Advanced Search
Volume 42 Issue 6
Nov.  2020
Turn off MathJax
Article Contents
Article Navigation >  PETROLEUM GEOLOGY & EXPERIMENT  > 2020  >  42(6): 1024-1030
HUANG Ling, WENG Na, WEI Caiyun, SU Jin, ZHANG Bin, ZHANG Wenlong, HU Guoyi. Analysis and identification of diamondoids by different mass spectrometry techniques[J]. PETROLEUM GEOLOGY & EXPERIMENT, 2020, 42(6): 1024-1030. doi: 10.11781/sysydz2020061024
Citation: HUANG Ling, WENG Na, WEI Caiyun, SU Jin, ZHANG Bin, ZHANG Wenlong, HU Guoyi. Analysis and identification of diamondoids by different mass spectrometry techniques[J]. PETROLEUM GEOLOGY & EXPERIMENT, 2020, 42(6): 1024-1030. doi: 10.11781/sysydz2020061024
shu

Analysis and identification of diamondoids by different mass spectrometry techniques

doi: 10.11781/sysydz2020061024
  • 1.

    Academic Exchange Department, Chinese Petroleum Society, Beijing 100724, China

  • 2.

    Key Laboratory of Petroleum Geochemistry, CNPC, Beijing 100083, China

  • Received Date: 2019-10-10
  • Rev Recd Date: 2020-10-19
  • Publish Date: 2020-11-28
    Abstract
  • Diamondoids have attracted extensive attention from researchers because of their important application value in oil and gas exploration. Since diamondoids have complex molecular structures and a large number of isomers, the identification of certain diamondoids is still controversial. In this paper, a qualitative study of adamantane derivatives, such as 1-ethyl-3-methyladamantane and 1-ethyl-3,5,7-trimethyladamantane, was carried out using gas chromatography-mass spectrometry, gas chromatography-triple quadrupole mass spectrometry and two dimensional gas chromatography-time-of-flight mass spectrometry. The chromatography peak position of these compounds in different mass spectrograms was confirmed. In addition, with the help of MASS FRONTIER software, the fragmentation mechanism and the characteristic ions formed during electron ionization was interpreted for 1-ethyl-3,5,7-trimethyladamantane in the ion source.

     

    • FullText(HTML)
  • loading
    • References(34)
  • [1]
    DAHL J E, LIU S G, CARLSON R M K. Isolation and structure of higher diamondoids, nanometer-sized diamond molecules[J]. Science, 2003, 299(5603): 96-99. doi: 10.1126/science.1078239
    [2]
    LIN Rui, WILK Z A. Natural occurrence of tetramantane (C22H28), pentamantane (C26H32) and hexamantane (C30H36) in a deep petroleum reservoir[J]. Fuel, 1995, 74(10): 1512-1521. doi: 10.1016/0016-2361(95)00116-M
    [3]
    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. doi: 10.1038/19953
    [4]
    WEI Zhibin, MOLDOWAN J M, PAYTAN A. Diamondoids and molecular biomarkers generated from modern sediments in the absence and presence of minerals during hydrous pyrolysis[J]. Organic Geochemistry, 2006, 37(8): 891-911. doi: 10.1016/j.orggeochem.2006.04.008
    [5]
    WEI Zhibin, MOLDOWAN J M, DAHL J, et al. The catalytic effects of minerals on the formation of diamondoids from kerogen macromolecules[J]. Organic Geochemistry, 2006, 37(11): 1421-1436. doi: 10.1016/j.orggeochem.2006.07.006
    [6]
    WEI Zhibin, MOLDOWAN J M, FAGO F, et al. Origins of thiadiamondoids and diamondoidthiols in petroleum[J]. Energy & Fuels, 2007, 21(6): 3431-3436.
    [7]
    HÁLA S, EYEM J, BURKHARD J, et al. Retention indices of adamantanes[J]. Journal of Chromatographic Science, 1970, 8(4): 203-209. doi: 10.1093/chromsci/8.4.203
    [8]
    MITRA G D, MOHAN G, SINHA A. Gas chromatographic analysis of complex hydrocarbon mixtures[J]. Journal of Chromatography A, 1974, 91: 633-648. doi: 10.1016/S0021-9673(01)97944-0
    [9]
    WINGERT W S.G.C. -M.S. analysis of diamondoid hydrocarbons in Smackover petroleums[J]. Fuel, 1992, 71(1): 37-43. doi: 10.1016/0016-2361(92)90190-Y
    [10]
    LIANG Qianyong, XIONG Yongqiang, FANG Chenchen, et al. Quantitative analysis of diamondoids in crude oils using Gas Chromatography-Triple Quadrupole Mmass Spectrometry[J]. Organic Geochemistry, 2012, 43: 83-91. doi: 10.1016/j.orggeochem.2011.10.008
    [11]
    FANG Chenchen, XIONG Yongqiang, LI Yun, et al. The origin and evolution of adamantanes and diamantanes in petroleum[J]. Geochimica et Cosmochimica Acta, 2013, 120: 109-120. doi: 10.1016/j.gca.2013.06.027
    [12]
    梁前勇, 熊永强, 房忱琛, 等. 两种测定原油中金刚烷类化合物方法的对比研究[J]. 地球化学, 2012, 41(5): 433-441. https://www.cnki.com.cn/Article/CJFDTOTAL-DQHX201205005.htm

    LIANG Qianyong, XIONG Yongqiang, FANG Chenchen, et al. Comparison of two methods for the determination of diamondoids in crude oils[J]. Geochimica, 2012, 41(5): 433-441. https://www.cnki.com.cn/Article/CJFDTOTAL-DQHX201205005.htm
    [13]
    闫燕. 原油中金刚烷系列化合物定量分析及应用研究[D]. 大庆: 东北石油大学, 2010.

    YAN Yan. Quantitative analysis and application study of adamantane series compounds in crude oil[D]. Daqing: Northeast Petroleum University, 2010.
    [14]
    李二庭, 向宝力, 马万云, 等. 前处理方法对原油中金刚烷化合物定量的影响[J]. 石油实验地质, 2019, 41(6): 916-922. doi: 10.11781/sysydz201906916

    LI Erting, XIANG Baoli, MA Wanyun, et al. Effect of pretreatment methods on determination of diamondoids in crude oils[J]. Petro-leum Geology & Experiment, 2019, 41(6): 916-922. doi: 10.11781/sysydz201906916
    [15]
    LI Shuifu, HU Shouzhi, CAO Jian, et al. Diamondoid characte-rization in condensate by comprehensive two-dimensional Gas Chromatography with Time-of-Flight Mass Spectrometry: the Junggar Basin of Northwest China[J]. International Journal of Molecular Sciences, 2012, 13(9): 11399-11410. doi: 10.3390/ijms130911399
    [16]
    ZHU Guangyou, WANG Huitong, WENG Na, et al. Use of comprehensive two-dimensional Gas Chromatography for the characterization of ultra-deep condensate from the Bohai Bay Basin, China[J]. Organic Geochemistry, 2013, 63: 8-17. doi: 10.1016/j.orggeochem.2013.08.002
    [17]
    王汇彤, 翁娜, 张水昌, 等. 石油样品中金刚烷类化合物的定量分析新方法[J]. 石油实验地质, 2019, 41(3): 443-450. doi: 10.11781/sysydz201903443

    WANG Huitong, WENG Na, ZHANG Shuichang, et al. A novel method for quantitative analysis of diamondoids in petroleum samples[J]. Petroleum Geology & Experiment, 2019, 41(3): 443-450. doi: 10.11781/sysydz201903443
    [18]
    李二庭, 陈俊, 迪丽达尔·肉孜, 等. 准噶尔盆地腹部地区原油金刚烷化合物特征及应用[J]. 石油实验地质, 2019, 41(4): 569-576. doi: 10.11781/sysydz201904569

    LI Erting, CHEN Jun, ROUZI Dilidaer, et al. Characteristics of diamondoids in crude oil and its application in hinterland of Junggar Basin[J]. Petroleum Geology & Experiment, 2019, 41(4): 569-576. doi: 10.11781/sysydz201904569
    [19]
    张魁英, 杨佰娟, 郑立, 等. 基于原油中金刚烷指纹半定量分析进行原油鉴别[J]. 分析化学, 2011, 39(4): 496-500. https://www.cnki.com.cn/Article/CJFDTOTAL-FXHX201104014.htm

    ZHANG Kuiying, YANG Baijuan, ZHENG Li, et al. Crude oil identification based on diamondoid fingerprinting concentrations by semiquantitative method[J]. Chinese Journal of Analytical Chemistry, 2011, 39(4): 496-500. https://www.cnki.com.cn/Article/CJFDTOTAL-FXHX201104014.htm
    [20]
    WEI Zhibin, MOLDOWAN J M, JARVIE D M, et al. The fate of diamondoids in coals and sedimentary rocks[J]. Geology, 2006, 34(12): 1013-1016. doi: 10.1130/G22840A.1
    [21]
    WEI Zhibin, MOLDOWAN J M, ZHANG Shuichang, et al. Diamondoid hydrocarbons as a molecular proxy for thermal maturity and oil cracking: geochemical models from hydrous pyrolysis[J]. Organic Geochemistry, 2007, 38(2): 227-249.
    [22]
    CHEN Junhong, FU Jiamo, SHENG Guoying, et al. Diamondoid hydrocarbon ratios: novel maturity indices for highly mature crude oils[J]. Organic Geochemistry, 1996, 25(3/4): 179-190.
    [23]
    ZHANG Shuichang, HUANG Haiping, XIAO Zhongyao, et al. Geochemistry of Palaeozoic marine petroleum from the Tarim Basin, NW China. Part 2: maturity assessment[J]. Organic Geochemistry, 2005, 36(8): 1215-1225.
    [24]
    AZEVEDO D A, TAMANQUEIRA J B, DIAS J C M, et al. Multivariate statistical analysis of diamondoid and biomarker data from Brazilian Basin oil samples[J]. Fuel, 2008, 87(10/11): 2122-2130.
    [25]
    SPRINGER M V, GARCIA D F, GONÇALVES F T T, et al. Diamondoid and biomarker characterization of oils from the Llanos Orientales Basin, Colombia[J]. Organic Geochemistry, 2010, 41(9): 1013-1018.
    [26]
    GRICE K, ALEXANDER R, KAGI R I. Diamondoid hydrocarbon ratios as indicators of biodegradation in Australian crude oils[J]. Organic Geochemistry, 2000, 31(1): 67-73.
    [27]
    WEI Zhibin, MOLDOWAN J M, PETERS K E, et al. The abundance and distribution of diamondoids in biodegraded oils from the San Joaquin Valley: implications for biodegradation of diamondoids in petroleum reservoirs[J]. Organic Geochemistry, 2007, 38(11): 1910-1926.
    [28]
    SCHULZ L K, WILHELMS A, REIN E, et al. Application of diamondoids to distinguish source rock facies[J]. Organic Geochemistry, 2001, 32(3): 365-375.
    [29]
    HANIN S, ADAM P, KOWALEWSKI I, et al. Bridgehead alkylated 2-thiaadamantanes: novel markers for sulfurisation proce-sses occurring under high thermal stress in deep petroleum reservoirs[J]. Chemical Communications, 2002(16): 1750-1751.
    [30]
    STOUT S A, DOUGLAS G S. Diamondoid hydrocarbons: application in the chemical fingerprinting of natural gas condensate and gasoline[J]. Environmental Forensics, 2004, 5(4): 225-235.
    [31]
    WANG Zhendi, YANG Chun, HOLLEBONE B, et al. Forensic fingerprinting of diamondoids for correlation and differentiation of spilled oil and petroleum products[J]. Environmental Science & Technology, 2006, 40(18): 5636-5646.
    [32]
    YANG Chun, WANG Z D, HOLLEBONE B P, et al. GC/MS quantitation of diamondoid compounds in crude oils and petro-leum products[J]. Environmental Forensics, 2006, 7(4): 377-390.
    [33]
    MOLDOWAN J M, DAHL J, ZINNIKER D, et al. Underutilized advanced geochemical technologies for oil and gas exploration and production-1. The diamondoids[J]. Journal of Petroleum Science and Engineering, 2015, 126: 87-96.
    [34]
    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
    • 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 (495) PDF downloads(106) 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