Advanced Search
Volume 45 Issue 2
Mar.  2023
Turn off MathJax
Article Contents
Article Navigation >  PETROLEUM GEOLOGY & EXPERIMENT  > 2023  >  45(2): 327-337
YU Xiao, MA Anlai, LI Xianqing, ZHU Xiuxiang, FEI Jianwei. GC×GC-TOFMS analysis of ethanodiamondoids in Ordovician oil from well SN1, Tarim Basin[J]. PETROLEUM GEOLOGY & EXPERIMENT, 2023, 45(2): 327-337. doi: 10.11781/sysydz202302327
Citation: YU Xiao, MA Anlai, LI Xianqing, ZHU Xiuxiang, FEI Jianwei. GC×GC-TOFMS analysis of ethanodiamondoids in Ordovician oil from well SN1, Tarim Basin[J]. PETROLEUM GEOLOGY & EXPERIMENT, 2023, 45(2): 327-337. doi: 10.11781/sysydz202302327
shu

GC×GC-TOFMS analysis of ethanodiamondoids in Ordovician oil from well SN1, Tarim Basin

doi: 10.11781/sysydz202302327
  • 1.

    State Key Laboratory of Coal Resources and Safe Mining, China University of Mining and Technology (Beijing), Beijing 100083, China

  • 2.

    College of Geoscience and Surveying Engineering, China University of Mining and Technology (Beijing), Beijing 100083, China

  • 3.

    SINOPEC Petroleum Exploration and Production Research Institute, Beijing 102206, China

  • 4.

    SINOPEC Northwest Oilfield Company, Urumqi, Xinjiang 830060, China

  • Received Date: 2022-06-08
  • Rev Recd Date: 2023-01-17
  • Publish Date: 2023-03-28
    Abstract
  • By 2D gas chromatography and time-of-flight mass spectrometry (GC×GC-TOFMS), 81 ethanodiamondoids with 1-3 cages were detected quantitatively in Ordovician crude oil from well SN1, Shuntuoguole area, Tarim Basin, including 47 ethanoadamantanes with total content of 27 594.0 μg/g, 32 ethanodiamantanes with total content of 4 415.1 μg/g, and 2 ethanotriamantanes with total content of 16.8 μg/g. The template of 2D chromatogram retention index of diamondoids-ethanodiamondoids was constructed. The results demonstrated that the position of retention time of diamondoids and ethanodiamondoids has the following relationship, namely, adamantanes < ethanoadamantanes < diamantanes < ethanodiamantanes < triadamantanes < ethanotriamantanes < tetradamantanes. Quantitative analytical result of ethanoadamantanes as saturated hydrocarbons with the highest thermal stability in crude oil, is expected to provide new indexes for secondary reservoir reconstruction, i.e. crude oil cracking and thermochemical sulfate reduction (TSR).

     

    • FullText(HTML)
  • loading
    • References(37)
  • [1]
    STAUSS S, TERASHIMA K. Diamondoids: synthesis, properties, and applications[M]. Singapore: Pan Stanford Publishing, 2017.
    [2]
    马安来, 金之钧, 晏继发, 等. 煤中金刚烷的分布与演化[J]. 石油学报, 2020, 41(7): 796-808. https://www.cnki.com.cn/Article/CJFDTOTAL-SYXB202007004.htm

    MA Anlai, JIN Zhijun, YAN Jifa, et al. Distribution and evolution of diamondoids in coals[J]. Acta Petrolei Sinica, 2020, 41(7): 796-808. https://www.cnki.com.cn/Article/CJFDTOTAL-SYXB202007004.htm
    [3]
    马安来, 金之钧, 朱翠山, 等. 塔河油田原油中金刚烷化合物绝对定量分析[J]. 石油学报, 2009, 30(2): 214-218. https://www.cnki.com.cn/Article/CJFDTOTAL-SYXB200902010.htm

    MA Anlai, JIN Zhijun, ZHU Cuishan, et al. Quantitative analysis on absolute concentration of diamondoids in oils from Tahe Oilfield[J]. Acta Petrolei Sinica, 2009, 30(2): 214-218. https://www.cnki.com.cn/Article/CJFDTOTAL-SYXB200902010.htm
    [4]
    房忱琛, 翟佳, 胡国艺, 等. 凝析油中金刚烷类和硫代金刚烷类化合物同步检测方法及地质意义: 以塔里木盆地塔中地区凝析油为例[J]. 石油实验地质, 2021, 43(5): 906-914. doi: 10.11781/sysydz202105906

    FANG Chenchen, ZHAI Jia, HU Guoyi, et al. A simultaneous determination method for diamondoids and thiadiamondoids in condensate oil and its geological significance: taking condensate oil from central Tarim Basin as an example[J]. Petroleum Geo-logy & Experiment, 2021, 43(5): 906-914. doi: 10.11781/sysydz202105906
    [5]
    杨茜, 包建平, 倪春华, 等. 蒸发分馏作用对原油中金刚烷类化合物分布与组成的影响: 以塔里木盆地库车坳陷羊塔克构造上的原油为例[J]. 石油实验地质, 2022, 44(2): 295-305. doi: 10.11781/sysydz202202295

    YANG Xi, BAO Jianping, NI Chunhua, et al. Effect of evaporative fractionation on the distribution and composition of diamondoids in crude oils: a case study of crude oils from Yangtake structure, Kuqa Depression, Tarim Basim[J]. Petroleum Geology & Experiment, 2022, 44(2): 295-305. doi: 10.11781/sysydz202202295
    [6]
    SCHOELL M, CARLSON R M K. Diamondoids and oil are not forever[J]. Nature, 1999, 399(6731): 15-16. doi: 10.1038/19847
    [7]
    马安来. 金刚烷类化合物在有机地球化学中的应用进展[J]. 天然气地球科学, 2016, 27(5): 851-860. https://www.cnki.com.cn/Article/CJFDTOTAL-TDKX201605012.htm

    MA Anlai. New advancement in application of diamondoids on organic geochemistry[J]. Natural Gas Geoscience, 2016, 27(5): 851-860. https://www.cnki.com.cn/Article/CJFDTOTAL-TDKX201605012.htm
    [8]
    DAHL J E, LIU S G, CARLSON R M K. Isolation and structure of higher diamondoids, nanometer-sized diamond molecules[J]. Science, 2002, 299(5603): 96-99. http://www.econanotechnology.intermag.info/dahl-03.pdf
    [9]
    BURNS W, MCKERVEY M A, MITCHELL T R B, et al. A new approach to the construction of diamondoid hydrocarbons. Synthesis of anti-tetramantane[J]. Journal of the American Chemical Society, 1978, 100(3): 906-911. doi: 10.1021/ja00471a041
    [10]
    FORT R C, VON R SCHLEYER P. Adamantane: consequences of the diamondoid structure[J]. Chemical Reviews, 1964, 64(3): 277-300. doi: 10.1021/cr60229a004
    [11]
    MCKERVEY M A. Synthetic approaches to large diamondoid hydrocarbons[J]. Tetrahedron, 1980, 36(8): 971-992. doi: 10.1016/0040-4020(80)80050-0
    [12]
    VON RAGUE SCHLEYER P, OSAWA E, DREW M G B. Nonacyclo[11.7.1.12, 18. 03, 16. 04, 13. 05, 10. 06, 14. 07, 11. 015, 20] docosane, a bastard tetramantane[J]. Journal of the American Che-mical Society, 1968, 90(18): 5034-5036. doi: 10.1021/ja01020a053
    [13]
    GORDADZE G N, GIRUTS M V. Synthesis of adamantane and diamantane hydrocarbons by high-temperature cracking of higher n-alkanes[J]. Petroleum Chemistry, 2008, 48(6): 414-419. doi: 10.1134/S0965544108060029
    [14]
    DAHL J E P, MOLDOWAN J M, WEI Zhibin, et al. Synthesis of higher diamondoids and implications for their formation in petroleum[J]. Angewandte Chemie, 2010, 122(51): 10077-10081. doi: 10.1002/ange.201004276
    [15]
    CUPAS C A, HODAKOWSKI L. Iceane[J]. Journal of the AmericanChemical Society, 1974, 96(14): 4668-4669.
    [16]
    FARCASIU D, WISKOTT E, OSAWA E, et al. Ethanoadamantane. Most stable C12H18 isomer[J]. Journal of the American Chemical Society, 1974, 96(14): 4669-4671. doi: 10.1021/ja00821a051
    [17]
    OSAWA E, FURUSAKI A, MATSUMOTO T, et al. Heptacyclo[8.6.0.02, 8. 03, 13. 04, 11. 05, 9. 012, 16] hexadecane a bisethano-bisnordiamantane by rearrangement[J]. Tetrahedron Letters, 1976, 17(28): 2463-2466. doi: 10.1016/0040-4039(76)90020-4
    [18]
    RAO S T, SUNDARALINGAM M, OSAWA E, et al. Hexacyclo[10, 3, 1, 02, 10, , 03, 7, 06, 15, 09, 14] hexadecane; an ethanocongressane[J]. Journal of the Chemical Society D: Chemical Communications, 1970(14): 861-862. doi: 10.1039/c29700000861
    [19]
    ZHU Guangyou, WANG Meng, ZHANG Ying, et al. Higher ethanodiamondoids in petroleum[J]. Energy & Fuels, 2018, 32(4): 4996-5000. http://www.onacademic.com/detail/journal_1000040213426510_8751.html
    [20]
    HÁLA S, LANDA S, HANUŠ V. Islolation of tetracyclo[6.3.1.02, 6. 05, 10] dodecane and pentacyclo[7.3.1.1. 4, 12. 02, 7. 06, 11] tetradecane (diamantane) from petroleum[J]. Angewandte Chemie International Edition, 1966, 5(12): 1045-1046. doi: 10.1002/anie.196610451
    [21]
    BINGHAM R C, SCHLEYER P V R. Recent developments in the chemistry of adamantane and related polycyclic hydrocarbons[M]//BINGHAM R C, SCHLEYER P R V. Chemistry of Adamantanes. Berlin: Springer, 1971: 1-102.
    [22]
    SCARLETT A G, SPAAK G, MOHAMED S, et al. Comparison of tri-, tetra- and pentacyclic caged hydrocarbons in Australian crude oils and condensates[J]. Organic Geochemistry, 2019, 127: 115-123. http://www.sciencedirect.com/science/article/pii/S014663801830264X
    [23]
    ZHU Guangyou, LI Jingfei, WANG Meng, et al. Formation and distribution of ethanodiamondoids in deeply buried marine oil from the Tarim Basin, China[J]. Organic Geochemistry, 2021, 162: 104327. http://www.sciencedirect.com/science/article/pii/S0146638021001480
    [24]
    马安来, 林会喜, 云露, 等. 塔里木盆地顺托果勒地区奥陶系原油中乙基桥键金刚烷系列的检出及意义[J]. 石油学报, 2022, 43(6): 788-803. https://www.cnki.com.cn/Article/CJFDTOTAL-SYXB202206004.htm

    MA Anlai, LIN Huixi, YUN Lu, et al. Detection of ethanodiamondoids in the Ordovician crude oil from Shuntuoguole area in Tarim Basin and its significance[J]. Acta Petrolei Sinica, 2022, 43(4): 788-803. https://www.cnki.com.cn/Article/CJFDTOTAL-SYXB202206004.htm
    [25]
    漆立新. 塔里木盆地顺北超深断溶体油藏特征与启示[J]. 中国石油勘探, 2020, 25(1): 102-111. https://www.cnki.com.cn/Article/CJFDTOTAL-KTSY202001010.htm

    QI Lixin. Characteristics and inspiration of ultra-deep fault-karst reservoir in the Shunbei area of the Tarim Basin[J]. China Petroleum Exploration, 2020, 25(1): 102-111. https://www.cnki.com.cn/Article/CJFDTOTAL-KTSY202001010.htm
    [26]
    云露. 顺北地区奥陶系超深断溶体油气成藏条件[J]. 新疆石油地质, 2021, 42(2): 136-142. https://www.cnki.com.cn/Article/CJFDTOTAL-XJSD202102002.htm

    YUN Lu. Hydrocarbon accumulation of ultra-deep Ordovician fault-karst reservoirs in Shunbei area[J]. Xinjiang Petroleum Geology, 2021, 42(2): 136-142. https://www.cnki.com.cn/Article/CJFDTOTAL-XJSD202102002.htm
    [27]
    吴鲜, 李丹, 朱秀香, 等. 塔里木盆地顺北油气田地温场对奥陶系超深层油气的影响: 以顺北5号走滑断裂带为例[J]. 石油实验地质, 2022, 44(3): 402-412. doi: 10.11781/sysydz202203402

    WU Xian, LI Dan, ZHU Xiuxiang, et al. Influence of geothermal field on ultra-deep Ordovician oil and gas in Shunbei field, Tarim Basin: a case study of Shunbei No. 5 strike-slip fault[J]. Petroleum Geology & Experiment, , 2022, 44(3): 402-412. doi: 10.11781/sysydz202203402
    [28]
    马安来, 何治亮, 云露, 等. 塔里木盆地顺北地区奥陶系超深层天然气地球化学特征及成因[J]. 天然气地球科学, 2021, 32(7): 1047-1060. https://www.cnki.com.cn/Article/CJFDTOTAL-TDKX202107011.htm

    MA Anlai, HE Zhiliang, YUN Lu, et al. The geochemical characteristics and origin of Ordovician ultra-deep natural gas in the North Shuntuoguole area, Tarim Basin, NW China[J]. Natural Gas Geoscience, 2021, 32(7): 1047-1060. https://www.cnki.com.cn/Article/CJFDTOTAL-TDKX202107011.htm
    [29]
    庄新兵, 顾忆, 邵志兵, 等. 塔里木盆地地温场对油气成藏过程的控制作用: 以古城墟隆起为例[J]. 石油学报, 2017, 38(5): 502-511. https://www.cnki.com.cn/Article/CJFDTOTAL-SYXB201705003.htm

    ZHUANG Xinbing, GU Yi, SHAO Zhibing, et al. Control effectof geothermal field on hydrocarbon accumulation process in Tarim Basin: a case study of Guchengxu uplift[J]. Acta Petrolei Sinica, 2017, 38(5): 502-511. https://www.cnki.com.cn/Article/CJFDTOTAL-SYXB201705003.htm
    [30]
    马安来, 金之钧, 朱翠山. 等. 塔里木盆地顺南1井原油硫代金刚烷系列的检出及意义[J]. 石油学报, 2018, 39(1): 42-53. https://www.cnki.com.cn/Article/CJFDTOTAL-SYXB201801004.htm

    MA Anlai, JIN Zhijun, ZHU Cuishan, et al. Detection and research significance of thiadiamondoids from crude oil in well Shunnan 1, Tarim Basin[J]. Acta Petrolei Sinica, 2018, 39(1): 42-53. https://www.cnki.com.cn/Article/CJFDTOTAL-SYXB201801004.htm
    [31]
    陈红汉, 鲁子野, 曹自成, 等. 塔里木盆地塔中地区北坡奥陶系热液蚀变作用[J]. 石油学报, 2016, 37(1): 43-63. https://www.cnki.com.cn/Article/CJFDTOTAL-SYXB201601005.htm

    CHEN Honghan, LU Ziye, CAO Zicheng, et al. Hydrothermal alteration of Ordovician reservoir in northeastern slope of Tazhong Uplift, Tarim Basin[J]. Acta Petrolei Sinica, 2016, 37(1): 43-63. https://www.cnki.com.cn/Article/CJFDTOTAL-SYXB201601005.htm
    [32]
    沙旭光, 马庆佑, 吕海涛, 等. 塔里木盆地古城墟隆起奥陶系油气成藏特征及主控因素[J]. 海相油气地质, 2014, 19(2): 15-22. https://www.cnki.com.cn/Article/CJFDTOTAL-HXYQ201402006.htm

    SHA Xuguang, MA Qingyou, LV Haitao, et al. Hydrocarbon accumulation and main controlling factors of Ordovician reservoir in Guchengxu uplift, Tarim Basin[J]. Marine Origin Petroleum Geo-logy, 2014, 19(2): 15-22. https://www.cnki.com.cn/Article/CJFDTOTAL-HXYQ201402006.htm
    [33]
    OSAWA E, ENGLER E M, GODLESKI S A, et al. Application of force field calculations to organic chemistry. 10. Bridgehead reactivitiesof ethanoadamantane. Bromination and solvolysis of bromides[J]. The Journal of Organic Chemistry, 1980, 45(6): 984-991. doi: 10.1021/jo01294a014
    [34]
    ÇAGIN T, CHE Jianwei, GARDOS M N, et al. Simulation and experiments on friction and wear of diamond: a material for MEMS and NEMS application[J]. Nanotechnology, 1999, 10(3): 278-284. http://www.wag.caltech.edu/home-pages/tahir/PDF/nems.pdf
    [35]
    PETERS K E, WALTERS C C, MOLDOWAN J M. The biomarkerguide volume 2: biomarkers and isotopes in petroleum exploration and earth history[M]. 2nd ed. Cambridge: Cambridge University Press, 2005.
    [36]
    马安来, 金之钧, 李慧莉, 等. 塔里木盆地顺北地区奥陶系超深层油藏蚀变作用及保存[J]. 地球科学, 2020, 45(5): 1737-1753. https://www.cnki.com.cn/Article/CJFDTOTAL-DQKX202005017.htm

    MA Anlai, JIN Zhijun, Ll Huili, et al. Secondary alteration and preservation of ultra-deep Ordovician oil reservoirs of north Shuntuoguole area of Tarim Basin, NW China[J]. Earth Science, 2020, 45(5): 1737-1753. https://www.cnki.com.cn/Article/CJFDTOTAL-DQKX202005017.htm
    [37]
    DAHL J E, MOLDOWAN J M, PETERS K E, et al. Diamondoid hydrocarbons as indicators of natural oil cracking[J]. Nature, 1999, 399(6731): 54-57. http://www.nature.com/nature/journal/v399/n6731/pdf/399054a0.pdf
    • Relative Articles
    • Supplements(0)
    • Cited By
  • 加载中

Catalog

    通讯作者: 陈斌, bchen63@163.com
    • 1. 

      沈阳化工大学材料科学与工程学院 沈阳 110142

    1. 本站搜索
    2. 百度学术搜索
    3. 万方数据库搜索
    4. CNKI搜索

    Figures(8)  / Tables(1)

    Citation
    XML
    PDF-CN

    Article Metrics

    Article views (266) PDF downloads(53) Cited by()
    Proportional views
    Related

    Website Copyright © Wuxi Research Institute of Petroleum Geology, SINOPEC 苏ICP备15009037号 苏公网安备32021102000780号

    Address：No. 2060, Lihu Avenue, Wuxi, Jiangsu   (214126) Tel：0510-68787204，68787203 Fax：0510-68787113 Email：sysydz.syky@sinopec.com

    Supported by: Beijing Renhe Information Technology Co. Ltd    

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return