木质纤维素催化转化制备DMF和C_5/C_6烷烃
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摘要
生物质是一类重要的可再生资源,将其转化为高品质燃料在能源替代、环境保护等方面具有重要意义。在高品质燃料中,2,5-二甲基呋喃(DMF)具有较高的能量密度、高辛烷值和较高的沸点,是一种非常具有应用前景的可再生含氧液体燃料,掺混后可促进汽油的燃烧;C_5/C_6烷烃是现有汽油的重要组分,在提高汽油辛烷值和调节蒸汽压等方面不可或缺。本文以木质纤维素生物质典型组分纤维素为起始原料,系统总结了纤维素转化为5-羟甲基糠醛(HMF),HMF选择性加氢脱氧为DMF以及完全加氢脱氧为C_5/C_6液体烷烃等转化过程的反应介质、催化体系及反应路径。反应介质包括水、离子液体、极性非质子有机溶剂、含水的双相体系;催化体系包括无机酸、金属盐、固体酸及负载型催化剂。本文对DMF和C_5/C_6烷烃液体燃料高效合成的研究前景进行了展望和评述,以期为纤维素类生物质高效转化为高值液体燃料提供思路和参考。
Lignocellulosic biomass is an important renew able resource,and has potential application in high quality biofuels to substitute fossil energy and reduce green house gas emission. Among those high quality biofuels,oxygen-contained 2,5-dimethyl furan( DMF) and C_5/C_6 alkanes show particular interests because these two kinds fuels could be produced from biomass via 5-hydroxymethyl furfural( HMF) intermediate. DMF is an ideal replacement and/or dopant for the presently used gasoline by enhancing combustion efficiency and reducing contaminant emission because of its higher energy density,higher octane number and higher boiling point. On the other hand,C_5/C_6 alkanes are the important gasoline components for adjusting the octane number and volatile properties. In this paper,combining our studies,we systematically summarize the status-of-the-art technologies for HMF synthesis from cellulose, and DMF and C_5/C_6 alkanes production by selective and complete hydrodeoxygenation of HMF respectively,depended on reaction medium,catalyst and pathway. The reaction mediums include water,ionic liquid,polar aprotic organic solvent and water contained biphasic solvent; and catalysts include inorganic acid,metal salt,solid acid and supported catalyst. Finally,the future of biomassderived DMF and C_5/C_6 alkanes production is remarked and prospected.
Lignocellulosic biomass is an important renew able resource,and has potential application in high quality biofuels to substitute fossil energy and reduce green house gas emission. Among those high quality biofuels,oxygen-contained 2,5-dimethyl furan( DMF) and C_5/C_6 alkanes show particular interests because these two kinds fuels could be produced from biomass via 5-hydroxymethyl furfural( HMF) intermediate. DMF is an ideal replacement and/or dopant for the presently used gasoline by enhancing combustion efficiency and reducing contaminant emission because of its higher energy density,higher octane number and higher boiling point. On the other hand,C_5/C_6 alkanes are the important gasoline components for adjusting the octane number and volatile properties. In this paper,combining our studies,we systematically summarize the status-of-the-art technologies for HMF synthesis from cellulose, and DMF and C_5/C_6 alkanes production by selective and complete hydrodeoxygenation of HMF respectively,depended on reaction medium,catalyst and pathway. The reaction mediums include water,ionic liquid,polar aprotic organic solvent and water contained biphasic solvent; and catalysts include inorganic acid,metal salt,solid acid and supported catalyst. Finally,the future of biomassderived DMF and C_5/C_6 alkanes production is remarked and prospected.
引文
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[78]Shi N,Liu Q Y,Wang T J,Zhang Q,Tu J L,Ma L L.Chin.J.Chem.Phys.,2014,27:711.
[2]王晓明(Wang X M),唐兰(Tang L),赵黛青(Zhao D Q),郝海清(Hao H Q),王欢(Wang H),王云鹤(Wang Y H),朱赤晖(Zhu C H).环境影响评价(Environmental Impact Assessment),2010,32:38.
[3]Corma A,Iborra S,Velty A.Chem.Rev.,2007,107:2411.
[4]胡磊(Hu L),孙勇(Sun Y),林鹿(Lin L).化学进展(Progress in Chemistry),2011,23:2079.
[5]Climent M J,Corma A,Iborra S.Green Chem.,2014,16:516.
[6]王军(Wang J),张春鹏(Zhang C P),欧阳平凯(Ouyang P K).化工进展(Chemical Industry and Engineering Progress),2008,27:702.
[7]Zhao H B,Holladay J E,Science,2007,316:1597.
[8]Binder J B,Cefali A V,Blank J J,Raines R T.Energy Environ.Sci.,2010,3:765.
[9]Antal M J,Mok W S L,Richards G N.Carbohydr.Res.,1990,199:91.
[10]Guan J,Cao Q A,Guo X C,Mu X D.Comput.Theor.Chem.,2011,963:453.
[11]Amarasekara A S,Williams L D.Carbohyd Res.,2008,343:3021.
[12]Asghari F S,Yoshida H.Carbohyd Res.,2006,341:2379.
[13]Ohno H,Fukaya Y.Chem.Lett.,2009,38:2.
[14]Li C Z,Zhang Z H,Zhao Z B K.Tetrahedron Lett.,2009,50:5403.
[15]Ding Z D,Shi J C,Xiao J J,Gu W X,Zheng C G,Wang H J.Carbohyd Polym.,2012,90:792.
[16]Binder J B,Raines R T.J.Am.Chem.Soc.,2009,131:1979.
[17]Chen T M,Lin L.Chinese.J.Chem.,2010,28:1773.
[18]Yan H P,Yang Y,Tong D M,Xiang X,Hu C W.Catal.Commun.,2009,10:1558.
[19]Bicker M,Hirth J,Vogel H.Green Chem.,2003,5:280.
[20]Yamaguchi K,Sakurada T,Ogasawara Y,Mizuno N.Chem.Lett.,2011,40:542.
[21]Hansen T S,Mielby J,Riisager A.Green Chem.,2011,13:109.
[22]Yang F L,Liu Q S,Bai X F,Du Y G.Bioresource Technol.,2011,102:3424.
[23]Nikolla E,Roman-Leshkov Y,Moliner M,Davis M E.ACS Catal.,2011,1:408.
[24]Yang Y,Hu C W,Abu-Omar M M.Green Chem.,2012,14:509.
[25]Shi N,Liu Q Y,Zhang Q,Wang T J,Ma L L.Green Chem.,2013,15(7):1967.
[26]Roman-Leshkov Y,Barrett C J,Liu Z Y,Dumesic J A.Nature,2007,447(7147):982.
[27]Girisuta B,Janssen L P B M,Heeres H J.Chem.Eng.Res.Des.,2006,84:339.
[28]Xiang Q,Lee Y Y,Torget R W.Appl.Biochem.Biotechnol.,2004,113:1127.
[29]Chheda J N,Roman-Leshkov Y,Dumesic J A.Green Chem.,2007,9:342.
[30]Zhang Z H,Wang Q A,Xie H B,Liu W J,Zhao Z B.Chem Sus Chem.,2011,4:131.
[31]Zheng B H,Fang Z J,Cheng J,Jiang Y H.Naturforsch.,B:Chem.Sci.,2010,65:168.
[32]Deng T S,Cui X J,Qi Y Q,Wang Y X,Hou X L,Zhu Y L.Chem.Commun.,2012,48:5494.
[33]Moliner M,Roman-Leshkov Y,Davis M E.Natl.Acad.Sci.U.S.A.,2010,107:6164.
[34]Yang F L,Liu Q S,Yue M,Bai X F,Du Y G.Chem.Commun.,2011,47:4469.
[35]Zhao Q A,Wang L,Zhao S,Wang X H,Wang S T.Fuel,2011,90:2289.
[36]Qi X H,Watanabe M,Aida T M,Smith R L.Chem Sus Chem.,2010,3:1071.
[37]Zhao S,Cheng M X,Li J Z,Tian J A,Wang X H.Chem Commun.,2011,47:2176.
[38]Ehara K,Saka S.J.Wood Sci.,2005,51:148.
[39]Asghari F S,Yoshida H.Carbohyd Res.,2010,345:124.
[40]Tan M X,Zhao L,Zhang Y G.Biomass Bioenerg.,2011,35:1367.
[41]Yu S,Brown H M,Huang X W,Zhou X D,Amonette J E,Zhang Z C.Appl.Catal.A,Gen.,2009,361:117.
[42]Qi X H,Watanabe M,Aida T M,Smith R L.Chem Sus Chem.,2010,3:1071.
[43]Wang P,Yu H B,Zhan S H,Wang S Q.Bioresource Technol.,2011,102:4179.
[44]Mc Neff C V,Nowlan D T,Mc Neff L C,Yan B W,Fedie R L.Appl.Catal.A,Gen.,2010,384:65.
[45]Horvat J,Klaic B,Metelko B,Sunjic V.Tetrahedron Lett.,1985,26:2111.
[46]Dee S J,Bell A T.Chem Sus Chem.,2011,4:1166.
[47]Patil S K R,Lund C R F.Energ.Fuel,2011,25:4745.
[48]Sumerskii I V,Krutov S M,Zarubin M Y.Russ.J.Appl.Chem.,2010,83:320.
[49]Hu L,Lin L,Liu S J.Ind Eng Chem Res.,2014,53:9969.
[50]Tamura M,Tokonami K,Nakagawa Y,Tomishige K.Chem Commun.,2013,49:7034.
[51]Chidambaram M,Bell A T.Green Chem.,2010,12:1253.
[52]Thananatthanachon T,Rauchfuss T B.Agnew.Chem.Int.Ed.,2010,49(37):6616.
[53]Jae J,Zheng W Q,Lobo R F,Vlachos D G.Chem Sus Chem.,2013,6:1158.
[54]Wang J J,Liu X H,Hu B C,Lu G Z,Wang Y Q.RSC Adv.,2014,4:31101.
[55]Zu Y H,Yang P P,Wang J J,Liu X H,Ren J W,Lu G Z,Wang Y Q.Appl.Catal.B,Environ.,2014,146:244.
[56]Huang Y B,Chen M Y,Yan L,Guo Q X,Fu Y.Chem Sus Chem.,2014,7:1068.
[57]Kong X,Zhu Y F,Zheng H Y,Dong F,Zhu Y L,Li Y W.RSC Adv.,2014,4:60467.
[58]Zhang J H,Lin L,Liu S J.Energ.Fuel,2012,26:4560.
[59]Saha B,Bohn C M,Abu-Omar M M.Chem Sus Chem.,2014,7:3095.
[60]Yang P P,Cui Q Q,Zu Y H,Liu X H,Lu G Z,Wang Y Q.Catal.Commun.,2015,66:55.
[61]Huber G W,Dumesic J A.Catal.Today,2006,111:119.
[62]Li N,Huber G W.J.Catal.,2010,270:48.
[63]Zhang Q,Wang T J,Li B,Jiang T,Ma L L,Zhang X H,Liu Q Y.Appl.Energ.,2012,97:509.
[64]Zhang Q,Qiu K,Li B,Jiang T,Zhang X H,Ma L L,Wang T J.Fuel,2011,90:3468.
[65]de Beeck B O,Dusselier M,Geboers J,Holsbeek J,Morre E,Oswald S,Giebeler L,Sels B F.Energy Environ.Sci.,2015,8:230.
[66]Huber G W,Cortright R D,Dumesic J A.Angew.Chem.Int.Ed.,2004,43:1549.
[67]West R M,Tucker M H,Braden D J,Dumesic J A.Catal.Commun.,2009,10:1743.
[68]Davda R R,Shabaker J W,Huber G W,Cortright R D,Dumesic J A.Appl.Catal.B,Environ.,2005,56:171.
[69]Kunkes E L,Simonetti D A,West R M,Serrano-Ruiz J C,Gartner C A,Dumesic J A.Science,2008,322:417.
[70]Liu S B,Tamura M,Nakagawa Y,Tomishige K.ACS Sustain.Chem.Eng.,2014,2:1819.
[71]Liu Y,Chen L G,Wang T J,Zhang X H,Long J X,Zhang Q,Ma L L.Rsc Adv.,2015,5:11649.
[72]Dutta S,Pal S.Biomass Bioenerg.,2014,62:182.
[73]Anet E F L J.Adv.Carbohyd.Chem.,1964,19:181.
[74]Li C Z,Zhao Z B K,Cai H L,Wang A Q,Zhang T.Biomass Bioenerg.,2011,35:2013.
[75]Takagaki A,Ohara M,Nishimura S,Ebitani K.Chem Commun.,2009,41:6276.
[76]Ohara M,Takagaki A,Nishimura S,Ebitani K.Appl.Catal.A,Gen.,2010,383:149.
[77]Li C Z,Cai H L,Zhang B,Li W Z,Pei G X,Dai T,Wang A Q,Zhang T.Chin.J.Catal.,2015,36:1638.
[78]Shi N,Liu Q Y,Wang T J,Zhang Q,Tu J L,Ma L L.Chin.J.Chem.Phys.,2014,27:711.