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生物质基糠醛和5-羟甲基糠醛加氢转化研究进展

张军 李丹妮 袁浩然 王树荣 陈勇

张军, 李丹妮, 袁浩然, 王树荣, 陈勇. 生物质基糠醛和5-羟甲基糠醛加氢转化研究进展[J]. 燃料化学学报, 2021, 49(12): 1752-1767. doi: 10.1016/S1872-5813(21)60135-4
引用本文: 张军, 李丹妮, 袁浩然, 王树荣, 陈勇. 生物质基糠醛和5-羟甲基糠醛加氢转化研究进展[J]. 燃料化学学报, 2021, 49(12): 1752-1767. doi: 10.1016/S1872-5813(21)60135-4
ZHANG Jun, LI Dan-ni, YUAN Hao-ran, WANG Shu-rong, CHEN Yong. Advances on the catalytic hydrogenation of biomass-derived furfural and 5-hydroxymethylfurfural[J]. Journal of Fuel Chemistry and Technology, 2021, 49(12): 1752-1767. doi: 10.1016/S1872-5813(21)60135-4
Citation: ZHANG Jun, LI Dan-ni, YUAN Hao-ran, WANG Shu-rong, CHEN Yong. Advances on the catalytic hydrogenation of biomass-derived furfural and 5-hydroxymethylfurfural[J]. Journal of Fuel Chemistry and Technology, 2021, 49(12): 1752-1767. doi: 10.1016/S1872-5813(21)60135-4

生物质基糠醛和5-羟甲基糠醛加氢转化研究进展

doi: 10.1016/S1872-5813(21)60135-4
基金项目: 国家自然科学基金面上项目(51976222),南方海洋科学与工程广东省实验室(广州)人才团队引进重大专项(GML2019ZD0101),能源清洁利用国家重点实验室开放基金课题(ZJU-CEU2020023)资助
详细信息
    通讯作者:

    E-mail: yuanhr@ms.giec.ac.cn

  • #共同第一作者
  • 中图分类号: TQ251.1

Advances on the catalytic hydrogenation of biomass-derived furfural and 5-hydroxymethylfurfural

Funds: The project was supported by the National Natural Science Foundation of China (51976222), Key Special Project for Introduced Talents Team of Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou) (GML2019ZD0101), State Key Laboratory of Clean Energy Utilization (Open Fund Project ZJU-CEU2020023)
  • 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。
    1)  #共同第一作者
  • FIG. 1141.  FIG. 1141.

    FIG. 1141.  FIG. 1141.

    图  1  FFR和HMF分子结构式

    Figure  1  Molecular structure of furfural (FFR, left) and 5-hydroxymethylfurfural (HMF, right)

    图  2  FFR典型化学性质和转化路径

    Figure  2  Typical chemical properties and conversion routes of FFR

    图  3  HMF典型化学性质和转化路径

    Figure  3  Typical chemical properties and conversion routes for HMF

    图  4  MgO表面甲醇的可能转化过程[62]

    Figure  4  Possible reactions of methanol on MgO surface[62]

    图  5  Cu/AC-SO3H催化剂上FFR可能加氢途径[34]

    Figure  5  Possible reaction routes for the hydrogenation of FFR on Cu/AC-SO3H catalyst[34]

    (with permission from ACS Publications)

    图  6  ZrO(OH)2催化剂上HMF合成BHMF反应机理

    Figure  6  Reaction mechanism of BHMF synthesis from HMF over the ZrO(OH)2 catalyst

    图  7  CuO-Pd/C催化剂表面FFR转化为FA的反应机理示意图

    Figure  7  Reaction mechanism for the conversion of FFR to FA over the CuO-Pd/C catalyst

    图  8  Pd/ZrP催化剂表面HMF转化为HDO的反应机理示意图[75]

    Figure  8  Reaction mechanism of the conversion of HMF to HDO on Pd/ZrP catalyst[75]

    (with permission from ChemSusChem)

    图  9  PMHS供氢Pd/C催化剂表面FFR转化反应机理示意图[82]

    Figure  9  Reaction mechanism for the conversion of FFR over the Pd/C catalyst using PMHS as hydrogen donor[82]

    (with permission from Springer Nature)

    图  10  FFR转化过程产物计算自由能图[82]

    Figure  10  Computational free energy diagrams of various products during FFR conversion[82]

    表  1  FFR和HMF各项物化性质[24]

    Table  1  Physicochemical properties of furfural (FFR) and 5-hydroxymethylfurfural (HMF)[24]

    ChemicalFurfural (FFR)5-hydroxym ethylfurfural (HMF)
    Molecular formulaC5H4O2C6H6O3
    Molecular weight/(g·mol−1)96.08126.11
    Boiling point/K435387−389
    Melting point/K237301−307
    Density/(g·cm−3)1.161.24
    下载: 导出CSV

    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

    EntryCatalystSubstrateSolventTime /hTemp./KPres./MPaConv./%ProductYield/%Ref.
    1Pt/HTFFRisopropanol44233 > 991,2-PeD73[29]
    2Pt/MCM-41HMFH2O23080.8100BHMF98.9[30]
    3Ru/Al2O3HMF1-butanol-H2O24032.792BHMF74.5[31]
    4Pt/CHMFethanol182961.4BHMF82[32]
    5Pt/Al2O3HMFethanol183331.4BHMF85[32]
    6Pt1Sn1/Al2O3HMFethanol53331.4BHMF82[32]
    7Pt/Co2AlO4FFRethanol244231.51,5-PeD31.9[33]
    8Cu/AC-SO3HFFRisopropanol23784100FA > 99.9[34]
    9Ni/NCNTsFFRH2O73734100THFA100[35]
    10Cu-Fe (1:2)HMFisopropanol4443297DMF90[36]
    11RuSn0. 4/CFFRH2O53631.2595FA94.7[37]
    12Ru(CO)/rGOFFRH2O5293193.3FA91[38]
    13Ni/CNFFRisopropanol4473196FA91[39]
    14Pd/Cu/MgOFFRH2O0.94030.8100FA99[40]
    15Pd-Ir-ReOx/SiO2FFRH2O80313−3736 > 99.91,5-PeD83[41]
    16Rh-Ir-ReOx/SiO2FFRH2O40313−3738 > 99.91,5-PeD71[42]
    17Ir-ReOx/SiO2FFRH2O64030.8>99FA>99[43]
    18Cu∶Zn∶Cr∶Zr(3∶2∶1∶3)FFRisopropanol3.54431100FA96[44]
    19CoAlHMFmethanol4393489.4BHMF83[45]
    20CuZrHMF1-butanol24731.5100DMF60.6[46]
    21Ni(40)/MgO(30)-MFFR1-butanol44134100THFA100[47]
    225Ni-12Cu/SBA-16HMFTHF44832100DMF60.7[48]
    23NiFeMgAlFFRethanol3443499.71,5-PeD31[49]
    下载: 导出CSV

    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

    EntryCatalystSubstrateHydrogen donorTime
    /h
    Temperature
    /K
    Conversion
    /%
    ProductYield
    /%
    Ref.
    1Cu/AC-SO3HFFRisopropanol5423FA > 99.9[34]
    2Cu2AlFFRmethanol2.5473100FA94[16]
    3Cu3Al-AFFRmethanol1.5513100MF94.1[16]
    4MgOHMFmethanol3433100BHMF100[58]
    5Fe-L1/C-800FFR2-butanol1543391.6FA76[59]
    6ZrO(OH)2HMFethanol2.542394.1BHMF83.7[60]
    7Ru/NiFe2O4FFRisopropanol6453 > 97MF83[61]
    8Mg/Fe/OFFRmethanol165393MF83[62]
    9Cu-PMOHMFmethanol3533100DMF48[63]
    10Zr-LSFFR2-propanol137392.2FA91.6[55]
    11Zr1Fe1-150FFR2-propanol2453100FA99.1[64]
    12Ru/RuO2/CFFR2-butanol10453MF76[66]
    13MZH(Zr/Fe = 2)HMF2-butanol542398.4BHMF89.6[66]
    14Ru/RuO2/CFFR2-pentanol10453MF76[65]
    15Co3O4@MCHMFisopropanol12413100BHMF97[67]
    16Ru/Co3O4HMFisopropanol6463100BHMF82.8[68]
    17Pd/Fe2O3FFRisopropanol7.545387FA57[69]
    18Au/ZrO2FFRisopropanol3393100FA100[70]
    19Ni-SAs/NCFFRisopropanol340385.1FA82.6[71]
    20Zr@Co-2FFRisopropanol443393.9FA91.4[72]
    下载: 导出CSV

    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

    EntryCatalystSubstrateTime
    /h
    Temperature
    /K
    Conversion
    /%
    ProductYield
    /%
    Ref.
    1Cu/MgAl2O4HMF148390FA89[76]
    2CuO-Pd/CFFR3443100FA98.1[74]
    348NiHMF5493100DMF58.8[77]
    4Pd/ZrPHMF2141397HDO43[75]
    下载: 导出CSV

    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

    EntryCatalystHydrogen donorSubstrateTime
    /h
    Temperature
    /K
    Conversion
    /%
    ProductYield
    /%
    Ref.
    1 Pd/C-wet PMHS FFR 12 288 99 FA 95 [82]
    2 Pd/MIL-53(Al)-P PMHS HMF 2.5 298 100 DMF 99 [83]
    3 Pd/MIL-53(Al)-P PMHS FFR 2 298 100 MF 97 [83]
    4 PdCl2 PMHS HMF 0.5 298 100 DMF 89.7 [84]
    下载: 导出CSV
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  • 收稿日期:  2021-06-02
  • 修回日期:  2021-07-03
  • 网络出版日期:  2021-08-10
  • 刊出日期:  2021-12-29

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