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Distribution and geochemical significance of phenylphenanthrenes and their isomers in selected oils and rock extracts from the Tarim Basin, NW China

Distribution and geochemical significance of phenylphenanthrenes and their isomers in selected... Pet. Sci. (2016) 13:183–191 DOI 10.1007/s12182-016-0095-4 ORIGINAL PAPER Distribution and geochemical significance of phenylphenanthrenes and their isomers in selected oils and rock extracts from the Tarim Basin, NW China 1 2 1 2 • • • • Shao-Ying Huang Mei-Jun Li Ke Zhang T.-G. Wang 1 2 1 • • • Zhong-Yao Xiao Rong-Hui Fang Bao-Shou Zhang 2 1 2 • • Dao-Wei Wang Qing Zhao Fu-Lin Yang Received: 25 July 2015 / Published online: 20 April 2016 The Author(s) 2016. This article is published with open access at Springerlink.com Abstract Twenty-two oil samples and eight source rock 3-MP ratios ([0.10), associating with high Pr/Ph, low ADBT/ samples collected from the Tarim Basin, NW China were ADBF, high Ts/(Ts ? Tm), and C diahopane/C hopane 30 30 geochemically analyzed to investigate the occurrence and ratios. Therefore, the occurrence of significant amounts of distribution of phenylphenanthrene (PhP), phenylanthracene phenylphenanthrenes in oils typically indicates that the organic (PhA), and binaphthyl (BiN) isomers and methylphenanthrene matter of the source rocks was deposited in a suboxic envi- (MP) isomers in oils and rock extracts with different deposi- ronment with mudstone deposition. The phenylphenanthrenes tional environments. Phenylphenanthrenes are present in sig- may be effective molecular markers, indicating depositional nificant abundance in Mesozoic lacustrine mudstones and environment and lithology of source rocks. related oils. The relative concentrations of PhPs are quite low or below detection limit by routine gas chromatography–mass Keywords Phenylphenanthrene  Methylphenanthrene spectrometry (GC–MS) in Ordovician oils derived from mar- Depositional environment  Source rock ine carbonates. The ratio of 3-PhP/3-MP was used in this study to describe the relative abundance of phenylphenanthrenes to their alkylated counterparts—methylphenanthrenes. The 1 Introduction Ordovician oils in the Tabei Uplift have quite low 3-PhP/3-MP ratios (\0.10), indicating their marine carbonate origin, asso- Phenyl-substituted polycyclic aromatic hydrocarbons ciating with low Pr/Ph ratios (pristane/phytane), high ADBT/ (PAHs) and their heterocyclic counterparts are important ADBF values (relative abundance of alkylated dibenzothio- components in aromatic fractions of some crude oils and phenes to alkylated dibenzofurans), low C diahopane/C sedimentary rock extracts (Marynowski et al. 2001, 2002, 30 30 hopane ratios, and low Ts/(Ts ? Tm) (18a-22, 29, 30-tris- 2004; Rospondek et al. 2007, 2009; Li et al. 2012a; Grafka norneohopane/(18a-22, 29, 30-trisnorneohopane ? 17a-22, et al. 2015). A series of phenylphenanthrene (PhP), 29, 30-trisnorhopane)) values. In contrast, the oils from phenylanthracene (PhA), and binaphthyl (BiN) isomers Mesozoic and Paleogene sandstone reservoirs and related have been firmly identified by using authentic standards Mesozoic lacustrine mudstones have relatively higher 3-PhP/ (Rospondek et al. 2009). The 9-phenylphenanthrene and other isomers were detected in volatiles formed during pyrolytic carbonization & Mei-Jun Li of coal tar pitches (zu Reckendorf 1997, 2000). All PhP, meijunli2008@hotmail.com PhA, and BiN isomers have been discovered in marine sedimentary rocks (Rospondek et al. 2009; Grafka et al. Research Institute of Petroleum Exploration and Development, Tarim Oilfield Company, PetroChina, 2015), Tertiary and Jurassic lacustrine shales (Li et al. Korla 841000, Xinjiang, China 2012a) and tire fire products (Wang et al. 2007). State Key Laboratory of Petroleum Resources and The phenyl-substituted PAHs in combustion products Prospecting, College of Geosciences, China University of may be generated by consecutive reactions of phenyl free Petroleum, Beijing 102249, China radicals with unsubstituted PAHs in the gaseous phase during combustion (zu Reckendorf 2000). Less work has Edited by Jie Hao 123 184 Pet. Sci. (2016) 13:183–191 been done on the origin and formation of phenylphenan- (Fig. 1). One outcrop was sampled in the Kuchehe profile threne in crude oils and sedimentary rocks. According to in the Kuqa Depression, which is the prolific hydrocarbon- Marynowski et al. (2001), Rospondek et al. (2009), and bearing foreland basin in the Tarim Basin (Zhao et al. Grafka et al. (2015), diagenetic/catagenetic oxidation of 2005). These three rock samples are Upper Triassic sedimentary organic matter at the redox interface in buried mudstones. sedimentary rocks is likely to be the main source of ary- Four Jurassic sandy mudstones were collected from the lated polycyclic aromatic compounds in the geosphere. Kuzigongsu profile in the southwest of the Tarim Basin Laboratory experiments indicate that the reaction of free (Fig. 1). The Middle Jurassic in the Tarim Basin is repre- radical phenylation with phenanthrene or anthracene moi- sented by deep lacustrine deposits (Zhang et al. 2000; Liu eties can account for the distribution of phenylphenan- et al. 2006; Cheng et al. 2008; Wang et al. 2009; Song et al. threnes and phenylanthracenes in oxidized rock samples 2013). In addition, one Jurassic coal sample from the Well with Type II and III kerogen (Marynowski et al. 2001; YL1 in the eastern Tarim Basin is also investigated. All Rospondek et al. 2009; Grafka et al. 2015). Therefore, a these samples are good source rocks with total organic significant amount of PhPs and other phenyl-substituted carbon (TOC) content of 0.71 %–1.12 % (Table 1), and PAHs in ancient sedimentary rocks are commonly associ- they underwent moderate to relatively higher thermal ated with oxic to suboxic depositional environments. maturation with vitrinite reflectance (R %) of 0.51 %– The distribution patterns of PhPs and BiNs in mass 1.10 % (Table 1). chromatograms (m/z 254) of aromatic fractions in sedi- A total of 22 oil samples were collected from the mentary organic matters are relative to the maturation Ordovician carbonate reservoirs in the Halahatang Sag, levels. For example, the most stable isomers 2-PhP and Yakela Faulted Uplift and Akekule Uplift, and the Meso- 3-PhP predominate, whereas the thermally unstable 9-PhP, zoic and Paleogene sandstone reservoirs in the Kuqa 1-PhP, and 4-PhP disappear in highly mature sedimentary Depression and Yakela Uplift of the Tarim Basin organic matter (Rospondek et al. 2009; Li et al. 2012a; (Table 1). The Ordovician carbonate oils from the Tabei Grafka et al. 2015). Among all binaphthyl isomers, 1,1-BiN Uplift were sourced from Paleozoic carbonate source rocks is the most thermally unstable one and was found only in (Zhang and Huang 2005; Wang et al. 2008; Pang et al. less mature samples; while 2,2-BiN is more stable and also 2010; Li et al. 2012b). Oils in wells QL1, Ku1, and S3 were present above the oil window range (Rospondek et al. derived from Mesozoic lacustrine mudstones (Xiao et al. 2009; Li et al. 2012a). Therefore, some indices, such as 2004; Song et al. 2015). phenylphenanthrene ratio [defined as (2- ? 3-PhP)/(2- ? 3- ? 4- ? 1- ? 9-PhP)] (Rospondek et al. 2009) and 0 0 0 0 2,2 -BiN/1,2 -BiN (defined as 2,2 -binaphthyl/1,2 -binaph- 3 Methods thyl) (Li et al. 2012a) have been proposed as maturity indicators. In addition, some maturity indicators associated All rocks were ground into powder in a crusher to \80 with aromatic compounds including phenylphenanthrene mesh. The TOC content was measured on an LECO CS- ratios have also been used as frictional stress indicators 230 carbon/sulfur analyzer. The vitrinite reflectance values (Polissar et al. 2011). (%) were measured on polished rock blocks using a Leitz Previous studies mainly focused on the formation and MPV-microscopic photometer. application of PhPs in maturation assessment. This paper To extract soluble bitumen, the powder was processed reported the occurrence of PhPs in Ordovician oils, for 24 h in a Soxhlet apparatus using 400 mL of dichlor- Mesozoic lacustrine sedimentary rocks, and related oils omethane and methanol as the solvent (93:7, v:v). from the Tarim Basin, NW China. Their potential signifi- Asphaltenes were removed from approximately 20–50 mg cance to the depositional environment and lithology of oils and bitumen by precipitation using 50 mL of n-hexane source rocks and application in oil-to-source correlation in and then fractionated by liquid chromatography using oil petroleum system are discussed. The result can further alumina/silica gel columns into saturated and aromatic broaden the geochemical significance and application of hydrocarbons using 30 mL n-hexane and 20 mL dichlor- phenylphenanthrenes in sedimentary rocks and related oils. omethane: n-hexane (2:1, v:v) as respective eluents (Fang et al. 2015). The GC–MS analyses of the aromatic fractions were 2 Samples and geological settings performed on an Agilent 5975i GC–MS system equipped with an HP-5MS (5 %-phenylmethylpolysiloxane)-fused A total of eight cores and outcrop samples were collected silica capillary column (60 m 9 0.25 mm i.d., with a 0.25- from the Tarim Basin, NW China. Two cores were sampled lm film thickness). The GC operating conditions were as from Well S5, which is located in the Yakela Faulted Uplift follows: the temperature was held initially at 80 C for 123 Kuzigongsu Maigaiti Slope Tazhong Uplift Southwestern Depression Pet. Sci. (2016) 13:183–191 185 Ta ri m Basin 0 80 km Ku1 Beijing QL1 Kuqa Depression S3 YD2 China S5 RP8 YL1 JY1 Manjiaer Depression Awati Depression Bachu Uplift YL1 Well Outcrop profile Fault Primary structure belt Secondary structure belt Fig. 1 Map showing the major tectonic terrains in the Tarim Basin (NW China) and the locations of sampled wells and profiles 1 min, increased to 310 C at a rate of 3 C/min, and then present in quite low concentration or below detection limit kept isothermal for 16 min. Helium was used as the carrier in oils (Figs. 3, 4). However, it seems abundant in some gas. The injector temperature was set to 300 C. The MS was rocks and coals (Figs. 2c, 4a, b e). operated in the electron impact (EI) mode with ionization The distribution of arylated homologues of phenan- energy of 70 eV, and a scan range of m/z 50–600 Da. threnes (phenylphenanthrenes) is shown in Fig. 2.In addition, their binaphthyl (BiN) isomers were also detected in oils and rock extracts. The elution sequence of m/z 254 4 Results and discussion isomers on an HP-5MS capillary column is as follows: 1,1 - 0 0 BiN, 4-PhP, 9-PhA, 1,2 -BiN, 9-PhP, 1-PhP, 3-PhP, 2,2 - 4.1 Identification of phenylphenanthrenes BiN, 2-PhP, and 2-PhA. The 1-PhA isomer may co-elute and methylphenanthrenes with 1,2 -BiN on HP-5MS column, but it is typically absent in geochemical samples (Rospondek et al. 2009). The The identification and elution order of all isomers of isomers 3-PhP, 2-PhP, and 2,2 -BiN are typically present in methylphenanthrenes (MPs), phenylphenanthrenes (in- higher abundance relative to other PhP and BiN isomers. cluding their isomers: phenylanthracene and binaphthyl) were determined by the comparison of their mass spectra 4.2 Depositional environment and lithologies and standard retention indices (I ) with those reported of crude oils and source rocks HP-5MS in literature (Lee et al. 1979; Rospondek et al. 2009). Figure 2 shows the chemical structures of MPs and PhPs Previous studies suggested that oils in wells Ku1 and QL1 and the mass chromatograms (m/z 178, 192, 254) of aro- of the Kuqa Depression and wells YD2 and S3 of the Tabei matic fractions of selected sediment extracts in this study. Uplift (Fig. 1) are of typical lacustrine mudstone origin (Li The methyl and phenyl substitution pattern on parent rings et al. 2004; Xiao et al. 2004; Song et al. 2015). Oils from is indicated on the corresponding peaks (Fig. 2). Ordovician carbonate reservoirs were derived from Paleo- Phenanthrene and its alkylated homologues are impor- zoic carbonate source rocks (Zhang and Huang 2005; tant polycyclic aromatic hydrocarbons (PAHs) and present Wang et al. 2008; Chang et al. 2013). in significant concentrations in crude oils and sedimentary Dibenzothiophene, dibenzofuran, and their alkylated rock extracts. Four methylphenanthrene isomers and one homologues are effective molecular markers in inferring methylanthracene isomer (2-methylanthracene: 2-MA) depositional environment, maturation assessment and in trac- were identified in all rocks and oils in this study. The ing oil charging pathways (Bao et al. 1996;Wang etal. 2014; elution order of the m/z 192 isomers is as follows: 3-MP, Li et al. 2008; Zhang and Philp. 2010;Liet al. 2011, 2014). A 2-MP, 2-MA, 9-MP, and 1-MP. The isomer 2-MA is cross-plot of alkyldibenzothiophene/alkyldibenzofuran ratio Luntai Uplift Tabei Uplift Tanggu Depression Kalpin Uplift Southeastern Uplift Southeastern Depression 186 Pet. Sci. (2016) 13:183–191 Table 1 Bulk properties and selected geochemical parameters for oils and rocks in this study Sample Fm. Description TOC, % R , % Methylphenanthrene 3-PhP/ Pr/ ADBT/ C DiaH/ Ts/(Ts ? o 30 no. index (MPI1) 3-MP Ph ADBF C H Tm) YD2 Cretaceous Oil, Tabei Uplift – – 0.51 0.12 2.17 0.54 0.48 0.67 S3 Cretaceous Oil, Yakela Faulted Uplift – – 1.11 0.09 1.63 0.33 0.92 0.66 Ku1 Jurassic Oil, Kuqa Depression – – 0.13 0.17 1.84 0.26 0.50 0.55 QL1 Paleogene Oil, Kuqa Depression – – 0.66 0.60 1.79 0.48 0.64 0.63 RP10 Ordovician Oil, Halahatang Sag – – 0.78 0.03 0.81 7.52 0.09 0.37 RP4 Ordovician Oil, Halahatang Sag – – 0.38 0.01 0.76 8.06 0.08 0.42 RP3013 Ordovician Oil, Halahatang Sag – – 0.96 0.03 0.92 9.06 0.12 0.53 RP11 Ordovician Oil, Halahatang Sag – – 0.78 0.02 0.97 6.71 0.12 0.45 RP8 Ordovician Oil, Halahatang Sag – – 0.87 0.03 0.75 10.5 0.12 0.45 JY1 Ordovician Oil, Halahatang Sag – – 0.96 0.02 0.83 7.16 0.12 0.58 JY7 Ordovician Oil, Halahatang Sag – – 0.92 0.02 1.04 9.06 0.09 0.49 JY3 Ordovician Oil, Halahatang Sag – – 0.70 0.02 1.03 8.61 0.09 0.45 XK5 Ordovician Oil, Halahatang Sag – – 0.85 0.02 0.82 6.81 0.10 0.42 XK4 Ordovician Oil, Halahatang Sag – – 0.71 0.01 0.97 5.39 0.08 0.40 XK7 Ordovician Oil, Halahatang Sag – – 0.79 0.03 0.81 7.69 0.09 0.29 XK9005 Ordovician Oil, Halahatang Sag – – 0.94 0.01 1.05 9.83 0.08 0.46 Ha601 Ordovician Oil, Halahatang Sag – – 0.72 0.02 0.88 5.63 0.17 0.44 Ha7-1 Ordovician Oil, Halahatang Sag – – 0.80 0.01 1.00 9.08 0.17 0.43 Ha8 Ordovician Oil, Halahatang Sag – – 0.70 0.02 0.98 6.52 0.12 0.37 Ha13-6 Ordovician Oil, Halahatang Sag – – 0.74 0.01 1.01 6.84 0.11 0.46 TP12-8 Ordovician Oil, Akekule – – 0.89 0.03 0.91 2.72 0.08 0.49 TP14 Ordovician Oil, Akekule – – 0.65 0.02 0.87 10.10 0.06 0.45 S5 Triassic Mudstone, core, 5400.8 m 0.71 0.74 0.48 0.11 1.26 0.17 0.65 0.85 S5 Triassic Mudstone, core, 5405.4 m 0.73 0.75 0.42 0.10 1.21 0.75 n.d. 0.87 Ku-13 Jurassic Sandy mudstone, outcrop, 1.64 1.10 0.72 0.17 1.56 0.47 1.55 0.76 Kuzigongsu Ku-18 Jurassic Sandy mudstone, outcrop, 2.02 0.99 0.64 0.16 2.10 0.22 2.97 0.86 Kuzigongsu Ku-26 Jurassic Sandy mudstone, outcrop, 3.53 0.94 0.19 0.98 1.59 0.12 6.71 0.96 Kuzigongsu Ku-30 Jurassic Sandy mudstone, outcrop, 3.27 0.93 0.22 0.90 2.00 0.10 4.48 0.92 Kuzigongsu YL1 Jurassic Coal, core, 2878.0 m 38.4 0.51 0.35 0.33 3.77 0.50 n.d. n.d. KCH-01 Triassic Mudstone, outcrop, 1.12 0.26 1.44 2.08 0.31 n.d. 0.88 Kuchehe n.d.: no data (ADBT/ADBF) versus pristane/phytane ratio (Pr/Ph) provides Zone 3 (Fig. 5), suggesting the mudstone lithology of their a powerful and convenient way to infer crude oil source rock source rocks. On the basis of oil-to-source correlation depositional environments and lithologies (Radke et al. 2000). results, all these oils were derived from Mesozoic lacus- The oils from Ordovician reservoirs in the Tabei Uplift were trine mudstone source rocks (e.g., Song et al. 2015). characterized by lower Pr/Ph ratio and higher ADBT/ADBF Selected Mesozoic mudstones from the Kuqa Depres- ratio (Table 1), and the data points were plotted in Zone 1A of sion and the Tabei Uplift were also analyzed. All rock the cross-plot of ADBT/ADBF versus Pr/Ph ratios, indicating samples have relatively higher Pr/Ph ratios and quite low their marine carbonate origin (Fig. 5). values of ADBT/ADBF. The points also fall into Zone 3, Oils from Jurassic and Paleogene reservoirs in the Kuqa indicating their lacustrine mudstone lithology (Fig. 5). The Depression and oils from Cretaceous reservoirs in the coal sample from Well YL1 in the eastern Tarim Basin has Tabei Uplift have relatively higher Pr/Ph values and very very high Pr/Ph ratio, which falls into Zone 4 (fluvial/ low ADBT/ADBF values. All these data points fall into deltaic carbonaceous shale and coal zone). 123 Pet. Sci. (2016) 13:183–191 187 Phenanthrene Well Yuli1, 2878 m 100 m/z 178 (a) Middle Jurassic, Coal Tarim Basin, NW China 60 5 10 1 1’ 6 7 2’ 7 10 6 8 4 5 9 Phenanthrene Anthracene 2,2’-Binaphthyl (2,2’-BiN) 9-MP 2-MP m/z 192 (b) 1-MP 3-MP CH 4 3 1’ 1 2-MA 2’ 7 10 8 9 2-Methylphenanthrene (2-MP) 1,2’-Binaphthyl (1,2’-BiN) 2,2’-BiN (c) m/z 254 3 3-PhP 7 10 2-PhP 8 9 2-Phenylphenanthrene (2-PhP) 2-PhA 40 1,2’-BiN 1,1’-BiN 1-PhA 9-PhP 4-PhP 1-PhP 9-PhA 40 42 44 46 48 50 52 54 56 58 60 62 64 66 68 70 Retention time, min Fig. 2 Identification of phenanthrene (m/z 178), methylphenanthrene and methylanthracene (m/z 192), and phenylphenanthrene, phenylan- thracene, and binaphthyl isomers (m/z 254) in sedimentary rocks and their chemical structures Therefore, the relative abundances of alkylated diben- concentrations, and 1,2 -biphenyl is commonly absent or zothiophenes to alkylated dibenzofurans and pristane to under detection limit. The 3-PhP is the dominant com- phytane confirm that the oils in the Ordovician reservoirs pound among all PhP, PhA, and BiN isomers in m/z 254 are of marine carbonate origin and the oils from Mesozoic mass chromatograms. The concentrations of PhPs are and Paleogene sandstone reservoirs in the Kuqa Depression generally lower than those of their methylated counter- and Tabei Uplift of the Tarim Basin are of lacustrine parts—MPs in all oils. Here we defined 3-PhP/3-MP to mudstone origin. indicate the relative abundance of PhPs to MPs. The oils from wells Ku1, QL1, YD2, and S3 have 3-PhP/3-MP 4.3 Distribution of PhPs and MPs in oils and source ratios higher than 0.10. However, oils from Ordovician rocks reservoirs in the Tabei Uplift, including Ha6, Repu, Xin- ken, Jinyue, and Tuofutai blocks, have extremely low Most of the phenylphenanthrene isomers were detected in concentrations of phenylphenanthrenes with 3-PhP/3-MP oils from wells Ku1, QL1, YD2, and S3 (Fig. 3a–d). They ratios lower than 0.10 (Fig. 4e, f; Table 1). are present in differing abundance in these oils. The isomer Selected Mesozoic lacustrine mudstones were also of 2,2 -biphenyl is typically present in quite low investigated to analyze the distribution patterns of PhPs and Relative abundance, % 188 Pet. Sci. (2016) 13:183–191 9-MP 2-MP m/z 192+254 (a) (a) 9-MP 3-MP m/z 192+254 Well Ku1, Oil 2-MP 1-MP Jurassic Well S5, 5400.8 m 3-MP 1-MP 3-PhP/3-MP=0.60 2,2’-BiN Upper Triassic, Mudstone 2-MA 9-PhP TOC=0.71% 3-PhP 2,2’-BiN 3-PhP/3-MP=0.11 2-PhP 2-PhP 1,2’-BiN 3-PhP 1-PhP 9-PhP 1,2’-BiN 1-PhP (b) (b) Well QL1, Oil Paleogene Well S5, 5405.4 m 3-PhP/3-MP=0.17 Upper Triassic, Mudstone TOC=0.73% 3-PhP/3-MP=0.10 (c) (c) Well YD2, Oil Ku-18, Kuzigongsu Cretaceous Middle Jurassic, Sandy mudstone 3-PhP/3-MP=0.12 TOC=2.02% 3-PhP/3-MP=0.16 Well S3, Oil (d) (d) Cretaceous Ku-30, Kuzigongsu 3-PhP/3-MP=0.09 Middle Jurassic, Sandy mudstone TOC=3.27% 3-PhP/3-MP=0.90 (e) 9-MP 1-MP (e) Well Rp8, Oil 2-MP Well YL1, 2878 m Ordovician 3-MP Middle Jurassic, Mudstone 3-PhP/3-MP=0.03 TOC=38.40% 2-MA 1-PhP 2,2’-BiN 3-PhP/3-MP=0.33 ×5 9-PhP 3-PhP 2-PhP 1,2’-BiN 2-MP 9-MP 1-MP (f) Relative retention time 3-MP Well JY1, Oil Ordovician Fig. 4 Distribution of methylphenanthrenes (m/z 192), 3-PhP/3-MP=0.02 2,2’-BiN phenylphenanthrenes (m/z 254), and their isomers in Mesozoic source ×5 1-PhP rocks in the Tarim Basin 2-PhP 3-PhP 9-PhP YD2, and S3. Therefore, the occurrence and distribution of phenylphenanthrene and methylphenanthrenes in Mesozoic Relative retention time oils and source rocks further confirmed their genetic affinity. Fig. 3 Distribution of methylphenanthrenes (m/z 192), phenylphenanthrenes (m/z 254), and their isomers in selected oils 4.4 Effect of environment and lithology from the Tarim Basin on the distribution of MPs and PhPs MPs in sedimentary rock extracts. Most of the PhP isomers and 2,2 -BiN were detected in all rocks in this study. For the Much work has been done on the occurrence and distribution lower thermodynamic stability, PhAs and 1,1 -BiN are of methylated phenanthrenes. For example, Alexander et al. generally below detection limit in this study. The ratio of (1995) demonstrated that the sedimentary methylation pro- 3-PhP/3-MP in Mesozoic lacustrine mudstones is from 0.11 cess can form some alkylphenanthrene isomers. Due to the to 1.44, which is consistent with oils from wells Ku1, QL1, ubiquitous occurrence, the methylphenanthrenes appear to Relative abundance Relative abundance Pet. Sci. (2016) 13:183–191 189 12 1.10 Mesozoic oil 1.00 Paleogene oil 0.90 10 Ordovician oil Mesozoic source rock 0.80 Zone 1C 0.70 Zone 1A: Marine; Carbonate 0.60 Zone 1B: Marine and lacustrine (sulfate-rich); Zone 1A Mixed and carbonate 0.50 Zone 1C: Lacustrine; Mixed (mature mudstone) Zone 1D: Lacustrine; Mixed (high-rank coal) Mesozoic oil 0.40 Zone 2: Lacustrine (sulfate-poor); Paleogene oil Variable lithology 0.30 Zone 3: Marine and other lacustrine; Shale Ordovician oil Zone 4: Fluvial/Deltaic; 0.20 Carbonaceous shale and coal Mesozoic rock 0.10 Zone 1B Zone 1D 0.00 0.0 0.1 0.2 0.3 0.4 0.5 0.6 0.7 0.8 0.9 1.0 1.1 1.2 1.3 1.4 1.5 Zone 2 Zone 3 Zone 4 3-PhP/3-MP 012 3 4 Pr/Ph Fig. 6 The cross-plot of Ts/(Ts ? Tm) versus 3-PhP/3-MP ratio provides a useful way to infer the depositional environment and Fig. 5 Cross-plot of alkyldibenzothiophene/alkyldibenzofuran ratio lithology of oils and related source rocks. Ts—C 18a-22,29,30- (ADBT/ADBF) versus pristane/phytane ratio (Pr/Ph) showing crude trisnorneohopane; Tm—C 17a-22,29,30-trisnorhopane oil source rock depositional environments and lithologies (after Radke et al. 2000) ([0.55) and 3-PhP/3-MP ratios ([0.10) (Fig. 6). The have limited depositional environment and lithology signifi- higher Ts/(Ts ? Tm) ratios for Mesozoic oils and source cance. They are effective molecular markers for thermal rocks are mainly attributed to a suboxic depositional maturity assessment (e.g., Radke et al. 1982; Boreham et al. environment and clay-rich lithology, because Ordovician 1988; Voigtmann et al. 1994; Szczerba and Rospondek 2010). oils sourced from Paleozoic marine source rocks have Here we use 3-PhP/3-MP to show the abundance of generally higher maturation levels than those from the phenylphenanthrenes relative to methylphenanthrenes in Mesozoic lacustrine source rocks. oils and sedimentary organic matter. The abundance of The C diahopane in sedimentary rock extracts and oils parent phenanthrene may be different for the differences in may be derived from bacterial hopanoid precursors that the input of organic matter in source rocks and/or thermal have experienced oxidation and rearrangement by clay- maturation level of sedimentary organic matter. As pro- mediated acidic catalysis. Therefore, the presence of a posed by previous studies (Marynowski et al. 2001; significant amount of C diahopane indicates bacterial Rospondek et al. 2009), the phenylation of phenanthrene is input to sediments containing clays deposited under oxic or mainly associated with an oxidizing depositional environ- suboxic environments (Peters et al. 2005). In this study, the ment. Therefore, an oxic to suboxic environment may favor C diahopane is generally present in very low concentra- the formation of phenylphenanthrenes. The cross-plot of tion in Ordovician oils (with C diahopane/C hopane 30 30 Ts/(Ts ? Tm) versus 3-PhP/3-MP is used here to investi- ratios lower than 0.20). While Mesozoic and Paleogene oils gate the effect of the depositional environment and lithol- from wells Ku1, QL1, S3, and YD2 and Mesozoic lacus- ogy on the distribution patterns of MPs and PhPs. The Ts/ trine mudstones have higher C diahopane/C hopane 30 30 (Ts ? Tm) ratio (18a-22,29,30-trisnorneohopane/(18a- ratios (Table 1). Therefore, our study suggests that the 22,29,30-trisnorneohopane ? 17a-22,29,30-tris- presence of a significant amount of phenylphenanthrenes is norhopane)) depends on both source and maturity (Mol- generally related to clay-enriched sediments deposited dowan et al. 1986). It is a reliable maturity indictor when under suboxic conditions. assessing oils from a common source of consistent organic facies (Peters et al. 2005). This ratio increases with the increasing maturity. It is sensitive to clay-catalyzed reac- 5 Conclusions tions. For example, oils from carbonate source rocks appear to have low Ts/(Ts ? Tm) ratios compared with Phenyl phenanthrenes and their isomers have been detected those from shales (e.g., Rullko¨tter et al. 1985). in oils and source rocks from the Tarim Basin, NW China. Here we found that oils from Ordovician reservoirs have 3-phenylphenanthrene (3-PhP), 2-PhP, and 1,2 -binaph- relatively lower Ts/(Ts ? Tm) values (\0.50) and very thyls (1,2 -BiN) are typically predominant compounds low 3-PhP/3-MP ratios (\0.10). In contrast, the Mesozoic among all isomers. The abundances of phenylphenanthre- and Paleogene oils from wells Ku1, QL1, S3, and YD2 and nes are extremely low in Ordovician oils in the Tabei Uplift Mesozoic lacustrine mudstones have higher Ts/(Ts ? Tm) of the Tarim Basin. The Mesozoic oils from wells QL1 and ADBT/ADBF Ts/(Ts+Tm) 190 Pet. Sci. (2016) 13:183–191 Grafka O, Marynowski L, Simoneit BRT. Phenyl derivatives of Ku1 from the Kuqa Depression and wells S3 and YD2 from polycyclic aromatic compounds as indicators of hydrothermal the Tabei Uplift have relatively higher concentrations of activity in the Silurian black siliceous shales of the Bardzkie phenylphenanthrenes. Mountains, Poland. Int J Coal Geol. 2015;139(1):142–51. The ratio of 3-PhP/3-MP (3-phenylphenanthrene/3- Lee ML, Vassilaros DL, White CM, et al. Retention indices for programmed-temperature capillary-column gas chromatography methylphenanthrene) is used to indicate the relative abun- of polycyclic aromatic hydrocarbons. J Chromatogr A. 1979; dances of phenylphenanthrenes to methylphenanthrenes. We 51:768–74. discovered that oils from marine carbonate source rocks have Li JG, Liu WH, Zheng JJ, et al. Dibenzofuran series of terrestrial a very low ratio (\0.10). However, oils of lacustrine mud- source rocks and crude oils in Kuqa Depression. Acta Pet Sin. 2004;25(1):40–43, 47 (in Chinese). stone origin and related source rocks have relatively high Li M, Wang T, Liu J, et al. Total alkyl dibenzothiophenes content tracing 3-PhP/3-MP ratios, associating with higher Pr/Ph, Ts/ the filling pathway of condensate reservoir in the Fushan depres- (Ts ? Tm) and C diahopane/C hopane values. 30 30 sion, South China Sea. Sci China (Ser D). 2008;51:138–45. The occurrence and distribution of phenylphenanthrenes Li M, Shi S, Wang T-G, et al. The occurrence and distribution of phenylphenanthrenes, phenylanthracenes and binaphthyls in in oils and sedimentary rock extracts in the Tarim Basin Palaeozoic to Cenozoic shales from China. Appl Geochem. clearly show an environment dependence. Relatively 2012a;27(12):2560–9. higher abundance of phenylphenanthrenes (3-PhP/3-MP Li M, Wang T, Shi S, et al. The oil maturity assessment by maturity higher than 0.10) generally suggests clay-enriched sedi- indicators based on methylated dibenzothiophenes. Pet Sci. 2014;11(2):234–46. ments under suboxic depositional environment. Certainly, Li M, Wang T-G, Lillis PG, et al. The significance of 24-norcholestanes, further work is needed to investigate whether this is valid triaromatic steroids and dinosteroids in oils and Cambrian- in other basins. Ordovician source rocks from the cratonic region of the Tarim Basin, NW China. Appl Geochem. 2012b;27(8):1643–54. Acknowledgments The work was financially supported by the Li S, Pang X, Shi Q, et al. Origin of the unusually high dibenzothio- National Natural Science Foundation of China (Grant No. 41272158) phene concentrations in Lower Ordovician oils from the Tazhong and the State Key Laboratory of Petroleum Resources and Uplift, Tarim Basin, China. Pet Sci. 2011;8(4):382–91. Prospecting (PRP/indep-2-1402). The authors thank the assistance of Liu S, Qiu M, Chen X, et al. Sedimentary setting of Mesozoic and its Zhu Lei in the GC–MS analysis. We are grateful to three anonymous petroleum geologic features in western Tarim Basin. Xinjiang reviewers for their constructive comments and suggestions. We thank Pet Geol. 2006;27:10–4 (in Chinese). the Tarim Oilfield Company of PetroChina for providing samples and Marynowski L, Czechowski F, Simoneit BRT. Phenylnaphthalenes data, and for permission to publish this work. and polyphenyls in Palaeozoic source rocks of the Holy Cross Mountains, Poland. 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Distribution and geochemical significance of phenylphenanthrenes and their isomers in selected oils and rock extracts from the Tarim Basin, NW China

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Earth Sciences; Mineral Resources; Industrial Chemistry/Chemical Engineering; Industrial and Production Engineering; Energy Economics
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Pet. Sci. (2016) 13:183–191 DOI 10.1007/s12182-016-0095-4 ORIGINAL PAPER Distribution and geochemical significance of phenylphenanthrenes and their isomers in selected oils and rock extracts from the Tarim Basin, NW China 1 2 1 2 • • • • Shao-Ying Huang Mei-Jun Li Ke Zhang T.-G. Wang 1 2 1 • • • Zhong-Yao Xiao Rong-Hui Fang Bao-Shou Zhang 2 1 2 • • Dao-Wei Wang Qing Zhao Fu-Lin Yang Received: 25 July 2015 / Published online: 20 April 2016 The Author(s) 2016. This article is published with open access at Springerlink.com Abstract Twenty-two oil samples and eight source rock 3-MP ratios ([0.10), associating with high Pr/Ph, low ADBT/ samples collected from the Tarim Basin, NW China were ADBF, high Ts/(Ts ? Tm), and C diahopane/C hopane 30 30 geochemically analyzed to investigate the occurrence and ratios. Therefore, the occurrence of significant amounts of distribution of phenylphenanthrene (PhP), phenylanthracene phenylphenanthrenes in oils typically indicates that the organic (PhA), and binaphthyl (BiN) isomers and methylphenanthrene matter of the source rocks was deposited in a suboxic envi- (MP) isomers in oils and rock extracts with different deposi- ronment with mudstone deposition. The phenylphenanthrenes tional environments. Phenylphenanthrenes are present in sig- may be effective molecular markers, indicating depositional nificant abundance in Mesozoic lacustrine mudstones and environment and lithology of source rocks. related oils. The relative concentrations of PhPs are quite low or below detection limit by routine gas chromatography–mass Keywords Phenylphenanthrene  Methylphenanthrene spectrometry (GC–MS) in Ordovician oils derived from mar- Depositional environment  Source rock ine carbonates. The ratio of 3-PhP/3-MP was used in this study to describe the relative abundance of phenylphenanthrenes to their alkylated counterparts—methylphenanthrenes. The 1 Introduction Ordovician oils in the Tabei Uplift have quite low 3-PhP/3-MP ratios (\0.10), indicating their marine carbonate origin, asso- Phenyl-substituted polycyclic aromatic hydrocarbons ciating with low Pr/Ph ratios (pristane/phytane), high ADBT/ (PAHs) and their heterocyclic counterparts are important ADBF values (relative abundance of alkylated dibenzothio- components in aromatic fractions of some crude oils and phenes to alkylated dibenzofurans), low C diahopane/C sedimentary rock extracts (Marynowski et al. 2001, 2002, 30 30 hopane ratios, and low Ts/(Ts ? Tm) (18a-22, 29, 30-tris- 2004; Rospondek et al. 2007, 2009; Li et al. 2012a; Grafka norneohopane/(18a-22, 29, 30-trisnorneohopane ? 17a-22, et al. 2015). A series of phenylphenanthrene (PhP), 29, 30-trisnorhopane)) values. In contrast, the oils from phenylanthracene (PhA), and binaphthyl (BiN) isomers Mesozoic and Paleogene sandstone reservoirs and related have been firmly identified by using authentic standards Mesozoic lacustrine mudstones have relatively higher 3-PhP/ (Rospondek et al. 2009). The 9-phenylphenanthrene and other isomers were detected in volatiles formed during pyrolytic carbonization & Mei-Jun Li of coal tar pitches (zu Reckendorf 1997, 2000). All PhP, meijunli2008@hotmail.com PhA, and BiN isomers have been discovered in marine sedimentary rocks (Rospondek et al. 2009; Grafka et al. Research Institute of Petroleum Exploration and Development, Tarim Oilfield Company, PetroChina, 2015), Tertiary and Jurassic lacustrine shales (Li et al. Korla 841000, Xinjiang, China 2012a) and tire fire products (Wang et al. 2007). State Key Laboratory of Petroleum Resources and The phenyl-substituted PAHs in combustion products Prospecting, College of Geosciences, China University of may be generated by consecutive reactions of phenyl free Petroleum, Beijing 102249, China radicals with unsubstituted PAHs in the gaseous phase during combustion (zu Reckendorf 2000). Less work has Edited by Jie Hao 123 184 Pet. Sci. (2016) 13:183–191 been done on the origin and formation of phenylphenan- (Fig. 1). One outcrop was sampled in the Kuchehe profile threne in crude oils and sedimentary rocks. According to in the Kuqa Depression, which is the prolific hydrocarbon- Marynowski et al. (2001), Rospondek et al. (2009), and bearing foreland basin in the Tarim Basin (Zhao et al. Grafka et al. (2015), diagenetic/catagenetic oxidation of 2005). These three rock samples are Upper Triassic sedimentary organic matter at the redox interface in buried mudstones. sedimentary rocks is likely to be the main source of ary- Four Jurassic sandy mudstones were collected from the lated polycyclic aromatic compounds in the geosphere. Kuzigongsu profile in the southwest of the Tarim Basin Laboratory experiments indicate that the reaction of free (Fig. 1). The Middle Jurassic in the Tarim Basin is repre- radical phenylation with phenanthrene or anthracene moi- sented by deep lacustrine deposits (Zhang et al. 2000; Liu eties can account for the distribution of phenylphenan- et al. 2006; Cheng et al. 2008; Wang et al. 2009; Song et al. threnes and phenylanthracenes in oxidized rock samples 2013). In addition, one Jurassic coal sample from the Well with Type II and III kerogen (Marynowski et al. 2001; YL1 in the eastern Tarim Basin is also investigated. All Rospondek et al. 2009; Grafka et al. 2015). Therefore, a these samples are good source rocks with total organic significant amount of PhPs and other phenyl-substituted carbon (TOC) content of 0.71 %–1.12 % (Table 1), and PAHs in ancient sedimentary rocks are commonly associ- they underwent moderate to relatively higher thermal ated with oxic to suboxic depositional environments. maturation with vitrinite reflectance (R %) of 0.51 %– The distribution patterns of PhPs and BiNs in mass 1.10 % (Table 1). chromatograms (m/z 254) of aromatic fractions in sedi- A total of 22 oil samples were collected from the mentary organic matters are relative to the maturation Ordovician carbonate reservoirs in the Halahatang Sag, levels. For example, the most stable isomers 2-PhP and Yakela Faulted Uplift and Akekule Uplift, and the Meso- 3-PhP predominate, whereas the thermally unstable 9-PhP, zoic and Paleogene sandstone reservoirs in the Kuqa 1-PhP, and 4-PhP disappear in highly mature sedimentary Depression and Yakela Uplift of the Tarim Basin organic matter (Rospondek et al. 2009; Li et al. 2012a; (Table 1). The Ordovician carbonate oils from the Tabei Grafka et al. 2015). Among all binaphthyl isomers, 1,1-BiN Uplift were sourced from Paleozoic carbonate source rocks is the most thermally unstable one and was found only in (Zhang and Huang 2005; Wang et al. 2008; Pang et al. less mature samples; while 2,2-BiN is more stable and also 2010; Li et al. 2012b). Oils in wells QL1, Ku1, and S3 were present above the oil window range (Rospondek et al. derived from Mesozoic lacustrine mudstones (Xiao et al. 2009; Li et al. 2012a). Therefore, some indices, such as 2004; Song et al. 2015). phenylphenanthrene ratio [defined as (2- ? 3-PhP)/(2- ? 3- ? 4- ? 1- ? 9-PhP)] (Rospondek et al. 2009) and 0 0 0 0 2,2 -BiN/1,2 -BiN (defined as 2,2 -binaphthyl/1,2 -binaph- 3 Methods thyl) (Li et al. 2012a) have been proposed as maturity indicators. In addition, some maturity indicators associated All rocks were ground into powder in a crusher to \80 with aromatic compounds including phenylphenanthrene mesh. The TOC content was measured on an LECO CS- ratios have also been used as frictional stress indicators 230 carbon/sulfur analyzer. The vitrinite reflectance values (Polissar et al. 2011). (%) were measured on polished rock blocks using a Leitz Previous studies mainly focused on the formation and MPV-microscopic photometer. application of PhPs in maturation assessment. This paper To extract soluble bitumen, the powder was processed reported the occurrence of PhPs in Ordovician oils, for 24 h in a Soxhlet apparatus using 400 mL of dichlor- Mesozoic lacustrine sedimentary rocks, and related oils omethane and methanol as the solvent (93:7, v:v). from the Tarim Basin, NW China. Their potential signifi- Asphaltenes were removed from approximately 20–50 mg cance to the depositional environment and lithology of oils and bitumen by precipitation using 50 mL of n-hexane source rocks and application in oil-to-source correlation in and then fractionated by liquid chromatography using oil petroleum system are discussed. The result can further alumina/silica gel columns into saturated and aromatic broaden the geochemical significance and application of hydrocarbons using 30 mL n-hexane and 20 mL dichlor- phenylphenanthrenes in sedimentary rocks and related oils. omethane: n-hexane (2:1, v:v) as respective eluents (Fang et al. 2015). The GC–MS analyses of the aromatic fractions were 2 Samples and geological settings performed on an Agilent 5975i GC–MS system equipped with an HP-5MS (5 %-phenylmethylpolysiloxane)-fused A total of eight cores and outcrop samples were collected silica capillary column (60 m 9 0.25 mm i.d., with a 0.25- from the Tarim Basin, NW China. Two cores were sampled lm film thickness). The GC operating conditions were as from Well S5, which is located in the Yakela Faulted Uplift follows: the temperature was held initially at 80 C for 123 Kuzigongsu Maigaiti Slope Tazhong Uplift Southwestern Depression Pet. Sci. (2016) 13:183–191 185 Ta ri m Basin 0 80 km Ku1 Beijing QL1 Kuqa Depression S3 YD2 China S5 RP8 YL1 JY1 Manjiaer Depression Awati Depression Bachu Uplift YL1 Well Outcrop profile Fault Primary structure belt Secondary structure belt Fig. 1 Map showing the major tectonic terrains in the Tarim Basin (NW China) and the locations of sampled wells and profiles 1 min, increased to 310 C at a rate of 3 C/min, and then present in quite low concentration or below detection limit kept isothermal for 16 min. Helium was used as the carrier in oils (Figs. 3, 4). However, it seems abundant in some gas. The injector temperature was set to 300 C. The MS was rocks and coals (Figs. 2c, 4a, b e). operated in the electron impact (EI) mode with ionization The distribution of arylated homologues of phenan- energy of 70 eV, and a scan range of m/z 50–600 Da. threnes (phenylphenanthrenes) is shown in Fig. 2.In addition, their binaphthyl (BiN) isomers were also detected in oils and rock extracts. The elution sequence of m/z 254 4 Results and discussion isomers on an HP-5MS capillary column is as follows: 1,1 - 0 0 BiN, 4-PhP, 9-PhA, 1,2 -BiN, 9-PhP, 1-PhP, 3-PhP, 2,2 - 4.1 Identification of phenylphenanthrenes BiN, 2-PhP, and 2-PhA. The 1-PhA isomer may co-elute and methylphenanthrenes with 1,2 -BiN on HP-5MS column, but it is typically absent in geochemical samples (Rospondek et al. 2009). The The identification and elution order of all isomers of isomers 3-PhP, 2-PhP, and 2,2 -BiN are typically present in methylphenanthrenes (MPs), phenylphenanthrenes (in- higher abundance relative to other PhP and BiN isomers. cluding their isomers: phenylanthracene and binaphthyl) were determined by the comparison of their mass spectra 4.2 Depositional environment and lithologies and standard retention indices (I ) with those reported of crude oils and source rocks HP-5MS in literature (Lee et al. 1979; Rospondek et al. 2009). Figure 2 shows the chemical structures of MPs and PhPs Previous studies suggested that oils in wells Ku1 and QL1 and the mass chromatograms (m/z 178, 192, 254) of aro- of the Kuqa Depression and wells YD2 and S3 of the Tabei matic fractions of selected sediment extracts in this study. Uplift (Fig. 1) are of typical lacustrine mudstone origin (Li The methyl and phenyl substitution pattern on parent rings et al. 2004; Xiao et al. 2004; Song et al. 2015). Oils from is indicated on the corresponding peaks (Fig. 2). Ordovician carbonate reservoirs were derived from Paleo- Phenanthrene and its alkylated homologues are impor- zoic carbonate source rocks (Zhang and Huang 2005; tant polycyclic aromatic hydrocarbons (PAHs) and present Wang et al. 2008; Chang et al. 2013). in significant concentrations in crude oils and sedimentary Dibenzothiophene, dibenzofuran, and their alkylated rock extracts. Four methylphenanthrene isomers and one homologues are effective molecular markers in inferring methylanthracene isomer (2-methylanthracene: 2-MA) depositional environment, maturation assessment and in trac- were identified in all rocks and oils in this study. The ing oil charging pathways (Bao et al. 1996;Wang etal. 2014; elution order of the m/z 192 isomers is as follows: 3-MP, Li et al. 2008; Zhang and Philp. 2010;Liet al. 2011, 2014). A 2-MP, 2-MA, 9-MP, and 1-MP. The isomer 2-MA is cross-plot of alkyldibenzothiophene/alkyldibenzofuran ratio Luntai Uplift Tabei Uplift Tanggu Depression Kalpin Uplift Southeastern Uplift Southeastern Depression 186 Pet. Sci. (2016) 13:183–191 Table 1 Bulk properties and selected geochemical parameters for oils and rocks in this study Sample Fm. Description TOC, % R , % Methylphenanthrene 3-PhP/ Pr/ ADBT/ C DiaH/ Ts/(Ts ? o 30 no. index (MPI1) 3-MP Ph ADBF C H Tm) YD2 Cretaceous Oil, Tabei Uplift – – 0.51 0.12 2.17 0.54 0.48 0.67 S3 Cretaceous Oil, Yakela Faulted Uplift – – 1.11 0.09 1.63 0.33 0.92 0.66 Ku1 Jurassic Oil, Kuqa Depression – – 0.13 0.17 1.84 0.26 0.50 0.55 QL1 Paleogene Oil, Kuqa Depression – – 0.66 0.60 1.79 0.48 0.64 0.63 RP10 Ordovician Oil, Halahatang Sag – – 0.78 0.03 0.81 7.52 0.09 0.37 RP4 Ordovician Oil, Halahatang Sag – – 0.38 0.01 0.76 8.06 0.08 0.42 RP3013 Ordovician Oil, Halahatang Sag – – 0.96 0.03 0.92 9.06 0.12 0.53 RP11 Ordovician Oil, Halahatang Sag – – 0.78 0.02 0.97 6.71 0.12 0.45 RP8 Ordovician Oil, Halahatang Sag – – 0.87 0.03 0.75 10.5 0.12 0.45 JY1 Ordovician Oil, Halahatang Sag – – 0.96 0.02 0.83 7.16 0.12 0.58 JY7 Ordovician Oil, Halahatang Sag – – 0.92 0.02 1.04 9.06 0.09 0.49 JY3 Ordovician Oil, Halahatang Sag – – 0.70 0.02 1.03 8.61 0.09 0.45 XK5 Ordovician Oil, Halahatang Sag – – 0.85 0.02 0.82 6.81 0.10 0.42 XK4 Ordovician Oil, Halahatang Sag – – 0.71 0.01 0.97 5.39 0.08 0.40 XK7 Ordovician Oil, Halahatang Sag – – 0.79 0.03 0.81 7.69 0.09 0.29 XK9005 Ordovician Oil, Halahatang Sag – – 0.94 0.01 1.05 9.83 0.08 0.46 Ha601 Ordovician Oil, Halahatang Sag – – 0.72 0.02 0.88 5.63 0.17 0.44 Ha7-1 Ordovician Oil, Halahatang Sag – – 0.80 0.01 1.00 9.08 0.17 0.43 Ha8 Ordovician Oil, Halahatang Sag – – 0.70 0.02 0.98 6.52 0.12 0.37 Ha13-6 Ordovician Oil, Halahatang Sag – – 0.74 0.01 1.01 6.84 0.11 0.46 TP12-8 Ordovician Oil, Akekule – – 0.89 0.03 0.91 2.72 0.08 0.49 TP14 Ordovician Oil, Akekule – – 0.65 0.02 0.87 10.10 0.06 0.45 S5 Triassic Mudstone, core, 5400.8 m 0.71 0.74 0.48 0.11 1.26 0.17 0.65 0.85 S5 Triassic Mudstone, core, 5405.4 m 0.73 0.75 0.42 0.10 1.21 0.75 n.d. 0.87 Ku-13 Jurassic Sandy mudstone, outcrop, 1.64 1.10 0.72 0.17 1.56 0.47 1.55 0.76 Kuzigongsu Ku-18 Jurassic Sandy mudstone, outcrop, 2.02 0.99 0.64 0.16 2.10 0.22 2.97 0.86 Kuzigongsu Ku-26 Jurassic Sandy mudstone, outcrop, 3.53 0.94 0.19 0.98 1.59 0.12 6.71 0.96 Kuzigongsu Ku-30 Jurassic Sandy mudstone, outcrop, 3.27 0.93 0.22 0.90 2.00 0.10 4.48 0.92 Kuzigongsu YL1 Jurassic Coal, core, 2878.0 m 38.4 0.51 0.35 0.33 3.77 0.50 n.d. n.d. KCH-01 Triassic Mudstone, outcrop, 1.12 0.26 1.44 2.08 0.31 n.d. 0.88 Kuchehe n.d.: no data (ADBT/ADBF) versus pristane/phytane ratio (Pr/Ph) provides Zone 3 (Fig. 5), suggesting the mudstone lithology of their a powerful and convenient way to infer crude oil source rock source rocks. On the basis of oil-to-source correlation depositional environments and lithologies (Radke et al. 2000). results, all these oils were derived from Mesozoic lacus- The oils from Ordovician reservoirs in the Tabei Uplift were trine mudstone source rocks (e.g., Song et al. 2015). characterized by lower Pr/Ph ratio and higher ADBT/ADBF Selected Mesozoic mudstones from the Kuqa Depres- ratio (Table 1), and the data points were plotted in Zone 1A of sion and the Tabei Uplift were also analyzed. All rock the cross-plot of ADBT/ADBF versus Pr/Ph ratios, indicating samples have relatively higher Pr/Ph ratios and quite low their marine carbonate origin (Fig. 5). values of ADBT/ADBF. The points also fall into Zone 3, Oils from Jurassic and Paleogene reservoirs in the Kuqa indicating their lacustrine mudstone lithology (Fig. 5). The Depression and oils from Cretaceous reservoirs in the coal sample from Well YL1 in the eastern Tarim Basin has Tabei Uplift have relatively higher Pr/Ph values and very very high Pr/Ph ratio, which falls into Zone 4 (fluvial/ low ADBT/ADBF values. All these data points fall into deltaic carbonaceous shale and coal zone). 123 Pet. Sci. (2016) 13:183–191 187 Phenanthrene Well Yuli1, 2878 m 100 m/z 178 (a) Middle Jurassic, Coal Tarim Basin, NW China 60 5 10 1 1’ 6 7 2’ 7 10 6 8 4 5 9 Phenanthrene Anthracene 2,2’-Binaphthyl (2,2’-BiN) 9-MP 2-MP m/z 192 (b) 1-MP 3-MP CH 4 3 1’ 1 2-MA 2’ 7 10 8 9 2-Methylphenanthrene (2-MP) 1,2’-Binaphthyl (1,2’-BiN) 2,2’-BiN (c) m/z 254 3 3-PhP 7 10 2-PhP 8 9 2-Phenylphenanthrene (2-PhP) 2-PhA 40 1,2’-BiN 1,1’-BiN 1-PhA 9-PhP 4-PhP 1-PhP 9-PhA 40 42 44 46 48 50 52 54 56 58 60 62 64 66 68 70 Retention time, min Fig. 2 Identification of phenanthrene (m/z 178), methylphenanthrene and methylanthracene (m/z 192), and phenylphenanthrene, phenylan- thracene, and binaphthyl isomers (m/z 254) in sedimentary rocks and their chemical structures Therefore, the relative abundances of alkylated diben- concentrations, and 1,2 -biphenyl is commonly absent or zothiophenes to alkylated dibenzofurans and pristane to under detection limit. The 3-PhP is the dominant com- phytane confirm that the oils in the Ordovician reservoirs pound among all PhP, PhA, and BiN isomers in m/z 254 are of marine carbonate origin and the oils from Mesozoic mass chromatograms. The concentrations of PhPs are and Paleogene sandstone reservoirs in the Kuqa Depression generally lower than those of their methylated counter- and Tabei Uplift of the Tarim Basin are of lacustrine parts—MPs in all oils. Here we defined 3-PhP/3-MP to mudstone origin. indicate the relative abundance of PhPs to MPs. The oils from wells Ku1, QL1, YD2, and S3 have 3-PhP/3-MP 4.3 Distribution of PhPs and MPs in oils and source ratios higher than 0.10. However, oils from Ordovician rocks reservoirs in the Tabei Uplift, including Ha6, Repu, Xin- ken, Jinyue, and Tuofutai blocks, have extremely low Most of the phenylphenanthrene isomers were detected in concentrations of phenylphenanthrenes with 3-PhP/3-MP oils from wells Ku1, QL1, YD2, and S3 (Fig. 3a–d). They ratios lower than 0.10 (Fig. 4e, f; Table 1). are present in differing abundance in these oils. The isomer Selected Mesozoic lacustrine mudstones were also of 2,2 -biphenyl is typically present in quite low investigated to analyze the distribution patterns of PhPs and Relative abundance, % 188 Pet. Sci. (2016) 13:183–191 9-MP 2-MP m/z 192+254 (a) (a) 9-MP 3-MP m/z 192+254 Well Ku1, Oil 2-MP 1-MP Jurassic Well S5, 5400.8 m 3-MP 1-MP 3-PhP/3-MP=0.60 2,2’-BiN Upper Triassic, Mudstone 2-MA 9-PhP TOC=0.71% 3-PhP 2,2’-BiN 3-PhP/3-MP=0.11 2-PhP 2-PhP 1,2’-BiN 3-PhP 1-PhP 9-PhP 1,2’-BiN 1-PhP (b) (b) Well QL1, Oil Paleogene Well S5, 5405.4 m 3-PhP/3-MP=0.17 Upper Triassic, Mudstone TOC=0.73% 3-PhP/3-MP=0.10 (c) (c) Well YD2, Oil Ku-18, Kuzigongsu Cretaceous Middle Jurassic, Sandy mudstone 3-PhP/3-MP=0.12 TOC=2.02% 3-PhP/3-MP=0.16 Well S3, Oil (d) (d) Cretaceous Ku-30, Kuzigongsu 3-PhP/3-MP=0.09 Middle Jurassic, Sandy mudstone TOC=3.27% 3-PhP/3-MP=0.90 (e) 9-MP 1-MP (e) Well Rp8, Oil 2-MP Well YL1, 2878 m Ordovician 3-MP Middle Jurassic, Mudstone 3-PhP/3-MP=0.03 TOC=38.40% 2-MA 1-PhP 2,2’-BiN 3-PhP/3-MP=0.33 ×5 9-PhP 3-PhP 2-PhP 1,2’-BiN 2-MP 9-MP 1-MP (f) Relative retention time 3-MP Well JY1, Oil Ordovician Fig. 4 Distribution of methylphenanthrenes (m/z 192), 3-PhP/3-MP=0.02 2,2’-BiN phenylphenanthrenes (m/z 254), and their isomers in Mesozoic source ×5 1-PhP rocks in the Tarim Basin 2-PhP 3-PhP 9-PhP YD2, and S3. Therefore, the occurrence and distribution of phenylphenanthrene and methylphenanthrenes in Mesozoic Relative retention time oils and source rocks further confirmed their genetic affinity. Fig. 3 Distribution of methylphenanthrenes (m/z 192), phenylphenanthrenes (m/z 254), and their isomers in selected oils 4.4 Effect of environment and lithology from the Tarim Basin on the distribution of MPs and PhPs MPs in sedimentary rock extracts. Most of the PhP isomers and 2,2 -BiN were detected in all rocks in this study. For the Much work has been done on the occurrence and distribution lower thermodynamic stability, PhAs and 1,1 -BiN are of methylated phenanthrenes. For example, Alexander et al. generally below detection limit in this study. The ratio of (1995) demonstrated that the sedimentary methylation pro- 3-PhP/3-MP in Mesozoic lacustrine mudstones is from 0.11 cess can form some alkylphenanthrene isomers. Due to the to 1.44, which is consistent with oils from wells Ku1, QL1, ubiquitous occurrence, the methylphenanthrenes appear to Relative abundance Relative abundance Pet. Sci. (2016) 13:183–191 189 12 1.10 Mesozoic oil 1.00 Paleogene oil 0.90 10 Ordovician oil Mesozoic source rock 0.80 Zone 1C 0.70 Zone 1A: Marine; Carbonate 0.60 Zone 1B: Marine and lacustrine (sulfate-rich); Zone 1A Mixed and carbonate 0.50 Zone 1C: Lacustrine; Mixed (mature mudstone) Zone 1D: Lacustrine; Mixed (high-rank coal) Mesozoic oil 0.40 Zone 2: Lacustrine (sulfate-poor); Paleogene oil Variable lithology 0.30 Zone 3: Marine and other lacustrine; Shale Ordovician oil Zone 4: Fluvial/Deltaic; 0.20 Carbonaceous shale and coal Mesozoic rock 0.10 Zone 1B Zone 1D 0.00 0.0 0.1 0.2 0.3 0.4 0.5 0.6 0.7 0.8 0.9 1.0 1.1 1.2 1.3 1.4 1.5 Zone 2 Zone 3 Zone 4 3-PhP/3-MP 012 3 4 Pr/Ph Fig. 6 The cross-plot of Ts/(Ts ? Tm) versus 3-PhP/3-MP ratio provides a useful way to infer the depositional environment and Fig. 5 Cross-plot of alkyldibenzothiophene/alkyldibenzofuran ratio lithology of oils and related source rocks. Ts—C 18a-22,29,30- (ADBT/ADBF) versus pristane/phytane ratio (Pr/Ph) showing crude trisnorneohopane; Tm—C 17a-22,29,30-trisnorhopane oil source rock depositional environments and lithologies (after Radke et al. 2000) ([0.55) and 3-PhP/3-MP ratios ([0.10) (Fig. 6). The have limited depositional environment and lithology signifi- higher Ts/(Ts ? Tm) ratios for Mesozoic oils and source cance. They are effective molecular markers for thermal rocks are mainly attributed to a suboxic depositional maturity assessment (e.g., Radke et al. 1982; Boreham et al. environment and clay-rich lithology, because Ordovician 1988; Voigtmann et al. 1994; Szczerba and Rospondek 2010). oils sourced from Paleozoic marine source rocks have Here we use 3-PhP/3-MP to show the abundance of generally higher maturation levels than those from the phenylphenanthrenes relative to methylphenanthrenes in Mesozoic lacustrine source rocks. oils and sedimentary organic matter. The abundance of The C diahopane in sedimentary rock extracts and oils parent phenanthrene may be different for the differences in may be derived from bacterial hopanoid precursors that the input of organic matter in source rocks and/or thermal have experienced oxidation and rearrangement by clay- maturation level of sedimentary organic matter. As pro- mediated acidic catalysis. Therefore, the presence of a posed by previous studies (Marynowski et al. 2001; significant amount of C diahopane indicates bacterial Rospondek et al. 2009), the phenylation of phenanthrene is input to sediments containing clays deposited under oxic or mainly associated with an oxidizing depositional environ- suboxic environments (Peters et al. 2005). In this study, the ment. Therefore, an oxic to suboxic environment may favor C diahopane is generally present in very low concentra- the formation of phenylphenanthrenes. The cross-plot of tion in Ordovician oils (with C diahopane/C hopane 30 30 Ts/(Ts ? Tm) versus 3-PhP/3-MP is used here to investi- ratios lower than 0.20). While Mesozoic and Paleogene oils gate the effect of the depositional environment and lithol- from wells Ku1, QL1, S3, and YD2 and Mesozoic lacus- ogy on the distribution patterns of MPs and PhPs. The Ts/ trine mudstones have higher C diahopane/C hopane 30 30 (Ts ? Tm) ratio (18a-22,29,30-trisnorneohopane/(18a- ratios (Table 1). Therefore, our study suggests that the 22,29,30-trisnorneohopane ? 17a-22,29,30-tris- presence of a significant amount of phenylphenanthrenes is norhopane)) depends on both source and maturity (Mol- generally related to clay-enriched sediments deposited dowan et al. 1986). It is a reliable maturity indictor when under suboxic conditions. assessing oils from a common source of consistent organic facies (Peters et al. 2005). This ratio increases with the increasing maturity. It is sensitive to clay-catalyzed reac- 5 Conclusions tions. For example, oils from carbonate source rocks appear to have low Ts/(Ts ? Tm) ratios compared with Phenyl phenanthrenes and their isomers have been detected those from shales (e.g., Rullko¨tter et al. 1985). in oils and source rocks from the Tarim Basin, NW China. 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Published: Apr 20, 2016

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