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The chemical composition of a group of 14 refined naphthenic and paraffinic transformer-insulating oils and refinery-treated oils by
hydrocracking and hydrotreating are compared with the composition of the starting untreated North Sea naphthenic crude oil. The
crude oil has a broad carbon distribution from C7 to C40+ , and the refined oils have a more restricted distribution from approximately
C11 to C30 , optimizing in a range from C16 to C22 . Neither the naphthenic crude oil nor its refined products contain n-alkanes or
alkylcyclohexanes, but they all contain various concentrations of iso-alkanes, bicyclanes (sesquiterpanes), pentacyclic terpanes, and
polycyclic aromatic hydrocarbons (PAHs). The base mineral oil and the inhibited transformer oils also contained a suite of steranes,
similar in distribution to those in the starting crude oil. By contrast, the four samples of paraffinic transformer oils have a very different
distribution. Three of four of the samples analyzed contain n-alkanes, alkyl-cyclohexanes and bicyclanes, but no iso-alkanes, steranes
or PAH. Two of these transformer oils contain pentacyclic terpanes. Two used transformer oils contain all the families of compounds
described previously, but in different proportions. It is apparent from the data, that the chemical properties of transformer insulating
oils are a function of the crude oil chosen for refining as well as the refining practices, such as pressure, temperature, and catalysts,
used in individual refineries.
Keywords: naphthenic and paraffinic hydrocarbons, polycyclic aromatic hydrocarbons, refining procedures, crude oil composition
fail. Their performance has been improved over the years, both
as a result of development and application of better refining
techniques and by changes in equipment design which were introduced to overcome oil-associated problems (Wilson 1980).
The previously noted methodology, began to be modified after Monsanto (St. Louis, MO) discovered and began to mass
produce polychlorinated biphenyls (PCBs) in 1929, as a substitute for petroleum-based insulating fluid (Johnson et al., 2006).
However, the use of mineral oil insulating fluids continued to be
used (Broadhurst 1972) in addition to the PCB fluids (known as
askarels). As a consequence of resulting health and environmental problems (in particular as a contributing carcinogenic agent)
caused by unintentional escape of PCB from its containers, PCB
manufacture was banned in the United States in 1977.
Subsequent to the PCB ban, the choice of crude base oil
for insulating fluid became naphthene-rich oils, because of
their preferred heat transfer and low temperature characteristics
(Rouse 1998). Over the past three decades, refining technology
has improved greatly and has led to the development of both
uninhibited- and inhibited-type fluids. The former depends on
controlling refining severity to leave the natural organic components of the oil such as non-specific PAH compounds and
sulfur compounds (e.g., benzo-thiophenes) to act as oxidation
stabilizers by serving as proton donors that stop peroxide degradation. Inhibited type oils are more highly refined in a stepwise
fashion. First, the refinery removes natural oxidation inhibiters,
117
118
I. R. Kaplan et al.
Mineral-Insulating Oils
119
Figure 1. Standard testing # IEC 60296-2003 for transformer mineral insulating oils showing type of analyses performed.
120
I. R. Kaplan et al.
Figure 2. Chemical structures for steranes, terpanes, monoaromatic and triaromatic steranes, and the iso-alkane, pristane, given as mass unit fractions
identified by mass spectrometry.
FBP is 669 F817 F. The 50% BP value also varies for each
oil.
Mineral-Insulating Oils
Table 1. Electrical insulating oils samples and manufacturers
ID Number
Sample Type
Material Type
08F1801
08F2701
08F2702
08F2703
08F2704
08F2705
08F2706
08F2707
Inhibited C
08F2708
08i2301
08i2302
08i2303
08i2304
08i2305
08i2306
Mixed crude
US2
YB3
MS2
CS2
UTO1
UTO2
PAH analysis was performed using United States Environmental Protection Agency (US EPA) method 8270M. The internal standards used for this procedure are:
1)
2)
3)
4)
5)
6)
2,4-Dichlorobenzene (d4);
Naphthalene (d8);
Acenaphthene (d10);
Phenanthrene (d10);
Chrysene (d12); and
Perylene (d12).
121
Table 2. Initial and final boiling points of samples analyzed based on simulated distillation curves and equivalent n-alkane carbon numbers
Sample#
Initial BP F
Carbon #
50% BP F
Carbon #
08F2701
08F2702
08F2703
08F2704
08F2705
08F2706
08F2707
08F2708
08F1801
08i2301
08i2302
08i2303
08i2304
08i2305
08i2306
407
465
471
410
448
442
493
215
269
421
557
534
497
425
436
12
13
13
12
11
13
14
7
12
11
16
15
14
11
13
619
606
636
580
606
622
569
769
607
684
724
651
569
613
611
19
18
20
17
18
19
17
26
18
21
23
20
17
18
18
Final BP F
857
753
805
940
817
858
727
>1328
817
801
817
729
669
695
817
Carbon #
30
21
26
37
27
31
24
>40
28
27
25
22
18
24
25
122
12
21
14
nd
14f
21(1)
27(1)
27a
nd
2m-Naphth
Compound Class
TCI
N-alkanes
Iso-alkanes
Alkyl cyclohexanes
Bicyclanes
Terpanes
Steranes
Mono-aromatic steranes
Tri-aromatic steranes
PAH
30
30
20Ph
nd
16r
32(u)
29(20)
29m
nd
C2Pyrene
Cend
17
22
21Pr
nd
16r
29(k)
27(1)
28e
nd
C4Naphth
Cmax
Cstart
11
nd
15
nd
14f
21(1)
27(1)
27a
nd
2mNaphth
Sample Name
Compound Class
TCI
N-alkanes
Iso-alkanes
Alkyl cyclohexanes
Bicyclanes
Terpanes
Steranes
Mono-aromatic steranes
Tri-aromatic steranes
PAH
27
nd
20Ph
nd
16r
30(N)
29(20)
29l
nd
C2Pyrene
Cend
16
nd
19Pr
nd
16r
24(4)
27(1)
28e
bd
C4Naphth
Cmax
Cstart
Sample Name
21
nd
20Ph
nd
16r
24(4)
nd
nd
nd
Fluorene
Cend
16
nd
19Pr
nd
16r
21(1)
nd
nd
nd
C4Naphth
Cmax
13
nd
15
nd
14f
21(1)
27(1)
nd
nd
Biphenyl
Cstart
31
nd
20Ph
nd
16r
26(6a,6b)
29(8D)
nd
nd
C2Pyrene
Cend
17
nd
19Pr
nd
16r
21(1)
27(1)
nd
nd
C4Naphth
Cmax
13
nd
16
nd
14f
21(1)
nd
nd
nd
Biphenyl
Cstart
14
nd
15
nd
14f
21(1)
27(1)
27b
nd
C2Naphth
Cstart
26
nd
20Ph
nd
16r
24(4)
nd
nd
nd
C2Pyrene
Cend
17
nd
19pr
nd
16r
21(1)
nd27(1)
nd
nd
C4Naphth
Cmax
24
nd
20Ph
nd
16r
(32(u)
29(20)
29m
nd
C2Pyrene
Cend
21
nd
19Pr
nd
16r
23(3)
27(1)
28e
nd
C4Naphth
Cmax
13
nd
15
nd
14f
21(1)
nd
nd
nd
Naphth
Cstart
12
nd
14
nd
14f
21(1)
27(1)
28e
nd
Biphenyl
Cstart
27
nd
20Ph
nd
16r
30(N)
27(1)
29m
nd
C3Pyrene
Cend
17
nd
19Pr
nd
16r
21(1)
27(!)
28e
nd
C4Naphth
Cmax
28
nd
20Ph
nd
16r
30(N)
29(20)
29m
nd
C3Pyrene
Cend
18
nd
19Pr
nd
16r
23(3)
27(1)
27a
nd
C3Naphth
Cmax
13
nd
15
nd
14f
21(1)
29(20)
27a
nd
2mNaphth
Cstart
TIC
Ion 85
Ion 113
Ion 83
Ion 123
Ion 191
Ion 217
Ion 253
Ion 231
PAH
Table 2
TIC
Ion 85
Ion 113
Ion 83
Ion 123
Ion 191
Ion 217
Ion 253
Ion 231
PAH
Table 3. Summary of starting, ending and dominant peaks in mass chromatograms for each compound class in addition to specific polycyclic aromatic hydrocarbon (PAH) compounds
123
Cstart
11
14
14
CH5
14f
21(1)
27(1)
27a
nd
2mNaphth
Sample Name
Compound Class
TCI
N-alkanes
Iso-alkanes
Alkyl cyclohexanes
Bicyclanes
Terpanes
Steranes
Mono-aromatic steranes
Tri-aromatic steranes
PAH
24
23
20Ph
CH14
16r
25(5)
28(5)
28k
nd
C3Phenenth
Cend
UTO1
08i2305
27
25
nd
CH13
16r
25(5)
nd
nd
nd
nd
17
19
19Pr
CH10
16r
21(1)
21(1)
28e
nd
C3Naphth
Cmax
22
21
nd
CH11
16r
23(3)
nd
nd
nd
nd
13
14
14
CH7
14f
21(1)
27(1)
27a
20T1
2mNaphth
Cstart
16
17
nd
nd
nd
21(1)
nd
nd
nd
nd
25
23
20Ph
CH12
16r
30(N)
29(19)
29m
27T6
C4Naphth
Cend
UTO2
08i2306
25
25
nd
nd
nd
21(1)
nd
nd
nd
nd
nd, not detected; PAH, polycyclic aromatic hydrocarbons; TCI, UTO, used transformer oils.
11
11
nd
CH5
15j
21(1)
nd
nd
nd
nd
Compound Class
TCI
N-alkanes
Iso-alkanes
Alkyl cyclohexanes
Bicyclanes
Terpanes
Steranes
Mono-aromatic steranes
Tri-aromatic steranes
PAH
17
19
19Pr
CH10
16r
23(3)
27(1)
28e
26T4
C3Naphth
Cmax
22
22
nd
nd
nd
21(1)
nd
nd
nd
nd
7
nd
14
CH1
10a
23(3)
27(1)
27a
20T1
Naphth
Cstart
15
nd
nd
CH9
15o
nd
nd
nd
nd
nd
Crude Oil
08F2708
32
nd
20Ph
CH4
16r
35(yr)
29(20)
29m
28T7
Benzo(ghi)perylene
Cend
22
nd
nd
CH14
16r
nd
nd
nd
nd
nd
19
nd
19Pr
CH1
16r
30(N)
27(1)
28e
26T4
C4Naphth
Cmax
19
nd
nd
CH12
16r
nd
nd
nd
nd
nd
TIC
Ion 85
Ion 113
Ion 83
Ion 123
Ion 191
Ion 217
Ion 253
Ion 231
PAH
14
16
nd
CH9
nd
nd
nd
nd
nd
nd
18
18
nd
CH11
nd
nd
nd
nd
nd
nd
16
16
nd
CH9
nd
nd
nd
nd
nd
nd
TIC
Ion 85
Ion 113
Ion 83
Ion 123
Ion 191
Ion 217
Ion 253
Ion 231
PAH
124
I. R. Kaplan et al.
Figure 3. Total ion current mass chromatograms. Number on each figure represents the sample analyzed (Table 1).
125
126
Mineral-Insulating Oils
Alkylcyclohexanes: m/z 83
Alkylcyclohexanes (Figure 6; Appendix 1, Table 2) are common
constituents of crude oil. In the naphthenic crude oil sample, the
narrow range extends from CH-1 to CH-4, with CH-1 dominating the other compounds (Figure 6). None of the refined products from this crude oil contain alkylcyclohexanes. However,
in the iso-paraffin transformer oil series (08i2301-08i2304) and
the two UTOs (08i2305 and 08i2306), all samples except YB3
(08i2302) contain alkylcyclohexanes.
The distribution is significantly different for each of the samples identified previously. The widest distribution is in US2
(08i2301), extending from CH5 CH13 (Figure 6), and the used
oil sample UTO1 (08i2305), extending from CH5 CH14 with a
maximum at CH-10. By contrast, the other used oil, 08i2306,
has a narrower range from CH7 CH12 (Appendix 2, Figure 3
shows additional mass chromatograms).
127
128
129
130
I. R. Kaplan et al.
Table 4. Identification and concentration (mg/kg) of polycyclic aromatic hydrocarbon (PAH) compounds present in all samples analyzed
Sample Identification by Numbers
Compound
name
Crude
Oil
08F
1801
08F
2701
08F
2702
08F
2703
08F
2704
08F
2705
08F
2706
08F
2707
08i
2305
08i
2306
Naphthalene
2-methyl naphthalene
1-methyl naphthalene
Biphenyl
C2 naphthalene
Acenaphthene
Fluorene
C3 naphthalene
C4 naphthalene
C1 fluorene
Dibenzothiophene
Phenanthrene
C1 phenanthrene
C2 phenanthrene
C1 dibenzothiophene
C2 fluorene
C2 dibenzothiophene
C3 fluorene
C3 dibenzothiophene
Pyrene
C3 phenanthrene
C1 pyrene
C4 dibenzothiophene
C4 phenanthrene
C2 pyrene
C3 Pyrene
Benz(a)anthracene
Chrysene
C1 chrysene
C2 chrysene
C3 chrysene
Benzo(b)fluoranthene
Benzo(e)pyrene
Benzo(a)pyrene
Perylene
C4 chrysene
Benzo(g,h,i)perylene
129.8
161.9
138.7
26.1
606.1
53.7
26.4
854.3
942.7
73.4
43.8
173.8
481.7
848.2
233.0
67.4
731.1
140.5
300.5
30.4
549.0
218.1
172.9
223.8
284.3
150.5
4.7
62.4
231.2
159.5
54.9
12.4
28.2
7.4
13.0
15.8
6.7
nd
nd
nd
29.0
31.5
nd
nd
61.0
147.6
nd
nd
nd
nd
17.5
nd
8.5
nd
nd
nd
nd
23.1
25.4
nd
nd
32.4
8.0
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
2.6
2.8
27.2
29.0
nd
nd
65.9
97.3
nd
nd
nd
nd
4.8
nd
7.6
nd
nd
nd
5.2
5.3
6.4
nd
nd
31.3
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
14.0
13.7
nd
nd
62.9
182.2
nd
nd
nd
nd
nd
nd
13.7
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
1.6
nd
nd
nd
15.9
nd
nd
37.1
82.8
nd
nd
nd
29.0
21.8
29.0
8.3
55.3
nd
50.2
nd
9.6
4.7
nd
nd
27.5
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
1.8
2.1
18.7
31.8
nd
nd
55.0
118.6
nd
nd
nd
nd
11.9
nd
12.0
nd
nd
nd
nd
12.9
11.9
nd
4.9
49.9
7.6
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
3.0
3.2
27.1
30.6
nd
nd
58.6
152.0
nd
nd
nd
nd
12.3
nd
12.0
nd
49.7
nd
5.5
10.2
9.3
nd
nd
37.0
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
8.9
13.5
nd
nd
26.2
47.2
nd
nd
nd
nd
nd
nd
8.1
nd
nd
nd
nd
nd
nd
nd
nd
12.3
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
6.7
nd
nd
11.5
40.4
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
3.8
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
3.3
3.3
nd
70.5
nd
nd
88.7
204.7
nd
nd
nd
nd
66.7
nd
nd
nd
nd
nd
nd
26.9
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
2.6
2.7
nd
14.4
nd
nd
22.0
18.5
nd
nd
nd
nd
n/
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
nd
Concentration,
mg/kg
7898.3
384.0
376.4
356.8
366.5
339.1
410.5
107.3
53.4
513.4
59.8
131
132
I. R. Kaplan et al.
Mineral-Insulating Oils
133
Table 6. Ratios of naphthalenic crude oil individual PAH concentrations relative to PAH in naphthenic base stock and insulating oils
Sample identification by numbers
Compound Name
08F1801
08F2701
08F2704
08F2705
08F2706
2-m naphthalene
1-m naphthalene
Biphenyl
C2 naphthalene
C3 naphthalene
C4 naphthalene
C2 phenanthrene
C2 fluorene
C3 fluorene
Pyrene
C3 phenanthrene
C1 pyrene
C4 phenanthrene
C2 pyrene
C3 pyrene
0.90
19.2
14.0
6.4
48.5
7.9
23.8
8.6
8.8
18.8
62.3
49.5
0.96
20.9
13.0
9.7
176.7
8.9
5.8
103.6
34.1
9.1
89.4
66.0
1.4
19.1
15.5
7.9
71.3
5.6
42.6
18.3
98.0
5.7
19.8
54.0
43.3
2.9
20.1
14.6
6.2
69.0
5.6
2.8
5.5
53.8
23.5
7.7
44.9
32.6
20.0
8.3
12.3
1993). They are, however, considered to be among the most stable hydrocarbons and when present in crude oil or refined oil
released in an environment their relative concentration will
increase with time (Kaplan et al., 1997). All seven of the common compounds identified in Appendix 1, Table 7, are present in
the crude oil sample (Figure 11a), but only the used oil (UTO2)
sample 08i2306 of the entire 14 refined samples displayed the
presence of triaromatic steranes (Figure 11b). Their concentration in this sample was <10% of the concentration in the crude
oil sample, but all except peak # T7 (Appendix 1, Table 7)
were present in this sample.
Polycyclic Aromatic Hydrocarbons (PAHs): Numerous m/z
values
No PAHs were detected in the 4 samples classified as originating
from iso-paraffin oils (Table 3). The eight samples, which had
undergone different refining processes at the Ergon refinery,
have PAH concentrations varying from 53.4 mg/kg to 410.5
mg/kg (Table 5). Two extremely different values were detected
in the two used transformer oils: UTO1 (08i2305 with 513.4
mg/kg) and UTO2 (08i2306 with 59.8 mg/kg).
The starting naphthenic crude oil sample (08F2708) contains
a large suite of PAH (Table 4) with a total measured concentration of 7898.3 mg/kg (Table 5). By contrast, the refined oils
contain a fraction of that in the starting crude oil (Table 5), varying from 5.2% in sample 08F2705 to 0.7% in sample 08F2707,
both manufactured by Ergon Refining. The range in the two
UTO samples is from 6.5% to 0.8%.
The distribution of individual PAH compounds is reasonably similar in the starting naphthenic crude oil and in the
refined products. The following compounds are present in all
the 08F series of samples; C2 naphthalene, C3 naphthalene,
and C4 naphthalene. The following compounds are present
in seven samples of the series; biphenyl, C2 fluorene and C2
pyrene, followed in diminishing concentration by C2 phenanthrene, C3 phenanthrene and C2 pyrene. Several other PAH
08F2707
90.5
72.3
23.3
74.8
134
I. R. Kaplan et al.
Mineral-Insulating Oils
135
produced by electric discharges. Hence, the higher their composition the more significant is their role in maintaining the initial
composition of the insulating fluid. The third property, referred
to as dielectric impulse strength, is their role in reducing short
electric shocks. It has been demonstrated that the lower the PAH
concentration in an insulating oil, the greater the capacity of the
oil in controlling arcing and rapid changes in power load. Each
refinery must therefore control the PAH concentration according to the specifications of their product. Finally it is apparent
that the hydro-treating process in the paraffinic oil refineries
136
I. R. Kaplan et al.
Discussion
This article demonstrates that the chemical compositions of
naphthenic and paraffinic transformer oils can be differentiated.
However, the analytical data also display differences within either one of the two major groups. This is due to two primary factors: crude oil composition and refining technology. First, biodegraded crude oils with depleted normal alkanes are desirable for
the production of naphthenic transformer oils and undesirable
for paraffinic oils. The rate of biodegradation, which removes
n-alkanes depends on many factors, among them, the availability of water containing nutrients and dissolved oxygen within
the storage reservoir. Hence, different locations in a single
petroleum basin may be compartmentalized, so that the availability of nutrients and oxygen could vary significantly. This could
result in insulating oils which over time of exposure to environmental conditions display differences in their chemical composition, even when the refinery procedures have not changed. To
avoid this contingency, crude oils are carefully screened in the
refinery to ensure they have the needed compound distribution
character, prior to initiating refining operations.
The second factor that affects the overall chemistry of manufactured transformer oils is the nature of the refining process
from distillation to hydro-treatment. Distillation controls the
cut-off boiling points, which in turn affects the freezing points
and viscosity of the manufactured product. The refining process depends on such parameters as pressure, temperature and
the nature of the hydro-treating catalysts. These parameters will
control the efficiency of both the hydrogenation and cracking of
large heterocyclic and polynuclear molecules. Very aggressive
reactions will result in finished transformer fluids which have a
relatively narrow distribution of hydrocarbons, as can be seen in
samples YB3 (08i2302), MS2 (08i2303) and CS2 (08i2304), in
contrast to sample US2 (08i2301). Slight or subtle changes in
chemical composition of the refined product may therefore appear if the refinery amends its refining procedures, which are not
reflected in the insulating or stability properties of the mineral
insulating oil.
Conclusions
Transformer mineral insulating oils fall into two categories;
one is naphthenic oil and the other is paraffinic oil. In this
study, fourteen refined oils from seven different refineries were
analyzed. The naphthenic fluids have a starting carbon range
from C11 C14 and an ending carbon range from C24 C37 . The
paraffinic fluids have a starting carbon range from C11 C15 and
an ending carbon range from C18 C28 .
These families can be differentiated by the following properties:
1) All the paraffinic oils contain a series of n-alkanes, but do
not contain iso-alkanes;
2) By contrast all the naphthenic oils contain iso-alkanes but
do not contain n-alkanes;
3) None of the naphthenic oils contain alkycyclohexanes,
whereas three out of the four paraffinic oils analyzed contain
them;
4) Bicyclanes (or sesquiterpanes) are present in all the naphthenic oils analyzed, but in only two of the four paraffinic
oils analyzed;
5) Naphthenic insulating oil contain a limited number of both
terpanes and steranes in concentrations depleted from the
original crude oils, whereas not all the paraffinic insulating
oils analyzed contain terpanes and steranes, and then only in
trace amounts;
6) Paraffinic oils do not contain monosteranes, whereas some
of the naphthenic oils analyzed contain a limited number of
monoaromatic steranes in concentrations either equal to, or
partially depleted relative to the crude oil;
7) Triaromatic steranes are not present in either the naphthenic
or paraffinic oils; and
8) PAH compounds are absent in all the paraffinic insulating
oils, but are present in all the naphthenic insulating oils.
The uninhibited fluids contain a wider distribution of PAH
and a higher concentration than the Inhibited oils. The chemical
properties of the transformer insulating oil families summarized
above, should allow for the differentiation of hydrocarbon fluids
in the environment.
References
American Society for Testing and Materials (ASTM). 2006. ASTM D 348700-2006: Standard Specifications for Mineral Insulating Oil Used in
Electrical Apparatus. West Conshohocken, PA: ASTM International.
ASTM. 1999. AS 1767.1: Specification for Unused Mineral Insulating
Oil for Transformer and Switchgear. West Conshohocken, PA: ASTM
International.
Broadhurst, M. G. 1972. Use and replaceability of polychlorinated
biphenyls. Environmental Health Perspectives October 1972:81102.
Canada/Canadian Standards Association (CAN/CSA). 2006. CAN/CSAC50-97: Insulating Oil, Electrical Applications for Transformers and
Switches.
Doble Engineering Company. 2006. Transformer Oil Purchase Specification (TOPS)-2006. Watertown, MA: Doble Engineering Company.
Mineral-Insulating Oils
International Electrotechnical Commission (IEC). 2003. IEC 60296: International Standard-Fluids for Electrical Application of Unused Mineral
Insulating Oils for Transformers and Switchgears.
Japanese Industrial Standard (JIS). 1993. JIS C 2320: Japanese Industrial
Standard for Electrical Insulating Oils.
Johnson, G. W., Quensea, J. F., Chiarenzelli, J. R., and Hamilton, M. C. 2006.
Polychlorinated biphenyls. In Environmental Forensics, R.D. Morrison
and B. L. Murphy, eds. 187225. San Diego, CA: Elsevier.
Kaplan, I. R., Galperin, Y., Lu, S-T., and Lee, R.-P. 1997. Forensic environmental geochemistry: Differentiation of fuel-types their sources
and release times. Organic Geochemistry 27:289317. San Diego, CA:
Elsevier.
McShane, C. P. 2000. New safety dielectric coolants for distribution and
power transformers. IEEE Industry Applications Magazine, May/June,
2432.
Peters, K. E., and Maldowan, J. M. 1993. The Biomarker Guide: Interpreting
Molecular Fossils in Petroleum and Ancient Sediments. Prentice Hall:
Englewood Cliffs, NJ.
Philp, R. P. 1985. Fossil fuel biomarkers: Applications and spectra. Amsterdam: The Netherlands: Elsevier. Methods in Geochemistry and Geophysics 23.
Rouse, T. O. 1998. Mineral insulating oil in transformers. IEEE Electrical
Insulation Magazine 14:616.
Wilson, A. C. M. 1980. Insulating Liquids: Their Uses, Manufacture and
Properties. London, UK: Institute for Electrical Engineering, Peter Peregrinus Ltd.
Detail
Iso-alkane with 10 carbon atoms
Farnesane (isoprenoid with 15 carbon atoms)
Isoprenoid with 16 carbon atoms
Pristane (isoprenoid with 19 carbon atoms)
Phytane (isoprenoid with 20 carbon atoms)
n-C8 normal alkane
n-C15 normal atkane
2,5-(2,4)-Dimethylhexane
2,3,4-Trimethylpentane
2, 3-Dimethylhexane
Alkylcyclohexane (where n indicates number of carbon
atoms in the side chain)
Detail
CH-1:
CH-2:
CH-3:
CH-4:
CH-5:
CH-6:
CH-7:
CH-8:
CH-9:
CH-10:
CH-11:
CH-12:
CH-13:
CH-14:
Methylcyclohexane
Ethylcyclohexane
Propylcylohexane
Butylcyclohexane
Pentylcyclohexane
Hexylcyclohexane
Heptylcyclohexane
Octylcyclohexane
Nonylcyclohexane
Decylcyclohexane
Undecylcyclohexane
Dodecylcyclohexane
Tridecylcyclohexane
Tetradecylcyclohexane
Formula
M.W.
2,2,3-Trimethylbicyloheptane
C10 bicycloalkane
3,3,7-Trimethylbicycloheptane
C11 decalin
Nordrimane
Nordrimane
Rearranged drimane
Rearranged drimane
Isomer of eudesmane
4(H) Eudesmane
C15 bicyclic sesquiterpane
8 (H) Drimane
C15 bicyclic sesquiterpane
C16 bicyclic sesquiterpane
C16 bicyclic sesquiterpane
8(H) Homodrimane
C10 H18
C10 H18
C10 H18
C11 H20
C14 H26
C14 H26
C15 H28
C15 H28
C15 H28
C15 H28
C15 H28
C15 H28
C15 H28
C16 H30
C16 H30
C16 H30
138
138
138
152
194
194
208
208
208
208
208
208
208
222
222
222
Appendix 1
Identity
0
1
2
3
4
5
Z4
6a
6b
7
A
B
C
D
E
F
G
H
10a
10b
1
11a
J
11b
K
C29 Ts
C30
L
Ma
Mb
N
O
13a
13b
P
Q
R
14a
S
14b
Identity
Carbon #
137
138
I. R. Kaplan et al.
Table 4. Key for tricyclic, tetracyclic, and pentacyclic terpanes (m/z 191
mass chromatograms) (Continued)
Code
Identity
Carbon #
Code
T
U
15a
15b
V
WS
WR
16a
16b
XS
XR
YS
YR
22S-17,21-30-Bishomohopane
22R-17,21-30-Bishomohopane
C35 -Tricyclic Terpane #1
C35 -Tricyclic Terpane #2
17,21-C32 -Bishomomoretane
22S-17,21-30,31,32-Trishomohopane
22R-17,21-30,31,32-Trishomohopane
C36 -Tricyclic Terpane #1
C36 -Tricyclic Terpane #2
22S-17,21-30,31,32,33-Tetrahomohopane
22R-17,21-30,31,32,33-Tetrahomohopane
22S-17,21-30,31,32,33,34-Pentahomohopane
22R-17,21-30,31,32,33,34-Pentahomohopane
32
32
35
35
32
33
33
36
36
34
34
35
35
a
b
c
d
e
f
g
h
i
j
k
l
m
Elemental
Composition
Identity
20S, 5 C27 -Monoaromatic sterane
20S, dia C27 -Monoaromatic sterane
20R, 5 C27 -Monoaromatic sterane + 20R C27 dia
MAS
20S, 5 C27 -Monoaromatic sterane
20S, 5 C28 -Monoaromatic sterane + 20S C28 dia
MAS
20R, 5 C27 -Monoaromatic sterane
20S, 5 C28 -Monoaromatic sterane
20R, 5 C28 -Monoaromatic sterane + 20R C28 dia
MAS
20S, 5 C29 -Monoaromatic sterane + 20S C29 dia
MAS
20S, 5 C29 -Monoaromatic sterane
20R, 5 C28 -Monoaromatic sterane
20R, 5 C29 -Monoaromatic sterane + 20R C29 dia
MAS
20R, 5 C29 -Monoaromatic sterane
C27 H42
C27 H42
C27 H42
C27 H42
C28 H44
C27 H42
C28 H4
C28 H44
C29 H46
C29 H46
C28 H44
C29 H46
C29 H46
Identity
1
2
3
4
5
6
7D
7
8D
8
9
9D
10
11
12
13
14D
14
15
16
17
18
19
20
21A
21B
22A
22B
23A
23B
24A
24B
13,17-diacholestane (20S)
13,17-diacholestane (20R)
13,17-diacholestane (20S)
13,17-diacholestane (20R)
24-methyl-13,17-diacholestane (20S)
24-methyl-13, 17-diacholestane (20R)
24-methyl-13, 17-diacholestane (20S)
14,17-cholestane (20S)
24-ethyl-13,17-diacholestane (20S)
14,17-cholestane (20R)
14,17-cholestane (20S)
24-methyl-13,17-diacholestane (20R)
14,17-cholestane (20R)
24-ethyl-13,17-diacholestane (20R)
24-ethyl-13,17-diacholestane (20S)
24-methyl-14,17-cholestane (20S)
24-ethyl-13,17-diacholestane (20R)
24-methyl-14,17-cholestane (20R)
24-methyl-14,17-cholestane (20S)
24-methyl-14,17-cholestane (20R)
24-ethyl-14-cholestane (20S)
24-ethyl-14,17-cholestane (20R)
24-ethyl-14,17-cholestane (20S)
24-ethyl-14,17-cholestane(20R)
24-n-Propylcholestane (20S)
4-methyl-24-ethylcholestane (20S)
4-methyl-24-ethyl-14,17-cholestane (20S)
24-n-propyl-14,17-cholestane (20S)
4-methyl-24-ethyl-14,17-cholestane (20R)
24-n-propyl-l4,17-cholestane (20R)
4-methyl-24-ethylcholestane (20R)
24-n-propylcholestane (20R)
Carbon
27
27
27
27
28
28
28
27
29
27
27
28
27
29
29
28
29
28
28
28
29
29
29
29
30
30
30
30
30
30
30
30
Identity
C20 Triaromatic sterane
C21 Triaromatic sterane
20S C26 Triaromatic sterane
20R C26 + 20S C27 -Triaromatic
steranes
20S C28 -Triaromatic sterane
20R C27 -Triaromatic sterane
20R C28 -Triaromatic sterane
Elemental Composition
C20 H20
C21 H22
C26 H32
C26 H32 + C27 H34
C28 H36
C27 H34
C28 H36
Mineral-Insulating Oils
Appendix 2
139
140
I. R. Kaplan et al.
Mineral-Insulating Oils
141
142
I. R. Kaplan et al.
Mineral-Insulating Oils
Figure 4. (Continued).
143
144
I. R. Kaplan et al.
Mineral-Insulating Oils
145