One-pot cascade conversion of xylose to furfuryl alcohol over a bifunctional Cu/SBA-15-SO3H catalyst

doi:10.1016/S1872-2067(19)63505-9

Abstract

Abstract: The conversion of hemicellulose-derived xylose to furfuryl alcohol is a practical procedure for producing value-added chemicals from biomass. In this study, a bifunctional Cu/SBA-15-SO₃H catalyst was employed for the one-pot catalytic conversion of xylose to furfuryl alcohol with a yield of up to 62.6% at the optimized conditions of 140℃, 4 MPa, and for 6 h in a biphasic water/n-butanol solvent. A high reaction temperature resulted in further hydrogenation to 2-methyl furan, while a high hydrogen pressure led to a side hydrogenation reaction to xylitol. The biphasic solvent allowed xylose solvation as well as furfuryl product extraction. The acidic -SO₃H sites and Cu sites co-existed, maintained a balance, and cooperatively catalyzed the cascade conversion. Excessive acidic sites and large pores could promote the xylose conversion, although a low furfuryl alcohol yield was obtained. This catalytic system could be potentially applied to the one-pot synthesis of furfuryl alcohol from hemicellulose-derived xylose.

Key words: Biomass, Furfuryl alcohol, Heterogeneous catalysis, One-pot synthesis, Xylose

CLC Number:

Tianyu Deng, Guangyue Xu, Yao Fu. One-pot cascade conversion of xylose to furfuryl alcohol over a bifunctional Cu/SBA-15-SO₃H catalyst[J]. Chinese Journal of Catalysis, 2020, 41(3): 404-414.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(19)63505-9

https://www.cjcatal.com/EN/Y2020/V41/I3/404

References

[1] H. Li, Z. Fang, R. L. Smith, S. Yang, Prog. Energy Combust. Sci., 2016, 55, 98-194.
[2] D. M. Alonso, S. G. Wettstein, J. A. Dumesic, Chem. Soc. Rev., 2012, 41, 8075-8098.
[3] J. Byun, J. Han, Green Chem., 2017, 19, 5214-5229.
[4] A. Corma, S. Iborra, A. Velty, Chem. Rev., 2007, 107, 2411-2502.
[5] D. M. Alonso, S. G. Wettstein, J. A. Dumesic, Green Chem., 2013, 15, 584-595.
[6] J. N. Chheda, G. W. Huber, J. A. Dumesic, Angew. Chem. Int. Ed., 2007, 46, 7164-7183.
[7] J. E. Romo, N. V. Bollar, C. J. Zimmermann, S. G. Wettstein, Chem-CatChem, 2018, 10, 4805-4816.
[8] S. Dutta, S. De, B. Saha, M. I. Alam, Catal. Sci. Technol., 2012, 2, 2025-2036.
[9] K. Yan, G. Wu, T. Lafleur, C. Jarvis, Renew. Sustain. Energy Rev., 2014, 38, 663-676.
[10] S. Chen, R. Wojcieszak, F. Dumeignil, E. Marceau, S. Royer, Chem. Rev., 2018, 118, 11023-11117.
[11] C. Sener, A. H. Motagamwala, D. M. Alonso, J. A. Dumesic, ChemSusChem, 2018, 11, 2321-2331.
[12] W. Gong, C. Chen, Y. Zhang, H. Zhou, H. Wang, H. Zhang, Y. Zhang, G. Wang, H. Zhao, ACS Sustain. Chem. Eng., 2017, 5, 2172-2180.
[13] X. Zhang, K. Wilson, A. F. Lee, Chem. Rev., 2016, 116, 12328-12368.
[14] P. Bhaumik, P. L. Dhepe, Catal. Rev.-Sci. Eng., 2016, 58, 36-112.
[15] I. Agirrezabal-Telleria, J. Requies, M. B. Güemez, P. L. Arias, Appl. Catal. B Environ., 2014, 145, 34-42.
[16] C. P. Jiménez-Gómez, J. A. Cecilia, D. Durán-Martín, R. Moreno-Tost, J. Santamaría-González, J. Mérida-Robles, R. Mariscal, P. Maireles-Torres, J. Catal., 2016, 336, 107-115.
[17] P. N. Paulino, R. F. Perez, N. G. Figueiredo, M. A. Fraga, Green Chem., 2017, 19, 3759-3763.
[18] J. Cui, J. Tan, X. Cui, Y. Zhu, T. Deng, G. Ding, Y. Li, ChemSusChem, 2016, 9, 1259-1262.
[19] R. F. Perez, M. A. Fraga, Green Chem., 2014, 16, 3942-3950.
[20] Y. He, Y. Ding, C. Ma, J. Di, C. Jiang, A. Li, Green Chem., 2017, 19, 3844-3850.
[21] Y. Nakagawa, M. Tamura, K. Tomishige, ACS Catal., 2013, 3, 2655-2668.
[22] R. Weingarten, G. A. Tompsett, W. C. Conner Jr., G. W. Huber, J. Catal., 2011, 279, 174-182.
[23] S. J. Canhaci, R. F. Perez, L. E. P. Borges, M. A. Fraga, Appl. Catal. B Environ., 2017, 207, 279-285.
[24] R. F. Perez, S. J. Canhaci, L. E. P. Borges, M. A. Fraga, Catal. Today, 2017, 289, 273-279.
[25] R. F. Perez, O. S. G. P. Soares, A. M. D. de Farias, M. F. R. Pereira, M. A. Fraga, Appl. Catal. B Environ., 2018, 232, 101-107.
[26] J. Guo, G. Xu, Z. Han, Y. Zhang, Y. Fu, Q. Guo, ACS Sustainable Chem. Eng., 2014, 2, 2259-2266.
[27] T. Deng, L. Yan, X. Li, Y. Fu, ChemSusChem, 2019, 12, 3837-3848.
[28] D. M. Lai, L. Deng, J. Li, B. Liao, Q. X. Guo, Y. Fu, ChemSusChem, 2011, 4, 55-58.
[29] D. Zhao, J. Feng, Q. Huo, N. Melosh, G. H. Fredrickson, B. F. Chmelka, G. D. Stucky, Science, 1998, 279, 548-552.
[30] N. V. Krishna, S. Anuradha, R. Ganesh, V. V. Kumar, P. Selvam, ChemCatChem, 2018, 10, 5610-5618.
[31] D. Margolese, J. A. Melero, S. C. Christiansen, B. F. Chmelka, G. D. Stucky, Chem. Mater., 2000, 12, 2448-2459.
[32] M. Kondeboina, S. S. Enumula, V. R. B. Gurram, R. R. Chada, D. R. Burri, S. R. R. Kamaraju, J. Ind. Eng. Chem., 2018, 61, 227-235.
[33] H. Tian, X. L. Zhang, J. Scott, C. Ng, R. Amal, J. Mater. Chem. A, 2014, 2, 6432-6438.
[34] S. Ganesh Babu, R. Vinoth, P. Surya Narayana, D. Bahnemann, B. Neppolian, APL Mater., 2015, 3, 104415/1-104415/8.
[35] A. E. R. S. Khder, S. A. Ahmed, K. S. Khairou, H. M. Altass, J. Porous Mater., 2017, 25, 1-13.
[36] L. Hu, Y. Huang, F. Zhang, Q. Chen, Nanoscale, 2013, 5, 4186-4190.
[37] G. Li, H. Cheng, X. Xiong, X. Lu, C. Xu, C. Lu, X. Zou, Q. Xu, Sci. Rep., 2017, 7, 3212.
[38] E. M. Usai, M. F. Sini, D. Meloni, V. Solinas, A. Salis, Microporous Mesoporous Mater., 2013, 179, 54-62.
[39] B. O. Dalla Costa, M. S. Legnoverde, C. Lago, H. P. Decolatti, C. A. Querini, Microporous Mesoporous Mater., 2016, 230, 66-75.
[40] R. Estevez, M. I. López, C. Jiménez-Sanchidrián, D. Luna, F. J. Romero-Salguero, F. M. Bautista, Appl. Catal. A Gen., 2016, 526, 155-163.
[41] V. Choudhary, S. I. Sandler, D. G. Vlachos, ACS Catal., 2012, 2, 2022-2028.
[42] I. Agirrezabal-Telleria, J. Requies, M. B. Güemez, P. L. Arias, Appl. Catal. B Environ., 2012, 115-116, 169-178.
[43] X. Hu, R. J. M. Westerhof, D. Dong, L. Wu, C.-Z. Li, ACS Sustain. Chem. Eng., 2014, 2, 2562-2575.

One-pot cascade conversion of xylose to furfuryl alcohol over a bifunctional Cu/SBA-15-SO₃H catalyst

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