Pergamon

Org. Geochem. Vol. 21, No. 2, pp. 115-120, 1994

Copyright 1994 Elsevier Science Ltd
Printed in Great Britain. All rights reserved
0146-6380/94 $6.00 + 0.00
The effect of maturity on the relative abundances of cadalene and
isocadalene in sediments from the Gippsland Basin, Australia
ROBERT ALEXANDER, ROBERT I. KAGI, RAJ K. SINGH and IMAM B. SOSROWIDJOJO
Centre for Petroleum and Environmental Organic Geochemistry, Curtin University of Technology,
Box U1987, GPO, Perth 6001, Western Australia
(Recei ved 2 7 Oct ober 1992; ret urned f o r revision 9 December 1992; accept ed in revised f o r m 16Augus t 1993)
Abstract--Two sedimentary sequences from the Gippsland Basin, Australia have been analysed for
cadalene and 3-isopropyl-l,6-dimethylnaphthalene (isocadalene). The relative abundance of these com-
pounds changes withqncreasing depth (maturity) of the sediments and is associated with an increase in
the abundance of 1,6-dimethylnaphthalene relative to other dimethylnaphthalene isomers. These changes
have been attributed to dealkylation and isomerization reactions of cadalene in the sediments because
analogous changes have been demonstrated in laboratory heating experiments in which cadalene was
converted into a mixture containing mainly 1,6-dimethylnaphthalene and isocadalene when heated in the
presence of aluminum smectite. The ratio of isocadalene and cadalene may be a useful maturity parameter
for some sediments and crude oils which contain these compounds.
Key wor ds - - cadal ene, 3-isopropyl-l,6-dimethylnaphthalene, isocadalene, maturity, maturity parameter,
Gippsland Basin
INTRODUCTION
The di st r i but i on of i someri c al kyl napht hal enes in
t he bi t umens ext ract ed from sedi ment s undergo
maj or changes as bur i al dept h and sedi ment t em-
per at ur e increase. For bot h di met hyl napht hal enes
and t r i met hyl napht hal enes t he or-substituted i somers
show a depl et i on relative t o t he / / - subst i t ut ed
compounds with progress in sedi ment mat ur i t y
( Al exander e t al . , 1985; Radke, 1987). These effects
have been at t r i but ed to a compl ex series of acid-
cat al ysed react i ons i nvol vi ng deal kyl at i on, al kyl at i on
and i someri zat i on t hat result in a mi xt ure of react i on
product s. I somer di st ri but i ons in the react i on pr od-
ucts appr oach t he equi l i bri um di st r i but i on in which
t he mor e st abl e fl -subst i t ut ed i somers pr edomi nat e.
These changes have been used t o devel op mat ur i t y
i ndi cat ors, based on compound rat i os, t hat can be
used t o infer the mat ur i t y of sedi ment s and, in t he
case of crude oils, t o infer the mat ur i t y of t he source
rocks at t he t i me of hydr ocar bon expul si on (cf.
Radke, 1987).
The mat ur i t y i ndi cat ors based on relative changes
in al kyl napht hal ene i somer concent rat i ons and
t hose based on similar changes in the di st r i but i on
of al kyl phenant hr ene isomers, have been widely
used al t hough some anomal i es have been r epor t ed
(Cassani e t al . , 1988). I n our experience such mat ur i t y
i ndi cat ors have shown errat i c behavi our when
appl i ed to sedi ment s cont ai ni ng abundant pl ant
remai ns of Jurassi c and younger age (Al exander
e t al . , 1992). This may be caused by a high but
vari abl e i nput to t he sedi ment s of a specific i somer
(or its precursor) t he concent rat i on of which is used
in cal cul at i ng t he mat ur i t y paramet er. For example,
very high i nput s of 1-met hyl phenant hrene are some-
times observed in sediments cont ai ni ng coni fer resins
(Al exander e t aL, 1992; Heppenhei mer e t al . , 1992);
in such cases mat ur i t y i ndi cat ors cal cul at ed using
relative concent rat i ons of this compound will be
di st ort ed. In or der to overcome such si t uat i ons,
mat ur i t y i ndi cat ors need to be f or mul at ed to include
pr oduct pr ecur sor rel at i onshi ps.
Cadal ene occurs widely in sediments (Bendorai t i s,
1974; Baset e t al . , 1980; Radke e t al . , 1984; Nobl e
e t al . , 1991). Compounds with t he cadal ene car bon
skeleton occur in pl ant s, br yophyt es and fungi
(Bordol oi e t al . , 1989). They are especially abundant
in pl ant resins, fossil resins and essential oils deri ved
from l and pl ant s ( Gr ant ham e t al . , 1983; van Aar ssen
e t al . , 1990). For these reasons the presence of
cadal ene in sediments has been i nt erpret ed as indi-
cat i ng an i nput t o the sediments of l and pl ant s
(Bendorai t i s, 1974; Radke, 1984; Simoneit, 1986).
These report s concern sedi ment ary organi c mat t er
deposi t ed aft er Jurassi c times which cor r esponds to a
per i od in evol ut i onar y hi st ory when pl ant s were
wi despread.
In this paper we r epor t on the i dent i fi cat i on of
cadal ene and 3- i sopr opyl - l , 6- di met hyi napht hal ene
(see St ruct ure 1) in a sedi ment ary sequence and
show t hat a uni f or m change occurs in t hei r relative
abundances with increase in sedi ment mat uri t y.
Because t he rel at i onshi p of these two compounds is
t hat of pr ecur sor and pr oduct for a react i on involving
i someri zat i on of the i sopr opyl group, the rat i o of the
115
116 ROBERT ALEXANDER et al.
8 1
2
3
f
I : 1 , 6 - D i m e t h y l - 4 - i s o p r o p y l n a p h t h a l e n e I 1 : 1 , 6 - D i m e t h y l - 3 - i s o p r o p y l n a p h t h a l e n e
(CADALENE) (ISOCADALENE)
Structure 1.
relative concent r at i ons of these two compounds
is pot ent i al l y a mor e reliable i ndi cat or of sedi ment
mat ur i t y t han some of t he ar omat i c mat ur i t y
i ndi cat or s current l y in use.
EXPERIMENTAL
Samples
The sampl es used in this st udy were obt ai ned
as dri l l cut t i ngs from expl or at i on wells in the
Gi pps l and Basin, Aust ral i a. The crude oils were
f r om t he same basin. Rock samples were all from
t he Lat r obe For mat i on of Lat e Cret aceous age. Thi s
f or mat i on consists of i nt er bedded coals, car bon-
aceous shales and sands of non- mar i ne origin. For
a det ai l ed descri pt i on of t he tectonic hi st ory
and basi n devel opment readers are referred
to Thomps on (1985), Hegar t y et al. (1985) and
references therein.
Preparation of cadalene and isocadalene
Cadal ene and i socadal ene were pr epar ed accordi ng
t o met hod descri bed by Ei senbraun et al. (1971).
Briefly, the synthesis of cadal ene i nvol ved a
Fr i edel - Cr af t s react i on of p- cymene and met hyl -
succinic anhydr i de t o give 4-(2-met hyl -5-i sopropyl -
phenyl )2-met hyl but anoi c acid, this aci d was cyclized
wi t h pol yphosphor i c aci d to give 2, 5-dimethyl-8-
i s opr opyl - l - t et r al one which, in t urn, was reduced t o
the cor r espondi ng al cohol with l i t hi um al umi num
hydri de and t hen dehydr at ed and ar omat i zed to give
cadal ene. Isocadal ene was synthesized using a similar
set of react i ons st art i ng with m-cymene and met hyl -
succinic anhydri de.
The spectral pr oper t i es of the synthesized com-
pounds were si mi l ar t o t hose of cadal ene and
i socadal ene r epor t ed by Adachi et al. (1981) and
Bf hl mann and Zder o (1976).
Isolation o f aromatic hydrocarbon fractions
Cr ude oil and soluble organi c mat t er ext ract ed
from dr y crushed rocks using di chl or omet hane
solvent were first di ssol ved in hexane and filtered
t hr ough a shor t col umn of act i vat ed al umi na t o
remove very pol ar compounds. The filtrate was then
subjected t o liquid chr omat ogr aphy procedures using
a Mer ck- Lobar Gr obe A (240-10) Li chr opr ep Si 60,
40-63 # m col umn coupl ed t o a Wat er s Mi l l i por e
Model 510 doubl e pi st on pump. Al kanes were eluted
from the col umn using hexane and t he ar omat i c
compounds el ut ed by reversing the flow t hr ough the
col umn using the same solvent.
Analysis o f aromatic hydrocarbon fraction
GC- MS analysis of the ar omat i c hydr ocar bon
fract i on was carri ed out using an HP 5890 capi l l ary
GC coupl ed t o an HP 5970 series MSD- comput er
dat a system, fitted with a 60 m x 0.25 mm i.d. DB-5
(J&W) fused silica capi l l ary column. The GC
was t emper at ur e pr ogr ammed from 70 to 300C at
3C/min, followed by an i sot hermal per i od of 25 min.
Typi cal MS condi t i ons were EM vol t age 1900V
el ect ron energy 70 eV and source t emper at ur e 250C.
Samples were injected using an HP 7673A injector.
Hel i um was used as carri er gas at a linear velocity
of 30 cm/s. Cadal enes were assigned by mass frag-
ment ogr aphy of t he m/ z 198 mol ecul ar i on and
by compar i son of ret ent i on times with t hose of
st andards.
Heating experiment
The al umi num smectite used in the present st udy
was mat eri al pr epar ed for an earl i er st udy (Al exander
et al., 1984) and descri bed as al umi num mont -
mori l l oni t e.
Cadal ene (1 mg) was sealed in a Pyrex glass
ampoul e of appr ox. 2.7 ml capaci t y under a ni t rogen
at mosphere with finely di vi ded al umi num smectite
(10 mg) and heat ed at 160C for 12 h. The ampoul e
was t hen cool ed, opened and the cont ent s ext ract ed
with di chl or omet hane (2 ml). The solvent was re-
moved by careful di st i l l at i on and hexane (500#1)
cont ai ni ng the ext ernal st andar d undercane (0.35/~g)
was added. An al i quot of this sol ut i on was then
anal ysed by GC techniques. The compounds rep-
resented in the resul t ant chr omat ogr am account ed
Effect of maturity of cadalene and isocadalene 117
for 75% of t he initial mass of cadal ene and consi st ed
of t he following: cadal ene (22%), i socadal ene (65%),
1,6-dimethylnaphthalene ( 4%) and uni dent i fi ed com-
pounds (9%).
R E S U L T S A N D D I S C U S S I O N
Cadal ene and 3- i sopr opyl - l , 6- di met hyl napht hal -
ene (i socadal ene) were pr epar ed usi ng est abl i shed
procedures (Ei senbraun et al., 1971) and used as
references for i dent i fi cat i on of t he two compounds
in sedi ment ext ract s and crude oil using GC- MS
techniques. Fi gur e 1 shows m/ z 198 mass chro-
mat ogr ams from a mi xt ure of the synthesized com-
pounds and from t he ar omat i c fract i on of a crude oil
(Tuna-4). The st andar ds had t he same ret ent i on t i mes
as t he compounds represent ed by the shaded peaks.
When the st andar ds were co-i nj ect ed with the
m/ z 198
a )
T U N A - 4 C R U D E OI L
Cadalene Isocadalene
b )
~ . r - ~
S T A N D A R D S
c)
HE AT I NG
E X P E RI ME NT
P
RET ENT I ON T I ME ( mi n i
Fig. 1. Partial m/z 198 mass chromatograms showing peaks
for (a) eadalene and isocadalene in a Tuna-4 crude oil (b)
a mixture of the synthesized standards and (c) the reaction
products from heating cadalene with aluminum smeetite for
12 h at 160C.
ar omat i c fract i on bot h st andar ds and unknowns co-
el ut ed using col umns coat ed wi t h bot h BP-5 (SGE,
Aust ral i a) and DB1701 (J&W, Scientific) st at i onar y
phases. The unknowns also had similar mass spect ra
t o the st andards.
Fi gur e 1 also shows an m/ z 198 mass chro-
mat ogr am from the react i on product s obt ai ned by
heat i ng cadal ene wi t h al umi num smectite at 160C
for 12 h. Cadal ene and i socadal ene were the maj or
react i on pr oduct s from the heat i ng experi ment .
The onl y ot her significant react i on pr oduct was
1, 6-dimethyinaphthalene. These results show t hat
deal kyl at i on and i someri zat i on are the most favoured
react i ons and t hat the i sopr opyl group is mor e readi l y
di spl aced t han the met hyl groups under these acid-
cl ay-cat al ysed react i on condi t i ons. Anal ysi s of these
compounds in sedi ment ary sequences suggests t hat
these react i ons may also occur under nat ur al heat i ng
condi t i ons in sediments.
Fi gur e 2 shows pl ot s of the relative abundances of
i socadal ene and cadalene, expressed as fract i on-of-
react i on for the conversi on of cadal ene to iso-
cadal ene, agai nst sampl e dept h for two wells from t he
Gi ppsl and Basin, Aust ral i a. The results show t hat
with increase in sampl e dept h an increase occurs in
the val ue of the i socadal ene/ cadal ene r at i o in bot h
wells. Because i socadal ene has not been r epor t ed
as a nat ur al product , and is absent or present in
low relative abundance in i mmat ur e sediments, we
suggest t hat it is formed in sediments from cadal ene
by i someri zat i on react i ons as a result of sedi ment
heat i ng and the cat al yt i c effects of cl ays or ot her
acidic component s of t he sediments.
Fur t her suppor t for aci d-cat al ysed react i ons of
cadal ene under nat ur al heat i ng was obt ai ned from
the di st ri but i ons of di met hyl napht hal enes in the
sedi ment samples. Fi gure 2 also shows the change in
abundance of 1, 6-di met hyl napht hal ene relative t o the
sum of 1, 3-di met hyl napht hal ene and 1,7-dimethyl-
napht hal ene. These l at t er two isomers were selected
for reference purposes for three reasons rel at ed
to anal yt i cal convenience. They co-el ut e when
chr omat ogr aphed on gas chr omat ogr aphy col umns
coat ed with BP-5 st at i onar y phase; t hey elute im-
medi at el y pr i or t o 1, 6-di met hyl napht hal ene, and t hey
occur in appr oxi mat el y si mi l ar amount s in many
samples. Fr om t he figure it is appar ent t hat the
progressi ve increase in the relative abundances of
1, 6-di met hyl napht hal ene occurs over a similar dept h
interval t o the change in relative abundance of
cadal ene and isocadalene. In this respect the obser-
vat i ons made on the react i on t ypes occurri ng in t he
sediments paral l el t hat from the l abor at or y heat i ng
experi ment descri bed above.
The change in relative abundance of cadal ene and
i socadal ene is pot ent i al l y useful as a par amet er t o
i ndi cat e mat ur i t y for pet r ol eum source rocks because
t he mat ur i t y zone in which the changes t ake pl ace
cor r esponds to t he mat ur e zone of source rocks
where oil and gas f or mat i on occurs. The mat ur i t y
118 ROBERT ALEXANDER e t al.
Dept h
( m)
1900
2400
2900
3400
3900
4400
I socadal ene
Ca d a l e n e + l s o c a d a l e n e
0.0 0.1 0.2 0.3 0.4 0.5
_ . | i i I , !
~J
,D
0
0
0
0
0
o
o
o
!
o
o
1, 6- OMN
o
1 , 7 - D M N + I , 3 - D M N
0. 7 0. 8 0. 9 1. 0 1.1 1.2 1.3 1.4
20S
2 0 S+ 2 0 R
, 1 . 1 - - . I , 1 . 1 . 1 . 1
0.0 0.1 0.2 0.3 0.4 0.5 0.6
, 1 . ! , I , i , ~ , i
0
o
0
o
i 0
I o
1 o
o
o
0
o
0
0
0
0
0
0
0
0
o
o
o
J
Fig. 2. Plots showing the change in relative abundance of isocadalene and cadalene, 1,6-dimethyl-
naphthalene and ethylcholestane diastereomers (20S, 20R) with depth for the Grunter-I (O)
and Volador-1 (O) samples.
data shown in Table 1 suggests that peak oil gener-
ation occurs in the Volador-1 well at a depth of
approx. 4000 m. At this depth the interpolated Ro
value is approx. 0.9, there is significant change in the
CPI values, and the sterane parameter is approaching
the steady state value. In the Grunter-1 well, using the
same criteria, peak oil generation occurs at a depth
of approx. 3500m. At both locations we infer
that significant oil generation probably commences
at depths approx, 500m shallower than peak oil
generation. These results suggest to us that the iso-
cadalene/cadalene parameter has values in the basin
of approx. 0.15 in the zone where initial oil formation
occurs, but its value increases markedly near peak oil
generation and continues increasing to values above
0.4 in the post-mature zone. Data for the crude oil
samples (Table 2) also support these conclusions. The
Snapper-4 crude oil is the lowest maturity crude oil
judging from the maturity values shown. The Tuna-4
and Wirrah-1 crude oils however have been released
from more mature source rocks possibly near peak
oil generation and Tuna-I represents a crude oil/
condensate from even higher maturity source rocks.
These examples serve to illustrate the wide range
of values of the cadalene/isocadalene parameter in
the zone of oil formation and suggests that it is
a sensitive measure of maturity in this important
maturity zone.
The data for MPI-I, TNR-1 and DNR-I shown in
Table 1 illustrates the variability and erratic nature
of some of the conventional aromatic maturity
indicators when applied to these sediments. The
parameter based on conversion of cadalene to iso-
cadalene may be a useful alternative for sediments of
this type. Clearly this parameter is limited in its
application to sediments that contain cadalene. These
are sediments with a significant input of land plants
a n d usually those of Jurassic age and younger.
Ef f ect of ma t ur i t y of c a da l e ne a nd i s ocadal ene
Tabl e i. Geochemi cal dat a for the sedimentary sequence
119
Sterancs~
Sample Sediment 20S
dept h (m) temp. (C) Ro(%)* CPI 20S + 20R MPI-I TNR- I DNR-1
V o l a d o r - I
3033 - - - - 1.65 0.15 0.56 0.10 2.62
3159 - - - - 1.84 0.19 - - - - - -
3280 - - 0.60 . . . . .
3315 - - - - 1.57 0.23 0.47 0.85 3.00
3370 - - 0.71 . . . . .
3405 - - - - 2.27 - - 0.53 0.55 4.13
3498 - - - - 2.29 0.21 0.54 0.66 2.53
3525 - - 0.73 2.31 0.33 0.39 0.56 1.08
3655 - - 0.76 . . . . .
3750 - - 0.82 . . . . .
3768 - - - - 1.98 0.40 - - - - - -
3820 - - - - - - 0.47 - - - - - -
3875 - - 0.85 . . . . .
3920 - - 0.89 . . . . .
3985 - - 0.83 . . . . .
4040 152* . . . . . .
4070 - - - - 1.47 0.50 0.51 0.66 2.08
4080 158" . . . . . .
4090 - - 0.88 . . . . .
4191 - - - - 1.35 0.50 0.50 0.74 2.80
4245 162" - - 1.25 0.50 0.49 0.72 2.72
4359 - - - - 1.20 0.54 - - - - - -
G r u n t e r - l
1910 - - - - 0.78 - - 0.29 1.03 7.32
2170 - - - - 1.70 0.14 0.37 1.02 0.87
2290 - - - - 1.26 0.15 0.41 0.93 3.65
2395 - - - - 1.16 0.26 0.60 0.66 3.85
2550 . . . . 0.60 1.08 5.59
2675 - - - - 2.01 0.23 0.61 - - 3.56
2775 - - - - - - 0.20 0.71 1.07 4.43
2861.3 1151" . . . . . .
2925 - - - - - - 0.23 0.84 - - - -
3019 1205 . . . . . .
3 0 3 0 - - - - 2 . 1 2 0 . 3 5 0 . 8 6 0 . 7 9 3 . 5 2
3125 - - - - 2.01 0.38 0.54 0.87 4.48
3260 - - - - i.67 0.45 0.46 - - - -
3450 - - - - 1.44 0.49 0.50 0.64 3.26
3540 - - - - 1.30 0.52 - - - - - -
3676 - - - - 1.36 0.53 0.61 0.62 3.45
3681 - - - - 1.22 0.54 0.57 - - - -
3800 1435 - - 1.19 0.57 0.60 0.72 3.75
*Dat a from St ai nfort h (1984).
#Reservoir temperature dat a from Burns e t a l . (1987).
5Estimated from temperature gradient dat a of Ozimic e t a l . (1987).
Dat a from Alexander e t a L (1991).
Definitions and met hods of measurement: Ro, vitrinite reflectance; CPI, 0.5(EC25 . . . C31/ ~C24 . . .
C30+gC25 . . . C31/ ~C24 . . . C32) (GC); steranvs, 208 and 20R diastereomers of
5a(H),14a(H),17",(H)-vthylcholestane ( m / z 2 1 7 ) ; MPI - I , (1.5 x 2-MP + 3-MP)/(0.667 x P + l-
MP+9- MP) ( m / z 1 7 8 and 192); TNR- I , 2, 3, 6-TMN/ (1, 3, 5-TMN+ 1,4,6-TMN) ( m / z l 7 0 ) ;
DNR-1, (2, 6-DMN + 2, 7- DMN) / I , 5- DMN ( m / z 1 5 6 ) ; - - , no data.
Tabl e 2. Geochemi cal mat uri t y dat a for the crude oils
Gi ppsl and oil
Acyclic alkanes Stvranes Triterpanes Aromat i c
Pr 208 Ts Mor I
CPI nCl 7 208 + 20R Tm Hop MPI-I I + C
Snapper-4 1410m 1.22 0.85"[" 0.34 0.30 0.20 0.80 0.11
Tuna-4 1400.5 m * * 0.40 0.36 0.14 0.70 0.22
Wi rrah-I 2046m 1.20 0.52 0.44 0.46 0.10 0.83 0.43
Tuna-I 2191. 5m 1.13 0.59 0.52 1.40 0.09 0.99 0.56
*Biodegraded.
t Par t l y biodegraded.
Definitions and met hods of measurement: P r / n C t T , pristane/heptadecane (C-C); CPI, 0.5(I;C25 . . .
C31fl~C24 . . . C30 + ~C25 . . . C31/ ZC24 . . . C32) (GC); st eran~, 208 and 20R diastereomers
of 5~(H),14",(H),lT~(H)-cthylcholestan ( r e ~ z 2 1 7 ) ; Ts/Tm, 18, , (H)-trisnorneohopane/17a(H)-
t ri snorhopane ( m / z 191 ); Mot / Hop, 17~ (H),21 ~ (H)-morvtane/17,, (H),21 #(H)-hopane ( i n / z 191);
MPI - I , ( I . 5x2- MP+3- MP) / ( 0. 667xP+I - MP+9- MP) ( m / z 1 7 8 and 192); I / ( I +C) ,
isoocadalene/(isocadalene + cadalene) ( m / z 198).
120 ROBERT ALEXANDER et al.
CONCLUSIONS
3- I sopr opyl - 1, 6- di met hyl napht hal ene ( i socadal ene)
has been i dent i fi ed in sedi ment s f r om t he Gi pps l and
Basi n, Aus t r al i a a nd is suggest ed t o ari se f r om
t he aci d- cat al ysed r ear r angement o f cadal ene in t he
sedi ment s.
I n t he t wo sedi ment ar y sequences st udi ed t he rel a-
t i ve a bunda nc e o f cadal ene and i socadal ene changed
wi t h i ncr ease in s ampl e dept h (mat uri t y). The r el at i ve
abundances o f cadal ene and i socadal ene in cr ude oils
f r om this basi n ar e consi st ent wi t h t hei r expul si on
f r om sedi ment s wi t hi n t he oil wi ndow.
Associate Editor--B. R. T. SIMONEIT
REFERENCES
van Aarssen B. G. K., Cox H. G., Hoogendoorn P. and
de Leeuw J. W. (1990) A cadinane biopolymer in fossil
and extant dammar resins as a source of cadinanes and
bicadinanes in crude oils from Southeast Asia. Geochem.
Cosmochim. Acta 54, 3021-3031.
Adachi K., Yokota S. and Tanaka J. (1981) Synthesis and
characterisation of alkylnaphthalenes III. 1-Isopropyl-
naphthalene and its methyl derivatives. Mere. Osaka Inst.
TechnoL Ser. A 26, 1-26.
Alexander R., Kagi R. I. and Larcher A. V. (1984) Clay
catalysis of alkyl hydrogen exchange reactions-reaction
mechanism. In Advances in Organic Geochemistry 1983
(Edited by Schenck P. A., de Leeuw J. W. and Lijmbach
G. W. M.). Org. Geochem. 6, 755-760. Pergamon Press,
Oxford.
Alexander R., Larcher A. V., Kagi R. I. and Price P. L.
(1992) An oil-source correlation study using age-specific
plant-derived aromatic biomarkers. In Biological Markers
in Sediments and Petroleum (Edited by Moldowan J. M.,
Albrecht P. and Philp R. P.), pp. 201-221. Prentice-Hall,
Englewood Cliffs, N.J.
Alexander R., Kagi R. I., Rowland S. R., Sheppard P. N.
and Chirilla T. V. (1985) The effects of thermal matu-
ration on distributions of dimethylnaphthalenes and
trimethylnaphthalenes in some Ancient sediments and
petroleums. Geochim. Cosmochim. Acta 49, 385-395.
Alexander R., Kralert P. G., Marzi R., Kagi R. I. and Evans
E. J. (1991) A geochemical method for assessment of the
thermal histories of sediments: a two-well case study from
the Gippsland Basin, Australia. APEA J. 31, 325-332.
Baset A. H., Pancirov R. J. and Ash T. R. (1980) Organic
compounds in coal: structure and origins. In Advances in
Organic Geochemistry 1979 (Edited by Douglas A. G. and
Maxwell J. R.), pp. 619-638. Pergamon Press, Oxford.
Bendoraitis J. G. (1974) Hydrocarbons of biogenic origin in
petroleum-Aromatic triterpenes and bieyclic sesquiter-
penes. In Advances in Organic Geochemistry 1973 (Edited
by Tissot B. and Bienner F.), pp. 209-224. Technip, Paris.
Brhlmann F. and Zdero C. (1976) ~ber die inhaltsstoffe yon
Heterotheca inuloides Cass. Chem. Ber. 109, 2021-2025.
Bordol oi M. , Shukl a V. S., Na t h S. C. and Sharma R. P.
(1989) Naturally occurring cadinenes. Phytochemistry 28,
2007-2037.
Burns B. J., Bos t wi ck T. R. and Emmett J. K. (1987)
Gippsland terrestrial oils---recognition of compositional
variations due to maturity and biodegradation effects.
APEA J. 27, 73~84.
Cassani F., Gallango O., Tulukdar S., Vallejos C. and
Ehrmann V. (1988) Methylphenanthrene maturity index
of marine source rock extracts and crude oils from the
Maracaibo Basin. In Advances in Organic Geochemistry
1987 (Edited by Mattavelli L. and Novelli L.). Org.
Geochem. 13, 73-80. Pergamon Press, Oxford.
Eisenbraun E. J., Hinman C. W., Springer J. M., Burnham
J. W., Chou T. S., Flanagan P. W. and Hamming M. C.
(1971) The synthesis of polyalkyl-l-tetralones and the
corresponding naphthalenes. J. Org. Chem. 36,
2480-2485.
Grantham P. J., Posthuma J. and Baak A. (1983) Triter-
panes in a number of far-eastern crude oils. In Advances
in Organic Geochemistry 1981 (Edited by Bj~roy et al.),
pp. 675-683. Wiley, New York.
Hegarty K. A., Duddy I. A., Green P. F., Gleadow A. J. W.,
Fraser I. and Weissel J. K. (1985) Regional evaluation of
the tectonic and thermal history of the Gippsland Basin.
In Proceedings of the Second South-eastern Australia
Oil Exploration Symposium (Edited by Glenie R. C.),
pp. 65-74. Petroleum Exploration Society of Australia,
Melbourne.
Heppenheimer H., Steffens K., Puttmann W. and Kalkreuth
W. (1992) Comparison of resinite-related aromatic bio-
marker distributions in Cretaceous-Tertiary coals from
Canada and Germany. Org. Geochem. 18, 273-288.
Noble R. A., Wu C. H. and Atkinson C. D. (1991)
Petroleum generation and migration from Talang Akar
coals and shales offshore N. W. Java, Indonesia. Org.
Geochem. 17, 363-374.
Ozimic S., Nicholas E., Pain L. and Vuckovic V. (1987)
Australian Petroleum Accumulations Report 3. Gippsland
Basin, Victoria. Australia Government Publishing
Service, Canberra.
Radke M. (1987) Organic geochemistry of aromatic hydro-
carbons. In Advances in Petroleum Geochemistry (Edited
by Brooks J. and Welte D.), pp. 141-207. Academic Press,
London.
Radke M., Leythaeuser D. and Teichmuller M. (1984)
Relationship between rank and composition of aromatic
hydrocarbons for coals of different origins. In Advances
in Organic Geochemistry 1983 (Edited by Schenck P. A.,
de Leeuw J. W. and Lijmbaeh G. M. W.). Org. Geochem.
6, 423-430. Pergamon Press, Oxford.
Simoneit B. R. T. (1986) Cyclic terpenoids of the geosphere.
In Biological Markers in the Sedimentary Record (Edited
by Johns R. B.), pp. 43-82. Elsevier, Amsterdam.
Stainforth J. G. (1984) Gippsland hydrocarbons--a per-
spective from the basin edge. APEA J. 24, 91-100.
Thompson B. R. (1985) The Gippsland Basin---develop-
ment and stratigraphy. In Second South -eastern Australia
Oil Exploration Symposium (Edited by Glenie R. C.),
pp. 57-64. Petroleum Exploration Society of Australia,
Melbourne.