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Progress in Chemistry 2020, Vol. 32 Issue (9): 1294-1306 DOI: 10.7536/PC200121 Previous Articles   Next Articles

• Review •

Selective HMF Oxidation into Bio-Based Polyester Monomer FDCA

Xuechen Liu1,2, Juanjuan Xing1, Haipeng Wang2, Yuanyi Zhou2, Ling Zhang2,**(), Wenzhong Wang2,**()   

  1. 1. School of Material Science & Engineering, Shanghai University, Shanghai 200072, China
    2. Shanghai Institute of Ceramics, Chinese Academy of Sciences, Shanghai 200050, China
  • Received: Revised: Online: Published:
  • Contact: Ling Zhang, Wenzhong Wang
  • Supported by:
    the General Program of National Natural Science Foundation of China(51972327, 51772312)
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Under the background of limited petroleum reserves, the conversion of renewable biomass to valuable chemicals is undoubtedly an effective strategy to alleviate the current and future resource crisis. The green chemical industry based on biomass platform molecules is gradually replacing traditional petroleum chemistry. The value-added 2,5-furandicarboxylic acid(FDCA) fabricated from the selective oxidation of the bio-based 5-hydroxymethylfurfural(HMF) is considered as an important monomer in green polymer production, such as polyethylene 2,5-furandicarboxylate(PEF). The production of FDCA from HMF generally involves thermal-, electro-, photo-, and bio-catalytic methods. Thermocatalysis is prized for the high yield and purity of FDCA but suffers from the harsh conditions, limiting its application in industry. Electrocatalysis and photocatalysis become promising for HMF conversion to FDCA due to the effective utilization of electric and solar energy to generate abundant reactive species for oxidation. In addition, the biocatalytic processes produce FDCA under mild conditions with high selectivity, which is an important development direction utilizing the biomass resources effectively in the future, although the productivity is unsatisfied at this stage. In this review, we discuss various oxidation routes and the corresponding chemical mechanisms and comprehensively review the current progress on the production of FDCA from HMF, focusing on its development and challenges. Finally, we envisage the future of selective catalytic oxidation of HMF, which might be helpful for the researchers.

Contents

1 Introduction

2 The mechanism of FDCA fabrication by selective HMF oxidation

3 Influence factors of FDCA fabrication by selective HMF oxidation

3.1 The choice of oxidant

3.2 The choice of reaction medium

3.3 Substrate adsorption over the catalysts

4 Thermocatalytic oxidation

4.1 Noble metal catalysts

4.2 Transition metal catalysts

4.3 Metal-free catalysts

4.4 The mechanism of base addition

5 Electrocatalytic oxidation

6 Photocatalytic oxidation

7 Biocatalytic oxidation

8 Conclusion and outlook

Key words: 5-hydroxymethylfurfural, 2, 5-furandicarboxylic acid, thermocatalysis, electrocatalysis, photocatalysis
Table 1 Basic physical properties of HMF and FDCA
Items HMF FDCA
Molecular weight 126.11 156.09
Boiling point/℃(760 mmHg) 291.5 419.2
Melting point/℃ 32~35 342
Density/g·cm-3(20 ℃) 1.290 1.604
Refractive Index(nD/20 ℃) 1.562 1.461
Flash point/℉ 175 168
Fig.1 Possible pathways of HMF oxidation into FDCA
Fig.2 Incorporation of 18O in the reaction steps:18O(blue) and observed units in dashed ellipses[1]
Fig.3 (a) Time course for the conversion of HMF over the Au/CNT catalyst;(b) Time course for the conversion of HMF over the Au-Pd/CNT(Au/Pd=1/1) catalyst(Reaction conditions: HMF, 0.50 mmol; HMF/Au(molar ratio), 200/1; H2O, 20 mL; O2, 0.5 MPa; temperature, 373 K)[33]
Fig.4 Overall reaction scheme and proposed mechanism for the oxidation of HMF in aqueous solution in the presence of excess base(OH-) and Pt or Au[26]
Fig.5 Conversion of HMF(%) and yield(%) of oxidation products obtained by using MnO x anodes at 1.6 V(vs RHE)(a) and Pt anodes at 2.0 V(vs RHE)(b) during the course of electrochemical oxidation of HMF in a pH=1 H2SO4 solution containing 20 mM HMF at various amounts of charge passed[56]
Fig.6 SEM images of nanostructured Ni x Co3- x O4 catalysts on 3D NF: (a) NiO,(b) Ni2CoO4,(c) Ni1.5Co1.5O4,(d) NiCo2O4, and(e) Co3O4 [62]
Fig.7 Possible mechanism of the photocatalytic oxidation of HMF into FDCA with the CoPz/g-C3N4 catalyst[82]
Fig.8 Enzymatic synthesis of FDCA via tandem oxidations[86]
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