木质纤维素水热解聚制备能源化工平台化合物
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摘要
木质纤维素是制备生物液体燃料和化工品的理想原料。介绍了近年来木质纤维素通过水热解聚途径制备能源化工平台化合物和平台化合物碳链增长途径的研究进展,重点讨论了制备5-羟甲基糠醛(HMF)平台化合物的途径、介质、催化剂,分析了水热解聚技术的优势及困难,并对该领域的研究进行了展望。
Lignocellulosic biomass is an important feedstock for liquid biofuel and biochemical production. The recent advances of hydrothermal decomposition of lignocellulose to various small molecule organics as platform chemicals and the carbon-chain growth pathways of these platform chemicals are summarized. Particular emphasis is placed on the degrading process, reaction medium, catalysts for the platform production of 5-hydroxymethyl furfural(HMF). Major challenges and promising routes are also suggested for the future technology development of the hydrothermal decomposition of cellulosic biomass and chemocatalytic conversion of platform chemicals.
Lignocellulosic biomass is an important feedstock for liquid biofuel and biochemical production. The recent advances of hydrothermal decomposition of lignocellulose to various small molecule organics as platform chemicals and the carbon-chain growth pathways of these platform chemicals are summarized. Particular emphasis is placed on the degrading process, reaction medium, catalysts for the platform production of 5-hydroxymethyl furfural(HMF). Major challenges and promising routes are also suggested for the future technology development of the hydrothermal decomposition of cellulosic biomass and chemocatalytic conversion of platform chemicals.
引文
[1]张崇尚,刘乐,陆岐楠,等.中国秸秆能源化利用潜力与秸秆能源企业区域布局研究[J].资源科学,2017,39(3):473-481.
[2]CLIMENT M J,CORMA A,IBORRA S.Conversion of biomass platform molecules into fuel additives and liquid hydrocarbon fuels[J].Green Chemistry,2014,16(2):516-547.
[3]RASMUSSEN H,SORENSEN H R,MEYER A S.Formation of deg rad ation compou nds f rom lig nocellulosic biomass i n the biorefi nery:sugar reaction mechanisms[J].Carbohydrate Research,2014,385:45-57.
[4]RUIZ H A,RODRIGUEZ-JASSO R M,FERNANDES B D,et al.Hydrothermal processing,as an alternative for upgrading agriculture residues and marine biomass according to the biorefinery concept:a review[J].Renewable&Sustainable Energy Reviews,2013,21(4):35-51.
[5]CHERUBINI F,STROMMAN A H.Chemicals from lignocellulosic biomass:opportunities,perspectives,and potential of biorefi nery systems[J].Biofuels Bioproducts&Biorefi ning-Biofpr,2011,5(5):548-561.
[6]石宁.木质纤维素催化转化制备呋喃类平台化合物及长链烷烃[D].北京:中国科学院大学,2015.
[7]ISIKGOR F H,BECER C R.Lignocellulosic biomass:a sustainable platform for the production of bio-based chemicals and polymers[J].Polymer Chemistry,2015,6(25):4497-4559.
[8]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.
[9]BALAKRISHNAN M,SACIA E R,BELL A T.Syntheses of biodiesel precursors:sulfonic acid catalysts for condensation of biomass-derived platform molecules[J].Chem Sus Chem,2014,7(4):1078-1085.
[10]ZHANG X,ZHANG Q,WANG T,et al.Hydrodeoxygenation of lignin-derived phenolic compounds to hydrocarbons over Ni/Si O2-Zr O2 catalysts[J].Bioresource Technology,2013,134:73-80.
[11]XU J M,XIE X F,WANG J X,et al.Directional liquefaction coupling f ractionation of lig nocellulosic biomass for platfor m chemicals[J].Green Chemistry,2016,18(10):3124-3138.
[12]WANG T,NOLTE M W,SHANKS B H.Catalytic dehydration of C6carbohydrates for the production of hydroxymethylfurfural(HMF)as a versatile platform chemical[J].Green Chemistry,2014,16(2):548-572.
[13]HAO W,LI W,TANG X,et al.Catalytic transfer hydrogenation of biomass-derived 5-hydroxymethyl furfural to the building block 2,5-bishydroxymethyl furan[J].Green Chemistry,2016,18(4):1080-1088.
[14]ZHANG Z,WANG Q,XIE H,et al.Catalytic conversion of carbohydrates into 5-hydroxymethylfurfural by germanium(IV)chloride in ionic liquids[J].Chem Sus Chem,2011,4(1):131-138.
[15]GUAN J,CAO Q,GUO X,et al.The mechanism of glucose conversion to 5-hydroxymethylfurfural catalyzed by metal chlorides in ionic liquid:a theoretical study[J].Computational and Theoretical Chemistry,2011,963(2-3):453-462.
[16]BINDER J B,CEFALI A V,BLANK J J,et al.Mechanistic insights on the conversion of sugars into 5-hydroxymethylfurfural[J].Energy&Environmental Science,2010,3(6):765-771.
[17]AMARASEKARA A S,WILLIAMS L D,EBEDE C C.Mechanism of t he dehyd r at ion of D-f r uctose to 5-hyd roxy met hylf u r f u r al in dimethyl sulfoxide at 150℃:an NMR study[J].Carbohydrate Research,2008,343(18):3021-3024.
[18]杨越,刘琪英,蔡炽柳,等.木质纤维素催化转化制备DMF和C5/C6烷烃[J].化学进展,2016,28(2-3):363-374.
[19]WAN J,LIAN J,WANG Y,et al.Investigation of cellulose supramolecular structure changes during conversion of waste paper in near-critical water on producing 5-hydroxymethyl furfural[J].Renewable Energy,2015,80:132-139.
[20]FRANCAVILLA M,INTINI S,LUCHETTI L,et al.Tunable microwave-assisted aqueous conversion of seaweed-derived agarose for the selective production of 5-hydroxymethyl furfural/levulinic acid[J].Green Chemistry,2016,18(22):5971-5977.
[21]STAHLBERG T,FU W J,WOODLEY J M,et al.Synthesis of 5-(hydroxymethyl)furfural in ionic liquids:paving the way to renewable chemicals[J].Chem Sus Chem,2011,4(4):451-458.
[22]KASHIN A S,GALKIN K I,KHOKHLOVA E A,et al.Direct observation of self-organized water-containing str uctures in the liquid phase and their inf luence on 5-(hydroxymethyl)furfural formation in ionic liquids[J].Angewandte Chemie-Inter national Edition,2016,55(6):2161-2166.
[23]DING Z D,SHI J C,XIAO J J,et al.Catalytic conversion of cellulose to 5-hydroxymethyl furfural using acidic ionic liquids and co-catalyst[J].Carbohydrate Polymers,2012,90(2):792-798.
[24]BINDER J B,RAINES R T.Simple chemical transformation of lignocellulosic biomass into furans for fuels and chemicals[J].Journal of the American Chemical Society,2009,131(5):1979-1985.
[25]石宁,刘琪英,王铁军,等.葡萄糖催化脱水制取5-羟甲基糠醛研究进展[J].化工进展,2012,31(4):792-800.
[26]SHI N,LIU Q Y,ZHANG Q,et al.High yield production of5-hydroxymethylfurfural from cellulose by high concentration of sulfates in biphasic system[J].Green Chemistry,2013,15(7):1967-1974.
[27]SHI N,LIU Q Y,MA L L,et al.Direct degradation of cellulose to5-hydroxymethylfurfural in hot compressed steam with inorganic acidic salts[J].Rsc Advances,2014,4(10):4978-4984.
[28]DENG W P,ZHANG Q H,WANG Y.Catalytic transformations of cellulose and its derived carbohydrates into 5-hydroxymethylfurfural, levulinic acid,and lactic acid[J].Sci China-Chem,2015,58(1):29-46.
[29]GAO H P,PENG Y X,PAN J M,et al.Synthesis and evaluation of macroporous polymerized solid acid derived from pickering HIPEs for catalyzing cellulose into 5-hydroxymethylfurfural in an ionic liquid[J].Rsc Advances,2014,4(81):43029-43038.
[30]THOMBAL R S,JADHAV V H.Biomass derived beta-cyclodextrinSO3H carbonaceous solid acid catalyst for catalytic conversion of carbohydrates to 5-hydroxymethylfurfural[J].Applied Catalysis A:General,2015,499:213-216.
[31]ZHANG Y,WANG J J,REN J W,et al.Mesoporous niobium phosphate:an excellent solid acid for the dehydration of fructose to 5-hyd roxy met hylf u r f u r al i n water[J].Cat alysis Science&Technology,2012,2(12):2485-2491.
[32]ZHAO S,CHENG M X,LI J Z,et al.One pot production of5-hyd roxy met hylf u r f u ral w it h h ig h y ield f rom cellulose by a bronsted-lewis-surfactant-combined heteropolyacid catalyst[J].Chemical Communications,2011,47(7):2176-2178.
[33]VAN PUTTEN R J,VAN DER WAAL J C,DE JONG E,et al.Hydroxymethylfurfural,a versatile platform chemical made from renewable resources[J].Chemical Reviews,2013,113(3):1499-1597.
[34]WANG T F,NOLTE M W,SHANKS B H.Catalytic dehydration of C6 carbohydrates for the production of hydroxymethylfurfural(HMF)as a versatile platform chemical[J].Green Chemistry,2014,16(2):548-572.
[35]VAN ZANDVOORT I,WANG Y H,RASRENDRA C B,et al.For mation,molecular str uct ure,and mor phology of humins i n biomass conversion:inf luence of feedstock and processing conditions[J].Chem Sus Chem,2013,6(9):1745-1758.
[36]袁正求,龙金星,张兴华,等.木质纤维素催化转化制备能源平台化合物[J].化学进展,2016,28(1):103-110.
[37]蔡炽柳,刘琪英,王铁军,等.木质生物质平台化合物催化转化制备长链烷烃的反应路径与催化剂研究进展[J].林产化学与工业,2015,35(6):153-162.
[38]HUBER G W,CHHEDA J N,BARRETT C J,et al.Production of liquid alkanes by aqueous-phase processing of biomass-derived carbohydrates[J].Science,2005,308(5727):1446-1450.
[39]XIN J Y,ZHANG S J,YAN D X,et al.Formation of C—C bonds for the production of bio-alkanes under mild conditions[J].Green Chemistry,2014,16(7):3589-3595.
[40]HUANG Y B,YANG Z,DAI J J,et al.Production of high quality fuels from lignocellulose-derived chemicals:a convenient C—C bond formation of furfural,5-methylfurfural and aromatic aldehyde[J].Rsc Advances,2012,2(30):11211-11214.
[41]CORMA A,DE LA TORRE O,RENZ M.Production of high quality diesel from cellulose and hemicellulose by the sylvan process:catalysts and process variables[J].Energy&Environmental Science,2012,5(4):6328-6344.
[42]CHEN F,LI N,YANG X F,et al.Synthesis of high-density aviation fuel with cyclopentanol[J].Acs Sustainable Chemistry&Engineering,2016,4(11):6160-6166.
[43]LI S S,CHEN F,LI N,et al.Synthesis of renewable triketones,diketones,and jet-fuel range cycloalkanes with 5-hydroxymethylfurfural and ketones[J].Chem Sus Chem,2017,10(4):711-719.
[44]YAN K,JARVIS C,GU J,et al.Production and catalytic transformation of levulinic acid:a platform for speciality chemicals and fuels[J].Renewable&Sustainable Energy Reviews,2015,51:986-997.
[2]CLIMENT M J,CORMA A,IBORRA S.Conversion of biomass platform molecules into fuel additives and liquid hydrocarbon fuels[J].Green Chemistry,2014,16(2):516-547.
[3]RASMUSSEN H,SORENSEN H R,MEYER A S.Formation of deg rad ation compou nds f rom lig nocellulosic biomass i n the biorefi nery:sugar reaction mechanisms[J].Carbohydrate Research,2014,385:45-57.
[4]RUIZ H A,RODRIGUEZ-JASSO R M,FERNANDES B D,et al.Hydrothermal processing,as an alternative for upgrading agriculture residues and marine biomass according to the biorefinery concept:a review[J].Renewable&Sustainable Energy Reviews,2013,21(4):35-51.
[5]CHERUBINI F,STROMMAN A H.Chemicals from lignocellulosic biomass:opportunities,perspectives,and potential of biorefi nery systems[J].Biofuels Bioproducts&Biorefi ning-Biofpr,2011,5(5):548-561.
[6]石宁.木质纤维素催化转化制备呋喃类平台化合物及长链烷烃[D].北京:中国科学院大学,2015.
[7]ISIKGOR F H,BECER C R.Lignocellulosic biomass:a sustainable platform for the production of bio-based chemicals and polymers[J].Polymer Chemistry,2015,6(25):4497-4559.
[8]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.
[9]BALAKRISHNAN M,SACIA E R,BELL A T.Syntheses of biodiesel precursors:sulfonic acid catalysts for condensation of biomass-derived platform molecules[J].Chem Sus Chem,2014,7(4):1078-1085.
[10]ZHANG X,ZHANG Q,WANG T,et al.Hydrodeoxygenation of lignin-derived phenolic compounds to hydrocarbons over Ni/Si O2-Zr O2 catalysts[J].Bioresource Technology,2013,134:73-80.
[11]XU J M,XIE X F,WANG J X,et al.Directional liquefaction coupling f ractionation of lig nocellulosic biomass for platfor m chemicals[J].Green Chemistry,2016,18(10):3124-3138.
[12]WANG T,NOLTE M W,SHANKS B H.Catalytic dehydration of C6carbohydrates for the production of hydroxymethylfurfural(HMF)as a versatile platform chemical[J].Green Chemistry,2014,16(2):548-572.
[13]HAO W,LI W,TANG X,et al.Catalytic transfer hydrogenation of biomass-derived 5-hydroxymethyl furfural to the building block 2,5-bishydroxymethyl furan[J].Green Chemistry,2016,18(4):1080-1088.
[14]ZHANG Z,WANG Q,XIE H,et al.Catalytic conversion of carbohydrates into 5-hydroxymethylfurfural by germanium(IV)chloride in ionic liquids[J].Chem Sus Chem,2011,4(1):131-138.
[15]GUAN J,CAO Q,GUO X,et al.The mechanism of glucose conversion to 5-hydroxymethylfurfural catalyzed by metal chlorides in ionic liquid:a theoretical study[J].Computational and Theoretical Chemistry,2011,963(2-3):453-462.
[16]BINDER J B,CEFALI A V,BLANK J J,et al.Mechanistic insights on the conversion of sugars into 5-hydroxymethylfurfural[J].Energy&Environmental Science,2010,3(6):765-771.
[17]AMARASEKARA A S,WILLIAMS L D,EBEDE C C.Mechanism of t he dehyd r at ion of D-f r uctose to 5-hyd roxy met hylf u r f u r al in dimethyl sulfoxide at 150℃:an NMR study[J].Carbohydrate Research,2008,343(18):3021-3024.
[18]杨越,刘琪英,蔡炽柳,等.木质纤维素催化转化制备DMF和C5/C6烷烃[J].化学进展,2016,28(2-3):363-374.
[19]WAN J,LIAN J,WANG Y,et al.Investigation of cellulose supramolecular structure changes during conversion of waste paper in near-critical water on producing 5-hydroxymethyl furfural[J].Renewable Energy,2015,80:132-139.
[20]FRANCAVILLA M,INTINI S,LUCHETTI L,et al.Tunable microwave-assisted aqueous conversion of seaweed-derived agarose for the selective production of 5-hydroxymethyl furfural/levulinic acid[J].Green Chemistry,2016,18(22):5971-5977.
[21]STAHLBERG T,FU W J,WOODLEY J M,et al.Synthesis of 5-(hydroxymethyl)furfural in ionic liquids:paving the way to renewable chemicals[J].Chem Sus Chem,2011,4(4):451-458.
[22]KASHIN A S,GALKIN K I,KHOKHLOVA E A,et al.Direct observation of self-organized water-containing str uctures in the liquid phase and their inf luence on 5-(hydroxymethyl)furfural formation in ionic liquids[J].Angewandte Chemie-Inter national Edition,2016,55(6):2161-2166.
[23]DING Z D,SHI J C,XIAO J J,et al.Catalytic conversion of cellulose to 5-hydroxymethyl furfural using acidic ionic liquids and co-catalyst[J].Carbohydrate Polymers,2012,90(2):792-798.
[24]BINDER J B,RAINES R T.Simple chemical transformation of lignocellulosic biomass into furans for fuels and chemicals[J].Journal of the American Chemical Society,2009,131(5):1979-1985.
[25]石宁,刘琪英,王铁军,等.葡萄糖催化脱水制取5-羟甲基糠醛研究进展[J].化工进展,2012,31(4):792-800.
[26]SHI N,LIU Q Y,ZHANG Q,et al.High yield production of5-hydroxymethylfurfural from cellulose by high concentration of sulfates in biphasic system[J].Green Chemistry,2013,15(7):1967-1974.
[27]SHI N,LIU Q Y,MA L L,et al.Direct degradation of cellulose to5-hydroxymethylfurfural in hot compressed steam with inorganic acidic salts[J].Rsc Advances,2014,4(10):4978-4984.
[28]DENG W P,ZHANG Q H,WANG Y.Catalytic transformations of cellulose and its derived carbohydrates into 5-hydroxymethylfurfural, levulinic acid,and lactic acid[J].Sci China-Chem,2015,58(1):29-46.
[29]GAO H P,PENG Y X,PAN J M,et al.Synthesis and evaluation of macroporous polymerized solid acid derived from pickering HIPEs for catalyzing cellulose into 5-hydroxymethylfurfural in an ionic liquid[J].Rsc Advances,2014,4(81):43029-43038.
[30]THOMBAL R S,JADHAV V H.Biomass derived beta-cyclodextrinSO3H carbonaceous solid acid catalyst for catalytic conversion of carbohydrates to 5-hydroxymethylfurfural[J].Applied Catalysis A:General,2015,499:213-216.
[31]ZHANG Y,WANG J J,REN J W,et al.Mesoporous niobium phosphate:an excellent solid acid for the dehydration of fructose to 5-hyd roxy met hylf u r f u r al i n water[J].Cat alysis Science&Technology,2012,2(12):2485-2491.
[32]ZHAO S,CHENG M X,LI J Z,et al.One pot production of5-hyd roxy met hylf u r f u ral w it h h ig h y ield f rom cellulose by a bronsted-lewis-surfactant-combined heteropolyacid catalyst[J].Chemical Communications,2011,47(7):2176-2178.
[33]VAN PUTTEN R J,VAN DER WAAL J C,DE JONG E,et al.Hydroxymethylfurfural,a versatile platform chemical made from renewable resources[J].Chemical Reviews,2013,113(3):1499-1597.
[34]WANG T F,NOLTE M W,SHANKS B H.Catalytic dehydration of C6 carbohydrates for the production of hydroxymethylfurfural(HMF)as a versatile platform chemical[J].Green Chemistry,2014,16(2):548-572.
[35]VAN ZANDVOORT I,WANG Y H,RASRENDRA C B,et al.For mation,molecular str uct ure,and mor phology of humins i n biomass conversion:inf luence of feedstock and processing conditions[J].Chem Sus Chem,2013,6(9):1745-1758.
[36]袁正求,龙金星,张兴华,等.木质纤维素催化转化制备能源平台化合物[J].化学进展,2016,28(1):103-110.
[37]蔡炽柳,刘琪英,王铁军,等.木质生物质平台化合物催化转化制备长链烷烃的反应路径与催化剂研究进展[J].林产化学与工业,2015,35(6):153-162.
[38]HUBER G W,CHHEDA J N,BARRETT C J,et al.Production of liquid alkanes by aqueous-phase processing of biomass-derived carbohydrates[J].Science,2005,308(5727):1446-1450.
[39]XIN J Y,ZHANG S J,YAN D X,et al.Formation of C—C bonds for the production of bio-alkanes under mild conditions[J].Green Chemistry,2014,16(7):3589-3595.
[40]HUANG Y B,YANG Z,DAI J J,et al.Production of high quality fuels from lignocellulose-derived chemicals:a convenient C—C bond formation of furfural,5-methylfurfural and aromatic aldehyde[J].Rsc Advances,2012,2(30):11211-11214.
[41]CORMA A,DE LA TORRE O,RENZ M.Production of high quality diesel from cellulose and hemicellulose by the sylvan process:catalysts and process variables[J].Energy&Environmental Science,2012,5(4):6328-6344.
[42]CHEN F,LI N,YANG X F,et al.Synthesis of high-density aviation fuel with cyclopentanol[J].Acs Sustainable Chemistry&Engineering,2016,4(11):6160-6166.
[43]LI S S,CHEN F,LI N,et al.Synthesis of renewable triketones,diketones,and jet-fuel range cycloalkanes with 5-hydroxymethylfurfural and ketones[J].Chem Sus Chem,2017,10(4):711-719.
[44]YAN K,JARVIS C,GU J,et al.Production and catalytic transformation of levulinic acid:a platform for speciality chemicals and fuels[J].Renewable&Sustainable Energy Reviews,2015,51:986-997.