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化学进展 2020, Vol. 32 Issue (9): 1294-1306 DOI: 10.7536/PC200121 前一篇   后一篇

• 综述 •

HMF催化合成生物基聚酯单体FDCA

刘雪晨1,2, 邢娟娟1, 王海鹏2, 周沅逸2, 张玲2,**(), 王文中2,**()   

  1. 1. 上海大学材料科学与工程学院 上海 200072
    2. 中国科学院上海硅酸盐研究所 上海 200050
  • 收稿日期:2020-01-08 修回日期:2020-05-15 出版日期:2020-09-24 发布日期:2020-06-30
  • 通讯作者: 张玲, 王文中
  • 作者简介:
    ** Corresponding author e-mail: (Ling Zhang); (Wenzhong Wang)
  • 基金资助:
    *国家自然科学基金面上项目(51972327, 51772312)
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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:2020-01-08 Revised:2020-05-15 Online:2020-09-24 Published:2020-06-30
  • Contact: Ling Zhang, Wenzhong Wang
  • Supported by:
    the General Program of National Natural Science Foundation of China(51972327, 51772312)

在石油资源日渐紧缺的背景下,充分利用自然界中可再生的生物质资源无疑是缓解当前和未来资源危机的有效手段,基于生物质平台分子的绿色化工正在逐渐替代传统石化产品的生产模式。来源于生物质的5-羟甲基糠醛(HMF)经过催化氧化可合成高附加值化学品2,5-呋喃二甲酸(FDCA)。FDCA是生产绿色聚合物聚2,5-呋喃二甲酸乙二酯(PEF)的重要单体。综合近年来利用热、电、光与生物催化模式进行的HMF氧化研究成果,热催化在产率与产品纯度方面显示出明显优势,但其对高能耗与高氧压的依赖限制了在工业中的应用。以电催化和光催化为基础的催化模式能够高效利用电能和太阳能,氧化活性物种丰富可调,有广阔应用前景。此外,生物催化模式虽目前产率较低,但具有反应条件温和、选择性高的突出特点,是未来有效利用生物质资源的重要发展方向。本文对氧化途径与相应反应机理进行讨论,并全面地总结了目前由HMF催化氧化生产FDCA的研究现状,包括已取得的进展与将面临的挑战,最后对未来发展方向与前景进行了展望。

关键词： 5-羟甲基糠醛, 2, 5-呋喃二甲酸, 热催化, 电催化, 光催化

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
()
表1 HMF与FDCA的基本物理性质
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
图1 HMF在氧化为FDCA过程中可能经历的反应路线
Fig.1 Possible pathways of HMF oxidation into FDCA
图2 在HMF氧化FDCA的反应中加入18O标记试剂 (18O:蓝色),所观察到的产物由椭圆虚线圈出[1]
Fig.2 Incorporation of 18O in the reaction steps:18O(blue) and observed units in dashed ellipses[1]
图3 (a) HMF在Au/CNT催化剂上转化的过程;(b) HMF在Au-Pd/CNT催化剂上转化的过程;(反应条件:HMF为0.50 mmol;HMF/Au(摩尔比)200/1;H2O 20 mL; O2 0.5 MPa; 温度373 K)[33]
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]
图4 在过量碱(OH-)和Pt或Au的存在下,HMF在水溶液中氧化可能的反应机理示意图[26]
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]
图5 在1.6 V(vs RHE)下使用MnO x 阳极(a)与在2.0 V(vs RHE)使用Pt阳极(b)的HMF随时间变化的转化率与各产物选择性(反应在含20 mM HMF的pH=1的H2SO4溶液进行)[56]
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]
图6 在泡沫镍基底上不同比例Ni x Co3-xO4催化剂的3D模拟与SEM图像: (a) NiO,(b) Ni2CoO4,(c) Ni1.5Co1.5O4,(d) NiCo2O4和(e) Co3O4 [62]
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]
图7 CoPz/g-C3N4光催化氧化HMF制备FDCA的可能机理[82]
Fig.7 Possible mechanism of the photocatalytic oxidation of HMF into FDCA with the CoPz/g-C3N4 catalyst[82]
图8 串联氧化酶法合成FDCA的两步反应过程[86]
Fig.8 Enzymatic synthesis of FDCA via tandem oxidations[86]
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摘要

HMF催化合成生物基聚酯单体FDCA