Citation: Meiru Hou, Xiaodie Li, Yu Fu, Lingli Wang, Dagang Lin, Zhaohui Wang. Degradation of iodinated X-ray contrast media by advanced oxidation processes: A literature review with a focus on degradation pathways[J]. Chinese Chemical Letters, ;2023, 34(4): 107723. doi: 10.1016/j.cclet.2022.08.003 shu

Degradation of iodinated X-ray contrast media by advanced oxidation processes: A literature review with a focus on degradation pathways

Meiru Hou ^a ,
Xiaodie Li ^a ,
Yu Fu ^a ,
Lingli Wang ^a ,
Dagang Lin ^a ,
Zhaohui Wang ^{a, b, c, *,}

a.
Shanghai Key Lab for Urban Ecological Processes and Eco-Restoration, School of Ecological and Environmental Sciences, East China Normal University, Shanghai 200241, China
b.
Technology Innovation Center for Land Spatial Eco-restoration in Metropolitan Area, Ministry of Natural Resources, Shanghai 200062, China
c.
Shanghai Engineering Research Center of Biotransformation of Organic Solid Waste, Shanghai 200241, China

zhwang@des.ecnu.edu.cn

Received Date: 19 May 2022
Revised Date: 20 June 2022
Accepted Date: 1 August 2022
Available Online: 2 August 2022

Figures(6)

Available online Iodinated X-ray contrast media (ICMs) are clinical drugs used to enhance the imaging effect. Triiodobenzene ring structures of ICMs lead to its extremely high chemical stability, biological inertness, which makes it difficult to be completely removed by traditional water treatment processes. Hence, considerable concentration of ICMs can be frequently detected in aquatic environment. Relying on the strong oxidation capacity of HO^• or SO₄^•‒, various advanced oxidation processes (AOPs) have demonstrated substantial removal efficiency for ICMs. It is evident that ICMs can be decomposed mainly through (1) deiodination, (2) dehydration, (3) decarboxylation, (4) H-abstraction, (5) hydroxyl addition, (6) hydroxyl substitution, (7) oxidation of alcohol groups, (8) cleavage of amide bond, and (9) amino oxidation. However, during the ICMs removal process, the C-I bonds of ICMs molecules are broken, giving rise to the formation of cytotoxic iodination disinfection by-products (I-DBPs) that are potentially more harmful to the ecosystem and human health than their parent compounds. To better understand the technology gaps, this review elaborates the major AOPs which are effective for ICMs removal and emphasizes on the main degradation routes of ICMs in different oxidation system. Some prevailing concerns and challenges are discussed for optimizing the ICMs treatment process.
- Iodinated X-ray contrast media,
- Sulfate radical,
- Deiodination,
- Hydroxyl radical,
- Transformation products
1. [1]
  I. Arslan-Alaton, T. Olmez-Hanci, G. Korkmaz, C. Sahin, Chem. Eng. J. 318 (2017) 64–75. doi: 10.1016/j.cej.2016.05.021
2. [2]
  W. Bottinor, P. Polkampally, I. Jovin, Int. J. Angiol. 22 (2013) 149–154. doi: 10.1055/s-0033-1348885
3. [3]
  T.A. Ternes, R. Hirsch, Environ. Sci. Technol. 34 (2000) 2741–2748. doi: 10.1021/es991118m
4. [4]
  T. Steger-Hartmann, R. L. aange, H. Schweinfurth, M. Tschampel, I. Rehmann, Water Res. 36 (2002) 266–274. doi: 10.1016/S0043-1354(01)00241-X
5. [5]
  S.B. Yu, A.D. Watson, Chem. Rev. 99 (1999) 2353–2377. doi: 10.1021/cr980441p
6. [6]
  K.G. Estep, K.A. Josef, E.R. Bacon, et al., J. Med. Chem. 43 (2000) 1940–1948. doi: 10.1021/jm990407i
7. [7]
  W. Zhang, I. Soutrel, A. Amrane, F. Fourcade, F. Geneste, Front. Chem. 8 (2020) 646. doi: 10.3389/fchem.2020.00646
8. [8]
  C.Y. Hu, Y.Z. Hou, Y.L. Lin, et al., Chemosphere 229 (2019) 602–610. doi: 10.1016/j.chemosphere.2019.05.012
9. [9]
  C.Y. Hu, S.C. Ren, Y.L. Lin, et al., J. Water Reuse Desal. 11 (2021) 560–571. doi: 10.2166/wrd.2021.053
10. [10]
  S.E. Duirk, C. Lindell, C.C. Cornelison, et al., Environ. Sci. Technol. 45 (2011) 6845–6854. doi: 10.1021/es200983f
11. [11]
  T. Ye, B. Xu, Z. Wang, et al., Water Res. 66 (2014) 390–398. doi: 10.1016/j.watres.2014.08.044
12. [12]
  T. Steger-Hartmann, R. Länge, H. Schweinfurth, Environ. Res. 42 (1999) 274–281.
13. [13]
  S.S. Kabirhashemi, H. Eskandari, Sens. Actuators B: Chem. 348 (2021) 130731. doi: 10.1016/j.snb.2021.130731
14. [14]
  S. Gartiser, L. Brinker, T. Erbe, K. Kummerer, R. Willmund, Acta Hydroch. Hydrob. 24 (1996) 90–97. doi: 10.1002/aheh.19960240206
15. [15]
  K. Kuemmerer, T. Erbe, S. Gartiser, L. Brinker, Chemosphere 36 (1998) 2437–2445. doi: 10.1016/S0045-6535(97)10200-4
16. [16]
  T.E. Doll, F.H. Frimmel, Water Res. 38 (2004) 955–964. doi: 10.1016/j.watres.2003.11.009
17. [17]
  A. Putschew, S. Wischnack, M. Jekel, Environ. Sci. Technol. 255 (2000) 129–134.
18. [18]
  S.D. Richardson, F. Fasano, J.J. Ellington, et al., Environ. Sci. Technol. 42 (2008) 8330–8338. doi: 10.1021/es801169k
19. [19]
  H. Dong, Z. Qiang, J. Lian, et al., Water Res. 129 (2018) 319–326. doi: 10.1016/j.watres.2017.11.032
20. [20]
  S. Pérez, D. Barceló, Anal. Bioanal. Chem. 387 (2007) 1235–1246. doi: 10.1007/s00216-006-0953-9
21. [21]
  W. Kalsch, Sci. Total Environ. 225 (1999) 143–153. doi: 10.1016/S0048-9697(98)00340-4
22. [22]
  T. Erbe, K. Kümmerer, S. Gartiser, L. Brinker, Fortschr. Röntgenstr. 169 (1998) 420–423. doi: 10.1055/s-2007-1015310
23. [23]
  T.A. Ternes, Water Res. 32 (1998) 3245–3260. doi: 10.1016/S0043-1354(98)00099-2
24. [24]
  D. Kanakaraju, B.D. Glass, M. Oelgemoller, J. Environ. Manage. 219 (2018) 189–207. doi: 10.1016/j.jenvman.2018.04.103
25. [25]
  S. Perez, P. Eichhorn, M.D. Celiz, D.S. Aga, Anal. Chem. 78 (2006) 1866–1874. doi: 10.1021/ac0518809
26. [26]
  G. Teijon, L. Candela, K. Tamoh, A. Molina-Diaz, A.R. Fernandez-Alba, Sci. Total Environ. 408 (2010) 3584–3595. doi: 10.1016/j.scitotenv.2010.04.041
27. [27]
  S. Schittko, A. Putschew, M. Jekel, Water Sci. Technol. 50 (2004) 261–268.
28. [28]
  D. Weissbrodt, L. Kovalova, C. Ort, et al., Environ. Sci. Technol. 43 (2009) 4810–4817. doi: 10.1021/es8036725
29. [29]
  K. Nodler, T. Licha, K. Bester, M. Sauter, J. Chromatogr A 1217 (2010) 6511–6521. doi: 10.1016/j.chroma.2010.08.048
30. [30]
  A. Tiehm, N. Schmidt, M. Stieber, et al., Water Resour. Manage. 25 (2011) 1195–1203. doi: 10.1007/s11269-010-9678-9
31. [31]
  I.J. Lopez-Prieto, S. Wu, W. Ji, K.D. Daniels, S.A. Snyder, Chemosphere 243 (2020) 125311. doi: 10.1016/j.chemosphere.2019.125311
32. [32]
  A. Sengar, A. Vijayanandan, Sci. Total Environ. 769 (2021) 144846. doi: 10.1016/j.scitotenv.2020.144846
33. [33]
  A. Sengar, A. Vijayanandan, Sci. Total Environ. 807 (2022) 150677. doi: 10.1016/j.scitotenv.2021.150677
34. [34]
  Y. Watanabe, L.T. Bach, P. Van Dinh, et al., Arch. Environ. Contam. Toxicol. 70 (2016) 671–681. doi: 10.1007/s00244-015-0220-1
35. [35]
  B. Yao, S. Yan, L. Lian, et al., Environ. Pollut. 236 (2018) 889–898. doi: 10.1016/j.envpol.2017.10.032
36. [36]
  Y.Y. Yang, J.L. Zhao, Y.S. Liu, et al., Sci. Total Environ. 616-617 (2018) 816–823.
37. [37]
  T. Azuma, K. Otomo, M. Kunitou, et al., Sci. Total Environ. 657 (2019) 476–484. doi: 10.1016/j.scitotenv.2018.11.433
38. [38]
  D. Fabbri, P. Calza, D. Dalmasso, et al., Sci. Total Environ. 572 (2016) 340–351. doi: 10.1016/j.scitotenv.2016.08.003
39. [39]
  K. Nodler, D. Voutsa, T. Licha, Mar. Pollut. Bull. 85 (2014) 50–59. doi: 10.1016/j.marpolbul.2014.06.024
40. [40]
  C. Valls-Cantenys, M. Scheurer, M. Iglesias, et al., Anal. Bioanal. Chem. 408 (2016) 6189–6200. doi: 10.1007/s00216-016-9731-5
41. [41]
  R. Münze, C. Hannemann, P. Orlinskiy, et al., Sci. Total Environ. 599 (2017) 387–399.
42. [42]
  K. Ribbers, L. Breuer, R.A. During, Chemosphere 218 (2019) 189–196. doi: 10.1016/j.chemosphere.2018.10.193
43. [43]
  J.L. Kormos, M. Schulz, T.A. Ternes, Environ. Sci. Technol. 45 (2011) 8723–8732. doi: 10.1021/es2018187
44. [44]
  L. Wolf, C. Zwiener, M. Zemann, Sci. Total Environ. 430 (2012) 8–19. doi: 10.1016/j.scitotenv.2012.04.059
45. [45]
  L. Candela, K. Tamoh, I. Vadillo, J. Valdes-Abellan, Environ. Earth Sci. 75 (2016) 244. doi: 10.1007/s12665-015-4956-8
46. [46]
  W. Seitz, R. Winzenbacher, Environ. Monit. Assess. 189 (2017) 244. doi: 10.1007/s10661-017-5953-z
47. [47]
  D. Simazaki, R. Kubota, T. Suzuki, et al., Water Res. 76 (2015) 187–200. doi: 10.1016/j.watres.2015.02.059
48. [48]
  Z. Xu, X. Li, X. Hu, D. Yin, Chemosphere 184 (2017) 253–260. doi: 10.1016/j.chemosphere.2017.05.048
49. [49]
  W. Ens, F. Senner, B. Gygax, G. Schlotterbeck, Anal. Bioanal. Chem. 406 (2014) 2789–2798. doi: 10.1007/s00216-014-7712-0
50. [50]
  A. Mendoza, B. Zonja, N. Mastroianni, et al., Environ. Int. 86 (2016) 107–118. doi: 10.1016/j.envint.2015.11.001
51. [51]
  T. Azuma, K. Otomo, M. Kunitou, et al., Sep. Purif. Technol. 212 (2019) 483–489. doi: 10.1016/j.seppur.2018.11.059
52. [52]
  T.A. Ternes, J. Stüber, N. Herrmann, et al., Water Res. 37 (2003) 1976–1982. doi: 10.1016/S0043-1354(02)00570-5
53. [53]
  R. Andreozzi, V. Caprio, A. Insola, R. Marotta, Catal. Today 53 (1999) 51–59. doi: 10.1016/S0920-5861(99)00102-9
54. [54]
  B. Legube, N.K.V. Leitner, Catal. Today 53 (1999) 61–72. doi: 10.1016/S0920-5861(99)00103-0
55. [55]
  F.J. Beltran, F.J. Rivas, R. Montero-de-Espinosa, Appl. Catal. B: Environ. 39 (2002) 221–231. doi: 10.1016/S0926-3373(02)00102-9
56. [56]
  S.J. Masten, S.H.R. Davies, Environ. Sci Technol. 28 (1994) 180–185. doi: 10.1021/es00053a001
57. [57]
  U. Von Gunten, Water Res. 37 (2003) 1443–1467. doi: 10.1016/S0043-1354(02)00457-8
58. [58]
  M.O. Buffle, J. Schumacher, S. Meylan, M. Jekel, U. von Gunten, Ozone Sci. Eng. 28 (2006) 247–259. doi: 10.1080/01919510600718825
59. [59]
  T. Matsushita, M. Hashizuka, T. Kuriyama, Y. Matsui, N. Shirasaki, Chemosphere 148 (2016) 233–240. doi: 10.1016/j.chemosphere.2016.01.037
60. [60]
  M.M. Huber, A.G. Bel, A. Joss, et al., Environ. Sci. Technol. 39 (2005) 4290–4299. doi: 10.1021/es048396s
61. [61]
  W. Seitz, J.Q. Jiang, W. Schulz, et al., Chemosphere 70 (2008) 1238–1246. doi: 10.1016/j.chemosphere.2007.07.081
62. [62]
  L. Kovalova, H. Siegrist, U. von Gunten, et al., Environ. Sci. Technol. 47 (2013) 7899–7908. doi: 10.1021/es400708w
63. [63]
  L. Ferrando-Climent, R. Gonzalez-Olmos, A. Anfruns, et al., Chemosphere 168 (2017) 284–292. doi: 10.1016/j.chemosphere.2016.10.057
64. [64]
  J.L. Acero, U. Von Gunten, J. Am. Water Work Assoc. 93 (2001) 90–100.
65. [65]
  R. Gulde, B. Clerc, M. Rutsch, et al., Water Res. 207 (2021) 117812. doi: 10.1016/j.watres.2021.117812
66. [66]
  A.D. Bokare, W. Choi, J. Hazard. Mater. 275 (2014) 121–135. doi: 10.1016/j.jhazmat.2014.04.054
67. [67]
  N.N. Wang, T. Zheng, G.S. Zhang, P. Wang, J. Environ. 4 (2016) 762–787.
68. [68]
  I. Velo-Gala, J.J. López-Peñalver, M. Sánchez-Polo, J. Rivera-Utrilla, Chem. Eng. J. 241 (2014) 504–512. doi: 10.1016/j.cej.2013.10.036
69. [69]
  X. Tao, J.M. Su, J.F. Chen, J.C. Zhao, Chem. Commun. 36 (2005) 4607–4609.
70. [70]
  F.J. Real, F.J. Benitez, J.L. Acero, J.J.P. Sagasti, F. Casas, Ind. Eng. Chem. Res. 48 (2009) 3380–3388. doi: 10.1021/ie801762p
71. [71]
  E. Bocos, N. Oturan, M. Pazos, M.A. Sanroman, M.A. Oturan, Environ. Sci. Pollut. Res. Int. 23 (2016) 19134–19144. doi: 10.1007/s11356-016-7054-x
72. [72]
  J. Jeong, J. Yoon, Water Res. 39 (2005) 2893–2900. doi: 10.1016/j.watres.2005.05.014
73. [73]
  Y. Zuo, J. Zhan, Atmos. Environ. 39 (2005) 27–37. doi: 10.1016/j.atmosenv.2004.09.058
74. [74]
  F. Gulshan, S. Yanagida, Y. Kameshima, et al., Water Res. 44 (2010) 2876–2884. doi: 10.1016/j.watres.2010.01.040
75. [75]
  C. Zhao, L.E. Arroyo-Mora, A.P. DeCaprio, et al., Water Res. 67 (2014) 144–153. doi: 10.1016/j.watres.2014.09.009
76. [76]
  T.E. Doll, F.H. Frimmel, Chemosphere 52 (2003) 1757–1769. doi: 10.1016/S0045-6535(03)00446-6
77. [77]
  M. Sprehe, S.U. Geiûen, A. Vogelpohl, Water Sci. Technol. 44 (2001) 317–323.
78. [78]
  G. Prados-Joya, M. Sanchez-Polo, J. Rivera-Utrilla, M. Ferro-Garcia, Water Res. 45 (2011) 393–403. doi: 10.1016/j.watres.2010.08.015
79. [79]
  T.E. Doll, F.H. Frimmel, Water Res. 39 (2005) 403–411. doi: 10.1016/j.watres.2004.09.016
80. [80]
  M.N. Sugihara, D. Moeller, T. Paul, T.J. Strathmann, Appl. Catal. B: Environ. 129 (2013) 114–122. doi: 10.1016/j.apcatb.2012.09.013
81. [81]
  J.M. Herrmann, Catal. Today 53 (1999) 115–129. doi: 10.1016/S0920-5861(99)00107-8
82. [82]
  J.Z. Zhang, J. Phys. Chem. B 104 (2000) 7239–7253.
83. [83]
  D.D. Dionysiou, M.T. Suidan, I. Baudin, J.M. Laine, Appl. Catal. B: Environ. 50 (2004) 259–269. doi: 10.1016/j.apcatb.2004.01.022
84. [84]
  K.A. Hislop, J.R. Bolton, Environ. Sci. Technol. 33 (1999) 3119–3126. doi: 10.1021/es9810134
85. [85]
  A.K. Biń, S. Sobera-Madej, Ozone Sci. Eng. 34 (2012) 136–139. doi: 10.1080/01919512.2012.650130
86. [86]
  X.X. He, M. Pelaez, J.A. Westrick, et al., Water Res. 46 (2012) 1501–1510. doi: 10.1016/j.watres.2011.11.009
87. [87]
  X. Zhao, J. Jiang, S. Pang, et al., Chemosphere 221 (2019) 270–277. doi: 10.1016/j.chemosphere.2018.12.162
88. [88]
  C.C. Wong, W. Chu, Environ. Sci. Technol. 37 (2003) 2310–2316. doi: 10.1021/es020898n
89. [89]
  S. Perez, P. Eichhorn, V. Ceballos, D. Barcelo, J. Mass Spectrom. 44 (2009) 1308–1317. doi: 10.1002/jms.1613
90. [90]
  M. Sprehe, S.U. Geissen, A. Vogelpohl, Water Sci. Technol. 44 (2001) 317–323.
91. [91]
  E. Borowska, E. Felis, S. Zabczynski, Water Air Soil Pollut 226 (2015) 151. doi: 10.1007/s11270-015-2383-9
92. [92]
  C. Sichel, C. Garcia, K. Andre, Water Res. 45 (2011) 6371–6380. doi: 10.1016/j.watres.2011.09.025
93. [93]
  X. Kong, J. Jiang, J. Ma, Y. Yang, S. Pang, Chemosphere 193 (2018) 655–663. doi: 10.1016/j.chemosphere.2017.11.064
94. [94]
  C.Y. Hu, Y.Z. Hou, Y.L. Lin, A.P. Li, Y.G. Deng, Chemosphere 360 (2019) 1003–1010.
95. [95]
  G.V. Buxton, C.L. Greenstock, W.P. Helman, A.B. Ross, J. Phys. Chem. 17 (1988) 514–886.
96. [96]
  S.J. Zhang, H. Jiang, M.J. Li, et al., Environ. Sci. Technol. 41 (2007) 1977–1982. doi: 10.1021/es062031l
97. [97]
  Q. Zhao, R. Goto, T. Saito, T. Kobayashi, T. Sasaki, Chemosphere 256 (2020) 127021. doi: 10.1016/j.chemosphere.2020.127021
98. [98]
  Q. Zhao, T. Kobayashi, T. Saito, T. Sasaki, J. Hazard. Mater. 411 (2021) 125071. doi: 10.1016/j.jhazmat.2021.125071
99. [99]
  J. Jeong, J. Jung, W.J. Cooper, Water Res. 44 (2010) 4391–4398. doi: 10.1016/j.watres.2010.05.054
100. [100]
  I. Velo-Gala, J.J. López-Peñalver, M. Sánchez-Polo, J. Rivera-Utrilla, Chem. Eng. J. 195-196 (2012) 369–376.
101. [101]
  N. Getoff, W. Lutz, Radiat. Phys. Chem. 25 (1985) 21–26.
102. [102]
  S.P. Mezyk, J.R. Peller, S.K. Cole, et al., Ozone Sci. Eng. 30 (2008) 58–64. doi: 10.1080/01919510701761112
103. [103]
  G. Zhao, Y. Pang, L. Liu, J. Gao, B. Lv, J. Hazard. Mater. 179 (2010) 1078–1083. doi: 10.1016/j.jhazmat.2010.03.115
104. [104]
  C. Zwiener, T. Glauner, J. Sturm, M. Worner, F.H. Frimmel, Anal. Bioanal. Chem. 395 (2009) 1885–1892. doi: 10.1007/s00216-009-3098-9
105. [105]
  E. Brillas, C.A. Martínez-Huitle, Appl. Catal. B: Environ. 166-167 (2015) 603–643.
106. [106]
  M. Moura de Salles Pupo, J.M. Albahaca Oliva, K.I. Barrios Eguiluz, G.R. Salazar-Banda, J. Radjenovic, Chemosphere 253 (2020) 126701. doi: 10.1016/j.chemosphere.2020.126701
107. [107]
  X.D. Lv, S.Q. Yang, W.J. Xue, Y.H. Cui, Z.Q. Liu, J. Hazard. Mater. 366 (2019) 250–258. doi: 10.1016/j.jhazmat.2018.11.091
108. [108]
  J. Radjenovic, M. Petrovic, Water Res. 94 (2016) 128–135. doi: 10.1016/j.watres.2016.02.045
109. [109]
  G. Del Moro, C. Pastore, C. Di Iaconi, G. Mascolo, Sci. Total Environ. 506-507 (2015) 631–643.
110. [110]
  O. Turkay, S. Barisci, E. Ulusoy, A. Dimoglo, Water Air Soil Pollut 229 (2018) 170–181. doi: 10.1007/s11270-018-3823-0
111. [111]
  M. Zaghdoudi, F. Fourcade, I. Soutrel, et al., J. Hazard. Mater. 335 (2017) 10–17. doi: 10.1016/j.jhazmat.2017.04.028
112. [112]
  F. Geneste, Curr. Opin. Electrochem. 11 (2018) 19–24. doi: 10.1016/j.coelec.2018.07.002
113. [113]
  C. Lutke Eversloh, N. Henning, M. Schulz, T.A. Ternes, Water Res. 48 (2014) 237–246. doi: 10.1016/j.watres.2013.09.035
114. [114]
  E. Hapeshi, A. Lambrianides, P. Koutsoftas, et al., Environ. Sci. Pollut. Res. Int. 20 (2013) 3592–3606. doi: 10.1007/s11356-013-1605-1
115. [115]
  G.P. Anipsitakis, D.D. Dionysiou, Appl. Catal. B: Environ. 54 (2004) 155–163. doi: 10.1016/j.apcatb.2004.05.025
116. [116]
  M.M. Ahmed, S. Barbati, P. Doumenq, S. Chiron, Chem. Eng. J. 197 (2012) 440–447. doi: 10.1016/j.cej.2012.05.040
117. [117]
  Y. Gao, Z. Zhang, S. Li, et al., Appl. Catal. B: Environ. 185 (2016) 22–30. doi: 10.1016/j.apcatb.2015.12.002
118. [118]
  H.Y. Dong, Z.M. Qiang, J. Hu, C. Sans, Chem. Eng. J. 316 (2017) 288–295. doi: 10.1016/j.cej.2017.01.099
119. [119]
  X.X. Wang, Z.H. Wang, Y.Z. Tang, et al., Chem. Eng. J. 368 (2019) 999–1012. doi: 10.1016/j.cej.2019.02.194
120. [120]
  M.V. Alipázaga, N. Coichev, Anal. Lett. 36 (2003) 2255–2275. doi: 10.1081/AL-120023717
121. [121]
  X. Zhao, W. Wu, Y. Yan, Environ. Sci. Pollut. Res. 26 (2019) 24707–24719. doi: 10.1007/s11356-019-05601-4
122. [122]
  D. Zhou, Y. Yuan, S. Yang, H. Gao, L. Chen, J. Sulfur Chem. 36 (2015) 373–384. doi: 10.1080/17415993.2015.1028939
123. [123]
  J.P. Zhu, Y.L. Lin, T.Y. Zhang, et al., Chem. Eng. J. 367 (2019) 86–93. doi: 10.1016/j.cej.2019.02.120
124. [124]
  W.T. Shang, Z.J. Dong, M. Li, et al., Chem. Eng. J. 361 (2019) 1333–1344. doi: 10.1016/j.cej.2018.12.139
125. [125]
  Y. Gao, W. Fan, Z. Zhang, et al., J. Hazard. Mater. 426 (2022) 128114. doi: 10.1016/j.jhazmat.2021.128114
126. [126]
  T.W. Chan, N.J. Graham, W. Chu, J. Hazard. Mater. 181 (2010) 508–513. doi: 10.1016/j.jhazmat.2010.05.043
127. [127]
  J.A. Khan, X.X. He, N.S. Shah, et al., Chem. Eng. J. 252 (2014) 393–403. doi: 10.1016/j.cej.2014.04.104
128. [128]
  L. Zhou, C. Ferronato, J.M. Chovelon, M. Sleiman, C. Richard, Chem. Eng. J. 311 (2017) 28–36. doi: 10.1016/j.cej.2016.11.066
129. [129]
  Y. Guo, X. Lou, C. Fang, et al., Environ. Sci. Technol. 47 (2013) 11174–11181. doi: 10.1021/es403199p
130. [130]
  Y. Yang, J. Jiang, X. Lu, J. Ma, Y. Liu, Environ. Sci. Technol. 49 (2015) 7330–7339. doi: 10.1021/es506362e
131. [131]
  Y. Mao, H. Dong, S. Liu, L. Zhang, Z. Qiang, Water Res. 173 (2020) 115615. doi: 10.1016/j.watres.2020.115615
132. [132]
  C. Liang, Z.S. Wang, C.J. Bruell, Chemosphere 66 (2007) 106–113. doi: 10.1016/j.chemosphere.2006.05.026
133. [133]
  G.D. Fang, D.D. Dionysiou, D.M. Zhou, et al., Chemosphere 90 (2013) 1573–1580. doi: 10.1016/j.chemosphere.2012.07.047
134. [134]
  F.X. Tian, B. Xu, Y.L. Lin, et al., Water Res. 58 (2014) 198–208. doi: 10.1016/j.watres.2014.03.069
135. [135]
  L. Meng, S. Yang, C. Sun, et al., J. Hazard. Mater. 337 (2017) 34–46. doi: 10.1016/j.jhazmat.2017.05.005
136. [136]
  R. Chahboune, H. Mountacer, M. Sarakha, Rapid Commun. Mass Spectrom. 29 (2015) 1370–1380. doi: 10.1002/rcm.7234
137. [137]
  R.R. Singh, Y. Lester, K.G. Linden, et al., Environ. Sci. Technol. 49 (2015) 2983–2990. doi: 10.1021/es505469h
138. [138]
  S. Giannakis, M. Jovic, N. Gasilova, et al., J. Environ. Manage. 195 (2017) 174–185. doi: 10.1016/j.jenvman.2016.07.004
139. [139]
  J.L. Kormos, M. Schulz, H.P. Kohler, T.A. Ternes, Environ. Sci. Technol. 44 (2010) 4998–5007. doi: 10.1021/es1007214
140. [140]
  F.M. Wendel, C. Lutke Eversloh, E.J. Machek, et al., Environ. Sci. Technol. 48 (2014) 12689–12697. doi: 10.1021/es503609s
141. [141]
  A.R. Becker, L.A. Sternson, Proc. Natl. Acad. Sci. U. S. A. 78 (1981) 2003–2007. doi: 10.1073/pnas.78.4.2003
142. [142]
  X.L. Zou, T. Zhou, J. Mao, X.H. Wu, Chem. Eng. J. 257 (2014) 36–44. doi: 10.1016/j.cej.2014.07.048
143. [143]
  W.S. Chen, C.P. Huang, Chem. Eng. J. 266 (2015) 279–288. doi: 10.1016/j.cej.2014.12.100
1. [1]
  Chi Zhang , Ning Ding , Yuwei Pan , Lichun Fu , Ying Zhang . The degradation pathways of contaminants by reactive oxygen species generated in the Fenton/Fenton-like systems. Chinese Chemical Letters, 2024, 35(10): 109579-. doi: 10.1016/j.cclet.2024.109579
2. [2]
  Huijuan Li , Zhu Wang , Jiagen Geng , Ruiping Song , Xiaoyin Liu , Chaochen Fu , Si Li . Current advances in UV-based advanced oxidation processes for the abatement of fluoroquinolone antibiotics in wastewater. Chinese Chemical Letters, 2025, 36(4): 110138-. doi: 10.1016/j.cclet.2024.110138
3. [3]
  Jinshuai Zheng , Junfeng Niu , Crispin Halsall , Yadi Guo , Peng Zhang , Linke Ge . New insights into transformation mechanisms for sulfate and chlorine radical-mediated degradation of sulfonamide and fluoroquinolone antibiotics. Chinese Chemical Letters, 2025, 36(5): 110202-. doi: 10.1016/j.cclet.2024.110202
4. [4]
  Yaxuan Jin , Chao Zhang , Guigang Zhang . Atomically dispersed low-valent Au on poly(heptazine imide) boosts photocatalytic hydroxyl radical production. Chinese Journal of Structural Chemistry, 2024, 43(12): 100414-100414. doi: 10.1016/j.cjsc.2024.100414
5. [5]
  Nianhua Luo , Jiayi Jiang , Muhammad Suleman , Zhaowen Liu , Shuping Huang , Wei Xiao , Jie Wu , Jiapian Huang . Advances in radical Smiles rearrangement. Chinese Chemical Letters, 2026, 37(2): 111556-. doi: 10.1016/j.cclet.2025.111556
6. [6]
  Zhengzhong Zhu , Shaojun Hu , Zhi Liu , Lipeng Zhou , Chongbin Tian , Qingfu Sun . A cationic radical lanthanide organic tetrahedron with remarkable coordination enhanced radical stability. Chinese Chemical Letters, 2025, 36(2): 109641-. doi: 10.1016/j.cclet.2024.109641
7. [7]
  Jindian Duan , Xiaojuan Ding , Pui Ying Choy , Binyan Xu , Luchao Li , Hong Qin , Zheng Fang , Fuk Yee Kwong , Kai Guo . Oxidative spirolactonisation for modular access of γ-spirolactones via a radical tandem annulation pathway. Chinese Chemical Letters, 2024, 35(10): 109565-. doi: 10.1016/j.cclet.2024.109565
8. [8]
  Xiao-Bo Liu , Ren-Ming Liu , Xiao-Di Bao , Hua-Jian Xu , Qi Zhang , Yu-Feng Liang . Nickel-catalyzed reductive formylation of aryl halides via formyl radical. Chinese Chemical Letters, 2024, 35(12): 109783-. doi: 10.1016/j.cclet.2024.109783
9. [9]
  Hong-Qiang Dong , Shang-Bo Yu , Shu-Meng Wang , Jia-Hao Zhao , Xu-Guan Bai , Shi-Xing Lei , Zhen-Nan Tian , Jia Tian , Kang-Da Zhang , Lu Wang , Zhan-Ting Li , Shigui Chen . Construction of radical halogen-bonded organic frameworks with enhanced magnetism and conductivity. Chinese Chemical Letters, 2025, 36(8): 110730-. doi: 10.1016/j.cclet.2024.110730
10. [10]
  Hui-Xian Jiang , Zhi-Tao Liu , Pei Xu , Xu Zhu . Synthetic application of oxalate salts for visible-light-induced radical transformations. Chinese Chemical Letters, 2025, 36(12): 111224-. doi: 10.1016/j.cclet.2025.111224
11. [11]
  Saima Perveen , Lulu Qin , Min Zhao , Zhengwei Ding , Yingying Wang , Zaicheng Nie , Pengfei Li . Recent development in radical cycloaddition reactions for the synthesis of carbo- and heterocycles. Chinese Chemical Letters, 2026, 37(1): 111886-. doi: 10.1016/j.cclet.2025.111886
12. [12]
  Quan Xu , Ye-Qing Du , Pan-Pan Chen , Yili Sun , Ze-Nan Yang , Hui Zhang , Bencan Tang , Hong Wang , Jia Li , Yue-Wei Guo , Xu-Wen Li . Computation assisted chemical study of photo-induced late-stage skeleton transformation of marine natural products towards new scaffolds with biological functions. Chinese Chemical Letters, 2025, 36(5): 110141-. doi: 10.1016/j.cclet.2024.110141
13. [13]
  Jing-Qi Tao , Shuai Liu , Tian-Yu Zhang , Hong Xin , Xu Yang , Xin-Hua Duan , Li-Na Guo . Photoinduced copper-catalyzed alkoxyl radical-triggered ring-expansion/aminocarbonylation cascade. Chinese Chemical Letters, 2024, 35(6): 109263-. doi: 10.1016/j.cclet.2023.109263
14. [14]
  Wei Zhou , Xi Chen , Lin Lu , Xian-Rong Song , Mu-Jia Luo , Qiang Xiao . Recent advances in electrocatalytic generation of indole-derived radical cations and their applications in organic synthesis. Chinese Chemical Letters, 2024, 35(4): 108902-. doi: 10.1016/j.cclet.2023.108902
15. [15]
  Yu-Yu Tan , Lin-Heng He , Wei-Min He . Copper-mediated assembly of SO₂F group via radical fluorine-atom transfer strategy. Chinese Chemical Letters, 2024, 35(9): 109986-. doi: 10.1016/j.cclet.2024.109986
16. [16]
  Yuhan Liu , Jingyang Zhang , Gongming Yang , Jian Wang . Highly enantioselective carbene-catalyzed δ-lactonization via radical relay cross-coupling. Chinese Chemical Letters, 2025, 36(1): 109790-. doi: 10.1016/j.cclet.2024.109790
17. [17]
  Xiaoling WANG , Hongwu ZHANG , Daofu LIU . Synthesis, structure, and magnetic property of a cobalt(Ⅱ) complex based on pyridyl-substituted imino nitroxide radical. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 407-412. doi: 10.11862/CJIC.20240214
18. [18]
  Shaofeng Gong , Zi-Wei Deng , Chao Wu , Wei-Min He . Stabilized carbon radical-mediated three-component functionalization of amino acid/peptide derivatives. Chinese Chemical Letters, 2025, 36(5): 110936-. doi: 10.1016/j.cclet.2025.110936
19. [19]
  Chonglong He , Yulong Wang , Quan-Xin Li , Zichen Yan , Keyuan Zhang , Shao-Fei Ni , Xin-Hua Duan , Le Liu . Alkylarylation of alkenes with arylsulfonylacetate as bifunctional reagent via photoredox radical addition/Smiles rearrangement cascade. Chinese Chemical Letters, 2025, 36(5): 110253-. doi: 10.1016/j.cclet.2024.110253
20. [20]
  Xiang Li , Beibei Zhang , Zhixiang Wang , Xiangyu Chen . Organocatalyzed iodine-mediated reversible-deactivation radical polymerization via photoinduced charge transfer complex catalysis. Chinese Chemical Letters, 2025, 36(6): 110383-. doi: 10.1016/j.cclet.2024.110383

Get Citation

PDF

XML

Metrics

PDF Downloads(18)
Abstract views(2410)
HTML views(221)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142