磁性MnO2-Fe3O4复合氧化物催化5-羟甲基糠醛氧化合成2,5-呋喃二甲酸研究

卢虹竹; 白继峰; 闫飞; 张新月; 金颖; 王景芸; 陈平; 周明东

doi:10.1016/S1872-5813(21)60020-8

磁性MnO₂-Fe₃O₄复合氧化物催化5-羟甲基糠醛氧化合成2,5-呋喃二甲酸研究

doi: 10.1016/S1872-5813(21)60020-8

卢虹竹^1,,
白继峰¹,
闫飞²,
张新月¹,
金颖¹,
王景芸^1, ,,
陈平¹,
周明东^1, ,

1.
辽宁石油化工大学石油化工学院，辽宁抚顺 113001
2.
辽宁省产品质量监督检验院，辽宁沈阳 110032

基金项目: 兴辽英才计划项目(XLYC1902085)，辽宁省自然科学基金指导计划项目（20170540590）和中石油创新基金项目（2018D-5007-0507）资助

详细信息

通讯作者:
Tel: 024-56863837，E-mail：jingyun.wang@lnpu.edu.cn

mingdong.zhou@lnpu.edu.cn

中图分类号: O643.36
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出版历程
- 收稿日期: 2020-11-26
- 修回日期: 2020-12-18
- 网络出版日期: 2021-03-19
- 刊出日期: 2021-03-19

Oxidation of 5-hydroxylmethylfurfural to 2, 5-furandicarboxylic acid catalyzed by magnetic MnO₂-Fe₃O₄ composite oxides

1.
School of Petrochemical Technology, Liaoning Shihua University, Fushun 113001, China
2.
Liaoning Province Product Quality Supervision and Inspection Institute, Shenyang 110032, China

Funds: The project was supported by Liaoning Revitalization Talents Program (XLYC1902085), Natural Science Foundation of Liaoning Province (20170540590) and PetroChina Innovation Foundation (2018D-5007-0507).

摘要

摘要: 以不同晶型的MnO₂为催化剂进行5-羟甲基糠醛（HMF）氧化反应，并将催化活性较高的α-MnO₂与Fe₃O₄复合制备磁性MnO₂-Fe₃O₄复合氧化物，采用X射线衍射（XRD）、扫描电镜（SEM）、X射线光电子能谱（XPS）、NH₃/CO₂程序升温脱附（NH₃/CO₂-TPD）及吡啶吸附红外光谱（Py-FTIR）对催化剂的结构和性质进行表征和分析。结果表明，复合后的催化剂仍保持α-MnO₂和Fe₃O₄基本结构，但催化剂中活性中心Mn⁴⁺·O²⁻离子对数量增加，使其对HMF氧化反应的催化活性相对α-MnO₂和Fe₃O₄显著提升。对HMF氧化制备2,5-呋喃二甲酸（FDCA）的反应条件进行优化，复合催化剂Mn₈Fe₃O_x对HMF表现出良好的催化活性，在最优化条件下，HMF可完全转化，FDCA收率为76.9%。
- 5-羟甲基糠醛 /
- 氧化 /
- 磁性Mn-Fe复合氧化物 /
- 2,5-呋喃二甲酸
Abstract: MnO₂ with different crystal structures was used to catalyze the oxidation reaction of 5-hydroxylmethylfurfural (HMF), and α-MnO₂ exhibited the highest catalytic activity. Magnetic MnO₂-Fe₃O₄ oxides were prepared by α-MnO₂and Fe₃O₄ and characterized by X-ray diffraction (XRD), scanning electron microscope (SEM), X-ray photoelectron spectroscopy (XPS), temperature programmed desorption of NH₃/CO₂ (NH₃/CO₂-TPD) and Fourier transform infrared reflection spectra of pyridine adsorption (Py-FTIR). The results showed that the composite catalyst still maintained the basic structure of α-MnO₂and Fe₃O₄, whereas the number of active center Mn⁴⁺·O²⁻ion pair increased compared with α-MnO₂and Fe₃O₄, which significantly improved the catalytic activity on HMF oxidation reaction. The reaction conditions of HMF oxidation to 2,5-furandicarboxylic acid (FDCA) were optimized. The composite oxide Mn₈Fe₃O_x showed the best catalytic performance for HMF oxidation. HMF could be completely converted, with 76.9% of FDCA yield under the optimal conditions.
- 5-hydroxymethylfurfural /
- oxidation /
- magnetic MnO₂-Fe₃O₄ mixed oxides /
- 2,5-furanedioic acid

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图 1 不同晶型MnO₂ 的XRD谱图

Figure 1 XRD patterns of MnO₂ with various crystal structures

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图 2 不同晶型MnO₂ XPS谱图

Figure 2 XPS spectra of MnO₂ with various crystal structures

(a): Mn 2p; (b): O 1s

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图 3 Mn-Fe复合金属氧化物的XRD谱图

Figure 3 XRD patterns of Mn-Fe mixed oxide catalysts

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图 4 Fe₃O₄、α-MnO₂和Mn₈Fe₃O_x的SEM照片

Figure 4 SEM images of Fe₃O₄ (a), MnO₂ (b) and Mn₈Fe₃O_x (c)

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图 5 Mn₈Fe₃O_x和α-MnO₂ XPS谱图：（a）Mn₈Fe₃O_x XPS全扫描谱图，（b）Fe 2p XPS谱图，（c）Mn 2p XPS谱图，（d）O 1s XPS谱图

Figure 5 XPS spectra of Mn₈Fe₃O_x and α-MnO₂: (a) Wide survey XPS spectrum of Mn₈Fe₃O_x, high resolution XPS spectra (b) Fe2p, (c) Mn2p, and (d) O 1s of Mn₈Fe₃O_x and MnO₂

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图 6 催化剂NH₃-TPD (a)和CO₂-TPD (b)曲线

Figure 6 NH₃-TPD (a) and CO₂-TPD (b) profiles of various catalysts

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图 7 催化剂Py-FTIR谱图

Figure 7 Py-FTIR spectra of various catalysts

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图 8 反应温度对HMF氧化反应的影响

Figure 8 Influence of reaction temperature on HMF oxidation

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图 9 反应时间对HMF氧化反应的影响

Figure 9 Influence of reaction time on HMF oxidation product yield

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图 10 催化剂Mn₈Fe₃O_x重复使用情况

Figure 10 Reuse of Mn₈Fe₃O_x for HMF oxidation

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表 1 不同氧化物催化的HMF氧化反应

Table 1 Perfomance of different catalysts on oxidation of HMF

Catalyst	Conversion/%	HMFCA /%	DFF /%	FFCA /%	FDCA /%	Total yield/%
−	40.5	4.1	10.2	7.8	0	22.1
α-MnO₂	83.2	3.0	13.6	19.4	13.3	62.3
γ-MnO₂	78.2	2.6	8.6	25.6	4.5	41.3
δ-MnO₂	77.3	5.4	7.5	20.3	2.6	35.8
Fe₃O₄	76.8	2.6	20.1	30.1	5.4	58.2
Mn₃Fe₈O_x	86.8	3.2	20.1	39.4	14.6	75.3
Mn₁Fe₁O_x	89.5	4.8	19.8	35.7	15.4	75.7
Mn₈Fe₃O_x	97.3	5.4	18.7	43.8	23.6	91.5

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表 2 催化剂的酸量和减量

Table 2 The acidity and basicity of various catalysts

Sample	Acidity/(μmol·g⁻¹)	Basicity/(μmol·g⁻¹)
Fe₃O₄	416.0	6.1
MnO₂	465.2	11.6
Mn₈Fe₃O_x	499.5	12.9

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表 3 不同溶剂对HMF氧化反应的影响

Table 3 Influence of different solvents on oxidation of HMF

Solvent	Conversion /%	HMFCA /%	DFF /%	FFCA /%	FDCA /%	Total yield /%
DMSO	97.3	5.4	18.7	43.8	23.6	91.5
MeCN	81.2	13.5	26.7	9.8	7.8	57.8
DMF	43.5	0.9	0.8	5.1	0	6.8
H₂O	28.6	0	13.7	5.4	0	19.1
Ethanol	20.7	5.3	6.9	0.9	0	13.1

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表 4 氧化剂和催化剂用量对HMF氧化反应的影响

Table 4 Influence of the dosage of oxidant and catalyst on HMF oxidation

Oxidant dosage (equiv.)	Catalyst dosage /(g·mL⁻¹)	Conversion /%	DFF /%	FFCA /%	FDCA /%	Total yield /%
3.0	0.002	43.6	16.5	19.6	2.1	38.2
6.5	0.002	97.3	18.7	43.8	23.6	91.5
9.0	0.002	100	15.9	35.9	24.4	77.5
6.5	0.010	100	15.4	38.5	37.9	91.8
6.5	0.020	100	10.5	29.5	54.1	94.1
6.5	0.030	100	8.2	28.1	54.4	90.7
6.5	0.040	100	7.3	28.4	54.6	90.3

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表 5 正交结果分析

Table 5 Analysis of orthogonal design

Entry	Temp./℃	Time/h	Oxidant dosage(equiv.)	Catalyst dosage/(g·mL⁻¹)	FDCA/%
1	70	18	3.0	0.01	13.4
2	70	24	6.5	0.02	68.8
3	70	30	9.0	0.03	75.6
4	80	18	6.5	0.03	40.5
5	80	24	9.0	0.01	74.6
6	80	30	3.0	0.02	27.0
7	90	18	9.0	0.02	37.8
8	90	24	3.0	0.03	10.9
9	90	30	6.5	0.01	32.4
k₁	52.6	30.6	17.1	40.1
k₂	47.3	51.4	47.2	44.5
k₃	27.0	45	62.7	42.3
R	25.6	20.8	45.6	4.4

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表 6 Mn₈Fe₃O_x催化性能与文献报道其他催化剂比较

Table 6 Comparison of the catalytic activity of Mn₈Fe₃O_x with those of other heterogeneous catalysts reported in the latest literature

Catalyst	Oxidants	Base	Temp./℃	Time/h	Conversion/%	FDCA/%	Ref.
Mn₈Fe₃O_x	TBHP	−	70	24	100	76.9	this work
Au/TiO₂	10 bar air	4 equiv. NaOH	130	5	100	84	36
Pd/Al₂O₃	1 bar O₂	1.25 equiv. NaOH	90	8	> 99	78	37
Ru/AC	40 bar air	4 equiv. NaHCO₃	100	2	100	75	38
Pt/C	40 bar air	2 equiv. Na₂CO₃	100	6	99	69	12
Nano-Fe₃O₄-CoO_x	TBHP	−	80	12	100	68.4	21
Co-Mn-0.25	1 MPa O₂	2 equiv. NaHCO₃	120	5	99	95	22
Co-Mn-0.25	1 MPa O₂	2 equiv. NaHCO₃	90	5	64 ± 3.6	4.6 ± 1.8	22
MnO_x-CeO₂	2 MPa O₂	4 equiv. KHCO₃	110	12	97.9	79.6	31

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磁性MnO₂-Fe₃O₄复合氧化物催化5-羟甲基糠醛氧化合成2,5-呋喃二甲酸研究

doi: 10.1016/S1872-5813(21)60020-8

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Tel: 024-56863837，E-mail：jingyun.wang@lnpu.edu.cn

mingdong.zhou@lnpu.edu.cn

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Oxidation of 5-hydroxylmethylfurfural to 2, 5-furandicarboxylic acid catalyzed by magnetic MnO₂-Fe₃O₄ composite oxides

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