Supporting Information. Treatment of Aqueous Film-Forming Foam by Heat-Activated. Persulfate Under Conditions Representative of
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1 1 Supporting Information Treatment of Aqueous Film-Forming Foam by Heat-Activated Persulfate Under Conditions Representative of In Situ Chemical Oxidation Thomas A. Bruton and David L. Sedlak* Department of Civil and Environmental Engineering University of California at Berkeley 12 Berkeley, CA USA * Corresponding author, sedlak@berkeley.edu S-1
2 Table of Contents Text S1: Analysis of sulfate radical fate. Table S1: Full names, abbreviations, and molecular formulae for PFAS analytes measured in this study. Table S2: Physico-chemical properties of aquifer sediment. Table S3: Internal standard, monitored ion transitions, and MS conditions used for quantification of each analyte. Table S4: Pseudo-first order rate constants for persulfate disappearance. Figure S1: Chemical structure of (a) perfluorohexane sulfonamido amine (PFHxSAm) and (b) perfluorohexane sulfonamide amino carboxylate (PFHxSAmA). Figure S2: Persulfate decomposition kinetics in experiments with (a) AFFF and (b) PFOA and DGBE. Figure S3: Total organic carbon concentration during heat-activated persulfate treatment of Ansul and 3M AFFF in water or aquifer sediment slurry. Figure S4: Modeled pseudo-first order reaction rate constant for persulfate decomposition in homogeneous solution as a function of ph. Figure S5: Analysis of SO - 4 fate in systems with different ph under conditions encountered at the start of the reactions. Figure S6: Analysis of SO - 4 fate at ph 3 with different assumed rate constants for the reaction of SO - 4 with 6:2 FtTAoS under conditions encountered at the start of the reactions. Figure S7: Total organic carbon concentration during heat-activated persulfate treatment of PFOA in water with varying initial concentrations of DGBE. Figure S8: Heat-activated persulfate treatment of PFOA in the presence of varying concentrations of methanol. Figure S9: Heat-activated persulfate treatment of PFOA in the presence of varying concentrations of ethanol. Figure S10: PFOA loss in persulfate-free controls. S-2
3 Text S1. Analysis of sulfate radical fate. Under the conditions employed in this study, sulfate radical generated from thermolysis of persulfate can undergo several reactions: SO +OH HO +SO =8.3 x 10 M s (1) SO +H O HO +HSO =1.8 x 10 M s (2) SO +S O S O +SO =1.8 x 10 M s (3) SO +6:2 FtTAoS products+so =2.6 x 10 M s (4) The fraction of SO 4 - reacting by each pathway can be calculated as follows: k A f = k OH +k H O +k S O +k PFOA where f A is the fraction of SO - 4 reacting with species A, k A is the second order rate constant for the reaction of SO - 4 and A, and A is OH -, H 2 O, S 2 O 2-8, or 6:2 FtTAoS. This equation was used to calculate the fraction of sulfate radicals reacting with each reactant under different conditions of ph (Figure S5). Since the rate constant for the reaction of sulfate radical and 6:2 FtTAoS has not been measured, the calculations were repeated over a range of values for k 4 at a fixed ph of 3 (Figure S6) S-3
4 Name Abbreviation Molecular Formula Perfluorocarboxylates Perfluorobutyrate PFBA C 3 F 7 COO - Perfluoropentanoate PFPeA C 4 F 9 COO - Perfluorohexanoate PFHxA C 5 F 11 COO - Perfluoroheptanoate PFHpA C 6 F 13 COO - Perfluorooctanoate PFOA C 7 F 15 COO - Perfluorobutane sulfonate Perfluorohexane sulfonate Perfluoroheptane sulfonate Perfluorooctane sulfonate 6:2 Fluorotelomer thioamido sulfonate 6:2 Fluorotelomer sulfonate Perfluorosulfonates PFBS C 4 F 9 SO 3 - PFHxS C 6 F 13 SO 3 - PFHpS C 7 F 15 SO 3 - PFOS C 8 F 17 SO 3 - Fluorotelomer-based compounds 6:2 FtTAoS C 6 F 13 (CH 2 ) 2 S(CH 2 ) 2 CONHC(CH 3 ) 2 CH 2 SO 3-6:2 FtS C 6 F 13 (CH 2 ) 2 SO 3 - Table S1. Full names, abbreviations, and molecular formulae for PFAS analytes measured in this study. 88 S-4
5 Sand (wt. %) Silt (wt. %) Clay (wt. %) ph BET surface area (m 2 /g) Total Fe (mg/kg) Total Mn (mg/kg) Fe-CBD (mg/kg) Mn- CBD (mg/kg) , , Table S2. Physico-chemical properties of aquifer sediment. Surface area was measured at the University of California, Berkeley 3. All other properties were determined by the Analytical Laboratory at the University of California, Davis. Details on the analytical protocols are available at Fe-CBD and Mn-CBD are the concentrations of Fe and Mn remaining in the sediments after treatment with a citrate-bicarbonate-dithionite extraction as described previously 1. The CBD extraction procedure is designed to remove free Fe and Mn oxides, leaving only structural Fe and Mn. TC (%) S-5
6 Compound Internal Molecular Fragmentor Quant. Collision Qual. Collision Polarity Standard Ion Voltage Ion Energy Ion Energy (V) (m/z) (V) (m/z) (V) Perfluorocarboxylates PFBA [ 13 C 4 ] PFBA (-) PFPeA [ 13 C 3 ] PFPeA (-) PFHxA [ 13 C 2 ] PFHxA (-) PFHpA [ 13 C 2 ] PFHxA (-) PFOA [ 13 C 4 ] PFOA (-) Perfluorosulfonates PFBS [ 18 O 2 ] PFHxS (-) PFHxS [ 18 O 2 ] PFHxS (-) PFHpS [ 13 C 4 ] PFOS (-) PFOS [ 13 C 4 ] PFOS (-) Fluorotelomer-based compounds 6:2 FtTAoS [ 13 C 2 ] 6:2 FtS (-) 6:2 FtS [ 13 C 2 ] 6:2 FtS Internal Standards [ 13 C 4 ] PFBA (-) [ 13 C 3 ] PFPeA (-) [ 13 C 2 ] PFHxA (-) [ 13 C 4 ] PFOA (-) [ 18 O 2 ] PFHxS (-) [ 13 C 4 ] PFOS (-) [ 13 C 2 ] 6:2 FtS (-) Table S3. Internal standard, monitored ion transitions, and MS conditions used for quantification of each analyte. 103 S-6
7 Experiment Observed pseudo-1 st order rate constant for persulfate st Aliquot S 2 O 8 2- Ansul ultrapure water 1.21 x 10-4 ± 0.02 x M ultrapure water 1.4 x 10-4 ± 0.02 x nd Aliquot S 2 O 8 2- Ansul sediment 1.4 x 10-4 ± 0.02 x x 10-4 ± 0.04 x M sediment 1.5 x 10-4 ± 0.02 x x 10-4 ± 0.04 x 10-4 PFOA + 0 mm DGBE 2.3 x 10-4 ± 0.02 x 10-4 PFOA + 5 mm DGBE 1.4 x 10-4 ± 0.06 x 10-4 PFOA + 10 mm DGBE 1.7 x 10-4 ± 0.1 x 10-4 PFOA + 50 mm DGBE 1.8 x 10-4 ± 0.2 x 10-4 PFOA mm DGBE 2.9 x 10-4 ± 0.2 x 10-4 PFOA mm DGBE 5.5 x 10-4 ± 0.5 x 10-4 Table S4. Pseudo-first order rate constants for persulfate disappearance. 106 S-7
8 Figure S1. Chemical structure of (a) perfluorohexane sulfonamido amine (PFHxSAm) and (b) perfluorohexane sulfonamide amino carboxylate (PFHxSAmA). S-8
9 Figure S2. Persulfate decomposition kinetics in experiments with (a) AFFF and (b) PFOA and DGBE. Ansul and 3M are experiments in water. Ansul Sed. 1, Ansul Sed. 2, 3M Sed. 1 and 3M Sed. 2 are experiments with two sequential doses of persulfate added to aquifer sediment slurries. [S 2 O 2-8 ] 0 = 50 mm; 21,000-fold dilution of S-9
10 Ansul AFFF; 83,000-fold dilution of 3M AFFF; [PFOA] 0 = 0.5 µm; T = 85 o C. Error bars represent the standard deviation of triplicate measurements. 119 S-10
11 Figure S3. Total organic carbon concentration during heat-activated persulfate treatment of Ansul and 3M AFFF in water or aquifer sediment slurry. [S 2 O 2-8 ] 0 = 50 mm, 21,000- fold dilution of Ansul AFFF, 83,000-fold dilution of 3M AFFF, T = 85 o C. Error bars represent the standard deviation of triplicate measurements. 125 S-11
12 Figure S4. Modeled pseudo-first order reaction rate constant for persulfate decomposition in homogeneous solution as a function of ph. 129 S-12
13 Figure S5. Analysis of SO - 4 fate in systems with different ph under conditions encountered at the start of the reactions. [6:2FtTAoS] = 1.0 µm, [S 2 O 2-8 ] = 50 mm. f A is the fraction of SO - 4 reacting with a given species, A, where A is OH -, DGBE, S 2 O 2-8, H 2 O, or 6:2 FtTAoS. 135 S-13
14 Figure S6. Analysis of SO - 4 fate at ph 3 with different assumed rate constants for the reaction of SO - 4 with 6:2 FtTAoS under conditions encountered at the start of the reactions. [6:2 FtTAoS] = 1.0 µm, [S 2 O ] = 50 mm. f A is the fraction of SO 4 reacting with a given species, A, where A is OH -, DGBE, S 2 O 2-8, H 2 O, or 6:2 FtTAoS. 141 S-14
15 Figure S7. Total organic carbon concentration during heat-activated persulfate treatment of PFOA in water with varying initial concentrations of DGBE. [S 2 O 2-8 ] 0 = 50 mm, [PFOA] 0 = 0.5 µm, T = 85 o C. Error bars represent the standard deviation of triplicate measurements. 147 S-15
16 Figure S8. Heat-activated persulfate treatment of PFOA in the presence of varying concentrations of methanol. (a) PFOA; (b) PFCAs after 7.5 hours. [S 2 O 8 2- ] 0 = 50 mm, T = 85 o C. All data points represent a single measurement. S-16
17 Figure S9. Heat-activated persulfate treatment of PFOA in the presence of varying concentrations of ethanol. (a) PFOA; (b) PFCAs after 7.5 hours. [S 2 O 8 2- ] 0 = 50 mm, T = 85 o C. All data points represent a single measurement. S-17
18 Figure S10. PFOA loss in persulfate-free controls. [PFOA] 0 = 0.5 µm, T = 85 o C. All data points represent a single measurement. 161 S-18
19 REFERENCES 1. Neta, P.; Huie, R. E.; Ross, A. B., Rate constants for reactions of inorganic radicals in aqueous solution. American Chemical Society: Qian, Y.; Guo, X.; Zhang, Y.; Peng, Y.; Sun, P.; Huang, C.-H.; Niu, J.; Zhou, X.; Crittenden, J. C., Perfluorooctanoic Acid Degradation Using UV Persulfate Process: Modeling of the Degradation and Chlorate Formation. Environmental science & technology 2015, 50 (2), Pham, A. L. T.; Doyle, F. M.; Sedlak, D. L. Kinetics and efficiency of H 2 O 2 activation by iron-containing minerals and aquifer materials. Wat. Res. 2012, 46 (19), S-19
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