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化学进展 2021, Vol. 33 Issue (11): 2128-2137 DOI: 10.7536/PC200859 前一篇   后一篇

• 综述 •

化学催化葡萄糖异构化果糖

刘毅强1, 裘依梅1, 唐兴1,2,*(), 孙勇1,2, 曾宪海1,2, 林鹿1,2   

  1. 1 厦门市生物质清洁高值化利用重点实验室 厦门大学能源学院 厦门 361102
    2 福建省生物质清洁高值化技术工程研究中心 厦门 361102
  • 收稿日期:2020-08-24 修回日期:2020-09-27 出版日期:2021-11-20 发布日期:2020-12-28
  • 通讯作者: 唐兴
  • 基金资助:
    国家重点研发计划项目(2019YFB1503903); 广东省重点领域研发计划项目(2020B0101070001); 国家自然科学基金项目(21706223); 国家自然科学基金项目(21506177); 厦门大学校长基金(20720190014)
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Glucose Isomerization into Fructose by Chemocatalytic Route

Yiqiang Liu1, Yimei Qiu1, Xing Tang1,2(), Yong Sun1,2, Xianhai Zeng1,2, Lu Lin1,2   

  1. 1 Xiamen Key Laboratory of Clean and High-valued Utilization for Biomass, College of Energy, Xiamen University,Xiamen 361102, China
    2 Fujian Engineering and Research Center of Clean and High-Valued Technologies for Biomass,Xiamen 361102, China
  • Received:2020-08-24 Revised:2020-09-27 Online:2021-11-20 Published:2020-12-28
  • Contact: Xing Tang
  • Supported by:
    National Key R&D Program of China(2019YFB1503903); Key-Area Research and Development Program of Guangdong Province(2020B0101070001); National Natural Science Foundation of China(21706223); National Natural Science Foundation of China(21506177); Fundamental Research Funds for the Central Universities(20720190014)

基于糖平台的生物炼制可以制备各种碳基化学品、材料和燃料。相较于葡萄糖和纤维素,果糖更容易高选择性地催化转化制备5-羟甲基糠醛等重要的生物质基平台分子,因此葡萄糖异构化果糖已经成为生物炼制过程中的重要反应步骤之一。本文详细介绍了葡萄糖经化学催化异构化果糖的反应机理,并基于异构化催化剂全面总结了近年来化学催化葡萄糖异构化果糖的研究进展。此外,本文在分析各种葡萄糖异构化催化剂及其催化作用的基础上,进一步对化学催化葡萄糖异构化果糖的未来研究方向进行了展望。

关键词： 葡萄糖, 果糖, 异构化, 化学催化剂

The biorefinery based on sugar platform can produce various carbon-based chemicals, materials, and fuels. Compared with glucose and cellulose, a facile conversion of fructose into versatile biomass-based platform molecules such as 5-hydroxymethylfurfural with desirable selectivity can be expected, thus the isomerization of glucose into fructose has become one of the vital reactions for biorefinery. In this review, an in-depth discussion on the reaction mechanism of glucose isomerization by chemocatalytic route is provided, and the recent research progress on glucose isomerization into fructose in the view of isomerization catalysts is comprehensively summarized. Based on the discussion on the catalysts for glucose isomerization and their catalysis, the ongoing research on the chemocatalytic isomerization of glucose into fructose is envisaged.

Contents

1 Introduction

2 Mechanism of glucose isomerization into fructose

2.1 Isomerization mechanism over basic catalysts

2.2 Isomerization mechanism over acidic catalysts

3 Homogeneous catalysts

3.1 Base catalysts

3.2 Acid catalysts

4 Heterogeneous catalysts

4.1 Hydrotalcites

4.2 Metal oxides and insoluble salts

4.3 Zeolites

4.4 Alkaline resins

4.5 Metal organic frameworks

5 Conclusion and outlook

Key words: glucose, fructose, isomerization, chemo-catalysts
()
图1 碱催化葡萄糖异构化果糖的质子转移机理
Fig. 1 Mechanism of base catalyzed proton transfer for glucose isomerization into fructose
图2 葡萄糖异构化果糖的氢负离子转移机理
Fig. 2 Mechanism of hydride transfer for glucose isomerization into fructose.
表1 均相催化剂催化葡萄糖异构化果糖的代表性实验数据
Table 1 Representative experimental data for glucose isomerization into fructose catalyzed by homogeneous catalysts
Catalyst Solvent T(℃) t(min) Fructose yield(%) Glucose conversion(%) ref
Ca(OH)2 D2O 100 180 11 14 26
KOH H2O 78 60 11 18 27
Na2B4O7+NaOH H2O 100 1.5 90 -- 28
NaAlO2 H2O 55 180 41 56 29
NaAlO2 DMSO/PG/H2O 55 180 49 68 29
Et3N H2O 100 30 31 57 30
Morpholine H2O 100 30 17 40 30
Piperazine H2O 100 30 28 45 30
Ethylenediamine H2O 100 30 25 40 30
Piperidine H2O 100 30 29 57 30
Pyrrolidine H2O 100 30 29 49 30
L-Arginine H2O 120 15 31 41 19
Spermin H2O 100 15 29.7 40 31
Ch Pro H2O 70 30 38 49 32
ChPhen+Na2B4O7 H2O 70 7 64.7 89 33
SnCl4·5H2O H2O 120 180 4.7 18 24
CrCl3·6H2O H2O 120 180 25.4 52 24
CrCl3·6H2O H2O/DMSO 110 180 20.7 30 34
AlCl3·6H2O H2O 120 180 26.3 32 24
图3 水体系中AlCl3催化葡萄糖异构化机理[24]
Fig. 3 Mechanism of glucose isomerization catalyzed by AlCl3 in water[24]
表2 水滑石催化剂催化葡萄糖异构化果糖的代表性实验数据
Table 2 Representative experimental data for glucose isomerization into fructose catalyzed by hydrotalcites
Catalyst Solvent T(℃) t(min) Fructose yield(%) Glucose conversion(%) ref
DHT-4A2 H2O 90 9 9.6 10 41
Mg-Al HT H2O 110 90 30 34 42
Mg-Al HT DMF 100 300 34.6 50 43
Mg-Al HT DMF 100 180 36.6 42 44
Mg-Al HT 1-butanol 120 300 51 62 45
Mg-Al HT H2O 90 120 31 41 46
表3 金属氧化物和难溶盐催化葡萄糖异构化果糖的代表性实验数据
Table 3 Representative experimental data for glucose isomerization into fructose catalyzed by metal oxides and insoluble salts
Catalyst Solvent T(℃) t(min) Fructose yield(%) Glucose conversion(%) ref
MgO-ZrO2 H2O 95 360 35.7 51 52
CaO-ZrO2 H2O 140 15 21.6 25 53
Fe3O4@SiO2-TMG H2O 120 60 25 46 20
ZrC H2O 120 20 34 45 54
Hybrid tin-silicate H2O 110 120 16.7 23 56
Na9Si12Ti5O38(OH) H2O 100 120 39 46 55
H)Ti2O2[Si2O6]2 H2O 100 120 34 55 55
HKCa2Si8O19 H2O 100 120 34 53 55
Ca5Si6O17 H2O 100 120 35 51 55
表4 分子筛催化葡萄糖异构化果糖的代表性实验数据
Table 4 Representative experimental data for glucose isomerization into fructose catalyzed by zeolites
Catalyst Solvent T(℃) t(min) Fructose yield(%) Glucose conversion(%) ref
Sn-beta H2O 110 30 31 54 57
Ti-beta H2O 140 90 23 51 57
Sn-MCM-41 H2O 140 90 12 30 57
Alkaline metal-containing A, X and Y type zeolites H2O 95 - 4~22 7~26 76
Sn-beta H2O 110 120 32 41 77
Sn-beta Dioxane/H2O 90 240 41.5 67 69
Sn-beta H2O 120 120 47.2 60.2 66
H-USY Methanol+H2O 120 60+60 55 72 71
H-beta Methanol+H2O 120 60+60 40 70 71
Sn-MFI H2O 80 120 27 37 63
Sn-SPP Ethanol+H2O 90 24 h+24 h 66.5 88 74
MgNaY H2O 100 30 31 36 64
MgO/NaY H2O 100 120 33.8 50 65
Sn-MWW Ethanol+H2O 90 8 h+24 h 54.6 75 75
图4 Sn-beta表面部分水解的Sn中心[22]
Fig. 4 Partially hydrolyzed Sn center over the surface of Sn-beta[22]
表5 离子交换树脂和MOF催化葡萄糖异构化果糖的代表性实验数据
Table 5 Representative experimental data for glucose isomerization into fructose catalyzed by alkaline resins and MOFs
Catalyst Solvent T(℃) t Fructose yield(%) Glucose conversion(%) ref
Hydroxide resin H2O 87 40 h 32 84 79
Aluminate resin H2O 2 42 day 72 90 80
A-26 resin Ethanol 360 180 min 49.7 53 81
MIL-101 H2O 100 24 h 12.6 22 84
MIL-101-SO3H H2O 100 24 h 21.6 21.6 84
MIL-101 Ethanol+H2O 100 24 h+24 h 24.3 39 85
Cr(OH)3/MIL-101 Ethanol+H2O 100 24 h+24 h 59.3 77 85
UiO-66-Fm Propanol+H2O 90 24 h+24 h 34 47 86
图5 甲醇中和水中的异构化/水解两步法转化葡萄糖制果糖[71]
Fig. 5 The conversion of glucose into fructose by two-step strategy(isomerization and hydrolysis) in methanol and water[71]
图6 MIL-101催化葡萄糖异构化机理
Fig. 6 Mechanism of glucose isomerization catalyzed by MIL-101
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摘要

化学催化葡萄糖异构化果糖