Highly selective hydrogenation of furfural to tetrahydrofurfuryl alcohol over MIL-101(Cr)-NH2 supported Pd catalyst at low temperature

doi:10.1016/S1872-2067(18)63009-8

Abstract

Abstract:

An efficient heterogeneous catalyst, Pd@MIL-101(Cr)-NH₂, is prepared through a direct pathway of anionic exchange followed by hydrogen reduction with amino-containing MIL-101 as the host matrix. The composite is thermally stable up to 350℃ and the Pd nanoparticles uniformly disperse on the matal organic framework (MOF) support, which are attributed to the presence of the amino groups in the frameworks of MIL-101(Cr)-NH₂. The selective hydrogenation of biomass-based furfural to tetrahydrofurfuryl alcohol is investigated by using this multifunctional catalyst Pd@MIL-101(Cr)-NH₂ in water media. A complete hydrogenation of furfural is achieved at a low temperature of 40℃ with the selectivity of tetrahydrofurfuryl alcohol close to 100%. The amine-functionalized MOF improves the hydrogen bonding interactions between the intermediate furfuryl alcohol and the support, which is conducive for the further hydrogenation of furfuryl alcohol to tetrahydrofurfuryl alcohol in good coor-dination with the metal sites.

Key words: Metal-organic frameworks, Amino functionalization, Pd nanoparticle, Biomass, Selective hydrogenation

Dongdong Yin, Hangxing Ren, Chuang Li, Jinxuan Liu, Changhai Liang. Highly selective hydrogenation of furfural to tetrahydrofurfuryl alcohol over MIL-101(Cr)-NH₂ supported Pd catalyst at low temperature[J]. Chinese Journal of Catalysis, 2018, 39(2): 319-326.

×
share this article

Add to citation manager EndNote|Ris|BibTeX

URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(18)63009-8

https://www.cjcatal.com/EN/Y2018/V39/I2/319

References

[1] P. Gallezot, Chem. Soc. Rev., 2012, 41, 1538-1558.
[2] D. M. Alonso, J. Q. Bond, J. A. Dumesic, Green Chem., 2010, 12, 1493-1513.
[3] X. D. Li, P. Jia, T. F. Wang, ACS Catal., 2016, 6, 7621-7640.
[4] R. Mariscal, P. Maireles-Torres, M. Ojeda, I. Sádaba, M. López Granados, Energy Environ. Sci., 2016, 9, 1144-1189.
[5] Werpy T, Petersen G, Aden A, Bozell J, Holladay J, White J, Man-heim A, Eliot D, Lasure L, Jones S (2004) No. DOE/GO-102004-1992. Department of Energy Washington DC.
[6] K. Yan, Y. Q. Liu, Y. R. Lu, J. J. Chai, L. P. Sun, Catal. Sci. Technol., 2017, 7, 1622-1645.
[7] K. Fulajtárova, T. Soták, M. Hronec, I. Vávra, E. Dobrocka, M. Omastová, Appl. Catal. A, 2015, 502, 78-85.
[8] M. J. Taylor, L. J. Durndell, M. A. Isaacs, C. M. A. Parlett, K. Wilson, A. F. Lee, G. Kyriakou, Appl. Catal. B, 2016, 180, 580-585.
[9] N. S. Biradar, A. M. Hengne, S. N. Birajdar, P. S. Niphadkar, P. N. Joshi, C. V. Rode, ACS Sustainable Chem. Eng., 2014, 2, 272-281.
[10] J. Wu, G. Gao, J. L. Li, P. Sun, X. D. Long and F. W. Li, Appl. Catal. B, 2017, 203, 227-236.
[11] S. B. Liu, Y. Amada, M. Tamura, Y. Nakagawa, K. Tomishige, Catal. Sci. Technol., 2014, 4, 2535-2549.
[12] Y. L. Yang, Z. T. Du, Y. Z. Huang, F. Lu, F. Wang, J. Gao, J. Xu, Green Chem., 2013, 15, 1932-1940.
[13] M. H. Zhou, Z. Zeng, H. Y. Zhu, G. M. Xiao, R. Xiao, Energy Chem., 2014, 23, 91-96.
[14] M. Hronec, K. Fulajtarová, Catal. Commun., 2012, 24, 100-104.
[15] C. Stamigna, D. Chiaretti, E. Chiaretti, P. P. Prosini, Biomass Bioenergy, 2012, 39, 478-483.
[16] G. W. Huber, S. Iborra, A. Corma, Chem. Rev., 2006, 106, 4044-4098.
[17] F. A. Khan, A. Vallat, G. Süss-Fink, Catal. Commun., 2011, 12, 1428-1431.
[18] Y. Nakagawa, H. Nakazawa, H. Watanabe, K. Tomishige, Chem-CatChem, 2012, 4, 1791-1797.
[19] Y. Nakagawa, K. Tomishige, Catal. Commun., 2010, 12, 154-156.
[20] Y. Nakagawa, K. Takada, M. Tamura, K. Tomishige, ACS Catal., 2014, 4, 2718-2726.
[21] J. R. Long, O. M. Yaghi, Chem. Soc. Rev., 2009, 38, 1213-1214.
[22] A. H. Chughtai, N. Ahmad, H. A. Younus, A. Laypkov, F. Verpoort, Chem. Soc. Rev., 2015, 44, 6804-6849.
[23] F. A. Almeida Paz, J. Klinowski, S. M. F. Vilela, J. P. C. Tome, J. A. S. Cavaleiro, J. Rocha, Chem. Soc. Rev., 2012, 41, 1088-1110.
[24] P. Silva, S. M. F. Vilela, J. P. C. Tome, F. A. Almeida Paz, Chem. Soc. Rev., 2015, 44, 6774-6803.
[25] B. Murillo, B. Zornoza, O. de la Iglesia, C. Téllez, J. Coronas, J. Catal., 2016, 334, 60-67.
[26] Z. H. Wang, Q. W. Chen, Green Chem., 2016, 18, 5884-5889.
[27] Q. Q. Yuan, D. M. Zhang, L. v. Haandel, F. Y. Ye, T. Xue, E. J. M. Hen-sen, Y. J. Guan, J. Mol. Catal. A, 2015, 406, 58-64.
[28] F. M. Zhang, S. Zheng, Q. Xiao, Y. J. Zhong, W. D.Zhu, A. Lin, M. Samy El-Shall, Green Chem., 2016, 18, 2900-2908.
[29] G. Ferey, C. Mellot-Draznieks, C. Serre, F. Millange, J. Dutour, S. Surble, I. Margiolaki, Science, 2005, 309, 2040-2042.
[30] D.Y. Hong, Y. K. Hwang, C. Serre, G. Férey, J. S. Chang, Adv. Funct. Mater., 2009, 19, 1537-1552.
[31] F. M. Zhang, Y. Jin, Y. H. Fu, Y. J. Zhong, W. D. Zhu, A. A. Ibrahim, M. S. El-Shall, J. Mater. Chem. A, 2015, 3, 17008-17015.
[32] G. Akiyama, R. Matsuda, H. Sato, M. Takata, S. Kitagawa, Adv. Mater., 2011, 23, 3294-3297.
[33] A. Herbst, C. Janiak, New J. Chem., 2016, 40, 7958-7967.
[34] A. Aijaz, Q. L. Zhu, N. Tsumori, T. Akita, Q. Xu, Chem. Commun., 2015, 51, 2577-2580.
[35] R. Q. Fang, H. L. Liu, R. Luque, Y. W. Li, Green Chem., 2015, 17, 4183-4188.
[36] J. Z. Chen, R. L. Liu, Y. Y. Guo, L. M. Chen, H. Gao, ACS Catal., 2015, 5, 722-733.
[37] J. Z. Chen, W. Zhang, L. M. Chen, L. L. Ma, H. Gao, T. J. Wang, ChemPlusChem, 2013, 78, 142-148.
[38] Y. C. Lin, C. L. Kong, L. Chen, RSC Adv., 2012, 2, 6417-6419.
[39] A. Buragohain, P. Van Der Voort, S. Biswas, Microporous Mesoporous Mater., 2015, 215, 91-97.
[40] H. X. Ren, C. Li, D. D. Yin, J. X. Liu, C. H. Liang, RSC Adv., 2016, 6, 85659-85665.
[41] Y. Y. Pan, B. Z. Yuan, Y. W. Li, D. H. He, Chem. Commun., 2010, 46, 2280-2282.
[42] M. Saikia, L. Saikia, RSC Adv., 2016, 6, 14937-14947.
[43] D. M. Jiang, L. L. Keenan, A. D. Burrows, K. J. Edler, Chem. Commun., 2012, 48, 12053-12055.
[44] Z. Y. Guo, C. X. Xiao, R. V. Maligal-Ganesh, L. Zhou, T. W. Goh, X. L. Li, D. Tesfagaber, A. Thiel, W. Y. Huang, ACS Catal., 2014, 4, 1340-1348.
[45] J. Z. Chen, R. L.Liu, Y. Y. Guo, L. M. Chen, H. Gao, ACS Catal., 2014, 5, 722-733.
[46] M. Kandiah, M. H. Nilsen, S. Usseglio, S. Jakobsen, U. Olsbye, M. Tilset, C. Larabi, E. A. Quadrelli, F. Bonino, K. P. Lillerud, Chem. Mater., 2010, 22, 6632-6640.
[47] S. H. Pang, C. A. Schoenbaum, D. K. Schwartz, J. W. Medlin, ACS Catal., 2014, 4, 3123-3131.
[48] M. Hronec, K. Fulajtárova, M. Micušik, Appl. Catal. A, 2013, 468, 426-431.
[49] K. Yan, A. C. Chen, Fuel, 2014, 115, 101-108.
[50] S. Yoshimaru, M. Sadakiyo, A. Staykov, K. Kato, M. Yamauchi, Chem. Commun., 2017, 53, 6720-6723.
[51] Q. Q. Yuan, D. M. Zhang, L. V. Haandel, F. Y. Ye, T. Xue, E. J. M. Hen-sen, Y. J. Guan, J. Mol. Catal. A, 2015, 406, 58-64.

Highly selective hydrogenation of furfural to tetrahydrofurfuryl alcohol over MIL-101(Cr)-NH₂ supported Pd catalyst at low temperature

PDF (PC)

Knowledge

Supporting Information

Abstract

Cite this article

share this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

[1]	Shiyao Liu, Yutong Gong, Xiao Yang, Nannan Zhang, Huibin Liu, Changhai Liang, Xiao Chen. Acid-durable intermetallic CaNi₂Si₂ catalyst with electron-rich Ni sites for aqueous phase hydrogenation of unsaturated organic anhydrides/acids [J]. Chinese Journal of Catalysis, 2023, 50(7): 260-272.
[2]	Enara Fernandez, Laura Santamaria, Irati García, Maider Amutio, Maite Artetxe, Gartzen Lopez, Javier Bilbao, Martin Olazar. Elucidating coke formation and evolution in the catalytic steam reforming of biomass pyrolysis volatiles at different fixed bed locations [J]. Chinese Journal of Catalysis, 2023, 48(5): 101-116.
[3]	Fengwei Zhang, Hefang Guo, Mengmeng Liu, Yang Zhao, Feng Hong, Jingjing Li, Zhengping Dong, Botao Qiao. Enhancing the chemoselective hydrogenation of nitroarenes: Designing a novel surface-strained carbon-based Pt nanocatalyst [J]. Chinese Journal of Catalysis, 2023, 48(5): 195-204.
[4]	Duozheng Ma, Xiangcheng Li, Chuang Liu, Caroline Versluis, Yingchun Ye, Zhendong Wang, Eelco T. C. Vogt, Bert M. Weckhuysen, Weimin Yang. SCM-36 zeolite nanosheets applied in the production of renewable p-xylene from ethylene and 2,5-dimethylfuran [J]. Chinese Journal of Catalysis, 2023, 47(4): 200-213.
[5]	Hongfang Wang, Leitao Xu, Jingcheng Wu, Peng Zhou, Shasha Tao, Yuxuan Lu, Xianwen Wu, Shuangyin Wang, Yuqin Zou. Boosting 5-hydroxymethylfurfural electrooxidation in neutral electrolytes via TEMPO-enhanced dehydrogenation and OH adsorption [J]. Chinese Journal of Catalysis, 2023, 46(3): 148-156.
[6]	Chao Nie, Xiangdong Long, Qi Liu, Jia Wang, Fei Zhan, Zelun Zhao, Jiong Li, Yongjie Xi, Fuwei Li. Facile fabrication of atomically dispersed Ru-P-Ru ensembles for efficient hydrogenations beyond isolated single atoms [J]. Chinese Journal of Catalysis, 2023, 45(2): 107-119.
[7]	Yujie Li, Yuanyuan Liu, Zeyan Wang, Peng Wang, Zhaoke Zheng, Hefeng Cheng, Ying Dai, Baibiao Huang. Enhanced photocatalytic H2O2 production over Pt(II) deposited boron containing metal-organic framework via suppressing the simultaneous decomposition [J]. Chinese Journal of Catalysis, 2023, 45(2): 132-140.
[8]	Yuxuan Lu, Liu Yang, Yimin Jiang, Zhenran Yuan, Shuangyin Wang, Yuqin Zou. Engineering a localized electrostatic environment to enhance hydroxyl activating for electrocatalytic biomass conversion [J]. Chinese Journal of Catalysis, 2023, 53(10): 153-160.
[9]	Wenjuan Zhang, Pei Jing, Juan Du, Shujie Wu, Wenfu Yan, Gang Liu. Interfacial-interaction-induced fabrication of biomass-derived porous carbon with enhanced intrinsic active sites [J]. Chinese Journal of Catalysis, 2022, 43(8): 2231-2239.
[10]	Jiang Zhang, Zijian Wang, Mugeng Chen, Yifeng Zhu, Yongmei Liu, Heyong He, Yong Cao, Xinhe Bao. N-doped carbon layer-coated Au nanocatalyst for H₂-free conversion of 5-hydroxymethylfurfural to 5-methylfurfural [J]. Chinese Journal of Catalysis, 2022, 43(8): 2212-2222.
[11]	Fenglei Lyu, Wei Hua, Huirong Wu, Hao Sun, Zhao Deng, Yang Peng. Structural and interfacial engineering of well-defined metal-organic ensembles for electrocatalytic carbon dioxide reduction [J]. Chinese Journal of Catalysis, 2022, 43(6): 1417-1432.
[12]	Boyu Zhang, Jiafu Shi, Yang Zhao, Han Wang, Ziyi Chu, Yu Chen, Zhenhua Wu, Zhongyi Jiang. Pickering interfacial biocatalysis with enhanced diffusion processes for CO₂ mineralization [J]. Chinese Journal of Catalysis, 2022, 43(4): 1184-1191.
[13]	Mengru Wang, Yi Wang, Xiaoling Mou, Ronghe Lin, Yunjie Ding. Design strategies and structure-performance relationships of heterogeneous catalysts for selective hydrogenation of 1,3-butadiene [J]. Chinese Journal of Catalysis, 2022, 43(4): 1017-1041.
[14]	Junmin Huang, Jianmin Chen, Wangxi Liu, Jingwen Zhang, Junying Chen, Yingwei Li. Copper-doped zinc sulfide nanoframes with three-dimensional photocatalytic surfaces for enhanced solar driven H₂ production [J]. Chinese Journal of Catalysis, 2022, 43(3): 782-792.
[15]	Ling-Ling Zheng, Long-Shuai Zhang, Ying Chen, Lei Tian, Xun-Heng Jiang, Li-Sha Chen, Qiu-Ju Xing, Xiao-Zhen Liu, Dai-She Wu, Jian-Ping Zou. A new strategy for the fabrication of covalent organic framework-metal-organic framework hybrids via in-situ functionalization of ligands for improved hydrogen evolution reaction activity [J]. Chinese Journal of Catalysis, 2022, 43(3): 811-819.