木质素催化氧化解聚研究进展Progress in catalytic oxidative depolymerization of lignin
胡育珍,张琦,王晨光,张兴华,严龙,徐莹
摘要(Abstract):
木质素是自然界中唯一能直接提供芳环的可再生资源。然而,受制于其分子中致密的三维网状芳环结构和复杂化学键合方式,超过98%的工业木质素在纸浆和造纸工业中被焚烧,造成极大的资源浪费。木质素氧化解聚转化为香草醛等高度官能化的单体是一个重要且有前景的手段。文章主要介绍了木质素的结构、种类和解聚方法,从催化剂以及催化转化路线方面详细介绍了目前国内外在木质素氧化解聚研究领域的最新进展。在此基础上,对近期热门的非常规活化方法进行了调研与分析。最后总结了当前木质素氧化解聚研究存在的问题,并提出了未来可能的发展方向。
关键词(KeyWords): 生物质;木质素;解聚;氧化;催化
基金项目(Foundation): 国家重点研发计划(2017YFE01066100);; 国家自然科学基金(51876209,51536009);; 广东省“珠江人才计划”本土创新科研团队项目(2017BT01N092);; 中国科学院率先行动“百人计划”
作者(Author): 胡育珍,张琦,王晨光,张兴华,严龙,徐莹
参考文献(References):
- [1]RAGAUSKAS A J,BECKHAM G T,BIDDY M J,et al.Lignin valorization:improving lignin processing in the biorefinery[J].Science,2014,344(6185):1246843.
- [2]XU C,ARANCON R A D,LABIDI J,et al.Lignin depolymerisation strategies:Towards valuable chemicals and fuels[J].Chemical Society Reviews,2014,43(22):7485-7500.
- [3]HUANG Y,DUAN Y J,QIU S,et al.Lignin-first biorefinery:A reusable catalyst for lignin depolymerization and application of lignin oil to jet fuel aromatics and polyurethane feedstock[J].Sustainable Energy&Fuels,2018,2(3):637-647.
- [4]NARRON R H,KIM H,CHANG H,et al.Biomass pretreatments capable of enabling lignin valorization in a biorefinery process[J].Current opinion in biotechnology,2016,38:39-46.
- [5]KEY R E,BOZELL J J.Progress toward lignin valorization via selective catalytic technologies and the tailoring of biosynthetic pathways[J].ACS Sustainable Chemistry&Engineering,2016,4(10):5123-5135.
- [6]ZAKZESKI J,BRUIJININCX 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.
- [7]LI C Z,ZHAO X C,WANG A Q,et al.Catalytic transformation of lignin for the production of chemicals and fuels[J].Chemical Reviews,2015,115(21):11559-11624.
- [8]VANGEEL T,SCHUTYSER W,RENDERS T,et al.Perspective on lignin oxidation:advances,challenges,and future directions[J].Topics in Current Chemistry,2018,376(4):30.
- [9]UPTON B M,KASKO A M.Strategies for the conversion of lignin to high-value polymeric materials:Review and perspective[J].Chemical Reviews,2015,116(4):2275-2306.
- [10]RINALDI R,JASTRZEBSKI R,CLOUGH M T,et al.Paving the way for lignin valorisation:Recent advances in bioengineering,biorefining and catalysis[J].Angewandte Chemie International Edition,2016,55(29):8164-8215.
- [11]CHKAR F S,RAGAUSKAS A J.Review of current and future softwood kraft lignin process chemistry[J].Industrial Crops and Products,2004,20(2):131-141.
- [12]TOLEDANO A,SERRANO L,LABIDI J.Organosolv lignin depolymerization with different base catalysts[J].Journal of Chemical Technology&Biotechnology,2012,87(11):1593-1599.
- [13]JIANG X X,Ellis N,ZHONG Z P.Characterization of pyrolytic lignin extracted from bio-oil[J].Chinese Journal of Chemical Engineering,2010,18(6):1018-1022.
- [14]LI J B,GELLERSTEDT G,TOVEN K.Steam explosion lignins;their extraction,structure and potential as feedstock for biodiesel and chemicals[J].Bioresource Technology,2009,100(9):2556-2561.
- [15]BEHLING R,VALANGE S,CHATEL G.Heterogeneous catalytic oxidation for lignin valorization into valuable chemicals:What results?What limitations?What trends?[J].Green Chemistry,2016,18(7):1839-1854.
- [16]BRUIJININCX P C A,WECHUYSEN B M.Biomass conversion:lignin up for break-down[J].Nature Chemistry,2014,6(12):1035.
- [17]舒日洋,徐莹,张琦,等,木质素催化解聚的研究进展[J].化工学报,2016,67(11):4524-4532.SHU R Y,XU Y,ZHANG Q,et al.Progress in catalytic depolymerization of lignin[J].CIESC Journal,2016,67(11):4524-4532.
- [18]CHAN M K,YE Q,PENG Z M,et al.Valorization of lignin:effective conversion of depolymerized lignin to oil by simple chemical modifications[J].Waste and Biomass Valorization,2017,8(6):2029-2036.
- [19]PANDEY M P,KIM C S.Lignin depolymerization and conversion:A review of thermochemical methods[J].Chemical Engineering&Technology,2011,34(1):29-41.
- [20]LASKAR D D,TUCKER M P,CHEN X,et al.Noble-metal catalyzed hydrodeoxygenation of biomass-derived lignin to aromatic hydrocarbons[J].Green Chemistry,2014,16(2):897-910.
- [21]ZHAI Y X,LI C,Xu G Y,et al.Depolymerization of lignin via a non-precious Ni-Fe alloy catalyst supported on activated carbon[J].Green Chemistry,2017,19(8):1895-1903.
- [22]SCHUTYSER W,KRUGER J S,ROBINSON A M,et al.Revisiting alkaline aerobic lignin oxidation[J].Green Chemistry,201820(16):3828-3844.
- [23]DAS L,KOLAR P,et al.Heterogeneous catalytic oxidation of lignin into value-added chemicals[J].Biofuels,2012,3(2):155-166.
- [24]MA R S,GUO M,ZHANG X.Recent advances in oxidative valorization of lignin[J].Catalysis Today,2018,302:50-60.
- [25]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.
- [26]沈晓骏,黄攀丽,文甲龙,等.木质素氧化还原解聚研究现状[J].化学进展,2017,29(1):162-178.SHEN X J,HUANG P L,WEN J L,et al.Research status of lignin oxidative and reductive depolymerization[J].Progress in Chemistry,2017,29(1):162-178.
- [27]YUAN Z,EDEN M R.Recent advances in optimal design of thermochemical conversion of biomass to chemicals and liquid fuels[J].Current Opinion in Chemical Engineering,2015,10:70-76.
- [28]MOTA M I F,LOUREIRO J M,et al.Recovery of vanillin and syringaldehyde from lignin oxidation:A review of separation and purification processes[J].Separation&Purification Reviews,2016,45(3):227-259.
- [29]TARABANKO V E,TARABANKO N.Catalytic oxidation of lignins into the aromatic aldehydes:General process trends and development prospects[J].International Journal of Molecular Sciences,2017,18(11):2421.
- [30]PINTO P C R,DA SILVA E A B,RODRIGUES A E.Biomass conversion[M].Berlin:Springer,2012.
- [31]SCHUTYSER W,RENDERS T,et al.Chemicals from lignin:An interplay of lignocellulose fractionation,depolymerisation,and upgrading[J].Chemical Society Reviews,2018,47(3):852-908.
- [32]SCHOENHERR S,EBRAHIMI M,CZERMAK P.Lignin-trends and applications[M].London:IntechOpen,2018.
- [33]FACHE M,BOUTEVIN B,CAILLOL S.Vanillin production from lignin and its use as a renewable chemical[J].ACS Sustainable Chemistry&Engineering,2015,4(1):35-46.
- [34]SALES F G,MARANHAO L C A,LIMA FILHO N M,et al.Kinetic evaluation and modeling of lignin catalytic wet oxidation to selective production of aromatic aldehydes[J].Industrial&Engineering Chemistry Research,2006,45(20):6627-6631.
- [35]BHARGAVA S,JANI H,TARDIO J,et al.Catalytic wet oxidation of ferulic acid(a model lignin compound)using heterogeneous copper catalysts[J].Industrial&Engineering Chemistry Research,2007,46(25):8652-8656.
- [36]VILLAR J C,CAPEROS A,et al.Oxidation of hardwood kraft-lignin to phenolic derivatives with oxygen as oxidant[J].Wood Science and Technology,2001,35(3):245-255.
- [37]DENG W,ZHANG H,WU X,et al.Oxidative conversion of lignin and lignin model compounds catalyzed by CeO 2-supported Pd nanoparticles[J].Green Chemistry,2015,17(11):5009-5018.
- [38]DENG H,LIN L,SUN Y,et al.Perovskite-type oxide LaMnO3:An efficient and recyclable heterogeneous catalyst for the wet aerobic oxidation of lignin to aromatic aldehydes[J].Catalysis Letters,2008,126(1/2):106-111.
- [39]DENG H,LIN L,SUN Y,et al.Activity and stability of perovskite-type oxide LaCoO3 catalyst in lignin catalytic wet oxidation to aromatic aldehydes process[J].Energy&Fuels,2008,23(1):19-24.
- [40]SHILPY M,EHSAN M A,ALI T H,et al.Performance of cobalt titanate towards H2O2 based catalytic oxidation of lignin model compound[J].RSC Advances,2015,5(97):79644-79653.
- [41]VOITL T,RUDOLF VON ROHR P.Oxidation of lignin using aqueous polyoxometalates in the presence of alcohols[J].ChemSusChem:Chemistry&Sustainability Energy&Materials,2008,1(8/9):763-769.
- [42]GAO T T,ZHOU X F,ZHU Z L.Catalytic conversion of kraft lignin using paper-like Co(salen)as an effective catalyst[J].Drewno.Prace Naukowe.Doniesienia.Komunikaty,2015,58(195):79-90.
- [43]DEMESA A G,LAARI A,TURENUN I,et al.Alkaline partial wet oxidation of lignin for the production of carboxylic acids[J].Chemical Engineering&Technology,2015,38(12):2270-2278.
- [44]TARABANKO V E,HENDOGINA Y V,PETUHOV D V,et al.On the role of retroaldol reaction in the process of lignin oxidation into vanillin.Kinetics of the vanillideneacetone cleavage in alkaline media[J].Reaction Kinetics and Catalysis Letters,2000,69(2):361-368.
- [45]CREIGHTON R H J,GIBBS R D,HIBBERT H.Studies on lignin and related compounds.lxxv.alkaline nitrobenzene oxidation of plant materials and application to taxonomic classification1[J].Journal of the American Chemical Society,1944,66(1):32-37.
- [46]DEUSS P J,BARTA K.From models to lignin:Transition metal catalysis for selective bond cleavage reactions[J].Coordination Chemistry Reviews,2016,306:510-532.
- [47]XIANG Q,Lee Y Y.Production of oxychemicals from precipitated hardwood lignin[C]//Twenty-Second Symposium on Biotechnology for Fuels and Chemicals.Totowa:Humana Press,2001:71-80.
- [48]WU G X,HEITZ M,CHORNET E.Improved alkaline oxidation process for the production of aldehydes(vanillin and syringaldehyde)from steam-explosion hardwood lignin[J].Industrial&Engineering Chemistry Research,1994,33(3):718-723.
- [49]WU G X,HEITZ M.Catalytic mechanism of Cu2+and Fe3+in alkaline O2 oxidation of lignin[J].Journal of Wood Chemistry and Technology,1995,15(2):189-202.
- [50]TARABANKO V E,FOMOVA N A,Kuznetsov B N,et al.On the mechanism of vanillin formation in the catalytic oxidation of lignin with oxygen[J].Reaction Kinetics and Catalysis Letters,1995,55(1):161-170.
- [51]WERHAN H,MIR J M,VOITL T,et al.Acidic oxidation of kraft lignin into aromatic monomers catalyzed by transition metal salts[J].Holzforschung,2011,65(5):703-709.
- [52]ZHANG J,LIU Y,CHIBA S,et al.Chemical conversion ofβ-O-4 lignin linkage models through Cu-catalyzed aerobic amide bond formation[J].Chemical Communications,2013,49(97):11439-11441.
- [53]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):1225-1236.
- [54]SEDAI B,BAKER R T,et al.Comparison of copper and vanadium homogeneous catalysts for aerobic oxidation of lignin models[J].ACS Catalysis,2011,1(7):794-804.
- [55]ZHU Y T,LIU J,LIAO Y H,et al.Degradation of vanillin during lignin valorization under alkaline oxidation[J].Topics in Current Chemistry,2018,376(4):29.
- [56]HOFFMANN J,NüCHTER M,ONDRUSCHKA B,et al.Ionic liquids and their heating behaviour during microwave irradiation-Astate of the art report and challenge to assessment[J].Green Chemistry,2003,5(3):296-299.
- [57]CHEN Q,KANEKO M,KASHIMURA K,et al.Direct production of vanillin from wood particles by copper oxide-peroxide reaction promoted by electric and magnetic fields of microwaves[J].ACS Sustainable Chemistry&Engineering,2017,5(12):11551-11557.
- [58]ZHU G D,JIN D X,ZHAO L S,et al.Microwave-assisted selective cleavage of CαCβbond for lignin depolymerization[J].Fuel Processing Technology,2017,161:155-161.
- [59]PAN J Y,FU J,LU X Y.Microwave-assisted oxidative degradation of lignin model compounds with metal salts[J].Energy&Fuels,2015,29(7):4503-4509.
- [60]OUYANG X P,LIN Z X,DENG Y H,et al.Oxidative degradation of soda lignin assisted by microwave irradiation[J].Chinese Journal of Chemical Engineering,2010,18(4):695-702.
- [61]OUYANG X P,TAN Y D,QIU X Q.Oxidative degradation of lignin for producing monophenolic compounds[J].Journal of Fuel Chemistry and Technology,2014,42(6):677-682.
- [62]OUYANG X P,HUANG X,RUAN T,et al.Microwave-assisted oxidative digestion of lignin with hydrogen peroxide for TOC and color removal[J].Water Science and Technology,2015,71(3):390-396.
- [63]YAO S G,MOBLEY J K,RALPH J,et al.Mechanochemical treatment facilitates two-step oxidative depolymerization of kraft lignin[J].ACS Sustainable Chemistry&Engineering,2018,6(5):5990-5998.
- [64]DABRAL S,WOTRUBA H,HERNANDEZ J G,et al.Mechanochemical oxidation and cleavage of ligninβ-O-4 model compounds and lignin[J].ACS Sustainable Chemistry&Engineering,2018,6(3):3242-3254.
- [65]MA Y S,Chang C N,Chiang Y P,et al.Photocatalytic degradation of lignin using Pt/TiO2 as the catalyst[J].Chemosphere,2008,71(5):998-1004.
- [66]GONG J Y,IMBAULT A,FARNOOD R.The promoting role of bismuth for the enhanced photocatalytic oxidation of lignin on Pt-TiO2 under solar light illumination[J].Applied Catalysis B:Environmental,2017,204:296-303.
- [67]TIAN M,WEN J L,MACDONALD D,et al.A novel approach for lignin modification and degradation[J].Electrochemistry Communications,2010,12(4):527-530.
- [68]TOLBA R,TIAN M,WEN J,et al.Electrochemical oxidation of lignin at IrO2-based oxide electrodes[J].Journal of Electroanalytical Chemistry,2010,649(1/2):9-15.
- [69]CAI P,FAN H X,CAO S,et al.Electrochemical conversion of corn stover lignin to biomass-based chemicals between Cu/Ni Mo Co cathode and Pb/PbO2 anode in alkali solution[J].Electrochimica Acta,2018,264:128-139.
- [70]WERHAN H,ASSMANN N,et al.Lignin oxidation studies in a continuous two-phase flow microreactor[J].Chemical Engineering and Processing:Process Intensification,2013,73:29-37.
- [71]DA SILVA E A B,ZABKOVA M,ARAüJO J D,et al.An integrated process to produce vanillin and lignin-based polyurethanes from Kraft lignin[J].Chemical Engineering Research and Design,2009,87(9):1276-1292.
- [72]ANDERSON E M,STONE M L,KATAHIRA R,et al.Flowthrough reductive catalytic fractionation of biomass[J].Joule,2017,1(3):613-622.