原油中咔唑类参数运移示踪效应的驱替模拟实验

赵守钰; 徐耀辉; 严刚; 韩欣; 刘保磊; 钟鸣; 李姗姗

doi:10.11781/sysydz202402402

原油中咔唑类参数运移示踪效应的驱替模拟实验

doi: 10.11781/sysydz202402402

赵守钰^1,,
徐耀辉^1, ,,
严刚¹,
韩欣²,
刘保磊³,
钟鸣⁴,
李姗姗¹

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.
中国石油长庆油田分公司长庆实业集团有限公司, 西安 710018
3.
长江大学油气钻采工程湖北省重点实验室, 武汉 430100
4.
中国地质大学(北京) 能源学院, 北京 100089

基金项目:

国家自然科学基金项目 41972122

详细信息

作者简介:
赵守钰(1998—)，男，硕士生，有机地球化学专业。E-mail: 2315326996@qq.com

通讯作者:
徐耀辉(1972—)，男，教授，博士生导师，从事有机地球化学和油气成藏研究。E-mail: yaohuixu@126.com

中图分类号: TE135
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- 被引次数: 0
出版历程
- 收稿日期: 2023-06-09
- 修回日期: 2024-02-01
- 刊出日期: 2024-03-28

Displacement simulation experiments of migration effect on carbazole parameters of crude oil

1.
Hubei Key Laboratory of Oil and Gas Geochemistry and Environment, College of Resources and Environment, Yangtze University, Wuhan, Hubei 430100, China
2.
Changqing Industrial Group Co., Ltd., PetroChina Changqing Oilfield Company, Xi'an, Shaanxi 710018, China
3.
Hubei Key Laboratory of Oil and Gas Drilling and Production Engineering, Yangtze University, Wuhan, Hubei 430100, China
4.
College of Energy and Resources, China University of Geosciences(Beijing), Beijing 100089, China

摘要

摘要: 油气运移研究对油气勘探与开发至关重要，受原油黏度、复杂化学组成及潜在的多种地质因素影响，原油运移方向与路径的确定难度较大。分子地球化学参数是研究油气运移规律的有效方法之一，实际成藏过程中的这些参数受其形成、相对组成以及演化程度等因素的影响。在实验室条件下可实现单一因素控制下的分子参数效应，采用室内驱替模拟实验的方法，在填砂管上进行油驱水实验，利用C₁₈固相萃取柱分离与富集不同运移距离吸附油中的咔唑类化合物，考察原油中咔唑类化合物的运移示踪规律。结果表明，咔唑类参数1-/4-MCA、1, 8-/1, 7-DMCA、1, 8-/2, 4-DMCA、1, 8-/2, 5-DMCA、1, 8-/2, 7-DMCA比值均随着运移距离的增加而显著增大，特别是全屏蔽型与全裸露型异构体比值1, 8-/2, 4-DMCA和1, 8-/2, 5-DMCA的增长幅度可达63.97%和35.50%，这些参数具备作为良好的运移示踪参数的潜质；而参数苯并[a]/[c]咔唑所表现出的运移示踪规律与前人部分实际油藏运移研究不符，可能是苯并咔唑类化合物的运移受其本身构型和其他地质条件的影响，建议该参数在应用到油气运移示踪研究时须谨慎使用。实验结果可为原油运移示踪参数研究提供有效的方法借鉴，但在实际地质应用时仍需结合分子动力学等手段对相关参数进行验证与优选。
- 咔唑类化合物 /
- 驱替模拟 /
- 地质色层分馏效应 /
- 原油运移
Abstract: The investigation of oil and gas migration plays a vital role in the field of oil and gas exploration and development. Determining the direction and path of crude oil migration is challenging due to factors such as crude oil viscosity, complex chemical composition, and geological influences. Molecular geochemical parameters are a valuable tool for studying petroleum migration, although they can be affected by factors like compound formation, distribution, and maturation. One approach involves simulating these parameters under controlled laboratory conditions to isolate their individual effects. This study establishes a sandy-packed system to simulate oil-driven experiments and uses a C₁₈ solid-phase extraction column to analyze carbazole compound fractions at different migration distances. The findings indicate that certain carbazole parameters, such as 1-/4-MCA, 1, 8-/1, 7-DMCA, 1, 8-/2, 4-DMCA, 1, 8-/2, 5-DMCA, and 1, 8-/2, 7-DMCA, increase significantly with transport distances. Notably, fully shielded and fully exposed isomers like 1, 8-/2, 4-DMCA and 1, 8-/2, 5-DMCA show enrichment levels of up to 63.97% and 35.50%, making them potential indicators of oil migration. However, parameters related to benzo [a]/[c] carbazole show inconsistencies with previous findings, likely due to intrinsic configurations and varying geological conditions that must be taken into account. The experimental results presented in this study offer insights for assessing specific reservoirs, with a recommendation to also consider molecular kinetics when selecting molecular parameters.
- carbazole compound /
- displacement simulation /
- geochromatographic effect /
- crude oil migration
注释:

利益冲突声明/Conflict of Interests

所有作者声明不存在利益冲突。

All authors disclose no relevant conflict of interests.

作者贡献/Authors’Contributions

赵守钰、徐耀辉、严刚参与论文框架设计及撰写工作；刘保磊、钟鸣参与实验设计；严刚完成实验操作；韩欣、李珊珊负责稿件校对。所有作者均阅读并同意最终稿件的提交。

The study was designed and the manuscript was drafted by ZHAO Shouyu, XU Yaohui and YAN Gang. The experiment was designed by LIU Baolei and ZHONG Ming. The experimental operation was made by YAN Gang. The proofreading of the manuscript was completed by HAN Xin and LI Shanshan. All the authors have read the last version of paper and consented for submission.

HTML全文

图 1 原油驱替模拟装置示意

Figure 1. Schematic diagram of crude oil displacement simulator

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图 2 咔唑、苯并[a]咔唑和二苯并咔唑的分子结构

Figure 2. Molecular structure of carbazole, benzo [a] carbazole and dibenzocarbazole

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图 3 原油驱替装置入口端吸附油中咔唑类化合物的质量色谱

图中峰号表示的化合物名称见表 1。

Figure 3. Mass chromatograms of carbazole compounds in adsorbed oil at inlet end of crude oil displacement simulator

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图 4 不同运移距离咔唑类化合物质量色谱

Figure 4. Mass chromatograms of carbazole compounds with different migration distances

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图 5 咔唑类运移参数随着距离的变化特征

Figure 5. Characteristics of variation of carbazole migration parameters with distance

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表 1 吸附油中咔唑化合物鉴定结果

Table 1. Identification results of carbazole compounds in adsorbed oil

峰号	分子式	化合物名称	英文名称(简写)	类型
1	C₁₂H₉N	咔唑	Carbazole(CA)	全裸露
2	C₁₃H₁₁N	1-甲基咔唑	1-Methylcarbazole(4-MCA)	半屏蔽
3	C₁₃H₁₁N	3-甲基咔唑	2-Methylcarbazole(2-MCA)	全裸露
4	C₁₃H₁₁N	2-甲基咔唑	3-Methylcarbazole(3-MCA)	全裸露
5	C₁₃H₁₁N	4-甲基咔唑	4-Methylcarbazole(4-MCA)	全裸露
6	C₁₄H₁₃N	1, 8-二甲基咔唑	1, 8-Dimethylcarbazole(1, 8-DMCA)	全屏蔽
7	C₁₄H₁₃N	1-乙基咔唑	1-Eethylcarbazole(1-ECA)	半屏蔽
8	C₁₄H₁₃N	1, 3-二甲基咔唑	1, 3-Dimethylcarbazole(1, 3-DMCA)	半屏蔽
9	C₁₄H₁₃N	1, 6-二甲基咔唑	1, 6-Dimethylcarbazole(1, 6-DMCA)	半屏蔽
10	C₁₄H₁₃N	1, 7-二甲基咔唑	1, 7-Dimethylcarbazole(1, 7-DMCA)	半屏蔽
11	C₁₄H₁₃N	1, 4-二甲基咔唑	1, 4-Dimethylcarbazole(1, 4-DMCA)	半屏蔽
11’	C₁₄H₁₃N	4-乙基咔唑	4-Eethylcarbazole(4-ECA)	全裸露
12	C₁₄H₁₃N	1, 5-二甲基咔唑	1, 5-Dimethylcarbazole(1, 5-DMCA)	半屏蔽
12’	C₁₄H₁₃N	3-乙基咔唑	3-Eethylcarbazole(3-ECA)	全裸露
13	C₁₄H₁₃N	2, 6-二甲基咔唑	2, 6-Dimethylcarbazole(2, 6-DMCA	全裸露
14	C₁₄H₁₃N	2, 7-二甲基咔唑	2, 7-Dimethylcarbazole(2, 7-DMCA)	全裸露
15	C₁₄H₁₃N	1, 2-二甲基咔唑	1, 2-Dimethylcarbazole(1, 2-DMCA)	半屏蔽
16	C₁₄H₁₃N	2, 4-二甲基咔唑	2, 4-Dimethylcarbazole(2, 4-DMCA)	全裸露
17	C₁₄H₁₃N	2, 5-二甲基咔唑	2, 5-Dimethylcarbazole(2, 5-DMCA)	全裸露
18	C₁₄H₁₃N	2, 3-二甲基咔唑	2, 3-Dimethylcarbazole(2, 3-DMCA)	全裸露
19	C₁₄H₁₃N	3, 4-二甲基咔唑	3, 4-Dimethylcarbazole(3, 4-DMCA)	全裸露
20	C₁₆H₁₁N	苯并[a]咔唑	Benzo[a]carbazole(BC[a])	未定
21	C₁₆H₁₁N	苯并[b]咔唑	Benzo[b]carbazole(BC[b])	未定
22	C₁₆H₁₁N	苯并[c]咔唑	Benzo[c]carbazole(BC[c])	未定
注：全裸露型指1和8号碳位上氢原子均未被烷基取代；半屏蔽型指1和8号碳位上只有一个氢原子被烷基取代；全屏蔽型指1和8号碳位上氢原子均被烷基取代。

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表 2 不同运移距离石英砂吸附油咔唑类化合物运移参数

Table 2. Migration parameters of carbazole compounds of quartz sand adsorbed oil at different migration distances

参数	运移距离
参数	0 cm	30 cm	60 cm	90 cm	120 cm
1-/4-MCA	1.32	1.60	1.68	1.61	1.74
1, 8-/1, 7-DMCA	11.35	11.92	13.00	13.75	13.77
1, 8-/2, 4-DMCA	8.27	8.44	9.19	12.13	13.56
1, 8-/2, 5-DMCA	12.28	14.30	15.09	15.73	16.64
1, 8-/2, 7-DMCA	3.23	3.07	3.47	3.49	3.85
[a]/[c]	0.54	0.57	0.61	0.59	0.64

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参考文献(49)

[1]	纪红, 陈湘飞. 油气运移地球化学示踪研究进展[J]. 广东石油化工学院学报, 2020, 30(6): 19-23. https://www.cnki.com.cn/Article/CJFDTOTAL-SHGD202006005.htm JI Hong, CHEN Xiangfei. An overview of recent progress in geoche-mical tracing of hydrocarbon migration[J]. Journal of Guangdong University of Petrochemical Technology, 2020, 30(6): 19-23. https://www.cnki.com.cn/Article/CJFDTOTAL-SHGD202006005.htm
[2]	ENGLAND W A, MACKENZIE A S, MANN D M, et al. The movement and entrapment of petroleum fluids in the subsurface[J]. Journal of the Geological Society, 1987, 144(2): 327-347. doi: 10.1144/gsjgs.144.2.0327
[3]	YAMAMOTO M. Fractionation of azaarenes during oil migration[J]. Organic Geochemistry, 1992, 19(4/6): 389-402.
[4]	李美俊, 王铁冠. 油藏地球化学在勘探中的研究进展及应用: 以北部湾盆地福山凹陷为例[J]. 地学前缘, 2015, 22(1): 215-222. https://www.cnki.com.cn/Article/CJFDTOTAL-DXQY201501021.htm LI Meijun, WANG Tieguan. The progress and application of reservoir geochemistry in hydrocarbon exploration: an example from the Fushan Depression, Beibuwan Basin, South China Sea[J]. Earth Science Frontiers, 2015, 22(1): 215-222. https://www.cnki.com.cn/Article/CJFDTOTAL-DXQY201501021.htm
[5]	LI M, LARTER S R, STODDART D, et al. Fractionation of pyrrolic nitrogen compounds in petroleum during migration: derivation of migration-related geochemical parameters[J]. Geological Society, London, Special Publications, 1995, 86: 103-123. doi: 10.1144/GSL.SP.1995.086.01.09
[6]	李多丽, 关平. 中国油气二次运移的研究现状及展望[J]. 北京大学学报(自然科学版), 2004, 40(4): 658-668. doi: 10.3321/j.issn:0479-8023.2004.04.023 LI Duoli, GUAN Ping. Research situation and prospect of hydrocarbon migration in China[J]. Acta Scientiarum Naturalium Universitatis Pekinensis, 2004, 40(4): 658-668. doi: 10.3321/j.issn:0479-8023.2004.04.023
[7]	乔锦琪, 刘洛夫, 尚晓庆, 等. 油气运移示踪应用及有效性分析: 以准噶尔盆地白家海凸起侏罗系八道湾组油气为例[J]. 矿物岩石地球化学通报, 2023, 42(1): 107-121. https://www.cnki.com.cn/Article/CJFDTOTAL-KYDH202301010.htm QIAO Jinqi, LIU Luofu, SHANG Xiaoqing, et al. Application and effectiveness analysis of the hydrocarbon-migration tracing: a case study of hydrocarbons from the Jurassic Badaowan Formation of the Baijiahai high in the Junggar Basin, China[J]. Bulletin of Mineralogy, Petrology and Geochemistry, 2023, 42(1): 107-121. https://www.cnki.com.cn/Article/CJFDTOTAL-KYDH202301010.htm
[8]	金之钧, 张发强. 油气运移研究现状及主要进展[J]. 石油与天然气地质, 2005, 26(3): 263-270. https://www.cnki.com.cn/Article/CJFDTOTAL-SYYT200503001.htm JIN Zhijun, ZHANG Faqiang. Status and major advancements in study of hydrocarbon migration[J]. Oil & Gas Geology, 2005, 26(3): 263-270. https://www.cnki.com.cn/Article/CJFDTOTAL-SYYT200503001.htm
[9]	STODDART D P, HALL P B, LARTER S R, et al. The reservoir geochemistry of the Eldfisk Field, Norwegian North Sea[J]. Geological Society, London, Special Publications, 1995, 86: 257-279. doi: 10.1144/GSL.SP.1995.086.01.15
[10]	CLEGG H, WILKES H, OLDENBURG T, et al. Influence of maturity on carbazole and benzocarbazole distributions in crude oils and source rocks from the Sonda de Campeche, Gulf of Mexico[J]. Organic Geochemistry, 1998, 29(1/3): 183-194.
[11]	LI Maowen, OSADETZ K G, YAO Huanxin, et al. Unusual crude oils in the Canadian Williston Basin, southeastern Saskatchewan[J]. Organic Geochemistry, 1998, 28(7/8): 477-488.
[12]	WANG Tieguan, LI Sumei, ZHANG Shuichang. Oil migration in the Lunnan region, Tarim Basin, China based on the pyrrolic nitrogen compound distribution[J]. Journal of Petroleum Science and Engineering, 2004, 41(1/3): 123-134.
[13]	刘洛夫, 徐新德. 含氮化合物与石油运移研究[J]. 勘探家, 1996, 1(2): 33-37. https://www.cnki.com.cn/Article/CJFDTOTAL-KTSY199602008.htm LIU Luofu, XU Xinde. Studies on nitrogen compounds and petroleum migration[J]. Explorationist, 1996, 1(2): 33-37. https://www.cnki.com.cn/Article/CJFDTOTAL-KTSY199602008.htm
[14]	李婧婧, 汤达祯, 杨永毅. 咔唑类化合物的运移示踪机理及应用[J]. 油气地质与采收率, 2008, 15(5): 38-41. https://www.cnki.com.cn/Article/CJFDTOTAL-YQCS200805013.htm LI Jingjing, TANG Dazhen, YANG Yongyi. Migration tracing mechanism of carbazole compounds and its application[J]. Petroleum Geology and Recovery Efficiency, 2008, 15(5): 38-41. https://www.cnki.com.cn/Article/CJFDTOTAL-YQCS200805013.htm
[15]	ZHANG Liuping, LI Maowen, WANG Yang, et al. A novel molecular index for secondary oil migration distance[J]. Scientific Reports, 2013, 3: 2487. doi: 10.1038/srep02487
[16]	张敏, 梅博文, 向廷生. 原油中的咔唑类化合物[J]. 科学通报, 1997, 42(22): 2411-2414. ZHANG Min, MEI Bowen, XIANG Tingsheng. Carbazolek-type compounds in crude oils[J]. Chinese Science Bulletin, 1998, 43(8): 669-672.
[17]	陈传平, 包建平, 朱翠山. 1-甲基咔唑的结构参数及其热稳定性[J]. 地质科技情报, 2006, 25(2): 57-59. https://www.cnki.com.cn/Article/CJFDTOTAL-DZKQ200602010.htm CHEN Chuanping, BAO Jianping, ZHU Cuishan. Molecular structural parameters and thermal stability of 1-methylcarbazole[J]. Bulletin of Geological Science and Technology, 2006, 25(2): 57-59. https://www.cnki.com.cn/Article/CJFDTOTAL-DZKQ200602010.htm
[18]	赵红静, 何保田, 尹太举, 等. 以中性含氮化合物的分馏作用确定低熟油运移路径[J]. 断块油气田, 2006, 13(4): 18-20. https://www.cnki.com.cn/Article/CJFDTOTAL-DKYT200604005.htm ZHAO Hongjing, HE Baotian, YIN Taiju, et al. Determining migration pathway of low maturity oil from fractional distillation of neutral nitrogen compounds[J]. Fault-Block Oil & Gas Field, 2006, 13(4): 18-20. https://www.cnki.com.cn/Article/CJFDTOTAL-DKYT200604005.htm
[19]	卢青, 包建平. 咔唑类化合物的地球化学意义及应用[J]. 广东石油化工学院学报, 2013, 23(6): 20-23. doi: 10.3969/j.issn.2095-2562.2013.06.006 LU Qing, BAO Jianping. The overview of research progress on carbazole compounds[J]. Journal of Guangdong University of Petrochemical Technology, 2013, 23(6): 20-23. doi: 10.3969/j.issn.2095-2562.2013.06.006
[20]	段毅, 孙涛, 吴保祥, 等. 鄂尔多斯盆地马岭油田延10油层组油气运移特征与机理[J]. 成都理工大学学报(自然科学版), 2009, 36(1): 1-7. https://www.cnki.com.cn/Article/CJFDTOTAL-CDLG200901001.htm DUAN Yi, SUN Tao, WU Baoxiang, et al. Characteristics and mecha-nism of migration of crude oil in Yan-10 subsection of the Yanan Formation of the Maling Oilfield in Ordos Basin, China[J]. Journal of Chengdu University of Technology (Science &. Technology Edition), 2009, 36(1): 1-7. https://www.cnki.com.cn/Article/CJFDTOTAL-CDLG200901001.htm
[21]	张亚和, 史权, 何俊辉, 等. 固相萃取法对原油中咔唑类含氮化合物的分离[J]. 分析测试学报, 2008, 27(S1): 252-255. https://cpfd.cnki.com.cn/Article/CPFDTOTAL-FXCS200811001094.htm ZHANG Yahe, SHI Quan, HE Junhui, et al. Separation and determination of carbazoles in crude oil by SPE/GC-MS method[J]. Journal of Instrumental Analysis, 2008, 27(S1): 252-255. https://cpfd.cnki.com.cn/Article/CPFDTOTAL-FXCS200811001094.htm
[22]	李素梅, 张爱云, 王铁冠, 等. 原油中吡咯类化合物的分离方法研究[J]. 石油实验地质, 1999, 21(3): 278-281. doi: 10.11781/sysydz199903278 LI Sumei, ZHANG Aiyun, WANG Tieguan, et al. Separation methods of pyrrolic compounds in crude oil[J]. Experimental Petroleum Geology, 1999, 21(3): 278-281. doi: 10.11781/sysydz199903278
[23]	包建平, 马安来. 原油中烷基苯酚和中性含氮化合物的快速分离与分析[J]. 江汉石油学院学报, 1998, 20(2): 1-5. https://www.cnki.com.cn/Article/CJFDTOTAL-JHSX802.000.htm BAO Jianping, MA Anlai. Rapid separation and analysis of phenols and neutral nitrogen compounds in crude oils[J]. Journal of Jianghan Petroleum Institute, 1998, 20(2): 1-5. https://www.cnki.com.cn/Article/CJFDTOTAL-JHSX802.000.htm
[24]	王汇彤, 徐冠军, 游建昌, 等. 原油中中性氮和烷基酚化合物的分离制备及分析应用[J]. 石油实验地质, 2003, 25(3): 310-313. doi: 10.11781/sysydz200303310 WANC Huitong, XU Guanjun, YOU Jianchang, et al. Separation and determination of neutral nitrogen compounds and alkylphenols in crude oil[J]. Petroleum Geology & Experiment, 2003, 25(3): 310-313. doi: 10.11781/sysydz200303310
[25]	张枝焕, 王铁冠, 吴水平, 等. 原油中部分吡咯类含氮化合物运移参数的适用性[J]. 成都理工大学学报(自然科学版), 2004, 31(2): 162-167. doi: 10.3969/j.issn.1671-9727.2004.02.010 ZHANG Zhihuan, WANG Tieguan, WU Shuiping, et al. Discussion on effects of pyrrolic nitrogen compound parameters on petroleum migration[J]. Journal of Chengdu University of Technology (Science & Technology Edition), 2004, 31(2): 162-167. doi: 10.3969/j.issn.1671-9727.2004.02.010
[26]	李素梅, 庞雄奇, 黎茂稳, 等. 低熟油、烃源岩中含氮化合物分布规律及其地球化学意义[J]. 地球化学, 2002, 31(1): 1-7. https://www.cnki.com.cn/Article/CJFDTOTAL-DQHX200201000.htm LI Sumei, PANG Xiongqi, LI Maowen, et al. Characteristics of pyrrolic nitrogen compounds and their geochemical significance in oils and rocks of Bamianhe Oilfield, Eastern China[J]. Geochimica, 2002, 31(1): 1-7. https://www.cnki.com.cn/Article/CJFDTOTAL-DQHX200201000.htm
[27]	李素梅, 张爱云, 王铁冠. 原油中吡咯类含氮化合物的分布型式[J]. 石油与天然气地质, 2000, 21(2): 118-122. https://www.cnki.com.cn/Article/CJFDTOTAL-SYYT200002005.htm LI Sumei, ZHANG Aiyun, WANG Tieguan. Distribution pattern of pyrrolic nitrogen compound in crude oils[J]. Oil & Gas Geo-logy, 2000, 21(2): 118-122. https://www.cnki.com.cn/Article/CJFDTOTAL-SYYT200002005.htm
[28]	黎茂稳. 油气二次运移研究的基本思路和几个应用实例[J]. 石油勘探与开发, 2000, 27(4): 11-19. https://www.cnki.com.cn/Article/CJFDTOTAL-SKYK200004003.htm LI Maowen. Quantification of petroleum secondary migration distances: fundamentals and case histories[J]. Petroleum Exploration and Development, 2000, 27(4): 11-19. https://www.cnki.com.cn/Article/CJFDTOTAL-SKYK200004003.htm
[29]	倪春华, 包建平, 张宝, 等. 吡咯类化合物及其在油气运移中的应用[J]. 新疆石油地质, 2005, 26(4): 428-431. https://www.cnki.com.cn/Article/CJFDTOTAL-XJSD200504028.htm NI Chunhua, BAO Jianping, ZHANG Bao, et al. Pyrrolic compounds and application in hydrocarbon migration[J]. Xinjiang Petroleum Geology, 2005, 26(4): 428-431. https://www.cnki.com.cn/Article/CJFDTOTAL-XJSD200504028.htm
[30]	LARTER S R, BOWLER B F J, LI M, et al. Molecular indicators of secondary oil migration distances[J]. Nature, 1996, 383(6601): 593-597. doi: 10.1038/383593a0
[31]	VAN DUIN A C T, LARTER S R. Application of molecular dynamics calculations in the prediction of dynamical molecular properties[J]. Organic Geochemistry, 1998, 29(5/7): 1043-1050.
[32]	杨禄, 李美俊, 刘晓强, 等. 甲基二苯并噻吩的吸附性及油藏充注途径示踪机理之Connolly分子表面计算证明[J]. 地球化学, 2017, 46(4): 367-372. doi: 10.3969/j.issn.0379-1726.2017.04.007 YANG Lu, LI Meijun, LIU Xiaoqiang, et al. Using connolly surface to characterize the adsorption of methyldibenzothiophenes, and their chemical mechanism as molecular tracer for oil filling pathways[J]. Geochimica, 2017, 46(4): 367-372. doi: 10.3969/j.issn.0379-1726.2017.04.007
[33]	LI Meijun, LIU Xiaoqiang, WANG Tieguan, et al. Fractionation of dibenzofurans during subsurface petroleum migration: based on molecular dynamics simulation and reservoir geochemistry[J]. Organic Geochemistry, 2018, 115: 220-232. doi: 10.1016/j.orggeochem.2017.10.006
[34]	HAN Qiuya, LI Meijun, LIU Xiaoqiang, et al. Fractionation of alkylated carbazoles in petroleum during subsurface migration: evidence from molecular simulation and application in sandstone reservoirs[J]. Journal of Petroleum Science and Engineering, 2020, 191: 107308. doi: 10.1016/j.petrol.2020.107308
[35]	李美俊, 刘晓强, 韩秋雅, 等. 分子模拟在油气地球化学中的应用研究进展[J]. 石油与天然气地质, 2021, 42(4): 919-930. https://www.cnki.com.cn/Article/CJFDTOTAL-SYYT202104014.htm LI Meijun, LIU Xiaoqiang, HAN Qiuya, et al. Progress of molecular simulation application research in petroleum geochemistry[J]. Oil & Gas Geology, 2021, 42(4): 919-930. https://www.cnki.com.cn/Article/CJFDTOTAL-SYYT202104014.htm
[36]	侯平, 周波, 罗晓容. 石油二次运移路径的模式分析[J]. 中国科学(D辑地球科学), 2004, 34(S1): 162-168. https://www.cnki.com.cn/Article/CJFDTOTAL-JDXK2004S1018.htm HOU Ping, ZHOU Bo, LUO Xiaorong. Pattern analysis of secondary oil migration path[J]. Science China(Earth Sciences), 2004, 34(S1): 162-168. https://www.cnki.com.cn/Article/CJFDTOTAL-JDXK2004S1018.htm
[37]	侯平, 罗晓容, 樊长江, 等. 石油二次运移不同模式条件下含油饱和度测量[J]. 石油与天然气地质, 2008, 29(4): 533-536. doi: 10.3321/j.issn:0253-9985.2008.04.018 HOU Ping, LUO Xiaorong, FAN Changjiang, et al. An experimental study of oil saturation in different secondary migration modes[J]. Oil & Gas Geology, 2008, 29(4): 533-536. doi: 10.3321/j.issn:0253-9985.2008.04.018
[38]	张利文, 李美俊, 杨福林. 二苯并呋喃地球化学研究进展及作为油藏充注示踪标志物的化学机理[J]. 石油与天然气地质, 2012, 33(4): 633-639. https://www.cnki.com.cn/Article/CJFDTOTAL-SYYT201204021.htm ZHANG Liwen, LI Meijun, YANG Fulin. Progress of geochemical research on dibenzofuran and its chemical mechanism as molecular tracer for oil charging pathways[J]. Oil & Gas Geology, 2012, 33(4): 633-639. https://www.cnki.com.cn/Article/CJFDTOTAL-SYYT201204021.htm
[39]	王传刚, 王铁冠, 谢明亮, 等. 运用吡咯类化合物分析彩南油田充注过程[J]. 新疆石油地质, 2004, 25(1): 61-64. doi: 10.3969/j.issn.1001-3873.2004.01.018 WANG Chuangang, WANC Tieguan, XIE Mingliang, et al. Application of pyrrolic compounds in analysis of hydrocarbon migration and recharging regularities in Cainan Oilfield, Junggar Basin[J]. Xinjiang Petroleum Geology, 2004, 25(1): 61-64. doi: 10.3969/j.issn.1001-3873.2004.01.018
[40]	魏彩云, 马行陟, 胡国艺, 等. 石油地质气相色谱及气相色谱-质谱实验室比对结果评价[J]. 石油实验地质, 2023, 45(3): 528-536. doi: 10.11781/sysydz202303528 WEI Caiyun, MA Xingzhi, HU Guoyi, et al. Evaluation of laboratory comparison results of GC and GC-MS in petroleum geology industry[J]. Petroleum Geology & Experiment, 2023, 45(3): 528-536. doi: 10.11781/sysydz202303528
[41]	王海华, 丁启光. 含氮化合物在东营凹陷南斜坡油气运移中的应用[J]. 山东科技大学学报(自然科学版), 2009, 28(2): 17-21. https://www.cnki.com.cn/Article/CJFDTOTAL-SDKY200902005.htm WANG Haihua, DING Qiguang. Application of nitrogen compounds in tracing hydrocarbon migration in south slope of Dongying Sag[J]. Journal of Shandong University of Science and Technology (Natural Science), 2009, 28(2): 17-21. https://www.cnki.com.cn/Article/CJFDTOTAL-SDKY200902005.htm
[42]	张富昌, 林承焰, 何金先, 等. 西峰油田延长组长8油层组油气运移特征研究[J]. 陕西科技大学学报, 2016, 34(5): 109-113. https://www.cnki.com.cn/Article/CJFDTOTAL-XBQG201605021.htm ZHANG Fuchang, LIN Chengyan, HE Jinxian, et al. Study on the migration of crude oil in Chang-8 subsection of the Yanchang Formation, Xifeng Oilfield[J]. Journal of Shaanxi University of Science & Technology, 2016, 34(5): 109-113. https://www.cnki.com.cn/Article/CJFDTOTAL-XBQG201605021.htm
[43]	邹伟. 含氮化合物在东濮凹陷西斜坡油气运移研究中的应用[J]. 石油天然气学报, 2005, 27(3): 284-288. https://www.cnki.com.cn/Article/CJFDTOTAL-JHSX200503003.htm ZOU Wei. Application of nitrogen compounds in tracing hydrocarbon migration in the west slope belt of Dongpu Sag[J]. Journal of Jianghan Petroleum Institute, 2005, 27(3): 284-288. https://www.cnki.com.cn/Article/CJFDTOTAL-JHSX200503003.htm
[44]	吴旗, 包建平, 朱翠山. 利用含氮化合物研究卞闵杨地区油气运移[J]. 石油天然气学报, 2014, 36(4): 21-25. https://www.cnki.com.cn/Article/CJFDTOTAL-JHSX201404004.htm WU Qi, BAO Jianping, ZHU Cuishan. Study of oil-gas migration in Bianminyang area by using nitrogenous compounds[J]. Journal of oil and Gas Technology, 2014, 36(4): 21-25. https://www.cnki.com.cn/Article/CJFDTOTAL-JHSX201404004.htm
[45]	薛楠, 吕修祥, 朱光有, 等. 油气成藏定位研究进展[J]. 天然气地球科学, 2022, 33(1): 63-77. https://www.cnki.com.cn/Article/CJFDTOTAL-TDKX202201006.htm XUE Nan, LYU Xiuxiang, ZHU Guangyou, et al. Research progress of oil and gas reservoir positioning[J]. Natural Gas Geoscience, 2022, 33(1): 63-77. https://www.cnki.com.cn/Article/CJFDTOTAL-TDKX202201006.htm
[46]	刘洛夫, 霍红, 李超, 等. 利用咔唑类化合物研究油气的运移: 以塔里木盆地环阿瓦提凹陷志留系古油藏为例[J]. 石油实验地质, 2006, 28(4): 366-369. doi: 10.11781/sysydz200604366 LIU Luofu, HUO Hong, LI Chao, et al. Study of petroleum migration of the Silurian ancient pools around Awati Sag in the Tarim Basin using carbazole compounds[J]. Petroleum Geology & Experiment, 2006, 28(4): 366-369. doi: 10.11781/sysydz200604366
[47]	刘俊海, 陈小宏, 杨香华, 等. 胡庆油田湖相原油咔唑类化合物的地球化学特征[J]. 沉积学报, 2006, 24(1): 123-128. https://www.cnki.com.cn/Article/CJFDTOTAL-CJXB200601015.htm LIU Junhai, CHEN Xiaohong, YANG Xianghua, et al. Geochemical characteristics of carbazole compounds in lacustrine oils in Huqing Oilfield[J]. Acta Sedimentologica Sinica, 2006, 24(1): 123-128. https://www.cnki.com.cn/Article/CJFDTOTAL-CJXB200601015.htm
[48]	刘俊海, 杨香华. 原油中吡咯类含氮化合物运移参数的适用性[J]. 西南石油大学学报(自然科学版), 2008, 30(4): 155-158. https://www.cnki.com.cn/Article/CJFDTOTAL-XNSY200804043.htm LIU Junhai, YANG Xianghua. Applicability of pyrrolic nitrogen compound migration parameter in crude oil[J]. Journal of Southwest Petroleum University (Science & Technology Edition), 2008, 30(4): 155-158. https://www.cnki.com.cn/Article/CJFDTOTAL-XNSY200804043.htm
[49]	黄海平, 任芳祥, LARTER S R. 生物降解作用对原油中苯并咔唑分布的影响[J]. 科学通报, 2002, 47(16): 1271-1275. HUANG Haiping, REN Fangxiang, LARTER S R. Influence of biodegradation on benzocarbazole distributions in reservoired oils[J]. Chinese Science Bulletin, 2002, 47(20): 1734-1739.