Advanced Oxidation Technologies: History
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Zhendong Li
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Yanmei Sun
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Dongfang Liu
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Malan Yi
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Fang Chang
,
Huiting Li
,
Yunyi Du

Advanced oxidation process (AOPs) based on sulfate radical (SO4●−) and singlet oxygen (1O2) has attracted a lot of attention because of its characteristics of rapid reaction, efficient treatment, safety and stability, and easy operation. SO4●− and 1O2 mainly comes from the activation reaction of peroxymonosulfate (PMS) or persulfate (PS), which represent the oxidation reactions involving radicals and non-radicals, respectively. The degradation effects of target pollutants will be different due to the type of oxidant, reaction system, activation methods, operating conditions, and other factors.

  • sulfate radical
  • singlet oxygen
  • AOPS
  • peroxymonosulfate

1. Characteristics of Persulfate and Peroxymonosulfate

At present, the production of SO4●− mainly comes from the activation of PMS and PS, which are the monosubstituted or symmetrically substituted derivatives of hydrogen peroxide by sulfonic acid group (-SO3), respectively. PMS has been widely used in organic compound synthesis and as a chlorine-free additive for disinfecting swimming pools at a rate of about 1–2 pounds per 10,000 gallons of pool water [1]. Under the presence of 25 mg/L PMS and 0.1 mg/L Co2+, the removal rate of E. coli reached 99.99% after 1 h of reaction [2]. PMS is white solid powder. It is stable when pH is less than 6 or pH is 12. When pH is 9, it showed the poorest stability where half of HSO5− decomposes to SO52− [3]. At present, the widely used potassium bisulfate complex salt (2KHSO5·KHSO4·K2SO4) is composed of three components, potassium peroxymonosulfate, potassium hydrogen sulfate, and potassium sulphate, and its main active substance is potassium peroxymonosulfate (KHSO5). The salt is marketed under the trade names Caroat and Oxone registered by Evonik and DuPont, respectively. Oxone is a white granular powder crystal salt, which is stable, non-toxic, inexpensive, and soluble in water. The peroxide bond (O-O) distance is 1.453 Å, and the bond energy is 140–213.3 kJ/mol. PMS is most stable when the solution pH is less than 6 and equal to 12. When pH is 9, the stability is worst, and the concentration of HSO5− and SO52− in the solution is almost equal. When pH is less than 1, PMS will undergo hydrolysis reaction to produce H2O2 [4]. PS, an oxidant with symmetrical structure, was first known as the initiator of polymerization reaction. The O-O distance is 1.497 Å, and the bond energy is 140 kJ/mol [5]. PS, often in the form of potassium persulfate or sodium persulfate, has been widely used as bleaching agents, oxidants, emulsion polymerization promoters, and water or soil remediation agents. The related properties of PMS and PS are shown in Table 1. Both PMS and PS are strong oxidants, but their direct reaction rates with most pollutants are very low. Therefore, it is necessary to activate them through appropriate ways to destroy the O-O bond and generate strong oxidizing free radicals, 1O2 and other ROS to degrade organic pollutants quickly and efficiently.
Table 1. Properties of PMS and PS.
Properties PS (Take Potassium Persulfate as an Example) PMS (Take Potassium Peroxymonosulfate as an Example)
CAS Registry Number 7727-21-1 10058-23-8
Chemical formula K2S2O8 KHSO5
Molecular mass 270.309 614.738
Solubility in water (20 °C) 520 g/L >250 g/L
Redox potential 2.01 V 1.82 V
Because PS and PMS are solid powders, they can be transported and stored more easily. Compared with H2O2, the anions of PS and PMS remain stable in water for a much longer time until they are properly activated. In addition, PMS and PS-based AOPs can proceed smoothly in a wide solution pH range from acidic to alkaline (pH = 2–10), while H2O2-based Fenton process requires strict acidic conditions (pH = 2.7–3). Generally, PS and PMS can be activated with the assistance of ultraviolet light, heat, alkali, or metal catalysts, etc. Different types of oxidants and activation methods will produce different ROS. The advanced oxidation processes dominated by SO4●− and 1O2 were discussed in this research.
advanced oxidation process (AOPs) based on sulfate radical (SO4●−) and singlet oxygen (1O2) has attracted a lot of attention because of its characteristics of rapid reaction, efficient treatment, safety and stability, and easy operation. SO4●− and 1O2 mainly comes from the activation reaction of peroxymonosulfate (PMS) or persulfate (PS), which represent the oxidation reactions involving radicals and non-radicals, respectively. The degradation effects of target pollutants will be different due to the type of oxidant, reaction system, activation methods, operating conditions, and other factors.

2. Sulfate Radicals-Based Advanced Oxidation

Studies have shown that AOPs based on SO4●− and ●OH is an effective method for the degradation of refractory organic pollutants, such as pharmaceuticals, pesticides, personal care products, steroids, endocrine disruptors, etc. [6]. However, AOPs based on ●OH degrades organic pollutants through a non-selective, multi-step approach that typically requires an acidic environment. In addition, the oxidation process is severely limited by the large amount of dissolved organic matter and anions in complex environments, which are the main scavengers of ●OH. SO4●− is inherently more oxidizing than ●OH and lasts longer in aqueous solutions, and in some cases SO4●− can oxidize contaminants that ●OH cannot. In recent years, SO4●−-based AOPs have replaced ●OH-based AOPs to some extent.
The essence of the advanced oxidation process based on SO4●− is to activate PMS or PS to form SO4●− to achieve the removal of organic matter. Besides SO4●−, there are also associated or indirect generation of ●OH, superoxide radical (O2●−), or other radicals, but SO4●− plays a leading role in the degradation of pollutants. These free radicals (SO4●−, ●OH, and O2●−) could be detected by using 5,5-dimethyl-1-pyrroline-1- oxide (DMPO) as a spin trapping agent in an electron paramagnetic resonance spectroscopy (EPR) [7]. Both ethanol (Et) and tert-butanol (TBA) could quench ●OH rapidly (kEt = 1.2–2.8 × 109 M−1s−1, kTBA = 3.8–7.6 × 108 M−1s−1), and the reaction rate between Et and SO4●− is much faster than that of TBA (kEt = 1.6–7.7 × 107 M−1s−1, kTBA = 4.0–9.1 × 105 M−1s−1). Therefore, Et and TBA can be used as capture agents to identify who contributes more to the degradation of pollutants [8]. PMS and PS can be activated to produce SO4●− through energy input, transition metal ions and their oxides, non-metallic materials, etc. Studies on the degradation of pollutants by activating PMS and PS in different ways to generate SO4●− are summarized in Table 2.
Table 2. PMS and PS radical activation with various method for the removal of pollutants.
Reaction System Pollutant Conditions Reactivity Dominant ROS Ref.
UV(254 nm)/PMS benzoic acid (BA) [BA] = 9.90 μM; [PMS] = 100 μM as 1/2 Oxone;
pH = 11.		 >90% with 10 min SO4●− and ●OH [9]
UV(254 nm)/PS Chlorophene [Chlorophene] = 1 μM, [PS] = 50 μM, pH = 7, UV intensity (254 nm,15 W) = 4.23 mWcm−2. 100% with 5 min SO4●− [10]
UV-C laser/PS Iohexol (IOX) IUV = 25 mW/cm2, [PS] = 1.0 mM, [IOX] = 10 μM, initial pH = 7.0 ± 0.5, temperature 25 °C. 93.8% within only 40 s SO4●− [11]
Heat/PS Ibuprofen (IBU) [phosphate buffer] = 0.09 M, pH = 7.0, [IBU] = 20.36 μM, [PS] = 1.0 mM, T = 70 °C. 100% with 20 min SO4●− and ●OH [12]
Heat/PS 1-alkyl-3-methylimidazolium bromides (C4mimBr) [C4mimBr] = 0.1 mM, [PS] = 10 mM, T = 60 °C, pH = 7, V = 100 mL. 100% with 120 min SO4●− [13]
Ultrasound/PS 1,1,1-trichloroethane (TCA) [TCA] = 25.0 mg/L, [PS] = 250.0 mg/L pH 7.0, T = 20 ± 2 °C, ultrasound: 400 kHz, 100 W. 100% with 120 min SO4●− [14]
Electrolysis(boron-doped diamond anode)/PS Ampicillin [Ampicillin] = 1.1 mg/L, [PS] = 250 mg/L, current density (BDD anode) = 25 mAcm−2. 100% with 120 min SO4●− and ●OH [15]
Fe0/PS sulfamethoxazole (SMX) [SMX] = 39.5 μM, [PS] = 1.0 mM, [Fe0] = 2.23 mM; m (Fe0) = 2.5 mg, pH = 3.52. 100% with 30 min SO4●− [16]
Fe2+/PS Acetaminophen (ACT) [ACT] = 0.05 mM, [Fe2+] = 1 mM, [PS] = 0.8 mM, pH = 3, T = 20 °C. 70% with 30 min SO4●− [17]
Fe(II)/PMS 2-chlorobiphenyl (2-CB) [2-CB] = 0.0212 mM; [Fe(II)] = 0.11 mM; [PMS]0 = 0.11 mM. 90% with 240 min SO4●− [18]
Co2+/PMS nuclear grade cationic IRN-77 resin initial pH = 9, [Co2+] = 4 mM, [PMS] = 60 mM T = 60 °C. ∼90% COD removal (1000 mg/L) with 60 min SO4●− and ●OH [19]
Cu2+/PMS Triclosan (TCS) [TCS] = 9 mg/L (0.031 mM), initial pH = 7, molar ratio of oxidant to metal = 1:1, molar ratio of oxidant to triclosan = 5:1. 95% with 10 min SO4●− [20]
Ru3+/PMS 2,4-dichlorophenol (2,4-DCP) [2,4-DCP] = 0.311 mM, [RuCl3·xH2O] = 2.553 mM, [KHSO5] = 1.244 mM, pH = 7. 98% in less than 1 min SO4●− [21]
Natural chalcopyrite/PMS Bisphenol S Bisphenol S = 25 μM, chalcopyrite = 2 g/L, PMS = 0.4 mM, initial pH = 6.2, T = 303 K. 83% with 30 min SO4•− and •OH [22]
Eggshell-loaded CoFe2O4./PMS Florfenicol (FF) CoFe2O4/eggshell = 0.4 g/L, [PMS] = 0.96 mmol/L, [FF] = 10 mg/L, T = 30 °C, initial pH = 6.61. 96.8% within 40 min SO4•– and •OH [23]
CoFe layered double oxide/g-C3N4/PMS paracetamol [catalyst] = 0.2 g/L, [PMS] = 0.5 mM, [paracetamol] = 10 mg/L, temperature = 25 ± 0.5 °C, initial pH = 7 ± 0.2. 100% in less than 10 min SO4●− [24]
Co3O4/PMS Acid Orange 7 [AO7] = 0.2 mM, [PMS] = 2 mM and [nano-Co3O4] = 0.5 g/L, pH = 7. 100% with 60 min SO4●− [25]
Co-MCM41 Caffeine (CAF) [CAF] = 0.05 mM, [PMS] = 0.2 mM, [catalyst] = 200 mg/L, pH = 7.10. 100% with 15 min SO4•– and •OH [26]
Ag0.4-BiFeO3/PS tetracycline (TC) [catalysts] = 300 mg/L, [PS] = 5 mM, [TC] = 10 mg/L, pH = 4.5, T = 298 K. 91% with 60 min SO4●− and ●OH [27]
S-doped α-Fe2O3/PS carbamazepine (CBZ) [CBZ] = 2 mg/L, [PS]0 = 0.2 mM, [catalyst] = 0.2 g/L, T = 25 ± 1 °C and initial pH = 6.8 ± 0.5. 93.13% with 30 min SO4●− [28]
Fe3O4@Zn/Co-ZIFs/PMS carbamazepine (CBZ) [CBZ] = 5 mg/L, [catalyst] = 25 mg/L, [PMS] = 0.4 mM, initial pH = 6.8, T = 30 °C. 100% with 30 min SO4●− [29]
Co3O4/C-BC/PMS Bisphenol A (BPA) [catalyst] = 0.3 g/L, [pollutant] = 20 mg/L, [PMS] = 1.0 mmol/L, [pH] = 7.0, [T] = 30 °C. 100% within less than 30 min SO4●− [30]
ZnO/biochar/PS tetracycline hydrochloride (TC) [TC] = 0.05 g/L, [ZnO200/BC] = 0.1 g/L, [PS] = 1.0 mM, pH = 7.0 ± 0.1, T = 25 ± 2 °C. 44.98% with 50 min SO4●− and ●OH [31]
microwave irradiation(MW)/CuO/PS 2,4-dichlorophenol (2,4-DCP) [PS] = 0.4 g/L, [CuO] = 40 mg/L, (2,4-DCP) = 50 mg/L, initial pH = 9, MW power intensity = 180 W. >98% with 90 min SO4●− [32]
Ultrasound/Fe0/PS Sulfadiazine (SD) [SD] = 20 mg/L, [Fe0] = 0.92 Mm, [PS] = 1.84 mM, US input power = 90 W, initial pH = 7, room temperature. 99.1% with 60 min SO4●− [33]
granular activated carbon (GAC)/PMS Acid Orange 7 (AO7) [AO7] = 20 mg/L, [PMS]: [AO7] = 100:1, [GAC] = 1.0 g/L, without pH adjustment, T = 20 ± 0.5 °C. 85% with 5 h SO4●− [34]
Fe3O4@Graphene oxide (GO)/PS Rhodamine B (RhB) [RhB] = 20 ppm, [Fe3O4@GO] = 500 mg/L, [PS] = 1.5 mM, pH = 4.34, T = 20 °C. 89% with 120 min SO4●− [35]
alkali and CuO/PS Cu-ethylenediamine tetraacetic acid (Cu(II)-EDTA) [Cu(II)-EDTA] = 3.14 mM, [PS]/[Cu(II)-EDTA] = 15:1, [CuO] = 2 g/L, pH maintained at 11. Nearly 100% with 120 min SO4•−, •OH and O2•− [36]

3. Singlet Oxygen-Based Advanced Oxidation

With the report of PMS and PS non-radical activation, people gradually have a strong interest in the process of non-radical oxidation. Non-radical reactive species are generally thought to be resistant to common free radical scavengers (e.g., methanol, ethanol, and tert-butanol), selective to electron-rich organic compounds, and particularly sensitive to organic substrates with mild redox potentials [37]. At present, non-radical oxidation processes have been found in a variety of reaction systems, especially in PMS and PS activation. However, the mechanism remains controversial. Based on current reports, carbon or metal catalysts mainly realize non-radical activation of oxidants (PMS, PS, H2O2, or O3) through three ways: electron transfer process, generation of activated complexes (or surface-bound radicals) and singlet oxygen participating in pollutant degradation, respectively, as shown in Figure 1. Among them, 1O2 shows significant advantages in the selective removal of organic pollutants, which has become the focus of research.
/media/item_content/202210/63465ddca2e19catalysts-12-01092-g004.png
Figure 1. Schematic diagram of organic pollutants degradation by non-radical AOPs (Oxidant can be PMS, PS, H2O2 or O3).

This entry is adapted from the peer-reviewed paper 10.3390/catal12101092

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