University of the Aegean

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1 University of the Aegean Department of Environmental Studies Water and Air Quality Laboratory Simultaneous determination of pharmaceutical compounds and endocrine disrupting chemicals (EDCs) in wastewater by solid phase extraction and gas chromatography-mass spectrometry V. G. Samarasª, N.S. Thomaidis b, A.S. Stasinakisª, G. Gatidou a,b, T.D. Lekkasª ªWater and Air Quality Laboratory, Department of Environmental Studies, University of the Aegean b Laboratory of Analytical Chemistry, Department of Chemistry, University of Athens

2 Contents Introduction Method development Results and Discussion Conclusions Future Research

3 Pharmaceutical compounds and endocrine disrupting chemicals in WWTPs

4 Target Compounds Nonylphenol (NP technical mixture) Nonylphenol monoethoxylate (NP1EO) Nonylphenol diethoxylate (NP2EO) Transformation products of NPnEOs which are used as non-ionic surfactants Bisphenol A (BPA) : polycarbonates and epoxy resins Triclosan (TCS) : antimicrobial agent Ibuprofen (IBN) Naproxen (NPX) Diclofenac (DFN) Non-steroidal antiinflammatory drugs (NSAIDs) Ketoprofen (KFN)

5 Aims and Originality of the present study Aims: Development, Optimization, Validation of a Simple, Fast and Precise analytical method for the simultaneous determination of IBN, DCF, NPX, KFN, NP, NP1EO, NP2EO, BPA and TCS, in wastewater using BPA-d16 and meclofenamic acid (MCF) as surrogates Originality: Many analytical methods are available for the determination of the target compounds but none for the simultaneous qualitative and quantitative determination of the proposed mixture in levels of ng/l

6 Method development Step 1. GC-MS optimization Step 2. Derivatization optimization Step 3. Solid phase extraction optimization Step 4. Validation

7 Step 1. GC-MS optimization Hewlett Packard Gas Chromatograph 5890 Series II Hewlett Packard Mass Spectrometer HP5971 MSD Step 1 Column: DB5MS capillary column (60 m) with a film thickness of 0.25 μm and internal diameter of 0.32 mm Carrier gas: helium (0.9 ml min 1 ) Column temperature: at 80 C for 1 min, from 80 to 248 C at 15 C min -1, 1 min to 248 C and from 248 to 280 C at 3 C min -1 Injection volume: 1 μl (splitless mode) Inlet temperature: 280 C. MS transfer line temperature: 280 C Ion source temperature: 180 C

8 Step 1. GC-MS optimization Qualitative analysis: full scan mode (mass range from 50 to 400) Step 1 Quantitative analysis: selected ion monitoring (SIM) mode IBF: 160 and 161 DFC: 214, 242, 216 and 367 KFN: 282, 283, 311 and 105 NPX: 185, 243, 301 and 141 MCF: 242, 244 and 367 NP: 179 and 292 NP1EO: 237, 251, 265 and 293 NP2EO: 309 and 295 TCS: 200, 247 and 362 BPA: 357 and 358 BPA-d16: 368 and 369

9 Step 1. GC-MS optimization Step 1 Chromatogram of a standard solution containing 0.8 mg L 1 of the target compounds and 0.6 mg L 1 of the surrogates (BPA-d16, MCF) in SIM mode

10 Step 2. Derivatization optimization Experimental procedure includes: Step 2 Different volumes of BSTFA (50, 60, 70, 80 and 100 μl) Different volumes of pyridine (10, 25, 50 and 75 μl) in the co-presence of 50 μl BSTFA Comparison between BSTFA and BSTFA + 1%TMCS The effect of pyridine and 1% TMCS addition in the derivatized solution

11 IBF KFN DFC NPX MFC NP NP1EO NP2EO TCS BPA BPA d16 Area (mean values) Company Step 2. Effect of 1% TMCS in the derivatized solution μL BSTFA μL BSTFA Step μL BSTFA + 1%TMCS μL BSTFA + 1%TMCS+10μL pyridene Substances The degree of derivatization was affected by the volume of BSTFA, with higher sensitivity at 100 μl The presence of 1% TMCS resulted in high sensitivity High sensitivity and low RSDs with the use of 50μL BSTFA + 1%TMCS + 10μL pyridine

12 NP NP1EO NP2EO TCS BPA A BPA d16 KFN DFC NPX IBN MFC Area (mean values) Company Step 2. Effect of pyridene in the derivatized solution Step μl BSTFA 50μL BSTFA + 10μL pyridene 50μL BSTFA + 25μL pyidene 50μL BSTFA + 50μL pyridene Substances Low volume of pyridine (10-25μL) has been found to improve sensitivity and RSDs (<9), while higher volume (50-75μL) resulted in poor chromatographic peaks for most of the compounds

13 Step 3. Solid phase extraction Key parameters: Step 3 Extraction cartridges: Elution Organic solvents: C18 Mixture of DCM : hexane (4:1) Oasis HLB Ethyl acetate Effect of solution ph:

14 Step 3. Elution organic solvent Step 3 Elution with DCM-hexane: resulted in zero recoveries for the pharmaceutical compounds, 71.9% ± 9.1 for TCS 93.2% ± 3.0 for BPA 69.5% ± 5.1 for NP1EO 57.1% ± 5.4 for NP2EO 65% ± 6.4 for NP (T.M.) Elution with ethyl acetate: resulted in satisfactory recoveries (>92%) for both pharmaceutical compounds and endocrine disrupting chemicals

15 Step 3. ph effect and type of sorbent Absolute recoveries at ph 2,5 Absolute recoveries at ph 5,3 Absolute recoveries at ph 7 Compounds C18 OASIS C18 OASIS C18 OASIS Step 3 IBF 77 ± 1 76 ± 2 71 ± 2 74 ± 5 72 ± 5 72 ± 3 DFC 83 ± 9 73 ± 5 71 ± 3 13 ± ± 0 6 ± 3 NPX 85 ± 1 84 ± 2 81 ± 8 80 ± 6 91 ± 4 94 ± 10 KFN 79 ± 6 83 ± 3 81 ± 7 84 ± 3 87 ± 8 82 ± 4 MFC 77 ± 4 80 ± 2 73 ± 3 5 ± 2 72 ± 16 7 NP (T.M.) 76 ± 3 72 ± 5 70 ± 5 69 ± 2 73 ± 9 75 ± 4 NP1EO 70 ± 4 68 ± 6 76 ± 4 78 ± 4 75 ± 8 74 ± 4 NP2EO 85 ± 6 84 ± 5 81 ± ± 1 82 ± 5 74 ± 1 TCS 67 ± 1 65 ± ± 1 62 ± 1 17 ± ± 11 BPA 74 ± 3 77 ± ± 1 24 ± 7 18 ± 4 76 ± 5 BPA d16 66 ± 6 64 ± 6 34 ± 5 18 ± 8 10 ± 4 69 ± 11 DFC and MFC, BPA and BPAd16 were the only compounds for which low recoveries were obtained at ph 5.3 and 7 for Oasis HLB Low recoveries were also obtained for BPA, TCS and BPA-d16 at ph 5.3 and 7 for C18

16 Step 3. ph effect and type of sorbent Absolute recoveries at ph 2,5 Absolute recoveries at ph 5,3 Absolute recoveries at ph 7 Compounds C18 OASIS C18 OASIS C18 OASIS Step 3 IBF 77 ± 1 76 ± 2 71 ± 2 74 ± 5 72 ± 5 72 ± 3 DFC 83 ± 9 73 ± 5 71 ± 3 13 ± ± 0 6 ± 3 NPX 85 ± 1 84 ± 2 81 ± 8 80 ± 6 91 ± 4 94 ± 10 KFN 79 ± 6 83 ± 3 81 ± 7 84 ± 3 87 ± 8 82 ± 4 MFC 77 ± 4 80 ± 2 73 ± 3 5 ± 2 72 ± 16 7 NP (T.M.) 76 ± 3 72 ± 5 70 ± 5 69 ± 2 73 ± 9 75 ± 4 NP1EO 70 ± 4 68 ± 6 76 ± 4 78 ± 4 75 ± 8 74 ± 4 NP2EO 85 ± 6 84 ± 5 81 ± ± 1 82 ± 5 74 ± 1 TCS 67 ± 1 65 ± ± 1 62 ± 1 17 ± ± 11 BPA 74 ± 3 77 ± ± 1 24 ± 7 18 ± 4 76 ± 5 BPA d16 66 ± 6 64 ± 6 34 ± 5 18 ± 8 10 ± 4 69 ± 11 C18 cartridges resulted in sufficient RSDs (<6%) at ph 2.5 and taking into account their better recoveries in the wide range of ph ( ), they were chosen for the isolation of the target compounds from wastewater samples

17 Step 3. Final developed method Wastewater sample (100 ml) Step 3 Filtration (ph 2.5) SPE: C18 3x2 ml Ethyl acetate 3x2mL MeOH 3x2 ml H 2 O Elution: 3x2 ml Ethyl acetate Evaporation to dryness 50 μl BSTFA (1%TMCS) + 10 μl pyridine GC-MS analysis

18 Step 4. Validation of the developed method Calibration equations, coefficients of correlation (R 2 ), limits of detection and quantification of the target compounds in wastewater Step 4 Compound Calibration equation R 2 Instrumental LOD (μg l -1 ) Method LOD (ng l -1 ) IBF y = x NPX y = x DCF y = x KFN y = x TCS y = x BPA y = x NP (T.M.) y = x NP1EO y = x NP2EO y = x

19 Step 4. Validation of the developed method Step 4 Accuracy and precision data of the extraction procedure (800 ng L -1 ) Compound Recoveries (%) intra-day precision R.S.D. (%), (n = 6) R.S.D.s : < 12 % Wastewater inter-day precision R.S.D. (%), (n = 3, k = 3) IBF NPX DCF KFN TCS BPA NP (T.M.) NP1EO NP2EO Recovery range : 92 % %

20 Conclusions Development of an efficient and accurate integrated method for the simultaneous determination of NP, NP1EO, NP2EO, TCS, BPA, IBF, NPX, KFN and DFC in wastewater Sufficient isolation of all the compounds from the matrix was obtained using C18 cartridges at ph solution 2.5 and ethyl acetate as the elution solvent Satisfactory precision and good recoveries for all the tested compounds and adequate LODs for environmental monitoring

21 Future research Future work will Develop an analytical method for the determination of the target compounds in particulate phase of wastewater and sewage sludge Determine their concentration levels in wastewater treatment plants and derive safe conclusions for their fate and possible threat during final disposal

22

23

24 Thank you for your attention Samaras Vasilios PhD Student University of Aegean Mytilene, University Hill GR

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