Simultaneous determination of 19 phthalate esters in cosmetics using gas chromatography-mass spectrometry

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2012 3 Vol. 30 No. 3 March 2012 Chinese Journal of Chromatography 273 ~ 279 DOI 10. 3724 /SP. J. 1123. 2011. 11022-19 1 3 1 2 3 1* 1. 361005 2. 350031 3. 362000 19 - GC-MS - 2 3 m /m - 8 2 v /v GC- MS 19 0. 1 0. 5 2. 0 μg /g 72. 2 ~ 110. 9 0. 1 μg /g RSD n = 6 10. 3 3 0. 006 5 μg /g ~ 0. 062 μg /g 6 19 PAEs PAEs - O658 A 1000-8713 2012 03-0273-07 Simultaneous determination of 19 phthalate esters in cosmetics using gas chromatography-mass spectrometry LIANG Jing 1 3 ZHUANG Wan e 1 WEI Danqi 2 OU Yan 3 GONG Zhenbin 1* 1. State Key Laboratory of Marine Environmental Science Xiamen University Xiamen 361005 China 2. Fujian Food and Drug Administration Fuzhou 350031 China 3. Fareast Testing & Technology Services Co. Ltd. Fujian Quanzhou 362000 China Abstract A method was developed for the simultaneous determination of 19 phthalate esters PAEs at trace level in cosmetics by solid phase extraction SPE purification and gas chromatography-mass spectrometry GC-MS detection. The PAEs were extracted from cosmetic samples by dichloromethane with ultrasonic-assisted technique purified by an SPE column packed with silica gel and neutral alumina 2 3 m /m with the elution of 20 ml of mixed solvent of ethyl acetate-hexane 8 2 v /v. Qualitative and quantitative analysis were carried out by GC-MS in full scan and selected ion monitoring modes. The retention time of quantitative ions and the abundance ratio of characteristic ions were applied to rapidly and accurately identify each analyte so as to prevent the occurring of possible mistakes from complex matrix intervention. Under optimized conditions the average recoveries for a shampoo sample spiked with the standards at 0. 1 0. 5 2. 0 μg /g were in the range of 72. 2 and 110. 9 and the relative standard deviations RSDs for the 19 PAEs were less than 10. 3 n = 6 at the spiked level of 0. 1 μg /g. The limits of detection LODs as 3 times of standard deviation were between 0. 006 5 μg /g for diisopentyl phthalate and 0. 062 μg /g for diisobutyl phthalate. The method was successfully applied to the determination of the PAEs in 6 types of cosmetics. It is expected to promote the determination of the PAEs in other cosmetics with different matrices. Key words gas chromatography-mass spectrometry GC-MS phthalate esters PAEs cosmetic phthalate esters PAEs 1 PAEs 2 PAEs *. Tel 0592 2186222 E-mail zbgong@ xmu. edu. cn.. 2011-11-14

274 30 2- bis 2-ethoxyethyl phthalate 3 4 BEEP di-n-hexyl phthalate DnHP butyl benzyl PAEs phthalate BBP 2- di WHO 1995 2-ethylhexyl phthalate DEHP PAEs di-n-heptyl phthalate DHP 76 /768 /EEC 2007 dicyclohexyl phthalate DCHP PAEs di-n-octyl phthalate DnOP 18 PAEs diundecyl phthalate DUP 5-7 - 8-97. 0 Sigma-Aldrich IS 1 GC-MS 9-13 - 4 di-n-butyl phthalate-3 4 5 14 PAEs 15 6-D4 DBP-D4 98. 0 Sigma-Aldrich PAEs 5 16 17 2 2- - 4 di 2-ethylhexyl phthalate-3 4 5 6-D4 DEHP- 5 6 14-16 PAEs D4 95. 0 Dr. Ehrenstorfer Gmbh - SPE GC-MS 19 PAEs E PAEs 1 1. 1 19 PAEs 7890A GC-5975C MS - 100 mg /L Agilent Technologies KQ-400KDE DBP-D4 DEHP-D4 TGL-10B 100 mg /L DC-12H 4 Tedia 10 mg /L Fisher 1. 3 100 ~ 200 1. 3. 1 160 0. 50 g 10. 0 ml 180 12 h dimethyl phthalate DMP 97. 0 Dr. Ehrenstorfer Gmbh 1. 2 19 PAEs 40 ~ 50 15 min 2 000 r /min 5 min diethyl phthalate DEP 1 2 diallyl phthalate DAP 1. 0 ml dipropyl phthalate DPP 1. 3. 2 diisobutyl phthalate DIBP 800 mg 1 200 mg di-n-butyl phthalate DBP 4- -2- bis 4-methyl-2-pentyl phthalate 5 ml - 8 2 v /v BMPP diisopentyl phthalate 1. 3. 1 SPE 20 ml DIPP 2- bis 2-methoxyethyl phthalate DMEP - 8 2 v /v pentyl isopentyl phthalate PIPP SPE PAEs 2 ml /min di-n-pentyl phthalate DnPP DBP-D4 DEHP-

3-19 275 D4 50 μl 0. 5 ml GC-MS 1. 4 - PAEs 1. 0 μl DB-35 MS 30. 0 m 0. 25 mm 0. 25 μm 300 2 250 kpa 1. 0 min > 99. 999 He 1. 0 ml /min 2. 1 100 30 /min 220 5 /min 250 25 /min 320 5. 0 min electron DEHP-D4 1 ionization EI 70 ev 230 DBP DEHP 280 150 / Scan PAEs /SIM PAEs 3. 5 min 1 ± 20 1 19 PAEs 2 Table 1 PAE Retention times t R characteristic ions and their abundance ratios of 19 PAEs and 2 internal standards t R /min Characteristic ion m /z Abundance ratio DMP 4. 625 163 * 164 194 100 10 8 DEP 5. 230 149 * 150 177 176 100 13 27 10 DAP 6. 192 149 * 189 188 100 8 2 DPP 6. 247 149 * 209 191 100 7 6 DIBP 6. 745 149 * 205 223 100 3 6 DBP-D4 IS 7. 613 153 * 100 DBP 7. 632 149 * 205 223 100 4 5 BMPP 8. 217 149 * 167 85 100 47 44 DIPP 8. 487 149 * 237 219 100 12 3 DMEP 8. 637 59 * 58 104 149 100 70 38 24 PIPP 8. 945 149 * 237 219 100 6 1 DnPP 9. 429 149 * 237 219 100 7 1 BEEP 9. 606 72 * 73 193 149 100 95 8 66 DnHP 11. 206 149 * 150 251 100 9 8 BBP 11. 967 149 * 206 91 100 25 64 DEHP-D4 IS 12. 255 153 * 171 100 33 DEHP 12. 268 149 * 167 279 100 33 12 DHP 12. 395 149 * 150 265 100 8 10 DCHP 12. 922 149 * 167 249 100 32 18 DnOP 13. 324 149 * 150 279 100 10 9 DUP 17. 064 149 * 150 321 100 14 11 * Quantitative ion. IS internal standard. 1. 5 400 4 h 19 PAEs 1 1 DBP DBP-D4 DEHP PAEs 1 ~ 13 PAEs DBP-D4 14 ~ 21 PAEs DE- HP-D4 2. 2 2. 2. 1 0. 5 μg /g DCM EtAc Met Hex - Ace 1 1 v /v PAEs 1. 3 1. 4 1-1 1 v /v GC-MS PAEs 2 2 PAEs 0. 5 μg /g 3 a 10 ml 1 30 min b 20

276 30 1 a 19 PAEs b 0. 5 μg /g SIM Fig. 1 Selected ion monitoring chromatograms of a a mixed solution of 19 PAEs standards and b a shampoo sample spiked with 19 PAEs standards at 0. 5 μg /g Peaks 1. DMP 2. DEP 3. DAP 4. DPP 5. DIBP 6 and 7. DBP and DBP-D4 IS 8. BMPP 9. DIPP 10. DMEP 11. PIPP 12. Dn- PP 13. BEEP 14. DnHP 15. BBP 16 and 17. DEHP and DEHP-D4 IS 18. DHP 19. DCHP 20. DnOP 21. DUP. b 2 PAEs 3 3 PAEs Fig. 2 Efficiencies of extraction by different solvents for PAEs spiked in a shampoo sample Fig. 3 Influences of three different extraction procedures on the recoveries of PAEs spiked in a shampoo sample Extraction solvents Hex n-hexane DCM dichloromethane Met methanol EtAc ethyl acetate Hex-Ace n-hexane-acetone 1 1 v /v. ml 2 30 min 10 ml /15 min / c 30 ml 3 a. 10 ml /30 min /time one time b. 10 ml /15 min /time two times c. 10 ml /10 min /time three times. 2. 2. 2 30 min 10 ml /10 min / 1. 3. 2 1. 4 a b c 3

3-19 277 0. 1 μg /g 1. 3. 1 1. 4-2 g 4 6 m / m PAEs 4-8 2 v /v 20 ml PAEs 5 2 g 4 6 m /m - 20 ml 8 2 v /v - 5 - PAEs Fig. 5 Influences of different ratios of EtAc-Hex as eluents on the recoveries of PAEs spiked in a shampoo sample 4 - PAEs Fig. 4 Influences of mixture ratio of silica gel and neutral alumina as sorbents on the recoveries of PAEs spiked in a shampoo sample 2. 3 6 ~ 10 mg /L 0 0. 05 0. 1 0. 5 1. 0 2. 0 μg /g 5 0. 05 μg /g 0. 1 μg /g 6 1. 3 1. 4 RSD 19 PAEs r 0. 998 9 PAEs 72. 2 ~ 110. 9 RSD 4. 3 ~ 10. 3 LOD 0. 006 5 μg /g DIPP ~ 0. 062 μg /g DIBP 2 DIBP DBP DEHP 3 PAEs 0. 20 0. 02 0. 10 μg /g 2. 4 6 1. 3 1. 4 0. 1 1. 0 μg /g PAEs 6 x 25 ml 10 y 1. 0 μg /g r DBP DEHP 0. 05 μg /g 6 3 LOD 0. 1 0. 5 2. 0 μg /g 80. 0 ~ 116. 9 6 0. 1 μg /g 6 PAEs 5

278 30 PAEs 3 4 2 PAEs 2 19 PAEs RSD LOD Table 2 Calibration equations correlation coefficients r spiked recoveries relative standard deviations RSDs and limits of detection LODs of 19 PAEs PAE Calibration equation 1 r Spiked recovery / 0. 1 μg /g 0. 5 μg /g 2. 0 μg /g RSD n = 6 2 / LOD S /N = 3 3 / DMP y = 0. 4526x - 0. 0093 0. 9998 90. 8 84. 3 96. 2 5. 1 0. 0077 DEP y = 0. 5628x - 0. 0014 0. 9997 72. 2 85. 6 98. 0 4. 7 0. 0071 DAP y = 0. 209x - 0. 004 0. 9998 79. 3 96. 9 96. 7 6. 0 0. 0090 DPP y = 0. 8955x - 0. 0077 0. 9999 80. 7 92. 7 100. 7 5. 7 0. 0086 DIBP y = 0. 8886 + 0. 0844 0. 9996 101. 6 94. 6 104. 8 10. 3 0. 062 DBP y = 0. 9876x + 0. 0306 0. 9995 81. 1 94. 6 96. 4 7. 9 0. 012 BMPP y = 0. 4788x - 0. 0048 0. 9999 90. 3 102. 6 106. 9 8. 1 0. 012 DIPP y = 2. 7601x - 0. 0006 0. 9998 90. 1 95. 9 102. 3 4. 3 0. 0065 DMEP y = 0. 3564x - 0. 0022 0. 9998 94. 5 106. 0 109. 7 6. 7 0. 010 PIPP y = 0. 4119x + 0. 0002 0. 9994 93. 5 100. 9 105. 6 8. 0 0. 012 DnPP y = 1. 2505x - 0. 0051 0. 9997 92. 4 105. 2 110. 9 5. 4 0. 0081 BEEP y = 0. 1864x + 0. 00002 0. 9998 81. 6 108. 4 94. 2 5. 2 0. 0078 DnHP y = 2. 4276x + 0. 0046 0. 9997 99. 9 108. 1 109. 5 4. 4 0. 0066 BBP y = 0. 9323x - 0. 0037 0. 9998 83. 1 104. 4 105. 2 6. 9 0. 010 DEHP y = 1. 3674x + 0. 0796 0. 9996 96. 3 86. 5 92. 7 9. 4 0. 045 DHP y = 2. 4094x + 0. 0409 0. 9998 103. 7 99. 8 103. 8 4. 5 0. 0068 DCHP y = 1. 5362x + 0. 0093 0. 9994 85. 9 94. 0 99. 0 9. 3 0. 014 DnOP y = 2. 421x + 0. 002 0. 9998 103. 7 104. 9 99. 3 6. 7 0. 010 DUP y = 1. 9196x - 0. 0234 0. 9989 104. 6 97. 9 94. 0 7. 7 0. 012 1 x the spiked level y the peak area ratio of quantitative ions of analyte and IS. 2 The RSDs were obtained from the spike test at 0. 1 μg /g. 3 The LODs were obtained from the spike test at 0. 05 μg /g. 3 19 PAEs 1. 0 μg /g Table 3 Contents of 19 PAEs in smoothing toner mask powder and hand cream samples and recoveries of 19 PAEs spiked in 3 cosmetic samples at 1. 0 μg /g PAE Smoothing toner Mask powder Hand cream DMP 0. 93 n. d. 92. 8 0. 89 n. d. 89. 4 1. 023 0. 20 82. 6 DEP 1. 03 n. d. 103. 3 20. 51 19. 07-14. 99 13. 9 - DAP 0. 93 n. d. 92. 8 1. 06 n. d. 106. 2 1. 08 n. d. 107. 9 DPP 0. 89 n. d. 88. 7 0. 95 n. d. 95. 2 0. 81 n. d. 81. 3 DIBP 1. 09 0. 28 81. 4 3. 16 2. 29 86. 8 6. 65 5. 64 100. 9 DBP 1. 05 n. d. 104. 5 0. 99 n. d. 99. 2 0. 98 n. d. 97. 9 BMPP 0. 97 n. d. 97. 3 1. 02 n. d. 101. 6 1. 13 n. d. 113. 4 DIPP 1. 02 n. d. 102. 3 1. 07 n. d. 106. 6 1. 09 n. d. 109. 2 DMEP 0. 86 n. d. 86. 2 0. 89 n. d. 89. 4 0. 93 n. d. 93. 4 PIPP 0. 95 n. d. 94. 7 0. 93 n. d. 92. 8 1. 01 n. d. 101. 4 DnPP 0. 92 n. d. 91. 8 0. 94 n. d. 94. 0 0. 82 n. d. 82. 4 BEEP 1. 02 n. d. 102. 3 1. 01 n. d. 101. 4 0. 96 n. d. 96. 0 DnHP 0. 95 n. d. 94. 8 0. 91 n. d. 91. 4 1. 14 n. d. 113. 7 BBP 0. 98 n. d. 97. 6 0. 92 n. d. 92. 1 0. 95 n. d. 95. 0 DEHP 1. 07 0. 12 95. 1 1. 07 n. d. 107. 0 1. 17 n. d. 116. 9 DHP 0. 88 n. d. 87. 7 1. 02 n. d. 102. 2 1. 03 n. d. 103. 0 DCHP 0. 99 n. d. 98. 6 1. 04 n. d. 104. 2 0. 84 n. d. 84. 3 DnOP 0. 95 n. d. 94. 6 1. 06 n. d. 106. 0 1. 01 n. d. 101. 2 DUP 1. 05 n. d. 104. 6 0. 83 n. d. 83. 2 0. 90 n. d. 90. 1 n. d. The result was less than the LOD. - It is difficult to obtain accurate recovery because the content in the sample is too high.

3-19 279 PAE 4 19 PAEs 1. 0 μg /g Table 4 Contents of 19 PAEs in hair vaseline lotion and nail polish samples and recoveries of 19 PAEs spiked in 3 cosmetic samples at 1. 0 μg /g Hair vaseline Lotion Nail polish Original / DMP 0. 82 n. d. 82. 4 0. 89 n. d. 89. 0 5. 50 DEP 0. 87 n. d. 87. 2 0. 94 n. d. 93. 6 n. d. DAP 0. 81 n. d. 80. 8 0. 83 n. d. 83. 0 n. d. DPP 0. 91 n. d. 90. 8 0. 97 n. d. 96. 7 n. d. DIBP 1. 06 0. 24 82. 0 2. 01 0. 94 107. 0 22800 DBP 1. 05 n. d. 105. 2 1. 07 0. 21 86. 2 420 BMPP 0. 86 n. d. 86. 4 1. 03 n. d. 102. 8 n. d. DIPP 0. 80 n. d. 80. 0 0. 97 n. d. 97. 0 n. d. DMEP 1. 04 n. d. 104. 2 0. 99 n. d. 98. 8 n. d. PIPP 0. 86 n. d. 86. 0 0. 85 n. d. 85. 0 n. d. DnPP 0. 86 n. d. 85. 8 1. 10 n. d. 109. 6 n. d. BEEP 0. 82 n. d. 81. 8 0. 83 n. d. 82. 8 n. d. DnHP 0. 82 n. d. 82. 2 0. 98 n. d. 97. 6 n. d. BBP 0. 80 n. d. 80. 0 0. 99 n. d. 98. 8 n. d. DEHP 0. 84 n. d. 84. 0 1. 14 0. 23 91. 4 5980 DHP 0. 93 n. d. 93. 4 1. 02 n. d. 102. 2 n. d. DCHP 0. 84 n. d. 84. 4 0. 81 n. d. 81. 2 n. d. DnOP 1. 03 n. d. 102. 7 0. 98 n. d. 98. 0 n. d. DUP 0. 87 n. d. 87. 4 0. 80 n. d. 80. 4 n. d. n. d. The result was less than the LOD. - It is difficult to obtain accurate recovery because the content in the sample is too high. 3 GC-MS 19 PAEs - 19 PAEs 1 Staples C A Peterson D R Parkerton T F et al. Chemosphere 1997 35 4 667 2 Bai J R Teng J. Cosmetics Formulation and Application Examples. Beijing China Petrochemical Press.. 2003. 2009 10 3 Wang X Y Lin X T Ke H M et al. Journal of Environment and 5 20 Health. 15 Zhou X J Zhao Y Q Li W et al. China Surfactant Detergent & 2007 24 9 736 Cosmetics. 4 McKee R H Butala J H David R M et al. Reprod Toxicol 2004 18 1 1 5 Zheng H H Li J Wu D N et al. Chinese Journal of Analysis Laboratory. 2008 27 7 75 6 Chen H M Wang C Wang X et al. Journal of Instrumental A- nalysis. 2004 23 4 61 7 Jen J F Liu T C. J Chromatogr A 2006 1130 1 28 8 Liu C Li L S Wang S W et al. Chinese Journal of Chromatography. 2007 25 5 766 9 US EPA 8061A 10 Lin F Wen Y Y Hong X Y et al. Analytical Instrumentation. 2009 2 15 11 Earls A O Axford I P Braybrook J H. J Chromatogr A 2003 983 1 /2 237 12 Zhang L F Huang Y R Shi S X et al. Chromatography 2010 28 5 465 Chinese Journal of. 13 Zeng F Chen L X Cui K Y et al. Chinese Journal of Analytical Chemistry 2005 33 8 1063. 14 Wang F Zhang X Q Lu J et al. Flavour Fragrance Cosmetics 2010 40 2 148 16 Liu X P Huang W Li C Y et al. Journal of Environment and Health. 2007 24 11 915 17 Shen H Y Jiang H L Mao H L et al. J Sep Sci 2007 30 48

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