Research progress of platinum-based catalysts for hydrogenation of aromatic nitro compounds

doi:10.11949/0438-1157.20250401

Abstract

Abstract:

Aromatic amines are important raw materials in the chemical industry, widely used as intermediates for dyes, fragrances, synthetic pharmaceuticals, rubber, pesticides, and other fine chemicals. Catalytic hydrogenation of aromatic nitro compounds is a common method for the preparation of aromatic amines. Pt-based catalysts are widely used in the hydrogenation process of aromatic nitro compounds due to their high hydrogen dissociation ability. The size of Pt sites can affect their electronic state, coordination environment, metal-support interactions, etc., thereby influencing catalytic activity. This article elaborates on the research progress of Pt-based catalysts in the hydrogenation of aromatic nitro compounds from the perspective of active metal size. It also reviews the influence of Pt size effects on the hydrogenation performance of aromatic nitro compounds and provides prospects for future research on Pt-based catalysts.

Key words: aromatic nitro compounds, catalytic hydrogenation, platinum-based catalyst, size effect

摘要：

芳胺类化合物是化学工业中的重要原料，广泛用作染料、香料、合成医药、橡胶、杀虫剂和其他精细化学品的中间体。催化芳香硝基化合物加氢是制备芳胺类化合物的一种常用方法。Pt基催化剂因具有较高的氢解离能力而广泛应用于芳香硝基化合物的加氢过程，Pt位点尺寸可以影响其电子态、配位环境、金属-载体相互作用等，进而影响催化活性。从活性金属尺寸的角度阐述了Pt基催化剂在芳香硝基化合物加氢中的研究进展，综述了Pt尺寸效应对芳香硝基化合物加氢性能的影响规律，并对Pt基催化剂的未来研究方向进行了展望。

关键词: 芳香硝基化合物, 催化加氢, Pt基催化剂, 尺寸效应

CLC Number:

TQ 426.8

Kainan XIE, Zhirong FU, Yu HAN, Xin ZHANG, Yihao CHEN, Baoju WANG, Yong LUO. Research progress of platinum-based catalysts for hydrogenation of aromatic nitro compounds[J]. CIESC Journal, 2025, 76(12): 6134-6150.

谢凯南, 付芝蓉, 韩宇, 张鑫, 陈奕好, 王保举, 罗勇. Pt基催化剂在芳香硝基化合物加氢中的研究进展[J]. 化工学报, 2025, 76(12): 6134-6150.

Figures/Tables 10

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类型	催化剂	粒径/nm	反应	反应条件	转化率/%	选择性/%	TON/h^-1	文献
单原子型	Pt₁/h-NC	单原子	3-硝基苯乙烯→3-乙烯基苯胺	40℃、5 bar	97.1	77.8	31157	[18]
	Pt-PMA/AC	单原子	硝基苯→苯胺	25℃、10 bar	—	100	800	[20]
	0.08%Pt/FeO _x -R200	单原子	3-硝基苯乙烯→3-乙烯基苯胺	40℃、3 bar	95.6	98.4	1494	[25]
	Pt₁/PO₄-CeO₂	单原子	硝基苯→苯胺	60℃、1 bar	—	100	273	[26]
	Pt₁/C12A7	单原子	4-硝基苯→4-氯苯胺	60℃、5 bar	—	>99	25772	[32]
	Pt₁/Ni	单原子	3-硝基苯乙烯→3-乙烯基苯胺	40℃、3 bar	—	>99	1800	[16]
原子簇型	Pt₂/mpg-C₃N₄	双原子	硝基苯→苯胺	100℃、10 bar	>99	100	—	[33]
	Pt _n /ND@G	0.2~0.5	2,4-二硝基甲苯→2,4-二氨基甲苯	25℃、10 bar	100	>99	40647	[34]
	Pt-Ni-Co	单原子与原子簇组合	硝基苯→苯胺	≤40℃、10 bar	100	100	—	[35]
	Pt/CeO₂-300	<1	5-硝基苯并噻唑→5-氨基苯并噻唑	80℃、20 bar	约95	>99	—	[36]

类型	催化剂	粒径/nm	反应	反应条件	转化率/%	选择性/%	TON/h^-1	文献
单原子型	Pt₁/h-NC	单原子	3-硝基苯乙烯→3-乙烯基苯胺	40℃、5 bar	97.1	77.8	31157	[18]
	Pt-PMA/AC	单原子	硝基苯→苯胺	25℃、10 bar	—	100	800	[20]
	0.08%Pt/FeO _x -R200	单原子	3-硝基苯乙烯→3-乙烯基苯胺	40℃、3 bar	95.6	98.4	1494	[25]
	Pt₁/PO₄-CeO₂	单原子	硝基苯→苯胺	60℃、1 bar	—	100	273	[26]
	Pt₁/C12A7	单原子	4-硝基苯→4-氯苯胺	60℃、5 bar	—	>99	25772	[32]
	Pt₁/Ni	单原子	3-硝基苯乙烯→3-乙烯基苯胺	40℃、3 bar	—	>99	1800	[16]
原子簇型	Pt₂/mpg-C₃N₄	双原子	硝基苯→苯胺	100℃、10 bar	>99	100	—	[33]
	Pt _n /ND@G	0.2~0.5	2,4-二硝基甲苯→2,4-二氨基甲苯	25℃、10 bar	100	>99	40647	[34]
	Pt-Ni-Co	单原子与原子簇组合	硝基苯→苯胺	≤40℃、10 bar	100	100	—	[35]
	Pt/CeO₂-300	<1	5-硝基苯并噻唑→5-氨基苯并噻唑	80℃、20 bar	约95	>99	—	[36]

类型		催化剂	粒径/nm	反应	反应条件	转化率/%	选择性/%	TON/h^-1	文献
负载型	碳材料	Pt/ACH-450	2.5~3.2	3-硝基苯乙烯→3-乙烯基苯胺	100℃、40 bar	91.0	96.0	60	[47]
		Pt/RGO_-EG	3.1±0.4	硝基苯→苯胺	0℃、10 bar	94.3	100	—	[54]
		Pt/CNT	2.8±0.8	3,4-二氯硝基苯→ 3,4-二氯苯胺	30℃、10 bar	95.9	96.9	30960	[56]
	金属氧化物	0.08%（质量分数）Pt/TiO₂‘red.’	1.2~1.6	3-硝基苯乙烯→ 3-乙烯基苯胺	40℃、30 bar	—	>90	2000	[63]
		Pt/CeO₂	1.3~1.8	硝基苯→苯胺	25℃、10 bar	—	>99	—	[67]
		Pt/γ-Fe₂O₃	2.6	邻溴硝基苯→邻溴苯胺	30℃、20 bar	—	>99.9	—	[68]
		Pt_n/Al	约3	邻溴硝基苯→邻溴苯胺	60℃、8 bar	100	92.0	3700	[69]
包埋型		UiO-66-NH₂@Pt@PCN-222	约2.8	对硝基甲苯→对甲苯胺→β-酮烯胺	60℃、1 bar	>99	98.0	—	[74]
		UiO-66-NH₂@Pt@mSiO₂	2.5~3	硝基苯→苯胺→亚胺→N-苄基苯胺	25℃、1 bar	>99	92.4	—	[75]
		Pt@MFI	约3	4-硝基苯乙烯→4-氨基苯乙烯	80℃、10 bar	100	80.0	—	[76]
其他体系		Pt-Ⅱ（乙二醇还原制备）	1.7±0.4	邻氯硝基苯→邻氯苯胺	60℃、40 bar	—	>99.1	6639	[77]
		Pt@sc-PLA-PEG	1.4±0.3	2-氯硝基苯→2-氯苯胺	30℃、5 bar	—	>99.4	7161	[82]
		PtNCs/CS-GA	2.2	4-硝基苯酚→4-氨基苯酚	22℃	96.4	—	0.3	[94]
		0.4% Pt/FeNi-LDHs	—	2-氯硝基苯→2-氯苯胺	60℃、30 bar	—	100	1107.2	[95]

类型		催化剂	粒径/nm	反应	反应条件	转化率/%	选择性/%	TON/h^-1	文献
负载型	碳材料	Pt/ACH-450	2.5~3.2	3-硝基苯乙烯→3-乙烯基苯胺	100℃、40 bar	91.0	96.0	60	[47]
		Pt/RGO_-EG	3.1±0.4	硝基苯→苯胺	0℃、10 bar	94.3	100	—	[54]
		Pt/CNT	2.8±0.8	3,4-二氯硝基苯→ 3,4-二氯苯胺	30℃、10 bar	95.9	96.9	30960	[56]
	金属氧化物	0.08%（质量分数）Pt/TiO₂‘red.’	1.2~1.6	3-硝基苯乙烯→ 3-乙烯基苯胺	40℃、30 bar	—	>90	2000	[63]
		Pt/CeO₂	1.3~1.8	硝基苯→苯胺	25℃、10 bar	—	>99	—	[67]
		Pt/γ-Fe₂O₃	2.6	邻溴硝基苯→邻溴苯胺	30℃、20 bar	—	>99.9	—	[68]
		Pt_n/Al	约3	邻溴硝基苯→邻溴苯胺	60℃、8 bar	100	92.0	3700	[69]
包埋型		UiO-66-NH₂@Pt@PCN-222	约2.8	对硝基甲苯→对甲苯胺→β-酮烯胺	60℃、1 bar	>99	98.0	—	[74]
		UiO-66-NH₂@Pt@mSiO₂	2.5~3	硝基苯→苯胺→亚胺→N-苄基苯胺	25℃、1 bar	>99	92.4	—	[75]
		Pt@MFI	约3	4-硝基苯乙烯→4-氨基苯乙烯	80℃、10 bar	100	80.0	—	[76]
其他体系		Pt-Ⅱ（乙二醇还原制备）	1.7±0.4	邻氯硝基苯→邻氯苯胺	60℃、40 bar	—	>99.1	6639	[77]
		Pt@sc-PLA-PEG	1.4±0.3	2-氯硝基苯→2-氯苯胺	30℃、5 bar	—	>99.4	7161	[82]
		PtNCs/CS-GA	2.2	4-硝基苯酚→4-氨基苯酚	22℃	96.4	—	0.3	[94]
		0.4% Pt/FeNi-LDHs	—	2-氯硝基苯→2-氯苯胺	60℃、30 bar	—	100	1107.2	[95]

类型	催化剂	粒径/nm	反应	反应条件	转化率/%	选择性/%	TON/h^-1	文献
单金属纳米颗粒	Pt/C	约3	间二硝基苯→间硝基苯胺	10℃、1 bar	100	92.3	—	[96]
	Pt/TiO₂	—	3-硝基苯乙烯→3-乙烯基苯胺	120℃、9 bar	>98	96.0	—	[97]
	0.3%Pt/TiO₂	4.0	3-硝基苯乙酮加氢→3-氨基苯乙酮	30℃、10 bar	100	100	—	[98]
	Pt/TiO₂-200	3.6	5-硝基苯并噻唑→5-氨基苯并噻唑	80℃、40 bar	约99	>99	363	[99]
	0.9% Pt-CeO₂	2~5	对硝基苯酚→对氨基苯酚	25℃、15 bar	100	99.0	—	[100]
	Pt/C@g-C₃N₄	5~10	硝基苯→4-氨基苯酚	75℃、10 bar	100	99.0	—	[102]
多金属纳米颗粒	PtCo nanoflower	约10	硝基苯→苯胺	25℃、1 bar	99.9	100.0	—	[107]
	Pt-SnO₂/Al₂O₃	3.2±0.4	邻氯硝基苯→邻氯苯胺	45℃、1 bar	100	94.1	—	[108]
	Pt-Zn/HPS（Pt/Zn=0.5）	4.7±1.0	3-硝基苯乙烯→3-乙烯基苯胺	75℃、10 bar	100	97.0	—	[109]
	PVP-Pt/Ru（Pt/Ru=1∶4）	约3	邻氯硝基苯→邻氯苯胺	25℃、1 bar	100	99.0	—	[110]
	Pd@Pt-1/0.25/Al₂O₃	6.1±0.7	对氯硝基苯→对氯苯胺	45℃、1 bar	98.5	82.1	—	[111]
	AuPt/γ-Al₂O₃	3.89~6.02	对氯硝基苯→对氯苯胺	45℃、1 bar	95.3	99.3	—	[112]
			对硝基苯甲醚→对氨基苯甲醚		99.0	100	—
			邻硝基苯乙酮→邻氨基苯乙酮		97.5	100	—
	PtRuCoCuNi/CNFs	约26	对氯硝基苯→对氯苯胺	25℃、1 bar	100	100	—	[114]