HMF制备FDCA的新型催化工艺研究进展

doi:10.3969/j.issn.1673-5854.2022.06.009

摘要/Abstract

摘要：

生物质转化为高附加值化学品是解决目前化石能源枯竭和全球变暖问题的有效途经，5-羟甲基糠醛（HMF）被认为是最重要的平台化合物之一，可通过氧化、加氢和开环等反应制备出许多高附加值有机化合物，其中2，5-呋喃二甲酸（FDCA）被认为是最有前景的化学品，能够代替目前广泛使用的石油基聚酯单体对苯二甲酸（PTA），用于合成生物可降解聚酯聚呋喃二甲酸乙二醇酯（PEF）。本文系统地综述了通过电化学催化氧化、光催化氧化和生物催化法将HMF制备成FDCA的新型工艺。这些催化工艺不同于传统的热解催化，其不需要高温高压，没有有害溶剂和昂贵的催化剂等，具有高效、绿色和可持续的优点。但还存在一些问题，如电化学催化法需要特殊且稳定的电解质以及对仪器设备有较高的要求；光催化法存在成本较高和能量转化率较低的问题；生物催化法有着制备周期长和反应中间体受抑制的问题。通过分析这些方法取得的成果及目前存在的问题，为未来FDCA的高效催化转化提供可行的思路。

关键词: 5-羟甲基糠醛, 2, 5-呋喃二甲酸, 电化学催化法, 光催化法, 生物催化法

Abstract:

Conversion of biomass into high value-added chemicals was an effective way to solve the current problems of fossil energy depletion and global warming. 5-Hydroxymethylfurfural(HMF) was considered as one of the most important platform compounds, which could be used to prepare many high value organic compounds through oxidation, hydrogenation, and ring-opening reactions. Among its derivatives, 2, 5-furandicarboxylic acid(FDCA) could be regarded as the most promising chemical, which could replace the widely used petroleum-based polyester terephthalic acid(PTA) to synthesize biodegradable polyester polyethylene furanoate(PEF). This article systematically reviewed the new processes for preparing FDCA from HMF through electrocatalytic oxidation, photocatalytic oxidation, and biocatalysis. These catalytic methods were different from traditional pyrolysis catalytic methods, which did not requiring high temperature and pressure as well as harmful solvents and expensive catalysts, and had the characteristics of high efficiency, greenness, and sustainability. However, there were still some problems, such as electrocatalysis needed special and stable electrolytes and high requirements for instruments and equipment; photocatalysis had the problems of high cost and low energy conversion rate; biocatalysis had long preparation cycles and the inhibited intermediates. By analyzing the results obtained by these methods and the existing problems, it provided feasible ideas for the efficient catalytic conversion of FDCA in the future.

Key words: 5-hydroxymethylfurfural, 2, 5- furandicarboxylic acid, electrocatalysis, photocatalysis, bio-catalysis

中图分类号:

TQ35

蔡佳伟, 李亢悔, 蒋涌泉, 吴述平. HMF制备FDCA的新型催化工艺研究进展[J]. 生物质化学工程, 2022, 56(6): 61-70.

Jiawei CAI, Kanghui LI, Yongquan JIANG, Shuping WU. Novel Catalytic Process for Preparing FDCA from HMF[J]. Biomass Chemical Engineering, 2022, 56(6): 61-70.

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催化剂 catalyst	反应条件 reaction conditions	FDCA产率/% yield of FDCA	FDCA选择性/% selectivity of FDCA	参考文献 ref.
AuC(II)	1 MPa O₂, 70 ℃	＞85	90	[25]
Au/HT-AC	0.5 MPa O₂, 100 ℃	—	99	[26]
Au/MgSi-ZSM-12	Mg(OH)₂, 90 ℃	98	—	[27]
Pt/RGO	NaOH, 25 ℃，24 h	84	—	[28]
Pt-ZrO₂-, ALD-30	0.4 MPa O₂, 100 ℃，12 h	97.3	97.3	[29]
Pt/NC-800	NaHCO₃, 0.4 MPa O₂，24 h	—	83.9	[30]
Pt/C	NaOH, 690 kPa O₂，6 h	79	—	[31]
Pd/C	NaOH, 690 kPa O₂，6 h	71	—	[31]
Au/TiO₂	NaOH, 2 MPa O₂，22 h	80	—	[31]
Ru/C	Mg(OH)₂, 1 MPa O₂，110 ℃	—	97.3	[32]
Ru/C	CaCO₃, 0.2 MPa O₂，120 ℃	95	—	[33]
Ru-NaY	1 MPa O₂, 120 ℃，8 h	94	—	[34]
Pd/CC	K₂CO₃, 140 ℃, 24 h	85	—	[35]
Pd-MnO₂	K₂CO₃, 100 ℃，4 h	88.1	—	[36]
Ag₃Au₇/ZrO₂	NaOH, 1 MPa O₂，125 ℃	95	—	[37]
PdAu/Cp-NH₄OH	NaOH, 300 kPa O₂，60 ℃	52	62	[38]
Fe(III)-POP-1	1 MPa空气air，100 ℃	79	—	[39]
Mn_0.75/Fe_0.25	NaOH, 0.8 MPa O₂，90 ℃，24 h	—	32	[40]
Co/Mn_0.015/Br_0.5	3 MPa O₂/CO₂，180 ℃	90	—	[41]
CoOx-MC	K₂CO₃, 0.5 MPa O₂，30 h	95.3	96.9	[42]
梅里菲尔德树脂负载钴-卟啉Merrifield resin-Co-Py	t-BuOOH, 24 h	90.4	—	[43]
Ru/Al₂O₃	K₂CO₃, 3 MPa O₂, 140 ℃	90	98	[44]
Co₄Mn₁- L	Na₂CO₃, 85 ℃，10 h	95.1	—	[45]
CoCe-0.15	0.6 MPa O₂，130 ℃	—	86.3	[46]
铜掺杂二氧化锰Cu-doped MnO₂	80 ℃, 12 h	—	96.3	[47]
Co₃O₄/Mn_0.2Co	140 ℃，24 h	＞99	—	[48]

催化剂 catalyst	反应条件 reaction conditions	法拉第效率/% faradaic efficiency	FDCA选择性% selectivity of FDCA	参考文献 ref.
Pd₁Au₂/C	KOH，0.9 V vs. RHE	—	83	[57]
OD-Ag	TEMPO，2.0 V，10 mA	90	100	[58]
Ru(III)-PEI@MWCNT	KOH，0.1 V vs. RHE	30.93	—	[59]
WO₃/Ni-0.18	KOH，1.26 V vs. RHE	88	88.3	[60]
NiSe@NiO_x	KOH，1.423 V vs. RHE	99	99	[61]
NiCoBDC-NF	KOH，1.55 V vs. RHE	78.8	99	[62]
NiOOH	KOH，1.47 V vs. RHE	96	96	[63]

催化剂 catalyst	反应条件 reaction conditions	HMF转化率/% conversion of HMF	FDCA产率/% yield of FDCA	参考文献 ref.
BiVO₄	TEMPO，1.54 V vs. RHE	100	99	[67]
WO₃	NaPi水缓冲液 aqueous NaPi buffer，0.68 V vs. RHE	—	1	[68]
ZnO/PPy	25 ℃，360 min	30	30.4	[69]
TMADT	MeCN，12 h	66.4	14.4	[70]
CoPz/g-C₃N₄	Na₂B₄O₇，14 h	99.1	96.1	[71]
Ni/CdS	NaOH	100	100	[72]

催化剂¹⁾ catalyst	反应条件 reaction conditions	FDCA产率 yield of FDCA	参考文献 ref.
AAO, UPO	H₂O₂，120 h	91%	[79]
M_3-5, PaoABC, 过氧化氢酶catalase 辣根过氧化物酶horseradish peroxidase	磷酸二氢钾缓冲溶液KPi buffer，37 ℃，6 h	100%	[80]
磁性漆酶magnetic laccase	TEMPO，96 h	90.2%	[81]
洋葱伯克霍尔德氏菌Burkholderia cepacia H-2	2 000 mg/L HMF，28 ℃，16 h	1 276 mg/L	[84]
放射耐受型甲基杆菌Methylobacterium radiotolerans G-2	1 000 mg/L HMF，26 ℃，24 h	513.9 mg/L	[85]
黄曲霉Aspergillus sp.	1 g/L HMF，14 d	0.83 g/L	[86]

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