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Progress in Chemistry 2022, Vol. 34 Issue (8): 1661-1677 DOI: 10.7536/PC210934 Previous Articles   Next Articles

• Review •

Synthesis of 2,5-Furandicarboxylic Acid by the Electrocatalytic Oxidation

Bowen Xia1,2, Bin Zhu1, Jing Liu1,3, Chunlin Chen1,2(), Jian Zhang1,2()   

  1. 1 Ningbo Institute of Materials Technology & Engineering, Chinese Academy of Sciences,Ningbo 315201, China
    2 University of Chinese Academy of Sciences,Beijing 100049, China
    3 Nano Science and Technology Institute, University of Science and Technology of China,Suzhou 215123, China
  • Received: Revised: Online: Published:
  • Contact: Chunlin Chen, Jian Zhang
  • About author:
    †These authors contributed equally to this work.
  • Supported by:
    National Natural Science Foundation of China(22072170); Zhejiang Provincial Natural Science Foundation of China(LY19B030003); Ningbo Science and Technology Bureau(2018B10056); Ningbo Science and Technology Bureau(2019B10096); Chinese Academy of Sciences(QYZDB-SSW-JSC037)
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At the 75th session of the United Nations General Assembly, China made a solemn commitment to strive to achieve carbon peaking by 2030 and carbon neutrality by 2060. Biomass, mainly produced by photosynthesis, will play an important role in the dual carbon targets. The efficient conversion of biomass can yield a range of high-value chemicals to replace fossil-derived products. Among these biomasses, 2,5-furandicarboxylic acid (FDCA) can be used to replace petroleum-based terephthalic acid (TPA) in the synthesis of bio-based furan polyesters with better thermal stability and gas barrier properties due to its similar conjugated carbon ring and diacid structure to TPA, significantly reducing the heavy reliance on fossil resources in polyester industry. In addition, FDCA is widely applied to pharmaceuticals, fragrances and metal coordination chemistry, making it one of the twelve most promising bio-based platform compounds. FDCA is typically synthesized by catalytic oxidation of 5-hydroxymethyl furfural (HMF). Compared to conventional thermocatalytic methods that require precious metal catalysts, high temperature and pressure conditions, and chemical potential as the driving force, electrocatalytic oxidation uses electrode potential as the main driving force and is a novel synthesis method that is greener and more efficient. This review summarises and analyzes the noble metal, transition metal and non-metal catalysts used in the preparation of FDCA reactions by electrocatalytic oxidation, outlines the research on catalyst design and reaction mechanisms, and points out the challenges and opportunities for the development of this field.

Contents

1 Introduction

2 Noble metal catalysts

3 Transition metal catalysts

3.1 Mono metal catalysts

3.2 Binary metal catalysts

3.3 Multiple metal catalysts

4 Non-metal catalysts

5 Mechanism

6 Conclusion and outlook

Key words: biomass upgrading, electrocatalysis, oxidation, 5-hydroxymethylfurfural, 2,5-furandicarboxylic acid
Fig. 1 Application of FDCA
Fig. 2 Publications on the synthesis of 2,5-furandicarboxylic acid by electrocatalytic oxidation in the last 10 years
Fig. 3 (a) Reaction pathways for HMF oxidation into to FDCA. (b) Time-course of FDCA yield over different electrodes. (c) Yields of HMFCA and FDCA over different electrodes after 120 min reaction[24]. Copyright 2020, American Chemical Society
Table 1 Noble metal catalysts
Electrodes Electrolyte Potential (VRHE) Conv. Yield ref
Onset electrolysis
Pt foil 0.3 M NaClO4+NaOH - 0.44 mA·cm-2 70 - 5
Pd1Au2/C 0.1 M KOH 0.3 0.9 100 83 23
(AuPd)7 NPs 1 M KOH 0.34 0.82 49.3 11.1 24
Ru(Ⅲ)a 0.1 M KOH - 1.34b - - 25
PtNiSx/CB 1 M KOH - 10 mA·cm-2 ~100 ~99 28
Ru 0.1 M Na2SO4 ~0.88 Vc 0.9 Vc 100 72.1 30
Fig. 4 Structural and morphological features of CoNW/NF[50]. Copyright 2019, The Royal Society of Chemistry
Fig. 5 Continuous flow elestrolysis. (a) Thermal and chemical stability of BHMF and HMF. (b) Schematic illustration of flow reactor and photograph of continuous flow reaction system[55].Copyright 2021, Elsevier
Fig. 6 (a) Integration of ECO and ECH of HMF[61]. (b) Paired electrolysis of HMF and p-NP[64]. Copyright 2019, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Table 2 Mono-transition metal catalysts
Electrodes Electrolyte Potential (VRHE) Conv. Yield ref
Onset electrolysis
NiOOH 1 M NaOH - 0.6a - 71 19
Ir-Co3O4 1 M KOH 1.15 1.42 100 98 26
Pt/Ni(OH)2 1 M KOH - - ~100 ~98 27
Co-P/CF 1 M KOH 1.30 1.423 100 ~90 31
Ni2P NPA/NF 1 M KOH 1.35 1.423 100 98 32
Ni3S2/NF 1 M KOH 1.35 1.423 100 98 33
NiO NPs 0.5 M KHCO3 1.524 1.5 - 30 34
Ni/NiO 1 M KOH - 1.45 - - 35
Ni(OH)2 1 M KOH - 1.39 100 100 36
NixB/NF 1 M KOH - 1.45 100 98.5 37
Ni3N@C 1 M KOH 1.35 1.45 100 98 38
S-Ni@C 1 M KOH 1.35 1.473 100 96 40
N-NiMoO4 1 M KOH ~1.36 1.473 100 97 41
Ni2S3 1 M KOH ~1.35 1.498 100 98 42
NiSe@NiOx 1 M KOH 1.35 1.423 100 99 43
Ni(NS)/CP 0.1 M KOH 1.33 1.36 99.7 99.4 44
NiBx-P0.07 0.1 M KOH ~1.4 1.464 >99 90.6 45
NiO-CMK-1 0.2 M KOH 1.70 1.85 65 79f 47
TpBpy-Ni@FTO 0.1 M LiClO4 - 1.55 96 58 48
CoNW/NF 1 M KOH 0.886 1.72b 100 96.8 50
om-Co3O4/NF 1 M KOH - 1.457 100 >99.8 51
CoO-CoSe2 1 M KOH 1.3 1.43 100 99 52
CoB/NF 1 M KOH 1.39 1.45 100 94 53
Co-P films 0.5 M NaHCO3 1.34 1.45 99 85.3 54
CoOOH/FTO 0.1 M KOH - 1.56 95.5 35.1 57
NiOOH/FTO 0.1 M KOH - 1.47 99.8 96 57
NCF 0.1 M KOH 1.25 1.62 99.9 96.4 58
CuO NWs/CuF 0.1 M KOH 1.5 1.64 99.4 90.9 59
VN/NF 1 M KOH 1.36 20 mAd 98 96f 61
MnOx 0.05 M H2SO4 - 1.6 99.9 53.8 62
Ni/NiOOH 0.1 M Na2SO4 - 1.55 100 89 63
NiBx/NF 1 M KOH - 0.6e ~100 99.8 64
hp-Ni 1 M KOH ~1.35 1.423 ~100 ~98 65
Ni foam 1 M NaOH+0.3 M ER+ - 0.2 V 100 83 66
Ni/NF 1 M NaOH - 0.7c - ~100 67
Fig. 7 (a) Geometric sites of the tetrahedron (Zn2+) or octahedron (Al3+). (b) The EXAFS spectrum of the Co R-space. (c) The electrochemical performance for CuCo2O4 in comparison to Co3O4. (d) The concentration of HMF and its oxidation products during the electrochemical oxidation of HMF on CuCo2O4[81]. Copyright 2020, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Table 3 Binary transition metal catalysts
Electrodes Electrolyte Potential (VRHE) Conv. Yield ref
Onset electrolysis
NiFe LDH 1 M KOH 1.25 1.33 98 98 14
WO3/Ni-0.18 1 M KOH 1.32 1.57 99.4 88.3 60
FeSn2/NF 1 M KOH - 10 mA - ~90 69
NiCo2O4/NF 0.1 M KOH - 1.55 ~100 ~90 71
NiCo2O4/NF 1 M KOH ~1.2 1.5 99.6 90.8a 72
t-Ni1Co1-MOF 1 M KOH - - ~100 ~100 73
NiCoBDC-NF 0.1 M KOH - 1.55 - 99 74
CuNi(OH)2/C 1 M KOH - 1.45 100 93.3 75
Ni0.9Cu0.1(OH)2 1 M KOH - 1.45 ~100 91.2 76
N-MoO2/Ni3S2 1 M KOH - 1.623 >90 - 77
Ni3N-V2O3 1 M KOH - - ~100 96.1 78
NiP-Al2O3/NF 1 M KOH - 1.45 98.2 99.6a 79
MoO2-FeP@C 1 M KOH 1.323 1.424 99.4 98.6a 80
CuCo2O4 1 M KOH 1.23 1.45 - 93.7 81
NiO-Co3O4 1 M KOH 1.28 1.45 - 98 82
Cu1.8Co0.2PO4F 1 M KOH ~1.2 1.45 ~100 85 83
E-CoAl-LDH 1 M KOH 1.30 1.52 ~100 ~95 84
NiCo2O4-CFP 1 M KOH ~1.35 1.43 98.4 ~94.3a 85
TiOx@MnOx 0.1 M HClO4 1.4 1.69 100 24 86
CuMn2O4 1 M KOH - 1.31 100 96 87
NiFeOx 1 M KOH - 25 mA·cm-2 100 - 88
Table 4 Multiple transition metal catalysts
Electrodes Electrolyte Potential (VRHE) Conv. Yield ref
Onset electrolysis
NiCoFe-LDHs 1 M NaOH ~1.44 1.54 95.5 84.9 89
NiCoMn-LDHs 1 M NaOH 1.42 1.5 100 91.7 90
CoNiFe-MOFs/NF 1 M KOH - 1.4 100 99.76 91
CoFe@NiFe 1 M KOH 1.28 1.4 100 ~100 92
P-HEOs/CP 1 M KOH 1.35 1.5 99 97.4 94
CuxS@NiCo-LDH 1 M KOH 1.19 1.32 100 ~99 95
Table 5 Non-metal catalysts
Electrodes Electrolyte Potential (VRHE) Conv. Yield ref
Onset electrolysis
TEMPO pH=9.2 buffer - 1.54 >99 >99 21
BNC 0.1 M KOH - 1.9 71 57 96
ACT pH=9.2 buffer - 0.7 Va ~100 97 97
TEMPO pH=10 buffer - 1.6 99.9 93.8 98
ACT pH=10 buffer - 1.6 99.9 92.6
TEMPO pH=9.2 buffer 0.6 Vb 100 98.8 101
Fig. 8 Reaction pathways for the electrochemical oxidation of HMF to FDCA
Fig. 9 In-situ SFG spectra recorded (a) at various voltages for 90 min electrolysis and (b) at different times at a constant 1.45 VRHE in 1 mol/L KOH with 20 mmol/L HMF[38]. Copyright 2019, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Fig. 10 (a) Construction of catalysts with SERS response. In situ SERS spectra of (b) catalyst and (c) surface furans. (d) Reaction mechanism of HMF oxidation in 1 mol/L KOH[109,111]. Copyrights 2020, The Royal Society of Chemistry
Fig. 11 Research trends in active electrocatalysts (TEMPO is classified as a carbon based catalyst)
Fig. 12 Global research intensity in the synthesis of FDCA by electrocatalytic oxidation
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