Determination of 26 bisphenols in dust by ultra performance liquid chromatography-tandem mass spectrometry

doi:10.3724/SP.J.1123.2022.08022

Abstract

Abstract:

Bisphenol A (BPA) is one of the most widely produced compounds in the world and was listed as a substance of very high concern by the European Chemicals Agency in 2016. Because of its toxicity, many countries and regions, including China, have banned BPA addition in feeding-bottles. And the European Union (EU) has banned BPA use in other food contact materials and thermal paper. Restrictions on BPA have contributed to the widespread use of alternatives. As the toxicity of BPA alternatives continues to be revealed, the alternatives of BPA alternatives are being developing. As the most extensive alternative for BPA, bisphenol S (BPS) was proven to have estrogen-disrupting effects and developmental toxicity of the neuroendocrine system. Therefore, BPS alternatives are used in thermal paper. In this study, alternatives to both BPA and BPS are collectively referred to as bisphenols (BPs). As a pooling matrix of many indoor chemicals, dust is an important pathway for human exposure to BPs. BPA and its alternatives are routinely detected in dust. As BPS alternatives have been detected in recycled paper and sludge, it is also very important to detected in dust. However, common analytical methods for BPs have low sensitivity and contain few BPS alternatives. Therefore, a high-throughput, high-accuracy, and high-sensitivity method must be established for the determination of BPs in dust; this will lay the foundation for subsequent studies on the environmental behavior and exposure risk of BPs.

In this study, an ultra performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) method was developed for the simultaneous determination of 26 variations of BPs in dust. UPLC-MS/MS parameters of the variations were optimized to compare the separation effect and response intensity in different columns and mobile phases. The influence of the extraction solvent and solid phase extraction (SPE) on the extraction efficiency and purification effect of target compounds were optimized by using the isotopic internal standard method, and the 26 variations of BPs in dust was quantitatively analyzed. Finally, the dust samples were extracted by using 3 mL of acetonitrile and 3 mL of a 50% methanol aqueous solution in an ultrasound bath. The combined extract was further purified by using an Oasis HLB cartridge (60 mg/3 mL). The cartridge was then washed with a 40% methanol aqueous solution (0.5 mL) and eluted with methanol (2 mL). The target compounds were separated on a CORTECS^® UPLC^® C₁₈ column (100 mm×2.1 mm, 1.6 μm), with methanol and 1 mmol/L ammonium fluoride solution as mobile phases and a flow rate of 0.3 mL/min. Electrospray ionization (ESI) was applied in the positive, negative, and multiple reaction monitoring (MRM) modes for the mass scan. Under optimized conditions, the linear ranges of the 26 targets behaved well linearly in their respective ranges with correlation coefficients (r²)>0.999. The limits of detection (LODs) and limits of quantification (LOQs) were assessed using signal-to-noise (S/N) ratios of 3 and 10, respectively. The LODs and LOQs of the method were 0.01-0.75 μg/kg and 0.02-2.50 μg/kg, respectively. The accuracy of the method was evaluated by conducting a recovery test at three spiked levels: LOQ, two times the LOQ, and 10 times the LOQ, with the average recoveries ranging from 83.7% to 114.9%. The precision of the method was evaluated by using the relative standard deviation (RSD). The intra-day RSDs and inter-day RSDs were 0.86%-9.79% (n=6) and 5.16%-19.5% (n=6), respectively. The established method was used to determine 11 dust samples. Fifteen BPs were detected at a detection rate of 9.1%-100.0%. The detection rate for BPA, BPS, bisphenol F (BPF), 4-hydroxy-4'-isopropoxydiphenylsulfone (BPSIP), and diphenyl sulfone (DPS) was 100.0%. BPSIP, 4-allyloxy-4'-hydroxydiphenyl sulfone (BPS-MAE), and bis-(3-allyl-4-hydroxyphenyl) sulfone (TGSA) were first detected in Chinese dust, whereas 4-benzyloxy-4'-hydroxydiphenyl sulfone (BPS-MPE), 4-hydroxybenzoic acid benzyl (PHBB), and DPS were first detected in dust samples worldwide. This method is simple, rapid, and sensitive, and is suitable for the qualitative screening and quantitative analysis of the 26 BPs in dust samples.

Key words: ultra performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS), bisphenols (BPs), dust

CLC Number:

O658

SUN Jialin, NIU Yumin, GAO Qun, ZHANG Jing, SHAO Bing. Determination of 26 bisphenols in dust by ultra performance liquid chromatography-tandem mass spectrometry[J]. Chinese Journal of Chromatography, 2023, 41(5): 417-425.

Figures/Tables 5

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Compound	Retention time/min	Precursor ion (m/z)	Daughter ion (m/z)	Collision energy/eV	Declustering potential/V	IS
Bisphenol S (BPS)	1.90	249	108^*	-35	-80	BPS-¹³C₁₂
			92	-35	-80
2,4'-Dihydroxydiphenyl sulfone (2,4-BPS)	2.26	249	107.9^*	-34	-60	2,4-BPS-d₈
			156	-22	-60
4,4'-Dihydroxydiphenyl ether (DHDPE)	2.49	201	108^*	-21	-60	BPF-¹³C₁₂
			173	-21	-60
Bisphenol F (BPF)	2.96	199	93^*	-34	-80	BPF-¹³C₁₂
			105	-30	-80
Bisphenol E (BPE)	3.27	213	198^*	-32	-80	BPE-¹³C₆
			197	-22	-60
Bisphenol T (BPT)	3.28	217	124^*	-29	-50	BPS-¹³C₁₂
			185	-30	-50
Bis(2-chloroethyl)ether-4,4'-dihydroxydiphenyl	3.36	569	411^*	-36	-80	BPS-¹³C₁₂
sulfone copolymer (D-90(n=1))			249.1	-35	-100
4-Allyloxy-4'-hydroxydiphenyl sulfone (BPS-MAE)	3.42	289	248^*	-38	-60	BPS-¹³C₁₂
			184	-20	-50
Bisphenol A (BPA)	3.54	227	212^*	-26	-60	BPA-¹³C₁₂
			133	-29	-100
4-Hydroxy-4'-isopropoxydiphenyl sulfone (BPSIP)	3.55	291	248^*	-30	-80	BPSIP-d₇
			184	-35	-100
Bis-(3-allyl-4-hydroxyphenyl) sulfone (TGSA)	3.72	329	132^*	-43	-120	BPS-¹³C₁₂
			148	-37	-120
Tetrachlorobisphenol A (TCBPA)	3.73	329	250^*	-42	-120	TCBPA-¹³C₁₂
			278	-33	-120
Monochloro bisphenol A (MCBPA)	3.90	261	182^*	-42	-100	BPA-¹³C₁₂
			167	-50	-100
4-Hydroxybenzoic acid benzyl (PHBB)	3.93	227	92^*	-27	-60	PHBB-¹³C₆
			136	-23	-60
4-Benzyloxy-4'-hydroxydiphenyl sulphone	4.00	339	248^*	-27	-60	BPS-¹³C₁₂
(BPS-MPE)			108	-42	-100
Bisphenol AF (BPAF)	4.01	335	265^*	-25	-60	BPAF-d₄
			197	-56	-60
Bisphenol AP (BPAP)	4.07	289	274^*	-29	-100	BPAP-¹³C₆
			195	-40	-50
3,3-Dichloro bisphenol A (3,3-DCBPA)	4.20	297	246^*	-36	-60	BPA-¹³C₁₂
			218	-23	-100
3,5-Dichloro bisphenol A (3,5-DCBPA)	4.21	297	216^*	-41	-100	BPA-¹³C₁₂
			244	-34	-100
Bisphenol FL (BPFL)	4.24	349	256^*	-36	-100	BPA-¹³C₁₂
			215	-36	-120
Bisphenol Z (BPZ)	4.27	267	173^*	-37	-100	BPZ-¹³C₁₂
			223	-37	-120
3,3',5-Trichloro bisphenol (TriCBPA)	4.48	331	252^*	-43	-120	BPA-¹³C₁₂
			280	-36	-80
Bisphenol TMC (BPTMC)	4.86	309	215^*	-42	-120	BPA-¹³C₁₂
			200	-34	-100
Tetrabromobisphenol A (TBBPA)	4.93	545	420^*	-50	-120	TBBPA-¹³C₁₂
			448	-54	-120
diphenyl sulfone (DPS)	3.09	219	77^*	30	100	BPS-¹³C₁₂
			141	30	80
Bis(4-allyloxyphenyl)sulfone (BPS-DAE)	4.33	331	197^*	24	120	BPS-¹³C₁₂
			79	37	120
BPS-¹³C₁₂	1.90	261	114	-35	-100
2,4-BPS-d₈	2.26	257	112	-31	-60
BPF-¹³C₁₂	2.96	211	99	-30	-80
BPE-¹³C₆	3.27	219	204	-27	-80
BPA-¹³C₁₂	3.54	239	224	-25	-80
BPSIP-d₇	3.55	298	250	-26	-100
TCBPA-¹³C₁₂	3.73	661	440	-45	-120
PHBB-¹³C₆	3.93	233	98	-25	-60
BPAF-d₄	4.01	339	269	-24	-60
BPAP-¹³C₆	4.07	295	280	-29	-100
BPZ-¹³C₁₂	4.27	279	235	-37	-80
TBBPA-¹³C₁₂	4.93	838	617	-50	-120

Compound	Retention time/min	Precursor ion (m/z)	Daughter ion (m/z)	Collision energy/eV	Declustering potential/V	IS
Bisphenol S (BPS)	1.90	249	108^*	-35	-80	BPS-¹³C₁₂
			92	-35	-80
2,4'-Dihydroxydiphenyl sulfone (2,4-BPS)	2.26	249	107.9^*	-34	-60	2,4-BPS-d₈
			156	-22	-60
4,4'-Dihydroxydiphenyl ether (DHDPE)	2.49	201	108^*	-21	-60	BPF-¹³C₁₂
			173	-21	-60
Bisphenol F (BPF)	2.96	199	93^*	-34	-80	BPF-¹³C₁₂
			105	-30	-80
Bisphenol E (BPE)	3.27	213	198^*	-32	-80	BPE-¹³C₆
			197	-22	-60
Bisphenol T (BPT)	3.28	217	124^*	-29	-50	BPS-¹³C₁₂
			185	-30	-50
Bis(2-chloroethyl)ether-4,4'-dihydroxydiphenyl	3.36	569	411^*	-36	-80	BPS-¹³C₁₂
sulfone copolymer (D-90(n=1))			249.1	-35	-100
4-Allyloxy-4'-hydroxydiphenyl sulfone (BPS-MAE)	3.42	289	248^*	-38	-60	BPS-¹³C₁₂
			184	-20	-50
Bisphenol A (BPA)	3.54	227	212^*	-26	-60	BPA-¹³C₁₂
			133	-29	-100
4-Hydroxy-4'-isopropoxydiphenyl sulfone (BPSIP)	3.55	291	248^*	-30	-80	BPSIP-d₇
			184	-35	-100
Bis-(3-allyl-4-hydroxyphenyl) sulfone (TGSA)	3.72	329	132^*	-43	-120	BPS-¹³C₁₂
			148	-37	-120
Tetrachlorobisphenol A (TCBPA)	3.73	329	250^*	-42	-120	TCBPA-¹³C₁₂
			278	-33	-120
Monochloro bisphenol A (MCBPA)	3.90	261	182^*	-42	-100	BPA-¹³C₁₂
			167	-50	-100
4-Hydroxybenzoic acid benzyl (PHBB)	3.93	227	92^*	-27	-60	PHBB-¹³C₆
			136	-23	-60
4-Benzyloxy-4'-hydroxydiphenyl sulphone	4.00	339	248^*	-27	-60	BPS-¹³C₁₂
(BPS-MPE)			108	-42	-100
Bisphenol AF (BPAF)	4.01	335	265^*	-25	-60	BPAF-d₄
			197	-56	-60
Bisphenol AP (BPAP)	4.07	289	274^*	-29	-100	BPAP-¹³C₆
			195	-40	-50
3,3-Dichloro bisphenol A (3,3-DCBPA)	4.20	297	246^*	-36	-60	BPA-¹³C₁₂
			218	-23	-100
3,5-Dichloro bisphenol A (3,5-DCBPA)	4.21	297	216^*	-41	-100	BPA-¹³C₁₂
			244	-34	-100
Bisphenol FL (BPFL)	4.24	349	256^*	-36	-100	BPA-¹³C₁₂
			215	-36	-120
Bisphenol Z (BPZ)	4.27	267	173^*	-37	-100	BPZ-¹³C₁₂
			223	-37	-120
3,3',5-Trichloro bisphenol (TriCBPA)	4.48	331	252^*	-43	-120	BPA-¹³C₁₂
			280	-36	-80
Bisphenol TMC (BPTMC)	4.86	309	215^*	-42	-120	BPA-¹³C₁₂
			200	-34	-100
Tetrabromobisphenol A (TBBPA)	4.93	545	420^*	-50	-120	TBBPA-¹³C₁₂
			448	-54	-120
diphenyl sulfone (DPS)	3.09	219	77^*	30	100	BPS-¹³C₁₂
			141	30	80
Bis(4-allyloxyphenyl)sulfone (BPS-DAE)	4.33	331	197^*	24	120	BPS-¹³C₁₂
			79	37	120
BPS-¹³C₁₂	1.90	261	114	-35	-100
2,4-BPS-d₈	2.26	257	112	-31	-60
BPF-¹³C₁₂	2.96	211	99	-30	-80
BPE-¹³C₆	3.27	219	204	-27	-80
BPA-¹³C₁₂	3.54	239	224	-25	-80
BPSIP-d₇	3.55	298	250	-26	-100
TCBPA-¹³C₁₂	3.73	661	440	-45	-120
PHBB-¹³C₆	3.93	233	98	-25	-60
BPAF-d₄	4.01	339	269	-24	-60
BPAP-¹³C₆	4.07	295	280	-29	-100
BPZ-¹³C₁₂	4.27	279	235	-37	-80
TBBPA-¹³C₁₂	4.93	838	617	-50	-120

Compound	Linear range/(μg/L)	Linear equation	r²	LOD/ (μg/kg)	LOQ/ (μg/kg)	Recoveries/%			Intra-day RSD/%	Inter-day RSD/%
Compound	Linear range/(μg/L)	Linear equation	r²	LOD/ (μg/kg)	LOQ/ (μg/kg)	LOQ	2LOQ	10LOQ	Intra-day RSD/%	Inter-day RSD/%
BPS	0.10-50	Y=0.09684X+0.08569	0.9999	0.03	0.10	109.6	92.3	100.9	2.12	5.41
2,4-BPS	0.25-50	Y=0.04661X+0.00363	0.9994	0.08	0.25	98.9	101.3	100.2	2.54	6.93
DHDPE	0.50-50	Y=0.01898X+0.00304	0.9992	0.15	0.50	98.5	101.4	100.1	5.45	8.24
BPF	2.50-50	Y=0.09588X+0.00842	0.9999	0.75	2.50	100.6	101.2	100.6	3.42	16.5
BPE	0.50-50	Y=0.06569X+0.01917	0.9999	0.15	0.50	101.9	100.1	102.5	4.17	6.68
BPT	0.10-50	Y=0.81667X+0.02810	0.9995	0.03	0.10	97.5	100.2	83.7	5.59	11.6
D-90(n=1)	2.50-50	Y=0.00212X+3.10855	0.9999	0.75	2.50	99.7	97.2	96.4	5.80	6.37
BPS-MAE	0.02-50	Y=0.76816X+0.02221	0.9995	0.01	0.02	105.1	97.8	101.4	1.44	7.13
BPA	0.50-50	Y=0.13014X+0.05599	0.9992	0.15	0.50	99.9	100.5	122.2	1.78	19.5
BPSIP	0.02-50	Y=0.71425X+0.06079	0.9995	0.02	0.05	103.5	99.8	100.4	3.67	5.79
TGSA	0.05-50	Y=1.03445X+0.12088	0.9998	0.02	0.05	101.2	102.9	100.3	2.16	11.5
TCBPA	0.05-50	Y=1.03451X+0.14530	0.9995	0.02	0.05	93.1	100.3	96.3	3.20	7.09
MCBPA	0.20-50	Y=0.14550X+0.01068	0.9991	0.06	0.20	99.2	99.9	100.4	2.33	7.35
PHBB	0.10-50	Y=0.08620X+0.01208	0.9994	0.03	0.10	100.1	100.3	97.9	3.58	7.12
BPS-MPE	0.05-50	Y=0.46659X+0.02538	0.9998	0.02	0.05	83.5	108.5	100.1	1.74	7.28
BPAF	0.05-50	Y=0.12337X+0.01175	0.9992	0.02	0.05	99.5	101.2	99.1	4.24	7.60
BPAP	0.10-50	Y=0.04528X+0.00553	0.9991	0.03	0.10	99.2	99.4	95.3	1.76	9.77
3,3-DCBPA	0.20-50	Y=0.08545X+0.01279	0.9997	0.06	0.20	98.3	100.1	100.5	1.32	9.87
3,5-DCBPA	0.20-50	Y=0.12149X+0.01597	0.9999	0.06	0.20	99.7	100.2	101.5	1.09	7.88
BPFL	0.10-50	Y=0.53395X+0.03229	0.9994	0.03	0.10	102.1	100.2	103.3	0.86	5.31
BPZ	0.20-50	Y=0.12559X+0.01768	0.9996	0.06	0.20	99.9	100.2	99.2	2.27	6.87
TriCBPA	0.05-50	Y=0.68358X+0.09214	0.9994	0.02	0.05	89.9	99.1	100.2	1.77	6.22
BPTMC	0.20-50	Y=0.17473X+0.02196	0.9996	0.06	0.20	100.3	100.6	98.6	1.16	5.16
TBBPA	1.00-50	Y=0.02251X+0.00201	0.9992	0.33	1.00	100.5	99.1	114.9	9.79	16.3
DPS	0.20-50	Y=0.03380X+0.00671	0.9997	0.06	0.20	101.1	99.2	87.2	2.10	17.0
BPS-DAE	0.50-50	Y=0.02505X+0.00209	0.9995	0.15	0.50	99.7	102.2	99.2	2.29	7.72

Compound	Linear range/(μg/L)	Linear equation	r²	LOD/ (μg/kg)	LOQ/ (μg/kg)	Recoveries/%			Intra-day RSD/%	Inter-day RSD/%
Compound	Linear range/(μg/L)	Linear equation	r²	LOD/ (μg/kg)	LOQ/ (μg/kg)	LOQ	2LOQ	10LOQ	Intra-day RSD/%	Inter-day RSD/%
BPS	0.10-50	Y=0.09684X+0.08569	0.9999	0.03	0.10	109.6	92.3	100.9	2.12	5.41
2,4-BPS	0.25-50	Y=0.04661X+0.00363	0.9994	0.08	0.25	98.9	101.3	100.2	2.54	6.93
DHDPE	0.50-50	Y=0.01898X+0.00304	0.9992	0.15	0.50	98.5	101.4	100.1	5.45	8.24
BPF	2.50-50	Y=0.09588X+0.00842	0.9999	0.75	2.50	100.6	101.2	100.6	3.42	16.5
BPE	0.50-50	Y=0.06569X+0.01917	0.9999	0.15	0.50	101.9	100.1	102.5	4.17	6.68
BPT	0.10-50	Y=0.81667X+0.02810	0.9995	0.03	0.10	97.5	100.2	83.7	5.59	11.6
D-90(n=1)	2.50-50	Y=0.00212X+3.10855	0.9999	0.75	2.50	99.7	97.2	96.4	5.80	6.37
BPS-MAE	0.02-50	Y=0.76816X+0.02221	0.9995	0.01	0.02	105.1	97.8	101.4	1.44	7.13
BPA	0.50-50	Y=0.13014X+0.05599	0.9992	0.15	0.50	99.9	100.5	122.2	1.78	19.5
BPSIP	0.02-50	Y=0.71425X+0.06079	0.9995	0.02	0.05	103.5	99.8	100.4	3.67	5.79
TGSA	0.05-50	Y=1.03445X+0.12088	0.9998	0.02	0.05	101.2	102.9	100.3	2.16	11.5
TCBPA	0.05-50	Y=1.03451X+0.14530	0.9995	0.02	0.05	93.1	100.3	96.3	3.20	7.09
MCBPA	0.20-50	Y=0.14550X+0.01068	0.9991	0.06	0.20	99.2	99.9	100.4	2.33	7.35
PHBB	0.10-50	Y=0.08620X+0.01208	0.9994	0.03	0.10	100.1	100.3	97.9	3.58	7.12
BPS-MPE	0.05-50	Y=0.46659X+0.02538	0.9998	0.02	0.05	83.5	108.5	100.1	1.74	7.28
BPAF	0.05-50	Y=0.12337X+0.01175	0.9992	0.02	0.05	99.5	101.2	99.1	4.24	7.60
BPAP	0.10-50	Y=0.04528X+0.00553	0.9991	0.03	0.10	99.2	99.4	95.3	1.76	9.77
3,3-DCBPA	0.20-50	Y=0.08545X+0.01279	0.9997	0.06	0.20	98.3	100.1	100.5	1.32	9.87
3,5-DCBPA	0.20-50	Y=0.12149X+0.01597	0.9999	0.06	0.20	99.7	100.2	101.5	1.09	7.88
BPFL	0.10-50	Y=0.53395X+0.03229	0.9994	0.03	0.10	102.1	100.2	103.3	0.86	5.31
BPZ	0.20-50	Y=0.12559X+0.01768	0.9996	0.06	0.20	99.9	100.2	99.2	2.27	6.87
TriCBPA	0.05-50	Y=0.68358X+0.09214	0.9994	0.02	0.05	89.9	99.1	100.2	1.77	6.22
BPTMC	0.20-50	Y=0.17473X+0.02196	0.9996	0.06	0.20	100.3	100.6	98.6	1.16	5.16
TBBPA	1.00-50	Y=0.02251X+0.00201	0.9992	0.33	1.00	100.5	99.1	114.9	9.79	16.3
DPS	0.20-50	Y=0.03380X+0.00671	0.9997	0.06	0.20	101.1	99.2	87.2	2.10	17.0
BPS-DAE	0.50-50	Y=0.02505X+0.00209	0.9995	0.15	0.50	99.7	102.2	99.2	2.29	7.72

Compound	DF/%	Median/ (μg/kg)	Minimum/ (μg/kg)	Maximum/ (μg/kg)	Compound	DF/%	Median/ (μg/kg)	Minimum/ (μg/kg)	Maximum/ (μg/kg)
BPS	100.0	11.57	0.92	206.66	2,4-BPS	72.7	0.45	<LOD	6.15
DHDPE	90.9	0.56	<LOD	1.48	BPF	100.0	82.35	32.78	287.88
BPT	9.1	0.13	<LOD	0.13	TBBPA	81.8	2.83	<LOD	27.10
BPS-MAE	45.5	0.83	<LOD	1.98	BPA	100.0	365.92	56.79	1851.80
BPSIP	100.0	0.32	0.08	27.47	TGSA	27.3	1.17	<LOD	2.18
MCBPA	63.6	1.09	<LOD	1.97	PHBB	90.9	0.73	<LOD	3.76
BPS-MPE	63.6	0.20	<LOD	67.75	BPAF	54.6	1.28	<LOD	2.82
DPS	100.0	4.50	2.25	77.22