Elucidation of the last steps of photo-ammonification: analytical method development and mechanism elucidation

doi:10.1007/s11783-024-1860-z

Front. Environ. Sci. Eng.

2024, Vol. 18

Issue (8) : 100 https://doi.org/10.1007/s11783-024-1860-z

Elucidation of the last steps of photo-ammonification: analytical method development and mechanism elucidation

Yingjing Miao¹, Hui Wang²(

), Chunpeng Yang², Ruochun Zhang³, Hao Zhang³, Peizhe Sun¹(

)

¹. School of Environmental Science and Engineering, Tianjin University, Tianjin 300072, China
². SINOPEC Research Institute of Petroleum Processing Co., Ltd., Beijing 100083, China
³. School of Earth System Science, Tianjin University, Tianjin 300072, China

Download: PDF(1811 KB) HTML
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks

Abstract

● A new method was developed for simultaneous quantification of multiple NOCs.

● The final steps in the photo-ammonification of NOCs were elucidated.

● This method is less susceptible to organic interference.

The mechanisms underlying the photo-ammonification of nitrogenous organic compounds (NOCs) remain unclear, partly due to the analytical challenges of small NOC intermediates. This study introduced a simple methodology for accurately and simultaneously quantifying multiple small NOCs during ammonification processes. The developed method employed phenyl isothiocyanate as derivatization reagents, followed by high-performance liquid chromatography analysis to measure primary and secondary amines, amides, as well as NH₄⁺ over variable photo-ammonification conditions. In our experimental setup, vacuum ultraviolet (VUV) irradiation serves as the controlled reaction environment to simulate harsh photo-ammonification environment. Representative NOCs, including pyridine, N,N-dimethylformamide, and acrylonitrile, were chosen due to their structural diversity and environmental relevance as model NOCs. This method was able to achieve excellent nitrogen mass balance, and revealed that the last steps of photo-ammonification involved oxidation of nitrogen-adjacent carbon to amide followed by the cleavage of N–C bond. This novel method may also help quantitative investigation of nitrogen transformations in different environmental contexts.

Keywords Ammonification NOCs Amines Nitrogen mass balance

Corresponding Author(s): Hui Wang,Peizhe Sun

Issue Date: 11 July 2024

Cite this article:

Yingjing Miao,Hui Wang,Chunpeng Yang, et al. Elucidation of the last steps of photo-ammonification: analytical method development and mechanism elucidation[J]. Front. Environ. Sci. Eng., 2024, 18(8): 100.

URL:

https://academic.hep.com.cn/fese/EN/10.1007/s11783-024-1860-z
https://academic.hep.com.cn/fese/EN/Y2024/V18/I8/100

Fig.1 Proposed PITC derivatization mechanisms and structures of target compounds.

Fig.2 Standard curves of (a) NH₄⁺, (b) MA and (c) DMA derivatives and (d) ammonia production in standards after peptidase hydrolysis at room temperature (Initial concentration: 100 µmol/L; time of hydrolysis: 30 min).

Fig.3 Transformation of nitrogen (NH₄⁺, MA, DMA, amides TN and TNadd) and C/C₀ (initial concentration: 1 mmol/L) over photon fluence under VUV irradiation at pH 7.2. (a) PYD; (b) DMF; (c) AN; (d) proposed photo-ammonification intermediates. Note: TNadd values were computed by summing the measured quantities of PYD/DMF/AN, MA, DMA, amides and NH₄⁺. TN values were determined by alkaline potassium persulfate digestion method.

1	E S A Badr, E P Achterberg, A D Tappin, S J Hill, C B Braungardt. (2003). Determination of dissolved organic nitrogen in natural waters using high-temperature catalytic oxidation. Trends in Analytical Chemistry, 22(11): 819–827 https://doi.org/10.1016/S0165-9936(03)01202-0
2	G Bhojani, S Jani, N K Saha. (2022). Facile biodegradation of N,N-dimethylformamide, N,N-dimethylacetamide and N-methyl-2-pyrrolidone by source-derived Bacillus strain APS1 for water reclamation and reuse. Journal of Cleaner Production, 334: 130098 https://doi.org/10.1016/j.jclepro.2021.130098
3	J A Camargo, Á Alonso. (2006). Ecological and toxicological effects of inorganic nitrogen pollution in aquatic ecosystems: a global assessment. Environment International, 32(6): 831–849 https://doi.org/10.1016/j.envint.2006.05.002
4	T A Doane. (2017). The abiotic nitrogen cycle. ACS Earth & Space Chemistry, 1(7): 411–421 https://doi.org/10.1021/acsearthspacechem.7b00059
5	W B Fortune, M G Mellon. (1938). Determination of iron with o-phenanthroline: a spectrophotometric study. Industrial & Engineering Chemistry. Analytical Edition, 10(2): 60–64 https://doi.org/10.1021/ac50118a004
6	C P Funkey, R J Latour, D A Bronk. (2015). Abiotic effects on effluent dissolved organic nitrogen along an estuarine transect. Water Environment Research, 87(3): 258–265 https://doi.org/10.2175/106143014X14062131178231
7	M Hosomi, R Sudo. (1986). Simultaneous determination of total nitrogen and total phosphorus in freshwater samples using persulfate digestion. International Journal of Environmental Studies, 27(3–4): 267–275 https://doi.org/10.1080/00207238608710296
8	J Huang, N R Kankanamge, C Chow, D T Welsh, T Li, P R Teasdale. (2018). Removing ammonium from water and wastewater using cost-effective adsorbents: a review. Journal of Environmental Sciences, 63: 174–197 https://doi.org/10.1016/j.jes.2017.09.009
9	V Kitidis, G Uher, E M S Woodward, N J P Owens, R C Upstill-Goddard. (2008). Photochemical production and consumption of ammonium in a temperate river–sea system. Marine Chemistry, 112(1–2): 118–127 https://doi.org/10.1016/j.marchem.2008.07.005
10	L Leng, S Xu, R Liu, T Yu, X Zhuo, S Leng, Q Xiong, H Huang. (2020). Nitrogen containing functional groups of biochar: an overview. Bioresource Technology, 298: 122286 https://doi.org/10.1016/j.biortech.2019.122286
11	D Li, X Xu, Z Li, T Wang, C Wang. (2020). Detection methods of ammonia nitrogen in water: A review. Trends in Analytical Chemistry, 127: 115890 https://doi.org/10.1016/j.trac.2020.115890
12	M Li, Z Qiang, P Hou, J R Bolton, J Qu, P Li, C Wang. (2016). VUV/UV/chlorine as an enhanced advanced oxidation process for organic pollutant removal from water: assessment with a novel mini-fluidic VUV/UV photoreaction system (MVPS). Environmental Science & Technology, 50(11): 5849–5856 https://doi.org/10.1021/acs.est.6b00133
13	S Liu, J Han, Y Ding, X Gao, H Cheng, H Wang, C Liu, A Wang. (2022). Advanced reduction process to achieve efficient degradation of pyridine. Chemosphere, 287: 132240 https://doi.org/10.1016/j.chemosphere.2021.132240
14	L Long, Y Yang, S You, L Wei, B Chen. (2022). Using formaldehyde as a novel chemical actinometer for 185 nm vacuum ultraviolet photon flux quantification in water. Journal of Photochemistry and Photobiology A: Chemistry, 432: 114080 https://doi.org/10.1016/j.jphotochem.2022.114080
15	Q Man, P Zhang, W Huang, Q Zhu, X He, D Wei. (2022). A heterotrophic nitrification-aerobic denitrification bacterium Halomonas venusta TJPU05 suitable for nitrogen removal from high-salinity wastewater. Frontiers of Environmental Science & Engineering, 16(6): 69
16	M J Palys, H Wang, Q Zhang, P Daoutidis. (2021). Renewable ammonia for sustainable energy and agriculture: vision and systems engineering opportunities. Current Opinion in Chemical Engineering, 31: 100667 https://doi.org/10.1016/j.coche.2020.100667
17	D Pang, L Qiu, Y Wang, R Zhu, F Ouyang. (2015). Photocatalytic decomposition of acrylonitrile with N–F codoped TiO2/SiO2 under simulant solar light irradiation. Journal of Environmental Sciences-China, 33: 169–178 https://doi.org/10.1016/j.jes.2015.01.017
18	A Rain-Franco, C Muñoz, C Fernandez. (2014). Ammonium production off central Chile (36 S) by photodegradation of phytoplankton-derived and marine dissolved organic matter. PLoS One, 9(6): e100224 https://doi.org/10.1371/journal.pone.0100224
19	M A Sutton, J W Erisman, F Dentener, D Möller. (2008). Ammonia in the environment: from ancient times to the present. Environmental Pollution, 156(3): 583–604 https://doi.org/10.1016/j.envpol.2008.03.013
20	A V Vähätalo, M Järvinen. (2007). Photochemically produced bioavailable nitrogen from biologically recalcitrant dissolved organic matter stimulates production of a nitrogen-limited microbial food web in the Baltic Sea. Limnology and Oceanography, 52(1): 132–143 https://doi.org/10.4319/lo.2007.52.1.0132
21	Y Wang, Y Zhang, X Zhu, Y Liu, Z Wu. (2022). Fluorine-induced oxygen vacancies on TiO2 nanosheets for photocatalytic indoor VOCs degradation. Applied Catalysis B: Environmental, 316: 121610 https://doi.org/10.1016/j.apcatb.2022.121610
22	P J Worsfold, P Monbet, A D Tappin, M F Fitzsimons, D A Stiles, I D McKelvie. (2008). Characterisation and quantification of organic phosphorus and organic nitrogen components in aquatic systems: a review. Analytica Chimica Acta, 624(1): 37–58 https://doi.org/10.1016/j.aca.2008.06.016
23	X Xing, N Li, D Liu, J Cheng, Z Hao. (2022). Effect of Cu-ZSM-5 catalysts with different CuO particle size on selective catalytic oxidation of N,N-Dimethylformamide. Frontiers of Environmental Science & Engineering, 16(10): 125
24	G Yang, H Xu, Y Luo, S Hei, G Song, X Huang. (2023). Novel electro-assisted micro-aerobic cathode biological technology induces oxidative demethylation of N,N-dimethylformamide for efficient ammonification of refractory membrane-making wastewater. Journal of Hazardous Materials, 442: 130001 https://doi.org/10.1016/j.jhazmat.2022.130001
25	Y Yang, P Sun, L P Padhye, R Zhang. (2021). Photo-ammonification in surface water samples: mechanism and influencing factors. Science of the Total Environment, 759: 143547 https://doi.org/10.1016/j.scitotenv.2020.143547
26	Y Zhang, L Chang, N Yan, Y Tang, R Liu, B E Rittmann. (2014). UV photolysis for accelerating pyridine biodegradation. Environmental Science & Technology, 48(1): 649–655 https://doi.org/10.1021/es404399t
27	Y Zhang, R Zhang, S L Li, K M G Mostofa, X Fu, H Ji, W Liu, P Sun. (2021). Photo-ammonification of low molecular weight dissolved organic nitrogen by direct and indirect photolysis. Science of the Total Environment, 764: 142930 https://doi.org/10.1016/j.scitotenv.2020.142930
28	Y Zhang, H Zhang, X Dong, D Yue, L Zhou. (2022). Effects of oxidizing environment on digestate humification and identification of substances governing the dissolved organic matter (DOM) transformation process. Frontiers of Environmental Science & Engineering, 16(8): 99

[1]

FSE-24043-OF-MYJ_suppl_1

Download

[1]	Hallvard Ødegaard. A road-map for energy-neutral wastewater treatment plants of the future based on compact technologies (including MBBR)[J]. Front. Environ. Sci. Eng., 2016, 10(4): 2-.
[2]	Zhaoyi SHEN,Zhuo CHEN,Zhen HOU,Tingting LI,Xiaoxia LU. Ecotoxicological effect of zinc oxide nanoparticles on soil microorganisms[J]. Front. Environ. Sci. Eng., 2015, 9(5): 912-918.
[3]	Chengkun WANG, Xiaojian ZHANG, Jun WANG, Chao CHEN. Detecting N-nitrosamines in water treatment plants and distribution systems in China using ultra-performance liquid chromatography-tandem mass spectrometry[J]. Front Envir Sci Eng, 2012, 6(6): 770-777.
[4]	Yongji ZHANG, Lingling ZHOU, Guo ZENG, Huiping DENG, Guibai LI. Impact of total organic carbon and chlorine to ammonia ratio on nitrification in a bench-scale drinking water distribution system[J]. Front Envir Sci Eng Chin, 2010, 4(4): 430-437.

Viewed

Full text

Abstract

Cited

Shared

Discussed