Cobalt/Peracetic Acid: Advanced Oxidation of Aromatic Organic Compounds by Acetylperoxyl Radicals

  • Juhee Kim
    Juhee Kim
    School of Civil and Environmental Engineering, Georgia Institute of Technology, Atlanta, Georgia 30332, United States
    More by Juhee Kim
  • Penghui Du
    Penghui Du
    Beijing Engineering Research Center of Process Pollution Control, Division of Environment Technology and Engineering, Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, China
    More by Penghui Du
  • Wen Liu
    Wen Liu
    College of Environmental Sciences and Engineering, Peking University, Beijing 100871, China
    More by Wen Liu
  • Cong Luo
    Cong Luo
    School of Civil and Environmental Engineering, Georgia Institute of Technology, Atlanta, Georgia 30332, United States
    More by Cong Luo
  • He Zhao
    He Zhao
    Beijing Engineering Research Center of Process Pollution Control, Division of Environment Technology and Engineering, Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, China
    More by He Zhao
  • , and 
  • Ching-Hua Huang*
    Ching-Hua Huang
    School of Civil and Environmental Engineering, Georgia Institute of Technology, Atlanta, Georgia 30332, United States
    *Email: [email protected]
Cite this: Environ. Sci. Technol. 2020, 54, 8, 5268–5278
Publication Date (Web):March 18, 2020
https://doi.org/10.1021/acs.est.0c00356
Copyright © 2020 American Chemical Society
Article Views
2229
Altmetric
-
Citations
LEARN ABOUT THESE METRICS
Read OnlinePDF (1 MB)
Supporting Info (1)»

Abstract

Peracetic acid (PAA) is increasingly used as an alternative disinfectant and its advanced oxidation processes (AOPs) could be useful for pollutant degradation. Co(II) or Co(III) can activate PAA to produce acetyloxyl (CH3C(O)O) and acetylperoxyl (CH3C(O)OO) radicals with little OH radical formation, and Co(II)/Co(III) is cycled. For the first time, this study determined the reaction rates of PAA with Co(II) (kPAA,Co(II) = 1.70 × 101 to 6.67 × 102 M–1·s–1) and Co(III) (kPAA,Co(III) = 3.91 × 100 to 4.57 × 102 M–1·s–1) ions over the initial pH 3.0–8.2 and evaluated 30 different aromatic organic compounds for degradation by Co/PAA. In-depth investigation confirmed that CH3C(O)OO is the key reactive species under Co/PAA for compound degradation. Assessing the structure–activity relationship between compounds’ molecular descriptors and pseudo-first-order degradation rate constants (kPAA in s–1) by Co/PAA showed the number of ring atoms, EHOMO, softness, and ionization potential to be the most influential, strongly suggesting the electron transfer mechanism from aromatic compounds to the acetylperoxyl radical. The radical production and compound degradation in Co/PAA are most efficient in the intermediate pH range and can be influenced by water matrix constituents of bicarbonate, phosphate, and humic acids. These results significantly improve the knowledge regarding the acetylperoxyl radical from PAA and will be useful for further development and applications of PAA-based AOPs.

Supporting Information

ARTICLE SECTIONS
Jump To

The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.est.0c00356.

  • Chemicals and reagents; analytical methods; kinetic modeling for the reaction of PAA with cobalt ions; species calculation of cobalt ions; selected properties of two oxidants, peracetic acid, and hydrogen peroxide, and 30 target compounds; 28 QSAR descriptors used in this study; estimated second-order rate constants of PAA decomposition by Co(II) or Co(III); Pseudo-first-order rate constants (kobs) of degradation of BPA, NAP, SMX, and CBZ by Co(II)/PAA at initial pH 3.0–8.1 and 22 °C (R2 > 0.931); pseudo-first-order rate constants (kobs) of degradation of CBZ by Co(II)/PAA depending on different molar ratios of PAA to Fe(II) or H2O2 at initial pH 7.1 and 22 °C (R2 > 0.940); pseudo-first-order rate constants (kobs) of degradation of CBZ by Co(II)/PAA in the presence of Cl, HCO3, PO43–, and HA at initial pH 7.1 and 22 °C (R2 > 0.944); correlation between ln kPAA values of different compounds and all the descriptors (n = 30); structural activity relationship between the ln kPAA training data and molecular descriptors; change in absorption spectra Co(II) solution after adding PAA; and H2O2 decrease by mixing Co(II) or Co(III) with and without PAA at pH 6.9 at 22 °C (PDF)

Terms & Conditions

Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

Cited By


This article is cited by 44 publications.

  1. Zihao Zhao, Xinhong Li, Hongchao Li, Jieshu Qian, Bingcai Pan. New Insights into the Activation of Peracetic Acid by Co(II): Role of Co(II)-Peracetic Acid Complex as the Dominant Intermediate Oxidant. ACS ES&T Engineering 2021, 1 (10) , 1432-1440. https://doi.org/10.1021/acsestengg.1c00166
  2. Banghai Liu, Wanqian Guo, Wenrui Jia, Huazhe Wang, Qishi Si, Qi Zhao, Haichao Luo, Jin Jiang, Nanqi Ren. Novel Nonradical Oxidation of Sulfonamide Antibiotics with Co(II)-Doped g-C3N4-Activated Peracetic Acid: Role of High-Valent Cobalt–Oxo Species. Environmental Science & Technology 2021, 55 (18) , 12640-12651. https://doi.org/10.1021/acs.est.1c04091
  3. Ruobai Li, Kyriakos Manoli, Juhee Kim, Mingbao Feng, Ching-Hua Huang, Virender K. Sharma. Peracetic Acid–Ruthenium(III) Oxidation Process for the Degradation of Micropollutants in Water. Environmental Science & Technology 2021, 55 (13) , 9150-9160. https://doi.org/10.1021/acs.est.0c06676
  4. Hongchao Li, Zihao Zhao, Jieshu Qian, Bingcai Pan. Are Free Radicals the Primary Reactive Species in Co(II)-Mediated Activation of Peroxymonosulfate? New Evidence for the Role of the Co(II)–Peroxymonosulfate Complex. Environmental Science & Technology 2021, 55 (9) , 6397-6406. https://doi.org/10.1021/acs.est.1c02015
  5. Juhee Kim, Ching-Hua Huang. Reactivity of Peracetic Acid with Organic Compounds: A Critical Review. ACS ES&T Water 2021, 1 (1) , 15-33. https://doi.org/10.1021/acsestwater.0c00029
  6. Jingwen Wang, Ying Wan, Jiaqi Ding, Zongping Wang, Jun Ma, Pengchao Xie, Mark R. Wiesner. Thermal Activation of Peracetic Acid in Aquatic Solution: The Mechanism and Application to Degrade Sulfamethoxazole. Environmental Science & Technology 2020, 54 (22) , 14635-14645. https://doi.org/10.1021/acs.est.0c02061
  7. Jie Dong, Weihua Xu, Shaobo Liu, Youzi Gong, Ting Yang, Li Du, Qiang Chen, Xiaofei Tan, Yunguo Liu. Lignin-derived biochar to support CoFe2O4: Effective activation of peracetic acid for sulfamethoxazole degradation. Chemical Engineering Journal 2022, 430 , 132868. https://doi.org/10.1016/j.cej.2021.132868
  8. Yang Zong, Hua Zhang, Yufei Shao, Wenjie Ji, Yunqiao Zeng, Longqian Xu, Deli Wu. Surface-mediated periodate activation by nano zero-valent iron for the enhanced abatement of organic contaminants. Journal of Hazardous Materials 2022, 423 , 126991. https://doi.org/10.1016/j.jhazmat.2021.126991
  9. Runyu Zhou, Yongsheng Fu, Gaofeng Zhou, Shixiang Wang, Yiqing Liu. Heterogeneous degradation of organic contaminants by peracetic acid activated with FeCo2S4 modified g-C3N4: Identification of reactive species and catalytic mechanism. Separation and Purification Technology 2022, 282 , 120082. https://doi.org/10.1016/j.seppur.2021.120082
  10. Kyriakos Manoli, Ruobai Li, Juhee Kim, Mingbao Feng, Ching-Hua Huang, Virender K. Sharma. Ferrate(VI)-peracetic acid oxidation process: Rapid degradation of pharmaceuticals in water. Chemical Engineering Journal 2022, 429 , 132384. https://doi.org/10.1016/j.cej.2021.132384
  11. Yang Zong, Hua Zhang, Xiaomeng Zhang, Wen Liu, Longqian Xu, Deli Wu. High-valent cobalt-oxo species triggers hydroxyl radical for collaborative environmental decontamination. Applied Catalysis B: Environmental 2022, 300 , 120722. https://doi.org/10.1016/j.apcatb.2021.120722
  12. Jie Zuo, Xiangqian Xu, Qiqi Wan, Ruihua Cao, Zhiting Liang, Huining Xu, Kai Li, Tinglin Huang, Gang Wen, Jun Ma. Inactivation of fungal spores in water with peracetic acid: Efficiency and mechanism. Chemical Engineering Journal 2022, 427 , 131753. https://doi.org/10.1016/j.cej.2021.131753
  13. Jun Hu, Tong Li, Xuxiang Zhang, Hongqiang Ren, Hui Huang. Degradation of steroid estrogens by UV/peracetic acid: Influencing factors, free radical contribution and toxicity analysis. Chemosphere 2022, 287 , 132261. https://doi.org/10.1016/j.chemosphere.2021.132261
  14. Jiewen Deng, Hongbin Wang, Yongsheng Fu, Yiqing Liu. Phosphate-induced activation of peracetic acid for diclofenac degradation: Kinetics, influence factors and mechanism. Chemosphere 2022, 287 , 132396. https://doi.org/10.1016/j.chemosphere.2021.132396
  15. Jingwen Wang, Zongping Wang, Yujie Cheng, Lisan Cao, Pengchao Xie, Jun Ma. Molybdenum disulfide (MoS2) promoted sulfamethoxazole degradation in the Fe(III)/peracetic acid process. Separation and Purification Technology 2022, 281 , 119854. https://doi.org/10.1016/j.seppur.2021.119854
  16. Deling Yuan, Kai Yang, Shiyu Pan, Yao Xiang, Shoufeng Tang, Liting Huang, Mengting Sun, Xiaoyu Zhang, Tifeng Jiao, Qingrui Zhang, Bing Li. Peracetic acid enhanced electrochemical advanced oxidation for organic pollutant elimination. Separation and Purification Technology 2021, 276 , 119317. https://doi.org/10.1016/j.seppur.2021.119317
  17. Zhenran Wang, Yongsheng Fu, Yunlan Peng, Shixiang Wang, Yiqing Liu. HCO3–/CO32– enhanced degradation of diclofenac by Cu(Ⅱ)-activated peracetic acid: Efficiency and mechanism. Separation and Purification Technology 2021, 277 , 119434. https://doi.org/10.1016/j.seppur.2021.119434
  18. Jinbin Lin, Jing Zou, Hengyu Cai, Yixin Huang, Jiawen Li, Junyang Xiao, Baoling Yuan, Jun Ma. Hydroxylamine enhanced Fe(II)-activated peracetic acid process for diclofenac degradation: Efficiency, mechanism and effects of various parameters. Water Research 2021, 207 , 117796. https://doi.org/10.1016/j.watres.2021.117796
  19. Dušan S. Dimić, Dejan A. Milenković, Edina H. Avdović, Đura J. Nakarada, Jasmina M. Dimitrić Marković, Zoran S. Marković. Advanced oxidation processes of coumarins by hydroperoxyl radical: An experimental and theoretical study, and ecotoxicology assessment. Chemical Engineering Journal 2021, 424 , 130331. https://doi.org/10.1016/j.cej.2021.130331
  20. Longlong Zhang, Jiabin Chen, Yalei Zhang, Zhenjiang Yu, Ruicheng Ji, Xuefei Zhou. Activation of peracetic acid with cobalt anchored on 2D sandwich-like MXenes ([email protected]) for organic contaminant degradation: High efficiency and contribution of acetylperoxyl radicals. Applied Catalysis B: Environmental 2021, 297 , 120475. https://doi.org/10.1016/j.apcatb.2021.120475
  21. Pengyu Zhang, Xianfa Zhang, Xiaodan Zhao, Guohua Jing, Zuoming Zhou. Activation of peracetic acid with zero-valent iron for tetracycline abatement: The role of Fe(II) complexation with tetracycline. Journal of Hazardous Materials 2021, 188 , 127653. https://doi.org/10.1016/j.jhazmat.2021.127653
  22. Chaomeng Dai, Yueming Han, Yanping Duan, Xiaoying Lai, Rongbing Fu, Shuguang Liu, Kah Hon Leong, Yaojen Tu, Lang Zhou. Review on the contamination and remediation of polycyclic aromatic hydrocarbons (PAHs) in coastal soil and sediments. Environmental Research 2021, 25 , 112423. https://doi.org/10.1016/j.envres.2021.112423
  23. Jun Duan, Long Chen, Haodong Ji, Peishen Li, Fan Li, Wen Liu. Activation of peracetic acid by metal-organic frameworks (ZIF-67) for efficient degradation of sulfachloropyridazine. Chinese Chemical Letters 2021, 418 https://doi.org/10.1016/j.cclet.2021.11.072
  24. Dariusz Kiejza, Urszula Kotowska, Weronika Polińska, Joanna Karpińska. Peracids - New oxidants in advanced oxidation processes: The use of peracetic acid, peroxymonosulfate, and persulfate salts in the removal of organic micropollutants of emerging concern − A review. Science of The Total Environment 2021, 790 , 148195. https://doi.org/10.1016/j.scitotenv.2021.148195
  25. Xiaocui Wu, Qingshan Zhao, Fang Guo, Guangsen Xia, Xiaojie Tan, Huiyuan Lv, Zhaoxuan Feng, Wenting Wu, Jingtang Zheng, Mingbo Wu. Porous g-C3N4 and α-FeOOH bridged by carbon dots as synergetic visible-light-driven photo-fenton catalysts for contaminated water remediation. Carbon 2021, 183 , 628-640. https://doi.org/10.1016/j.carbon.2021.07.006
  26. Bingkun Huang, Zhaokun Xiong, Peng Zhou, Heng Zhang, Zhicheng Pan, Gang Yao, Bo Lai. Ultrafast degradation of contaminants in a trace cobalt(II) activated peroxymonosulfate process triggered through borate: Indispensable role of intermediate complex. Journal of Hazardous Materials 2021, 335 , 127641. https://doi.org/10.1016/j.jhazmat.2021.127641
  27. Liang Meng, Jing Chen, Deyang Kong, Yuefei Ji, Junhe Lu, Xiaoming Yin, Quansuo Zhou. Transformation of bromide and formation of brominated disinfection byproducts in peracetic acid oxidation of phenol. Chemosphere 2021, 39 , 132698. https://doi.org/10.1016/j.chemosphere.2021.132698
  28. Jinbin Lin, Yuye Hu, Junyang Xiao, Yixin Huang, Mengyun Wang, Haoyu Yang, Jing Zou, Baoling Yuan, Jun Ma. Enhanced diclofenac elimination in Fe(II)/peracetic acid process by promoting Fe(III)/Fe(II) cycle with ABTS as electron shuttle. Chemical Engineering Journal 2021, 420 , 129692. https://doi.org/10.1016/j.cej.2021.129692
  29. Zhuang Wu, Lina Wang, Bo Lu, André K. Eckhardt, Peter R. Schreiner, Xiaoqing Zeng. Spectroscopic characterization and photochemistry of the vinylsulfinyl radical. Physical Chemistry Chemical Physics 2021, 23 (30) , 16307-16315. https://doi.org/10.1039/D1CP02584H
  30. Jingwen Wang, Zongping Wang, Yujie Cheng, Lisan Cao, Fan Bai, Siyang Yue, Pengchao Xie, Jun Ma. Molybdenum disulfide (MoS2): A novel activator of peracetic acid for the degradation of sulfonamide antibiotics. Water Research 2021, 201 , 117291. https://doi.org/10.1016/j.watres.2021.117291
  31. Banghai Liu, Wanqian Guo, Wenrui Jia, Huazhe Wang, Shanshan Zheng, Qishi Si, Qi Zhao, Haichao Luo, Jin Jiang, Nanqi Ren. Insights into the oxidation of organic contaminants by Co(II) activated peracetic acid: The overlooked role of high-valent cobalt-oxo species. Water Research 2021, 201 , 117313. https://doi.org/10.1016/j.watres.2021.117313
  32. Banghai Liu, Wanqian Guo, Huazhe Wang, Shanshan Zheng, Qishi Si, Qi Zhao, Haichao Luo, Nanqi Ren. Peroxymonosulfate activation by cobalt(II) for degradation of organic contaminants via high-valent cobalt-oxo and radical species. Journal of Hazardous Materials 2021, 416 , 125679. https://doi.org/10.1016/j.jhazmat.2021.125679
  33. Mingxue Li, Jianfei Sun, Qiong Mei, Bo Wei, Zexiu An, Haijie Cao, Chao Zhang, Ju Xie, Jinhua Zhan, Wenxing Wang, Maoxia He, Qiao Wang. Acetaminophen degradation by hydroxyl and organic radicals in the peracetic acid-based advanced oxidation processes: Theoretical calculation and toxicity assessment. Journal of Hazardous Materials 2021, 416 , 126250. https://doi.org/10.1016/j.jhazmat.2021.126250
  34. Han Chen, Tao Lin, Shisheng Zhang, Hang Xu, Hui Tao, Wei Chen. Novel FeII/EDDS/UV/PAA advanced oxidation process: Mechanisms and applications for naproxen degradation at neutral pH and low FeII dosage. Chemical Engineering Journal 2021, 417 , 127896. https://doi.org/10.1016/j.cej.2020.127896
  35. Xingfa Li, Dandan Liang, Chaoxu Wang, Yongguo Li. Insights into the peroxomonosulfate activation on boron-doped carbon nanotubes: Performance and mechanisms. Chemosphere 2021, 275 , 130058. https://doi.org/10.1016/j.chemosphere.2021.130058
  36. Jinglin Zhu, Shu Wang, Hongchao Li, Jieshu Qian, Lu Lv, Bingcai Pan. Degradation of phosphonates in Co(II)/peroxymonosulfate process: Performance and mechanism. Water Research 2021, 89 , 117397. https://doi.org/10.1016/j.watres.2021.117397
  37. Longlong Zhang, Jiabin Chen, Yalei Zhang, Tongcai Liu, Qiufang Yao, Libin Yang, Xuefei Zhou. Interactions between peracetic acid and TiO2 nanoparticle in wastewater disinfection: Mechanisms and implications. Chemical Engineering Journal 2021, 412 , 128703. https://doi.org/10.1016/j.cej.2021.128703
  38. Mingxue Li, Qiong Mei, Bo Wei, Zexiu An, Jianfei Sun, Ju Xie, Maoxia He. Mechanism and kinetics of ClO -mediated degradation of aromatic compounds in aqueous solution: DFT and QSAR studies. Chemical Engineering Journal 2021, 412 , 128728. https://doi.org/10.1016/j.cej.2021.128728
  39. Xiaojie Chai, Yan Cui, Wencai Xu, Lingce Kong, Yanjun Zuo, Ling Yuan, Wenming Chen. Degradation of malathion in the solution of acetyl peroxyborate activated by carbonate: Products, kinetics and mechanism. Journal of Hazardous Materials 2021, 407 , 124808. https://doi.org/10.1016/j.jhazmat.2020.124808
  40. Thi Bich Viet Nguyen, Ngan Nguyen-Bich, Ngoc Duy Vu, Hien Ho Phuong, Hanh Nguyen Thi, . Degradation of Reactive Blue 19 (RB19) by a Green Process Based on Peroxymonocarbonate Oxidation System. Journal of Analytical Methods in Chemistry 2021, 2021 , 1-8. https://doi.org/10.1155/2021/6696600
  41. Mohsen Ghafari, Tashfia M. Mohona, Lei Su, Haiqing Lin, Desiree L. Plata, Boya Xiong, Ning Dai. Effects of peracetic acid on aromatic polyamide nanofiltration membranes: a comparative study with chlorine. Environmental Science: Water Research & Technology 2021, 7 (2) , 306-320. https://doi.org/10.1039/D0EW01007C
  42. Jingwen Wang, Bin Xiong, Lei Miao, Songlin Wang, Pengchao Xie, Zongping Wang, Jun Ma. Applying a novel advanced oxidation process of activated peracetic acid by CoFe2O4 to efficiently degrade sulfamethoxazole. Applied Catalysis B: Environmental 2021, 280 , 119422. https://doi.org/10.1016/j.apcatb.2020.119422
  43. Xiu-wei Ao, Jussi Eloranta, Ching-Hua Huang, Domenico Santoro, Wen-jun Sun, Ze-dong Lu, Chen Li. Peracetic acid-based advanced oxidation processes for decontamination and disinfection of water: A review. Water Research 2021, 188 , 116479. https://doi.org/10.1016/j.watres.2020.116479
  44. Xuefei Zhou, Haowei Wu, Longlong Zhang, Bowen Liang, Xiaoqi Sun, Jiabin Chen. Activation of Peracetic Acid with Lanthanum Cobaltite Perovskite for Sulfamethoxazole Degradation under a Neutral pH: The Contribution of Organic Radicals. Molecules 2020, 25 (12) , 2725. https://doi.org/10.3390/molecules25122725