Supporting Information s73

Supporting information

Table S1.

List of 37 suspected transformation products of BPA selected from literature including the proposed molecular structures, the applied degradation method, analytical method employed and the relative references.

Compound / Proposed structure / Molecular formula / Accurate molecular mass / [M-H]-
(m/z) / Degradation
method / Analytical method / Reference
Bisphenol A / / C15H16O2 / 228.1150 / 227.1077
1 / / C15H16O5 / 276.0998 / 275.0925 / Photo- Fenton-like / GC-MS / [1]
Ozonation / LC-MS
RP-HPLC / [2,3]
2 / / C15H16O4 / 260.1049 / 259.0976 / Electrochemically generated Fenton’s reagent (EF) / LC-MS / [4]
3 / / C15H16O4 / 260.1049 / 259.0976 / Photodegradation / RP-HPLC
LC-MS / [5]
4
(TP1) / / C15H16O3 / 244.1099 / 243.1027 / EF / RP-HPLC
LC-MS
GC-MS / [4]
Ozonation / LC-MS
RP-HPLC / [3]
Photodegradation / RP-HPLC
LC-MS / [5]
5
(TP1) / / C15H16O3 / 244.1099 / 243.1027 / EF / RP-HPLC
LC-MS
GC-MS / [4]
Electrochemical / RP-HPLC / [6]
6 / / C15H14O3 / 242.0943 / 241.0870 / Ozonation / LC-MS
RP-HPLC / [2][3]
Photodegradation / RP-HPLC
LC-MS / [5]
7 / / C13H14O4 / 234.0892 / 233.0819 / Ozonation / LC-MS
RP-HPLC / [3]
Photo- Fenton-like / GC-MS / [1]
8 / / C13H10O3 / 214.0630 / 213.0557 / Photo- Fenton-like / GC-MS / [1]
9 / / C14H18O / 202.1358 / 201.1285 / Photo- Fenton-like / GC-MS / [1]
10 / / C12H14O2 / 190.0994 / 189.0921 / Ozonation / LC-MS
RP-HPLC / [2]
11 / / C9H10O4 / 182.0579 / 181.0506 / Photodegradation / RP-HPLC
LC-MS / [5]
12 / / C9H12O3 / 168.0786 / 167.0714 / Photodegradation / RP-HPLC
LC-MS / [5]
13
(TP3) / / C8H8O4 / 168.0423 / 167.0350 / EF / RP-HPLC
LC-MS
GC-MS / [4]
14 / / C8H18O3 / 162.1256 / 161.1183 / Photo- Fenton-like / GC-MS / [1]
15 / / C9H12O2 / 152.0837 / 151.0764 / Ozonation / LC-MS
RP-HPLC / [2,3]
Photo-Fenton / GC-MS / [7]
Electrocatalytic
Ti-PbO2-ionic liquids / LC-MS / [8]
16 / / C9H12O2 / 152.0837 / 151.0764 / Electrochemical / RP-HPLC / [6]
17 / / C9H10O2 / 150.0681 / 149.0608 / Photo- Fenton-like / GC-MS / [1]
18 / / C9H12O / 136.0888 / 135.0815 / Electrochemical / RP-HPLC / [6]
Photo-Fenton / GC-MS / [7]
Electrocatalytic
Ti-PbO2-ionic liquids / LC-MS / [8]
19 / / C9H10O / 134.0732 / 133.0659 / EF / RP-HPLC
LC-MS
GC-MS / [4]
Photo-Fenton / GC-MS / [7]
Electrochemical / RP-HPLC / [6]
20 / / C4H6O6 / 150.0164 / 149.0092 / Electrochemical / RP-HPLC / [6]
21
(TP5) / / C7H8O3 / 140.0473 / 139.0401 / Photo- Fenton-like / GC-MS / [1]
22 / / C7H6O3 / 138.0317 / 137.0244 / EF / RP-HPLC
LC-MS
GC-MS / [4]
Ozonation / LC-MS
RP-HPLC / [2]
23 / / C8H8O2 / 136.0524 / 135.0451 / Photo-Fenton / GC-MS / [7]
Photo- Fenton-like / GC-MS / [1]
24 / / C9H10O / 134.0732 / 133.0659 / Electrocatalytic
Ti-PbO2-ionic liquids / LC-MS / [8]
Photo-Fenton / GC-MS / [7]
25 / / C9H10O / 134.0732 / 133.0659 / Photo-Fenton / GC-MS / [7]
26 / / C7H14O2 / 130.0994 / 129.0921 / Photo- Fenton-like / GC-MS / [1]
27 / / C6H6O3 / 126.0317 / 125.0244 / Electrochemical / RP-HPLC / [6]
Ozonation / LC-MS
RP-HPLC / [2]
28
(TP6) / / C4H4O4 / 116.0110 / 115.0037 / EF / RP-HPLC
LC-MS
GC-MS / [4]
/ Electrochemical / RP-HPLC / [6]
29 / / C6H6O2 / 110.0368 / 109.0295 / Photo- Fenton-like / GC-MS / [1]
EF / RP-HPLC
LC-MS
GC-MS / [4]
Electrochemical / RP-HPLC / [6]
Ozonation / LC-MS
RP-HPLC / [3]
Ozonation / LC-MS
RP-HPLC / [2]
Photo-Fenton / GC-MS / [7]
30 / / C6H4O2 / 108.0211 / 107.0138 / EF / RP-HPLC
LC-MS
GC-MS / [4]
Ozonation / LC-MS
RP-HPLC / [3]
Electrochemical / RP-HPLC / [6]
Photo-Fenton / GC-MS / [7]
Electrocatalytic
Ti-PbO2-ionic liquids / LC-MS / [8]
31 / / C6H6O / 94.0419 / 93.0346 / EF / RP-HPLC
LC-MS
GC-MS / [4]
Photo-Fenton / GC-MS / [7]
Electrocatalytic
Ti-PbO2-ionic liquids / LC-MS / [8]
32 / / C5H6O2 / 98.0368 / 97.0295 / Electrocatalytic
Ti-PbO2-ionic liquids / LC-MS / [8]
33 / / C4H4O3 / 100.0160 / 99.0088 / EF / RP-HPLC
LC-MS
GC-MS / [4]
34 / / C3H4O4 / 104.0110 / 103.0037 / Ozonation / LC-MS
RP-HPLC / [2]
35 / / C2H2O4 / 89.9953 / 88.9880 / Ozonation / LC-MS
RP-HPLC / [2]
36 / / C2H4O2 / 60.0211 / 59.0138 / EF / RP-HPLC
LC-MS
GC-MS / [4]
Electrochemical / RP-HPLC / [6]
37 / / CH2O2 / 46.0055 / 44.9982 / EF / RP-HPLC
LC-MS
GC-MS / [4]

References

1. Molkenthin, M.; Olmez-Hanci, T.; Jekel, M.R.; Arslan-Alaton, I. Photo-Fenton-like treatment of BPA: effect of UV light source and water matrix on toxicity and transformation products. Water Res. 2013, 47, 5052–5064.

2. Kusvuran, E.; Yildirim, D. Degradation of bisphenol A by ozonation and determination of degradation intermediates by gas chromatography–mass spectrometry and liquid chromatography–mass spectrometry. Chemical Engineering Journal 2013, 220, 6–14.

3. Deborde, M.; Rabouan, S.; Mazellier, P.; Duguet, J.-P.; Legube, B. Oxidation of bisphenol A by ozone in aqueous solution. Water Res. 2008, 42, 4299–4308.

4. Gözmen, B.; Oturan, M.A.; Oturan, N.; Erbatur, O. Indirect Electrochemical Treatment of Bisphenol A in Water via Electrochemically Generated Fenton's Reagent. Environ. Sci. Technol. 2003, 37, 3716–3723.

5. da Silva, Júlio César Cardoso; Reis Teodoro, Janaina Aparecida; Afonso, Robson José de Cássia Franco; Aquino, S.F.; Augusti, R. Photodegradation of bisphenol A in aqueous medium: monitoring and identification of by-products by liquid chromatography coupled to high-resolution mass spectrometry. Rapid Commun. Mass Spectrom. 2014, 28, 987–994.

6. Cui, Y.-h.; Li, X.-y.; Chen, G. Electrochemical degradation of bisphenol A on different anodes. Water Res. 2009, 43, 1968–1976.

7. Katsumata, H.; Kawabe, S.; Kaneco, S.; Suzuki, T.; Ohta, K. Degradation of bisphenol A in water by the photo-Fenton reaction. Journal of Photochemistry and Photobiology A: Chemistry 2004, 162, 297–305.

8. Ju, P.; Fan, H.; Guo, D.; Meng, X.; Xu, M.; Ai, S. Electrocatalytic degradation of bisphenol A in water on a Ti-based PbO2–ionic liquids (ILs) electrode. Chemical Engineering Journal 2012, 179, 99–106.