Skip to main content
Log in

Degradation of diethyl phthalate (DEP) by vacuum ultraviolet process: influencing factors, oxidation products, and toxicity assessment

  • Research Article
  • Published:
Environmental Science and Pollution Research Aims and scope Submit manuscript

Abstract

The vacuum ultraviolet (VUV) process, which can directly produce hydroxyl radical from water, is considered to be a promising oxidation process in degrading contaminants of emerging concern, because of no need for extra reagents. In this study, the influencing factors and mechanism for degradation of diethyl phthalate (DEP) by the VUV process were investigated. The effects of irradiation intensity, inorganic anions, natural organic matter (NOM), and H2O2 dosage on the performance of VUV process were evaluated. The results showed that DEP could be more efficiently degraded by the VUV process compared with ultraviolet (UV)-254-nm irradiation. The presence of HCO3, NO3 and NOM in the aqueous solutions inhibited the degradation of DEP to a different degree, mainly by competing hydroxyl radicals (HO) with DEP. Degradation rate and removal efficiency of DEP by VUV process significantly enhanced with the addition of H2O2, while excess H2O2 dosage could inhibit the DEP degradation. Moreover, based on the identified seven oxidation byproducts and their time-dependent evolution profiles, a possible pathway for DEP degradation during the VUV process was proposed. Finally, the ecotoxicity of DEP and its oxidation byproducts reduced overall according to the calculated results from Ecological Structure Activity Relationships (ECOSAR) program. The electrical energy per order (EE/O) was also assessed to analysis the energy cost of the DEP degradation in the VUV process. Our work showed the VUV process could be an alternative and environmental friendly technology for removing contaminants in water.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  • Aleboyeh A, Olya ME, Aleboyeh H (2008) Electrical energy determination for an azo dye decolorization and mineralization by UV/H2O2 advanced oxidation process. Chem Eng J 137:518–524

    Article  CAS  Google Scholar 

  • Augusto O, Bonini MG, Amanso AM, Linares E, Santos CCX, De Menezes SL (2002) Nitrogen dioxide and carbonate radical anion: two emerging radicals in biology. Free Radic Biol Med 32:841–859

    Article  CAS  Google Scholar 

  • Bajt O, Mailhot G, Bolte M (2001) Degradation of dibutyl phthalate by homogeneous photocatalysis with Fe (III) in aqueous solution. Appl Catal B Environ 33:239–248

    Article  CAS  Google Scholar 

  • Bao Y, Sun X, Sun X, Hu J (2011) Mechanism of OH-initiated atmospheric oxidation of diethyl phthalate. Can J Chem 89:1419–1427

    Article  CAS  Google Scholar 

  • Bodzek M, Dudziak M, Luks-Betlej K (2004) Application of membrane techniques to water purification. Removal of phthalates. Desalination 162:121–128

    Article  CAS  Google Scholar 

  • Bu L, Zhou S, Shi Z, Deng L, Li G, Yi Q, Gao N (2016) Degradation of oxcarbazepine by UV-activated persulfate oxidation: kinetics, mechanisms, and pathways. Environ Sci Pollut Res 23:2848–2855

    Article  CAS  Google Scholar 

  • Bu L, Zhou S, Shi Z, Bi C, Zhu S, Gao N (2017) Iron electrode as efficient persulfate activator for oxcarbazepine degradation: performance, mechanism, and kinetic modeling. Sep Purif Technol 178:66–74

    Article  CAS  Google Scholar 

  • Bu L, Zhou S, Zhu S, Wu Y, Duan X, Shi Z, Dionysiou DD (2018) Insight into carbamazepine degradation by UV/monochloramine: reaction mechanism, oxidation products, and DBPs formation. Water Res 146:288–297

    Article  CAS  Google Scholar 

  • Chen W-L, Sung H-H (2005) The toxic effect of phthalate esters on immune responses of giant freshwater prawn (Macrobrachium rosenbergii) via oral treatment. Aquat Toxicol 74:160–171

    Article  CAS  Google Scholar 

  • Chen N, Fang G, Zhou D, Gao J (2016) Effects of clay minerals on diethyl phthalate degradation in Fenton reactions. Chemosphere 165:52–58

    Article  CAS  Google Scholar 

  • Crittenden JC, Hu S, Hand DW, Green SA (1999) A kinetic model for H2O2/UV process in a completely mixed batch reactor. Water Res 33:2315–2328

    Article  CAS  Google Scholar 

  • de Oliveira TF, Chedeville O, Cagnon B, Fauduet H (2011) Degradation kinetics of DEP in water by ozone/activated carbon process: influence of pH. Desalination 269:271–275

    Article  CAS  Google Scholar 

  • Gómez-Hens A, Aguilar-Caballos MP (2003) Social and economic interest in the control of phthalic acid esters. TrAC Trends Anal Chem 22:847–857

    Article  CAS  Google Scholar 

  • Gonzalez MG, Oliveros E, Wörner M, Braun AM (2004) Vacuum-ultraviolet photolysis of aqueous reaction systems. J Photochem Photobiol C: Photochem Rev 5:225–246

    Article  CAS  Google Scholar 

  • Han W, Zhang P, Zhu W, Yin J, Li L (2004) Photocatalysis of p-chlorobenzoic acid in aqueous solution under irradiation of 254nm and 185nm UV light. Water Res 38:4197–4203

    Article  CAS  Google Scholar 

  • Jobling S, Reynolds T, White R, Parker MG, Sumpter JP (1995) A variety of environmentally persistent chemicals, including some phthalate plasticizers, are weakly estrogenic. Environ Health Perspect 103:582–587

    Article  CAS  Google Scholar 

  • Latini G (2005) Monitoring phthalate exposure in humans. Clin Chim Acta 361:20–29

    Article  CAS  Google Scholar 

  • Lei Y, Zhu C, Lu J, Zhu Y, Zhu M, Chen T, Peng S (2018) Photochemical reaction kinetics and mechanisms of diethyl phthalate with N (III) in the atmospheric aqueous environment. J Photochem Photobiol A Chem 362:21–30

    Article  CAS  Google Scholar 

  • Liao Q-N, Ji F, Li J-C, Zhan X, Hu Z-H (2016) Decomposition and mineralization of sulfaquinoxaline sodium during UV/H2O2 oxidation processes. Chem Eng J 284:494–502

    Article  CAS  Google Scholar 

  • Medellin-Castillo NA, Ocampo-Pérez R, Leyva-Ramos R, Sanchez-Polo M, Rivera-Utrilla J, Méndez-Díaz JD (2013) Removal of diethyl phthalate from water solution by adsorption, photo-oxidation, ozonation and advanced oxidation process (UV/H2O2, O3/H2O2 and O3/activated carbon). Sci Total Environ 442:26–35

    Article  CAS  Google Scholar 

  • Moussavi G, Rezaei M (2017) Exploring the advanced oxidation/reduction processes in the VUV photoreactor for dechlorination and mineralization of trichloroacetic acid: parametric experiments, degradation pathway and bioassessment. Chem Eng J 328:331–342

    Article  CAS  Google Scholar 

  • Moussavi G, Pourakbar M, Shekoohiyan S, Satari M (2018) The photochemical decomposition and detoxification of bisphenol A in the VUV/H2O2 process: degradation, mineralization, and cytotoxicity assessment. Chem Eng J 331:755–764

    Article  CAS  Google Scholar 

  • Muruganandham M, Swaminathan M (2004) Photochemical oxidation of reactive azo dye with UV–H2O2 process. Dyes Pigments 62:269–275

    Article  CAS  Google Scholar 

  • Na S, Jinhua C, Cui M, Khim J (2012) Sonophotolytic diethyl phthalate (DEP) degradation with UVC or VUV irradiation. Ultrason Sonochem 19:1094–1098

    Article  CAS  Google Scholar 

  • Oh BS, Jung YJ, Oh YJ, Yoo YS, Kang J-W (2006) Application of ozone, UV and ozone/UV processes to reduce diethyl phthalate and its estrogenic activity. Sci Total Environ 367:681–693

    Article  CAS  Google Scholar 

  • Staples CA, Peterson DR, Parkerton TF, Adams WJ (1997) The environmental fate of phthalate esters: a literature review. Chemosphere 35:667–749

    Article  CAS  Google Scholar 

  • Sun J, Bu L, Deng L, Shi Z, Zhou S (2018) Removal of Microcystis aeruginosa by UV/chlorine process: inactivation mechanism and microcystins degradation. Chem Eng J 349:408–415

    Article  CAS  Google Scholar 

  • Sung H-H, Kao W-Y, Su Y-J (2003) Effects and toxicity of phthalate esters to hemocytes of giant freshwater prawn, Macrobrachium rosenbergii. Aquat Toxicol 64:25–37

    Article  CAS  Google Scholar 

  • Swan SH (2008) Environmental phthalate exposure in relation to reproductive outcomes and other health endpoints in humans. Environ Res 108:177–184

    Article  CAS  Google Scholar 

  • Tan C, Gao N, Deng Y, Zhang Y, Sui M, Deng J, Zhou S (2013) Degradation of antipyrine by UV, UV/H2O2 and UV/PS. J Hazard Mater 260:1008–1016

    Article  CAS  Google Scholar 

  • Tay KS, Madehi N (2015) Ozonation of ofloxacin in water: by-products, degradation pathway and ecotoxicity assessment. Sci Total Environ 520:23–31

    Article  CAS  Google Scholar 

  • Vamseekrishna C, Phale PS (2008) Bacterial degradation of phthalate isomers and their esters. Indian J Microbiol 48:19–34

    Article  CAS  Google Scholar 

  • Wang AQ, Xu B, Zhang TY, Chen YY, Gao NY (2017) Effect of UV irradiation and UV/chlorine processes on trichloronitromethane formation during chlorination of ronidazole. Clean-Soil Air Water 45:1600163

  • Wang Z, Shao Y, Gao N, Lu X, An N (2018) Degradation of diethyl phthalate (DEP) by UV/persulfate: An experiment and simulation study of contributions by hydroxyl and sulfate radicals. Chemosphere 193:602–610

    Article  CAS  Google Scholar 

  • Wen D, Wu Z, Tang Y, Li M, Qiang Z (2018) Accelerated degradation of sulfamethazine in water by VUV/UV photo-Fenton process: impact of sulfamethazine concentration on reaction mechanism. J Hazard Mater 344:1181–1187

    Article  CAS  Google Scholar 

  • Xie P, Yue S, Ding J, Wan Y, Li X, Ma J, Wang Z (2018) Degradation of organic pollutants by vacuum-ultraviolet (VUV): kinetic model and efficiency. Water Res 133:69–78

    Article  CAS  Google Scholar 

  • Xu B, Gao N-Y, Sun X-F, Xia S-J, Rui M, Simonnot M-O, Causserand C, Zhao J-F (2007) Photochemical degradation of diethyl phthalate with UV/H2O2. J Hazard Mater 139:132–139

    Article  CAS  Google Scholar 

  • Yao H, Pei J, Wang H, Fu J (2017) Effect of Fe (II/III) on tetracycline degradation under UV/VUV irradiation. Chem Eng J 308:193–201

    Article  CAS  Google Scholar 

  • Yin N, Liang S, Liang S, Hu B, Yang R, Zhou Q, Jiang G, Faiola F (2018) DEP and DBP induce cytotoxicity in mouse embryonic stem cells and abnormally enhance neural ectoderm development. Environ Pollut 236:21–32

    Article  CAS  Google Scholar 

  • Yuan SY, Liu C, Liao CS, Chang BV (2002) Occurrence and microbial degradation of phthalate esters in Taiwan river sediments. Chemosphere 49:1295–1299

    Article  CAS  Google Scholar 

  • Zhang D, Wu L, Yao J, Herrmann H, Richnow H-H (2018) Carbon and hydrogen isotope fractionation of phthalate esters during degradation by sulfate and hydroxyl radicals. Chem Eng J 347:111–118

    Article  CAS  Google Scholar 

  • Zhou S, Xia Y, Li T, Yao T, Shi Z, Zhu S, Gao N (2016) Degradation of carbamazepine by UV/chlorine advanced oxidation process and formation of disinfection by-products. Environ Sci Pollut Res 23:16448–16455

    Article  CAS  Google Scholar 

  • Zoschke K, Dietrich N, Börnick H, Worch E (2012) UV-based advanced oxidation processes for the treatment of odour compounds: efficiency and by-product formation. Water Res 46:5365–5373

    Article  CAS  Google Scholar 

  • Zoschke K, Börnick H, Worch E (2014) Vacuum-UV radiation at 185 nm in water treatment – a review. Water Res 52:131–145

    Article  CAS  Google Scholar 

Download references

Funding

This work was financially supported by the National Natural Science Foundation (51508174), the Fund of State Key Laboratory of Pollution Control and Resource Reuse (PCRRF17023), and the Natural Science Foundation of Hunan Province (2018JJ3059).

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Lin Deng or Shiqing Zhou.

Additional information

Responsible editor: Vítor Pais Vilar

Electronic supplementary material

ESM 1

(DOCX 71 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Wu, Y., Deng, L., Bu, L. et al. Degradation of diethyl phthalate (DEP) by vacuum ultraviolet process: influencing factors, oxidation products, and toxicity assessment. Environ Sci Pollut Res 26, 5435–5444 (2019). https://doi.org/10.1007/s11356-018-3914-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11356-018-3914-x

Keywords

Navigation