Katherine K. Stenerson, Michael Ye, Michael Halpenny, Olga Shimelis, and Leonard M. Sidisky. Supelco, Div. of Sigma-Aldrich Bellefonte, PA USA

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1 New Analytical Tools for the Determination of Persistent Organic Pollutants (POPs) in Fatty Food and Beverage Matrices Using QuEChERS Extraction/Cleanup and Gas Chromatography (GC) Analysis Katherine K. Stenerson, Michael Ye, Michael Halpenny, Olga Shimelis, and Leonard M. Sidisky Supelco, Div. of Sigma-Aldrich Bellefonte, PA USA T sigma-aldrich.com/analytical 1

2 Introduction Persistent organic pollutants (POPs) are compounds that are not easily degraded by chemical, biological, or photolytic processes. Therefore, they persist in the environment for long periods of time. POPs encompass harmful man-made compound classes such as dioxins, polychlorinated biphenyls (PCBs), chlorinated pesticides, and polyaromatic hydrocarbons (PAHs). Many of these compounds are lipophilic, and bioaccumulate in the fatty tissues of living organisms. Moving up the food chain, their concentration increases as they pass from one organism to another (1). As a result, these compounds can end up in animal-based foods such as fish, meat, and milk. 2

3 Introduction (contd.) In this work, the Quick, Easy, Cheap, Effective, Rugged, Safe (QuEChERS) sample preparation method developed by Anastassiades and Lehotay (2), was applied to the extraction and cleanup of PAHs from raw salmon and PCBs from cow s milk. Fatty foods such as fish and milk are challenging matrices in that the fats often get coextracted with the target analytes, causing interference and/or sensitivity issues during analysis. Two new zirconia-based sorbents, Supel Que Z-Sep and Z-Sep+, were evaluated for cleanup of fatty samples. Work done recently by Sapozhnikova and Lehotay on extraction and analysis of POPs in catfish, found Z-Sep effective in background removal, while obtaining good recovery and reproducibility (3). For the GC analysis portion of these applications, specially selected capillary columns were utilized to provide the necessary selectivity, temperature, and speed requirements. 3

4 Sample cleanup: Z-Sep and Z-Sep+ Z-Sep is a proprietary zirconia-coated silica. has ion-exchange groups with acidic character Z-Sep+ is a bonded C18 zirconia-coated silica. has both ion-exchange and hydrophobic functionalities on its surface Zirconia acts as a Lewis acid, binding electron donating groups such as OH found in mono and diglycerides. C18 binds fats through hydrophobic interaction. Used with zirconia, it produces a synergistic effect in enhancing fat retention. 4

5 Experimental QuEChERS Extraction and Cleanup Methods Salmon Place 5 g ground sample into 50 ml centrifuge tube. Spike with 100 ng/g target PAHs and internal standards. Let sit 30 min. Whole Cow s Milk Place 10 g milk into 50 ml centrifuge tube. Spike with 20 ng/g target PCBs. Let sit 60 min. Add 5 ml water and homogenize Add 25 ml acetonitrile, 1 g NaCl & 4 g MgSO 4. Shake for 5 min. Centrifuge samples for 5 min, 3200 rpm Remove 3 ml of extract for cleanup; shake 1 min. and centrifuge for 3 min. at 3400 rpm Separate 1 ml supernatant Proceed with GC-MS analysis Add 20 ml of 1:1 acetone:hexane, shake for 1 min. Add 1 g NaCl & 4 g MgSO 4. Shake for 3 min Centrifuge samples for 5 min, 3400 rpm Remove 1 ml of extract for cleanup; shake 1 min and centrifuge for 3 min. at 3400 rpm Separate supernatant Proceed with GC-ECD analysis 5

6 GC-MS & GC-ECD Analysis Conditions Salmon instrument: Agilent 7890/5975 GC/MS column: SPB-608, 20 m x 0.18 mm I.D., 0.18 µm oven: 60 C (1 min.), 25 C/min. to 275 C, 10 C/min. to 300 C (13 min.) temp.: 265 C carrier gas: helium, 1.5 ml/min constant det.: MSD, SIM MSD temps.: quads: 160 C, source: 240 C, transfer line: 300 C injection: 1 µl, splitless (1 min.) liner: 4 mm FocusLiner w/taper Cow s Milk instrument: Agilent 7890 GC column: SLB-5ms, 20 m x 0.18 mm I.D., 0.18 µm oven: 75 C (1 min.), 12 C/min. to 340 C, (10 min.) temp.: 250 C carrier gas: hydrogen, 1.2 ml/min constant det.: µ-ecd, 340 C injection: 1 µl, splitless (0.75 min.) liner: 4 mm FocusLiner w/taper 6

7 Summary of Experiments Samples 1. Farm raised, Atlantic salmon approx. 12% fat, uncooked spiked at 100 ng/g with PAHs 2. Whole cow s milk, 3.3% fat spiked at 20 ng/g with PCBs Cleaned samples using four different sorbents 1. Z-Sep+ 2. Z-Sep+/PSA 3. Z-Sep/MgSO 4 4. PSA/C18/MgSO 4 Compared background removal by GC-MS in scan mode, and analyte recoveries after GC-MS/SIM or GC-ECD analysis Columns selected for GC analysis 1. SPB-608, 20 m x 0.18 mm I.D., 0.18 µm: provides resolution of benzo [b], [j], [k] fluoranthene isomers and benzo [a] and [e] pyrene isomers. 2. SLB-5 ms: 20 m x 0.18 mm I.D., 0.18 µm: provides high maximum temperature for column bake-out of heavy matrix, and with hydrogen carrier can be used for faster analysis time than a standard 30 m column. 7

8 Results Background Removal GC-MS in full scan mode, analysis of cleaned and uncleaned extracts The effect of cleanup varied with matrix. For all cleanup sorbents: Salmon: significant reduction in overall background Cow s milk: reduction in level of late eluting/heavy matrix peaks Z-Sep produced the cleanest background in both salmon and milk extracts. Fewest peaks detected in salmon extracts Lowest level of heavy, late eluting matrix in cow s milk extracts (indicated by amplitude of largest peak in TICs). 40% reduction from uncleaned extract. 8

9 Background Removal Salmon (all same Y-scale) 8.00E E E+06 No cleanup 2.00E E E E E E E E+06 PSA/C E E E+06 Z-Sep+ 0.00E

10 Background Removal Salmon (all same Y-scale) (contd.) 8.00E E E+06 Z-Sep+/PSA 2.00E E E E E+06 Z-Sep 2.00E E

11 Background Removal Cow s milk (all same Y-scale) 3.00E+07 AU 1.00E E+07 No cleanup AU 0.00E E E E PSA/C18 AU 1.00E E E+07 Z-Sep

12 Background Removal Cow s milk (all same Y-scale) (contd.) AU 1.00E E E+07 Z-Sep+/PSA AU 1.00E E E+07 Z-Sep

13 Analyte Recovery PAHs from Salmon Internal standard calibration with a 5-point curve prepared in solvent used for quantitation. Z-Sep and Z-Sep+ exhibited the best recoveries overall. PSA added additional background peaks, some of which coeluted with PAH peaks in spiked extracts. These were quantitated in the blanks and subtracted from effected spikes when calculating recoveries. The lower recoveries of the last three PAHs could be due to limited solubility of these compounds in acetonitrile. 13

14 Analyte Recovery PAHs from Salmon (contd.) 130% Spike level 100 ng/g, average of 3 replicates %RSDs <10% for majority of analytes/sorbents 120% 110% 100% 90% 80% 70% 60% 50% 14 Avg. % Recovery Z-Sep+ Z-Sep+/PSA Z-Sep PSA/C18 Naphthalene 2-Methylnaphthalene 1-Methylnaphthalene Biphenyl 2,6-Dimethylnaphthalene Acenaphthlylene Acenaphthene 2,3,5-Trimethylnaphthalene Fluorene Dibenzothiophene Phenanthrene Anthracene 1-Methylphenanthrene Fluoranthene Pyrene Retene Benzo[a]anthracene Chrysene & Triphenylene Benzo[b]fluoranthene Benzo[k]fluoranthene Benzo{j}fluoranthene Benzo[e]pyrene Benzo[a]pyrene Perylene Indeno[1,2,3-cd]pyrene Dibenz[a,h]anthracene Benzo[g,h,i]perylene Chrysene and triphenylene coeluted. Recovery of these was calculated as a total of the two together.

15 Analysis of Spiked Salmon Extract, SIM Mode (Z-Sep cleanup) 1. Naphthalene-d 8 (I.S.) 2. Naphthalene 3. 2-Methylnaphthalene 4. 1-Methylnaphthalene 5. Biphenyl 6. 2,6-Dimethylnaphthalene 7. Acenaphthylene 8. Acenaphthene 9. 2,3,5-Trimethylnaphthalene 10. Fluorene 11. Dibenzothiophene Phenanthrene 13. Anthracene Methylphenanthrene 15. Fluoranthene-d 10 (I.S.) 16. Fluoranthene 17. Pyrene 18. Retene 19. Benzo[a]anthracene 20. Chrysene & Triphenylene 21. Benzo[b]fluoranthene 22. Benzo[k]fluoranthene 23. Benzo[j]fluoranthene 24. Benzo[e]pyrene 25. Benzo[a]pyrene 26. Perylene-d 12 (I.S.) 27. Perylene 28. Indeno[1,2,3-cd]pyrene 29. Dibenz[a,h]anthracene 30. Benzo[g,h,i]perylene 15

16 Analyte Recovery PCBs from Cow s Milk External standard calibration with a 5-point curve prepared in solvent was used for quantitation. Noted overall decrease in recovery with increasing weight of congener. For analyte recovery, Z-Sep showed a slight advantage over the other sorbents, especially for the heavier congeners. Otherwise, recoveries were very similar. The SLB-5ms column provided stable retention times and a high maximum temperature, which was useful for eluting heavy matrix. 16

17 Analyte Recovery PCBs from Cow s Milk (contd.) 120% 110% 100% Spike level 20 ng/g, average of 3 replicates %RSDs <10% majority of analytes/sorbents Avg. % Recovery 90% 80% 70% 60% 50% No. 28 No. 52 Z-Sep + Z-Sep PSA/C18 Z-Sep+/PSA No. No. No No. No. No. No. No. No. No. No. No. No. No. No. No. No PCB Congener 17

18 GC-ECD Analysis of Spiked Milk Extract (Z-Sep cleanup) No. 28 No. 52 No. 114 No. 118 No.156 No. 105 No.157 No.189 No. 138 No. 123 No. 167 No. 180 No. 153 No. 101 No.169 No. 81 No. 77 No. 126 No. 209 Congeners: No. 28: No. 52: No. 101: No. 81: No. 77: No. 123: No. 118: No. 114: No. 153: No. 105: 2,3',6-trichlorobiphenyl 2,2',5,5'-tetrachlorobiphenyl 2,2',4,5,5'-pentachlorobiphenyl 3,4,4',5-tetrachlorobiphenyl 3,3',4,4'-tetrachlorobiphenyl 2',3,4,4',5-pentachlorobiphenyl 2,3',4,4',5-pentachlorobiphenyl 2,3,4,4',5-pentachlorobiphenyl 2,2',4,4',5,5'-hexachlorobiphenyl 2,3,3',4,4'-pentachlorobiphenyl No. 105: No. 138: No. 126: No. 167: No. 156: No. 157: No. 180: No. 169: No. 189: No. 209: 2,3,3',4,4'-pentachlorobiphenyl 2,2',3,4,4',5'-hexachlorobiphenyl 3,3',4,4',5-pentachlorobiphenyl 2,3',4,4',5,5'-hexachlorbiphenyl 2,3,3',4,4',5-hexachlorobiphenyl 2,3,3',4,4',5'-hexachlorobiphenyl 2,2',3,4,4',5,5'-heptachlorobiphenyl 3,3',4,4',5,5'-hexachlorobiphenyl 2,3,3',4,4',5,5'-heptachlorobiphenyl 2,2',3,3',4,4',5'5',6,6'-decachlorobiphenyl 18

19 Conclusions GC-MS data indicated that of the four cleanups, Z-Sep removed the most background. This was true for both salmon and cow s milk extracts. In raw salmon, Z-Sep and Z-Sep+ both exhibited the best PAH recoveries. In cow s milk, Z-Sep showed a slight advantage in PCB recovery over the other sorbents, especially for the heavier congeners. The columns chosen for GC analysis offered advantages for these applications. The custom SPB-608 provided resolution of PAH isomers, and a faster analysis time. The SLB-5ms provided a high maximum temperature for eluting heavy matrix, and the shorter length and narrow ID in combination with hydrogen carrier provided for a faster analysis time while still achieving the required resolution. Agilent is a registered trademark of Agilent Technologies. FocusLiner is a trademark of SGE Analytical Science Pty. Ltd. SLB and SPB are registered trademarks of Sigma-Aldrich Co. LLC. Supel is a trademark of Sigma-Aldrich Co. LLC. 19

20 References 1. U.S. Environmental Protection Agency International Programs/Persistant Organic Pollutants. http// (accessed Jan. 2013). 2. Anastassiades, M; Lehotay, S.J.; Stajhbaher, D.; Schenck, F.J. Fast and easy mutiresidue method employing acetonitrile extraction/partitioning and dispersive solid-phase extraction for the determination of pesticide residues in produce. J AOAC Int., 2003, 86, Sapozhnikova, Y.; Lehotay, S.J. Multi-class, multi-residue analysis of pesticides, polychlorinated biphenyls, polycyclic aromatic hydrocarbons, polybrominated diphenylethers and novel flame retardants in fish using fast, low-pressure gas chromatography-tandem mass spectrometry. Analytica Chimica Acta, 2013, 758, Forsberg, N.D.; Wilson, G.R; Anderson, K.A. Determination of parent and substituted polycyclic aromatic hydrocarbons in high-fat salmon using a modified QuEChERS extraction, dispersive SPE and GC-MS. J. Agric. Food Chem., 2011, 59 (15), Ramos, L.; Torre, M.; Laborda, F.; Marina, M.L. Determination of polychlorinated biphenyls in soybean infant formulas by gas chromatography. J. Chrom. A, , 823,

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