1H-吡咯-2,5-二酮(马来酰亚胺):油气地球化学中的新生物标志物

doi:10.7623/syxb201902005

石油学报 ›› 2019, Vol. 40 ›› Issue (2): 176-181.DOI: 10.7623/syxb201902005

1H-吡咯-2,5-二酮(马来酰亚胺):油气地球化学中的新生物标志物

王广利¹, 李婧仪¹, 师生宝¹, 常睿¹

1. 油气资源与探测国家重点实验室中国石油大学(北京)地球科学学院北京 102249;
2. GNS Science Lower Hutt PO Box 30-368

收稿日期:2018-05-03 修回日期:2018-12-09 出版日期:2019-02-25 发布日期:2019-03-05
通讯作者: 王广利,男,1973年12月生,1996年获山东工业大学学士学位,2006年获中国石油大学(北京)博士学位,现为中国石油大学(北京)副研究员,主要从事分子有机地球化学、油气形成与保存机制等领域的研究。Email:sydxwgl@cup.edu.cn
作者简介:王广利,男,1973年12月生,1996年获山东工业大学学士学位,2006年获中国石油大学(北京)博士学位,现为中国石油大学(北京)副研究员,主要从事分子有机地球化学、油气形成与保存机制等领域的研究。Email:sydxwgl@cup.edu.cn
基金资助:
中国—新西兰国际交流基金项目(17-GNS-002-CHN)和山东省沉积成矿作用与沉积矿产重点实验室开放基金项目(DMSM2017057)资助

1H-pyrrole-2,5-diones (maleimides):the novel biomarkers in petroleum geochemistry

Wang Guangli¹, Sebastian Naeher¹, Li Jingyi¹, Shi Shengbao¹

1. State Key Laboratory of Petroleum Resources and Prospecting, Beijing 102249, China;
College of Geosciences, China University of Petroleum, Beijing 102249, China;
2. GNS Science, 1 Fairway Drive, Avalon 5010, PO Box 30-368, Lower Hutt 5040, New Zealand

Received:2018-05-03 Revised:2018-12-09 Online:2019-02-25 Published:2019-03-05

摘要/Abstract

摘要：

1H-吡咯-2,5-二酮(马来酰亚胺)是发现于石油以及土壤、沉积物和沉积岩中四吡咯色素的降解产物或衍生物,其中2-甲基-3-正丙基(Me,n-Pr)和2-甲基-3-异丁基(Me,i-Bu)马来酰亚胺主要来源于光合硫细菌体内的细菌叶绿素。将不同来源和成因的石油中分离出马来酰亚胺组分,并运用气相色谱-质谱(GC-MS)和全二维气相色谱-飞行时间质谱(GC×GC-ToFMS)进行分析鉴定,结果表明,在中国湖相原油中发育3类不同系列的马来酰亚胺,且不同成因的原油中马来酰亚胺组成存在显著差别。丰富的Me,n-Pr和Me,i-Bu马来酰亚胺主要分布于咸化、水体存在永久性分层的渤海湾盆地沙河街组四段上部烃源岩生成的原油中,在微咸水或淡水条件下形成的原油中二者均不发育。同时,Me,n-Pr和Me,i-Bu马来酰亚胺可以有效地应用于判识透光滞水带(PZE)的出现和进行油源对比。马来酰亚胺有望成为油气地球化学中一类新的非烃类生物标志物。

关键词: 1H-吡咯-2, 5-二酮, 马来酰亚胺, 光合绿硫菌, 生物标志物, 沉积环境, 油源对比

Abstract:

1H-pyrrole-2,5-diones, or maleimides, are degradation products or derivatives from tetrapyrrole pigments found in petroleum, soils, sediments and sedimentary rocks; among them, 2-methyl-3-n-propyl (Me,n-Pr) and 2-methyl-3-isobutyl (Me,i-Bu) maleimide are mainly sourced from the bacteriochlorophylls of green phototrophic sulfur bacteria (Chlorobiaceae). In this study, the maleimides fractions were extracted from crude oil with mixed sources and geneses, and the gas chromatography-mass spectrometry (GC-MS) and comprehensive two-dimensional gas chromatography-time-of-flight mass spectrometry (GC×GC-ToFMS) were used for analysis and identification. The results show that three different sets of maleimides occur in China’s lacustrine oil, and there are significant differences in the maleimide components of mixed-genesis crude oil. Abundant Me,n-Pr and Me,i-Bu maleimides are mainly distributed in the crude oil derived from the upper source rocks in Member 4 of Shahejie Formation, Bohai Bay Basin with saline-water permanent stratification, while both are undeveloped in the crude oil under brackish or fresh water conditions. Meanwhile, Me,n-Pr and Me,i-Bu maleimides can be used to identify the occurrence of light-permeable stagnant water zone for oil-source correlations. Thus, maleimides are expected to become a new kind of biomarkers in hydrocarbon geochemistry.

Key words: 1H-pyrrole-2,5-dione, maleimide, Chlorobiaceae, biomarker, depositional environment, oil-source correlation

中图分类号:

TE122.1

王广利, 李婧仪, 师生宝, 常睿. 1H-吡咯-2,5-二酮(马来酰亚胺):油气地球化学中的新生物标志物[J]. 石油学报, 2019, 40(2): 176-181.

Wang Guangli, Sebastian Naeher, Li Jingyi, Shi Shengbao, Chang Rui. 1H-pyrrole-2,5-diones (maleimides):the novel biomarkers in petroleum geochemistry[J]. Acta Petrolei Sinica, 2019, 40(2): 176-181.

参考文献

[1] TREIBS A.Chlorophyll-und Hminderivate in organischen mineralstoffen[J].Angewandte Chemie,1936,49(38):682-686.
[2] HODGSON G W,PEAKE E.Metal chlorin complexes in recent sediments as initial precursors to petroleum porphyrin pigments[J].Nature,1961,191(4790):766-767.
[3] HODGSON G W,HITCHON B,TAGUCHI K,et al.Geochemistry of porphyrins,chlorins and polycyclic aromatics in soils,sediments and sedimentary rocks[J].Geochimica et Cosmochimica Acta,1968,32(7):737-772.
[4] EGLINTON G,SCOTT P M,BELSKY T,et al.Hydrocarbons of biological origin from a one-billion-year-old sediment[J].Science 1964,145(3629):263-264.
[5] 于志强,彭平安,盛国英,等.茂名与江汉第三系油页岩中生物标志物碳同位素研究[J].科学通报,2000,45(增刊1):2783-2789.
YU Zhiqiang,PENG Ping’an, SHENG Guoying,et al.The carbon isotope study of biomarkers in the Maoming and the Jianghan Tertiary oil shale[J].Chinese Science Bulletin, 2000,45(S1):90-96.
[6] WILSON M A,HODGSON D A,KEELY B J.Structural variations in derivatives of the bacteriochlorophylls of Chlorobiaceae:impact of stratigraphic resolution on depth profiles as revealed by methanolysis[J].Organic Geochemistry,2004,35(11/12):1299-1307.
[7] NAEHER S,SUGA H,OGAWA N O,et al.Compound-specific carbon and nitrogen isotopic compositions of chlorophyll a and its derivatives reveal the eutrophication history of Lake Zurich (Switzerland)[J].Chemical Geology,2016,443:210-219.
[8] NAEHER S,SUGA H,OGAWA N O,et al.Distributions and compound-specific isotopic signatures of sedimentary chlorins reflect the composition of photoautotrophic communities and their carbon and nitrogen sources in Swiss lakes and the Black Sea[J].Chemical Geology,2016,443:198-209.
[9] TISSOT B P,WELTE D H.Petroleum formation and occurrence[M].Berlin:Springer-Verlag,1984.
[10] KILLOPS S D,KILLOPS V J.Introduction to organic geochemistry[M].2nd ed.New York:Wiley-Blackwell Press,2005.
[11] PETERS K E,WALTERS C C,MOLDOWAN J M.The biomarker guide edition II[M].Cambridge:Cambridge University Press,2005.
[12] 陈建平,魏军,倪云燕,等.酒西坳陷原油地球化学特征与成熟度分类[J].石油学报,2018,39(5):491-503.
CHEN Jianping,WEI Jun,NI Yunyan,et al.Geochemical features and maturity classification of crude oil in the Jiuxi depression,Jiuquan Basin[J].Acta Petrolei Sinica ,2018,39(5):491-503.
[13] MARTIN J,QUIRKE E,SHAW G J,et al.Petroporphyrins:II:The presence of porphyrins with extended alkyl substituents[J].Tetrahedron,1980,36(22):3261-3267.
[14] NAEHER S,LENGGER S K,GRICE K.A new method for the rapid analysis of 1H-Pyrrole-2,5-diones (maleimides)in environmental samples by two-dimensional gas chromatography time-of-flight mass spectrometry[J].Journal of Chromatography A,2016,1435:125-135.
[15] GRICE K,GIBBISON R,ATKINSON J E,et al.Maleimides (1H-pyrrole-2,5-diones)as molecular indicators of anoxygenic photosynthesis in ancient water columns [J].Geochimica et Cosmochimica Acta,1996,60(20):3913-3924.
[16] GRICE K,SCHAEFFER P,SCHWARK L,et al.Changes in palaeoenvironmental conditions during deposition of the Permian Kupferschiefer (Lower Rhine Basin, northwest Germany)inferred from molecular and isotopic compositions of biomarker components[J].Organic Geochemistry,1997,26(11/12):677-690.
[17] NAEHER S,GRICE K.Novel 1H-Pyrrole-2,5-dione (maleimide)proxies for the assessment of photic zone Euxinia[J].Chemical Geology,2015,404:100-109.
[18] WANG Guangli,CHENG Bin,WANG T G,et al.Monoterpanes as molecular indicators to diagnose depositional environments for source rocks of crude oils and condensates[J].Organic Geochemistry,2014,72:59-68.
[19] WANG Guangli,XUE Yongchao,WANG Daowei,et al.Biodegradation and water washing within a series of petroleum reservoirs of the Panyu oil field[J].Organic Geochemistry,2016,96:65-76.
[20] 曾翔,蔡进功,董哲,等.泥页岩沉积特征与生烃能力——以东营凹陷沙河街组三段中亚段—沙河街组四段上亚段为例[J].石油学报,2017,38(1):31-43.
ZENG Xiang,CAI Jingong,DONG Zhe,et al.Sedimentary characteristics and hydrocarbon generation potential of mudstone and shale:a case study of Middle Submember of Member 3 and Upper Submember of Member 4 in Shahejie Formation in Dongying sag[J].Acta Petrolei Sinica,2017,38(1):31-43.
[21] WANG Guangli,SHI Shengbao,WANG Peirong,et al.Analysis of diamondoids in crude oils using comprehensive two-dimensional gas chromatography/time-of-flight mass spectrometry[J].Fuel,2013,107:706-714.
[22] 程斌,王培荣,王铁冠,等.原油单萜烃的分布及地球化学意义[J].石油学报,2015,36(11):1341-1348.
CHENG Bin,WANG Peirong,WANG Tieguan,et al.Occurrence and geochemical significance of monoterpenoid hydrocarbons in crude oils[J].Acta Petrolei Sinica,2015,36(11):1341-1348.
[23] CHENG Bin,WANG T G,HUANG Haiping,et al.Application of the monoterpane ratio (MTR)to distinguish marine oils from terrigenous oils and infer depositional environment in northern Tarim Basin,China[J].Organic Geochemistry,2015,85:1-10.
[24] WANG Guangli,SIMONEIT B R T,SHI Shengbao,et al.A GC× GC-ToFMS investigation of the unresolved complex mixture and associated biomarkers in biodegraded petroleum[J].Acta Geologica Sinica:English Edition,2018,92(5):1959-1972.
[25] 王广利,王铁冠,张林晔.济阳坳陷古近系湖相沉积的分子地层学[J].地球科学:中国地质大学学报,2008,33(3):371-376.
WANG Guangli,WANG Tieguan,ZHANG Linye.Molecular stratigraphy in the lacustrine Jiyang super depression of Eocene[J].Earth Science:Journal of China University of Geosciences,2008,33(3):371-376.
[26] DAMST J S S,KENIG F,KOOPMANS M P,et al.Evidence for gammacerane as an indicator of water column stratification[J].Geochimica et Cosmochimica Acta,1995,59(9):1895-1900.
[27] 张林晔,包友书,李钜源,等.湖相页岩油可动性——以渤海湾盆地济阳坳陷东营凹陷为例[J].石油勘探与开发,2014,41(6):641-649.
ZHANG Linye,BAO Youshu,LI Juyuan,et al.Movability of lacustrine shale oil:a case study of Dongying sag,Jiyang depression,Bohai Bay Basin[J].Petroleum Exploration and Development,2014,41(6):641-649.
[28] 张林晔,孔祥星,张春荣,等.济阳坳陷下第三系优质烃源岩的发育及其意义[J].地球化学,2003,32(1):35-42.
ZHANG Linye,KONG Xiangxing,ZHANG Chunrong,et al.High-quality oil-prone source rocks in Jiyang depression[J].Geochimica,2003,32(1):35-42.
[29] ZHANG Shuichang,LIANG Digang,GONG Zaisheng,et al.Geochemistry of petroleum systems in the eastern Pearl River Mouth Basin:evidence for mixed oils[J].Organic Geochemistry,2003,34(7):971-991.
[30] LI Maowen,ZHANG Shuichang,SNOWDON L,et al.Oil-source correlation in Tertiary deltaic petroleum systems:a comparative study of the Beaufort-Mackenzie Basin in Canada and the Pearl River Mouth Basin in China[J].Organic Geochemistry,2008,39(8):1170-1175.
[31] 王强,彭平安,张文正,等.鄂尔多斯盆地延长组7段页岩全组分定量生烃模拟及原油可动性评价[J].石油学报,2018,39(5):541-553.
WANG Qiang,PENG Ping’an,ZHANG Wenzheng,et al.Quantitative full-component hydrocarbon-generating simulation and crude oil mobility evaluation of shale in 7th Member of Yanchang Formation,Ordos Basin[J].Acta Petrolei Sinica,2018,39(5):541-553.

1H-吡咯-2,5-二酮(马来酰亚胺):油气地球化学中的新生物标志物

1H-pyrrole-2,5-diones (maleimides):the novel biomarkers in petroleum geochemistry

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