Polycyclic aromatic hydrocarbons (PAHs) are ubiquitous in the environment. They are produced naturally through forest fires with some congeners having biogenic origins. They are also produced anthropogenically through all burning or combustion processes.

1. © 2017
Chemistry Matters Inc.
Making environmental data meaningful
Multiple Lines of Evidence of PAH Fingerprinting and
Source Apportionment of Crude Oil Spills
Court D. Sandau and Phil Richards

2. © 2017
Chemistry Matters Inc.
Copyright Statement
2
All rights reserved. No part of this publication may
be reproduced, distributed, or transmitted in any
form or by any means, including photocopying,
recording, or other electronic or mechanical
methods, without the prior written permission of
Chemistry Matters Inc.
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Chemistry Matters Inc.
Oil Spills
• Stages of oil spill response
• 150,000+ L of heavy oil spilled into river during high flow season
(>2000 m3/s)
• After oil is visibly removed, can you find the oil signature?
• Sampled sediment at various locations of the river
3Dioxin Conference 2017 – Vancouver, Canada

4. © 2017
Chemistry Matters Inc.
Conventional GC Analysis of Crude Oil
Nelson et al. Environmental Forensics, 7:33–44, 2006
Unresolved Complex Matter
Straight chained alkanes
PAHs
Biomarkers
The rest
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5. © 2017
Chemistry Matters Inc.
Two-Dimensional Gas Chromatography of Crude Oil
Nelson et al. Environmental Forensics, 7:33–44, 2006
5
PAHs are present at
concentrations of 0.5 to 5%
by weight in crude oil
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6. © 2017
Chemistry Matters Inc.
Petroleum Hydrocarbon Susceptibility to
Biodegradation
C5-C6 Hydrocarbons
Olefins
n-Alkanes
Monoaromatics
Isoalkanes
Parent PAH > 2 ring
C1-alkyl PAH
C2-alkyl PAH
C3-alkyl PAH
C4-alkyl PAH
Triterpanes
Steranes
Diasteranes
Aromatic Steranes
Porphyrins
Most susceptible
Less susceptible
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Chemistry Matters Inc.
Water Solubility and Partitioning
7
Name Water solubility
(mg/L)
Organic carbon
partitioning (Koc)
Structure
Benzene 1790 80
Naphthalene 31 900
Phenanthrene 1.1 14,000
Pyrene 0.13 38,000
Benzo[a]pyrene 0.00162 549,500
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PAHs end up in
sediments

8. © 2017
Chemistry Matters Inc. 8
US EPA 16 Priority Pollutants
PAH CompoundsWhen were the 16 PAHs selected?
acenaphthene
1,2-dihydroacenaphthylene
1,8-ethylnaphthalene
Naphthyleneethylene
peri-ethylenenaphthalene
acenaphthylenenaphthalene anthracene
paranaphthalene
phenanthrene
3-Helicene
ravatite
9H-fluorene
Fluorene
2,2’-methylenebiphenyl
o-biphenylenemethane
diphenylenemethane
chrysene
1,2-benzophenanthrene
benzo(a)phenanthrene fluoranthene
Pyrene
benzo(def)phenanthrene
tetraphene
benz(a)anthracene
benzo(a)anthracene
1,2-benzanthracene
2,3-benzophenanthrene
benzo(b)phenanthrene
benzo(e)acephenanthrylene
benzo(b)fluoranthene
2,3-benzfluoranthene
3,4-benz(e)acephenanthrylene
benzo[k]fluoranthene
11,12-benzofluoranthene
2,3,1’,8’binaphthylene
dibenzo(b,jk)fluorene
8,9-benzofluoranthene
benzo(k)tetraphene
1,2:5,6-dibenzanthracene
dibenzo(a,h)anthracene
benzo(pqr)tetraphene
benzo(a)pyrene
3,4-benzpyrene
1,2-benzpyrene
benzo(def)chrysene
benzo(ghi)perylene
1,12-benzoperylene
indeno[1,2,3-cd]pyrene
1,1-(1,2-phenylene)pyrene
1,10-(o-phenylene)pyrene
2,3-o-phenylenepyrene
*Established in 1976
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9. © 2017
Chemistry Matters Inc.
16 EPA PAHs: Why?
• List created in 1976 and has not changed since
– Based primarily on water analyses
– List took one month and two meetings to create
• Criteria used to select the PAHs:
– Availability of analytical standards and measureable using 1970s
technology
– Occurred in >5% of environmental samples
– Known to have adverse effects
9
Keith, L. H. 2014. The Source of U.S. EPA's Sixteen PAH Priority Pollutants. Polycyclic Aromatic Compounds, 35, 147-160.
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10. © 2017
Chemistry Matters Inc.
Example Chromatogram of PAHs in Air in 1978
10
KATZ, M., SAKUMA, T. & HO, A. 1978. Chromatographic and spectral analysis of
polynuclear aromatic hydrocarbons - quantitative distribution in air of Ontario cities.
Environmental Science & Technology, 12, 909-915.
Analyzed by GC-FID, 12 feet long,
0.125 inch diameter Dexsil 300
80/100 mesh Chromosorb W(HP)
PYR
FLRN
B(ghi)P
BAA/CHRY
BaP
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Chemistry Matters Inc.
Expanding the List of PAHs
Alkylated-PAHs and Other PAHs
C1-Phenanthrenes
1
2
3456
7
8
9 10
CH3
C2-Phenanthrenes
Phenanthrene
CH3
CH3
CH3
H3C
CH2 CH3
C3-Phenanthrenes
C4-Phenanthrenes… (?)
CH3
CH3
CH3
CH2
H2C
CH3
(5)
(30) (?)
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Chemistry Matters Inc.
Chromatography Gets Busy
C1-DBT
C2-DBT
C3-DBT
C4-DBT
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Chemistry Matters Inc.
Expanding the List of PAHs
• Heteroatom PAHs need to be included
(collectively called NSO-heterocycles)
• Proposed 40 PAHs and 23 NSO-
heterocycles
13
Anderson JT et al., PACs, 2015, 35, 330.
Carbazole Benzothiophene Quinolinone
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14. © 2017
Chemistry Matters Inc.
Recommended List of PAHs for Oil Spill Analysis
• 16 Priority PAHs
• Dibenzothiophenes (DBT)
• Naphthobenzothiophenes – if possible (for heavy oil)
• Alkylated PAHs (C1, C2, C3, and C4 NAP, PHEN, Fluorene, PYR/FLRN,
BaA/CHRY, DBT)
• Retene (natural PAH marker)
14Dioxin Conference 2017 – Vancouver, Canada

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Chemistry Matters Inc. 15
Background PAH Exceedances
• PAH exceedances in upstream sediment samples for 2-
methylnaphthalene
0"
0.05"
0.1"
0.15"
0.2"
0.25"
AD"("01"Aug"16"
AD"("02"Aug"16"
AD"("03"Aug"16"
AD"("04"Aug"16"
AD"("05"Aug"16"
AD"("06"Aug"16"
AD"("07"Aug"16"
AD"("08"Aug"16"
AD"("09"Aug"16"
BD"("01"Aug"16"
BD"("02"Aug"16"
BD"("03"Aug"16"
BD"("04"Aug"16"
BD"("05"Aug"16"
BD"("06"Aug"16"
BD"("07"Aug"16"
BD"("08"Aug"16"
BD"("08"Aug"16"
BD"("09"Aug"16"
CD"("02"Aug"16"
CD"("03"Aug"16"
CD"("04"Aug"16"
CD"("05"Aug"16"
CD"("06"Aug"16"
CD"("07"Aug"16"
CD"("08"Aug"16"
CD"("09"Aug"16"
DD"("01"Aug"16"
DD"("02"Aug"16"
DD"("03"Aug"16"
DD"("04"Aug"16"
DD"("05"Aug"16"
DD"("06"Aug"16"
DD"("07"Aug"16"
DD"("08"Aug"16"
DD"("09"Aug"16"
ED"("01"Aug"16"
ED"("02"Aug"16"
ED"("03"Aug"16"
ED"("04"Aug"16"
ED"("05"Aug"16"
ED"("06"Aug"16"
ED"("07"Aug"16"
ED"("09"Aug"16"
BB"("11"Aug"16"
CB"("10"Aug"16"
CB"("11"Aug"16"
CB"("12"Aug"16"
CB"("13"Aug"16"
CB"("14"Aug"16"
CB"("15"Aug"16"
CB"("16"Aug"16"
Concentra)on*(mg/kg)*
22Methylnaphthalene*
Upstream"Samples"
CCME"PEL"
CCME"ISQG"
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16. © 2017
Chemistry Matters Inc. 16
Normal (parent) PAH analyses
PAH Data
Guideline Exceedances?
0%
5%
10%
15%
20%
25%
30%
NAP
2-M
e-NAPH
ACY
ACE
FLU
ANT
PHE
PYR
FLRN
BaA
CHR
BaP
DahA
Fresh Oil
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17. © 2017
Chemistry Matters Inc. 17
Extended (alkylated) PAH analyses
PAH Data
Guideline Exceedances?
Fingerprint
Sources and
history
Diagnostic
Ratios
Statistical
Analysis
Environmental Forensics
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18. © 2017
Chemistry Matters Inc. 18
PAHs – fingerprinting
0%
2%
4%
6%
8%
10%
12%
14%
16%
NAP C1 NAP C2 NAP C3 NAP C4 NAP
FLU C1 FLU C2 FLU C3 FLU
PHE/ANT
C1 PHE/ANT
C2 PHE/ANT
C3 PHE/ANT
C4 PHE/ANT
DBT C1 DBT C2 DBT C3 DBT C4 DBT FLRN/PYR
C1 FLRN/PYR
C2 FLRN/PYR
C3 FLRN/PYR
C4 FLRN/PYR
BaA/CHR
C1 BaA/CHR
C2 BaA/CHR
C3 BaA/CHR
C4 BaA/CHR
16Tan oil
0%
5%
10%
15%
20%
25%
30%
NAP
2-M
e-NAPH
ACY
ACE
FLU
ANT
PHE
PYR
FLRN
BaA
CHR
BaP
DahA
Fresh Oil
Dibenzothiophenes (DBTs) are an important group for fingerprinting oil.
Source Oil
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19. © 2017
Chemistry Matters Inc. 19
Petrogenic
Background
0%
1%
2%
3%
4%
5%
6%
7%
8%
9%
10%
NAP C1 NAP C2 NAP C3 NAP C4 NAP
FLU C1 FLU C2 FLU C3 FLU
PHE/ANT
C1 PHE/ANT
C2 PHE/ANT
C3 PHE/ANT
C4 PHE/ANT
DBT C1 DBT C2 DBT C3 DBT C4 DBT
FLRN/PYR
C1 FLRN/PYR
C2 FLRN/PYR
C3 FLRN/PYR
C4 FLRN/PYR
BaA/CHR
C1 BaA/CHR
C2 BaA/CHR
C3 BaA/CHR
C4 BaA/CHR
16-SW2CD - 23899160801714
Throughout the river there is
a background of PAHs that
has a petrogenic origin.
Background Sample 1
Background Sample 2 Background Sample 3
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20. © 2017
Chemistry Matters Inc. 20
Pyrogenic
0%
5%
10%
15%
20%
25%
30%
35%
40%
45%
NAP C1 NAP C2 NAP C3 NAP C4 NAP
FLU C1 FLU C2 FLU C3 FLU
PHE/ANT
C1 PHE/ANT
C2 PHE/ANT
C3 PHE/ANT
C4 PHE/ANT
DBT C1 DBT C2 DBT C3 DBT C4 DBT
FLRN/PYR
C1 FLRN/PYR
C2 FLRN/PYR
C3 FLRN/PYR
C4 FLRN/PYR
BaA/CHR
C1 BaA/CHR
C2 BaA/CHR
C3 BaA/CHR
C4 BaA/CHR
16-CR10 - 23899160812K10
A small number of samples present a very different PAH
origin – related to combustion.
Pyrogenic Sample
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21. © 2017
Chemistry Matters Inc. 21
Forensic Analysis of Sediment Results
Multivariate Statistical Analysis:
Hierarchical Cluster Analysis (HCA) and,
Principal Components Analysis (PCA)
• Non-specific data interpretation
• Looking for trends and groupings of samples
• Apply other specific techniques to understand origins of each
group and trends with time.
Diagnostic PAH Ratios
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22. © 2017
Chemistry Matters Inc. 22
HCA Results
1183
1184
1185
1186
1187
1188
1189
1190
1191
1192
1193
1194
1195
1196
1197
1198
1199
1200
1201
1202
1203
1204
1205
1206
1207
1208
1209
1210
1211
1212
1213
1214
1215
1216
1217
1218
1219
1220
1221
1222
1223
1224
1225
1226
1227
1228
1229
1230
1231
1232
1233
1234
1235
1236
1237
1238
1239
1240
1241
1242
1243
1244
1245
1246
1247
1248
1249
1250
1251
1252
1253
1254
1255
1256
1257
1258
1259
1260
1261
1262
1263
1264
1265
1266
1267
1268
1269
1270
1271
1272
1273
1274
1275
1276
1277
1278
1279
1280
1281
1282
1283
1284
1285
1286
1287
1288
1289
1290
1291
1292
1293
1294
1295
1296
1297
1298
1299
1300
1301
1302
1303
1304
1305
1306
1307
1308
1309
1310
1311
1312
1313
1314
1315
1316
1317
1318
1319
1320
1321
1322
1323
1324
1325
1326
1327
1328
Pyrogenic
Source
Background
Mixed (Source)
Mixed (pyro)
Mixed (Source)Different mixed groups
• Three-component
mixing (background,
pyrogenic and source
crude oil)
• Each link is a sample
• Similar samples have short
connections
• Groups of samples show
common origins
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23. © 2017
Chemistry Matters Inc. 23
Eigenvalue
20.5355
8.4174
5.1403
3.3769
3.0192
2.6165
1.8571
1.4766
1.1833
0.9030
0.7828
0.6523
20 40 60 80
-30
-20
-10
0
10
20
30
Component2(15.3%)
-30 -20 -10 0 10 20 30
Component 1 (37.3 %)
-1.0
-0.5
0.0
0.5
1.0
Component2(15.3%)
-1.0 -0.5 0.0
Component 1 (37.3 %)
Pyrogenic Source
Background
PCA Results
• Each dot is a sample
• Similar samples are
clustered together
Dioxin Conference 2017 – Vancouver, Canada
0%
1%
2%
3%
4%
5%
6%
7%
8%
9%
10%
NAP C1 N
AP C2 N
AP C3 N
AP C4 N
AP
FLU C1 FLU C2 FLU C3 FLU
PHE/ANT
C1 P
HE/ANT
C2 P
HE/ANT
C3 P
HE/ANT
C4 P
HE/ANT
DBT C1 D
BT C2 D
BT C3 D
BT C4 D
BT
FLRN/PYR
C1 FLRN/PYR
C2 FLRN/PYR
C3 FLRN/PYR
C4 FLRN/PYR
BaA/CHR
C1 B
aA/CHR
C2 B
aA/CHR
C3 B
aA/CHR
C4 B
aA/CHR
16-SA20 - 23899160807H12
0%
5%
10%
15%
20%
25%
30%
35%
40%
45%
NAP C1 NAP C2 NAP C3 NAP C4 NAP
FLU C1 FLU C2 FLU C3 FLU
PHE/ANT
C1 PHE/ANT
C2 PHE/ANT
C3 PHE/ANT
C4 PHE/ANT
DBT C1 DBT C2 DBT C3 DBT C4 DBT
FLRN/PYR
C1 FLRN/PYR
C2 FLRN/PYR
C3 FLRN/PYR
C4 FLRN/PYR
BaA/CHR
C1 BaA/CHR
C2 BaA/CHR
C3 BaA/CHR
C4 BaA/CHR
16-CR10 - 23899160812K10

24. © 2017
Chemistry Matters Inc. 24
Differentiating Origins of Petrogenic Patterns
0%
1%
2%
3%
4%
5%
6%
7%
8%
9%
10%
NAP C1 NAP C2 NAP C3 NAP C4 NAP
FLU C1 FLU C2 FLU C3 FLU
PHE/ANT
C1 PHE/ANT
C2 PHE/ANT
C3 PHE/ANT
C4 PHE/ANT
DBT C1 DBT C2 DBT C3 DBT C4 DBT
FLRN/PYR
C1 FLRN/PYR
C2 FLRN/PYR
C3 FLRN/PYR
C4 FLRN/PYR
BaA/CHR
C1 BaA/CHR
C2 BaA/CHR
C3 BaA/CHR
C4 BaA/CHR
16-SA20 - 23899160807H12
Background Source
Sulfur content is key tool
• Used for Exxon Valdez spill
Phenanthrene
Dibenzothiophene
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25. © 2017
Chemistry Matters Inc.
Exxon Valdez
25
7 of these relate to EVC
A key component is the relative
concentration of DBTs
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26. © 2017
Chemistry Matters Inc.
Exxon Valdez
26
Phenanthrene
Dibenzothiophene
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27. © 2017
Chemistry Matters Inc.
Exploring the Diagnostic Ratios
27
0
0.01
0.02
0.03
0.04
0.05
0.06
0.07
0.08
C2Dibenzothiophene
0 0.01 0.02 0.03 0.04 0.05 0.06 0.07 0.08 0.09
C2 Phenanthrene/Anthracene
Pyrogenic
Source
Background
DBT/PHEN ratios are capable of distinguishing source from other
PAH sources in the river.
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28. © 2017
Chemistry Matters Inc. 28
Apportionment Software
Positive Matrix Factorization
• Independently determines source fingerprints for PAHs from
complex data.
• Apportions the relative amount of each source in all samples.
• We use this to distinguish the amount of crude oil related PAHs in
the river samples (n=175) samples in the dataset.
• Provides guidance for selection of sampling locations.
• This is completely independent of source assignments. Thus
is also a validation method.
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29. © 2017
Chemistry Matters Inc. 29
Apportionment Factor for
Petrogenic Background
0%
2%
4%
6%
8%
10%
12%
14%
16%
NAP C1 NAP C2 NAP C3 NAP C4 NAP
FLU C1 FLU C2 FLU C3 FLU
PHE/ANT
C1 PHE/ANT
C2 PHE/ANT
C3 PHE/ANT
C4 PHE/ANT
DBT C1 DBT C2 DBT C3 DBT C4 DBT
FLRN/PYR
C1 FLRN/PYR
C2 FLRN/PYR
C3 FLRN/PYR
C4 FLRN/PYR
BaA/CHR
C1 BaA/CHR
C2 BaA/CHR
C3 BaA/CHR
C4 BaA/CHR
PMF Factor - Petrogenic Pa/ern
0%
2%
4%
6%
8%
10%
12%
NAP C1 NAP C2 NAP C3 NAP C4 NAP
FLU C1 FLU C2 FLU C3 FLU
PHE/ANT
C1 PHE/ANT
C2 PHE/ANT
C3 PHE/ANT
C4 PHE/ANT
DBT C1 DBT C2 DBT C3 DBT C4 DBT
FLRN/PYR
C1 FLRN/PYR
C2 FLRN/PYR
C3 FLRN/PYR
C4 FLRN/PYR
BaA/CHR
C1 BaA/CHR
C2 BaA/CHR
C3 BaA/CHR
C4 BaA/CHR
16-SW1AD - Petrogenic 23899160804762
Sample Data Apportionment Output
Dioxin Conference 2017 – Vancouver, Canada
Petrogenic Sample

30. © 2017
Chemistry Matters Inc. 30
Apportionment Factor for
Source
0%
2%
4%
6%
8%
10%
12%
NAP C1 NAP C2 NAP C3 NAP C4 NAP
FLU C1 FLU C2 FLU C3 FLU
PHE/ANT
C1 PHE/ANT
C2 PHE/ANT
C3 PHE/ANT
C4 PHE/ANT
DBT C1 DBT C2 DBT C3 DBT C4 DBT
FLRN/PYR
C1 FLRN/PYR
C2 FLRN/PYR
C3 FLRN/PYR
C4 FLRN/PYR
BaA/CHR
C1 BaA/CHR
C2 BaA/CHR
C3 BaA/CHR
C4 BaA/CHR
PMF Factor - 16Tan Oil Pa2ern
0%
2%
4%
6%
8%
10%
12%
NAP C1 NAP C2 NAP C3 NAP C4 NAP
FLU C1 FLU C2 FLU C3 FLU
PHE/ANT
C1 PHE/ANT
C2 PHE/ANT
C3 PHE/ANT
C4 PHE/ANT
DBT C1 DBT C2 DBT C3 DBT C4 DBT
FLRN/PYR
C1 FLRN/PYR
C2 FLRN/PYR
C3 FLRN/PYR
C4 FLRN/PYR
BaA/CHR
C1 BaA/CHR
C2 BaA/CHR
C3 BaA/CHR
C4 BaA/CHR
Product Sample
Source 1
Sample Data Apportionment Output
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Product Sample Product Sample

31. © 2017
Chemistry Matters Inc.
0
5
10
15
20
25
30
35
40
45
16-SA73 - 0 km
16-SA70 - 0 km
16-SA20 - 3.47 km
16-SA23 - 3.74 km
16-SA21 - 3.79 km
16-SA22 - 3.81 km
16-SA24 - 4.61 km
16-SA26 - 6.96 km
16-SA25 - 7.4 km
16-SA28 - 8.38 km
16-SA27 - 9.35 km
16-SA30 - 11.59 km
16-SA29 - 11.63 km
16-SA46 - 26.12 km
16-SA44 - 27.39 km
16-SA43 - 28.45 km
16-SA31 - 28.93 km
16-SA40 - 29.2 km
16-SA40 - 29.2 km
16-SA42 - 29.51 km
16-SA38 - 30.08 km
16-SA33 - 30.74 km
16-SA37 - 31.8 km
16-SA36 - 32.44 km
16-SA32 - 32.44 km
16-SA35 - 32.74 km
16-SA51 - 48.63 km
16-SA55 - 51.93 km
16-SA54 - 52.37 km
16-SA52 - 52.37 km
16-SA56 - 52.84 km
16-SA59 - 56.67 km
16-SA58 - 58.43 km
16-SA57 - 60.51 km
16-SA60 - 60.7 km
16-SA61 - 62.22 km
16-SA62 - 63.49 km
16-SA49 - 68.1 km
16-SA47 - 68.29 km
16-SA48 - 69.83 km
16-SA67 - 81.33 km
16-SA66 - 81.64 km
16-SA63 - 82.37 km
16-SA64 - 82.62 km
16-SA68 - 85.91 km
16-SA69 - 86.85 km
16-SA71 - 86.93 km
16-SA72 - 87.67 km
16-SA75D - 88.33 km
16-SA77D - 88.77 km
16-SA78D - 89.22 km
16-SA79D - 89.37 km
16-SA82D - 89.94 km
16-SA86D - 90.29 km
16-SA87D - 90.38 km
16-SA84D - 90.95 km
16-SA91 - 114.62 km
Sum PAH (mg/kg)
Bo/om Oil Samples
Crude Oil in Sediment Samples
31
Source
River Background
91 km furthest
downstream
detected oil
18 km
Downstream
73 km
Downstream 115
km
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Chemistry Matters Inc. 32
PCA including end-members
Source
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33. © 2017
Chemistry Matters Inc. 33
% Crude Calculated by Apportionment
% Source from apportionment in
agreement with PCA.
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34. © 2017
Chemistry Matters Inc. 34
% Source Calculated by Apportionment
Dioxin Conference 2017 – Vancouver, Canada
Source
Source
Source
Source

35. © 2017
Chemistry Matters Inc. 35
Conclusions
• PAHs are already present in the river due to other sources. It is
important to demonstrate where PAHs due to release may be
present
• Environmental forensics and source apportionment helped guide
locations for future monitoring and adverse effects studies
Dioxin Conference 2017 – Vancouver, Canada

36. © 2017
Chemistry Matters Inc.
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