分散固相萃取结合气相色谱-串联质谱法测定化妆品中 18种有机磷酸酯

doi:10.3969/j.issn.2097-2806.2026.09.015

Abstract

Abstract:

A method was established for the determination of 18 organophosphate esters in cosmetics by dispersive solid-phase extraction coupled with gas chromatography-tandem mass spectrometry （GC-MS/MS）. The samples were extracted with acetonitrile and purified with an HMR-Lipid sorbent, separated on an HP-5MS UI chromatographic column （30.0 m× 0.25 mm, 0.25 μm）, monitored in dynamic multiple reaction monitoring （dMRM） mode, and quantified by the internal standard method. The results show good linearity for all 18 organophosphate esters, with correlation coefficients （R²） greater than 0.99. The limits of detection range from 0.001 to 0.050 mg/kg, and the limits of quantitation are 0.003-0.100 mg/kg. The average recoveries at low, medium and high spiking levels are between 85.8% and 110.6%, with relative standard deviations less than 9.9%. The method features simple sample preparation, rapid and efficient analysis, and accurate quantification, making it suitable for the qualitative and quantitative determination of 18 organophosphate esters in cosmetics.

Key words: HMR-Lipid sorbent, gas chromatography-tandem mass spectrometry, cosmetics, organophosphate esters

CLC Number:

TQ658

Mengli Huang, Gaiqing Jiang, Xueyin Li, Bowen Zhang, Xiaojie Sun. Determination of 18 organophosphate esters in cosmetics by dispersive solid-phase extraction coupled with gas chromatography-tandem mass spectrometry[J].China Surfactant Detergent & Cosmetics, 2026, 56(9): 1260-1268.

Figures/Tables 5

Tab.1

Mass spectrometry parameters of the 18 organophosphate esters and 11 internal standards"

化合物名称（简称）	保留时间/min	特征离子对（m/z）	碰撞能量/V	对应内标
磷酸三甲酯（TMP）	3.633	110>46.9^*，110>79，140>79	50， 15， 20	TMP-D₉
磷酸三乙酯（TEP）	4.457	155>99.1^*，127>99，99>81	10， 5， 15	TEP-D₁₅
磷酸三异丙基酯（TiPP）	4.736	99>81^*，141>99，123>41.1	20， 5， 20	TPrP-D₂₁
磷酸三丙酯（TPrP）	5.550	99>81^*，141>99，99>63	20， 5， 10	TPrP-D₂₁
磷酸三异丁酯（TiBP）	6.250	139>81^*，139>99，99>81	30， 10， 20	TnBP-D₂₇
TnBP	7.046	99>62.9^*，155>99.1，99>81	40， 5， 20	TnBP-D₂₇
TCEP	7.921	143>116.9^*，205>63，143>81	10， 15， 25	TCEP-D₁₂
TCPP	8.211	125>99^*，201>99，98.9>80.9	15， 30， 20	TCPP-D₁₈
磷酸三正戊酯（TPeP）	9.069	169>99^*，99>81，239>99	5， 20， 5	TCPP-D₁₈
TDCPP	12.499	208.9>99^*，190.9>75，190.9>57	5， 10， 15	TDCPP-D₁₅
三（2-丁氧基乙基）磷酸酯（TBEP）	12.963	125>45.1^*，125>98.9，125>81.1	20， 15， 30	TBEP-D₂₇
TPhP	13.022	214.9>168^*，325.9>215，325.9>170	20， 25， 20	TPhP-D₁₅
2-乙基己基二苯基磷酸酯（DPOP）	13.201	251>77.1^*，251>153.1，249>169	30， 40， 20	TPhP-D₁₅
磷酸三（2-乙基己基酯）（TEHP）	13.413	99>81^*，99>63，112>81.9	20， 40， 10	TEHP-D₅₁
CDP	13.672	339.8>182.9^*，339.8>107.9	30， 20， 25	p-TCP-D₂₁
o-TCP	13.472	368>165.1^*，277>179.1，165>164	40， 15， 5	p-TCP-D₂₁
m-TCP	14.881	367.9>164.9^*，367.9>198.1	40， 20	p-TCP-D₂₁
磷酸三对甲苯酯（p-TCP）	15.545	368>165^*，261>243，261>196	30， 10， 25	p-TCP-D₂₁
磷酸三甲酯-D₉（TMP-D₉）	3.605	117>83^*，117>47，149>83	15， 30， 25
磷酸三乙酯-D₁₅（TEP-D₁₅）	4.423	167>103^*，135>103，135>83	15， 10， 30
磷酸三丙酯-D₂₁（TPrP-D₂₁）	5.489	103>83^*，151>103，131>46.1	25， 5， 20
磷酸三丁酯-D₂₇（TnBP-D₂₇）	6.928	103>83^*，167>103，231>103	25， 5， 10
磷酸三（2-氯乙基）酯-D₁₂（TCEP-D₁₂）	7.836	261>67^*，261>131，213>67	20， 10， 15
磷酸三（1-氯-2-丙基）酯-D₁₈（TCPP-D₁₈）	8.105	103>83^*，131>103，164>120	20， 15， 10
磷酸三（1，3-二氯-2-丙基） -D₁₅（TDCPP-D₁₅）	12.369	103>83^*，217>103，196.9>79	20， 10， 15
三（2-丁氧基乙基）磷酸酯-D₂₇（TBEP-D₂₇）	12.806	154>99.9^*，154>126.1，125.9>100	25， 5， 15
磷酸三苯酯-D₁₅（TPhP-D₁₅）	12.953	223>176.1^*，341>180.2，243>223	25， 20， 15
磷酸三（2-乙基己基）酯-D₅₁（TEHP-D₅₁）	13.147	103>83^*，130>50.1	25， 15
p-TCP-D₂₁	15.429	389>116.1^*，389>174.1，389>275	30， 40， 15

Tab.1

Fig.1

Tab.2

Tab.3

Linear equations, correlation coefficients （R2）, linear ranges, limits of detection （LODs）, limits of quantitation （LOQs） and matrix effects （MEs） of 18 organophosphate esters in three cosmetic matrices"

化合物名称	基质种类	线性方程	R²	线性范围/ （ng/mL）	LOD/ （mg/kg）	LOQ/ （mg/kg）	ME
TMP	爽肤水	Y=1.927X-0.011	0.999	0.5~100	0.010	0.020	0.96
	面霜	Y=0.855X-0.002	0.999	0.5~100	0.010	0.020	0.43
	卸妆油	Y=2.114X-0.022	0.999	0.5~100	0.010	0.020	1.06
TEP	爽肤水	Y=2.129X-0.019	0.999	0.5~100	0.010	0.020	1.05
	面霜	Y=2.092X-0.046	0.999	0.5~100	0.010	0.020	1.04
	卸妆油	Y=2.107X-0.018	0.999	0.5~100	0.010	0.020	1.04
TiPP	爽肤水	Y=4.110X-0.012	0.999	0.5~60	0.002	0.005	0.99
	面霜	Y=4.137X+0.190	0.997	0.5~60	0.002	0.005	0.99
	卸妆油	Y=4.598X-0.040	0.999	0.5~60	0.002	0.005	1.10
TPrP	爽肤水	Y=5.413X-0.023	0.999	0.5~60	0.002	0.005	0.90
	面霜	Y=6.209X-0.020	0.999	0.5~60	0.002	0.005	1.03
	卸妆油	Y=6.302X-0.038	0.999	0.5~60	0.002	0.005	1.05
TiBP	爽肤水	Y=0.248X+0.018	0.999	0.5~60	0.001	0.003	0.03
	面霜	Y=0.123X-0.001	0.999	0.5~60	0.001	0.003	0.01
	卸妆油	Y=0.236X+0.020	0.999	0.5~60	0.001	0.003	0.03
TnBP	爽肤水	Y=1.230X-0.018	0.999	0.5~60	0.001	0.003	0.96
	面霜	Y=1.270X-0.023	0.999	0.5~60	0.001	0.003	0.99
	卸妆油	Y=1.298X+0.007	0.999	0.5~60	0.001	0.003	1.01
TCEP	爽肤水	Y=1.835X+0.009	0.998	0.5~100	0.020	0.050	0.97
	面霜	Y=2.376X-0.039	0.998	0.5~100	0.020	0.050	1.26
	卸妆油	Y=1.903X-0.041	0.999	0.5~100	0.020	0.050	1.01
TCPP	爽肤水	Y=1.450X+0.011	0.999	0.5~100	0.020	0.050	1.03
	面霜	Y=1.581X-0.013	0.999	0.5~100	0.020	0.050	1.12
	卸妆油	Y=1.210X-0.025	0.999	0.5~100	0.020	0.050	0.86
TPeP	爽肤水	Y=1.356X-0.044	0.999	0.5~100	0.020	0.050	1.60
	面霜	Y=2.677X-0.043	0.999	0.5~100	0.020	0.050	3.17
	卸妆油	Y=2.387X-0.072	0.999	0.5~100	0.020	0.050	2.82
TDCPP	爽肤水	Y=0.628X+0.006	0.999	0.5~100	0.020	0.050	1.10
	面霜	Y=0.749X-0.016	0.999	0.5~100	0.020	0.050	1.31
	卸妆油	Y=0.675X+0.004	0.999	0.5~100	0.020	0.050	1.18
TBEP	爽肤水	Y=3.933X-0.150	0.999	0.5~100	0.050	0.100	4.07
	面霜	Y=4.835X+0.141	0.999	0.5~100	0.050	0.100	5.01
	卸妆油	Y=5.020X+0.009	0.999	0.5~100	0.050	0.100	5.20
TPhP	爽肤水	Y=2.712X+0.005	0.999	0.5~100	0.020	0.050	0.86
	面霜	Y=2.747X+0.009	0.999	0.5~100	0.020	0.050	0.87
	卸妆油	Y=3.176X-0.021	0.999	0.5~100	0.020	0.050	1.01
DPOP	爽肤水	Y=7.062X-0.344	0.998	0.5~100	0.020	0.050	1.50
	面霜	Y=11.67X+0.054	0.999	0.5~100	0.020	0.050	2.48
	卸妆油	Y=13.43X-0.151	0.998	0.5~100	0.020	0.050	2.85
TEHP	爽肤水	Y=1.224X-0.019	0.999	0.5~100	0.010	0.030	1.03
	面霜	Y=1.438X-0.016	0.999	0.5~100	0.010	0.030	1.22
	卸妆油	Y=1.509X+0.114	0.998	0.5~100	0.010	0.030	1.28
CDP	爽肤水	Y=1.013X+0.040	0.999	0.5~100	0.050	0.100	0.81
	面霜	Y=0.928X-0.015	0.999	0.5~100	0.050	0.100	0.74
	卸妆油	Y=0.853X+0.001	0.998	0.5~100	0.050	0.100	0.68
o-TCP	爽肤水	Y=19.12X+0.700	0.999	0.5~100	0.020	0.050	0.88
	面霜	Y=13.83X-0.028	0.999	0.5~100	0.020	0.050	0.64
	卸妆油	Y=13.65X-0.205	0.999	0.5~100	0.020	0.050	0.63
m-TCP	爽肤水	Y=19.32X-0.106	0.999	0.5~100	0.020	0.050	1.21
	面霜	Y=18.44X-0.160	0.999	0.5~100	0.020	0.050	1.16
	卸妆油	Y=17.63X-0.162	0.999	0.5~100	0.020	0.050	1.11
p-TCP	爽肤水	Y=8.378X-0.068	0.999	0.5~100	0.020	0.050	1.18
	面霜	Y=8.762X-0.019	0.999	0.5~100	0.020	0.050	1.23
	卸妆油	Y=8.551X-0.101	0.999	0.5~100	0.020	0.050	1.20

Tab.3

Tab.4

Average recoveries and relative standard deviations of 18 organophosphate esters in three cosmetic matrices （n=6）"

名称	爽肤水			面霜			卸妆油
名称	添加水平/ （mg/kg）	回收率/%	RSD/%	添加水平/ （mg/kg）	回收率/%	RSD/%	添加水平/ （mg/kg）	回收率/%	RSD/%
TMP	0.1	89.4	6.6	0.1	97.0	4.3	0.1	91.1	4.3
	0.3	91.1	5.4	0.3	93.8	1.1	0.3	99.4	4.6
	0.5	96.4	1.9	0.5	97.8	1.6	0.5	97.0	1.8
TEP	0.1	91.5	2.4	0.1	91.2	1.9	0.1	95.2	1.6
	0.3	88.0	4.6	0.3	93.7	2.9	0.3	106.8	4.2
	0.5	90.1	1.9	0.5	91.9	2.6	0.5	100.3	4.9
TiPP	0.1	88.0	6.1	0.1	93.4	6.9	0.1	99.8	6.1
	0.3	96.3	5.2	0.3	95.4	7.8	0.3	97.3	3.8
	0.5	98.9	4.1	0.5	95.3	5.1	0.5	97.6	4.8
TPrP	0.1	98.3	8.8	0.1	94.4	3.1	0.1	94.9	7.1
	0.3	104.1	8.0	0.3	89.3	8.2	0.3	97.4	3.2
	0.5	93.1	5.8	0.5	99.5	8.7	0.5	92.2	8.5
TiBP	0.1	97.8	8.1	0.1	97.6	1.9	0.1	89.6	8.1
	0.3	89.7	2.8	0.3	86.8	2.4	0.3	109.6	5.5
	0.5	92.5	8.9	0.5	91.2	8.1	0.5	100.9	8.1
TnBP	0.1	89.5	9.1	0.1	93.4	6.5	0.1	101.3	8.6
	0.3	89.2	6.2	0.3	91.8	5.8	0.3	99.7	4.5
	0.5	88.4	6.7	0.5	92.2	6.9	0.5	99.3	5.9
TCEP	0.1	96.0	5.1	0.1	93.2	4.1	0.1	96.0	5.1
	0.3	94.2	4.2	0.3	91.5	5.3	0.3	97.6	6.4
	0.5	103.4	4.1	0.5	95.9	4.2	0.5	95.8	3.6
TCPP	0.1	98.0	3.3	0.1	93.6	4.2	0.1	92.9	4.0
	0.3	90.2	3.1	0.3	92.5	3.5	0.3	97.1	6.6
	0.5	92.5	3.4	0.5	93.0	3.4	0.5	95.1	5.6
TPeP	0.1	91.4	9.1	0.1	96.3	7.6	0.1	100.5	8.3
	0.3	96.8	4.4	0.3	96.5	8.9	0.3	91.4	5.3
	0.5	110.6	4.7	0.5	91.7	4.7	0.5	86.3	4.9
TDCPP	0.1	99.6	4.9	0.1	92.1	5.3	0.1	91.0	7.5
	0.3	95.5	9.9	0.3	86.4	6.8	0.3	95.7	8.0
	0.5	93.0	5.2	0.5	102.8	2.7	0.5	93.0	7.8
TBEP	0.1	97.5	3.3	0.1	99.7	3.6	0.1	87.6	9.2
	0.3	91.6	2.8	0.3	86.0	3.6	0.3	105.3	4.9
	0.5	102.1	6.7	0.5	92.4	5.2	0.5	96.6	9.5
TPhP	0.1	90.4	7.1	0.1	91.7	5.8	0.1	94.0	6.2
	0.3	92.9	6.0	0.3	89.2	5.1	0.3	95.0	5.3
	0.5	95.1	6.8	0.5	90.6	4.3	0.5	94.5	5.9
DPOP	0.1	99.0	5.2	0.1	101.2	4.5	0.1	99.0	5.2
	0.3	96.9	4.8	0.3	98.4	2.3	0.3	100.8	4.3
	0.5	105.1	7.0	0.5	99.2	2.6	0.5	101.3	2.2
TEHP	0.1	99.4	5.9	0.1	98.3	2.6	0.1	98.6	2.7
	0.3	93.2	6.6	0.3	97.8	2.8	0.3	92.4	2.9
	0.5	96.5	5.3	0.5	95.8	2.6	0.5	95.2	5.8
CDP	0.1	94.6	6.7	0.1	101.4	4.5	0.1	106.0	5.4
	0.3	101.2	4.2	0.3	97.1	2.4	0.3	104.9	3.6
	0.5	107.1	2.9	0.5	94.5	2.2	0.5	98.8	1.8
o-TCP	0.1	104.7	4.6	0.1	101.1	3.6	0.1	99.7	2.1
	0.3	91.9	5.6	0.3	98.5	8.8	0.3	109.0	7.9
	0.5	102.7	6.4	0.5	105.5	3.5	0.5	91.8	6.5
m-TCP	0.1	106.3	2.7	0.1	106.3	3.2	0.1	85.8	1.6
	0.3	95.2	3.7	0.3	90.5	3.4	0.3	106.5	4.6
	0.5	95.1	9.2	0.5	91.6	6.9	0.5	97.1	9.6
p-TCP	0.1	88.1	5.6	0.1	95.3	5.0	0.1	92.3	9.0
	0.3	92.8	6.8	0.3	92.6	4.5	0.3	95.0	7.6
	0.5	95.9	5.0	0.5	93.8	5.3	0.5	93.8	6.7

Tab.4

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化合物名称	回收率/%
	水乳膏霜基质					油基质
	净化填料A	净化填料B	净化填料C	净化填料D	净化填料E	净化填料A	净化填料B	净化填料C	净化填料D	净化填料E
TMP	84.2	85.2	84.8	84.1	86.2	103.2	101.1	108.3	107.6	110.7
TEP	93.6	93.8	89.3	95.8	104.7	99.5	97.7	100.6	98.6	111.2
TiPP	91.5	94.2	89.9	93.6	98.9	90.3	87.7	91.6	89.1	92.1
TPrP	92.1	90.8	87.9	93.5	96.8	92.9	90.9	92.6	86.8	95.7
TiBP	96.5	94.6	93.4	94.2	98.9	94.3	97.3	97.9	88.2	97.2
TnBP	93.5	92.4	92.5	95.9	99.0	95.2	101	98.2	90.5	97.5
TCEP	86.1	74.7	76.2	81.2	84.9	111.8	104.4	111.6	101.4	112.3
TCPP	94.4	97.9	88.4	91.8	95.1	103.7	91.2	109.4	92.4	95.3
TPeP	80.6	84.5	83.2	81.5	96.1	94.6	99.3	104.2	98.7	99.2
TDCPP	94.3	74.4	80.2	92.7	100.6	70.5	77.5	78.8	79.4	88.5
TBEP	70.7	80.1	67.6	71.2	82.7	102.2	98.2	87.2	86.3	97.4
TPhP	85.6	88.9	84.1	92.3	92.9	86.5	84.2	85.7	88.1	90.9
DPOP	81.1	95.8	83.4	87.7	96.7	95.0	85.9	92.8	90.6	97.6
TEHP	90.5	90.1	87.5	94.9	98.2	90.0	89.8	92.5	89.1	90.3
CDP	101.5	99.2	80.6	103	108.5	79.8	72.3	77.5	81.7	81.2
o-TCP	102.5	107.1	80.2	105.5	106.9	89.8	90.2	92.1	82.2	87.6
m-TCP	100.8	93.3	100.5	100.5	98.9	83.4	88.3	90.5	86.4	86.8
p-TCP	95.9	85.4	82.1	103.3	101.4	88.5	89.9	94.8	90.5	92.7

Determination of 18 organophosphate esters in cosmetics by dispersive solid-phase extraction coupled with gas chromatography-tandem mass spectrometry

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