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化学进展 2021, Vol. 33 Issue (2): 318-330 DOI: 10.7535/PC200441 前一篇   

• 综述 •

选择性氧化HMF

程丽丽1, 章赟1, 朱烨坤1, 吴瑛1,*()   

  1. 1 浙江师范大学物理化学研究所 金华 321004
  • 收稿日期:2020-04-23 修回日期:2020-07-09 出版日期:2021-02-24 发布日期:2020-10-15
  • 通讯作者: 吴瑛
  • 基金资助:
    浙江省自然科学基金项目(LY16B030002)
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Selective Oxidation of HMF

Lili Cheng1, Yun Zhang1, Yekun Zhu1, Ying Wu1,*()   

  1. 1 Institute of Physical Chemistry, Zhejiang Normal University, Jinhua 321004, China
  • Received:2020-04-23 Revised:2020-07-09 Online:2021-02-24 Published:2020-10-15
  • Contact: Ying Wu
  • About author:
    * Corresponding author e-mail:
  • Supported by:
    Natural Science Foundation of Zhejiang Province(LY16B030002)

近年来,利用储量丰富且可再生的生物质资源制备高附加值化学品和液体燃料是目前化学研究领域的热点之一,同时契合可持续发展的国家战略。5-羟甲基糠醛(HMF)是关键的生物质平台化合物之一,广泛应用于制备精细平台化合物、药物的中间体、聚合物的合成、液体燃料的前驱体等。因此,HMF的选择性氧化逐渐成为生物质领域的研究热点。本文主要介绍了近五年来关于HMF选择氧化制备DFF、FFCA、FDCA等生物质衍生物的研究,以及以HMF为中间体的生物质转化过程。关于对HMF进行选择性氧化,主要聚焦于以热催化和光催化两种途径。其中,以热催化的途径将HMF选择性氧化为DFF和FDCA研究较多,此途径下的催化体系主要介绍了贵金属和非贵金属两类;而在为数不多的光催化途径下,主要研究的催化体系是g-C3N4催化剂。最后,指出了目前HMF氧化反应研究存在的不足,并提出了可能解决的方法。

关键词： 纤维素, 葡萄糖, 果糖, 选择性氧化, HMF

In recent years, the use of abundant and renewable biomass resources to prepare high value-added chemicals and liquid fuels is one of the hot spots in the chemical research field, which is in line with the national strategy of sustainable development. 5-hydroxymethylfurfural(HMF)is one of the key biomass platform compounds, widely used in the preparation of fine platform compounds, drug intermediates, polymer synthesis and liquid fuel precursor. Therefore, the selective oxidation of HMF has gradually become a research hotspot in the field of biomass. This paper mainly introduces the research on preparation of biomass derivatives such as DFF, FFCA and FDCA by selective oxidation of HMF in last five years, and the transformation of biomass with HMF as intermediate. The selective oxidation of HMF mainly focuses on two ways:thermalcatalytic and photocatalytic. Among them, the selective oxidation of HMF to DFF and FDCA by thermalcatalytic is widely studied. The catalytic system in this approach mainly includes the noble metals and non-precious metals, which are introduced herein. In the few photocatalytic pathways, the main catalytic system is g-C3N4 catalyst. In addition, the deficiencies in the research on the oxidation of HMF are pointed out and the possible solutions are proposed.

Contents

1 Introduction

2 Summary of HMF

2.1 Property of HMF

2.2 The reaction path of HMF catalytic oxidation

3 Selective oxidation of HMF

3.1 Thermalcatalytic selective oxidation of HMF

3.2 Photocatalytic selective oxidation of HMF

4 The biomass oxidation reaction with HMF as intermediate

5 Conclusion and outlook

Key words: cellulose, glucose, fructose, selective oxidation, HMF
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图1 HMF催化氧化的反应路径[8]
Fig. 1 The reaction path of HMF catalytic oxidation[8]
图2 Cs-MnOx选择性氧化HMF的反应机理[26]
Fig. 2 Reaction mechanism of selective oxidation of HMF by Cs-MnOx[26]
图3 Mn6Fe1Ox将HMF氧化为DFF的可能反应路线[31]
Fig. 3 A possible reaction route for oxidation of HMF by Mn6Fe1Ox to DFF[31]
表1 不同催化剂催化氧化HMF合成DFF
Table 1 Synthesis of DFF by the oxidation of HMF on different catalysts
Catalyst Solvent Reaction conditions DFF yield ref
Fe3O4@SiO2-NH2-Ru(Ⅲ) toluene 120 ℃, 4 h 86.4% 13
Fe3O4@SiO2-NH2-Ru(Ⅲ) toluene 16 h, air 86.8% 13
ZrP-Ru chlorine toluene 130 ℃, 12 h 62% 16
Ru/MnCo2O4 toluene 130 ℃, 1.0 MPa O2 98.3% 17
Cs-MnOx DMF 100 ℃, 10 h, 1 bar O2 94.7% 26
Cu-MnO2 ethanol 140 ℃, 5 h, 0.3 MPa O2 96.1% 27
N-MnO2 toluene 6 h, 0.1 MPa O2 99.9% 28
Mn6Fe1Ox DMF 110 ℃, 5 h, 1.5 MPa O2 98% 31
Mn-Co ethanol 140 ℃, 2 h, 30 bar air 98% 32
CoMn2O4 DMF 100 ℃, 2 h, 0.8 MPa O2 100% 33
MgO-Ce2O water 100 ℃, 15 h, 0.9 MPa O2 98% 37
MgO-MnO2-CeO2 water 100 ℃, 6 h, 2.0 MPa O2 94.9% 41
V-CS DMSO 120 ℃, 9 h 99% 43
VPO DMSO 120 ℃, 10 h 83.6% 44
VOx water 130 ℃, 1 h, 3.0 MPa O2 95.4% 45
CSTi water 70 ℃, 1 bar O2 88% 47
表2 不同催化剂将HMF选择性氧化到FDCA
Table 2 Selective oxidation of HMF to FDCA on different catalysts
Catalyst Oxidant Reaction conditions FDCA yield ref
Ru/ZrO2 10 bar O2 120 ℃, 16 h, water 97% 8
Ru/MgAlO 90 psi O2 160 ℃, 4 h 99% 10
5 wt% Ru/C 4 MPa O2 130 ℃, 12 h, DMSO/water 93% 11
5 wt% Ru/C 1 MPa O2 100 ℃, MgOH 97.3% 12
Ru/MnCo2O4 2.4 MPa O2 120 ℃, 10 h, water 99.1% 18
Pt/TiO2 40 bar O2 100 ℃, 6 h, Na2CO3 84% 19
Pt/ZrO2 4 bar O2 100 ℃, 12h 95% 19
Pt/ZrO2 0.4 MPa O2 100 ℃, 12h 97.3% 20
Pt/Fe3O4/rGO 0.5 MPa O2 95 ℃, 0.5 h, water 98% 21
Pd/CC 20 mL/min O2 140 ℃, 30 h, water 85% 22
γ-Fe2O3@HAP-Pd(0) 30 mL/min O2 100 ℃, 6 h 92.9% 23
Au-Pd 10 bar O2 100 ℃, Na2CO3 93.2% 24
Co-Mn-0.25 1 MPa O2 120 ℃, 5 h 95% 34
Co3O4/MnxCo 1 bar O2 140 ℃, 4 h 88% 35
MNPs TBHP 100 ℃, 5 h 85% 36
MnOx-CeO2 2 MPa O2 110 ℃, 6 h 91% 39
MnOx-CeO2 1 MPa O2 100 ℃, 24 h, NaHCO3 91% 40
MnO2 2 MPa O2 130 ℃, 12 h 75.5% 41
CuO·MnO2·CeO2 2 MPa O2 130 ℃, 12 h 71% 42
表3 不同催化剂将生物质转化为HMF衍生物
Table 3 Different catalysts convert biomass into HMF derivatives
Material Catalyst DFF FDCA ref
fructose MoOx/CS 78% 82
fructose MoO3-ZrO2 74% 83
fructose Ce10-xMoxOδ 74% 84
fructose Mo-HNC 77% 85
fructose PMA-MIL-101 75.1% 86
fructose Cs0.5H2.5PMo12 69.3% 87
fructose WO3HO-VO-SiO2@Fe3O4 71% 88
fructose MOF 99% 89
fructose graphene oxide 53% 90
fructose graphene oxide 72.5% 91
fructose VO-MOR zeolite 96% 92
fructose α-CuV2O6 63% 93
fructose Pt/C 93% 96
fructose Co-Al 87% 97
fructose Co-Al 77% 97
fructose Co-Al 59% 97
glucose AlCl3-6H2O/NaBr/V compound 35%~48% 102
glucose CrCl3-6H2O/NaBr/NaVO3-2H2O 55% 103
glucose Hydrotalcite/Amberlyst-15/Ru/HT 25% 104
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摘要

选择性氧化HMF