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化学进展 2023, Vol. 35 Issue (4): 593-605 DOI: 10.7536/PC220928 前一篇   后一篇

• 综述 •

多相双功能催化剂催化乙酰丙酸制备γ-戊内酯

邵月文, 李清扬, 董欣怡, 范梦娇, 张丽君, 胡勋*()   

  1. 济南大学 材料科学与工程学院 济南 250022
  • 收稿日期:2022-09-26 修回日期:2022-11-10 出版日期:2023-04-24 发布日期:2023-02-20
  • 作者简介:

    胡 勋 济南大学教授、博导,国家海外高层次人才引进计划青年项目获得者。团队目前的研究包括固体废弃物资源化利用、生物质炭材料制备和应用、多相催化(水蒸气重整制氢、加氢和酸催化等)。团队在Nature Communication, Chemical Communications, ChemSusChem, AICHE Journal, Green Chemistry,ACS Sustainable Chemistry & Engineering和Applied Catalysis B: Environmental等本领域重要期刊发表论文200余篇,文章被引12 000余次。

  • 基金资助:
    国家自然科学基金项目(51906084); 山东省泰山学者资助项目; 山东省八三石墨新材料厂研发项目; 吉林省科学技术发展项目(S202110427093)
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Heterogeneous Bifunctional Catalysts for Catalyzing Conversion of Levulinic Acid to γ-Valerolactone

Yuewen Shao, Qingyang Li, Xinyi Dong, Mengjiao Fan, Lijun Zhang, Xun Hu()   

  1. School of Material Science and Engineering, University of Jinan,Jinan 250022, China
  • Received:2022-09-26 Revised:2022-11-10 Online:2023-04-24 Published:2023-02-20
  • Contact: *e-mail: xun.hu@outlook.com
  • Supported by:
    National Natural Science Foundation of China(51906084); Program for Taishan Scholars of Shandong Province Government; R&D program of Shandong Basan Graphite New Material Plant and Innovation; Entrepreneurship Training Program for College Students of Shandong Province(S202110427093)

乙酰丙酸是重要的生物质衍生物,通过多相双功能催化剂催化转化其制备γ-戊内酯(GVL)成为生物精炼领域的研究热点。本文综述了近年来贵金属以及非贵金属双功能催化剂催化乙酰丙酸及其酯直接加氢制备GVL,以及金属负载型、改性分子筛和混合金属氧化物等双功能催化剂催化乙酰丙酸及其酯转移加氢制备GVL。在双功能催化剂作用下,乙酰丙酸及其酯通过羰基加氢和后续内酯化反应两个过程生成GVL。本文详细研究了不同双功能催化剂中活性位点在反应路径中的重要性,讨论了不同双功能催化剂在乙酰丙酸加氢转化过程中存在的优势和问题,并对未来双功能催化剂的开发和GVL的合成进行展望。

关键词： 乙酰丙酸, γ-戊内酯, 多相双功能催化剂, 加氢, 内酯化

Levulinic acid is important biomass-derived compounds, and catalytic conversion of them to γ-valerolactone (GVL) over heterogeneous bifunctional catalysts has become a hot focus in the field of biorefining. In this paper, the direct hydrogenation of levulinic acid and its esters to GVL catalyzed by noble and non-noble metal bifunctional catalysts, and the transfer hydrogenation of levulinic acid and its esters to GVL catalyzed by the bifunctional catalysts, such as metal-supported catalysts, modified zeolite, and mixed metal oxides, are reviewed. Conversion of levulinic acid and its esters to GVL over bifunctional catalysts involves two steps, including hydrogenation of carbonyl group and subsequent lactonization reaction. In addition, the importance of active sites of various bifunctional catalysts in conversion of levulinic acid and its esters is studied in this paper, and the advantages and problems of different catalysts during the conversion of levulinic acid/esters are discussed. Finally, the development of bifunctional catalysts and the synthesis of GVL in the future are prospected.

Key words: levulinic acid, γ-valerolactone, heterogeneous bifunctional catalysts, hydrogenation, lactonization
()
图1 木质纤维素生物质催化转化制备γ-戊内酯反应路线
Fig.1 Reaction routes for catalytic conversion of lignocellulosic biomass to γ-valerolactone
图2 金属双功能催化剂催化转化乙酰丙酸及其酯制备γ-戊内酯
Fig.2 Conversion of levulinic acid and its esters to γ-valerolactone catalyzed by metal bifunctional catalysts
表1 不同贵金属双功能催化剂催化转化乙酰丙酸及其酯制备γ-戊内酯
Table 1 Conversion of levulinic acid and its esters to γ-valerolactone catalyzed by different noble metal bifunctional catalysts
Entry Catalysts T (℃) P H 2 (MPa) t (h) Solvent Con. (%) Yield (%) ref
1 Ru/rGO 50 2.0 0.67 H2O 100.0-LA 18.0 22
2 Ru/rGO-S 50 2.0 0.67 H2O 100.0-LA 82.0 22
3 Ru/C + A70 70 0.5 3 H2O 98.0-LA 98.0 23
4 Ru/OMC-P 70 0.7 6 H2O 98.0-LA 92.1 24
5 Ru/HfO2@CN 80 1 3 H2O 100.0-LA 92.0 25
6 Ru/N@CNTs 80 1 1 H2O 100.0-LA 99.0 26
7 Ru/DOWEX 70 1 4 H2O 98.3-LA 98.0 27
8 Ru/MCM-49(DP) 160 2.5 0.5 H2O 94.3-LA 93.4 28
9 Ru-Mn(0.7)/MCM-49 160 2.5 3 H2O 98.0-LA 98.0 29
10 Ru/Zr10SMS 70 0.5 3 H2O 98.4-LA 94.5 30
11 Ru/SMS 70 0.5 3 H2O 99.2-LA 95.6 30
12 Ru/(AlO)(ZrO)0.1 120 1 6 H2O 100.0-LA 100.0 31
13 Ru/NbOPO4/SBA-15a 100 1 - H2O 100.0-LA 86.0 32
14 Ru/TiO2 70 5 1 H2O 100.0-LA 100.0 33
15 Ru/MIL-101(Cr) 70 1 5 H2O 100.0-LA 99.0 34
16 Ru/SPES 70 3 2 H2O 87.9-LA 87.9 35
17 Ru/HAP 70 0.5 4 H2O 99.0-LA 99.0 36
18 Pd/HAP 70 0.5 4 H2O 26.0-LA 23.4 36
19 Pd/CeO2 90 0.4 1.5 2-PrOH 100.0-LA 99.9 37
20 Pd@ND 150 0.5 12 H2O 100.0-LA 96.0 38
21 Pd@mSiO2 200 3.0 4 dioxane 95.0-LA 91.2 39
22 5 wt% Pd/MCM-41 240 6.0 10 H2O 100.0-LA 96.3 40
23 Pt/HAP 70 0.5 4 H2O 42.0-LA 37.0 36
24 Pt/Y-C18TAOH 120 2.5 6 H2O 100.0-LA 94.0 41
表2 不同非贵金属双功能催化剂催化转化乙酰丙酸及其酯制备γ-戊内酯
Table 2 Conversion of levulinic acid and its esters to γ-valerolactone catalyzed by different non-noble metal bifunctional catalysts
Entry Catalysts T (℃) P H 2 (MPa) t (h) Solvent Con. (%) Yield (%) ref
1 Ni/Al2O3-CN-600 130 0.5 3 THF 100.0-LA 99.0 42
2 Ni@C 200 3 4 Dioxane 100.0-LA 100.0 43
3 Ni/C-500 200 1 5 Dioxane 100.0-LA 98.2 44
4 Ni-Mo/C 200 10 2 Dioxane 100.0-LA 100.0 45
5 Ni/H-ZSM-5a 320 - - - 98.6-LA 98.6 46
6 Ni/Al2O3 200 5 4 2-PrOH 92.0-LA 92.0 47
7 Ni/MgO-Al2O3 160 3 1 Dioxane 99.7-LA 99.7 48
8 Ni/SiO2-Al2O3 200 1.58 0.5 THF 100.0-LA 100.0 49
9 Ni-Al 170 5 2 H2O 100.0-LA 99.0 50
10 CeNi/Si O 2 a 275 AT. - - 82.5-LA 79.3 51
11 Ni(OAc)2·4H2O/DPPP 180 1 10 Free 100.0-LA 95.1 52
12 Co@NC-700 190 1.9 2 Dioxane 100.0-LA 100.0 53
13 Co/Ya 200 - - - 99.0-LA 80.0 54
14 Co-LA@SiO2-800 120 3 24 Dioxane 100.0-LA 96.0 55
15 Co/SiO2(8.1)a 200 3 - - 100.0-EL 98.0 56
16 Co-Al 150 3 2 H2O 100.0-EL 98.0 57
17 2.1Co-0.9Mg-Al 150 3 2 H2O 100.0-EL 97.0 57
18 Cu/Zr-Al-3 170 3 5 H2O 100.0-LA 100.0 58
19 CuAl 110 3 2 Ethanol 100.0-LA 95.3 59
20 3Cu/Zr0.8-C e 0.2 a 260 0.5 - - 88.5-LA 83.4 60
21 Ni/Cu/Al/Fe 150 5 3 Methanol 100.0-LA 99.0 61
22 Ni4.59Cu1Mg1.58Al1.96Fe0.70 142 2 3 Methanol 100.0-LA 98.1 62
23 Ni2Co1P 180 3 4 Free 100.0-LA 100.0 63
24 Cu-Ni/Al2O3-ZrO2 220 3 0.33 2-Butanol 100.0-LA 99.9 64
25 Cu-Ni/Al2O3 180 2.5 6 Ethanol 99.0-EL 97.0 65
图3 双功能催化剂催化乙酰丙酸及其酯转移加氢制备γ-戊内酯
Fig.3 Transfer hydrogenation of levulinic acid and its ester to γ-valerolactone catalyzed by bifunctional catalysts
表3 不同双功能催化剂催化乙酰丙酸及其酯转移加氢制备γ-戊内酯
Table 3 Transfer hydrogenation of levulinic acid and its ester to γ-valerolactone catalyzed by different bifunctional catalysts
Entry Catalysts T(℃) t (h) Solvent Con. (%)a Yield (%) ref
1 Ru/g-C3N4 100 12 2-Propanol 100.0-LA 99.8 66
2 Ru(OH)x/TiO2 90 24 2-Propanol 100.0-ML 80.0 67
3 Ni/E-cats 180 6 2-Propanol 90.3-EL 86.9 68
4 CuNi-0.4Al/AC 220 2 2-Propanol 100.0-LA 97.2 69
5 Ni3P-CePO4(0.1) 180 2 2-Propanol 99.9-LA 89.9 70
6 Ni/ZrO2 100 20 2-Propanol 100.0-ML 94.0 71
7 Cu/AC 200 7 2-Propanol 100.0-LA 89.9 72
8 Hf@CCSO3H 200 24 2-Propanol 100.0-LA 96.0 73
9 Zr-beta 118 10 2-Propanol 100.0-LA 96.0 74
10 Zr-Al-Beta 170 24 2-Propanol 100.0-LA 85.5 75
11 SnO2/SBA-15 110 8 2-Propanol 85.0-LA 80.8 76
12 GluPC-Zr 190 12 2-Propanol 100.0-LA 98.1 77
13 ZrO2(10)/SBA-15 150 3 2-Propanol 100.0-LA 90.0 78
14 ZrFeO(1:3)-300 230 3 Ethanol 100.0-EL 87.2 79
15 ZrO2 150 16 2-Butanol 100.0-LA 92.0 80
16 Zr1Fe1-150 200 1 2-Propanol 100.0-LA 96.7 81
17 Mn2CoOx 230 9 Formic acid 80.0-LA 77.0 82
18 ZrF MOFs 200 2 2-Propanol 98.0-LA 96.0 83
19 Zr-humic acids 150 3 2-Propanol 96.4-EL 75.8 84
20 UiO-66-S60 140 24 2-Butanol 98.0-ML 82.0 85
21 HPW@MOF-808 160 6 2-Propanol 100.0-LA 87.0 86
图4 双功能催化剂中活性位点在催化乙酰丙酸及其酯 (a)直接加氢和 (b)转移加氢制备γ-戊内酯的重要性
Fig.4 Importance of active sites in bifunctional catalysts in catalyzing (a) direct hydrogenation and (b) transfer hydrogenation of levulinic acid and its esters to γ-valerolactone
[1]
Yang H P, Yan R, Chen H P, Lee D H, Zheng C G. Fuel, 2007, 86(12/13): 1781.

doi: 10.1016/j.fuel.2006.12.013     URL    
[2]
Huang X, Ren J, Ran J Y, Qin C L, Yang Z Q, Cao J P. Fuel Process. Technol., 2022, 229: 107175.

doi: 10.1016/j.fuproc.2022.107175     URL    
[3]
Jing Y X, Guo Y, Xia Q N, Liu X H, Wang Y Q. Chem, 2019, 5(10): 2520.

doi: 10.1016/j.chempr.2019.05.022     URL    
[4]
Yan K, Jarvis C, Gu J, Yan Y. Renew. Sustain. Energy Rev., 2015, 51: 986.

doi: 10.1016/j.rser.2015.07.021     URL    
[5]
Hu X, Jiang S J, Wu L P, Wang S, Li C Z. Chem. Commun., 2017, 53(20): 2938.

doi: 10.1039/C7CC01078H     URL    
[6]
Gao W R, Wu G, Zhu X, Asif Akhtar M, Lin G Y, Hu X, Huang Y, Zhang S, Zhang H. Bioresour. Technol., 2022, 347: 126436.

doi: 10.1016/j.biortech.2021.126436     URL    
[7]
Hu X, Li C Z. Green Chem., 2011, 13(7): 1676.

doi: 10.1039/c1gc15272f     URL    
[8]
Wang J H, Cui H Y, Wang J G, Li Z H, Wang M, Yi W M. Chem. Eng. J., 2021, 415: 128922.

doi: 10.1016/j.cej.2021.128922     URL    
[9]
Hu X, Song Y, Wu L P, Gholizadeh M, Li C Z. ACS Sustainable Chem. Eng., 2013, 1(12): 1593.

doi: 10.1021/sc400229w     URL    
[10]
Wang J H, Xiang Z Y, Huang Z X, Xu Q, Yin D L. Front. Chem., 2022, 10: 959572.

doi: 10.3389/fchem.2022.959572     URL    
[11]
Liguori F, Moreno-Marrodan C, Barbaro P. ACS Catal., 2015, 5(3): 1882.

doi: 10.1021/cs501922e     URL    
[12]
Liu Y X, Liu X X, Li M R, Meng Y, Li J, Zhang Z H, Zhang H. Front. Chem., 2021, 9: 812331.

doi: 10.3389/fchem.2021.812331     URL    
[13]
Yu Z H, Lu X B, Xiong J, Ji N. ChemSusChem, 2019, 12(17): 3915.

doi: 10.1002/cssc.v12.17     URL    
[14]
Alonso D M, Wettstein S G, Dumesic J A. Green Chem., 2013, 15(3): 584.

doi: 10.1039/c3gc37065h     URL    
[15]
Dutta S, Yu I K M, Tsang D C W, Ng Y H, Ok Y S, Sherwood J, Clark J H. Chem. Eng. J., 2019, 372: 992.

doi: 10.1016/j.cej.2019.04.199     URL    
[16]
He J, Li H, Xu Y F, Yang S. Renew. Energy, 2020, 146: 359.

doi: 10.1016/j.renene.2019.06.105     URL    
[17]
Winoto H P, Ahn B S, Jae J. J. Ind. Eng. Chem., 2016, 40: 62.

doi: 10.1016/j.jiec.2016.06.007     URL    
[18]
Li W K, Cai Z, Li H, Shen Y, Zhu Y Q, Li H C, Zhang X B, Wang F M. Mol. Catal., 2019, 472: 17.
[19]
Winoto H P, Ali Fikri Z, Ha J M, Park Y K, Lee H, Suh D J, Jae J. Appl. Catal. B Environ., 2019, 241: 588.

doi: 10.1016/j.apcatb.2018.09.031     URL    
[20]
Chen B F, Li F B, Huang Z J, Yuan G Q. J. Energy Chem., 2016, 25(5): 888.

doi: 10.1016/j.jechem.2016.06.007     URL    
[21]
Zhu S H, Cen Y L, Guo J, Chai J C, Wang J G, Fan W B. Green Chem., 2016, 18(20): 5667.

doi: 10.1039/C6GC01736C     URL    
[22]
Wang Y, Rong Z M, Wang Y, Wang T, Du Q Q, Wang Y, Qu J P. ACS Sustainable Chem. Eng., 2017, 5(2): 1538.

doi: 10.1021/acssuschemeng.6b02244     URL    
[23]
Galletti A M R, Antonetti C, De Luise V, Martinelli M. Green Chem., 2012, 14(3): 688.

doi: 10.1039/c2gc15872h     URL    
[24]
Villa A, Schiavoni M, Chan-Thaw C E, Fulvio P F, Mayes R T, Dai S, More K L, Veith G M, Prati L. ChemSusChem, 2015, 8(15): 2520.

doi: 10.1002/cssc.201500331     URL    
[25]
Pan J P, Xu Q H, Fang L, Tu G M, Fu Y H, Chen G H, Zhang F M, Zhu W D. Catal. Commun., 2019, 128: 105710.

doi: 10.1016/j.catcom.2019.105710     URL    
[26]
Meng Z, Liu Y, Yang G X, Cao Y H, Wang H J, Peng F, Liu P F, Yu H. ACS Sustainable Chem. Eng., 2019, 7(19): 16501.

doi: 10.1021/acssuschemeng.9b03742     URL    
[27]
Moreno-Marrodan C, Barbaro P. Green Chem., 2014, 16(7): 3434.

doi: 10.1039/c4gc00298a     URL    
[28]
Li W L, Li F, Chen J W, Betancourt L E, Tu C Y, Liao M J, Ning X, Zheng J J, Li R F. Ind. Eng. Chem. Res., 2020, 59(39): 17338.

doi: 10.1021/acs.iecr.0c01318     URL    
[29]
Li W L, Li F, Ning X, Deng K X, Chen J W, Zheng J J, Li R F. Carbon Resour. Convers., 2022, 5(3): 185.

doi: 10.1016/j.crcon.2022.05.003     URL    
[30]
Kuwahara Y, Magatani Y, Yamashita H. Catal. Today, 2015, 258: 262.

doi: 10.1016/j.cattod.2015.01.015     URL    
[31]
Lu Y W, Wang Y X, Wang Y H, Cao Q E, Xie X G, Fang W H. Mol. Catal., 2020, 493: 111097.
[32]
Mani M, Mariyaselvakumar M, Samikannu A, Panda A B, Konwar L J, Mikkola J P. Appl. Catal. A Gen., 2022, 643: 118744.

doi: 10.1016/j.apcata.2022.118744     URL    
[33]
Ruppert A M, Grams J, Jędrzejczyk M, Matras-Michalska J, Keller N, Ostojska K, Sautet P. ChemSusChem, 2015, 8(9): 1497.

doi: 10.1002/cssc.201500305     URL    
[34]
Guo Y Y, Li Y L, Chen J Z, Chen L M. Catal. Lett., 2016, 146(10): 2041.

doi: 10.1007/s10562-016-1819-1     URL    
[35]
Yao Y R, Wang Z Q, Zhao S, Wang D H, Wu Z J, Zhang M H. Catal. Today, 2014, 234: 245.

doi: 10.1016/j.cattod.2014.01.020     URL    
[36]
Sudhakar M, Lakshmi Kantam M, Swarna Jaya V, Kishore R, Ramanujachary K V, Venugopal A. Catal. Commun., 2014, 50: 101.

doi: 10.1016/j.catcom.2014.03.005     URL    
[37]
Zhang Y, Chen C, Gong W B, Song J Y, Zhang H M, Zhang Y X, Wang G Z, Zhao H J. Catal. Commun., 2017, 93: 10.

doi: 10.1016/j.catcom.2017.01.008     URL    
[38]
Gupta N, Dimitratos N, Su D S, Villa A. Energy Technol., 2019, 7(2): 269.

doi: 10.1002/ente.v7.2     URL    
[39]
Liu Y, Xin Q H, Yin D F, Liu S W, Li L, Xie C X, Yu S T. Catal. Lett., 2020, 150(12): 3437.

doi: 10.1007/s10562-020-03245-5    
[40]
Yan K, Lafleur T, Jarvis C, Wu G S. J. Clean. Prod., 2014, 72: 230.

doi: 10.1016/j.jclepro.2014.02.056     URL    
[41]
Vu H T, Harth F M, Goepel M, Linares N, García-Martínez J, Gläser R. Chem. Eng. J., 2022, 430: 132763.

doi: 10.1016/j.cej.2021.132763     URL    
[42]
Jiang L, Xu G Y, Fu Y. Green Chem., 2021, 23(18): 7065.

doi: 10.1039/D1GC01732B     URL    
[43]
Balla P, Seelam P K, Balaga R, Rajesh R, Perupogu V, Liang T X. J. Environ. Chem. Eng., 2021, 9(6): 106530.

doi: 10.1016/j.jece.2021.106530     URL    
[44]
Xu H, Hu D, Yi Z X, Wu Z T, Zhang M, Yan K. ACS Appl. Energy Mater., 2019, 2(10): 6979.

doi: 10.1021/acsaem.9b01439     URL    
[45]
Pinto B P, Fortuna A L L, Cardoso C P, Mota C J A. Catal. Lett., 2017, 147(3): 751.

doi: 10.1007/s10562-017-1977-9     URL    
[46]
Popova M, Djinović P, Ristić A, Lazarova H, Dražić G, Pintar A, Balu A M, Novak Tušar N. Front. Chem., 2018, 6: 285.

doi: 10.3389/fchem.2018.00285     URL    
[47]
Hengst K, Schubert M, Carvalho H W P, Lu C B, Kleist W, Grunwaldt J D. Appl. Catal. A Gen., 2015, 502: 18.

doi: 10.1016/j.apcata.2015.05.007     URL    
[48]
Jiang K, Sheng D, Zhang Z H, Fu J, Hou Z Y, Lu X Y. Catal. Today, 2016, 274: 55.

doi: 10.1016/j.cattod.2016.01.056     URL    
[49]
Gundekari S, Srinivasan K. Catal. Lett., 2019, 149(1): 215.

doi: 10.1007/s10562-018-2618-7    
[50]
Shao Y W, Sun K, Fan M J, Wang J Z, Gao G M, Zhang L J, Zhang S, Hu X. Chem. Eng. Sci., 2022, 248: 117258.

doi: 10.1016/j.ces.2021.117258     URL    
[51]
Liang B F, Liu C, Jing F L, Luo S Z. J. Environ. Chem. Eng., 2022, 10(3): 107760.

doi: 10.1016/j.jece.2022.107760     URL    
[52]
Gan L J, Deng C Q, Deng J. Green Chem., 2022, 24(8): 3143.

doi: 10.1039/D2GC00518B     URL    
[53]
Wang D W, Luo M Y, Yue L H, Wei J, Zhang X Y, Cai J J. Fuel, 2022, 329: 125364.

doi: 10.1016/j.fuel.2022.125364     URL    
[54]
Barla M K, Velagala R R, Minpoor S, Madduluri V R, Srinivasu P. J. Hazard. Mater., 2021, 405: 123335.

doi: 10.1016/j.jhazmat.2020.123335     URL    
[55]
Murugesan K, Alshammari A S, Sohail M, Jagadeesh R V. ACS Sustainable Chem. Eng., 2019, 7(17): 14756.

doi: 10.1021/acssuschemeng.9b02692     URL    
[56]
Novodárszki G, Solt H E, Valyon J, LÓnyi F, HancsÓk J, Deka D, Tuba R, Mihályi M R. Catal. Sci. Technol., 2019, 9(9): 2291.

doi: 10.1039/C9CY00168A     URL    
[57]
Shao Y W, Ba S J, Sun K, Gao G M, Fan M J, Wang J Z, Fan H L, Zhang L J, Hu X. Chem. Eng. J., 2022, 429: 132433.

doi: 10.1016/j.cej.2021.132433     URL    
[58]
Li J F, Li M J, Zhang C X, Liu C L, Yang R Z, Dong W S. J. Catal., 2020, 381: 163.

doi: 10.1016/j.jcat.2019.10.031     URL    
[59]
Shao Y W, Sun K, Li Q Y, Liu Q H, Zhang S, Liu Q, Hu G Z, Hu X. Green Chem., 2019, 21(16): 4499.

doi: 10.1039/C9GC01706B     URL    
[60]
Mitta H, Perupogu V, Boddula R, Ginjupalli S R, Inamuddin , Asiri A M. Int. J. Hydrog. Energy, 2020, 45(50): 26445.

doi: 10.1016/j.ijhydene.2019.11.149     URL    
[61]
Zhang R H, Ma Y B, You F, Peng T, He Z C, Li K N. Int. J. Hydrog. Energy, 2017, 42(40): 25185.

doi: 10.1016/j.ijhydene.2017.08.121     URL    
[62]
Zhang J, Chen J Z, Guo Y Y, Chen L M. ACS Sustainable Chem. Eng., 2015, 3(8): 1708.

doi: 10.1021/acssuschemeng.5b00535     URL    
[63]
Raguindin R Q, Desalegn B Z, Gebresillase M N, Seo J G. Renew. Energy, 2022, 191: 763.

doi: 10.1016/j.renene.2022.04.078     URL    
[64]
Xie Z B, Chen B F, Wu H R, Liu M Y, Liu H Z, Zhang J L, Yang G Y, Han B X. Green Chem., 2019, 21(3): 606.

doi: 10.1039/C8GC02914H     URL    
[65]
Li Y F, Lan X C, Liu B Y, Wang T F. J. Ind. Eng. Chem., 2022, 107: 215.

doi: 10.1016/j.jiec.2021.11.048     URL    
[66]
Cai B, Zhang Y J, Feng J F, Huang C, Ma T Y, Pan H. Renew. Energy, 2021, 177: 652.

doi: 10.1016/j.renene.2021.05.159     URL    
[67]
Kuwahara Y, Kaburagi W, Fujitani T. RSC Adv., 2014, 4(86): 45848.

doi: 10.1039/C4RA08074B     URL    
[68]
Chen H, Xu Q, Li H, Liu J, Liu X X, Huang G, Yin D L. Catal. Lett., 2021, 151(2): 538.

doi: 10.1007/s10562-020-03326-5    
[69]
Yu N X, Lu H F, Yang W, Zheng Y X, Hu Q, Liu Y Y, Wu K J, Liang B. Biomass Convers. Biorefinery, 2022,DOI:10.1007/s13399-022-02887-2.
[70]
Yu Z Q, Meng F X, Wang Y, Sun Z C, Liu Y Y, Shi C, Wang W, Wang A J. Ind. Eng. Chem. Res., 2020, 59(16): 7416.

doi: 10.1021/acs.iecr.0c00257     URL    
[71]
Sakakibara K, Endo K, Osawa T. Catal. Commun., 2019, 125: 52.

doi: 10.1016/j.catcom.2019.03.021    
[72]
Gong W B, Chen C, Fan R Y, Zhang H M, Wang G Z, Zhao H J. Fuel, 2018, 231: 165.

doi: 10.1016/j.fuel.2018.05.075     URL    
[73]
Jori P K, Jadhav V H. Catal. Lett., 2020, 150(7): 2038.

doi: 10.1007/s10562-020-03119-w    
[74]
Wang J, Jaenicke S, Chuah G K. RSC Adv., 2014, 4(26): 13481.

doi: 10.1039/C4RA01120A     URL    
[75]
LÓpez-Aguado C, del Monte D M, Paniagua M, Morales G, Melero J A. Ind. Eng. Chem. Res., 2022, 61(16): 5547.

doi: 10.1021/acs.iecr.1c04644     URL    
[76]
Xu S D, Yu D Q, Ye T, Tian P P. RSC Adv., 2017, 7(2): 1026.

doi: 10.1039/C6RA25594A     URL    
[77]
Wan F F, Yang B, Zhu J K, Jiang D B, Zhang H H, Zhang Q, Chen S N, Zhang C, Liu Y C, Fu Z H. Green Chem., 2021, 23(9): 3428.

doi: 10.1039/D1GC00209K     URL    
[78]
Kuwahara Y, Kaburagi W, Osada Y, Fujitani T, Yamashita H. Catal. Today, 2017, 281: 418.

doi: 10.1016/j.cattod.2016.05.016     URL    
[79]
Li H, Fang Z, Yang S. ACS Sustainable Chem. Eng., 2016, 4(1): 236.

doi: 10.1021/acssuschemeng.5b01480     URL    
[80]
Mei C A, Dumesic J A. Chem. Commun., 2011, 47(44): 12233.

doi: 10.1039/c1cc14748j     URL    
[81]
Gu J, Zhang J, Wang Y Z, Li D N, Huang H Y, Yuan H R, Chen Y. Ind. Crops Prod., 2020, 145: 112133.

doi: 10.1016/j.indcrop.2020.112133     URL    
[82]
Wang J Y, Zhang G Y, Liu M Y, Xia Q, Yu X, Zhang W X, Shen J, Yang C H, Jin X. Chem. Eng. Sci., 2020, 222: 115721.

doi: 10.1016/j.ces.2020.115721     URL    
[83]
Yun W C, Yang M T, Lin K Y A. J. Colloid Interface Sci., 2019, 543: 52.

doi: 10.1016/j.jcis.2019.02.036     URL    
[84]
Xiao Z H, Zhou H C, Hao J M, Hong H L, Song Y M, He R X, Zhi K D, Liu Q S. Fuel, 2017, 193: 322.

doi: 10.1016/j.fuel.2016.12.072     URL    
[85]
Kuwahara Y, Kango H, Yamashita H. ACS Sustainable Chem. Eng., 2017, 5(1): 1141.

doi: 10.1021/acssuschemeng.6b02464     URL    
[86]
Li J, Zhao S H, Li Z, Liu D, Chi Y N, Hu C W. Inorg. Chem., 2021, 60(11): 7785.

doi: 10.1021/acs.inorgchem.1c00185     URL    
[87]
Shao Y W, Sun K, Zhang L J, Xu Q, Zhang Z M, Li Q Y, Zhang S, Wang Y, Liu Q, Hu X. Green Chem., 2019, 21(24): 6634.

doi: 10.1039/C9GC03056E     URL    
[88]
Cao J P, Xie T, Zhao X Y, Zhu C, Jiang W, Zhao M, Zhao Y P, Wei X Y. Fuel, 2021, 284: 119027.

doi: 10.1016/j.fuel.2020.119027     URL    
[89]
Osatiashtiani A, Lee A F, Wilson K. J. Chem. Technol. Biotechnol, 2017, 92(6): 1125.
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