Advances on the catalytic hydrogenation of biomass-derived furfural and 5-hydroxymethylfurfural
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摘要: 近年来,利用生物质基平台化合物转化制备各种燃料及高值化学品引起研究人员的广泛关注。5-羟甲基糠醛(HMF)和糠醛(FFR)作为一类重要的生物质衍生平台化合物,分子结构中醛基和呋喃环等官能团赋予其独特的化学性质。本综述针对HMF和FFR在氢气、低碳醇、甲酸和硅烷等不同氢源中的催化加氢反应研究现状进行了阐述,对加氢转化过程中的主要影响因素如催化剂类型和反应条件以及反应机理等进行了详细分析,同时对HMF/FFR加氢转化应用研究前景进行了展望。Abstract: In recent years, the conversion of biomass-derived platform compounds into a variety of high value fuel and chemical products has attracted increasing attention from researchers. 5-Hydroxymethylfurfural (HMF) and furfural (FFR) belong to a class of important biomass-derived platform chemicals. The molecular structure of HMF and FFR is consisted of aldehyde group, furan ring and other functional groups, which endow them with unique chemical properties. In this paper, the research advances on the catalytic hydrogenation of HMF and FFR using various hydrogen sources, such as hydrogen, alcohol, silanes and formic acid, have been reviewed in detail. In addition, the main influencing factors like catalyst type and reaction conditions on the hydrogenation process as well as the reaction mechanism are discussed in depth. Meanwhile, research foreground in the catalytic hydrogenation of HMF/FFR has been prospected.
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Key words:
- biomass /
- catalytic hydrogenation /
- 5-hydroxymethylfurfural /
- furfural
1) #共同第一作者 -
表 1 FFR和HMF各项物化性质[24]
Table 1 Physicochemical properties of furfural (FFR) and 5-hydroxymethylfurfural (HMF)[24]
Chemical Furfural (FFR) 5-hydroxym ethylfurfural (HMF) Molecular formula C5H4O2 C6H6O3 Molecular weight/(g·mol−1) 96.08 126.11 Boiling point/K 435 387−389 Melting point/K 237 301−307 Density/(g·cm−3) 1.16 1.24 表 2 分子H2作为氢源催化FFR和HMF加氢转化
Table 2 Hydrogenation of FFR and HMF using molecular H2 as hydrogen source
Entry Catalyst Substrate Solvent Time /h Temp./K Pres./MPa Conv./% Product Yield/% Ref. 1 Pt/HT FFR isopropanol 4 423 3 > 99 1,2-PeD 73 [29] 2 Pt/MCM-41 HMF H2O 2 308 0.8 100 BHMF 98.9 [30] 3 Ru/Al2O3 HMF 1-butanol-H2O 2 403 2.7 92 BHMF 74.5 [31] 4 Pt/C HMF ethanol 18 296 1.4 − BHMF 82 [32] 5 Pt/Al2O3 HMF ethanol 18 333 1.4 − BHMF 85 [32] 6 Pt1Sn1/Al2O3 HMF ethanol 5 333 1.4 − BHMF 82 [32] 7 Pt/Co2AlO4 FFR ethanol 24 423 1.5 − 1,5-PeD 31.9 [33] 8 Cu/AC-SO3H FFR isopropanol 2 378 4 100 FA > 99.9 [34] 9 Ni/NCNTs FFR H2O 7 373 4 100 THFA 100 [35] 10 Cu-Fe (1:2) HMF isopropanol 4 443 2 97 DMF 90 [36] 11 RuSn0. 4/C FFR H2O 5 363 1.25 95 FA 94.7 [37] 12 Ru(CO)/rGO FFR H2O 5 293 1 93.3 FA 91 [38] 13 Ni/CN FFR isopropanol 4 473 1 96 FA 91 [39] 14 Pd/Cu/MgO FFR H2O 0.9 403 0.8 100 FA 99 [40] 15 Pd-Ir-ReOx/SiO2 FFR H2O 80 313−373 6 > 99.9 1,5-PeD 83 [41] 16 Rh-Ir-ReOx/SiO2 FFR H2O 40 313−373 8 > 99.9 1,5-PeD 71 [42] 17 Ir-ReOx/SiO2 FFR H2O 6 403 0.8 >99 FA >99 [43] 18 Cu∶Zn∶Cr∶Zr(3∶2∶1∶3) FFR isopropanol 3.5 443 1 100 FA 96 [44] 19 CoAl HMF methanol 4 393 4 89.4 BHMF 83 [45] 20 CuZr HMF 1-butanol 2 473 1.5 100 DMF 60.6 [46] 21 Ni(40)/MgO(30)-M FFR 1-butanol 4 413 4 100 THFA 100 [47] 22 5Ni-12Cu/SBA-16 HMF THF 4 483 2 100 DMF 60.7 [48] 23 NiFeMgAl FFR ethanol 3 443 4 99.7 1,5-PeD 31 [49] 表 3 FFR、HMF加氢反应汇总(醇作氢供体)
Table 3 Hydrogenation of FFR and HMF over various catalysts using alcohol as hydrogen donor
Entry Catalyst Substrate Hydrogen donor Time
/hTemperature
/KConversion
/%Product Yield
/%Ref. 1 Cu/AC-SO3H FFR isopropanol 5 423 − FA > 99.9 [34] 2 Cu2Al FFR methanol 2.5 473 100 FA 94 [16] 3 Cu3Al-A FFR methanol 1.5 513 100 MF 94.1 [16] 4 MgO HMF methanol 3 433 100 BHMF 100 [58] 5 Fe-L1/C-800 FFR 2-butanol 15 433 91.6 FA 76 [59] 6 ZrO(OH)2 HMF ethanol 2.5 423 94.1 BHMF 83.7 [60] 7 Ru/NiFe2O4 FFR isopropanol 6 453 > 97 MF 83 [61] 8 Mg/Fe/O FFR methanol 1 653 93 MF 83 [62] 9 Cu-PMO HMF methanol 3 533 100 DMF 48 [63] 10 Zr-LS FFR 2-propanol 1 373 92.2 FA 91.6 [55] 11 Zr1Fe1-150 FFR 2-propanol 2 453 100 FA 99.1 [64] 12 Ru/RuO2/C FFR 2-butanol 10 453 − MF 76 [66] 13 MZH(Zr/Fe = 2) HMF 2-butanol 5 423 98.4 BHMF 89.6 [66] 14 Ru/RuO2/C FFR 2-pentanol 10 453 − MF 76 [65] 15 Co3O4@MC HMF isopropanol 12 413 100 BHMF 97 [67] 16 Ru/Co3O4 HMF isopropanol 6 463 100 BHMF 82.8 [68] 17 Pd/Fe2O3 FFR isopropanol 7.5 453 87 FA 57 [69] 18 Au/ZrO2 FFR isopropanol 3 393 100 FA 100 [70] 19 Ni-SAs/NC FFR isopropanol 3 403 85.1 FA 82.6 [71] 20 Zr@Co-2 FFR isopropanol 4 433 93.9 FA 91.4 [72] 表 4 FFR、HMF加氢反应(甲酸作氢供体)
Table 4 Hydrogenation of FFR and HMF using formic acid as hydrogen donor
表 5 FFR、HMF加氢反应(硅烷作氢供体)
Table 5 Hydrogenation of FFR and HMF with silanes as hydrogen donor
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