Influence of Solution pH on Photolysis Intermediates and DegradationPathway of Diazinon during UV Irradiation Treatment

doi:10.6023/A15070520

Acta Chim. Sinica ›› 2015, Vol. 73 ›› Issue (11): 1196-1202.DOI: 10.6023/A15070520 Previous Articles Next Articles

Article

溶液pH值对二嗪磷紫外光降解产物及降解途径的影响

刘玉灿, 段晋明, 李伟

西安建筑科技大学环境与市政工程学院西安 710055

投稿日期:2015-07-30 发布日期:2015-09-15
通讯作者: 段晋明 E-mail:jinmingduan@xauat.edu.cn
基金资助:
项目受国家自然科学基金(No. 51308437)和陕西省教育厅基金(No. 2013JK0980)资助.

Influence of Solution pH on Photolysis Intermediates and DegradationPathway of Diazinon during UV Irradiation Treatment

Liu Yucan, Duan Jinming, Li Wei

School of Environmental & Municipal Engineering, Xi’an University of Architecture and Technology, Xi’an 710055

Received:2015-07-30 Published:2015-09-15
Supported by:
Project supported by the National Natural Science Foundation of China (No. 51308437) and the Foundation of Shaanxi Educational Committee of China (2013JK0980).

1. Influence of Solution pH on Photolysis Intermediates and DegradationPathway of Diazinon during UV Irradiation Treatment.PDF(918KB)

Abstract

The direct photolysis of an organophosphorus pesticide, diazinon, was investigated under monochromatic ultraviolet (UV) irradiation (253.7 nm) at different solution pH. Photolysis was conducted in an annular photochemical reactor, in the axis of which a low-pressure mercury UV lamp was installed. The photon flux into the solution from the UV lamp was determined to be at 1.18×10^-7 Einstein·s^-1. A magnetic stirrer was located at the bottom of the reactor to maintain homogeneity of the reacting solution. A thermostatic water recirculation system was used to control the solution temperature at 20±0.5 ℃. Prior to photolysis, the UV lamp was ignited for 30 min for a stable output. UV photolysis was performed with ultrapure water containing an initial 5 mg/L diazinon. Solution pH (4.0, 7.0 and 10.0) was buffered using 2 mmol/L phosphate and/or borate buffers. The analyses of diazinon and its UV photo-degradation intermediates were conducted by using ultra-performance liquid chromatography-electrospray-tandem mass spectrometry (UPLC-ESI-MS/MS) coupled with an ACQUITY^TM UPLC BEH C8 separation column. Full-scan spectra were acquired from 50 to 500 m/z in both positive electrospray ionization (ESI+) mode and negative electrospray ionization (ESI-) mode. To obtain further information for analyzing the structure of UV photo-degradation intermediates of diazinon, collision induced dissociation (CID) experiments were also conducted. The collision energy for each intermediate was optimized in the range from 15 to 35 eV. Argon was used as collision gas and its flow rate was at 0.12 mL/min. The results show that solution pH affected significantly on the photo-degradation rate of diazinon. The rate was lower at acidic pH 4 (the pseudo-first-order rate constant (k) is 0.0193 min^-1) than those at neutral and alkaline pH values of 7.0 and 10.0 (k=0.0234 min^-1 and k=0.0236 min^-1, respectively). More than 90% of diazinon were degraded within 120 minutes of UV irradiation at all the three pH values. The photolysis intermediates of diazinon were found to vary with solution pH. There are 5, 8, and 6 major species of photolysis intermediates for diazinon after 60 minutes of UV irradiation in water at pH of 4.0, 7.0 and 10.0, respectively. Moreover, the amount of a certain intermediate formed was very different under different pH conditions. A systematic qualitative and quantitative analyses of the photo-degradation intermediates of diazinon under different pH conditions were conducted. The molecular structure of the intermediates were deduced based on the information of mass spectrometry; the photo-degradation pathways of diazinon under different pH conditions were also proposed.

Key words: diazinon, pH, ultraviolet, photolysis intermediates, degradation pathway

Cite this article

Liu Yucan, Duan Jinming, Li Wei. Influence of Solution pH on Photolysis Intermediates and DegradationPathway of Diazinon during UV Irradiation Treatment[J]. Acta Chim. Sinica, 2015, 73(11): 1196-1202.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Baldwin, C. J. Sustainability in the Food Industry, Wiley-Blackwell, Ames, 2011.
[2] Schwarzenbach, R. P.; Escher, B. I.; Fenner, K.; Hofstetter, T. B.; Johnson, C. A.; Gunten, U. V.; Wehrli, B. Science 2006, 313, 1072.
[3] Mitra, A.; Chatterjee, C.; Mandal, F. B. Res. J. Environ. Toxicol. 2011, 5, 81.
[4] Rathore, H. S.; Nollet, L. M. Pesticides: Evaluation of Environmental Pollution, CRC, Florida, 2012.
[5] Kolpin, D. W.; Thurman, E. M.; Linhart, S. M. Sci. Total Environ. 2000, 248, 115.
[6] Schiff, K.; Sutula, M. Environ. Toxicol. Chem. 2004, 23, 1815.
[7] Wang, X.; Liu, Z.; Jia, F.; Zhang, Q.; Yin, J.; Liu, Y. Acta Chim. Sinica 2011, 69, 2505. (王雪荣, 刘振波, 贾风燕, 张强, 殷军港, 刘永明, 化学学报, 2011, 69, 2505.)
[8] Shemer, H.; Linden, K. G. J. Hazard. Mater. 2006, 136, 553.
[9] Banks, K. E.; Hunter, D. H.; Wachal, D. J. Sci. Total Environ. 2005, 350, 86.
[10] Zhang, Y.; Hou, Y.; Chen, F.; Xiao, Z.; Zhang, J.; Hu, X. Chemosphere 2011, 82, 1109.
[11] Dubus, I. G.; Hollis, J. M.; Brown, C. D. Environ. Pollut. 2000, 110, 331.
[12] Albanis, T. A.; Hela, D. G.; Sakellarides, T. M.; Konstantinou, I. K. J. Chromatogr. A 1998, 823, 59.
[13] Bailey, H. C.; Deanovic, L.; Reyes, E.; Kimball, T.; Larson, K.; Cortright, K.; Connor, V.; Hinton, D. E. Environ. Toxicol. Chem. 2000, 19, 82.
[14] Bailey, H. C.; Krassoi, R.; Elphick, J. R.; Mulhall, A. M.; Hunt, P.; Tedmanson, L.; Lovell, A. Environ. Toxicol. Chem. 2009, 19, 72.
[15] Wei, X.; Chen, J.; Xie, Q.; Zhang, S.; Ge, L.; Qiao, X. Environ. Sci. Technol. 2013, 47, 4284.
[16] Ge, L.; Chen, J.; Wei, X.; Zhang, S.; Qiao, X.; Cai, X.; Xie, Q. Environ. Sci. Technol. 2010, 44, 2400.
[17] Trapp, S.; Franco, A.; Mackay, D. Environ. Sci. Technol. 2010, 44, 6123.
[18] Rendal, C.; Kusk, K. O.; Trapp, S. Environ. Toxicol. Chem. 2011, 30, 2395.
[19] Bilski, P.; Martinez, L. J.; Koker, E. B.; Chignell, C. F. Photochem. Photobiol. 1996, 64, 496.
[20] Wang, Y.; Shi, X. Acta Chim. Sinica 2014, 72, 682. (王媛, 石晓燕, 化学学报, 2014, 72, 682.)
[21] Wei, X.; Chen, J.; Xie, Q.; Zhang, S.; Li, Y.; Zhang, Y.; Xie, H. Environ. Sci.: Processes Impacts 2015, 17, 1220.
[22] Ku, Y.; Chang, J. L.; Cheng, S. C. Water. Air, Soil Pollut. 1998, 108, 445.
[23] Boreen, A. L.; Arnold, W. A.; McNeill, K. Aquat. Sci. 2003, 65, 320.
[24] Gómez, M. J.; Sirtori, C.; Mezcua, M.; Fernández-Alba, A. R.; Agüera, A. Water Res. 2008, 42, 2698.
[25] Evgenidou, E.; Konstantinou, I.; Fytianos, K.; Albanis, T. J. Hazard. Mater. 2006, 137, 1056.
[26] Souza, A. G.; Cardeal, Z. L.; Augusti, R. J. Environ. Sci. Health., Part B 2013, 48, 171.
[27] Sharpless, C. M.; Linden, K. G. Environ. Sci. Technol. 2001, 35, 2949.
[28] Moussavi, G.; Hossaini, H.; Jafari, S. J.; Farokhi, M. J. Photochem. Photobiol. A 2014, 290, 86.
[29] Mansour, M.; Feicht, E. A.; Behechti, A.; Schramm, K. W.; Kettrup, A. Chemosphere 1999, 39, 575.
[30] Sarathy, S.; Mohseni, M. Water Res. 2010, 44, 4087.
[31] Kouloumbos, V. N.; Tsipi, D. F.; Hiskia, A. E.; Nikolic, D.; Van Breemen, R. B. J. Am. Soc. Mass Spectrom. 2003, 14, 803.
[32] Ibáñez, M.; Hernández, F.; Pozo, Ó. J.; Sancho, J. Anal. Bioanal. Chem. 2006, 384, 448.
[33] ?olovi?, M.; Krsti?, D.; Petrovi?, S.; Leskovac, A., Joksi?, G.; Savi?, J. Toxicol. Lett. 2010, 193, 9.
[34] Cox, J. R.; Ramsay, O. B. Chem. Rev. 1964, 64, 317.
[35] Muecke, W.; Alt, K. O.; Esser, H. E. J. Agric. Food Chem. 1970, 18, 208.
[36] Bailey, H. C.; Kraddoi, R.; Elphick, J. R.; Mulhall, A. M.; Hunt, P.; Tedmanson, L.; Lovell, A. Environ. Toxicol. Chem. 2000, 19, 72.
[37] Rahn, R. O.; Stefan, M. I.; Bolton, J. R.; Goren, E.; Shaw, P.; Lykke, K. R. Photochem. Photobiol. 2003, 78, 146.
[38] Lau, T. K.; Chu, W.; Graham, N. Chemosphere 2005, 60, 1045.

溶液pH值对二嗪磷紫外光降解产物及降解途径的影响

Influence of Solution pH on Photolysis Intermediates and DegradationPathway of Diazinon during UV Irradiation Treatment

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Cheng-Qiang Wang, Chao Feng. Applications of Nucleophilic Fluorine Sources in the Selective Fluorofunctionalization of Unsaturated Carbon-Carbon Bonds [J]. Acta Chimica Sinica, 2024, 82(2): 160-170.
[2]	Jinglin Yi, Mao Chen. Photo-Induced Copolymerization of Chlorotrifluoroethylene and Methyl Isopropenyl Ether^★ [J]. Acta Chimica Sinica, 2024, 82(2): 126-131.
[3]	Jianqiang Chen, Gangguo Zhu, Jie Wu. Recent Advances in Nickel-Catalyzed Ring Opening Cross-Coupling of Aziridines [J]. Acta Chimica Sinica, 2024, 82(2): 190-212.
[4]	Yuqing Shi, Mingzhu Chu, Bo Han, Haojie Ma, Ran Li, Xueyan Hou, Yuqi Zhang, Ji-Jiang Wang. Smart Two-dimensional Photonic Crystal Hydrogel for Accurate Detection of Hg²⁺ [J]. Acta Chimica Sinica, 2024, 82(1): 9-15.
[5]	Ruxin Zeng, Peng R. Chen. RNA-Binding Proteome Analysis and Functional Explorations^★ [J]. Acta Chimica Sinica, 2024, 82(1): 53-61.
[6]	Zhiqiang Wang, Jinzhan Su. Investigation of the Kinetic Properties and Photoelectrochemical Water Splitting of Cu₃V₂O₈/ZnO Photoanode Modified by Cobalt Phosphate [J]. Acta Chimica Sinica, 2024, 82(1): 26-35.
[7]	Chenyu Liao, Shanwei Guo, Meiwei Huang, Yong Guo, Qing-Yun Chen, Chao Liu, Yunwen Zhang. Synthesis and Properties of Fluoroether Phosphocholine [J]. Acta Chimica Sinica, 2024, 82(1): 46-52.
[8]	Yuchun Han, Yilin Wang. Retrospect and Prospect of Long-lasting Antibacterial Materials^★ [J]. Acta Chimica Sinica, 2023, 81(9): 1196-1201.
[9]	Jiao Kong, Lin Du, Xiangyang Li, Jidong Zhu, Ya-Qiu Long. Small Molecule Degraders Targeting the SHP2^E76A Mutant Effectively Inhibiting the Proliferation of Wild-type and Mutant SHP2 Dependent Tumor Cells [J]. Acta Chimica Sinica, 2023, 81(9): 1120-1128.
[10]	Yuhan Wu, Dongdong Zhang, Hongyu Yin, Zhengnan Chen, Wen Zhao, Yuhua Chi. Density Functional Theory Study of Janus In₂S₂X Photocatalytic Reduction of CO₂ under “Double Carbon” Target [J]. Acta Chimica Sinica, 2023, 81(9): 1148-1156.
[11]	Ye Tian, Duanhui Si, Shuiying Gao, Rong Cao. Ultra-Long Organic Room Temperature Phosphorescence of Phthalic Acid Derivative Modified Polymer^★ [J]. Acta Chimica Sinica, 2023, 81(9): 1129-1134.
[12]	Fengjie Ge, Kaizhi Zhang, Qingpeng Cao, Hui Xu, Tao Zhou, Wenhao Zhang, Xinxin Ban, Xiaobo Zhang, Na Li, Peng Zhu. Design, Synthesis and Electroluminescence Performance of Flexible Fluorenyl Block Delayed Fluorescence Dimers [J]. Acta Chimica Sinica, 2023, 81(9): 1157-1166.
[13]	Peng Tao, Xiaokang Zheng, Guoliang Wang, Xinghao Sheng, He Jiang, Wentao Li, Jibiao Jin, Sui-Hung Wong, Yanqin Miao, Hua Wang, Wai-Yeung Wong. Novel Bipolar Orange Emissive Iridium(III) Complexes: Design, Synthesis, and Electroluminescence^★ [J]. Acta Chimica Sinica, 2023, 81(8): 891-897.
[14]	Di Yang, Xiaofan Shi, Jijie Zhang, Xian-He Bu. Recent Research Progress and Prospect of Photothermal Materials in Seawater Desalination^★ [J]. Acta Chimica Sinica, 2023, 81(8): 1052-1063.
[15]	Yuan Zhang, Beining Zheng, Meichun Fu, Shouhua Feng. Research Progress in the Application of Spinel Oxides in Tumor Therapy^★ [J]. Acta Chimica Sinica, 2023, 81(8): 949-954.