Organic Geochemistry 58 (2013) 8995

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Organic Geochemistry
journal homepage: www.elsevier.com/locate/orggeochem

Novel C26 tetracyclic degraded bicadinanes in oil sands from the HaitoubeiMaichen
Sag of the Beibuwan Basin, South China Sea
Jianping Bao a,, Cuishan Zhu a, Yurui Liu b, Wenjun Wang b, Hongyu Liu b
a
b

Key Laboratory of Oil & Gas Resource and Exploration Technology, Geochemistry Department, Yangtze University, Jingzhou 434023, Hubei, China
Geoscience Institute of Jiangsu Oil Field Corporation, SINOPEC, Yangzhou 225009, Jiangsu, China

a r t i c l e

i n f o

Article history:
Received 4 October 2012
Received in revised form 26 February 2013
Accepted 27 February 2013
Available online 13 March 2013

a b s t r a c t
Three C26 tetracyclic terpanes were detected in the saturated hydrocarbon fractions of oil sand samples
especially rich in bicadinanes W, T and R from the Oligocene Huizhou Formation in the XW-1 well in the
HaitoubeiMaichen Sag of the Beibuwan Basin. Their mass spectra show molecular ions of the three tetracyclic terpanes at m/z 358, and their key fragment ions at m/z 343 (M+-15) and m/z 315 due to loss of
an isopropyl group. These characteristics are very similar to that of C30 ciscistrans (W) and transtrans
trans (T) bicadinanes. In addition, the relative abundances of the C26 tetracyclic terpanes show an excellent positive correlation with the C30 bicadinanes W and T in 27 oil sand samples. Therefore, the three C26
tetracyclic terpanes are tentatively identied as degraded bicadinanes, which like bicadinanes, may indicate input from dammar resins and can be used to discriminate the origin of crude oils.
2013 Elsevier Ltd. All rights reserved.

1. Introduction
Bicadinanes, mainly including compounds W, T and R, are widespread in Tertiary sediments and related crude oils from Southeast
Asia (Grantham et al., 1983; Alam and Pearson, 1990; van Aarssen
et al., 1990a,b, 1991, 1992a,b, 1994; Huang et al., 2003; Zhang
et al., 2003; Zhou et al., 2003; Fu et al., 2007). Tri-, tetra- and pentacadinanes and the associated aromatic compounds have been
also detected in sediments from the Yacheng gas eld, China
(van Aarssen et al., 1992b). Compound T has been identied as
transtranstrans bicadinane (Cox et al., 1986), while the compound W is ciscistrans bicadinane (van Aarssen et al., 1990b).
Other compounds structurally related to bicadinanes, such as C31
homobicadinane (R) and C27 des-isopropyl-bicadinanes, are commonly tentatively identied based on their mass spectra (van Aarssen et al., 1991, 1992a,b; Murray et al., 1994). Seco-bicadinanes
have been detected on m/z 151 and m/z 207 mass chromatograms,
but their mass spectra are not illustrated (van Aarssen et al.,
1992a,b; Zhou et al., 2003). These hydrocarbons originated from
a cadinene polymer in dammar resins, which may depolymerise
during thermal stress (van Aarssen et al., 1992a,b). However,
Anderson and Muntean (2000) suggested a signicant contribution
from functionalized monomers based on elemental and NMR data
of the macromolecular constituents of modern dammar resin and
class II ambers. They are good indicators for the presence of dammar resins from angiosperms such as Dipterocarpaceae, that are
abundant in crude oils and sediments from Southeast Asia (van
Corresponding author. Tel.: +86 716 8060405; fax: +86 716 8060406.
E-mail address: bjp405@163.com (J. Bao).
0146-6380/$ - see front matter 2013 Elsevier Ltd. All rights reserved.
http://dx.doi.org/10.1016/j.orggeochem.2013.02.014

Aarssen et al., 1990a,b, 1994). These biomarkers can be used to discriminate the origin of crude oils (Rangel et al., 2002; Huang et al.,
2003; Zhang et al., 2003; Zhou et al., 2003; Fu et al., 2007).
In this paper, we report the occurrence of the three C26 tetracyclic terpanes, compare their mass spectra with those of bicadinanes W and T, illustrate the correlation between their relative
abundances and those of bicadinanes W and T, and tentatively
identify them as degraded bicadinanes based on their mass
spectra.
2. Samples and experimental methods
2.1. Samples and geological backgrounds
The Beibuwan Basin, located on the northern continental shelf
offshore South China Sea, consists of six sags, including the Weixinan, Haizhong, Wushi, HaitoubeiMaichen, Fushan and Leidong
(Huang et al., 2011; Fig. 1). Twenty-seven oil sand samples in the
depth range 48865020 m were collected from the Oligocene
Weizhou Formation in the XW-1 well located in the continental
part of the HaitoubeiMaichen Sag (Table 1).
In the Beibuwan Basin, the main source rocks were deposited
under lacustrine conditions in the Eocene Liushagang Formation,
which contains abundant 4-methylsteranes (Liu, 2004; Bao et al.,
2006, 2007a,b; Huang et al., 2011). The Oligocene Weizhou Formation contains thin coal beds deposited under shallow lacustrinedeltaic conditions, and this kind of source rock is locally signicant
in this basin (Ma et al., 2008). The associated condensates have
been discovered in the Haizhong Sag and their pristane/phytane
(Pr/Ph) ratios are > 6.0 (He et al., 1993).

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J. Bao et al. / Organic Geochemistry 58 (2013) 8995

Fig. 1. Location of the XW-1 well and the tectonic units of the Beibuwan Basin (modied from Huang et al., 2011).

Table 1
The oil sand samples and basic geochemical data from the XW-1 well in the HaitoubeiMaichen Sag of the Beibuwan Basin.
Depth (m)

Sat (%)

Aro (%)

Resin (%)

Asph (%)

Pr/Ph

Pr/n-C17

Ph/n-C18

4886.86
4887.5
4887.79
4888.81
4889.11
4889.21
4889.47
4889.87
4891.35
4892.42
4892.59
4892.69
4893.28
5011.97
5012.74
5012.84
5013.06
5013.88
5014.15
5014.39
5014.49
5014.89
5015.64
5016.02
5016.58
5018.67
5019.23

15.22
13.42
25.25
32.70
33.21
73.60
33.64
33.48
29.65
20.64
35.93
22.41
19.60
65.74
51.27
65.14
30.44
34.39
29.42
24.73
35.68
39.39
34.28
36.55
42.66
44.36
33.64

62.25
65.72
52.17
59.36
48.93
21.35
54.68
55.23
58.02
69.93
55.64
67.11
60.64
29.12
44.19
30.81
58.76
59.64
62.19
57.89
51.45
50.15
51.66
50.38
48.45
43.98
55.85

2.03
0.74
2.86
2.84
2.56
0.45
0.92
2.22
2.22
2.28
2.70
2.91
3.35
2.41
2.20
1.99
6.36
1.60
3.81
6.91
1.28
1.40
1.17
1.03
1.17
0.61
0.63

20.50
20.11
19.73
5.10
15.30
4.60
10.77
9.07
10.11
7.16
5.73
7.57
16.41
2.72
2.35
2.05
4.44
4.37
4.58
10.47
11.59
9.06
12.89
12.04
7.72
11.05
9.89

3.57
5.80
5.85
6.11
5.72
6.75
5.16
5.64
6.11
4.21
5.98
5.85
5.94
5.24
6.10
5.81
7.00
6.89
6.18
5.70
5.09
6.25
6.32
6.34
6.17
8.49
6.49

1.27
1.21
1.61
2.27
1.79
3.99
2.01
2.17
2.27
1.72
2.20
2.46
2.15
1.12
1.64
1.52
2.94
2.69
2.35
3.39
3.49
2.04
2.17
2.25
2.32
4.78
1.82

0.38
0.23
0.29
0.40
0.34
0.57
0.41
0.43
0.42
0.44
0.40
0.45
0.39
0.21
0.29
0.29
0.46
0.43
0.44
0.59
0.63
0.38
0.37
0.39
0.40
0.61
0.33

Note: Pr/Ph, Pr/n-C17 and Ph/n-C18 ratios were calculated by their peak areas in the m/z 57 mass chromatogram.

2.2. Experimental methods

The oil sand samples were soaked and extracted with chloroform (CHCl3) overnight at room temperature. After asphaltene

precipitation in n-hexane, the extracted oils were separated into

saturated hydrocarbon, aromatic hydrocarbon and NSO fractions
by using an aluminum/silica gel column, eluted sequentially with
n-hexane, toluene and chloroform:ethanol (v:v 1:1).

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J. Bao et al. / Organic Geochemistry 58 (2013) 8995

Gas chromatographymass spectrometry (GCMS) of the saturated hydrocarbon fractions was carried out on a HewlettPackard
Series 6890N gas chromatograph coupled to a 5975 mass selective
detector (MSD) equipped with an HP-5ms capillary column
(30 m  0.25 mm i.d.  0.25 lm lm thickness). The temperature
was held for 2 min at 50 C, increased from 50 C to 100 C at a rate
of 20 C/min, and from 100310 C at a rate of 3 C/min, and nally
held for 15.5 min at 310 C. The temperatures of the injector and
ion source were 300 C and 230 C, respectively. Helium was used
as carrier gas at a ow rate of 1.04 ml/min. The scan range was
from 50 to 550 amu using full scan and multiple ion monitoring
at 70 eV.

3. Results and discussion

3.1. Distributions of saturated hydrocarbons and bicadinanes
The extracted oils from the oil sand samples have high aromatic
content ranging from 3070% (Table 1), suggesting that they are

probably related to terrigenous organic matter. The high Pr/Ph ratios in the oil sand samples suggest that they are mainly derived
from coal-bearing source rocks deposited under oxic conditions,
consistent with the depositional environment of the Oligocene
Weizhou Formation (Ma et al., 2008).
The partial m/z 191 and m/z 217 mass chromatograms for a typical oil sand sample are shown in Fig. 2. The normal alkane series
are abundant in the saturated hydrocarbon fraction, while pristane
is much more abundant than phytane and the Pr/Ph ratio is up to
5.94. The bicadinanes W, T and R show high abundances in the partial m/z 191 and m/z 217 mass chromatograms and can even be observed in the TIC trace of the saturated hydrocarbon fraction. Their
abundances are much more than the C2735 hopanes and C2729
steranes, indicating that terrigenous organic matter, especially
dammar resins from angiosperms, made an important
contribution.
The C30 ciscistrans and transtranstrans bicadinanes, corresponding to peaks W and T in Fig. 2, respectively, are the most
abundant resin compounds in the oil sand sample as commonly
observed in the Tertiary source rocks and crude oils from Southeast

Pr

TIC

IS

Ph
W T
R

20.0

10.0

30.0

40.0

50.0

60.0

70.0

80.0

m/z 191
C24TE

C30H
C29H
R

C23T
C24T

Olea
C25T

C31H

C26T
T

C32H C33H C34H

m/z 217
W

40.0

45.0

50 .0

55 .0

60.0

6 5 .0

70.0

7 5 .0

Time (min)
Fig. 2. TIC trace from GCMS analysis of the saturated hydrocarbon fraction and the partial m/z 191 and m/z 217 mass chromatograms in an oil sand sample at 4893.28 m
depth from the XW-1 well. Pr = pristane; Ph = phytane; IS = internal standard compound for n-alkanes (n-C24D50); C23T, C24T, C25T and C26T = tricyclic terpanes; C24TE = C24
des-E-hopane; W, T and R are bicadinanes; Olea = oleanane; C2934H = ab-hopanes.

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J. Bao et al. / Organic Geochemistry 58 (2013) 8995

Fig. 3. Mass spectra of the C30 ciscistrans (W) and transtranstrans (T) bicadinanes in an oil sand sample at 4893.28 m depth in the XW-1 well. The peaks W and T are
consistent with those in Fig. 2.

Asia (Grantham et al., 1983; Alam and Pearson, 1990; van Aarssen
et al., 1990a,b, 1991, 1992a,b; Huang et al., 2003; Zhang et al.,
2003; Zhou et al., 2003; Fu et al., 2007). They have many isomers
(van Aarssen et al., 1992a,b; Murray et al., 1994) and the mass
spectra of these isomers are relatively specic. The mass spectra
of the ciscistrans bicadinane (W) and the transtranstrans
bicadinane (T) are illustrated in Fig. 3. The main differences in mass
spectra are the relative intensities of the key fragment ions, such as
at m/z 369 due to loss of an isopropyl group, at m/z 397 from loss of
a methyl group, and at the m/z 412 molecular ion.
3.2. C26 tetracyclic degraded bicadinanes
Three peaks A, B and C, eluting after C24 tricyclic terpane and
much earlier than the bicadinanes W and T, were detected in the
m/z 315 and m/z 343 mass chromatograms. Each of the three peaks
has a molecular ion M+ m/z 358, indicating that they are C26 tetracyclic terpanes (Fig. 4).
The mass spectra of the three C26 tetracyclic terpanes are illustrated in Fig. 5. The mass spectrum of peak A (Fig. 5A) has a base
peak at m/z 343 (M+-15) and the variation of the relative intensities of the key fragment ions is m/z 343 > m/z 315 > m/z 358, similar to that of bicadinane W. Peaks B and C (Fig. 5B and C) have the

same base peak at m/z 315 due to loss of an isopropyl group and
the intensity of the molecular ion at m/z 358 is much higher than
that of the fragment ion at m/z 343 (M+-15), which is consistent
with that of bicadinane T.
As mentioned above, the bicadinanes W, T and R are abnormally
abundant in the saturated hydrocarbon fractions of the oil sand
samples. Moreover, a good positive correlation exists between
the relative abundances of C26 tetracyclic terpanes (A + B + C) and
bicadinanes (W + T) in the oil sand samples (Fig. 7), suggesting that
the source of C26 tetracyclic terpanes may be similar to that of bicadinanes W and T. Therefore, we suggest that the three C26 tetracyclic terpanes are related to bicadinanes and tentatively assign them
as C26 degraded bicadinanes (C26TDB) based on their mass spectra.
Bicadinanes and related compounds in sediment extracts and
crude oils are derived from thermal decomposition of polycadinene
in dammar resins (van Aarssen et al., 1990a, 1992a,b). Anderson
and Muntean (2000) found that a signicant number of oxygencontaining functional groups occur in modern and fossil dammar
resin based on elemental and NMR data and suggested that a signicant contribution from functionalized monomers. This implies
that some of the bicadinanes in sediment extracts and crude oils
are derived from functionalized structures in dammar resin
through defunctionalization. However, in sediment extracts and

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J. Bao et al. / Organic Geochemistry 58 (2013) 8995

C23T

m/z 191
C24T

Des-A-oleanane

C25T

C24TE

C26T

B
m/z 315

Des-A-oleanane
C

m/z 343

m/z 358

42.0

43.0

44.0

45.0

46.0

47.0

48.0

49.0

50.0

51.0

52.0

53.0 54.0
Time (min)

Fig. 4. The m/z 191, m/z 315, m/z 343 and m/z 358 mass chromatograms of the C26 degraded bicadinanes AC in an oil sand sample at 4893.28 m depth from the XW-1 well.
C23T, C24T, C25T, C26T and C24TE are consistent with those in Fig. 2.

crude oils from Southeast Asia and pyrolyzates of modern and fossil dammar resins, various monomers, dimers and trimers structurally related to cadinene have been detected (van Aarssen et al.,
1990a,b, 1992a,b, 1994). The exact mechanism of formation for
those compounds from dammar resins is not clear at present. A
pathway may exist for the formation of bicadinanes and related
compounds through thermal decomposition of polycadinene or
defunctionalization of functionalized monomers in dammar resin.
The presence of the novel C26 degraded bicadinanes in the oil
sand samples suggests that the degradation of macromolecular
structures such as polycadinene or functionalized structures in
dammar resins to bicadinanes and the associated compounds in
sediment extracts and crude oils is complex. The proposed formation pathway from polycadinene or functionalized structures in
dammar resins to the C26 degraded bicadinanes is shown in
Fig. 6. Thermal stress causes the polycadinene or functionalized
structures to break down and then results in the formation of the
C26 degraded bicadinanes, probably by bond cleavage, ring closure
and hydrogenization during catagenesis. The exact pathways of
formation for the C26 degraded bicadinanes and bicadinanes will
require further work.
The relative abundance of the C26 degraded bicadinanes is much
lower than that of bicadinanes in the oil sand samples (Fig. 7). This
suggests that it is relatively more difcult to form C26 degraded
bicadinanes compared to bicadinanes during catagenesis. The
excellent positive correlation between the relative abundances of
the C26 degraded bicadinanes and bicadinanes implies that the

C26 degraded bicadinanes can also be used to indicate the contribution from dammar resins and discriminate the origin of crude oils.
In other words, they may have a similar geochemical signicance
to the bicadinanes.

4. Conclusions
Three C26 tetracyclic terpanes were detected in the oil sand
samples especially rich in bicadinanes W, T and R from the XW-1
well in the HaitoubeiMaichen Sag of the Beibuwan Basin, China.
Based on their mass spectra, the C26 tetracyclic terpanes are tentatively identied as C26 degraded bicadinanes. The good positive
correlation between the relative abundances of the C26 tetracyclic
degraded bicadinanes and the C30 bicadinanes W and T suggests
that, like bicadinanes, C26 degraded bicadinanes may indicate input
from dammar resins and can be used to discriminate the origin of
crude oils.

Acknowledgements
This study was nancially supported by the National Natural
Science Foundation of China (Grant No. 41272169). We thank
the Jiangsu Oil Corporation of SINOPEC for permitting the analytical data to be published. The constructive comments from two
anonymous reviewers, especially about the proposed formation

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J. Bao et al. / Organic Geochemistry 58 (2013) 8995

Fig. 5. Mass spectra of the C26 degraded bicadinanes. The peaks AC are consistent with those in Fig. 3.

pathway of the C26 tetracyclic terpanes from Reviewer #1 and

the name degraded bicadinanes from the Reviewer #2 greatly
helped us to understand the possible mechanism and improve

this manuscript. Prof. Chunming Zhang and Dr. Yongxian Qian

at Pittsburgh University are thanked for greatly improving the
grammar in this manuscript. Finally, we are deeply grateful for

J. Bao et al. / Organic Geochemistry 58 (2013) 8995

Polycadinene or functionalized structure

C26 degraded bicadinane

Fig. 6. The proposed pathway of the formation of C26 tetracyclic degraded

bicadinanes from dimers released from polycadinene.

bicadinanes (W+T)/C30H ratio

7.00
6.00
5.00
4.00
3.00
2.00
1.00
0.00
0.00

0.10

0.20

0.30

0.40

0.50

0.60

0.70

0.80

0.90

C26TDB/C30H ratio
Fig. 7. C26TDB/C30H vs. bicadinanes (W + T)/C30H ratios in oil sand samples from
the XW-1 well. C26TDB/C30H = C26 tetracyclic degraded bicadinanes (peaks A C) to
C30 ab-hopane; bicadinanes (W + T)/C30H = C30 bicadinanes (W + T) to C30 abhopane.

Dr. Ken Peters as Reviewer #3 for his key improvement of

grammar in this manuscript and his courage. We also thank
Ms. Wenyan Zhang and Mr. Hai He, Fei Xiao, Changchun Han
and Hongxin Liu for drafting the gures.
Associate EditorKen Peters
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