Simultaneous Determination of Perfluorinated Compounds in Edible

Letter pubs.acs.org/JAFC

Simultaneous Determination of Perfluorinated Compounds in Edible Oil by Gel-Permeation Chromatography Combined with Dispersive Solid-Phase Extraction and Liquid Chromatography−Tandem Mass Spectrometry ABSTRACT: A simple analytical method was developed for the simultaneous analysis of 18 perfluorinated compounds (PFCs) in edible oil. The target compounds were extracted by acetonitrile, purified by gel permeation chromatography (GPC) and dispersive solid-phase extraction (DSPE) using graphitized carbon black (GCB) and octadecyl (C18), and analyzed by liquid chromatography−electrospray ionization tandem mass spectrometry (LC-ES-MS/MS) in negative ion mode. Recovery studies were performed at three fortification levels. The average recoveries of all target PFCs ranged from 60 to 129%, with an acceptable relative standard deviation (RSD) (1−20%, n = 3). The method detection limits (MDLs) ranged from 0.004 to 0.4 μg/kg, which was significantly improved compared with the existing liquid−liquid extraction and cleanup method. The method was successfully applied for the analysis of all target PFCs in edible oil samples collected from markets in Beijing, China, and the results revealed that C6−C10 perfluorocarboxylic acid (PFCAs) and C7 perfluorosulfonic acid PFSAs were the major PFCs detected in oil samples. KEYWORDS: perfluorinated compounds, edible oil, gel permeation chromatography, dispersive solid-phase extraction, HPLC-MS/MS

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INTRODUCTION Perfluorinated compounds (PFCs) are of particular concern because of their ubiquity, persistence, and bioaccumulation in the environment. Many studies have shown that it is difficult for PFCs to be biodegraded because of the high bond energy of carbon−fluorine bonds, and the groups of pollutants have been detected in water,1,2 sediments,3 sludges, and organisms.4−6 Various toxicities and adverse effects of PFCs have also been reported, such as hepatotoxicity,7 developmental toxicity,8 immune toxicity, hormonal effects, carcinogenic potency, and so on.9,10 Low permitted levels of PFCs in drinking water are therefore enforced in most developed countries to reduce the exposure health risks. For example, the maximum permitted concentrations of perfluoro-n-octanoic acid (PFOA) and perfluorooctanesulfonic acid (PFOS) are 0.5 μg/L and 0.3 μg/L, respectively, in drinking water in Minnesota, USA, and that of PFOA is 0.04 μg/L in New Jersey, USA.11 The minimum risk levels (MRLs) of PFOS, PFOA, PFNA, PFHxS, PFHpA, and PFBS in drinking water were 0.04, 0.02, 0.02, 0.03, 0.01, and 0.09 μg/L by US Environmental Protection Agency (EPA) in 2015.12 Besides drinking water,13,14 food is another important pathway of human exposure to PFCs. It has been documented that PFCs accumulate in protein-rich food matrices, although the less hydrophobic chemicals have low log Kow constants. PFCs have been widely detected in food samples, including eggs,5 animal liver,16 fish,17−19 sandwiches,20 and milk in recent years.21 PFCs can be introduced into food during packaging processes. For instance, polytetrafluoroethylene cookware or popcorn bags can release large amounts of PFOA into foods,22 since oil crops are rich in protein of which the percentage in soybean and peanuts was about 40% and 28%, respectively, and the values were even higher than those in milk. Consequently, great attention should be paid to the concentrations of PFCs in edible oils and to their migration and translation during food packaging processes. However, PFCs in edible oils have been © XXXX American Chemical Society

ignored, although they can be present in raw materials or be introduced into food during various food processing methods. The analysis of PFCs in edible oils is challenging because of the trace levels and high fat content of the matrices. As far as we know, few papers focusing on PFCs in edible oils have been published.23−25 Tang et al. developed a liquid−liquid extraction method for the determination of PFOA and PFOS in cooking oil, using basified methanol/water (1:1, v/v, containing 0.5% hydroxide ammonia) and dichloromethane.23 BallesterosGomez et al. analyze PFCs in sunflower oil by loading the oil samples directly to Oasis weak anion exchange (WAX) solidphase extraction (SPE) cartridges without extraction processes,24 and Noorlander et al. applied the method on the determination of PFCs in vegetable oil.25 While PFCs have been detected in the oil samples by the reported methods, the reported dilution pretreatment process would affect the sensitivities and direct loading of a large volume of oil may lead to blocking of SPE cartridges. Gelpermeation chromatography (GPC) and dispersive solid-phase extraction (DSPE) have been widely used as cleanup steps in the analysis of pesticides,26,27 veterinary drugs, and endocrine disruption chemicals to eliminate interference of lipid and pigment.28,29 Unlike SPE, these methods can avoid contamination by PFCs from polytetrafluoroethylene lines and SPE vacuum manifolds. In this work, we developed a comprehensive analytical method using GPC combined with DSPE followed by liquid chromatography−tandem mass spectrometry to simultaneously determine perfluorinated carboxylic acids (PFCAs), perfluorinated sulfonates (PFSAs), and perfluorinated alkylsulfonamides (PFASs) in edible oils. This method was successfully used to monitor PFCs in different types of edible oils from markets in Beijing, China. Received: May 7, 2015 Revised: September 1, 2015 Accepted: September 10, 2015

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DOI: 10.1021/acs.jafc.5b03903 J. Agric. Food Chem. XXXX, XXX, XXX−XXX

Letter

Journal of Agricultural and Food Chemistry

Table 1. Retention Times, Detection Limits, and Optimized MS/MS Parameters for Target PFCs and Internal Isotope PFC Standards compounds PFOS

499.20

PFDoA

613.0

PFDS

599

PFUdA

563.0

PFNA

463.20

PFHxA

313.10

PFHxDA

813.3

PFTeDA

713.20

PFTrDA

663.24

PFHpA

363.10

PFHxS

399.10

PFDA

513

PFOA

413.2

PFHpS

449.1

PFBA

213.2

PFBuS

299.0

PFOSA

498.4

TFMSA

113.2

13

503.4

13

217.4

13

315.3

18

403.5

13

417.5

C4-PFOS C4-PFBA C2-PFHxA O2-PFHxS C4-PFOA

a

precursor ion (m/z)

qualifier ion (m/z) a

80 99.10 569.80a 269.40 80a 99.2 519.60a 269.40 419.50a 219.40 269.40a 119.40 769.8a 169.6 669.60a 319.60 319.8a 369.8 319.50a 169.30 80.0a 99.10 469.6a 269.5 369.8a 169.2 80a 99 169.2a 97 80.0a 99.2 78.2a 169.4 69.0a 82.2 79.7a 99.3 172.3a 59.1 271.0a 120.3 84.3a 102.8 373.1a 169.6

DP (V)

CE (V)

CXP (V)

tR (min)

IDLs (μg kg−1)

MDLs (μg kg−1)

−178 −178 −58 −58 −220 −220 −59 −59 −50 −50 −38 −38 −79 −79 −79 −79 −62 −62 −38 −38 −85 −85 −51 −51 −41 −41 −121 −121 −46 −46 −167 −167 −303 −303 −37 −37 −88 −88 −85 −85 −99 −99 −105 −105 −68 −68

−94 −60 −17 −29 −105 −79 −17 −29 −14 −26 −12 −31 −19 −47 −17 −33 −30 −28 −14 −27 −76 −53 −16 −27 −12 −25 −82 −56 −11 −24 −71 −51 −72 −40 −15 −29 −15 −24 −14 −25 −48 −26 −15 −29 −19 −28

−8 −11 −15 −15 −108 −108 −50 −50 −25 −25 −28 −13 −40 −20 −44 −20 −18 −24 −28 −15 −29 −10 −36 −25 −25 −21 −30 −17 −21 −11 −13 −14 −13 −15 −7 −5 −40 −11 −39 −20 −15 −21 −22 −11 −24 −17

6.05

0.02

0.2

8.51

0.04

0.04

7.89

0.004

0.1

7.91

0.004

0.02

6.77

0.02

0.02

3.96

0.04

0.04

10.46

0.004

0.2

9.43

0.004

0.08

9.13

0.4

0.4

5.24

0.04

0.04

5.30

0.004

0.004

7.29

0.004

0.004

6.16

0.04

0.04

6.15

0.02

0.02

2.31

0.04

0.04

2.97

0.04

0.04

8.18

0.04

0.04

2.15

0.04

0.04

6.78 2.17 3.90 5.20 6.13

Quantifier ion.

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perfluoruodecanesulfonic acid (PFDS), perfluoro-n-undecanoic acid (PFUdA), perfluoro-n-nonanoic acid (PFNA), perfluoro-n-hexanoic acid (PFHxA), perfluoro-n-hexadecanoic acid (PFHxDA), perfluoro-ntetradecanoic acid (PFTeDA), perfluoro-n-tridecanoic acid (PFTrDA), perfluoro-n-heptanoic acid (PFHpA), perfluorohexanesulfonic acid (PFHxS), perfluoro-n-decanoic acid (PFDA), perfluoro-n-heptanesulfonate (PFHpS), perfluoro-n-butanoic acid (PFBA), perfluorooctanesulfonamide (PFOSA), sodium perfluoro-1-butanesulfonate (PFBuS), and trifluoromethanesulfonic acid (TFMSA), and isotopically labeled standards, namely, sodium perfluoro-1-[1,2,3,4-13C4]-octanesulfonate (13C4-PFOS), perfluoron-[1,2,3,4-13C4]-butanoic acid (13C4-PFBA), perfluoro-n-[1,2-13C2]hexanoic acid (13C2-PFHxA), sodium perfluoro-1-hexane-[18O2]-sulfonate

MATERIALS AND METHODS

Chemicals and Instruments. Oil samples were purchased from local markets in Beijing in October−November 2013 and stored at normal atmospheric temperature. LC-MS grade acetonitrile and methanol were obtained from the Merck (Darmstadt, Germany), and HPLC grade formic acid (99.7%) and ammonium acetate (99.5%) were obtained from Dikma Technology Inc. (Richmond, VA, USA). Primary secondary amine (PSA), octadecyl (C18), and graphitized carbon black (GCB) sorbents were obtained from Agela Technologies (Tianjin, China). Ultrapure water was produced using a Milli-Q RC apparatus (Millipore, Bedford, MA, USA). The purities of most standard PFCs were ≥98%, with a minority of purity ≥92%. PFOS, PFOA, perfluoro-n-dodecanoic (PFDoA), B


Letter


Waters, Ireland) at 40 °C, with an injection volume of 5 μL. Mobile phases A (aqueous buffer with 5 mM ammonium acetate and 0.1% formic acid) and B (methanol with 5 mM ammonium acetate and 0.1% formic acid) were used, with a gradient elution of A:B = 40:60 (0−0.5 min), 20:80 (0.5−4 min), 5:95 (4−8 min, held 2 min), and 40:60 (10−13 min, held 7 min) at flow rates of 0.20 (0−0.5 min), 0.30 (0.5−8 min), 0.25 (8−10 min), and 0.20 (10−20 min) mL/min (see Table S1). Tandem Mass Spectrometer Conditions. Mass spectrometric detection was performed using an API 5000 tandem quadrupole mass spectrometer (Applied Biosystems, Foster City, CA, USA) in negative electrospray ionization mode with multiple-reaction monitoring (MRM). Typical parameters of the electrospray ionization source were as follows: ion spray voltage, − 4500 V; curtain gas pressure (CUR), 35 psi; collision gas (CAD), 4 V; atomization air pressure (GS1), 60 psi; auxiliary gas pressure (GS2), 70 psi; dwell time, 200 ms; resolution Q1, low; resolution Q2, unit. The MRM transitions and collision energy (CE), declustering potential (DP), entrance potential (EP), and collision cell exit potential (CXP) used are summarized in Table 1. All system control, data acquisition, and data analysis were performed using AB Sciex Analyst 1.4.2 software (Applied Bioscience). Sample Preparation. A homogenized edible oil sample (5 g) was weighed and placed into a 50 mL polypropylene (PP) centrifuge tube. Internal standards (ISs) containing 13C4-PFOA, 13C4-PFOS, 13 C4-PFBA, 13C2-PFHxA, and 18O2-PFHxS (100 μL, 20 μg/L) were spiked to the sample. After equilibrium for 20 min, acetonitrile (10 mL) was added and the tube was shaken vigorously for 3 min and centrifuged for 6 min (6000 rpm and 4 °C). The supernatant was transferred to a 50 mL bottle, and these procedures were performed twice. The combined supernatants were rotoevaporated (15 kPa, 110 rpm, and 30 °C), and the residues were reconstituted with cyclohexane:ethyl acetate (1:1 v/v, 10 mL) solvent for purification by an Accuprep MPS-GPC System (J2 Scientific, Columbia, MO, USA). This system comprised an autosampler, a solvent delivery module, an ultraviolet (UV) detector, a fraction collector, and a GPC column (400 mm × 30 mm) containing 50 g of polymer resin styrene− divinylbenzene Biobead SX-3 (Bio-Rad, Irvine, CA, USA). Ethyl acetate−cyclohexane (1:1, v/v) was used as the mobile phase at a flow rate of 4.7 mL/min. The fraction containing target compounds was collected over 20−60 min in a 250 mL tube. After GPC, the eluate was evaporated to dryness using a rotary evaporator (Heidolph, Schwabach, Germany) at 150 rpm and 30 °C. The residue was reconstituted in methanol (1 mL) and then transferred to a centrifuge tube containing

(18O2-PFHxS), and perfluoro-n-[1,2,3,4-13C4]-octanoic acid (13C4PFOA), were purchased from Wellington Laboratory (Ontario, Canada). A cocktail solvent containing all 18 PFCs with respective concentrations of 10 μg/mL was prepared by diluting the standards with methanol. Working standard solvents for calibration were freshly prepared with methanol. Isotopic standard working solutions containing 13C4-PFOA, 13 C4-PFOS, 13C4-PFBA, 13C2-PFHxA, and 18O2-PFHxS with respective concentrations of 200 μg/mL were prepared by diluting the ISs with methanol. All solutions were stored at −20 °C. HPLC Conditions. Chromatographic analyses were conducted using an Agilent series 1200 HPLC system (Agilent, Santa Clara, CA, USA) equipped with a binary pump, column oven, and autosampler. PFCs were separated using an XBridge C18 column (150 mm × 2.1 mm × 3.5 μm;

Table 2. Recoveries of Target PFCs (1 μg/kg) Using Different Extraction Solvents (n = 3) acetonitrile

acetonitrile + 0.1% formic acid

methanol

compounds

average recovery (%)

RSD (%)


RSD (%)


RSD (%)

PFOS PFDoA PFDS PFUdA PFNA PFHxA PFHxDA PFTeDA PFTrDA PFHpA PFHxS PFDA PFOA PFHpS PFBA PFBuS PFOSA TFMSA

100 74 103 753 98 121 130 85 87 112 107 78 84 129 112 103 103 103

13 17 17 17 14 15 14 3 3 1 6 14 6 9 10 15 12 13

44 40 29 53 93 85 23 46 43 70 113 39 56 166 85 53 37 37

4 16 8 20 23 48 3 20 12 32 19 15 13 26 13 3 8 6

117 207 145 186 217 347 51 104 104 320 144 217 303 183 214 122 139 116

30 42 7 2 1 23 1 23 5 4 2 18 11 6 14 24 10 21

Figure 1. Recoveries of target PFCs at different time periods using GPC with cyclohexane:ethyl acetate (v/v, 1:1) as the mobile phase, at a flow rate of 4.7 mL/min. C


Letter


Figure 2. Recoveries of target PFCs spiked at 5 μg/kg in blank edible oil samples using (a) various DSPE sorbents, (b) different amounts of GCB, and (c) different amounts of C18. C18 (150 mg) and GCB (10 mg) as DSPE sorbents. The mixture was shaken for 2 min, centrifuged for 6 min (3000 rpm and 4 °C), and filtered through a 0.22 μm membrane prior to LC-MS/MS analysis. Quality Assurance and Quality Control. The identification was based on retention time, the transitions, and their ion ratio by using SRMs of PFCs.30,31 Concentrations of all target PFCs were quantified by the internal standard isotope method. Concentrations of PFOS, PFDS, and PFOSA in edible oil samples were quantified relative to 13 C4-PFOS; PFDoA, PFUdA, PFNA, PFHxDA, PFTeDA, PFTrDA, PFHpA, PFDA, and PFOA relative to 13C4-PFOA; PFHxA relative to 13 C2-PFHxA; PFHxS, PFHpS, PFBuS, and TFMSA relative to 18O2PFHxS; and PFBA relative to 13C4-PFBA. All equipment rinses were carried out with LC-MS grade methanol and pure water before use to

avoid sample contamination. Procedural blanks were measured throughout the study, and low levels of PFOS, PFDS, PFHxDA, and PFTeDA (3). The MDLs of all target PFCs were in the range from 0.004 to 0.4 μg/kg. It should be noted that the MDLs were almost 10 times lower than that obtained for milk by Young et al.,39 and the results indicate that the method had relatively high sensitivities to the determination of trace concentrations of PFCs in edible oils. Application to Edible Oils. Six types of edible plant oils with different manufacturing processes and brands purchased

detection rate (%)




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from supermarkets in Beijing were analyzed with the developed method in 2013. As shown in Table 4, the detected PFC concentrations in the oils ranged from below the MDL to 4.64 μg/kg with acceptable RSDs less than 25% (n = 3), and these values are lower than those detected in fish6,46−48 and eggs15 and similar to those in milk.21,49 The PFOA detection rate was the highest (92%) among the 18 PFCs with concentrations from below the MDL to 0.50 μg/kg, and the possible reason could be its widespread use as a processing agent in industrial products; 1.8 μg/kg of PFOA was also detected by Schecter et al. in olive oil.50 Second to PFOA, the detection rates of PFHxA, PFNA, and PFDA were 67%, 58%, and 50%, respectively. It should be noted that the highest concentration detected was 4.64 μg/kg of PFNA in blend oil, and this is probably due to PFNA not being globally regulated. A similar result was reported by Van et al. in polar-bear liver.51 PFHpA and PFHpS were detected at rates of 25%, with concentrations below the MDL to 0.50 μg/kg in all six types of edible oils. In general, C6−C10 PFCAs and PFSAs were found extensively in the edible oils, which is similar to the findings reported by Chung et al. for fatty food.52

Key Laboratory of Agro-product Quality and Safety, Institute of Quality Standards & Testing Technology for Agro-products, Chinese Academy of Agricultural Sciences, Beijing 100081, China

ASSOCIATED CONTENT

S Supporting Information *

The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jafc.5b03903. Procedure of gradient elution, procedure blank, recovery, purification efficiency by different DSPE sorbents, graphs of PFCs with remarkable blank value, and PFCs under different gradients (PDF)

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REFERENCES

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Lili Yang Fen Jin* Peng Zhang Yanxin Zhang Jian Wang Hua Shao Maojun Jin Shanshan Wang Lufei Zheng Jing Wang

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Letter

AUTHOR INFORMATION

Corresponding Author

*Institute of Quality Standards & Testing Technology for Agroproducts, Chinese Academy of Agricultural Sciences, Beijing 100081, China. Tel: 010-82106570. E-mail: [email protected]. Funding

Financial support from the National Key Technology R&D Program of China (2012BAD29B03) is gratefully acknowledged. Notes

The authors declare no competing financial interest.

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ACKNOWLEDGMENTS We are grateful to the four anonymous reviewers whose comments and suggestion were very helpful to improve this paper. We also thank Yi Wan from Peking University, China. G


Letter

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Simultaneous Determination of Perfluorinated Compounds in Edible

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