Chinese Journal of Chromatography ›› 2021, Vol. 39 ›› Issue (8): 835-844.DOI: 10.3724/SP.J.1123.2021.02035
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LIU Hongyuan1,2, JIN Jing1,*(
), GUO Cuicui1,3, CHEN Jiping1,*(
), HU Chun2
Received:2021-03-18
Online:2021-08-08
Published:2021-06-29
Contact:
JIN Jing,CHEN Jiping
Supported by:CLC Number:
LIU Hongyuan, JIN Jing, GUO Cuicui, CHEN Jiping, HU Chun. Advances in solid-phase extraction for bisphenols in environmental samples[J]. Chinese Journal of Chromatography, 2021, 39(8): 835-844.
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URL: https://www.chrom-china.com/EN/10.3724/SP.J.1123.2021.02035
| Chemical | CAS No. | IUPAC name | Formula | Mr | log Kow | pKa |
|---|---|---|---|---|---|---|
| BPA | 80-05-7 | 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol | C15H16O2 | 228.29 | 3.32 | 9.60 |
| BPB | 77-40-7 | 4-[2-(4-hydroxyphenyl)butan-2-yl]phenol | C16H18O2 | 242.31 | 4.13 | 10.10 |
| BPC | 79-97-0 | 4-[2-(4-hydroxy-3-methylphenyl)propan-2-yl]-2-methylphenol | C17H20O2 | 256.35 | 4.74 | 9.86 |
| BPS | 80-09-1 | 4-(4-hydroxyphenyl)sulfonylphenol | C12H10O4S | 250.27 | 1.65 | 8.20 |
| BPAF | 1478-61-1 | 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxyphenyl)propan-2-yl]phenol | C15H10F6O2 | 336.23 | 4.47 | 9.20 |
| BPF | 620-92-8 | 4-[(4-hydroxyphenyl)methyl]phenol | C13H12O2 | 200.23 | 2.91 | 7.55-10.80 |
| BPE | 2081-08-5 | 4-[1-(4-hydroxyphenyl)ethyl]phenol | C14H14O2 | 214.25 | 3.19 | 10.10 |
| TBBPA | 79-94-7 | 2,6-dibromo-4-[2-(3,5-dibromo-4-hydroxyphenyl)propan-2-yl]phenol | C15H12Br4O2 | 543.87 | 7.20 | 8.50 |
| BPAP | 1571-75-1 | 4-[1-(4-hydroxyphenyl)-1-phenylethyl]phenol | C20H18O2 | 290.35 | 4.86 | 10.22 |
| BPZ | 843-55-0 | 4-[1-(4-hydroxyphenyl)cyclohexyl]phenol | C18H20O2 | 268.35 | 5.00 | 9.76-10.37 |
Table 1 Physicochemical properties of typical bisphenols[14]
| Chemical | CAS No. | IUPAC name | Formula | Mr | log Kow | pKa |
|---|---|---|---|---|---|---|
| BPA | 80-05-7 | 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol | C15H16O2 | 228.29 | 3.32 | 9.60 |
| BPB | 77-40-7 | 4-[2-(4-hydroxyphenyl)butan-2-yl]phenol | C16H18O2 | 242.31 | 4.13 | 10.10 |
| BPC | 79-97-0 | 4-[2-(4-hydroxy-3-methylphenyl)propan-2-yl]-2-methylphenol | C17H20O2 | 256.35 | 4.74 | 9.86 |
| BPS | 80-09-1 | 4-(4-hydroxyphenyl)sulfonylphenol | C12H10O4S | 250.27 | 1.65 | 8.20 |
| BPAF | 1478-61-1 | 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxyphenyl)propan-2-yl]phenol | C15H10F6O2 | 336.23 | 4.47 | 9.20 |
| BPF | 620-92-8 | 4-[(4-hydroxyphenyl)methyl]phenol | C13H12O2 | 200.23 | 2.91 | 7.55-10.80 |
| BPE | 2081-08-5 | 4-[1-(4-hydroxyphenyl)ethyl]phenol | C14H14O2 | 214.25 | 3.19 | 10.10 |
| TBBPA | 79-94-7 | 2,6-dibromo-4-[2-(3,5-dibromo-4-hydroxyphenyl)propan-2-yl]phenol | C15H12Br4O2 | 543.87 | 7.20 | 8.50 |
| BPAP | 1571-75-1 | 4-[1-(4-hydroxyphenyl)-1-phenylethyl]phenol | C20H18O2 | 290.35 | 4.86 | 10.22 |
| BPZ | 843-55-0 | 4-[1-(4-hydroxyphenyl)cyclohexyl]phenol | C18H20O2 | 268.35 | 5.00 | 9.76-10.37 |
| Sorbent | Analytes | Samples | Measurement | Recoveries/% | Ref. |
|---|---|---|---|---|---|
| MI-SBA-15 | BPA | tap/well/waste water | HPLC | 87.00-110.2 | [27] |
| MI-SMS | BPA, BPF, BPB, BPE, BPAF | sediment | HPLC-DAD | 75.50-105.5 | [28] |
| COF-GO | BPA | river/sea water | CFDI-MS | 95.30-106.6 | [29] |
| COOH-MWCNT | TBBPA, BPA | lake/sea water | LC-MS | 82.00-99.00 | [30] |
| HPCSs | BPS, BPF, BPA, BPC, TBBPA, BPAP, BPAF, TCBPA | river water | HPLC-DAD | 89.60-111.5 | [31] |
| MOF/CS/PEO foam | BPA, BPB, BPC, BPAF, BPF | tap water | HPLC | 72.68-104.6 | [32] |
| Zr(Ⅳ)-MOF | BPA, BPB, BPAF, BPFL, BPS, BPF | tap water | LC-MS/MS | - | [33] |
| MP-CDP | BPA, BPF, BPAF | drinking water | HPLC | 92.90-107.0 | [35] |
Table 2 Application of new sorbents to solid-phase extraction for high-efficiency enrichment of bisphenols in environmental samples
| Sorbent | Analytes | Samples | Measurement | Recoveries/% | Ref. |
|---|---|---|---|---|---|
| MI-SBA-15 | BPA | tap/well/waste water | HPLC | 87.00-110.2 | [27] |
| MI-SMS | BPA, BPF, BPB, BPE, BPAF | sediment | HPLC-DAD | 75.50-105.5 | [28] |
| COF-GO | BPA | river/sea water | CFDI-MS | 95.30-106.6 | [29] |
| COOH-MWCNT | TBBPA, BPA | lake/sea water | LC-MS | 82.00-99.00 | [30] |
| HPCSs | BPS, BPF, BPA, BPC, TBBPA, BPAP, BPAF, TCBPA | river water | HPLC-DAD | 89.60-111.5 | [31] |
| MOF/CS/PEO foam | BPA, BPB, BPC, BPAF, BPF | tap water | HPLC | 72.68-104.6 | [32] |
| Zr(Ⅳ)-MOF | BPA, BPB, BPAF, BPFL, BPS, BPF | tap water | LC-MS/MS | - | [33] |
| MP-CDP | BPA, BPF, BPAF | drinking water | HPLC | 92.90-107.0 | [35] |
| Sorbent | Analytes | Samples | Measurement | Recoveries/% | Ref. |
|---|---|---|---|---|---|
| Alternative template MIP | BPA, BPB, BPAF, BPAP, BPS, | river/tap water | HPLC | 89.40-102.0 | [49] |
| BPF, BPE, BPZ | |||||
| Thermosensitive MIP | BPA | seawater | HPLC | 94.83-98.47 | [41] |
| Alternative template MIP | BPA, BPB, BPAF, BPAP, BPS, | sewage, sludge | HPLC | 82.20-101.0 (sewage), | [48] |
| BPF, BPE, BPZ, TBBPA | 43.60-96.70 (sludge) | ||||
| MGO@mSiO2@MIP | BPA | water | HPLC | 81.54-106.7 | [44] |
| Alternative template MIP | BPA | water | HPLC | 65.56-88.84 | [40] |
| IL-MIP | BPA | lake water | UV-vis | 93.67-102.1 | [43] |
| sol-gel MIP | BPA | river water | HPLC | 93.40±0.90 | [42] |
| Dual template MIP | BPA | river water | HPLC | 87.00-120.0 | [45] |
Table 3 Application of molecularly imprinted solid phase extraction technology to selective preconcentration or cleanup of bisphenols
| Sorbent | Analytes | Samples | Measurement | Recoveries/% | Ref. |
|---|---|---|---|---|---|
| Alternative template MIP | BPA, BPB, BPAF, BPAP, BPS, | river/tap water | HPLC | 89.40-102.0 | [49] |
| BPF, BPE, BPZ | |||||
| Thermosensitive MIP | BPA | seawater | HPLC | 94.83-98.47 | [41] |
| Alternative template MIP | BPA, BPB, BPAF, BPAP, BPS, | sewage, sludge | HPLC | 82.20-101.0 (sewage), | [48] |
| BPF, BPE, BPZ, TBBPA | 43.60-96.70 (sludge) | ||||
| MGO@mSiO2@MIP | BPA | water | HPLC | 81.54-106.7 | [44] |
| Alternative template MIP | BPA | water | HPLC | 65.56-88.84 | [40] |
| IL-MIP | BPA | lake water | UV-vis | 93.67-102.1 | [43] |
| sol-gel MIP | BPA | river water | HPLC | 93.40±0.90 | [42] |
| Dual template MIP | BPA | river water | HPLC | 87.00-120.0 | [45] |
| Procedure | Analytes | Samples | Measurement | Recoveries/% | Ref. |
|---|---|---|---|---|---|
| Extraction: 10 mL ACN, 4 g MgSO4+1 g NaCl | BPA | fish | HPLC-MS/MS | 80.80-118.6 | [53] |
| Clean-up: 25 mg PSA+25 mg C18+2% NaCl | |||||
| Extraction: 10 mL ACN (1% HCl), 4 g MgSO4+1 g NaCl | BPA, | fish | LC-MS/MS | 67.00-107.0 | [54] |
| Clean-up: 500 mg C18+500 mg PSA+1500 mg MgSO4 | TBBPA | ||||
| Extraction: 10 mL ACN(1% acetic acid), 4 g MgSO4+1 g NaCl | BPA | sludge | LC-MS/MS | 87.00-101.0 | [55] |
| Clean-up: 150 mg MgSO4+50 mg Chitin | |||||
| Extraction: 10 mL ACN (0.1% acetic acid)+5 mL water, 1 g MgSO4+1 g NaCl | EDCs | sediment | GC-MS/MS | 60.00-130.0 | [56] |
| Clean-up: C18+PSA | (BPA) | ||||
| Extraction: 4 mL ACN+2 mL saturated NaCl solution | TBBPA | aquatic | UPLC-MS/MS | 74.00-121.0 | [57] |
| Clean-up: 50 mg MgSO4+50 mg C18 | products |
Table 4 Application of QuEChERS to pretreatment of bisphenols
| Procedure | Analytes | Samples | Measurement | Recoveries/% | Ref. |
|---|---|---|---|---|---|
| Extraction: 10 mL ACN, 4 g MgSO4+1 g NaCl | BPA | fish | HPLC-MS/MS | 80.80-118.6 | [53] |
| Clean-up: 25 mg PSA+25 mg C18+2% NaCl | |||||
| Extraction: 10 mL ACN (1% HCl), 4 g MgSO4+1 g NaCl | BPA, | fish | LC-MS/MS | 67.00-107.0 | [54] |
| Clean-up: 500 mg C18+500 mg PSA+1500 mg MgSO4 | TBBPA | ||||
| Extraction: 10 mL ACN(1% acetic acid), 4 g MgSO4+1 g NaCl | BPA | sludge | LC-MS/MS | 87.00-101.0 | [55] |
| Clean-up: 150 mg MgSO4+50 mg Chitin | |||||
| Extraction: 10 mL ACN (0.1% acetic acid)+5 mL water, 1 g MgSO4+1 g NaCl | EDCs | sediment | GC-MS/MS | 60.00-130.0 | [56] |
| Clean-up: C18+PSA | (BPA) | ||||
| Extraction: 4 mL ACN+2 mL saturated NaCl solution | TBBPA | aquatic | UPLC-MS/MS | 74.00-121.0 | [57] |
| Clean-up: 50 mg MgSO4+50 mg C18 | products |
| Sorbent | Analytes | Samples | Measurement | Recoveries/% | Ref. |
|---|---|---|---|---|---|
| Fe3O4@PDA | BPF, BPA, BPB, BPAP | tap/pond water | HPLC | 92.00-105.0 | [68] |
| C-NH2@Fe3O4 | BPA, BPAF, TBBPA | tap/slush/waste water | HPLC-MS/MS | 86.10-110.0 | [67] |
| Fe3O4/GO | BPA | waste water | HPLC | 77.60-89.60 | [69] |
| Fe3O4-OA/CQDs | BPA, BPAF, TBBPA | lake/waste water | FTIR | 94.50-101.3 | [66] |
| CMMPs | BPA, BPB, BPAF, BPF | tap/river water | UHPLC | 85.40-104.0 | [65] |
| HDTMA-ZSM-5/Fe2O3 | BPA, BPAP, BPAF, BPP | tap/river/waste water | HPLC | 83.00-108.0 | [64] |
| MCGC | BPA, BPF | waste water | HPLC-FLD | 90.20-97.70 | [71] |
| MGO-DDA | BPA | lake/waste water | HPLC | 74.90-93.10 | [72] |
Table 5 Application of magnetic solid phase extraction to pretreatment of bisphenols in water
| Sorbent | Analytes | Samples | Measurement | Recoveries/% | Ref. |
|---|---|---|---|---|---|
| Fe3O4@PDA | BPF, BPA, BPB, BPAP | tap/pond water | HPLC | 92.00-105.0 | [68] |
| C-NH2@Fe3O4 | BPA, BPAF, TBBPA | tap/slush/waste water | HPLC-MS/MS | 86.10-110.0 | [67] |
| Fe3O4/GO | BPA | waste water | HPLC | 77.60-89.60 | [69] |
| Fe3O4-OA/CQDs | BPA, BPAF, TBBPA | lake/waste water | FTIR | 94.50-101.3 | [66] |
| CMMPs | BPA, BPB, BPAF, BPF | tap/river water | UHPLC | 85.40-104.0 | [65] |
| HDTMA-ZSM-5/Fe2O3 | BPA, BPAP, BPAF, BPP | tap/river/waste water | HPLC | 83.00-108.0 | [64] |
| MCGC | BPA, BPF | waste water | HPLC-FLD | 90.20-97.70 | [71] |
| MGO-DDA | BPA | lake/waste water | HPLC | 74.90-93.10 | [72] |
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