Abstract
With concerns of diminishing fossil fuel reserves and environmental deterioration, great efforts have been made to explore novel approaches of efficiently utilizing bio-renewable feedstocks to produce chemicals and fuels. 5-Hydroxymethylfurfural (HMF), generated from dehydration of six-carbon ketose, is regarded as a primary and versatile renewable building block to realize the goal of production of these high valued products from renewable biomass resources transformation. In this review, we summarize the recent advances via green routes in the heterogeneous reaction system for the catalytic production of HMF from glucose conversion, and emphasize reaction pathways of these reaction approaches based on the fundamental mechanistic chemistry as well as highlight the challenges (such as separation and purification of products, reusing and regeneration of catalyst, recycling solvent) in this field.
References
Cai H, Li C, Wang A, Zhang T. Catal Today, 2014, 234: 59–65
Delidovich I, Palkovits R. ChemSusChem, 2016, 9: 547–561
Deng W, Zhang Q, Wang Y. Catal Today, 2014, 234: 31–41
Farrán A, Cai C, Sandoval M, Xu Y, Liu J, Hernáiz MJ, Linhardt RJ. Chem Rev, 2015, 115: 6811–6853
Liu X, Wang X, Yao S, Jiang Y, Guan J, Mu X. RSC Adv, 2014, 4: 49501–49520
Luterbacher JS, Martin Alonso D, Dumesic JA. Green Chem, 2014, 16: 4816–4838
Wang L, Xiao FS. Green Chem, 2015, 17: 24–39
Zhang X, Wilson K, Lee AF. Chem Rev, 2016, 116: 12328–12368
Caratzoulas S, Davis ME, Gorte RJ, Gounder R, Lobo RF, Nikolakis V, Sandler SI, Snyder MA, Tsapatsis M, Vlachos DG. J Phys Chem C, 2014, 118: 22815–22833
Chatterjee C, Pong F, Sen A. Green Chem, 2015, 17: 40–71
Wang J, Xi J, Wang Y. Green Chem, 2015, 17: 737–751
Rosatella AA, Simeonov SP, Frade RFM, Afonso CAM. Green Chem, 2011, 13: 754–793
Chinnappan A, Baskar C, Kim H. RSC Adv, 2016, 6: 63991–64002
Saha B, Abu-Omar MM. Green Chem, 2014, 16: 24–38
Teong SP, Yi G, Zhang Y. Green Chem, 2014, 16: 2015–2026
Wang T, Nolte MW, Shanks BH. Green Chem, 2014, 16: 548–572
Xue Z, Ma MG, Li Z, Mu T. RSC Adv, 2016, 6: 98874–98892
Chheda JN, Huber GW, Dumesic JA. Angew Chem Int Ed, 2007, 46: 7164–7183
Tong X, Ma Y, Li Y. Appl Catal A-Gen, 2010, 385: 1–13
Assary RS, Curtiss LA. Energy Fuels, 2012, 26: 1344–1352
Boronat M, Concepcion P, Corma A, Renz M, Valencia S. J Catal, 2005, 234: 111–118
Li G, Pidko EA, Hensen EJM. ACS Catal, 2016, 6: 4162–4169
Li J, Li J, Zhang D, Liu C. J Phys Chem B, 2015, 119: 13398–13406
Li YP, Head-Gordon M, Bell AT. ACS Catal, 2014, 4: 1537–1545
Loerbroks C, van Rijn J, Ruby MP, Tong Q, Schüth F, Thiel W. Chem Eur J, 2014, 20: 12298–12309
Pidko EA, Degirmenci V, Hensen EJM. ChemCatChem, 2012, 4: 1263–1271
Pidko EA, Degirmenci V, van Santen RA, Hensen EJM. Angew Chem Int Ed, 2010, 49: 2530–2534
Qian X. J Phys Chem B, 2013, 117: 11460–11465
Qian X, Wei X. J Phys Chem B, 2012, 116: 10898–10904
Rai N, Caratzoulas S, Vlachos DG. ACS Catal, 2013, 3: 2294–2298
Saravanamurugan S, Riisager A, Taarning E, Meier S. ChemCatChem, 2016, 8: 3107–3111
Yang G, Pidko EA, Hensen EJM. ChemSusChem, 2013, 6: 1688–1696
Yang L, Tsilomelekis G, Caratzoulas S, Vlachos DG. ChemSusChem, 2015, 8: 1334–1341
Zhang ZC. Adv Catal, 2006, 49: 153–237
Zhao H, Holladay JE, Brown H, Zhang ZC. Science, 2007, 316: 1597–1600
Fenn TD, Ringe D, Petsko GA. Biochemistry, 2004, 43: 6464–6474
Moliner M, Román-Leshkov Y, Davis ME. Proc Natl Acad Sci USA, 2010, 107: 6164–6168
Nikolla E, Román-Leshkov Y, Moliner M, Davis ME. ACS Catal, 2011, 1: 408–410
Román-Leshkov Y, Moliner M, Labinger JA, Davis ME. Angew Chem Int Ed, 2010, 49: 8954–8957
Bermejo-Deval R, Gounder R, Davis ME. ACS Catal, 2012, 2: 2705–2713
Bermejo-Deval R, Assary RS, Nikolla E, Moliner M, Román-Leshkov Y, Hwang SJ, Palsdottir A, Silverman D, Lobo RF, Curtiss LA, Davis ME. Proc Natl Acad Sci USA, 2012, 109: 9727–9732
Yu Y, Wu H. Ind Eng Chem Res, 2011, 50: 10500–10508
Aida TM, Sato Y, Watanabe M, Tajima K, Nonaka T, Hattori H, Arai K. J Supercrit Fluid, 2007, 40: 381–388
Lee YC, Chen CT, Chiu YT, Wu KCW. ChemCatChem, 2013, 5: 2153–2157
Vennestrøm PNR, Christensen CH, Pedersen S, Grunwaldt JD, Woodley JM. ChemCatChem, 2010, 2: 249–258
Huang R, Qi W, Su R, He Z. Chem Commun, 2010, 46: 1115–1117
Grande PM, Bergs C, Domínguez de María P. ChemSusChem, 2012, 5: 1203–1206
Simeonov SP, Coelho JAS, Afonso CAM. ChemSusChem, 2013, 6: 997–1000
Huang H, Denard CA, Alamillo R, Crisci AJ, Miao Y, Dumesic JA, Scott SL, Zhao H. ACS Catal, 2014, 4: 2165–2168
Delidovich I, Palkovits R. Catal Sci Technol, 2014, 4: 4322–4329
Liu C, Carraher JM, Swedberg JL, Herndon CR, Fleitman CN, Tessonnier JP. ACS Catal, 2014, 4: 4295–4298
Yang Q, Sherbahn M, Runge T. ACS Sustain Chem Eng, 2016, 4: 3526–3534
Yang Q, Zhou S, Runge T. J Catal, 2015, 330: 474–484
Watanabe M, Aizawa Y, Iida T, Aida TM, Levy C, Sue K, Inomata H. Carbohyd Res, 2005, 340: 1925–1930
Qi X, Watanabe M, Aida TM, Smith Jr RL. Catal Commun, 2008, 9: 2244–2249
Ohara M, Takagaki A, Nishimura S, Ebitani K. Appl Catal A-Gen, 2010, 383: 149–155
Takagaki A, Ohara M, Nishimura S, Ebitani K. Chem Commun, 2009: 6276–6278
Yu S, Kim E, Park S, Song IK, Jung JC. Catal Commun, 2012, 29: 63–67
Despax S, Estrine B, Hoffmann N, Le Bras J, Marinkovic S, Muzart J. Catal Commun, 2013, 39: 35–38
Román-Leshkov Y, Davis ME. ACS Catal, 2011, 1: 1566–1580
Cao Q, Guo X, Yao S, Guan J, Wang X, Mu X, Zhang D. Carbohyd Res, 2011, 346: 956–959
Hu L, Sun Y, Lin L. Ind Eng Chem Res, 2012, 51: 1099–1104
Liu W, Holladay J. Catal Today, 2013, 200: 106–116
Pidko EA, Degirmenci V, van Santen RA, Hensen EJM. Inorg Chem, 2010, 49: 10081–10091
Binder JB, Cefali AV, Blank JJ, Raines RT. Energy Environ Sci, 2010, 3: 765–771
Zhang Y, Pidko EA, Hensen EJM. Chem Eur J, 2011, 17: 5281–5288
He J, Zhang Y, Chen EYX. ChemSusChem, 2013, 6: 61–64
Yong G, Zhang Y, Ying JY. Angew Chem Int Ed, 2008, 47: 9345–9348
Qi X, Watanabe M, Aida TM, Smith Jr RL. ChemSusChem, 2010, 3: 1071–1077
Zhang Z, Zhao ZK. Bioresource Tech, 2011, 102: 3970–3972
Degirmenci V, Pidko EA, Magusin PCMM, Hensen EJM. ChemCatChem, 2011, 3: 969–972
Choudhary V, Mushrif SH, Ho C, Anderko A, Nikolakis V, Marinkovic NS, Frenkel AI, Sandler SI, Vlachos DG. J Am Chem Soc, 2013, 135: 3997–4006
Pagán-Torres YJ, Wang T, Gallo JMR, Shanks BH, Dumesic JA. ACS Catal, 2012, 2: 930–934
Zhou X, Zhang Z, Liu B, Xu Z, Deng K. Carbohyd Res, 2013, 375: 68–72
Deng T, Cui X, Qi Y, Wang Y, Hou X, Zhu Y. Chem Commun, 2012, 48: 5494–5496
Zhang Z, Wang Q, Xie H, Liu W, Zhao ZK. ChemSusChem, 2011, 4: 131–138
Zhang Z, Liu B, Zhao ZK. Starch-Stärke, 2012, 64: 770–775
Hu S, Zhang Z, Song J, Zhou Y, Han B. Green Chem, 2009, 11: 1746–1749
Assary RS, Redfern PC, Hammond JR, Greeley J, Curtiss LA. J Phys Chem B, 2010, 114: 9002–9009
Ding D, Wang J, Xi J, Liu X, Lu G, Wang Y. Green Chem, 2014, 16: 3846–3853
Upare PP, Yoon JW, Kim MY, Kang HY, Hwang DW, Hwang YK, Kung HH, Chang JS. Green Chem, 2013, 15: 2935–2943
Weingarten R, Cho J, Xing R, Conner Jr WC, Huber GW. ChemSusChem, 2012, 5: 1280–1290
Weingarten R, Kim YT, Tompsett GA, Fernández A, Han KS, Hagaman EW, Conner Jr WC, Dumesic JA, Huber GW. J Catal, 2013, 304: 123–134
Liu B, Zhang Z. RSC Adv, 2013, 3: 12313–12319
Liu B, Zhang Z, Huang K, Fang Z. Fuel, 2013, 113: 625–631
Peng L, Lin L, Zhang J, Shi J, Liu S. Appl Catal A-Gen, 2011, 397: 259–265
Saravanamurugan S, Riisager A. ChemCatChem, 2013, 5: 1754–1757
Saravanamurugan S, Nguyen Van Buu O, Riisager A. ChemSusChem, 2011, 4: 723–726
Chang CC, Wang Z, Dornath P, Je Cho H, Fan W. RSC Adv, 2012, 2: 10475–10477
Dijkmans J, Gabriëls D, Dusselier M, de Clippel F, Vanelderen P, Houthoofd K, Malfliet A, Pontikes Y, Sels BF. Green Chem, 2013, 15: 2777–2785
Corma A, Domine ME, Nemeth L, Valencia S. J Am Chem Soc, 2002, 124: 3194–3195
Roy S, Bakhmutsky K, Mahmoud E, Lobo RF, Gorte RJ. ACS Catal, 2013, 3: 573–580
Lew CM, Rajabbeigi N, Tsapatsis M. Micropor Mesopor Mater, 2012, 153: 55–58
Saravanamurugan S, Paniagua M, Melero JA, Riisager A. J Am Chem Soc, 2013, 135: 5246–5249
Zhang L, Xi G, Chen Z, Qi Z, Wang X. Chem Eng J, 2017, 307: 877–883
Gardner DW, Huo J, Hoff TC, Johnson RL, Shanks BH, Tessonnier JP. ACS Catal, 2015, 5: 4418–4422
Otomo R, Yokoi T, Tatsumi T. ChemCatChem, 2015, 7: 4180–4187
Faria J, Pilar Ruiz M, Resasco DE. ACS Catal, 2015, 5: 4761–4771
Wang J, Ren J, Liu X, Xi J, Xia Q, Zu Y, Lu G, Wang Y. Green Chem, 2012, 14: 2506–2512
Osatiashtiani A, Lee AF, Brown DR, Melero JA, Morales G, Wilson K. Catal Sci Technol, 2014, 4: 333–342
Dutta A, Patra AK, Dutta S, Saha B, Bhaumik A. J Mater Chem, 2012, 22: 14094–14100
Atanda L, Mukundan S, Shrotri A, Ma Q, Beltramini J. ChemCatChem, 2015, 7: 781–790
Dutta A, Gupta D, Patra AK, Saha B, Bhaumik A. ChemSusChem, 2014, 7: 925–933
Ordomsky VV, van der Schaaf J, Schouten JC, Nijhuis TA. ChemSusChem, 2013, 6: 1697–1707
Ordomsky VV, Sushkevich VL, Schouten JC, van der Schaaf J, Nijhuis TA. J Catal, 2013, 300: 37–46
Osatiashtiani A, Lee AF, Granollers M, Brown DR, Olivi L, Morales G, Melero JA, Wilson K. ACS Catal, 2015, 5: 4345–4352
Atanda L, Silahua A, Mukundan S, Shrotri A, Torres-Torres G, Beltramini J. RSC Adv, 2015, 5: 80346–80352
Nakajima K, Baba Y, Noma R, Kitano M, Kondo NJ, Hayashi S, Hara M. J Am Chem Soc, 2011, 133: 4224–4227
Yang F, Liu Q, Bai X, Du Y. Bioresource Tech, 2011, 102: 3424–3429
Zhang Y, Wang J, Ren J, Liu X, Li X, Xia Y, Lu G, Wang Y. Catal Sci Technol, 2012, 2: 2485–2491
Zhang Y, Wang J, Li X, Liu X, Xia Y, Hu B, Lu G, Wang Y. Fuel, 2015, 139: 301–307
Kreissl HT, Nakagawa K, Peng YK, Koito Y, Zheng J, Tsang SCE. J Catal, 2016, 338: 329–339
Jiao H, Zhao X, Lv C, Wang Y, Yang D, Li Z, Yao X. Sci Rep, 2016, 6: 34068
Fan W, Zhang Q, Deng W, Wang Y. Chem Mater, 2013, 25: 3277–3287
Yue C, Li G, Pidko EA, Wiesfeld JJ, Rigutto M, Hensen EJM. ChemSusChem, 2016, 9: 2421–2429
Yang F, Liu Q, Yue M, Bai X, Du Y. Chem Commun, 2011, 47: 4469–4471
Jiménez-Morales I, Teckchandani-Ortiz A, Santamaría-González J, Maireles-Torres P, Jiménez-López A. Appl Catal B-Environ, 2014, 144: 22–28
Zhang Y, Degirmenci V, Li C, Hensen EJM. ChemSusChem, 2011, 4: 59–64
Fan C, Guan H, Zhang H, Wang J, Wang S, Wang X. Biomass Bioenergy, 2011, 35: 2659–2665
Su Y, Chang G, Zhang Z, Xing H, Su B, Yang Q, Ren Q, Yang Y, Bao Z. AIChE J, 2016, 62: 4403–4417
Zhang Z, Du B, Zhang LJ, Da YX, Quan ZJ, Yang LJ, Wang XC. RSC Adv, 2013, 3: 9201–9205
Cao X, Teong SP, Wu D, Yi G, Su H, Zhang Y. Green Chem, 2015, 17: 2348–2352
Ståhlberg T, Rodriguez-Rodriguez S, Fristrup P, Riisager A. Chem Eur J, 2011, 17: 1456–1464
Wang HY, Liu SY, Zhao YL, Zhang HC, Wang JJ. ACS Sustain Chem Eng, 2016, doi: 10.1021/acssuschemeng.1026b01652
Zhou J, Huang T, Zhao Y, Xia Z, Xu Z, Jia S, Wang J, Zhang ZC. Ind Eng Chem Res, 2015, 54: 7977–7983
Liu W, Richard Zheng F, Li J, Cooper A. AIChE J, 2014, 60: 300–314
Su Y, Brown HM, Huang X, Zhou X, Amonette JE, Zhang ZC. Appl Catal A-Gen, 2009, 361: 117–122
Shuai L, Luterbacher J. ChemSusChem, 2016, 9: 133–155
Simeonov SP, Coelho JAS, Afonso CAM. ChemSusChem, 2012, 5: 1388–1391
Alonso DM, Wettstein SG, Dumesic JA. Green Chem, 2013, 15: 584–595
Azadi P, Carrasquillo-Flores R, Pagán-Torres YJ, Gürbüz EI, Farnood R, Dumesic JA. Green Chem, 2012, 14: 1573–1576
Alonso DM, Wettstein SG, Bond JQ, Root TW, Dumesic JA. ChemSusChem, 2011, 4: 1078–1081
Román-Leshkov Y, Chheda JN, Dumesic JA. Science, 2006, 312: 1933–1937
Wrigstedt P, Keskiväli J, Repo T. RSC Adv, 2016, 6: 18973–18979
Mohammad S, Held C, Altuntepe E, Köse T, Sadowski G. J Phys Chem B, 2016, 120: 3797–3808
Mohammad S, Held C, Altuntepe E, Köse T, Gerlach T, Smirnova I, Sadowski G. Fluid Phase Equilibr, 2016, 416: 83–93
Wrigstedt P, Keskiväli J, Leskelä M, Repo T. ChemCatChem, 2015, 7: 501–507
Teong SP, Yi G, Zeng H, Zhang Y. Green Chem, 2015, 17: 3751–3755
Acknowledgments
This work was supported by the National Natural Science Foundation of China (91545103, 21273071, 21403065), and the Commission of Science and Technology of Shanghai Municipality (10dz2220500).
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Wang, J., Xi, J., Xia, Q. et al. Recent advances in heterogeneous catalytic conversion of glucose to 5-hydroxymethylfurfural via green routes. Sci. China Chem. 60, 870–886 (2017). https://doi.org/10.1007/s11426-016-9035-1
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DOI: https://doi.org/10.1007/s11426-016-9035-1