Perfluorinated compounds by LC MS
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1 Analysis, fate and risks of organic contaminants in river basins under water scarcity Valencia 7-8 ebruary 2010 Perfluorinated compounds by LC MS Marinella arré, Marta Llorca, rancisca Pérez Yolanda Picó, Damià Barceló Introduction: Human exposure and previous works Recommendations and remarks LC Separations MS Instruments Conclusions
2 Perfluorinated compounds (PCs) Perfluorinated = fully fluorinated H Ex. Perfluorooctanoic acid (PA, C 8) Very stable(c bond energy 485 kj/mol) (C C 346, C N 305, C 358, C Cl 327 kj/mol) Most common structures H n=3-9 Perfluorocarboxylic acids Sulfonamides S H N R R = methyl, ethyl S - n=2, 4, 6 Perfluorosulfonic acids n = 4, 6, 8 Phosphate acids P - H H n=4, 6, 8 luorotelomer alcohols P R n=4, 6, 8 Telomer acids H n = 2, 4, 6 Phosphinic / Phosphonic R
3 Properties Thermally stable (in excess of 150 C) Resists degradation(acid, alkali, oxidizing agents, bio ) Hydrophobic and oleophobic (3 phases in Kow) Good surfactants, lubricants Non-flammable Chemically inert Samples. Samples should be stored and manipulated in plastic or fluorine free materials as polypropylene, polyethylene etc.
4 Material used. The extraction procedure should be carried out in plastic (PP) tubes and eliminate contact with fluoropolymers and glass. The possible contamination of PCs, especially PA, leaching from the LC-MS system, should be controlled using instrumental blank. The instrument blank consists in an extract of the composition of the sample which should be injected every 5 samples in order to monitor contamination. Another possibility is using a chromatographic column (C18 or C8) before the injection system in order to delay the source of PCs from the pumps or the degasser. Procedural contamination can be originated from contacts with laboratory materials made of, or containing, fluoropolymers, such as polytetrafluoroethylene (PTE), polyvinylidenefluoride (PVD) or perfluoroalkoxy compounds lids, septa and filters. Due to this procedural blanks should be analyzed with each set of 20 samples were used for checking possible laboratory contamination. The preparation of procedural blanks is similar (solvent, material, plastic ware) to extraction of sample. Quality Assurance and Quality Control 1.5e5 1.4e5 1.3e PA (sample) Procedural blanks were carried out in order to assure the not contamination by PCs for the entire method. Blank tests were also carried out on all the sample containers to rule out possible contamination from the sampling, storage and shipment containers. Instrumental Contamination 1.2e5 1.1e5 1.0e5 9.0e4 8.0e4 7.0e4 6.0e4 5.0e4 4.0e4 3.0e4 2.0e4 1.0e Time, min 9.06 PA (system)
5 LC separation of fluorinated compounds has been mainly carried out with C-18 and C-8 columns RP-C18 and perfluorinated RP-C8: RP-C18: Matrix effects in complex samples RP-C18 and perfluorinated RP-C8: separation of branched isomers, in this case to minimize separation increase LC column Tº to ºC. Regarding mobile phases, mixtures of acetonitrile water and methanol water, often modified with ammonium acetate (between 1.0 and 20 mm) to improve LC separation and MS sensitivity, have usually been used. Quadrupole based instruments ull mass range acquisition
6 QqQ Model Micromass Quattro Micro API, Waters equipped with a dual Z spray ESI/APCI, a Waters Alliance 2795LC lwith a 2695 Waters Alliance auto sampler QqLIT 4000 Q TRAP MS/MS system from Applied Biosystems /MDS Sciex coupled to a Symbiosis Pico system 3 D IT Esquire D ion trap from Bruker Daltonics with and Agilent HP1100 LC QqT Agilent 6430 QT system from Agilent coupled to an Agilent HP1100 LC. PCs SRM1 a Product ion Identification CE (V) SMR2 b Product Ion identification LC QqQ MS/MS CE (V) Additional SRM PPA [M H C 2 ] 10 PBS [S [S 3 25 PA [C [M H C 2 10 PS [S [S 3 45 PNA [M H C [C 4 9 ] 10 i,p PNA [M H C [C 4 9 ] 10 PDA [M H C [C L PDS [S [S 3 45 LC QqLIT MS/MS PPA [M H C 2 15 PBS [S [S 3 80 PA [C [M H C PS [S [S PNA [C [C 4 9 ] i,p PNA [C 4 9 ] [C PDA [C 2 5 ] [M H C L PDS [S [S a Quantifier precursor product ion transition b Qualifier precursor product ion transition
7 Quality Assurance and Quality Control or identification purposes, retention times of PCs in the standards and in the samples were compared at a tolerance of ±2.5%. Moreover, in accordance with the 2002/657/EC Decision, the relative ion intensities (each product ion area signal versus the base product ion area signal) of the spiked samples were compared with the relative ion intensities of PCs standard solutions, at the same concentration levels as used for the construction of the calibration curve. Instrumental parameters of the LC QqLIT MS method developed for the analysis of PCs (values obtained by injection of standard solutions) Compounds Linear range (ng/l) Linearity (r 2 ) ILD (fg) ILQ (fg) Precision (RSD %) Intraday Interday PA PS i,p PNA PNA PDA PDS Linear range in standard solutions. ILD and ILQ: instrumental limit of detection and quantification respectively
8 LC QqLIT MS/MS LC QqQ MS/MS PCs LD (µg/kg) LQ (µg/kg) LD (µg/kg) LQ (µg/kg) PPA PBS PA PS PNA i,p PNA PDA L PDS Extracted ion chromatogram of PCs Total Ion Chromatogram of PCs 3.0e5 2.6e5 2.2e5 1.8e5 1.4e5 1.0e5 PPA 9.38 Max. 3.2e5 cps. Concentration 12.5 µg/kg 6.0e4 XIC of MRM (24 pairs): 413,0/369,0 amu from Sample 2 (H b) of huevas.wiff (Turbo Spray) Max. 1,3e4 cps. 2.0e4 8.0e4 7.5e4 7.0e4 6.5e4 6.0e4 5.5e4 5.0e4 4.5e4 4.0e4 3.5e4 3.0e4 2.5e4 2.0e4 1.5e4 1.0e PPA + PBS PA + MPA PS + MPS MPDA Time, min 7.8e e4 PBS 6.0e4 5.0e4 4.0e4 3.0e4 2.0e4 1.0e4 1.9e4 1.7e4 PA 1.5e4 1.3e4 1.1e ,81 Max. 7.8e4 cps. Concentration 18.9 µg/kg Max. 1.9e4 cps. Concentration 0.44 µg/kg 5.7e4 5.0e4 4.0e4 3.0e4 2.0e4 1.0e4 0.0 Max. 5,7e4 cps PS Concentration 0.13 µg/kg Time, min 34
9 Time > % 0 PPA Concentration 12.5 µg/kg % > % 0 PBS Concentration 18.9 µg/kg >269 % PA > 79 % PPS Concentration in µg/kg PC Hake Roe Sword fisn Stripped Mullet Young Hake Anchovy Muscle Liver Muscle Liver Muscle Liver LC QqLIT MS/MS PPA PBS < LQ 2.04 < LQ PA PS <LQ <LQ PDA <LQ <LQ <LQ <LQ <LQ LC QqQ MS/MS PPA PBS PA < LQ 1.25 PS < LQ 0.86 PDA
10 Comparison of high sensitive QqQ in blood : PDA
11 PCs MS LD (µg/kg) MS 2 LD (µg/kg) MS 3 LD (µg/kg) PPA PBS PA , 269, PS PNA , i,p PNA , PDA , 269, PDS The QqLIT instrument was used to perform the LC MS/MS analyses in the SRM mode. SRM mode can be combined with the Enhanced Product Ion Scan (EPI) and MS 3 modes, for the unambiguous confirmation of compounds. perating with the EPI mode Q1 filters the desired parent ion and is fragmented in the Q2 region. ragment ions are trapped in the Q3 region for a specified time prior to being scanned out. The main limitation is the low stability of fragment ions because the isolation and fragmentation steps are both occurring in the LIT, only fragment ions produced with m/z values of 30% of the parent mass and higher are stable in the ion trap The EPI and MS 3 modes were used for confirmatory purposes.
12 -EPI (413,00) CE (-25): Exp 1, 11,060 min from Sample 1A (PA_EPI)_EPI.wiff (Turbo Spray) 8,0e4 7,5e4 7,0e4 6,5e4 6,0e4 5,5e4 5,0e4 4,5e4 4,0e4 3,5e4 3,0e4 2,5e4 2,0e4 1,5e4 1,0e , Da Da 219, Da 369, Da Da Da
13 -MS3 (413,00),(369,00): Exp 2, 11,024 min from Sample 1A (PA_EPI)_EPI.wiff (Turbo Spray) C , , ,0 C -EPI (499,00) CE (-25): Exp 1, 11,063 min from Sample 1A (PS_EPI)_EPI.wiff (Turbo Spray) 6,9e4 6,5e4 6,0e4 5,5e4 5,0e4 4,5e4 4,0e4 3,5e4 3,0e4 2,5e4 2,0e4 1,5e4 1,0e4 5000,0 80,0 99,0 C Da - S - S Da 280, D - S Da m/z, amu -MS3 (499,00),(280,00): Exp 3, 11,063 min from Sample 1A (PS_EPI)_EPI.wiff (Turbo Spray) 130, S 5200 C m/z, amu C - 280,0 S
14 Comp. I.S. MS 2 EPI MS 3 Transitions CE (V) m/z (% ratio) Assignment AP A2 CE m/z (% ratio) Assignment PA MPA 413> (100) [C > (88) [C (100) [C (24) 369 (20) 413> (50) [C (100) 219 (13) PS MPS 499> (100) [S [C 3 7 [C 7 15 [C 3 7 [C > (50) [S 3 499> (35) [C 4 8 S (100) 280 (10) ip PNA MPA 463> (100) [C (100) 419 (10) 463> (82) [C (100) [C 2 S 3 [C 4 8 S 3 [C 4 9 [C 8 17 [C (55) [C (36) [C (15) [C 4 9 Comp. I.S. MS 2 EPI MS 3 Transitions CE (V) m/z (% ratio) Assignment AP A2 CE m/z (% ration) Assignment PNA MPA 463> (100) [C (100) 219 (20) [C 3 7 [C > (75) [C 3 7 PDA MPDA 513> (100) [C > (88) [C (100) [C > (85) 169 (85) 269 (60) 469 (5) [C 5 11 [C 9 19
15 QqLIT working in selected reaction monitoring (SRM) provides the best LQs in general. The other mass analyzers, QqQ, 3 D IT and QqT can determine some of these compounds in the analyzed samples. QqLIT, 3 D IT and QqT present additional features MS 3 fragmentation (QqLiT and 3 D IT) Enhanced Product Ion (EPI) (QqLIT) Search other non target PCs (QqT) The recently developed QqT MS instruments are valuable analytical tools for rapid screening of PCs. Consolider-Ingenio 2010 CSD EU -Project CNffIDENCE ( CP Collaborative Project) ood Safety Platform Programme of the Conselleria de Sanitat of the Generalitat Valenciana (Projects No. PLAT2008-A-004 and PLAT2009-A-013) or providing us some of the QqT data
16 Any questions? Q & A Questions?
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