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甘油缩合制丙酮缩甘油中催化剂及反应机理研究进展

曾祥棵 王玮璐 黎良菊 欧阳平 张贤明

曾祥棵, 王玮璐, 黎良菊, 欧阳平, 张贤明. 甘油缩合制丙酮缩甘油中催化剂及反应机理研究进展[J]. 燃料化学学报. doi: 10.19906/j.cnki.JFCT.2021063
引用本文: 曾祥棵, 王玮璐, 黎良菊, 欧阳平, 张贤明. 甘油缩合制丙酮缩甘油中催化剂及反应机理研究进展[J]. 燃料化学学报. doi: 10.19906/j.cnki.JFCT.2021063
ZENG Xiang-ke, WANG Wei-lu, LI Liang-ju, OU-YANG Ping, ZHANG Xian-ming. Research progress of catalysts and reaction mechanism in glycerol condensation to acetone glycidol[J]. Journal of Fuel Chemistry and Technology. doi: 10.19906/j.cnki.JFCT.2021063
Citation: ZENG Xiang-ke, WANG Wei-lu, LI Liang-ju, OU-YANG Ping, ZHANG Xian-ming. Research progress of catalysts and reaction mechanism in glycerol condensation to acetone glycidol[J]. Journal of Fuel Chemistry and Technology. doi: 10.19906/j.cnki.JFCT.2021063

甘油缩合制丙酮缩甘油中催化剂及反应机理研究进展

doi: 10.19906/j.cnki.JFCT.2021063
基金项目: 重庆市教育委员会科学技术研究项目(KJQ202000823)资助
详细信息
    通讯作者:

    E-mail: weiluwang@ctbu.edu.cn

  • 中图分类号: TQ 251.1

Research progress of catalysts and reaction mechanism in glycerol condensation to acetone glycidol

  • 摘要: 随着生物柴油产业的蓬勃发展,其主要副产物甘油的资源化利用已亟不可待。其中,将甘油与丙酮缩合生成丙酮缩甘油(2, 2-二甲基-1, 3-二氧戊环-4-甲醇,Solketal)是极具前景的研究方向,因为Solketal作为燃料添加剂不仅能显著增强燃油的黏度和低温性能,还能显著地减少一氧化碳、固体小颗粒及其他环境不友好物质的排放。该反应需依赖于催化剂中酸性位点的催化作用,所以酸催化剂的结构形态、酸量及相关理化性质的设计及完善是制约甘油缩酮化反应工业化进程的关键。因此,本文结合近年来相关文献,系统综述了在该反应中均相、非均相酸催化剂在该领域中的研究进展及相关反应机理讨论。笔者首先从结构形态角度进行分类,介绍了不同类型酸催化剂的优势及特色,并在其结构性质对催化活性的影响上进行了重点阐述。最后,对该领域中催化剂未来研究方向进行了展望。
  • 图  1  生物柴油中甘油副产物的来源[6]

    Figure  1  Sources of glycerol by-products in biodiesel[6]

    图  2  甘油与丙酮的缩合反应[21]

    Figure  2  Condensation between glycerol and acetone[21]

    图  3  SnCl2催化丙酮缩甘油的合成[34]

    Figure  3  SnCl2-catalyzed solketal synthesis[34]

    图  4  Fe3+在甘油缩酮化反应中的反应机理[37]

    Figure  4  Reaction mechanism of Fe3+ in the ketalization of glycerol[37]

    图  5  甘油与丙酮在Lewis酸中心缩酮反应机理[64]

    Figure  5  Ketalization reaction mechanism of glycerol with acetone in L-acid Center[64]

    图  6  甘油与丙酮在Brønsted酸中心缩酮反应机理[49]

    Figure  6  Ketalization reaction mechanism of glycerol with acetone in B-acid Center[49]

    表  1  均相催化剂在甘油缩酮化反应中的反应及相关反应参数

    Table  1  Reaction results and related parameters of homogeneous catalysts in the ketalization of glycerol

    Homogeneous catalystMolar ratio of raw materials (acetone:glycerol)Reaction conditionsConversion of glycerin /%Selectivity of solketal /%Ref.
    SnCl2nn = 4∶125 ℃, 2 h, CH3CN as solvent9598[34]
    SnF2nn = 8∶125 ℃, 2 h9094[35]
    FeCl3(1-R)nn = 4∶1room temperature, 1.5 h90[36]
    Fe(NO3)3·9H2Onn = 1∶20room temperature, 100 min9697[37]
    Tetrapropylammonium phosphotungstatenn = 6∶130 ℃, 3 h94[38]
    下载: 导出CSV

    表  2  负载型催化剂在甘油缩酮化反应中的反应及相关反应参数

    Table  2  Reaction results and related parameters of the supported catalyst in the ketalization of glycerol

    Supported catalystMolar ratio of raw materials (acetone:glycerol)Reaction conditionsConversion of glycerin /%Selectivity of solketal /%Ref.
    Al2O3 loading${\rm{SO}}_{4}^{{2 -} } $/Zr2O-Al2O3nn = 3∶160 ℃, 100 min9694[41]
    SiO2 loadingZr-TUD-1, Hf-TUD-1,
    Sn-MCM-41
    nn = 1∶170 ℃, 6 h64, 65 and 62, respectively[43]
    Carbon-based loadingSO3H-Cnn = 8∶157 ℃, 1 h80100[44]
    5%Ni-1%Zr/ACnn = 8∶145 ℃, 3 h76[45]
    Ni-MWCNTs
    (multi-walled carbon nanotubes)
    nn = 6∶140 ℃, 3 h96[45]
    下载: 导出CSV

    表  3  分子筛催化剂在甘油缩酮化反应中的反应及相关反应参数

    Table  3  Reaction results and related parameters of molecular sieve catalyst in the ketalization of glycerol

    Molecular sieve catalystMolar ratio of raw materials (acetone:glycerol)Reaction conditionsConversion of glycerin /%Selectivity of solketal /%Ref.
    Sulfo-functionalized SiO2Pr-SBA-15
    Ar-SBA-15
    nn = 6∶170 ℃, 30 min79, 82.5, respectively[46]
    Sulfo-functionalized polymersMP-SO3H-24nn = 5∶1room temperature, 30 min9498.5[47]
    Mesoporous titanium phosphateM-TiPO-Xnn = 8∶150 ℃, 4 h91.394.7[48]
    Mesoporous foam materialsCS-MCFnn = 2∶140 ℃, 180 min8799[49]
    Modified metal oxidesMo(VI)/ ZrO2nn = 6∶160 ℃, 8 min9898[50]
    M-NiAlPO4nn = 8∶180 ℃, 1 h75.4475.12[51]
    ZeoliteH-Beta-1nn = 2∶1room temperature, 2 h8698.5[52]
    dealuminated BEA Zeolitenn = 1∶130 ℃, 30 min80100[53]
    下载: 导出CSV

    表  4  黏土催化剂在甘油缩酮化反应中的反应及相关反应参数

    Table  4  Reaction results and related parameters of clay catalyst in the ketalization of glycerol

    Clay catalystMolar ratio of raw materials (acetone:glycerol)Reaction conditionsConversion of glycerin /%Selectivity of solketal /%Ref.
    Montmorillonite/clayHNO3 modified montmorillonitenn = 4∶125 ℃, 10 min9495.4[58]
    K10 montmorillonitenn = 6∶130 ℃, 2 h8785[59]
    K10 montmorillonitenn = 6∶140 ℃, p=600 psi, WHSV=4 h−169[60]
    下载: 导出CSV

    表  5  阳离子交换树脂在甘油缩酮化反应中的反应及相关反应参数

    Table  5  Reaction results and related parameters of cation exchange resin in the ketalization of glycerol

    Cation exchange resin catalystMolar ratio of
    raw materials
    (acetone:glycerol)
    Reaction conditionsConversion of glycerin /%Selectivity of solketal /%Ref.
    Cation exchange resinpurolite®PD206nn = 5∶120 ℃, p = 12 MPa, 0.1 mL/min−1 acetone feed95100[62]
    Amberlyst-15nn = 3∶160 ℃, 3 h87.41[63]
    Amberlyst-35nn = 2∶125-45 ℃, CH3CH2OH as solvent74[64]
    Amberlyst-46nn = 6∶160 ℃, 30 min8497[7]
    DT-851nn = 20∶158 ℃, 2 h9599[65]
    KU-2-8nn = 5∶135 ℃, CH3CH2OH as solvent83.7[66]
    下载: 导出CSV

    表  6  其他类型催化剂在甘油缩酮化反应中的反应及相关反应参数

    Table  6  Reaction results and related parameters of other types of catalysts in the ketalization of glycerol

    Other catalystsMolar ratio of raw materials (acetone:glycerol)Reaction conditionsConversion of glycerin /%Selectivity of solketal /%Ref.
    Other types of catalystsSnO2, MoO3/SnO2, WO3/SnO2nn = 1∶1room temperature, 90 min15, 55 and 61, respectively96[2]
    V-MCM-41nn = 6.5∶160 ℃, 1 h9080[42]
    Ionic liquidsnn = 15∶1room temperature, 30 min, 0.2 mol% of BAIL10098[67]
    Pressurized CO2nn = 2∶1118 ℃, 5 h; p = 4.22 MPa61[68]
    Heteropoly acid saltnn = 12∶1room temperature, 1 h9997[33]
    下载: 导出CSV
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  • 收稿日期:  2021-04-12
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