超分子化学在本科实验中的运用——六元瓜环对氨基苯酚同分异构体的新型分离方法

doi:10.3866/PKU.DXHX202210088

Abstract

Abstract:

Based on the research-oriented laboratory teaching concept of "thick foundation, wide professional, and comprehensive", this paper combines the theoretical knowledge of supramolecular chemistry and macrocyclic chemistry to design a new comprehensive experiment of selective gradient separation of o-, m-, p-aminophenol isomers with the purity of 91.46%, 94.16% and 96.70%, respectively, based on supramolecular self-assembly using cucurbit^[6]uril as the host. All reagents can be recycled after the experiment, fully embodying the concept of green chemistry. This experiment involves TLC, LC, IR, and other important analytical methods to monitor the separation process, purity analysis, and structural characterization of the target product, which enables students to fully master basic theoretical knowledge, experimental principles, and learn to analyze experimental phenomena, thereby improving students' research-oriented literacy and ability to comprehensively apply knowledge.

Key words: Cucurbit[n]uril, Aminophenol, Isomeride, Separation method, Comprehensive experiment

Wenhao Lin, Ming Liu, Maoxia Yang, Jiayi Zhang, Chenghui Wang, Xin Xiao. Application of Supramolecular Chemistry in Undergraduate Laboratory: A New Method for Separation of Aminophenol Isomers by Cucurbit[6]uril[J].University Chemistry, 2023, 38(4): 260-268.

Figures/Tables 15

References 20

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试剂名称	结构式	CAS号	纯度	品牌
对氨基苯酚		123-30-8	99%	上海阿拉丁生化科技股份有限公司
间氨基苯酚		591-27-5	99%	上海阿拉丁生化科技股份有限公司
邻氨基苯酚		95-55-6	99%	上海阿拉丁生化科技股份有限公司
六元瓜环		80262-44-8	98%	上海纳孚生物科技有限公司
乙酸乙酯	CH₃COOCH₂CH₃	141-78-6	分析纯	上海易恩化学技术有限公司
无水乙醇	CH₃CH₂OH	64-17-5	分析纯(≥ 99.7%)	重庆川东化工(集团)有限公司

仪器名称	型号	制造商
液相色谱仪	Shimadzu LC-20AT	上海岛津
傅里叶变换红外光谱仪	VERTEX 70v	德国Bruker
电子天平	BSM-120.4电子天平	上海卓精
超声波清洗器	KQ5200B	昆山舒美
旋转蒸发器	XD-52AA	上海贤德
循环水式真空泵	SHZ-D(Ⅲ)	巩义予华

同分异构体	保留时间(min)	峰面积(× 10⁵)	浓度(× 10⁻³ mol∙L⁻¹)	分离效率(%)
间氨基苯酚	6.05	13. 34	23.67	94.68
对氨基苯酚	6.75	0.53	1.32	5.28
邻氨基苯酚	9.14	10. 03	23.95	95.80

同分异构体	保留时间(min)	峰面积(× 10⁵)	浓度(× 10⁻³ mol∙L⁻¹)	分离效率(%)	分离纯度(%)
间氨基苯酚	6.05	0.20	0.37	1.48	1.52
对氨基苯酚	6.75	5. 98	23.47	93.87	96.70
邻氨基苯酚	9.14	0.12	0.43	1.72	1.77

同分异构体	保留时间(min)	峰面积(× 10⁵)	浓度(× 10⁻³ mol∙L⁻¹)	分离效率(%)	分离纯度(%)
间氨基苯酚	6.05	0.94	1.69	6.76	6.81
对氨基苯酚	6.75	0.31	0.43	1.72	1.73
邻氨基苯酚	9.14	9.50	22. 71	90.85	91.46

Application of Supramolecular Chemistry in Undergraduate Laboratory: A New Method for Separation of Aminophenol Isomers by Cucurbit[6]uril

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