Research progress of catalysts and reaction mechanism in glycerol condensation to acetone glycidol
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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,本研究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。对该领域中催化剂未来研究方向进行了展望。Abstract: With the booming of biodiesel industry, it is urgent to high-valued to recycle glycerol as the main by-product. The condensation of glycerol (GLY) with acetone to produce acetone glycidol (2, 2-dimethyl-1, 3-dioxolane-4-methanol, Solketal) is promising direction for GLY utilization, because Solketal can function as fuel additive to modify the fuel viscosity and low-temperature performance of oil significantly, and reduce the emission of carbon monoxide, small solid particles and other environmentally unfriendly substances further. However, the reaction needs to be accelerated by the catalyst with acid nature, thus the design and modification over the structure and acid properties of catalysts are dominating the process of glycerol ketonization reaction. So, this paper systematically reviews the progress of homogeneous and heterogeneous acid catalysts, and the reaction mechanism in recent years. It is classified based on the structural properties, advantages and characteristics of different catalysts, and influences of their structural properties on catalytic activity. Finally, some future directions for this research field are pointed out.
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Key words:
- biodiesel /
- glycerol ketalization /
- catalyst /
- reaction mechanism
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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 catalyst Molar ratio of raw materials (acetone:glycerol) Reaction conditions Conversion of glycerin /% Selectivity of solketal /% Ref. SnCl2 n∶n = 4∶1 25 ℃, 2 h, CH3CN as solvent 95 98 [34] SnF2 n∶n = 8∶1 25 ℃, 2 h 90 94 [35] FeCl3(1-R) n∶n = 4∶1 room temperature, 1.5 h 90 − [36] Fe(NO3)3·9H2O n∶n = 1∶20 room temperature, 100 min 96 97 [37] Tetrapropylammonium phosphotungstate n∶n = 6∶1 30 ℃, 3 h 94 − [38] 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 catalyst Molar ratio of raw materials (acetone:glycerol) Reaction conditions Conversion of glycerin /% Selectivity of solketal /% Ref. Carbon-based loading SO3H-C n∶n = 8∶1 57 ℃, 1 h 80 100 [42] SiO2 loading Zr-TUD-1, Hf-TUD-1,
Sn-MCM-41n∶n = 1∶1 70 ℃, 6 h 64, 65 and 62, respectively − [43] Al2O3 loading ${\rm{SO}}_{4}^{{2 -} } $/Zr2O-Al2O3 n∶n = 3∶1 60 ℃, 100 min 96 94 [44] 5%Ni-1%Zr/AC n∶n = 8∶1 45 ℃, 3 h 76 − [45] Ni-MWCNTs
(multi-walled carbon nanotubes)n∶n = 6∶1 40 ℃, 3 h 96 − [45] 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 catalyst Molar ratio of raw materials (acetone:glycerol) Reaction conditions Conversion of glycerin /% Selectivity of solketal /% Ref. Sulfo-functionalized SiO2 Pr-SBA-15
Ar-SBA-15n∶n = 6∶1 70 ℃, 30 min 79, 82.5, respectively − [46] Sulfo-functionalized polymers MP-SO3H-24 n∶n = 5∶1 room temperature, 30 min 94 98.5 [47] Mesoporous titanium phosphate M-TiPO-X n∶n = 8∶1 50 ℃, 4 h 91.3 94.7 [48] Mesoporous foam materials CS-MCF n∶n = 2∶1 40 ℃, 180 min 87 99 [49] Modified metal oxides Mo(VI)/ ZrO2 n∶n = 6∶1 60 ℃, 8 min 98 98 [50] M-NiAlPO4 n∶n = 8∶1 80 ℃, 1 h 75.44 75.12 [51] Zeolite H-Beta-1 n∶n = 2∶1 room temperature, 2 h 86 98.5 [52] dealuminated BEA Zeolite n∶n = 1∶1 30 ℃, 30 min 80 100 [53] 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 catalyst Molar ratio of raw materials (acetone:glycerol) Reaction conditions Conversion of glycerin /% Selectivity of solketal /% Ref. Montmorillonite/clay HNO3 modified montmorillonite n∶n = 4∶1 25 ℃, 10 min 94 95.4 [58] K10 montmorillonite n∶n = 6∶1 40 ℃, p=600 psi, WHSV=4 h−1 69 − [59] K10 montmorillonite n∶n = 6∶1 30 ℃, 2 h 87 85 [61] 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 catalyst Molar ratio of
raw materials
(acetone:glycerol)Reaction conditions Conversion of
glycerin /%Selectivity of
solketal /%Ref. Cation exchange
resinAmberlyst-46 n∶n = 6∶1 60 ℃, 30 min 84 97 [7] purolite®PD206 n∶n = 5∶1 20 ℃, p = 12 MPa, 0.1 mL/min acetone feed 95 100 [62] KU-2-8 n∶n = 5∶1 35 ℃, CH3CH2OH as solvent 83.7 − [63] Amberlyst-15 n∶n = 3∶1 60 ℃, 3 h 87.41 − [64] DT-851 n∶n = 20∶1 58 ℃, 2 h 95 99 [65] Amberlyst-35 n∶n = 2∶1 25−45 ℃, CH3CH2OH as solvent 74 − [66] 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 catalyst Molar ratio of raw materials (acetone: glycerol) Reaction conditions Conversion of glycerin /% Selectivity of solketal /% Ref. Other types of catalysts SnO2, MoO3/SnO2, WO3/SnO2 n∶n = 1∶1 room temperature, 90 min 15, 55 and 61, respectively 96 [2] Heteropoly acid salt n∶n = 12∶1 room temperature, 1 h 99 97 [33] V-MCM-41 n∶n = 6.5∶1 60 ℃, 1 h 90 80 [42] Ionic liquids n∶n = 15∶1 room temperature, 30 min,
0.2 mol% of BAIL100 98 [67] Pressurized CO2 n∶n = 2∶1 118 ℃, 5 h; p = 4.22 MPa 61 − [68] -
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