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木质纤维素催化转化制备DMF和C5/C6烷烃

杨越1,2, 刘琪英1, 蔡炽柳1,3, 谈金1, 王铁军1, 马隆龙1,2*

化学进展 ›› 2016, Vol. 28 ›› Issue (2/3) :363-374

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化学进展 ›› 2016, Vol. 28 ›› Issue (2/3) :363-374 DOI: 10.7536/PC150820
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木质纤维素催化转化制备DMF和C5/C6烷烃

    杨越1,2, 刘琪英1, 蔡炽柳1,3, 谈金1, 王铁军1, 马隆龙1,2*
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Advances in DMF and C5/C6 Alkanes Production from Lignocellulose

  • Yang Yue1,2, Liu Qiying1, Cai Chiliu1,3, Tan Jin1, Wang Tiejun1, Ma Longlong1,2*
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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;C5/C6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C5/C6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C5/C6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。

Abstract

Lignocellulosic biomass is an important renewable 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 C5/C6 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, C5/C6 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 C5/C6 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 biomass derived DMF and C5/C6 alkanes production is remarked and prospected.

Contents
1 Introduction
2 HMF from cellulose
2.1 Mechanism
2.2 Reaction medium
2.3 Catalysic system
2.4 Side reaction
3 DMF from HMF through selective hydrogenolysis
3.1 Mechanism
3.2 Reaction medium
3.3 Catalysic system
4 C5/C6 alkanes from cellulose
4.1 Pathway of alkanes
4.2 Catalysic system
5 Conclusion and outlook

Graphical abstract

关键词

纤维素 / DMF / HMF / C5/C6烷烃 / 催化剂 / 反应机理

Key words

cellulose / DMF / HMF / C5/C6 alkane / catalyst / reaction mechanism

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引用格式 ▾
杨越, 刘琪英, 蔡炽柳, 谈金, 王铁军, 马隆龙. 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 DOI:10.7536/PC150820
Yang Yue, Liu Qiying, Cai Chiliu, Tan Jin, Wang Tiejun, Ma Longlong. Advances in DMF and C5/C6 Alkanes Production from Lignocellulose[J]. Progress in Chemistry, 2016, 28(2/3): 363-374 DOI:10.7536/PC150820

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参考文献

[1] 张华(Zhang H), 魏晓平(Wei X P).北京理工大学学报(Journal of Beijing Institute of Technology), 2014, 16:42.
[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. ChemSusChem., 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. ChemSusChem., 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. ChemSusChem., 2010, 3:1071.
[43] Wang P, Yu H B, Zhan S H, Wang S Q. Bioresource Technol., 2011, 102:4179.
[44] McNeff C V, Nowlan D T, McNeff 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. ChemSusChem., 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. ChemSusChem., 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. ChemSusChem., 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. ChemSusChem., 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.
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