds and Their Application to Wood Research[J]. Journal of the Japan Wood Research Society,2009,55(4):187.
[6] OU Guo-long,XIE Yi-min,ZHAO Hua-ping. Synthesis ofβ-O-4type lignin model compounds and their changes in GIF biodegrading system(I)[J]. Transactions of China Pulp and Paper,2001,16(2):29.欧国隆,谢益民,赵华平,et al.β-O-4型木素模型化合物的合成及其在GIF型仿酶降解体系中的变化(Ⅰ)[J].中国造纸学报,2001,16(2):29.
[7] Ouyang Xin-Ping,Yang Yun,et al. Radical synthesis of tetrameric lignin model compound[J]. Chinese Chemical Letters,2015,26(8):980.
[8] Ouyang X P,Liu C L,Pang Y X,et al. Synthesis of a trimeric lignin model compound composed ofα-O-4 andβ-O-4 linkages under microwave irradiation[J]. Chinese Chemical Letters, 2013, 24(12):1091.
[9] Deng Riling,Zhou Xuefei. Optimization of Synthesis Process Conditions of Polymeric Guaiacyl-type Lignin Model Compound[J]. Paper Science&Technology,2009,28(1):12.邓日灵,周学飞.愈创木基型多聚体木素模型物合成工艺条件的优化[J].造纸科学与技术,2009,28(1):12.
[10] Mostaghni F,Teimouri A,Mirshokraei S A. Synthesis,spectroscopic characterization and DFT calculations ofβ-O-4 type lignin model compounds[J]. Spectrochim Acta A Mol Biomol Spectrosc,2013,110(8):430.
[11] Nie M C,Huo S P,Kong Z W. Research progress of lignin model compounds[J]. Chemistry&Industry of Forest Products,2010,30(5):115.
[12] Gellerstedt G,Hardell H L,Lindfors E L. ChemInform Abstract:The Reactions of Lignin with Alkaline Hydrogen Peroxide. Part IV.Products from the Oxidation of Quinone Model Compounds[J].Cheminform,1981,12(16):669.
[13] Sun Yuanfang,Xie Yimin,Gao Honggui,et al. The 5-5'structure lignin model compound and the dehydropolymerization of P hydroxycinnamic acid under the action of laccase[J]. China Pulp and Paper Industry,2010,31(8):30.孙媛芳,谢益民,高洪贵,等.漆酶作用下5-5'结构木素模型化合物与对-羟基肉桂酸的脱氢聚合反应[J].中华纸业,2010,31(8):30.
[14] Deng Riling. Study on the mechanism of catalytic oxidation of lignin model compounds Co-salen complexes[D]. Kunming:Kunming University of Science and Technology,2009.邓日灵. Co-salen配合物催化氧化木素模型化合物的机理研究[D].昆明:昆明理工大学,2009.
[15] Mukhtar A,Zaheer M,Saeed M,et al. Synthesis of lignin model compound containing aβ-O-4 linkage[J]. Zeitschrift Für Naturforschung B,2017,72(2):119.
[16] Zakzeski J,Jongerius A L,Weckhuysen B M. Transition metal catalyzed oxidation of Alcell lignin,soda lignin,and lignin model compounds in ionic liquids[J]. Green Chemistry,2010,12(7):1225.
[17] Muheim A,Fiechter A,Harvey P J,et al. On the Mechanism of Oxidation of Non-Phenolic Lignin Model Compounds by the LaccaseABTS Couple[J]. Holzforschung,2017,46(2):121.
[18] Huang J,Liu C,Wu D,et al. Density functional theory studies on pyrolysis mechanism ofβ-O-4 type lignin dimer model compound[J]. Journal of Analytical&Applied Pyrolysis,2014,109:98.
[19] Yong S C,Singh R,Jing Z,et al. Pyrolysis reaction networks for lignin model compounds:unraveling thermal deconstruction ofβ-O-4andα-O-4 compounds[J]. Green Chemistry,2016,18(6):1762.
[20] Kishimoto T. Synthesis of lignin model compounds and Their Application to Wood Research[J]. Mokuzai Gakkaish, 2009, 55(4):187.
[21] Mattinen M L,Maijala P,Nousiainen P,et al. Oxidation of lignans and lignin model compounds by laccase in aqueoussolvent systems[J]. Journal of Molecular Catalysis B Enzymatic,2011, 72(3):122.
[22] Holmgren A,Norgren M,Zhang L,et al. On the role of the monolignol gamma-carbon functionality in lignin biopolymerization[J].Phytochemistry,2009,70(1):147.
[23] Matsushita Y,Yasuda S. Reactivity of a condensed-type lignin model compound in the Mannich reaction and preparation of cationic surfactant from sulfuric acid lignin[J]. Journal of Wood Science,2003,49(2):166.
[24] LIU Zu-guang,CHEN Zhao-hui,WANG Di-zhen. Research ProgressonMannichreactionoflignin[J]. Transactions of China Pulp and Paper,2007,22(1):104刘祖广,陈朝晖,王迪珍.木质素的Mannich反应研究进展[J].中国造纸学报,2007,22(1):104.
[25] Zhou Yan,Yang Zhiyong,Xie Yimin. The Research about the Formation of LCC during Kraft Cooking of Phenolic Lignin Model Compound[J]. Paper Science&Technology,2014,33(4):6.周燕,杨志勇,谢益民.酚型木素模型物硫酸盐法蒸煮过程中LCC形成的研究[J].造纸科学与技术,2014,33(4):6.
[26] YANG Zhi-yong,XIE Yi-min,ZHOU Yan. Using the phenolic lignin model to study the formation of LCC during the process of kraft cooking[J]. Transactions of China Pulp and Paper,2014,29(1):6.杨志勇,谢益民,周燕.利用酚型木素模型物研究硫酸盐法蒸煮过程中LCC的形成[J].中国造纸学报,2014,29(1):6.
[27] Xiao B,Sun X F,Sun R C. The chemical modification of lignins with succinic anhydride in aqueous systems[J]. Polymer Degradation&Stability,2001,71(2):223.
[28] Bj9rkman A. Studies of finely divided wood. Part 1. Extraction of lignin with neutral solvents[J]. Svensk Papperstidning,1956,59(13):477.
[29] ZHOU Yan,XIE Yi-min,GAN Ding-neng,et al. Synthesis of a condensed lignin model and changes in LCC[J]. Transactions of China Pulp and Paper,2006,21(1):5.周燕,谢益民,甘定能,等.缩合型木素模型物的合成及LCC的变化情况[J].中国造纸学报,2006,21(1):5.
[30] ZHANG Chun-yun,HU Hui-chao,CHAI Xin-sheng. A New Kinetics Model of Oxygen Delignification of Fast-growing Eucalyptus Kraft Pulp[J]. China Pulp&Paper,2012,31(6):1.张春云,胡会超,柴欣生.描述桉木硫酸盐氧脱木素过程动力学的新模型[J].中国造纸,2012,31(6):1.
[31] ZHU Bei-lei. The Reaction of Lingin and Lingin Model with Ozen[J]. China Pulp&Paper,1981(1):58.朱蓓蕾.木素和木素模型化合物与臭氧的反应[J].中国造纸,1981(1):58.
[32] Yan Z. Synthesis of Condensed Lignin Model Compound and Formation Mechanism of LCC during Kraft Cooking[J]. Journal of Cellulose Science&Technology,2006:220.
[33] Vikkula A,Vuorinen T. The formation of LC and other aromatic endgroup structures in O-alkyl-substituted cellulose during kraft pulping conditions[J]. Journal of Wood Science,2007,53(3):229.
[34] Nylander F. Lignin-carbohydrate complexes:Model compounds synthesis[J]//publications. lib. chalmers. se,2015.
[35] Tokimatsu T,Umezawa T,Shimada M. Synthesis of Four Diastereomeric Lignin Carbohydrate Complexes(LCC)Model Compounds Composed of a-O-4 Lignin Model Linked to Methyl-D-Glucoside[J]. Holzforschung,2009,50(2):156.
[36] Kovur S R. Synthesis and Enzymatic Oxidation of Model Lignin Carbohydrate Complexes[J]. Research Gate,2008.
[37] Mai T T N. Synthesis and Oxidation of Lignin-Carbohydrate Model Compounds[J]. Fisheries Science,2008,72(5):1066.
[38] Paice M G,Bourbonnais R,Reid I D. Bleaching kraft pulps with oxidative enzymes and alkaline hydrogen peroxide[J]. Tappi Journal,1995,78(9):161.
[39] An Junjian,Dai Zhongyi,Li Hui,et al. Study on degradation of lignin model compound guaiacol[J]. Heilongjiang paper,2015,43(4):1.安俊健,代中逸,黎辉,等.木素模型物愈创木酚的降解研究[J].黑龙江造纸,2015,43(4):1.
[40] Liu Haitang,Pei Jicheng. Using the lignin model to study the reaction of lignin in pulping from the molecular level[J]. paper and paper,2009,28(8):36.刘海棠,裴继诚.借助木素模型物从分子水平研究木素在制浆中的反应[J].纸和造纸,2009,28(8):36.
[41] Northey R A. A Review of Lignin Model Compound Reactions under Oxygen Bleaching Conditions[J]. Acs Symposium,2001,785:44.
[42] Ohmura S,Yokoyama T,Matsumoto Y. Significance of Side Chain Oxidation in the Reaction ofβ-O-4 Type Lignin Model Compounds with Active Oxygen Species Under Oxygen Bleaching Conditions[C]. Tianjin:16th1SWFPC,2011.
[43] Sippola V O,Krause A O I. Bis(o-phenanthroline)copper-catalysed oxidation of lignin model compounds for oxygen bleaching of pulp[J]. Catalysis Today,2005,100(3/4):237.
[44] Posoknistakul P,Akiyama T,Yokoyama T,et al. Predominant formation of aromatic aldehyde and acid from a dimericβ-O-4-type lignin model compound under hydrogen peroxide bleaching conditions with high pH levels[J]. Journal of Wood Science,2017,63(2):173.
[45] Daneault C,Robert S. Use of Taed as Activator to Increase Peroxide Bleaching-Lignin Model Compound and Optimized Conditions[C].Tianjin:16th1SWFPC,2011.
[46] Gonzlezriopedre G,Fernndezgarcía M I,Gómezfórneas E,et al.Biomimetic Catalysts for Oxidation of Veratryl Alcohol,a Lignin Model Compound[J]. Catalysts,2013,3(1):232.
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