Apppp y qlication of an Analytical Techni que for...
Transcript of Apppp y qlication of an Analytical Techni que for...
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Application of an Analytical Technique for pp y qDetermining Alkyl PAHs, Saturated Hydrocarbons and Geochemical Biomarkers
Chuck Neslund, Manager Specialty ServicesNational Environmental Monitoring Conference 2011, August 15-19, 2011
Bellevue WashingtonBellevue, Washington
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PAHs and Alkyl PAHsy
• Most important target analytes in damage assessment from petroleumdamage assessment from petroleum products
• Known to originate from 2 sourcesg- Petrogenic
- Pyrogenic
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PAHs and Alkyl PAHsy
• Can be used in forensic analysis to qualitatively fingerprint petroleumqualitatively fingerprint petroleum sample
• Crude oils contain primarily alkyl PAHs p y yand relatively smaller concentrations of unsubstituted PAHs
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What are Alkyl PAHs?y
• Parent PAHs are 2 or more fused conjugated ringsconjugated rings
naphthalene chrysene
• Alkylated PAHs are the parent PAH with• Alkylated PAHs are the parent PAH with various alkyl groups attached
2,3,5-trimethylnaphthalene7,12-dimethylchrysene
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What are Alkyl PAHs?y
• Categorized by the total number of alkyl carbon atoms presentcarbon atoms present
• A homolog group includes all of the isomers with the same number of carbon atoms
• C3 includes propyl, isopropyl, trimethyl d th l th land ethylmethyl
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What are Alkyl PAHs?y
• Parent PAHs that are isomers of other parent PAHs are combined for reportingparent PAHs are combined for reporting purposes
- phenanthrene/anthracenep /
- fluoranthene/pyrene
- benz(a)anthracene/chrysenebenz(a)anthracene/chrysene
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Why do we care?
• Traditional methods focused on the 16 Priority Pollutant PAHs identified by EPAPriority Pollutant PAHs identified by EPA
• There are hundreds if not thousands of alkylated forms that are unaccounted for in traditional methods
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Why do we care?
• Less toxicity data available for alkyl PAHs than their parent compounds
• Alkyl PAHs are more abundant and persist longer than their parent compounds
• A l i f lk l PAH i bi ti ith• Analysis of alkyl PAHs in combination with the parent compounds is a better estimation of total exposure to toxic effects of PAHs
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Method Summary
• Extraction methods are relatively standard for those used for soil and waterfor those used for soil and water
- SW-846 3510 for waters- SW-846 3546 for soils
• Alumina column clean-up used as needed• GPC and/or Silica gel for tissue samplesg
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Method Summary
• Tuning and calibration similar to 8270 SIMAlk l PAH l l t d f lti i t• Alkyl PAHs calculated from a multipoint calibration
• A representative target compound is used toA representative target compound is used to represent a homolog series for quantification
• Results generated for alkyl PAHs should be treated as semiquantitativetreated as semiquantitative
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PAHS Reported 1-Methylnaphthalene
2-Methylnaphthalene
2 6 Di th l hth l
Acenaphthene
Acenaphthylene
A th
Biphenyl
Chrysene
/ 2,6-Dimethylnaphthalene
2,3,5-Trimethylnaphthalene
Naphthobenzothiophene
Perylene
Anthracene
Benzo(a)anthracene
Benzo(a)pyrene
Benzo(b)fluoranthene
cis/trans-Decalin
Dibenz(a,h)anthracene
Dibenzofuran
Dibenzothiophene Perylene
Phenanthrene
1-Methylphenanthrene
Pyrene
Benzo(b)fluoranthene
Benzo(e)pyrene
Benzo(g,h,i)perylene
Benzo(k)fluoranthene
Dibenzothiophene
Fluoranthene
Fluorene
Indeno(1 2 3-cd)pyrene y
Retene Benzo(k)fluoranthene
Benzothiophene Indeno(1,2,3 cd)pyrene
Naphthalene
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Alkyl PAHS Reported C1-Dibenzothiophenes
C2-DibenzothiophenesC1-Naphthalenes
C2-Naphthalenes
C1-Benzo(b)thiophene
C2-Benzo(b)thiophene C2 Dibenzothiophenes
C3-Dibenzothiophenes
C4-Dibenzothiophenes
C1-Fluoranthenes/pyrenes
C2-Naphthalenes
C3-Naphthalenes
C4-Naphthalenes
C1-Fluorenes
C2-Benzo(b)thiophene
C3-Benzo(b)thiophene
C4-Benzo(b)thiophene
C1-Naphthobenzothiophenes C2-Fluoranthenes/pyrenes
C3-Fluoranthenes/pyrenes
C4-Fluoranthenes/pyrenes
C2-Fluorenes
C3-Fluorenes
C1-Phenanthrenes/Anthracenes
p p
C2-Naphthobenzothiophenes
C3-Naphthobenzothiophenes
C1-Decalin C1-Benzanthrene/chrysenes
C2-Benzantheren/chrysenes
C3-Benzanthrene/chrysenes
C4 B th / h
C2-Phenanthrenes/Anthracenes
C3-Phenanthrenes/Anthracenes
C4-Phenanthrenes/Anthracenes
C2-Decalin
C3-Decalin
C4-Decalin C4-Benzanthrene/chrysenes
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Method Summary
• To create SIM method large investment in establishing correct windowsestablishing correct windows
• Analysis of reference oils to determine alkyl PAH windows
• Requires analysis of windowing standard at start of each tune
• Alkanes added to the calibration and analysis• Alkanes added to the calibration and analysis mix
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C2-NaphthalenesMass 156, 141 amu; 10.2 to 12.8 min
200000
Abundance
Ion 156.00 (155.70 to 156.70): cg1042.D\data.ms
0
50000
100000
150000
10.20 10.40 10.60 10.80 11.00 11.20 11.40 11.60 11.80 12.00 12.20 12.40 12.60 12.800
Time-->
200000
Abundance
Ion 141.00 (140.70 to 141.70): cg1042.D\data.ms
10 20 10 40 10 60 10 80 11 00 11 20 11 40 11 60 11 80 12 00 12 20 12 40 12 60 12 800
50000
100000
150000
10.20 10.40 10.60 10.80 11.00 11.20 11.40 11.60 11.80 12.00 12.20 12.40 12.60 12.80Time-->
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Alkanes Reported n-Nonacosane
n-Triacontane
n-Decane
n-Undecane
n-Eicosane
n-Heneicosane
D n-Hentriacontane
n-Dotriacontane
n-Tritriacontane
n Tetratriacontane
n-Dodecane
n-Tridecane
n-Tetradecane
n Pentadecane
n-Docosane
n-Tricosane
n-Tetracosane
n Pentacosane n-Tetratriacontane
n-Pentatriacontane
Pristane
Phytane
n-Pentadecane
n-Hexadecane
n-Heptadecane
n-Octadecane
n-Pentacosane
n-Hexacosane
n-Heptacosane
n-Octacosane Phytane n Octadecane
n-Nonadecane
n Octacosane
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What are Geochemical Bi k ?• Complex organic compounds that are
f d i t l d h littl t
Biomarkers?
found in petroleum and show little to no change in structure from their parent molecules found in living organisms.
• Categorized into different classes, terpanes, steranes and triaromatic steroidssteroids
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What are Geochemical Bi k ?• Several reference biomarker
d i lib ti i
Biomarkers?
compounds are in calibration mixes• Biomarkers grouped according to
reference used for quantificationreference used for quantification• Analysis of reference oils key to
biomarker identification
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Biomarkers reportedA1-C20-TAS
A2-C21-TAS
A3-C26 TAS(20S)
T4-C23Diterpane
T9-C29Tricyclictriterpane(S)
T10-C29Tricyclictriterpane(R)
T20-Moretane
T21-C31-Homohopane(S)
T22-C31-Homohopane(R)
S4-Diacholestane
S5-Diacholestane
S14-Cholestane(20R)
A4-C26/C27-TAS
A5-C27-TAS(20R)
A6-TAS(20S)
A7-TAS(20R)
T11-Trisnorhopane(TS)
T12-Trisnorhopane(TM)
T13-Trisnorhopane
T13a-29,30-Bisnorhopane
T22a-Gammacerane
T26-C32-Bishomohopane(S)
T27-C32-Bishomohopane(R)
T30-C33-Trishomohopane(S)
S15-Cholestane(20S)
S22-Methylcholestane(20R)
S23-Methylcholestane(20S)
S24-MethylCholestane A7 TAS(20R) , p
T15-C29-Norhopane
T16-Norneohopane
17a(H)-diahopane
T1 C30 N
p ( )
T31-C33-Trishomohopane(R)
T32-Tetrakishomohopane(S)
T33-Tetrakishomohopane(R)
T34 P t ki h h (S)
y
S25-EthylCholestane
S26-Ethylcholestane(20R)
S27-Ethylcholestane(20S)
S28 Eth l h l tT17-C30-Normoretane
T18-C30-Oleanane
T19-C30-Hopane
T34-Pentakishomohopane(S)
T35-Pentakishomohopane(R)
S28-Ethylcholestane
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Why do we care?Why do we care?• Very useful in forensic petroleum analysis
h lk i h dwhen alkane pattern is weathered • Complements and enhances conventional
GC/FID fingerprinting capabilitiesGC/FID fingerprinting capabilities• Can be analyzed simultaneously with the
Alkyl PAHs.
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Results
• Specialized report format and electronic d h tspreadsheet
• Histograms for qualitative analysis of PAHs/Alkyl PAHsPAHs/Alkyl PAHs
• Extracted ion current profiles provided for biomarkers
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PAH/Alkyl PAH Histogram
Analyte Histogram
2500G_OIL
1000150020002500
atio
n M
G/KG
0500
Conc
entr
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Arabian Light – Total Ion Chromatogram
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Arabian Light – Mass 57 amu EICP
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Arabian Light – Mass 191 amu EICP
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Arabian Light – Mass 217 amu EICP
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Arabian Light – Mass 218 amu EICP
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Arabian Light – Mass 231 amu EICP
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Diagnostic Ratios g
Generate diagnostic ratios for specific i f d ithi th l fpairs of compounds within the classes of
compounds• IsoprenoidsIsoprenoids
n-heptadecane/pristanen-octadecane/phytane
pristane/phytane
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Diagnostic Ratios g
• Alkylated PAHs2 th l h th /1 th l h th2-methylphenanthrene/1-methylphenanthreneC2-Dibenzothiophenes/C2-PhenanthrenesRetene/C4-Phenanthrenes
• Biomarkersterpaneststeranes
triaromatic steroids
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Total Ion Chromatogram
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Mass 57 amu EICP
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Mass 191 amu EICP
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Mass 217 amu EICP
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Mass 218 amu EICP
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Mass 231 amu EICP
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AcknowledgementAcknowledgement
Richard Karam, Manager, Semivolatiles, Lancaster Laboratories, Inc.
Tim Trees, Principle Chemist, Lancaster Laboratories, Inc.
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Questions ?Questions ?