Journal of Industrial and Engineering Chemistry, Vol.102, 186-194, October, 2021
Hydrogenation of 5-hydroxymethylfurfural into 2,5-bis (hydroxymethyl)furan over mesoporous Cu.Al2O3 catalyst: From batch to continuous processing
E-mail:
Biomass-derived monomers have received growing attention from sustainable polymer industry.
Particularly, diol compounds can be formed from furfural (FAL) and 5-hydroxymethylfurfural(HMF). Herein, the mesoporous Cu-Al2O3 catalyst (meso-CuA) prepared by solvent-deficient precipitation was evaluated to be efficient in selective hydrogenation of FAL and HMF to furfuryl alcohol to 2,5-bis (hydroxymethyl)furan (BHMF), respectively, at temperatures of lower than 100 °C and high H2 pressures. Owing to unique pore structure and small-sized copper nanoparticles entangled with alumina, meso-CuA turned out to be superior to other supported Cu catalysts in the hydrogenation of HMF to BHMF. Moreover, meso-CuA showed highly durable performance at the BHMF yield of higher than 90% at 100 °C, 50 bar H2, and weight hourly space velocity of 0.2 h-1 over time-on-stream of 100 h. The stability was also confirmed with the HMF feed containing 1 wt% of water that proved to have more considerable effect than other possible impurities. Centering around a catalytic reactor packed with meso-CuA, a process scheme from HMF feed to pure BHMF solid was developed at a production scale of 100 kg per day. The present results can contribute to designing commercial process of BHMF production from HMF and further, real biomass.
Keywords:5-hydroxymethylfurfural;Hydrogenation;Copper;Solvent-deficient precipitation;Continuous process
- Li G, Li N, Zheng M, Li S, Wang A, Cong Y, Wang X, Zhang T, Green Chem., 18, 3607 (2016)
- Kieber RJ, Silver SA, Kennemur JG, Polym. Chem., 8, 4822 (2017)
- Jiang Y, Woortman AJ, van Ekenstein GRA, Petrovic DM, Loos K, Mcromoleules, 15, 2482 (2014)
- Vijjamarri S, Streed S, Serum EM, Sibi MP, Du G, ACS Sustainable Chem. Eng., 6, 2491 (2018)
- Zeng C, Seino H, Ren J, Hatanaka K, Yoshie N, Marcromoleules, 46, 1794 (2013)
- Hu F, La Scala JJ, Sadler JM, Palmese GR, Marcromoleules, 47, 3332 (2014)
- Gopalakrishnan P, Narayan-Sarathy S, Ghosh T, Mahajan K, Belgacem MN, J. Polym. Res., 21, 340 (2014)
- Mittal A, Pilath HM, Johnson DK, Energy Fuels, 34(3), 3284 (2020)
- Shen G, Andrioletti B, Queneau Y, Curr. Opin. Green Sustain. Chem., 26 (2020)
- Perez GP, Mukherjee A, Dumont MJ, J. Ind. Eng. Chem., 70, 1 (2019)
- Mishra DK, Cho JK, Kim YJ, J. Ind. Eng. Chem., 60, 513 (2018)
- Gupta SSR, Vinu A, Kantam ML, ChemPlusChem, 86, 259 (2021)
- Zou L, Zheng Z, Tan H, Xu Q, Ouyang J, RSC Adv., 10, 21781 (2020)
- Liu LJ, Wang ZM, Lyu YJ, Zhang JF, Huang Z, Qi T, Si ZB, Yang HQ, Hu CW, Catal, Sci. Technol., 10, 278 (2020)
- Elsayed I, Jackson MA, Hassan EB, ACS sustainable Chem. Eng., 8, 1774 (2020)
- Arias KS, Carceller JM, Climent MJ, Corma A, Lborra S, ChemSusChem, 13, 1864 (2020)
- de Jong E, et al., Biobased Monomers, Polymers, and Materials, American Chemical Society, Washington, DC, pp.1 2012.
- Yang ZY, Wen M, Zong MH, Li N, Catal. Commun., 139, 105979 (2020)
- Hu L, Xu J, Zhou S, He A, Tang X, Lin L, Xu J, Zhao Y, ACS Catal., 8, 2959 (2018)
- Zhang J, Wang T, Tang X, Peng L, Wei J, Lin L, BioResources, 13(3), 7137 (2018)
- Millan A, Sals N, Torres M, Canela-Garayoa R, Catalysts, 11, 216 (2021)
- Xia ZH, Zong MH, Li N, Enzyme Microb. Technol., 134 (2020)
- Mishra DK, Lee HJ, Truong CC, Kim J, Suh YW, Baek J, Kim YJ, Mol. Catal., 484 (2019)
- Yao S, Wang X, Jiang Y, Wu F, Chen X, Mu X, ACS Sustainable Chem. Eng., 2, 173 (2014)
- Chatterjee M, Ishizaka T, Kawanami H, Green. Chem., 16, 4734 (2014)
- Kumalaputri AJ, Bottari G, Erne PM, Heeres HJ, Barta K, ChemSusChem, 7, 2266 (2014)
- Zhu Y, Kong X, Zheng H, Ding G, Zhu Y, Li YW, Catal. Sci. Technol., 5, 4208 (2015)
- Bottari G, Kumpalaputri AJ, Krawczyk KK, Feringa BL, Heeres HJ, Barta K, ChemSusChem, 8, 1323 (2015)
- Upare PP, Hwang YK, Hwang DW, Green Chem., 20, 879 (2018)
- Liu Y, Mellmer MA, Alonso DM, Dumesic JA, ChemSusChem, 8, 3983 (2015)
- Lima S, Chadwick D, Hellgardt K, RSC Adv., 7, 31401 (2017)
- Yu L, He L, Chen J, Zheng J, Ye L, Lin H, Yuan Y, ChemCatChem, 7, 1701 (2015)
- O’Driscoll A, Curtin T, Hernandez WY, Voort PVD, Leahy JJ, Org. Process. Res. Dev., 20, 1917 (2016)
- Chen X, Zhang L, Zhnag B, Guo X, Mu X, Sci. Rep., 6, 28558 (2016)
- Park S, Kannapu HPR, Jeong C, Kim J, Suh YW, ChemCatChem, 12, 105 (2020)
- Kijenski J, Winiarek P, Paryjczak T, Lewicki A, Mikolajska A, Appl. Catal. A: Gen., 233(1-2), 171 (2002)
- Toledo F, Ghampson IT, Sepulved C, Garcia R, Fierro JLG, Videla A, Serpell R, Escalona N, Fuel, 242, 532 (2019)
- Oh J, Bathula HB, Park JH, Suh YW, Commun. Chem., 2, 68 (2019)
- Bathula HB, Oh J, Jo Y, Suh YW, Catalysts, 9, 719 (2019)
- Rao KTV, Hu Y, Yuan Z, Zhang Y, Xu CC, Appl. Catal. A: Gen., 609 (2021)
- Cho K, Lee SM, Kim HJ, Ko YJ, Son SU, Chem. Commun., 55, 3697 (2019)
- Chen GY, Wu LB, Fan H, Li BG, Ind. Eng. Chem. Res., 57(48), 16172 (2018)
- Overton JC, Engelberth AS, Mosier NS, ACS Sustainable Chem. Eng., 8, 18 (2020)