5-羟甲基糠醛（HMF）作为一种重要且多用途的生物质基平台化合物，可被转化为多种高附加值化学品，如乙酰丙酸、2，5-二甲基呋喃、2，5-呋喃二甲酸、2，5-呋喃二甲醇、γ-戊内酯、5-氨基乙酰丙酸等，而这些化学品可进一步作为化石燃料替代品、燃料添加剂或作为聚合物单体或医药产品等进行应用。葡萄糖是由纤维素水解大量得到的六碳单糖，由葡萄糖制备HMF是生物质资源最大化利用的有效途径之一。本文通过对近几年HMF制备方法的概述，分别由催化剂、反应体系两方面进行分类总结葡萄糖基碳水化合物制备HMF的研究进展，并对其各个反应过程的催化活性、反应体系稳定性和应用前景进行了总结归纳。随后论述了用于HMF制备的多种溶剂体系（诸如单相体系、双相体系、离子液体和低共熔溶剂体系）。最后，结合目前葡萄糖制备HMF过程中存在的问题，对未来工作的研究重点进行了展望，以期为相关研究者提供参考。
Biomass derived 5-hydroxymethylfurfural(HMF) has emerged as an important and versatile platform compound containing furan, hydroxymethyl and aldehyde groups to realize the goal for production of several high value added products, such as levulinic acid, 2,5-dimethylfuran, 2,5-furan dicarboxylic acid, 2,5-furan dimethanol, γ-valerolalactone, 5-aminolevulinic acid, which could be served as biofuels, fuel additives, bulk polymer monomers, chemicals and pharmaceuticals. Moreover, glucose is a bulk six-carbon monosaccharide from cellulose by hydrolyzation, and the preparation of HMF from glucose is one of the most effective and promising routes to maximize the utilization of sustainable biomass resources. In this review, focus is primarily put on the recent advances of systematically characterization on catalysts of HMF production from glucose for its activity, stability and application prospect. Then, the various solvent systems used in HMF production in recent years, such as single-phase solvents, biphasic solvents, ionic liquids and deep eutectic solvents, are reviewed and discussed. Finally, the future research directions such as an innovative catalyst, deep eutectic sol-vents are proposed, which might be helpful for researchers.
Contents
1 Introduction
2 Catalysts
2.1 Homogeneous catalysts
2.2 Heterogeneous catalysts
3 Reaction solvents
3.1 Single-phase solvents
3.2 Biphasic solvents
3.3 Ionic liquids
3.4 Deep eutectic solvents
4 Conclusion
[1] Corma A, Iborra S, Velty A. Chem. Rev., 2007, 107(6):2411.
[2] Huber G W, Iborra S, Corma A. Chem. Rev., 2006, 106(9):4044.
[3] Li C Z, Zhao X C, Wang A Q, Huber G W, Zhang T. Chem. Rev., 2015, 115(21):11559.
[4] Alonso D M, Bond J Q, Dumesic J A. Green Chem., 2010, 12(9):1493.
[5] Wang J J, Xi J X, Wang Y Q. Green Chem., 2015, 17(2):737.
[6] Kiermayer J. Chem. Ztg, 1895, 19:1003.
[7] Düll G. Chem. Ztg, 1895, 19:216.
[8] Van Enenstein W, Blanksma J. Chem. Weeklad, 1909, 6:717.
[9] Mascal M, Nikitin E B. Angew. Chem. Int. Ed., 2008, 47(41):7924.
[10] De S, Dutta S, Saha B. ChemSusChem, 2012, 5(9):1826.
[11] Roman-Leshkov Y, Barrett C J, Liu Z Y, Dumesic J A. Nature, 2007, 447(7147):982.
[12] Rosatella A A, Simeonov S P, Frade R F, Afonso C A. Green Chem., 2011, 13(4):754.
[13] Ståhlberg T, Fu W J, Woodley J M, Riisager A. ChemSusChem, 2011, 4(4):451.
[14] Wang H L, Kong Q Q, Wang Y X, Deng T S, Chen C M, Hou X L, Zhu Y L. ChemCatChem, 2014, 6(3):728.
[15] Hu Z, Liu B, Zhang Z H, Chen L Q. Ind. Crops Prod., 2013, 50:264.
[16] Yang Y, Hu C W, Abu-Omar M M. Green Chem., 2012, 14(2):509.
[17] Choudhary V, Mushrif S H, Ho C, Anderko A, Nikolakis V, Marinkovic N S, Frenkel A I, Sandler S I, Vlachos D G. J. Am. Chem. Soc., 2013, 135(10):3997.
[18] Loerbroks C, van Rijn J, Ruby M P, Tong Q, Schüth F, Thiel W. Chem. -Eur. J., 2014, 20(38):12298.
[19] Bhaumik P, Dhepe P L. Catal. Rev., 2016, 58(1):36.
[20] Yang Y, Hu C W, Abu-Omar M M. J. Mol. Catal. A:Chem., 2013, 376:98.
[21] Sarwono A, Man Z, Muhammad N, Khan A S, Hamzah W S W, Rahim A H A, Ullah Z, Wilfred C D. Ultrason. Sonochem., 2017, 37:310.
[22] Aida T M, Sato Y, Watanabe M, Tajima K, Nonaka T, Hattori H, Arai K. J. Supercrit. Fluids, 2007, 40(3):381.
[23] Qi X H, Watanabe M, Aida T M, Smith R L. Catal. Commun., 2008, 9(13):2244.
[24] Qi J, Lv X Y. Chin. J. Chem. Eng., 2008, 16(6):890.
[25] Cole-Hamilton D J. Science, 2003, 299(5613):1702.
[26] Li M H, Li W Z, Lu Y J, Jameel H, Chang H M, Ma L L. RSC Adv., 2017, 7(24):14330.
[27] Pagan-Torres Y J, Wang T F, Gallo J M R, Shanks B H, Dumesic J A. ACS Catal., 2012, 2(6):930.
[28] Eminov S, Brandt A, Wilton-Ely J D, Hallett J P. PLoS One, 2016, 11(10):e0163835.
[29] Teng J J, Ma H, Wang F R, Wang L F, Li X H. Bioresources, 2016, 11(1):2152.
[30] Xu Z L, Wang X Y, Shen M Y, Du C H. Chem. Pap., 2016, 70(12):1649.
[31] Zhou J X, Xia Z, Huang T Y, Yan P F, Xu W J, Xu Z W, Wang J J, Zhang Z C. Green Chem., 2015, 17(8):4206.
[32] Li J J, Ma Y B, Wang L, Song Z, Li H P, Wang T F, Li H Y, Eli W. Catalysts, 2015, 6(1):1.
[33] Di Serio M, Tesser R, Lu P M, Santacesaria E. Energy Fuels, 2007, 22(1):207.
[34] Nasirudeen M B, Hailes H C, Evans J R G. Curr. Org. Synth., 2017, 14(4):596.
[35] Yan H P, Yang Y, Tong D M, Xiang X, Hu C W. Catal. Commun., 2009, 10(11):1558.
[36] 于世涛(Yu S T), 刘福胜(Liu F S). 固体酸与精细化工(Solid Acid and Fine Chemical Industry), 北京:化学工业出版社(Beijing:Chemical Industry Press), 2006. 23.
[37] Wang Y P, Liu Y H, Yang L, Ruan R, Wen P W, Wan Y Q. Synth. React. Inorg. Met.-Org. Chem., 2016, 46(2):177.
[38] García-Sancho C, Fúnez-Núñez I, Moreno-Tost R, Santamaría-González J, Pérez-Inestrosa E, Fierro J L G, Maireles-Torres P. Appl. Catal. B-Environ., 2017, 206:617.
[39] Jiao H F, Zhao X L, Lv C X, Wang Y J, Yang D J, Li Z H, Yao X D. Sci. Rep., 2016, 6.
[40] Martínez J J, Silva D F, Aguilera E X, Rojas H A, Brijaldo M H, Passos F B, Romanelli G P. Catal. Lett., 2017, 147(7):1765.
[41] Guo J, Zhu S H, Cen Y L, Qin Z F, Wang J G, Fan W B. Appl. Catal. B-Environ., 2017, 200:611.
[42] Yue C C, Li G N, Pidko E A, Wiesfeld J J, Rigutto M, Hensen E J. ChemSusChem, 2016, 9(17):2421.
[43] Su Y, Chang G G, Zhang Z G, Xing H B, Su B G, Yang Q W, Ren Q L, Yang Y W, Bao Z B. AIChE J., 2016, 62(12):4403.
[44] Yabushita M, Li P, Islamoglu T, Kobayashi H, Fukuoka A, Farha O K, Katz A. Ind. Eng. Chem. Res., 2017, 56(25):7141.
[45] Chen D W, Liang F B, Feng D X, Xian M, Zhang H B, Liu H Z, Du F L. Chem. Eng. J., 2016, 300:177.
[46] Li W Z, Zhang T W, Xin H S, Su M X, Ma L L, Jameel H, Chang H M, Pei G. RSC Adv., 2017, 7(44):27682.
[47] Thombal R S, Jadhav V H. Appl. Catal., A, 2015, 499:213.
[48] Jiménez-Morales I, Santamaría-González J, Jiménez-López A, Maireles-Torres P. Fuel, 2014, 118:265.
[49] Jiménez-Morales I, Moreno-Recio M, Santamaría-González J, Maireles-Torres P, Jimenez-Lopez A. Appl. Catal. B-Environ., 2015, 164:70.
[50] Xu Q, Zhu Z, Tian Y K, Deng J, Shi J, Fu Y. Bioresources, 2013, 9(1):303.
[51] Moreno-Recio M, Santamaría-González J, Maireles-Torres P. Chem. Eng. J., 2016, 303:22.
[52] Wang P, Ren L H, Lu Q Y, Huang Y B. Chem. Eng. Commun., 2016, 203(11):1507.
[53] Liu H, Wang H W, Li Y, Yang W, Song C H, Li H M, Zhu W S, Jiang W. RSC Adv., 2015, 5(12):9290.
[54] Ravasco J M J M, Coelho J A S, Simeonov S P, Afonso C A M. RSC Adv., 2017, 7(13):7555.
[55] Lu Y M, Li H, He J, Liu Y X, Wu Z B, Hu D Y, Yang S. RSC Adv., 2016, 6(16):12782.
[56] Liu B, Ba C, Jin M M, Zhang Z H. Ind. Crops Prod., 2015, 76:781.
[57] Wang J J, Ren J W, Liu X H, Xi J X, Xia Q N, Zu Y H, Lu G Z, Wang Y Q. Green Chem., 2012, 14(9):2506.
[58] Guo X Q, Zhu C H, Guo F. Bioresources, 2016, 11(1):2457.
[59] Gascon J, Corma A, Kapteijn F, Llabrés i Xamena F X. ACS Catal., 2013, 4(2):361.
[60] Lee J, Farha O K, Roberts J, Scheidt K A, Nguyen S T, Hupp J T. Chem. Soc. Rev., 2009, 38(5):1450.
[61] Valvekens P, Vermoortele F, De Vos D. Catal. Sci. Technol., 2013, 3(6):1435.
[62] Herbst A, Janiak C. New J. Chem., 2016, 40(9):7958.
[63] Mondloch J E, Bury W, Fairen-Jimenez D, Kwon S, DeMarco E J, Weston M H, Sarjeant A A, Nguyen S T, Stair P C, Snurr R Q, Farha O K, Hupp J T. J. Am. Chem. Soc., 2013, 135(28):10294.
[64] Kruse A, Dinjus E. J. Supercrit. Fluids, 2007, 39(3):362.
[65] Shuai L, Luterbacher J. ChemSusChem, 2016, 9(2):133.
[66] Kimura H, Nakahara M, Matubayasi N. J. Phys. Chem. A, 2011, 115(48):14013.
[67] Vasudevan V, Mushrif S H. RSC Adv., 2015, 5(27):20756.
[68] Sun J K, Yuan X D, Shen Y, Yi Y X, Wang B, Xu F, Sun R C. Ind. Crops Prod., 2015, 70:266.
[69] Girisuta B, Janssen L P B M, Heeres H J. Chem. Eng. Res. Des., 2006, 84(5):339.
[70] Gürbüz E I, Wettstein D S G, Dumesic P J A. ChemSusChem, 2012, 5(2):383.
[71] Román-Leshkov Y, Dumesic J A. Top. Catal., 2009, 52(3):297.
[72] Binder J B, Raines R T. J. Am. Chem. Soc., 2009, 131(5):1979.
[73] Wasserscheid P, Keim W. Angew. Chem. Int. Ed., 2000, 39(21):3772.
[74] Rogers R D, Seddon K R. Science, 2003, 302(5646):792.
[75] 胡磊(Hu L), 孙勇(Sun Y), 林鹿(Lin L). 化学进展(Progress in Chemistry), 2012, 24(4):483.
[76] Zhao H B, Holladay J E, Brown H, Zhang Z C. Science, 2007, 316(5831):1597.
[77] Li C Z, Zhang Z H, Zhao Z B K. Tetrahedron Lett., 2009, 50(38):5403.
[78] D'Anna F, Marullo S, Vitale P, Rizzo C, Meo P L, Noto R. Appl. Catal. A, 2014, 482(28):287.
[79] Tang X, Zuo M, Li Z, Liu H, Xiong C X, Zeng X H, Sun Y, Hu L, Liu S J, Lei T Z, Lin L. ChemSusChem, 2017, 10(13):2696.
[80] Paiva A, Craveiro R, Aroso I, Martins M, Reis R L, Duarte A R C. ACS Sustain Chem. Eng., 2014, 2(5):1063.
[81] Matsumiya H, Hara T. Biomass Bioenerg., 2015, 72:227.
[82] Zuo M, Le K, Li Z, Jiang Y T, Zeng X H, Tang X, Sun Y, Lin L. Ind. Crops Prod., 2017, 99:1.
[83] Liu F, Audemar M, Vigier K D O, Cartigny D, Clacens J M, Gomes M F C, Pádua A A, De Campo F, Jérôme F. Green Chem., 2013, 15(11):3205.
[84] Ilgen F, Ott D, Kralisch D, Reil C, Palmberger A, König B. Green Chem., 2009, 11(12):1948.
[85] Yang J, De Oliveira Vigier K, Gu Y L, Jerome F. ChemSusChem, 2015, 8(2):269.
PDF
(1408KB)
