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化学进展 2021, Vol. 33 Issue (10): 1856-1873 DOI: 10.7536/PC200852 前一篇   后一篇

• 综述 •

葡萄糖制备5-羟甲基糠醛的溶剂体系及转化机理

尹钰, 马春慧, 李伟, 刘守新*()   

  1. 东北林业大学 生物质材料科学与技术教育部重点实验室 哈尔滨 150040
  • 收稿日期:2020-08-24 修回日期:2020-11-26 出版日期:2021-10-20 发布日期:2020-12-28
  • 通讯作者: 刘守新
  • 基金资助:
    中央高校基本科研基金(2572017ET02); 国家自然科学基金重大项目(31890773)
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Solvent System and Conversion Mechanism of 5-Hydroxymethylfurfural Preparation from Glucose

Yu Yin, Chunhui Ma, Wei Li, Shouxin Liu()   

  1. Key Laboratory of Bio-based Material Science & Technology, Northeast Forestry University,Harbin 150040,China
  • Received:2020-08-24 Revised:2020-11-26 Online:2021-10-20 Published:2020-12-28
  • Contact: Shouxin Liu
  • Supported by:
    Fundamental Research Funds for the Central Universities(2572017ET02); National Natural Science Foundation of China(31890773)

五羟甲基糠醛(5-HMF)被认为是近年来最具发展性和潜力的新型平台化合物。纤维素水解经由葡萄糖中间步骤进而转化为5-HMF是生物质资源制备能源平台化合物的主要利用途径之一,理解葡萄糖转化为5-HMF的过程具有重要意义。本文介绍了由葡萄糖制备5-HMF过程中的不同溶剂体系及外场对目标产物得率的影响,综述了由葡萄糖向5-HMF的转化机理,包括葡萄糖异构为果糖、果糖脱水生成5-HMF。目前,葡萄糖制备5-HMF的溶剂体系包括单相体系、离子液体、双相体系和低共熔溶剂体系,其中由离子液体和有机溶剂构成的双相反应体系是葡萄糖转化制5-HMF最有优势的反应体系,可以使生成的5-HMF迅速从反应相转移到有机相,减少副反应从而提高5-HMF得率;超声振荡、微波辐射和外加压力场通过与反应溶剂的协同作用加速传质、传热,大大缩短反应时间,提高反应效率。目前关于提高5-HMF得率以及中间产物的稳定和控制有待进一步深入研究。

关键词： 葡萄糖, 5-羟甲基糠醛, 溶剂体系, 微波场

5-Hydroxymethylfurfural(5-HMF) is regarded as the most developing and potential platform in recent years. The hydrolysis of cellulose to glucose and then to5-HMFis the key steps in the use of biomass resources to produce green platform compounds. Understanding the catalytic conversion process from glucose to5-HMFis of great significance for improving the potential utilization of biomass resource. Solvent systems and outfield coordination used for the preparation of5-HMFfrom glucose was introduced in this work, focusing on the mechanism of the conversion from glucose to5-HMFincluding the isomerization of glucose to fructose and the dehydration of fructose to 5-HMF. Single-phase solvents, ionic liquids, biphasic solvents and deep eutectic solvent was used in5-HMFproduction. The biphasic solvents system composed of ionic liquid and organic solvent is the most effective reaction solvent system, which can quickly transfer the5-HMFto the organic phase, reduce side reactions and increase the yield of 5-HMF. Outfield coordination of ultrasound vibration, microwave radiation and pressure field accelerate mass transfer and heat transfer, greatly shorten the reaction time and improve the reaction efficiency through the synergistic reaction with the reaction solvent. The improvement of5-HMFyield and the stability of intermediates require further research.

Contents

1 Introduction

2 Solvent systems

2.1 Single-phase solvent

2.2 Ionic liquids

2.3 Biphasic systems

2.4 Deep eutectic solvents

3 Outfield assistance

3.1 Ultrasound vibration

3.2 Microwave radiation

3.3 Pressure field

4 Mechanism of 5-HMF formation

5 Conclusions

Key words: glucose, 5-hydroxymethylfurfural, solvent systems, microwave field
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图1 高附加值5-HMF衍生物[16]
Fig. 1 High value-added chemicals derived from 5-HMF[16]
表1 水溶剂中葡萄糖转化制备5-HMF
Table 1 Conversion of glucose into5-HMF in aqueous solution
Entry Catalyst Solvent Temperature( ℃) Time(min) 5-HMF yield(%) ref
1 - H2O 195 80 28
2 CrCl3·6H2O H2O 130 120 13 29
3 AlCl3 H2O 130 300 11 29
4 FeCl3·6H2O H2O 130 360 1 29
5 H3PO4 HCW 220 5 20 30
6 H3PO4 HCW 200 5 4 30
7 NaOH HCW 200 5 4 30
8 CaP2O6 HCW 220 5 20 30
9 α-Sr(PO3)2 HCW 220 5 21 30
10 C16H3PW11Cr H2O 300 120 35.2 31
11 Nb2O5·nH2O H2O 120 180 12.1 32
12 H3PO4/Nb2O5·nH2O H2O 120 180 52.1 32
13 Fe/HY Zeolite H2O 120 240 11.4 33
图2 葡萄糖脱水制备5-HMF反应的中间产物
Fig. 2 The reaction intermediates for the dehydration of glucose to 5-HMF
表2 有机溶剂中葡萄糖转化制备5-HMF
Table 2 Conversion of glucose into 5-HMF in organic solvents
Entry Catalyst Solvent Temperature( ℃) Time(min) 5-HMF yield(%) ref
1 CrCl3·6H2O DMSO 130 480 54.43 29
2 SnCl4+TBAB DMSO 100 120 69.1 57
3 SnCl4+TBAB DMAC 100 120 50.2 57
4 SnCl4+TBAB DMF 100 120 42.1 57
5 SnCl4+TBAB NMP 100 120 23.8 57
6 Al2O3-B2O3 DMSO 140 120 41.4 59
7 C-SO3H DMSO 130 480 10.10 64
8 β-cyclodextrin-SO3H DMSO 180 300 47 65
9 SPFR H2O/γ-GVL 190 30 33 66
10 Al-SPFR H2O /γ-GVL 170 120 47.4 67
11 SiO2-ATS-PTA Acetone/ H2O 160 140 78.31 68
12 AlCl3 Ethanol/H2O 160 15 70 69
13 CeO2-2SZ@SBA-15 iPrOH/DMSO 120 360 66.5 70
表3 离子液体中葡萄糖转化制备5-HMF
Table 3 Conversion of glucose into 5-HMF in ionic liquids
Entry Catalyst Solvent Temperature( ℃) Time(min) 5-HMF yield(%) ref
1 - [EMIM]Cl 180 180 3 75
2 CrCl2 [EMIM]Cl 100 180 70 75
3 GeCl4 [BMIM]Cl 100 75 38.4 76
4 GeCl4 [DMIM]Br 100 75 23.3 76
5 (Cr0-NP)Cr(CO)6 [EMIM]Cl 120 180 50 77
6 CrCl2 [C10(EPy)2]2Br- 110 120 47 78
7 Cr3+-D001-CC [BMIM]Cl 110 30 61.3 79
8 Cr-montmorillonite [BMIM]Cl 140 20 45 80
9 Cr-bentonite [BMIM]Cl 150 10 62.6 80
10 Cr-USY [BMIM]Cl 130 60 54.5 81
11 Cr-β-zeolite [BMIM]Cl 130 60 58.8 81
12 SnPO [EMIM]Br 120 180 58.3 82
13 Al2O3-b-0.05 [EMIM]Cl 120 180 34.5 83
14 - [C16MIM] Cl 120 12 31 86
15 CrCl3·6H2O Bu-DBUCl 100 180 64 87
16 CrCl3 Et-DBUBS 100 180 78.6 88
17 - [SMIM][FeCl4] 110 300 24 93
18 - [GLY(mim)3][OMs]3 110 180 16 21
19 CC-SO3H [GLY(mim)3][Cl]3 140 300 58 21
图3 Cr0-NP转化葡萄糖为5-HMF示意图
Fig. 3 General scheme for the conversion of glucose into 5-HMF by Cr0-NP
图4 [BMIM]Cl中[C4SO3Hmim]Cl催化转化葡萄糖为5-HMF
Fig.4 Catalytic conversion of glucose into 5-HMF by [C4SO3Hmim]Cl in [BMIM]Cl
图5 双相反应体系中葡萄糖制备5-HMF示意图
Fig. 5 The schematic diagram of 5-HMF production from glucose in biphasic solvent
表4 双相体系中葡萄糖转化制备5-HMF
Table 4 Conversion of glucose into 5-HMF in Biphasic systems
Entry Catalyst Solvent Temperature( ℃) Time(min) 5-HMF yield(%) ref
1 Sn-Beta H2O/THF/NaCl 180 80 - 100
2 SO3H-OAC THF/H2O-NaCl 160 180 93 101
3 [MimAM]HnPW12O40 THF/H2O-NaCl 160 7.5h 53.9 102
4 PCP(Cr)-SO3H·Cr(Ⅲ) THF/H2O-NaCl 180 240 80.7 103
5 ZSM-5/HT-hydr THF/H2O-NaCll 150 120 67 104
6 ZSM-5/HT-dg THF/H2O-NaCl 150 120 64 104
7 HFO(PO4)2.0 THF/H2O-NaCl 175 150 90.5 105
8 B-Cl/AlCl3·6H2O H2O/MIBK 170 30 64 106
7 B-Cl/SnCl4·5H2O H2O/MIBK 170 30 25 106
8 2-SZ-20-HM-550 NaCl/H2O/GVL 195 90 90 107
9 1Nb-MMT-900 MIBK/H2O 170 180 70.52 108
10 AlCl3/ HCl sec-butyl phenol/H2O-NaCl 170 40 62 109
11 AlCl3/ HCl GVL/H2O-NaCl 170 40 94 110
12 AlCl3/ HCl GHL/H2O-NaCl 170 40 92 110
13 AlCl3/ HCl GOL/H2O-NaCl 170 40 92 110
14 AlCl3/ HCl GUL/H2O-NaCl 170 40 83 110
15 CrCl2 P[BVIM]Cl/DMF 120 180 65.8 111
16 P[BVIM]Cl-Et2AlCl P[BVIM]Cl-Et2AlCl/DMF 120 180 49 111
17 Zr(O)Cl2 [BMIM]Cl/MIBK 120 5 66 112
18 SnCl4 [BMIM]Br/GDE 100 120 58.7 113
19 SnCl4 [BMIM]Br/DMC 100 120 64.2 113
20 AlCl3 [BMIM]Cl/EtOH 80 10 11.9 113
图6 Sn-Beta一锅法由葡萄糖制备5-HMF
Fig. 6 “One-pot” synthesis of 5-HMF from glucose using Sn-Beta
图7 双相溶剂在反应中的应用[107]
Fig. 7 Biphasic solvent applied in the reaction[107]
表5 低共熔溶剂体系中葡萄糖转化制备5-HMF
Table 5 Conversion of glucose into 5-HMF in Deep eutectic solvents
Entry Catalyst Solvent Temperature( ℃) Time(min) 5-HMF yield(%) ref
1 B(OH)3 ChDC/SA 140 120 26 116
2 B(OH)3 ChDC/Mandelic acid 140 120 28 116
3 B(OH)3 ChDC/Malic acid 140 120 35 116
4 B(OH)3 ChDC/GA 140 120 42 116
5 B(OH)3 ChDC/GA/H2O 140 240 60 116
6 Extremely low HCl fructose/ChCl 150 30 3.1 117
7 CrCl3 fructose/ChCl 150 30 60.3 117
8 Amberlyst-15 ChCl/MeCN 130 120 12.1 117
9 Amberlyst-15-AlCl3 ChCl/MeCN 130 120 17 118
10 Amberlyst-15-CrCl3 ChCl/MeCN 130 120 57 118
11 Cr-D41 H2O/MIBK/ChCl 195 60 44 119
12 Zr-D41 H2O/MIBK/ChCl 195 60 34 119
13 Al-41 H2O/MIBK/ChCl 195 60 52 119
图8 在DES中合成M-D41催化剂并用于碳水化合物高效脱水制备5-HMF流程示意图[119]
Fig.8 Synthesis of M-D41 in DES for the efficient dehydration of carbohydrates to 5-HMF[119]
图9 超声探针下不同反应时间反应混合物的物理形貌(a)以及混合物离心后得到的腐黑物(b)(左:反应3 min,右:反应10 min)[123]
Fig. 9 (a) Physical appearance of sample treated with probe sonication at different reaction time, and(b) humin formation after mixture centrifuged(left: 3 mins; right: 10 mins)[123]
图10 不同加热方法示意图[36]
Fig. 10 Overview of different heating methods[36]
表6 外场辅助条件下葡萄糖转化制备5-HMF
Table 6 Conversion of glucose into 5-HMF under external fields assistance
Entry External field Catalyst Solvent Temperature( ℃) Time(min) 5-HMF yield(%) ref
1 Probe ultrasonication CrCl3 [BMIM]Cl - 10 42 123
2 Ultrasonic bath CrCl3 [BMIM]Cl - 10 - 123
3 Microwave HCl HCl/MIBK 177 240 51 36
4 Microwave SnCl4 PC/H2O 120 10 26 38
5 Hydrothermal Synthesis HCl/β-zeolite HCl 140 240 0.06 mol/L 133
6 Hydrothermal Synthesis TZ5050-C2H4O2 THF/H2O/NaCl 175 60 76 20
7 Solvent-thermal Synthesis Fe3O4@SiO2/PHA DMF 130 180 30.4 19
图11 葡萄糖制备5-HMF机理
Fig. 11 The scheme of the conversion of glucose into 5-HMF
图12 葡萄糖两步降解为5-HMF
Fig. 12 Glucose degradation to 5-HMF in two steps
图13 [EMIM]Cl与金属卤化物对葡萄糖旋光异构作用[75]
Fig. 13 Schematic diagram of optical isomerization of glucose under the action of [EMIM]Cl and metal halide[75]
图14 果糖脱水机理[86]
Fig. 14 Mechanism of fructose dehydration[86]
图15 (a) [BMIM]Br的结构,(b) 缺失电子轨道的N阳离子催化转化果糖为5-HMF[148]
Fig. 15 (a) The structure of [BMIM]Br and(b) the conversion of fructose into 5-HMF catalyzed by N cation with the missing electron orbital[148]
图16 己糖通过直链中间体路线脱水生成5-HMF
Fig. 16 Acyclic reaction pathway of dehydration of hexoses to 5-HMF
图17 3-DG转化为相应取代的呋喃醛
Fig. 17 Conversion of 3-DG to corresponding substituted furfural
图18 Al(OMe)3催化葡萄糖1通过果糖转化为5-HMF 3[152]
Fig.18 Catalytic cycle of glucose 1 to 5-HMF 3 via fructose with Al(OMe)3[152]
图19 Al-KCC-1酸催化葡萄糖脱水为5-HMF[153]
Fig. 19 Acid-catalyzed dehydration of glucose to 5-HMF with Al-KCC-1[153]
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