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Acta Chimica Sinica >

2023 , Vol. 81 >Issue 5: 533 - 547

DOI: https://doi.org/10.6023/A23020042

Review

Heterogeneous Catalysts for Selective Hydrogenolysis of Biomass-derived Polyols★

  • Lujie Liu ,
  • Jian Zhang ,
  • Liang Wang ,
  • Fengshou Xiao
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  • a Key Lab of Biomass Chemical Engineering of Ministry of Education, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou, Zhejiang 310027
    b Beijing Advanced Innovation Center for Soft Matter, Science and Engineering, Beijing University of Chemical Technology, Beijing 100029
†★Dedicated to the 90th anniversary of Acta Chimica Sinica.
*E-mail:

Received date: 2023-02-21

  Online published: 2023-03-28

Supported by

National Natural Science Foundation of China(22202176); China Postdoctoral Science Foundation(2021M702802)

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Abstract

Catalytic transformation of biomass-derived polyols into valuable chemicals has attracted attention from the viewpoint on using renewable carbon resources. Therefore, it is important for design and preparation of heterogeneous catalysts with high activity, high selectivity, and high stability for the selective conversion of biomass-derived polyols. Recently, it has been reported the selective production of mono-alcohols and/or diols by selective hydrogenolysis of sugar alcohols, where the Ir-ReOx and Pt-WOx as typical heterogeneous catalysts are highly efficient. In this review, we briefly summarized the routes for the selective conversion of sugar alcohols into mono-alcohols and/or diols, where the metal-metal oxide interaction for catalyst design, relationship between catalyst structure and performance, and reaction mechanism for the C—O hydrogenolysis are particularly discussed. In addition, the future trend for the selective hydrogenolysis of sugars is also prospected. This review might be helpful for design of novel heterogeneous catalysts in sugar alcohol conversion.

Key words： biomass-derived polyols; sugar alcohols; heterogeneous catalyst; bifunctional catalyst; hydrodeoxygenation; selective hydrogenolysis

Cite this article

Lujie Liu , Jian Zhang , Liang Wang , Fengshou Xiao . Heterogeneous Catalysts for Selective Hydrogenolysis of Biomass-derived Polyols★[J]. Acta Chimica Sinica, 2023 , 81(5) : 533 -547 . DOI: 10.6023/A23020042

References

[1]
Botkin, D. B.; Saxe, H.; Araujo, M. B.; Betts, R.; Bradshaw, R. H.; Cedhagen, T.; Chesson, P.; Dawson, T. P.; Etterson, J. R.; Faith, D. P. Bioscience 2007, 57, 227.
[2]
Trenberth, K. E.; Dai, A.; Van Der Schrier, G.; Jones, P. D.; Barichivich, J.; Briffa, K. R.; Sheffield, J. Nat. Clim. Chang. 2014, 4, 17.
[3]
Galdos, M.; Cavalett, O.; Seabra, J. E.; Nogueira, L. A. H.; Bonomi, A. Appl. Energy 2013, 104, 576.
[4]
Duan, L.; Cao, L.; Bala, G.; Caldeira, K. J. Geophys. Res. Atmos. 2020, 125, e2019JD031883.
[5]
McGlade, C.; Ekins, P. Nature 2015, 517, 187.
[6]
Tian, Z.; Da, W.; Wang, L.; Yang, Y.; Wei, M. Acta Chim. Sinica 2022, 80, 1322. (in Chinese)
[6]
(田钊炜, 达伟民, 王雷, 杨宇森, 卫敏, 化学学报, 2022, 80, 1322.)
[7]
Pagliaro, M.; Ciriminna, R.; Kimura, H.; Rossi, M.; Della?Pina, C. Angew. Chem., nt. Ed. 2007, 46, 4434.
[8]
Sun, D.; Yamada, Y.; Sato, S.; Ueda, W. Appl. Catal. B 2016, 193, 75.
[9]
Nakagawa, Y.; Kasumi, T.; Ogihara, J.; Tamura, M.; Arai, T.; Tomishige, K. ACS Omega 2020, 5, 2520.
[10]
Zhang, L.; Qiu, J.; Tang, X.; Sun, Y.; Zeng, X.; Lin, L. Chin. J. Chem. 2021, 39, 2467.
[11]
Zada, B.; Chen, M.; Chen, C.; Yan, L.; Xu, Q.; Li, W.; Guo, Q.; Fu, Y. Sci. Chin. Chem. 2017, 60, 853.
[12]
Ruppert, A. M.; Weinberg, K.; Palkovits, R. Angew. Chem., nt. Ed. 2012, 51, 2564.
[13]
Liu, S. B.; Okuyama, Y.; Tamura, M.; Nakagawa, Y.; Imai, A.; Tomishige, K. Green Chem. 2016, 18, 165.
[14]
Jin, X.; Shen, J.; Yan, W.; Zhao, M.; Thapa, P. S.; Subramaniam, B.; Chaudhari, R. V. ACS Catal. 2015, 5, 6545.
[15]
Liu, H.; Huang, Z.; Kang, H.; Li, X.; Xia, C.; Chen, J.; Liu, H. Appl. Catal. B 2018, 220, 251.
[16]
Sun, J.; Liu, H. Green Chem. 2011, 13, 135.
[17]
Tazawa, S.; Ota, N.; Tamura, M.; Nakagawa, Y.; Okumura, K.; Tomishige, K. ACS Catal. 2016, 6, 6393.
[18]
Cortright, R. D.; Davda, R. R.; Dumesic, J. A. Nature 2002, 418, 964.
[19]
Robinson, A. M.; Hensley, J. E.; Medlin, J. W. ACS Catal. 2016, 6, 5026.
[20]
Zhao, J.; Yu, W.; Chen, C.; Miao, H.; Ma, H.; Xu, J. Catal. Lett. 2010, 134, 184.
[21]
Tomishige, K.; Nakagawa, Y.; Tamura, M. Green Chem. 2017, 19, 2876.
[22]
Zhao, H.; Zheng, L.; Li, X.; Chen, P.; Hou, Z. Catal. Today 2020, 355, 84.
[23]
Nakagawa, Y.; Tamura, M.; Tomishige, K. Res. Chem. Intermed. 2018, 44, 3879.
[24]
Nakagawa, Y.; Tamura, M.; Tomishige, K. J. Mater. Chem. A 2014, 2, 6688.
[25]
Nakagawa, Y.; Tomishige, K. Catal. Sci. Technol. 2011, 1, 179.
[26]
Zhou, C.; Beltramini, J.; Fan, Y.; Lu, G. Chem. Soc. Rev. 2008, 37, 527.
[27]
Zhang, D.; Zhang, Q.; Zhou, Z.; Li, Z.; Meng, K.; Fang, T.; You, Z.; Zhang, G.; Yin, B.; Shen, J.; Yang, C.; Yan, W.; Jin, X. ChemCatChem 2022, 14, e202101316.
[28]
Guo, X.; Yin, A.; Guo, X.; Guo, X.; Dai, W.; Fan, K. Chin. J. Chem. 2011, 29, 1563.
[29]
Lei, N.; Miao, Z.; Liu, F.; Wang, H.; Pan, X.; Wang, A.; Zhang, T. Chin. J. Catal. 2020, 41, 1261.
[30]
Gilkey, M. J.; Xu, B. ACS Catal. 2016, 6, 1420.
[31]
Zhu, S.; Gao, X.; Zhu, Y.; Zhu, Y.; Zheng, H.; Li, Y. J. Catal. 2013, 303, 70.
[32]
Arundhathi, R.; Mizugaki, T.; Mitsudome, T.; Jitsukawa, K.; Kaneda, K. ChemSusChem 2013, 6, 1345.
[33]
Zhao, B.; Liang, Y.; Liu, L.; He, Q.; Dong, J. Green Chem. 2020, 22, 8254.
[34]
Liu, L.; Asano, T.; Nakagawa, Y.; Gu, M.; Li, C.; Tamura, M.; Tomishige, K. Appl. Catal. B 2021, 292, 120164.
[35]
Zhou, W.; Li, Y.; Wang, X. F.; Yao, D. W.; Wang, Y.; Huang, S. Y.; Li, W.; Zhao, Y. J.; Wang, S. P.; Ma, X. B. J. Catal. 2020, 388, 154.
[36]
Nakagawa, Y.; Shinmi, Y.; Koso, S.; Tomishige, K. J. Catal. 2010, 272, 191.
[37]
Amada, Y.; Shinmi, Y.; Koso, S.; Kubota, T.; Nakagawa, Y.; Tomishige, K. Appl. Catal. B 2011, 105, 117.
[38]
Nakagawa, Y.; Ning, X. H.; Amada, Y.; Tomishige, K. Appl. Catal. A 2012, 433, 128.
[39]
Liu, L.; Asano, T.; Nakagawa, Y.; Tamura, M.; Okumura, K.; Tomishige, K. ACS Catal. 2019, 9, 10913.
[40]
Liu, L.; Kawakami, S.; Nakagawa, Y.; Tamura, M.; Tomishige, K. Appl. Catal. B 2019, 256, 117775.
[41]
Shinmi, Y.; Koso, S.; Kubota, T.; Nakagawa, Y.; Tomishige, K. Appl. Catal. B 2010, 94, 318.
[42]
Huang, L.; Zhu, Y.; Zheng, H.; Ding, G.; Li, Y. Catal. Lett. 2009, 131, 312.
[43]
Cai, F.; Song, X.; Wu, Y.; Zhang, J.; Xiao, G. ACS Sustainable Chem. Eng. 2018, 6, 110.
[44]
Zhu, S.; Gao, X.; Zhu, Y.; Zhu, Y.; Xiang, X.; Hu, C.; Li, Y. Appl. Catal. B 2013, 140-141, 60.
[45]
García-Fernández, S.; Gandarias, I.; Requies, J.; Güemez, M. B.; Bennici, S.; Auroux, A.; Arias, P. L. J. Catal. 2015, 323, 65.
[46]
García-Fernández, S.; Gandarias, I.; Requies, J.; Soulimani, F.; Arias, P. L.; Weckhuysen, B. M. Appl. Catal. B 2017, 204, 260.
[47]
Gong, L.; Lu, Y.; Ding, Y.; Lin, R.; Li, J.; Dong, W.; Wang, T.; Chen, W. Appl. Catal. A 2010, 390, 119.
[48]
Zhang, Y.; Zhao, X.; Wang, Y.; Zhou, L.; Zhang, J.; Wang, J.; Wang, A.; Zhang, T. J. Mater. Chem. A 2013, 1, 3724.
[49]
Zhu, S.; Gao, X.; Zhu, Y.; Cui, J.; Zheng, H.; Li, Y. Appl. Catal. B 2014, 158, 391.
[50]
Priya, S. S.; Kumar, V. P.; Kantam, M. L.; Bhargava, S. K.; Srikanth, A.; Chary, K. V. Ind. Eng. Chem. Res. 2015, 54, 9104.
[51]
Fan, Y.; Cheng, S.; Wang, H.; Ye, D.; Xie, S.; Pei, Y.; Hu, H.; Hua, W.; Li, Z. H.; Qiao, M.; Zong, B. Green Chem. 2017, 19, 2174.
[52]
Qin, L.; Song, M.; Chen, C. Green Chem. 2010, 12, 1466.
[53]
Lei, N.; Zhao, X.; Hou, B.; Yang, M.; Zhou, M.; Liu, F.; Wang, A.; Zhang, T. ChemCatChem 2019, 11, 3903.
[54]
Wang, J.; Zhao, X.; Lei, N.; Li, L.; Zhang, L.; Xu, S.; Miao, S.; Pan, X.; Wang, A.; Zhang, T. ChemSusChem 2016, 9, 784.
[55]
Zhou, W.; Luo, J.; Wang, Y.; Liu, J.; Zhao, Y.; Wang, S.; Ma, X. Appl. Catal. B 2019, 242, 410.
[56]
Fan, Y.; Cheng, S.; Wang, H.; Tian, J.; Xie, S.; Pei, Y.; Qiao, M.; Zong, B. Appl. Catal. B 2017, 217, 331.
[57]
Deng, C.; Duan, X.; Zhou, J.; Zhou, X.; Yuan, W.; Scott, S. L. Catal. Sci. Technol. 2015, 5, 1540.
[58]
Takagaki, A. Catal. Sci. Technol. 2016, 6, 791.
[59]
Tajvidi, K.; Hausoul, P. J.; Palkovits, R. ChemSusChem 2014, 7, 1311.
[60]
Amada, Y.; Watanabe, H.; Hirai, Y.; Kajikawa, Y.; Nakagawa, Y.; Tomishige, K. ChemSusChem 2012, 5, 1991.
[61]
Gu, M.; Liu, L.; Nakagawa, Y.; Li, C.; Tamura, M.; Shen, Z.; Zhou, X.; Zhang, Y.; Tomishige, K. ChemSusChem 2021, 14, 642.
[62]
Said, A.; Da Silva Perez, D.; Perret, N.; Pinel, C.; Besson, M. ChemCatChem 2017, 9, 2768.
[63]
Amada, Y.; Ota, N.; Tamura, M.; Nakagawa, Y.; Tomishige, K. ChemSusChem 2014, 7, 2185.
[64]
Chen, K.; Mori, K.; Watanabe, H.; Nakagawa, Y.; Tomishige, K. J. Catal. 2012, 294, 171.
[65]
Liu, L.; Asano, T.; Nakagawa, Y.; Tamura, M.; Tomishige, K. Green Chem. 2020, 22, 2375.
[66]
Liu, L.; Cao, J.; Nakagawa, Y.; Betchaku, M.; Tamura, M.; Yabushita, M.; Tomishige, K. Green Chem. 2021, 23, 5665.
[67]
Arai, T.; Tamura, M.; Nakagawa, Y.; Tomishige, K. ChemSusChem 2016, 9, 1680.
[68]
Liu, B.; Nakagawa, Y.; Li, C.; Yabushita, M.; Tomishige, K. ACS Catal. 2022, 12, 15431.
[69]
Sun, J.; Liu, H. Catal. Today 2014, 234, 75.
[70]
Soták, T.; Schmidt, T.; Hronec, M. Appl. Catal. A 2013, 459, 26.
[71]
Rivie?re, M.; Perret, N. m.; Delcroix, D.; Cabiac, A.; Pinel, C.; Besson, M. ACS Sustainable Chem. Eng. 2018, 6, 4076.
[72]
Zhu, S.; Gao, X.; Zhu, Y.; Li, Y. Green Chem. 2016, 18, 782.
[73]
Zhou, J.; Zhang, M.; Zhao, L.; Li, P.; Zhou, X.; Yuan, W. Catal. Today 2009, 147, S225.
[74]
Leo, I. M.; Granados, M. L.; Fierro, J. L. G.; Mariscal, R. Chin. J. Catal. 2014, 35, 614.
[75]
Jia, Y.; Liu, H. Chin. J. Catal. 2015, 36, 1552.
[76]
Nakagawa, Y.; Tamura, M.; Tomishige, K. Catal. Surv. Asia 2015, 19, 249.
[77]
Lee, J.; Ro, I.; Kim, H.; Kim, Y.; Kwon, E.; Huber, G. Process Saf. Environ. Prot. 2018, 115, 2.
[78]
Farmer, J. A.; Campbell, C. T. Science 2010, 329, 933.
[79]
Lykhach, Y.; Kozlov, S. M.; Skala, T.; Tovt, A.; Stetsovych, V.; Tsud, N.; Dvorak, F.; Johanek, V.; Neitzel, A.; Myslivecek, J.; Fabris, S.; Matolin, V.; Neyman, K. M.; Libuda, J. Nat. Mater. 2016, 15, 284.
[80]
Liu, X. Y.; Liu, M. H.; Luo, Y. C.; Mou, C. Y.; Lin, S. D.; Cheng, H. K.; Chen, J. M.; Lee, J. F.; Lin, T. S. J. Am. Chem. Soc. 2012, 134, 10251.
[81]
Bruix, A.; Rodriguez, J. A.; Ramirez, P. J.; Senanayake, S. D.; Evans, J.; Park, J. B.; Stacchiola, D.; Liu, P.; Hrbek, J.; Illas, F. J. Am. Chem. Soc. 2012, 134, 8968.
[82]
He, J. Y.; Burt, S. P.; Ball, M.; Zhao, D. T.; Hermans, I.; Dumesic, J. A.; Huber, G. W. ACS Catal. 2018, 8, 1427.
[83]
Tauster, S. J.; Fung, S. C.; Garten, R. L. J. Am. Chem. Soc. 1978, 100, 170.
[84]
Zhang, X.; Cui, G.; Feng, H.; Chen, L.; Wang, H.; Wang, B.; Zhang, X.; Zheng, L.; Hong, S.; Wei, M. Nat. Commun. 2019, 10, 1.
[85]
Zhang, J.; Wang, H.; Wang, L.; Ali, S.; Wang, C.; Wang, L.; Meng, X.; Li, B.; Su, D. S.; Xiao, F. J. Am. Chem. Soc. 2019, 141, 2975.
[86]
Wang, H.; Wang, L.; Lin, D.; Feng, X.; Niu, Y.; Zhang, B.; Xiao, F. Nat. Catal. 2021, 4, 418.
[87]
Matsubu, J. C.; Zhang, S. Y.; DeRita, L.; Marinkovic, N. S.; Chen, J. G. G.; Graham, G. W.; Pan, X. Q.; Christopher, P. Nat. Chem. 2017, 9, 120.
[88]
Saavedra, J.; Doan, H. A.; Pursell, C. J.; Grabow, L. C.; Chandler, B. D. Science 2014, 345, 1599.
[89]
Hu, Z.; Nakamura, H.; Kunimori, K.; Asano, H.; Uchijima, T. J. Catal. 1988, 112, 478.
[90]
Ito, S.; Chibana, C.; Nagashima, K.; Kameoka, S.; Tomishige, K.; Kunimori, K. Appl. Catal. A 2002, 236, 113.
[91]
Ito, S.; Ishiguro, S.; Nagashima, K.; Kunimori, K. Catal. Lett. 1998, 55, 197.
[92]
Tomishige, K.; Furikado, I.; Yamagishi, T.; Ito, S.; Kunimori, K. Catal. Lett. 2005, 103, 15.
[93]
Koso, S.; Watanabe, H.; Okumura, K.; Nakagawa, Y.; Tomishige, K. J. Phys. Chem. C 2012, 116, 3079.
[94]
Amada, Y.; Watanabe, H.; Tamura, M.; Nakagawa, Y.; Okumura, K.; Tomishige, K. J. Phys. Chem. C 2012, 116, 23503.
[95]
Mondelli, C.; G?zayd?n, G.; Yan, N.; Pérez-Ramírez, J. Chem. Soc. Rev. 2020, 49, 3764.
[96]
Li, C.; Nakagawa, Y.; Yabushita, M.; Nakayama, A.; Tomishige, K. ACS Catal. 2021, 11, 12794.
[97]
Wang, C.; Wang, Z.; Mao, S.; Chen, Z.; Wang, Y. Chin. J. Catal. 2022, 43, 928.
[98]
Li, S.; Xu, Y., Chen, Y.; Li, W.; Lin, L.; Li, M.; Deng, Y.; Wang, X.; Ge, B.; Yang, C.; Yao, S.; Xie, J.; Li, Y.; Liu, X.; Ma, D. Angew. Chem., Int. Ed. 2017, 56, 10761.
[99]
Wang, J.; Yang, M.; Wang, A. Chin. J. Catal. 2020, 41, 1311.
[100]
Cheng, S.; Zeng, Y.; Pei, Y.; Fan, K.; Qiao, M.; Zong, B. Acta Chim. Sinica 2019, 77, 1054. (in Chinese)
[100]
(成诗婕, 曾杨, 裴燕, 范康年, 乔明华, 宗保宁, 化学学报, 2019, 77, 1054.)
[101]
Zeng, Y.; Jiang, L.; Zhang, X.; Xie, S.; Pei, Y.; Qiao, M.; Li, Z.; Xu, H.; Fan, K.; Zong, B. Acta Chim. Sinica 2022, 80, 903. (in Chinese)
[101]
(曾杨, 姜兰, 张晓昕, 谢颂海, 裴燕, 乔明华, 李振华, 徐华龙, 范康年, 宗保宁, 化学学报, 2022, 80, 903.)
[102]
Akita, T.; Okumura, M.; Tanaka, K.; Tsubota, S.; Haruta, M. J. Electron Microsc. 2003, 52, 119.
[103]
Aranda-Perez, N.; Ruiz, M. P.; Echave, J.; Faria, J. Appl. Catal. A 2017, 531, 106.
[104]
Koso, S.; Nakagawa, Y.; Tomishige, K. J. Catal. 2011, 280, 221.
[105]
Varghese, J. J.; Cao, L.; Robertson, C.; Yang, Y.; Gladden, L. F.; Lapkin, A. A.; Mushrif, S. H. ACS Catal. 2019, 9, 485.
[106]
Chia, M.; Pagán-Torres, Y. J.; Hibbitts, D.; Tan, Q.; Pham, H. N.; Datye, A. K.; Neurock, M.; Davis, R. J.; Dumesic, J. A. J. Am. Chem. Soc. 2011, 133, 12675.
[107]
Stephens, K. J.; Allgeier, A. M.; Bell, A. L.; Carlson, T. R.; Cheng, Y.; Douglas, J. T.; Howe, L. A.; Menning, C. A.; Neuenswander, S. A.; Sengupta, S. K.; Thapa, P. S.; Ritter, J. C. ACS Catal. 2020, 10, 12996.
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