Selective hydrogenolysis of furfuryl alcohol to 1,5-and 1,2-pentanediol over Cu-LaCoO3 catalysts with balanced Cu0-CoO sites

doi:10.1016/S1872-2067(18)63110-9

Abstract

Abstract:

Selective hydrogenolysis of biomass-derived furfuryl alcohol (FFA) to 1,5-and 1,2-pentanediol (PeD) was conducted over Cu-LaCoO₃ catalysts with different Cu loadings; the catalysts were derived from perovskite structures prepared by a one-step citrate complexing method. The catalytic performances of the Cu-LaCoO₃ catalysts were found to depend on the Cu loading and pretreatment conditions. The catalyst with 10 wt% Cu loading exhibited the best catalytic performance after prereduction in 5% H₂-95% N₂, achieving a high FFA conversion of 100% and selectivity of 55.5% for 1,5-pentanediol (40.3%) and 1,2-pentanediol (15.2%) at 413 K and 6 MPa H₂. This catalyst could be reused four times without a loss of FFA conversion but it resulted in a slight decrease in pentanediol selectivity. Correlation between the structural changes in the catalysts at different states and the simultaneous variation in the catalytic performance revealed that cooperative catalysis between Cu⁰ and CoO promoted the hydrogenolysis of FFA to PeDs, especially to 1,5-PeD, while Co⁰ promoted the hydrogenation of FFA to tetrahydrofurfuryl alcohol (THFA). Therefore, it is suggested that a synergetic effect between balanced Cu⁰ and CoO sites plays a critical role in achieving a high yield of PeDs with a high 1,5-/1,2-pentanediol selectivity ratio during FFA hydrogenolysis.

Key words: Furfuryl alcohol, Selective hydrogenolysis, Pentanediol, Cu-LaCoO₃ catalyst, Perovskite structure

Fangfang Gao, Hailong Liu, Xun Hu, Jing Chen, Zhiwei Huang, Chungu Xia. Selective hydrogenolysis of furfuryl alcohol to 1,5-and 1,2-pentanediol over Cu-LaCoO₃ catalysts with balanced Cu⁰-CoO sites[J]. Chinese Journal of Catalysis, 2018, 39(10): 1711-1723.

×
share this article

Add to citation manager EndNote|Ris|BibTeX

URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(18)63110-9

https://www.cjcatal.com/EN/Y2018/V39/I10/1711

References

[1] L. T. Mika, E. Csefalvay, A. Nemeth, Chem Rev., 2018, 118, 505-613.
[2] C. Z. Li, X. C. Zhao, A. Q. Wang, G. W. Huber, T. Zhang, Chem Rev., 2015, 115, 11559-11624.
[3] R. Mariscal, P. Maireles-Torres, M. Ojeda, I. Sádaba, M. López Granados, Energy Environ. Sci., 2016, 9, 1144-1189.
[4] M. Besson, P. Gallezot, C. Pinel, Chem Rev., 2014, 114, 1827-1870.
[5] M. J. Climent, A. Corma, S. Iborra, Green Chem., 2014, 16, 516-547.
[6] Y. Nakagawa, M. Tamura, K. Tomishige, ACS Catal., 2013, 3, 2655-2668.
[7] J. Y. He, K. F. Huang, K. J. Barnett, S. H. Krishna, D. M. Alonso, Z. J. Brentzel, S. P. Burt, T. Walker, W. F. Banholzer, C. T. Maravelias, I. Hermans, J. A. Dumesic, G. W. Huber, Faraday Discuss., 2017, 202, 247-267.
[8] H. L. Liu, Z. W. Huang, F. Zhao, F. Cui, X. M. Li, C. G. Xia, J. Chen, Catal. Sci. Technol., 2016, 6, 668-671.
[9] Z. J. Brentzel, K. J. Barnett, K. F. Huang, C. T. Maravelias, J. A. Dumesic, G. W. Huber, ChemSusChem, 2017, 10, 1351-1355.
[10] T. P. Sulmonetti, B. Hu, S. Lee, P. K. Agrawal, C. W. Jones, ACS Sustainable Chem. Eng., 2017, 5, 8959-8969.
[11] H. W. Wijaya, T. Kojima, T. Hara, N. Ichikuni, S. Shimazu, ChemCatChem, 2017, 9, 2869-2874.
[12] R. F. Ma, X. P. Wu, T. Tong, Z. J. Shao, Y. Q. Wang, X. H. Liu, Q. N. Xia, X. Q. Gong, ACS Catal., 2017, 7, 333-337.
[13] B. Zhang, Y. L. Zhu, G. Q. Ding, H. Y. Zheng, Y. W. Li, Green Chem., 2012, 14, 3402-3409.
[14] T. Mizugaki, T. Yamakawa, Y. Nagatsu, Z. Maeno, T. Mitsudome, K. Jitsukawa, K. Kaneda, ACS Sustainable Chem. Eng., 2014, 2, 2243-2247.
[15] W. J. Xu, H. F. Wang, X. H. Liu, J. W. Ren, Y. Q. Wang, G. Z. Lu, Chem. Commun., 2011, 47, 3924-3926.
[16] M. Chia, Y. J. Pagan-Torres, D. Hibbitts, Q. H. Tan, H. N. Pham, A. K. Datye, M. Neurock, R. J. Davis, J. A. Dumesic, J. Am. Chem. Soc., 2011, 133, 12675-12689.
[17] M. Chatterjee, H. Kawanami, T. Ishizaka, M. Sato, T. Suzuki, A. Suzuki, Catal. Sci. Technol., 2011, 1, 1466-1471.
[18] J. Guan, G. M. Peng, Q. Cao, X. D. Mu, J. Phys. Chem. C, 2014, 118, 25555-25566.
[19] S. Koso, N. Ueda, Y. Shinmi, K. Okumura, T. Kizuka, K. Tomishige, J. Catal., 2009, 267, 89-92.
[20] K. Y. Chen, S. Koso, T. Kubota, Y. Nakagawa, K. Tomishige, ChemCatChem, 2010, 2, 547-555.
[21] S. Koso, I. Furikado, A. Shimao, T. Miyazawa, K. Kunimori, K. Tomishige, Chem. Commun., 2009, 2035-2037.
[22] K. Y. Chen, K. Mori, H. Watanabe, Y. Nakagawa, K. Tomishige, J. Catal., 2012, 294, 171-183.
[23] S. B. Liu, Y. Amada, M. Tamura, Y. Nakagawa, K. Tomishige, Green Chem., 2014, 16, 617-626.
[24] S. B. Liu, Y. Amada, M. Tamura, Y. Nakagawa, K. Tomishige, Catal. Sci. Technol., 2014, 4, 2535-2549.
[25] Y. Nakagawa, M. Tamura, K. Tomishige, Catal. Surv. Asia, 2015, 19, 249-256.
[26] K. Tomishige, Y. Nakagawa, M. Tamura, Green Chem., 2017, 19, 2876-2924.
[27] H. L. Liu, Z. W. Huang, H. X. Kang, C. G. Xia, J. Chen, Chin. J. Catal., 2016, 37, 700-710.
[28] D. Götz, M. Lucas, P. Claus, Catalysts, 2017, 7, 50/1-50/7.
[29] H. Adkins, R. Connor, J. Am. Chem. Soc., 1931, 53, 1091-1095.
[30] J. Lee, S. P. Burt, C. A. Carrero, A. C. Alba-Rubio, I. Ro, B. J. O'Neill, H. J. Kim, D. H. K. Jackson, T. F. Kuech, I. Hermans, J. A. Dumesic, G. W. Huber, J. Catal., 2015, 330, 19-27.
[31] J. C. Lee, Y. Xu, G. W. Huber, Appl. Catal. B, 2013, 140-141, 98-107.
[32] M. Y. Chen, C. B. Chen, B. Zada, Y. Fu, Green Chem., 2016, 18, 3858-3866.
[33] B. H. Zhao, B. H. Yan, S. Y. Yao, Z. H. Xie, Q. Y. Wu, R. Ran, D. Weng, C. Zhang, J. G. Chen, J. Catal., 2018, 358, 168-178.
[34] X. L. Zhang, Y. D. Gong, S. Q. Li, C. W. Sun, ACS Catal., 2017, 7, 7737-7747.
[35] J. Hwang, R. R. Rao, L. Giordano, Y. Katayama, Y. Yu, Y. Shao-Horn, Science, 2017, 358, 751-756.
[36] F. Polo-Garzon, Z. L. Wu, J. Mater. Chem. A, 2018, 6, 2877-2894.
[37] S. Dama, S. R. Ghodke, R. Bobade, H. R. Gurav, S. Chilukuri, Appl. Catal. B, 2018, 224, 146-158.
[38] H. L. Liu, Z. W. Huang, Z. B. Han, K. L. Ding, H. C. Liu, C. G. Xia, J. Chen, Green Chem., 2015, 17, 4281-4290.
[39] H. L. Liu, Z. W. Huang, H. X. Kang, X. M. Li, C. G. Xia, J. Chen, H. C. Liu, Appl. Catal. B, 2018, 220, 251-263.
[40] F. Ma, W. Chu, L. H. Huang, X. P. Yu, Y. Y. Wu, Chin. J. Catal., 2011, 32, 970-977.
[41] X. H. Guo, Y. Li, W. Song, W. J. Shen, Catal. Lett., 2011, 141, 1458-1463.
[42] X. W. Du, S. P. Luo, H. Y. Du, M. Tang, X. D. Huang, P. K. Shen, J. Mater. Chem. A, 2016, 4, 1579-1585.
[43] Y. C. Wei, X. Ren, H. M. Ma, X. Sun, Y. Zhang, X. Kuang, T. Yan, H. X. Ju, D. Wu, Q. Wei, Chem. Commun., 2018, 54, 1533-1536.
[44] L. Predoana, B. Malic, M. Kosec, M. Carata, M. Caldararu, M. Zaharescu, J. Eur. Ceram. Soc., 2007, 27, 4407-4411.
[45] L. Zhao, T. Han, H. Wang, L. H. Zhang, Y. Liu, Appl. Catal. B, 2016, 187, 19-29.
[46] Z. W. Huang, K. J. Barnett, J. P. Chada, Z. J. Brentzel, Z. R. Xu, J. A. Dumesic, G. W. Huber, ACS Catal., 2017, 7, 8429-8440.
[47] A. A. A. da Silva, M. C. Ribeiro, D. C. Cronauer, A. J. Kropf, C. L. Marshall, P. Gao, G. Jacobs, B. H. Davis, F. B. Noronha, L. V. Mattos, Top. Catal., 2014, 57, 637-655.
[48] C. Zhou, X. Liu, C. Z. Wu, Y. W. Wen, Y. J. Xue, R. Chen, Z. L. Zhang, B. Shan, H. F. Yin, W. G. Wang, Phys. Chem. Chem. Phys., 2014, 16, 5106-5112.
[49] D. P. Liu, X. Y. Quek, H. H. A. Wah, G. M. Zeng, Y. H. Li, Y. Yang, Catal. Today, 2009, 148, 243-250.
[50] E. A. Cepeda, U. Iriarte-Velasco, B. Calvo, I. Sierra, J. Am. Oil. Chem. Soc., 2016, 93, 731-741.

Selective hydrogenolysis of furfuryl alcohol to 1,5-and 1,2-pentanediol over Cu-LaCoO₃ catalysts with balanced Cu⁰-CoO sites

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

share this article

References

Related Articles 9

Recommended Articles

Metrics

[1]	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.
[2]	Qianqian Guo, Fan Yang, Xiaohui Liu, Mengqing Sun, Yong Guo, Yanqin Wang. Low-cost synthesis of nanoaggregate SAPO-34 and its application in the catalytic alcoholysis of furfuryl alcohol [J]. Chinese Journal of Catalysis, 2020, 41(11): 1772-1781.
[3]	Man Yang, Xiaochen Zhao, Yujing Ren, Jia Wang, Nian Lei, Aiqin Wang, Tao Zhang. Pt/Nb-WO_x for the chemoselective hydrogenolysis of glycerol to 1,3-propanediol: Nb dopant pacifying the over-reduction of WO_x supports [J]. Chinese Journal of Catalysis, 2018, 39(6): 1027-1037.
[4]	Hailong Liu, Zhiwei Huang, Haixiao Kang, Chungu Xia, Jing Chen . Selective hydrogenolysis of biomass-derived furfuryl alcohol into 1,2-and 1,5-pentanediol over highly dispersed Cu-Al₂O₃ catalysts [J]. Chinese Journal of Catalysis, 2016, 37(5): 700-710.
[5]	Yuqing Jia, Haichao Liu. Selective hydrogenolysis of sorbitol to ethylene glycol and propylene glycol on ZrO₂-supported bimetallic Pd-Cu catalysts [J]. Chinese Journal of Catalysis, 2015, 36(9): 1552-1559.
[6]	Sanjay Srivastava, Pravakar Mohanty, Jigisha K. Parikh, Ajay K. Dalai, S. S. Amritphale, Anup K. Khare. Cr-free Co-Cu/SBA-15 catalysts for hydrogenation of biomass-derived α-, β-unsaturated aldehyde to alcohol [J]. Chinese Journal of Catalysis, 2015, 36(7): 933-942.
[7]	Shuai Wang, Haichao Liu. Selective hydrogenolysis of glycerol to propylene glycol on hydroxycarbonate-derived Cu-ZnO-Al₂O₃ catalysts [J]. Chinese Journal of Catalysis, 2014, 35(5): 631-643.
[8]	XIA Ming-Yu, CAO Xiao-Xia, NI Zhe-Ming, SHI Wei, FU Xiao-Wei. Reaction Mechanism for 2-Methylfuran Formation during Hydrogenation of Furfuryl Alcohol Catalyzed by Cu(111) Plane [J]. Chinese Journal of Catalysis, 2012, 33(6): 1000-1006.
[9]	ZHENG Liangke;XU Chenghua*;LIANG Wenbiao;LIU Jianying;LIU Jun;DUN Xingjie;GUO Yan;YANG Yingchun. Furfural Hydrogenation over Cu-Containing Catalysts Obtained from Hydro-talcite-Type Precursors [J]. Chinese Journal of Catalysis, 2010, 31(4): 461-465.