原油中芳烃化合物的柱层析与银离子薄层色谱分离方法对比研究

王霆; 宋浩; 王瑞林; 文志刚; 何文祥; 何家豪; 何长荣; 李洪波

doi:10.11781/sysydz202303549

原油中芳烃化合物的柱层析与银离子薄层色谱分离方法对比研究

doi: 10.11781/sysydz202303549

1.
长江大学资源与环境学院油气地球化学与环境湖北省重点实验室, 武汉 430100
2.
有机地球化学国家重点实验室, 广州 510640

基金项目:

国家自然科学基金 41872144

国家自然科学基金 42272160

详细信息

作者简介:
王霆(1984—)，男，博士，副教授，从事地球化学方面的教学与研究工作。E-mail: tw@yangtzeu.edu.cn

中图分类号: TE135
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出版历程
- 收稿日期: 2022-10-25
- 修回日期: 2023-04-17
- 刊出日期: 2023-05-28

Comparison of column chromatography and Ag⁺-thin layer chromatography for aromatic compounds in crude oil

1.
Hubei Key Laboratory of Petroleum Geochemistry and Environment, College of Resources and Environment, Yangtze University, Wuhan, Hubei 430100, China
2.
State Key Laboratory of Organic Geochemistry, Guangzhou, Guangdong 510640, China

摘要

摘要: 对比研究银离子薄层色谱法(Ag⁺-TLC)和柱层析法对原油中不同环数芳烃的分离效果与适用范围，旨在为后续有机地球化学研究中芳烃定量分析和单体烃同位素测试提供理论支撑。银离子薄层色谱法可以更好地富集单环芳烃，并将不同异构体的单环芳烃差异化富集于不同的组分中，但对多环芳烃的富集程度较低，损失严重，且易引入杂峰干扰；而柱层析法对双环和多环芳烃化合物具有更好的分离效果。银离子薄层色谱法适用于单环芳烃的精细分离，可用于富集烷基苯和芳基类异戊二烯系列化合物，并满足测定其单体烃同位素的检测要求；而柱层析法则能较好地富集萘、菲和三芳甾烷等系列化合物，并达到了测定单体烃同位素的分离度要求。
- 柱层析法 /
- 银离子薄层色谱法 /
- 芳烃 /
- 原油
Abstract: By comparing the separation effects and applicability of Ag⁺-thin layer chromatography (Ag⁺-TLC) and column chromatography on aromatic hydrocarbons with different ring numbers in crude oil, this article aims to provide theoretical support for the quantitative analysis of aromatics and isotope analysis of monomer hydrocarbon in organic geochemical research. The results showed that Ag⁺-TLC can better enrich monocyclic aromatics and differentiate the monocyclic aromatics of different isomers into different components, but has a poor effect in enriching palycyclic aromatics, which may lead to severe losses and possible peak interference. Column chromatography has better separation effects on dinuclear and polycyclic aromatic compounds. Therefore, Ag⁺-TLC, suitable for the fine separation of monocyclic aromatics, can be used to enrich alkylbenzenes and aryl isoprenoids, and meets the detection requirements for measuring their monomer hydrocarbon isotopes; while column chromatography can effectively enrich series of compounds such as naphthalene, phenanthrene, and triaromatic steroids, and meets the requirements for detecting the separating degree of monomeric hydrocarbon isotopes.
- column chromatography /
- Ag⁺-thin layer chromatography (Ag⁺-TLC) /
- aromatics /
- crude oil

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图 1 银离子薄层色谱法示意

Figure 1. Schematic diagram of Ag⁺-thin layer chromatography

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图 2 分离前后芳烃组分的TIC对比

C₁-萘.甲基萘；C₂-萘.二甲基萘和乙基萘；C₃-萘.三甲基萘、1-乙基-2-甲基萘和1-甲基-2-乙基萘；C₄-萘.四甲基萘、二甲基-乙基萘、乙基-二甲基萘和二乙基萘；UCM.未分辨复杂化合物；o-烷基甲苯.对位取代烷基甲苯；m-烷基甲苯.间位取代烷基甲苯；n-烷基苯.苯环上仅含1个烷基取代基；1-M-3-PyB.1-甲基-3-植烷苯；C₁-DBT.甲基取代二苯并噻吩；C₂-DBT.C₂烷基取代二苯并噻吩；C₃-DBT.C₃烷基取代二苯并噻吩；C₁-菲.甲基菲；C₂-菲.C₂烷基取代菲；C₃-菲.C₃烷基取代菲

Figure 2. Total ion chromatography (TIC) of aromatic components before and after separation

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图 3 Ag⁺-TLC法与柱层析法分离组分的m/z 106对比

1-M-3-PyB为1-甲基-3-植烷苯；o-烷基甲苯表示对位取代烷基甲苯；m-烷基甲苯表示间位取代烷基甲苯

Figure 3. Comparison of m/z 106 of components separated by Ag⁺-TLC and column chromatography

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图 4 Ag⁺-TLC法与柱层析法分离组分的m/z 133对比

2, 3, 6-AIP.2, 3, 6-三甲基芳基类异戊二烯烃；2, 3, 4-AIP.2, 3, 4-三甲基芳基类异戊二烯烃芳基类异戊二烯烃的鉴定根据参考文献[37]与质谱特征核对

Figure 4. Comparison of m/z 133 of components separated by Ag⁺-TLC and column chromatography

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图 5 Ag⁺-TLC法与柱层析法分离组分的m/z 128+142+156+170+184对比

C₁-萘.甲基萘；C₂-萘.二甲基萘和乙基萘；C₃-萘.三甲基萘、1-乙基-2-甲基萘和1-甲基-2-乙基萘；C₄-萘.四甲基萘、二甲基-乙基萘、乙基-二甲基萘和二乙基萘

Figure 5. Comparison of m/z 128+142+156+170+184 of components separated by Ag⁺-TLC and column chromatography

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图 6 Ag⁺-TLC法与柱层析法分离组分的m/z 198+212+226对比

C₁-二苯并噻吩表示C₁烷基取代二苯并噻吩；C₂-二苯并噻吩表示C₂烷基取代二苯并噻吩；C₃-二苯并噻吩表示C₃烷基取代二苯并噻吩

Figure 6. Comparison of m/z 198+212+226 of components separated by Ag⁺-TLC and column chromatography

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图 7 Ag⁺-TLC法与柱层析法分离组分的m/z 178+192+206+220对比

C₁-菲表示C₁烷基取代菲；C₂-菲表示C₂烷基取代菲；C₃-菲表示C₃烷基取代菲

Figure 7. Comparison of m/z 178+192+206+220 of components separated by Ag⁺- TLC and column chromatography

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图 8 Ag⁺-TLC法与柱层析法分离组分的m/z 231对比

Figure 8. Comparison of m/z 231 of components separated by Ag⁺- TLC and column chromatography

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