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    Advanced Oxidation Processes For The Removal of Organophosphorus Pesticides in Aqueous Matrices - A Systematic Review and Meta-Analysis - Elsevier Enhanced Reader

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    Process Safety and Environmental aecion 134 (2020) 292-307 Contents lists available at ScienceDirect Journal homepage: www.elsevier.com/locatelpsep Process Safety and Environmental Protection IChemE 2 Advanced oxidation processes for the removal of organophosphorus ® pesticides in aqueous matrices: A systematic review and a, meta-analysis Mohammad Malakootian*”, Armita Shahesmaeili‘, Maryam Faraji**°, Hoda Amiri", Susana Silva Martinez''** 2 nvionmentl at EnsinringRsarch Cntr. Kerman ivr of Mec Scenes Kero. ran ® Denroment of Ertonmentat Health Stoo Pui Hath eran Ov of Medial Sees Kean «HVS Surelne Research Cmte an WHO Colaba Center for IV Survellance. sae fr Fares Stacesn Heth Kerman University of | Mri! cee forma, on Gorrie nia eras Apia. A: Unies 100, ol Champ, Cran Mor, Mey ARTICLE INFO ABSTRACT ari sen “The advanced oxidation processes(AOPS). a5 an alternative technology to eliminate pesticides rom aque- Received 24 gus 2019 ous environments, canst of several groups af tetnolgis that have been used with high ein in Received in revise orm the treatment of water and wastewater in recent decades A systematic review ofthe scientific literature Ree toevaluate the most common advanced oxidation processes(AOPs)for the removal oforganophosphorus ees pesteesinaqucos mates sadaressedinhsstudy, Mets amlyss soe erormedkoprovdea pre fis and robust summary estimate after asystematie and rigorous integration of the available evidence —— Inthe curent study, su-qeoups of ADPs Were reviewed, sch as electrochemical, UV|H20, phoolsis, no photocstalyis Fenton-type, plasms, gamma radiation, sulfte-base catalyst sonal an ozonation a Technology for organophosphorus pesticides degradation. The random effects model wae used to esi Netwanls imate he pooled measurements and 95% confidence interval (95 Cn toa sixstdies were included Pests inthis review. Al studies except one, used the photocatalytic process as ADP. The average pooled pe Remesistion centage of AOP for pesticide degradation was 66.8 (95 % CI: 58.1-75.). In adlition, the most sted Saitama Pesticides ae chlorpyrifos and diazinon which, according to the results of he meta-analysis, the photo- Eatalytic process has the highest efficiency of diazinon elimination with an average percentage of 79.2 (95 %CL 768-815) 1© 2019 Institution of Chemical Engineers. Published by Elsevier BV. All rights reserved, Contents 1. Introduction. 2. Chemical structure ofthe organophosphorus compounds 3. Methodology. BAe Daa secs and seach state 32. Statistical analysis 4. Results 41. Study selection 42. Degradation of organophosphorus pesticides by AOPS 424, Electrochemical processes. 422. _UViHa02 photolysis process 423. Photocatalytic eatment 424, Homogeneous and heterogeneous Fenton ype processes. responding autor at: Department of Environmental Healt, School of Public Health, Kerman Univers of Medical cence, Kerman an, + corresponding autora: Centro de nvestgain en Ingenta yClenclas Apcaas Av Universidad 1001, Col Chara Cuesnavaa, Morelos, Meco, smal address da amin@gmalcom(H- Armin sivadusemmx (sa Mariner) utpsdi.org/10.1016)sep2019.12008 (0957-5820/6 2019 asituion of Chemica Engines, Published by Elsevier B.A ight reserved, 293 293 293 293 293 204 295 296 297 297 1M Mokooon eal oes Safety and Enianmentalotetion 134 (2020) 292-207 an 425, Plasma technology 299 426. Gamma tradiation technology 302 42.7. Sullate-based catalyst. “302 428 Sonolysis 303 429. Ozone based AOPS. 303 42.10. Other AOPS. 308 43, Meta-analysis 308 5. Conclusions 305 Acknowledgement 306 References 306 1. Introduction 3. Methodology Pesticides area widespread group of chemicals used to improve agricultural production and home care, However, these compounds ‘can be classified into a category of persistent organic pollutants that remain in water for a long time, accumulate in sediments or ‘bioaccumulate in biota, are transferred over long distances or have toxic effects to the environment, human health and living organ- isms even in low concentrations. Said classification i based on the solubility and Log Kow (a measure oftheir hydrophobicity)of these ‘compounds, People are exposed to pesticides through consump- tion of contaminated drinks, food and other environmental media (Katsikantami etal, 2019), Organophosphorus pesticides, the most common pesticides, account for 34 % of world sales which according to the published Papers chlorpyrifos, diazinon, malathion, parathion and phorate are the most prevalent in the environment (Amiri et al, 2018; Katsikantami etal, 2019: Khedr et al, 2019; Naddaf etal, 2018), To reduce the potential health risks, the AOPS are an alterna- tive technology to remove pesticides from the environment. They are non-selective processes for the removal of organic pollutants, by producing oxidizing radical species (eg, H, Op-", 03-", OH, tc.) capable of degrading and mineralizing contaminants in CO2, H,0 and inorganies (Jaafarzadeh et al. 2014; Mahvi et al, 2011; Yaghmaeian etal, 2016) ‘Although, the literature shows some priority in the tendency to use AOPS for the degradation of organophosphotus pesticides in recent years, it seems that processes such as photocatalysis (Amiri et al, 2018; Naddafi et al, 2018; Toolabi et al, 2019), Fenton and electto-Fenton (Dominguez etal, 2018) radiation (UV, gamma and (ozone) (Bustos etal, 2019; Cruz-Alcalde etal 2018; Khedr etal, 2019) and persulfate based AOP (Liu et al, 2019) are the most recently used tecinnology forthe elimination of organophosphorus pesticides, This review, although by no means exhaustive, presents a sys- tematic review of the literature to evaluate the most common advanced oxidation processes used forthe removal of organophos- phorus pesticides in aqueous media. n addition, a meta-analysis is ‘carried our to provide a precise and robust summary estimate after a systematic and rigorous integration of the available evidence. To the best of our knowledge, we are the first to use meta-analysis 0 investigate this subject. 2. Chemical structure of the organophosphorus compounds Organophosphorus compounds (OP) contain a. pentavalent phosphorus atom with a double bond to either oxygen (PO) or Sulphur (P=S). The chemical structures of OP and common OP are shown in Fig. 1 (Kang et al, 1995) X is the leaving group with structures ranging from a single halogen atom to a complex sub- stituted aryl ring Ballantyne and Marrs, 2017) and is the principal metabolite fora specific identification (Kazemi et al, 2012). 3.1. Data sources and search strategy A systematic search of the peer-reviewed literature was car- ried out in the Web of science and Science direct databases as scientific articles that evaluated the oxidation processes for the ‘eatment of aqueous solution contaminated with pesticides. In the systematic review, we searched articles that were published until January 27,2019, The search included the keywords [(Advance oxi- dation process) OR (AOP)] AND (organophosphorus pesticide) AND ((wvater) OR (wastewater) OR (aqueous) OR (agriculture runoff) AND [(treatment) OR (removal) OR (decomposition) OR (degra- dation) OR (mineralization), The literature search was limited to peer-reviewed publications written in English between 2010 until January 2019. After this stage, we considered a set of inclusion and. exclusion criteria, whieh are described below: The study inclusion criteria apply to each publication, which consists of scope (Step 1), study quality (Step 2), and data availabil- ity (Step 3). For Step 1, two independent screeners first evaluated the titles and abstracts of the retrieved articles to assess whether the paper included organophosphorus pesticides removal using AOPS in aqueous solution. In addition, the full text of the papers ‘whose abstracts passed the frst screening step to confirm thatthe document contained an experimental study to evaluate the eff ciency of the organophosphorus pesticide oxidation process. We excluded books, presentations, review papers, and letter tothe ed {or about AOPS for the removal of organophosphorus pesticides and other environmental matrices such as soil and air. Also, papers about the development of detection methods of organophospho- tus pesticides in lfferent media were excluded. Information on teach paper was extracted, such as the fist author, year of publi- cation, type of pesticide, type of oxidation process, response factor for the evaluation of the efficiency of the AOP and optimum pH For Step 2, the quality ofa study was evaluated independently by ‘wo scientific reviewers. Te studies have passed the criteria ofclar~ ity. Publicationsin which thei study and associated methodologies ‘were not sufficiently documented to investigate the quality of the study were not included. After a publication passed both scope and quality criteria, the availability of the data (step 3) was analyzed. For this selection step, a requirement was that the publications include experimental design through the use of different software, and the available answers imply the mean and standard deviation, of data, 3.2, Statistical analysis To calculate the combined percentage of AOP efficiency for ‘the removal of organophosphorus pesticides, studies designed by response surface methodology (RSM) entered the meta-analysis. In studies with multiple executions, the average removal percentage {or all executions was calculated, The pooled estimate was calcu- Jated using the ietangommand in the Stata software Version 14 aa -M.Molaootan ares Safty and Entonnenta Protection 1262020) 252-307 (O-alkyl phosphorothioate Phosphorodithioate S-alkyl phosphorothioate S-alkyl phosphorodithioate Phosphoramidate Phosphorotriamidate Phosphorothioamidate Phosphorus group General structure ‘Common pesticides Phosphaie ° Chlorfenvinphos, Dhlorvos nov} o-x R-0- Phosphonate Butonate,Trchlorfon Roy n-o-? Phosphonothioate ‘ ‘Trichlormat, Cyanofenphos rot toeP—o—x i Rong aoa tee i Ro. SP—S—K ao i Ros. ox Ro Rosa l Sp—0-K r—o-P ° RON R—o-P NS | Rea N a RR 4 R R—0—P—NC ian S.alky! ° Ron k n—o-P NR Demeton-S-methyl, Vamidothion Bromophos, Chlorpyrifos, Diazinon Dimethoate, Disulfoton, Malathion Profenofos, Tritenofos Prothiofes, Sulprofos Cruformate, Fenamifos ‘Triamifos Methamidofos Isofenfos Fig Structures or organophosphorus compounds common used 2 pesticides. ‘The random effects model was used to estimate the pooled mea~ 4. surements and 95 % confidence intervals (95 % Cl). The subgroup analysis was performed only in groups with at least two studies, ‘The forest digammas were used to show the results of the meta- analysis. All analyzes were performed with STATA version 15.0, (STATA Corp, College Station, Texas, USA). Results 4.1. Study selection In recent years, a growing number of publications have been. devoted (0 the study of the treatment of pesticides by oxida- 1M Mokooon eal oes Safety and Enianmentalotetion 134 (2020) 292-207 i ic Le I | | i ° zoo 21923013 Beles aoe 27012 Time yes Fig 2. Number of publctos daring test decaein the Webfeed (46) tive techniques and AOPs (Fig 2). The classification of published srs papers according fo the AOPS used, the aqueods matrices and = se the organophosphorus pesticides are shown in Fig. The study = tre selection considered four stages, sich as identification, screening | “revs eligibility and inclusion of the dacuments. Thus in the fst step = ‘omen athe selection procedure, 335 records were identified as shown = = im the PRISMA flow-diagtam of Fic. Sixty duplicates and 221 =p Soo ttn records were removed because they didnot meet the incusion ——o pee, criteria (they were not published in English, were review articles, ——e me encyclopedia, book chapters, conference summary. mini reviews, mo news, short communications and others, so the eiibility of 54 7 7 a 7 Studies was evaluated Inthe third step identincationo edundan- Peis ee : ies among the fll text papers that wil be evaluated to determine their eligibility), 8 studies were excluded and 46 were included im the qualitative synthesis. Therefore, 6 stdies were identified pores for inclusion in the meta-analysis after the selection process was completed ce 8 2 oe a eSecondry Wastewater 42. Degradation of organophosphorus pesticides by AOPS Pal pf organophospt Pes ‘by. =p tydroxyl radicals (OH) are the most poverful oxidants (ox- EE EE) dation potential of 2.72) and are responsibie forthe degradation ee) ‘of most organic pollutants in water. The degradation of aqueous ‘organic compounds mainly depends on the amount of hydroxyl radicals produced through different AOPs. Many other oxidant species are produced in the AOPS in addition to OH" radicals, such 8 superoxide radical anions (O2~"), hydroperoxy! radical (HOp" hydrogen peroxide (H202), solvated electrons (e-), hydrogen radi- cals (H'), amongst others According to the literature, the possible degradation mecha- nism of organophosphorus pesticides involves the formation of hydroxylated intermediates (a mixture of non-retained species ‘of high polarity such as phosphate derivatives) as the first step In the AOPs, followed by the formation of aliphatic compounds after bond-breaking reactions (Dzyadevych and Chovelon, 2002; Guivarch et al, 2003; Herrmann et a, 1999). The products of ring ‘opening, and side chain breaking might be alcohols, aldehydes or ketones, which will be oxidized to carboxylic acids and mineralized 10 CO) and H,0 (Guivarch et al. 2003; Herrmann et al, 1989), This section reports the findings of the degradation of ‘organophosphorus pesticides using different AOPs, such as elec ‘ochemical, UV/H,02 photolysis, photocatalysis, Fenton-type, plasma, gamma irradiation, sulfate-based catalyst, sonalysis and ‘ozonation technology. a . sie sy ae TE cote TT © 0 3 0 ts ig 3. Classification of published papex(percent) based onthe ADPS studied water matics (8) and organophosphorus pesticides -M.Molaootan ares Safty and Entonnenta Protection 1262020) 252-307 Records identified through database searching (a=285) ‘Additional records identified through othe sources (n=50) ‘dentifeation | Records afer duplicates removed (0-275) i ei Records sercened Reconds excluded (=i) | (=) Pollen articles assessed for Pall text articles excluded, e ligibitiy [+] with reasons n= 8) (a-sd) 3 & Studies included in qualitative synthesis (n= 46) + Included Studies included in ‘quantitative synthesis (meta analysis) @=6) Fig 4. The PRSMA flowchart of the seach and section of papers. 42.1, Electrochemical processes ‘The electrochemical methods produce hydroxyl radicals using direct or indirect electrochemical oxidation technologies. These techinologies include electrochemical, sonoelectrochemical and Photoelectrochemical processes and involve surface and bulk oxi- dation processes. Different electrochemical processes have been used to study the degradation of pesticides such as chlorpyrifos, slyphosate, karbofos (malathion), bazudin (diazinon),chlorophos, etaphos and thiamethoxam in aqueous solutions with a wide range of initial concentrations at laboratory scale. Table | includes the experimental conditions, the kinetics and the degree of degra- dation ofthe pesticides mentioned above. Samet ang collaborators, studied the anodic oxidation of chlorpyrifos at NbjPbO2 electrode using bulk electrolysis (Samet et al, 2010} These investigators ‘observed an increase in the chemical oxygen demand (COD) removal by increasing the apparent current density from 10 10 50mA cnr? because more OH. were generated: however, the instantaneous current efficiency (ICE) dropped to zero with pro- longed electrolysis, since a large part ofthese radicals was wasted, Which hampered the complete mineralization. A 76 % of COD removal was achieved at 10h of electrolysis under the best experi- ‘mental conditions. in addition, they observed that even the ICE fell ‘when the oxidation of chlorpyrifos took place in diluted solutions (Samet etal, 2010). The degradation of chlorpyrifos was effectively improved by the combination of electrolysis with sonolysis (US- EC) using common stainless-steel electrodes. Ren and co-workers reported a synergistic factor of 37 % compared to the treatments, fof US and EC (Ren et al, 2019). In addition, other organophospho- ‘us compounds, such as glyphosate, karbofos (malathion), bazudin, (Giazinon), chlorophos and metaphos were also evaluated by the electrochemical process (Kukurina et al, 2014), These authors reported that the commercial pesticides have lower electroly= sis efficiency compare to the analytical grade purity. This was attributed to the presence of bulkier materials (e.g. dyestuffs, sur~ face active agents and talc) in commercial pesticide products. In general, according to COD data and phosphate ion accumulation, it was estimated that pesticides were completely destroyed fol- lowing pseudo first order kinetics (Kukurina et al, 2014). Finally, thiamethoxam (TMX) degradation over a boron-doped diamond (BOD) anode was investigated by Lebik-Flhadi and co-workers. They studied the effect of different operating parameters, such, as inital pollutant concentration, current intensity, presence of ‘humic acid, bicarbonate and chlorine on TMX degradation kinetics. In addition, the degradation and mineralization of TMX in a teal ‘water matrix was observed. According to their results, the CICo ratio in different aqueous matrices followed the order: wastew= 1M Mokooon eal oes Safety and Enianmentalotetion 134 (2020) 292-207 aor Tablet ‘Summary ofthe optimal conditions ofthe electrochemical processes forthe emovalidegradtion of pesticides and kinetic data Pesticide Trial concentration and ‘oP eares Tine daa erence hlrpysies COD=450:mg 0; Lt inaqucous _Niobiam|ND/PRO, electrodes, preudo second (Gamera, 2010) solution pi, oer kinetics, Removal r-0°¢ Somnem? hrpyitos soomgL—1in aqueous solution lecrde inthe EC=stainlee-steet Removalefficiency (Benet at 2019) combine with ClyphotateKarofos———_chlowophos=37gL-1 lected nthe BC= Lead Resnovalefcieney (ohare at, (Matathion, Bazin 2014) (iazinon) chron, Metaphas Metapos= catent desiy=12 Alem? (2400), Sag Lt inpolluced aqueous hlropos= sulfuric cde solutions Metapios =9957:¢ “Tiamechoxam 1aimgt-t in pure wares, Heceochemicl boron doped pseudo onder inete Secondary teated wastewater, damond anode bosted water pues ater photolysis process UVjt,0» photolysis is a process in which organophosphorus, ‘compounds absorb photons and the energy released drives oxi- dation processes induced by light. Some organic compounds can be reduced by photolysis alone, The reduction of organophospho- rus compounds, such as those reported in Table 2, i aided by the addition of hydrogen peroxide to generate hydroxyl radicals in an ‘advanced oxidation process. “Table 2 reports the degradation of parathion, chlorpyrifos (CPF), fensulfothion, diazinon and malathion by H202/UV photolysis in aqueous solutions. Wu and co-workers (Wu and Linden, 2010) ‘examined the influence of anions such as bicarbonate and car- bonate on the hydroxyl radical production in the UV/}H202 process dose affected UV-oxidation byproducts speciation which altered DBPS formation, The DBP formation increased significantly in the ‘eated diazinon solutions with UV irradiation (Li et al, 2015). In addition, four main UV oxidation byproducts [2-isopropyl- _methyl-4-pyrimidinol (IMP), O-analog diazinon (diazoxon), diethyl thiophosphate (DETP) and diethyl phosphate (DEP)] were exam- ined to identify their relative contributions t DBPs formation ‘The increase in total DBPs formation of the treated diazinon solu- tions was attributed mainly to its oxidation product IMP and its secondary oxidation products, while DETP and DEP had lit- tle effect. Moreover. its oxidation fragment diazoxon intensified the formation of MCA, DCAA and TCA under UV/H)0> pre- oxidation condition, Malathion was another pesticide treated with the HO/UV process (Chenna eta, 2016). twas reported that the photodegradation of malathion was more effective for higher val- ‘ues of pH and temperature and its degradation kinetics was a fist ‘order reaction The ecotoxicity and phytotoxicity of the aqueous solutions treated before and after the oxidative process was a considerable factor in selecting the AOP process (Utzig et.al, 2019). Inthis regard, several scientists preferred the UV/H202 and UVC radiation pro- cesses for the oxidation of CPF, and the efficiency ofthe treatment ‘was evaluated considering the acute toxicity of the Aedes aegypti larvae and the seed germinationj root elongation test with Lactuca ‘sativa seeds. The results showed that, although both processes were efficient, showing a reduction of over 97 % of initial CP after 20 and 60min of UV}20> and UVC radiation, respectively, toxicity could increase and lead to larvae mortality (> 90 % of organisms) and inhibition effects on seed root growth (Utzig eta, 2019). 423. Photocatalytic treatment The elimination of organophosphorus pesticides in the photo- catalytic process takes place on the catalyst surface upon chemical reactions produced between the oxidant species (valence band holes -I--, OH", O)~", Hp02, etc.) and the organophosphorus pes- ticides in the wastewater. Such oxidizing species are generated in the process of catalyst activation with adequate light irradia tion. In general, the complexity of the photocatalytic process leads to the consideration of several operational factors, such as pH, concentration of catalyst or oxidant, light intensity and substrate 208 -M.Molaootan ares Safty and Entonnenta Protection 1262020) 252-307 Tabled ‘Summary ofthe UVIH02 photolysis process fo the removallegradation of pesticides Pes Tn conentation and ‘OP estes inte data Reference Parthion (Para), Paea=5 uM LUVIH:0, bylow-pressurelig second-order ate constants (Wand linden, ‘Chlorpyes( CPF) lamps 2010), (PF-3-5yMinaqueous luton pH? Fensulocion 15 10-4mot dm 3 Pulses HOS 90 Fensifrhion moval photolysis (amin) tn aqueous solution pa Neutat “83 TOC vemoval(80-ia) Diainon Smgl—1 Photochemical ractorwitha __psewdafistoxder degradation (eal. 2015) low-pressure mercury UV amp aed 1645 uM in aqueous solution pH=47.10, Maltion 10-100 mgL-1 in demineralized Staicreactorwithalow pressure 1.0%removalofMalation under (Chennact al, water optimal onion 2016) mercury vapor amp First order reaction pues. Chlorpyeits 200ygL-1inaqucous solution Aborosllcte reactor witha high UVIH0>=97% (Uzi etal. 2019) pressure Mercury vapor lamp wwe-97% pisNewal ovate Yamal“ in aqueous solution TO) wo LV-365 nm amps Phorite removal (GOmin}=90% —(Wuet al, 2010) as. Tis dsage0.1 gL! pseudo first-order nets pis Dimethoate 100m LUvinatiation=Tis/polymer fins Dimethoste removal (Prva eval, 2011) Inaaueous solution 70, dosage 4g"! (80min) ~ 00% pusasz ToC mineralization (Go0min)~ 50% Gehloroncotincckd——«S12402 gL ‘O,+UWA poycheomatie Fistonder kinetics (@avar etal, 2011) (Gena) Avorescent amps Using double delonzed water pl'=423 001 oC mineralization (120min) = 46-27 Fenamiphos mgt in teaching water 2inconde(2n0}+ 10s tngsten 70> 10; P25 Degussa (999%)> (Female 31,2012), (i oxide Woy and tin (WV) onde (S00) Neutral Sunlight solar ‘le plant (parabolic eallector (crc). paz pueB2 ‘oy Anatase (09.76) 2110; anatasesutle(1:3(99.4) < 10s (6802) « Sn02 (5.18) ) 25) sing aqueous slution catalyst dosage cP and CPF removal (60 mia) = one tet pies caboreyets 2stma! “ings synthetic slareadation Removal efciency (Cin and Sus, ‘sing acenay pond reactor (RPE) 1991) Inaqueous sluion dosage of 0, (17.07 mgL*) (65.15 in}=71.09410% neutral pH Chloris 27AmaL" inapricukure ———TO3* symteresolrradation —_Remoralefcency (Aoi eta, 2018) ce heracoro cybexane (HCH) malathion and oF 25.6-ichloro-2-pedinl ‘ace Meth parton (MP) and parathion PA) cstamipeld Diainon Diarinon ranoft some! ‘aqueous station some! Inaqueous sluion Mngt in ceal watery stiles water 2assmgl! ‘aqueous slution zomg? in aqueous station ome" ‘n aqueous slution sina RPR dosage of 50, (572m) evra pH FHC +Sumighe porocatalst dose (251mg) etal pH Inmebised To, + UVA (315-4008) pian LW Cie vec photolysis) and [WV-2n0 nanocrystal dosage of 740 = 160.51"! pice? ‘,Fes04S10»nanocompasite (50mg) pers V(I25W}+ 200-710; (05a) peer LUV(125191 + Co-dpedZn0 (o5aL") peer (625 ein) -s400% Removal efceney (2m) -s401, malathion (95%) < FD 2) < HCH (90°) ‘TeP removal (120min radiation) 10%, corde ‘oncentation=266m-! Removal efciency W 200290 and Fenton's reagent Methyl parathion ~ 90% pH3 Toc “75% HozFes04 cs) Chlorpyetes, (F-80856 = 100mg LUVFenton pretreatment combined Removaleficency of W Fenton (amet al, 2014) permet, with aero (coma Chlorotlont ypermetirin Sequencing atch restorSBR) _COD=648% 105752 100mg, Chlorothalont pes Toc=459% 02084 100mg 00 Huo, :coD2) Removal efcency of 318003 100mg1-) Huds Fe 25:1) UV Fenton san ADE oc ‘operation at 12h HRT) 296003 100, cop=062% mgt? Soccaras inPesticile wastewater hlorenvinphos(CFVE) 288 10-4 Mindrnkingwater___Fenton in batch reactor crv removal (Olveraetat, etworks contaminated wt CFVP 2014) Hdr-15.102M (omin)~10% Fe'=46 10M Hoy Fesdy =326:1 pies Tine “Taacophos 2omgL-inaquecus solution __Hycdynamic cavitation dpsed stoner rate Tazophos—(Copate and Patil, Fenoa's reagent esol 120m. 2015) Dreseure= Shar Inyo aviation (0°) < Inydodyamicevtaton and Fenton “83 2) pe hyodynamic tation zonation min) Hs FeS04 =: {azopos.~100% ToC=96%) Diasinon SomgL-inaqueous olution Sono-Fetonand Sono-Fentn-like pseudo frs-orderrateDiatinon_(Wangand Shih, systems emoal (min. 25) titasonc probe ‘tacound (frequency 20K) ‘asound Fe and Fe zonal! ‘tasound “HO HO: 150mg, T-25°¢ (257% pass Uieasund+Fencon Diasinon=98.3% -mineraization=209% aw -M.Molaootan ares Safty and Entonnenta Protection 1262020) 252-307 Tables. ‘Summary ofthe plasma water ecology forthe removallesradation of pesticides Pes Tn conentation and ‘OP estes iesies References ‘Avazine,chorenvinfos,_Avazie'Smgl) Chlorfeavinfos Now thermal plasma, DBD plasma istovder deyadaton Metis, (sa: Valero 2-dlvomophenol, and reactor eal 2013) lindane Gag”, arch reactor removal ficiency (min. 24-dbramopheno 4-dbomophenol (88) < Gmgt-”. Chorenvintos Lindane (943) e Atrazine (93.2) < (gin iste wate Liniane (36.6%) Dinette 200ml in aqueous solution removalefceney Tain} <96% —_(euetal, 2013) distances Sam Dichlorvos, malathion, Dichlorvs Da plasma, frst onder nets, (Sarangapani etl ‘edsuan| 2016), (850 ppd, malathion sow Removal ficiency (ia (2320pb)-endosulfan Aichlorvos 7898-1081) 5, malathion (69524014) endosulan(57-7 2058) (350 6) in aqueous sluion Tabtes. ‘Summary ofthe gamma radiation technology fr the removalderadation of pesticides. Pestide Tait conentation and ‘OP estes Tetce Tefrences MatucSeale hors 5-20mgl- iaDistiled water) Cabal gamma vadlaton and CPF removal efcleney Gessner al, bee water suighe 2013) rae 12 days using sunlgh (CPF 20mg) pit-Neutsal Take water (51.95%) distilled water 303 2, 12 key wing gamma (CeF-5img-")(-1008) hooves 500 ngL-Tinaqueous olution Cabal 60gamma nadlaton. dose pseudoistorder.cPFremoval _(smalletal.2013) sste(3006yh"") eMhcieny (absorbed dose of 575Gy) 100% (Table 5(H1u etal, 2013), Degradation of dichlorvos by DBD plasma ‘was higher than that of malathion and endosulfan (Sarangapani et al, 2016). 42.6, Gamma irradiation technology ‘The irradiation of water molecules by gamma rays produces mainly the OH" radicals in addition to salvated electrons (@5q”) hhydrogen radicals (H"), superoxide radical anions (0,-"),hydroper- ‘oxy! radical (H0,"), hydrogen peroxide (H,O2) and hydrogen (Hy ‘Gamma radiation has proven more effective for the treatment of aqueous contaminants than other methods because hydroxyl rad- icals can easily form. In addition, gamma irradiation can remove ‘organophosphorus pesticides at low concentrations (Khedr et al, 2019), Hossain and coworkers (Hossain et al. 2013) compared ‘gamma iadiation and natural sunlight forthe oxidation of chlor~ Pytifos in aqueous solutions. According to their findings, Table 6 ‘gamma-ray irradiation could be used in combination with con- ventional sunlight methods to degrade environmental samples ‘contaminated with the organophosphate pesticide such as chlor- Pytifos. Although the degradation of chlorpyrifos using sunlight took a long time (12 days), it was more efficient compared 10 ‘gamma irradiation with high energy consumption. In a similar study, Ismail and coworkers (Ismail et al..2013) used gamma irra- dlation to study the removal efficiency of chlorpyrifes in aqueous solution by 60Co c-rays on a laboratory scale. These authors con- firmed that the application of radiation technology could be an effective method t0 destroy water chlorpyrifos (Table 6), In fact, the concentration of chlorpyrifos was reduced from 500 yg L" 10 below the detection timit (5 pg L) of the analytical method in erated Solutions at an absorbed dase of 575.y. 422. Sulfate-based catalyst Persulfate activation can be initiated by thermal or chemical ‘means to form sulfate radicals, SO,"~. The sulfate radical is a stronger oxidant (E°~2.6V) than the persulfate anion. Molybde- ‘num disulfide (MoS) is a catalyst that, due to its special features such as large surface area and catalytically active sites, attracts ‘great attention in the AOPs. In addition, MoS, has a narrow band, gap that improves absorption of visible light and electron-hole pairs upon light excitation, which makes it a candidate for pho- tocatalytic applications under visible light. Aimer et al. (Aimer cet al, 2019) studied the removal efficiency of dimethoate (DIM), an organophosphorus pesticide, by both sulfate radicals of heat= activation of persulfate (PS) and hydroxyl radicals produced by electro-oxidation using a BDD anode, as shown in Table 7. The removal efficiency using PS was higher than that of the DIM electro-oxidation process. However, the BODs/COD ratio during the electrochemical oxidation of DIM via hydroxyl radicals showed that it was possible to render the solution biodegradable with- ‘out reaching a complete mineralization. Fenitrotiion is a common, ‘organophosphorus pesticide that was completely removed by PS activation by zero-valent iron powder (Fe®). Fe? enhanced the (degradation process and reduced the energy barrier during the ‘degradation of pollutants using PS (Lit etal, 2019) (Table 7). 1M Mokooon eal oes Safety and Enianmentalotetion 134 (2020) 292-207 a Table ‘Summary of lfte-based catalyst forthe removalderadation of pests. Pesticide Trial concentration and ‘oP eares Tine daa References imatoate (DIM) ‘G1 mA inSyutbetic wastewater beat activation PS elec iM eemoval eins (Cereal, 2019) ciation Tan (Comin jonas] -1/50) 100 eco oxidation 120 min, Stoo Fentrohion (1) omgL and 20ugL in Pesufate(F5) acthaion by Preudo-rst- onder (uuerat. 2019) Uksarpure water zaro-yalen soa powder (0) Fenton gt, 45min) 100 Molar rato EPS =1:500 HEL! 120) 96808 Felis Tables ‘Summary ofthe sols process fo the removallderadation of pesticides Pesce Total concentration and ‘oP Teavres ine daa eerenees ‘Aatnpbos methyl) Yimgt* ‘Ulrasound eaten, Removal eficency 20: (Ggawaleral horpyios 2016) ‘aqueous solution pits, cr =08.96 Teasbeuwe ‘inpoe methyl =7850% Frequencye130 bi, elecrc power=s00W. Diazinon soma Ueasound fitaed by Fenton's Dizinon removal eficeney (Wang and ti, and Fenton-like rage (omin, 2016) ‘aqueous solution oe 8% Tease Mineralization Fe"=20mgL" “30% Huo 10mg" 4238, Sonalysis In the sonochemical process the main mechanism for the {destruction of the organic pollutants is the formation of hydroxy! radicals, oxygen atoms and hydrogen atoms as a result of water Pyrolysis Ultrasonic pressure waves, made by ultrasonic irradia- tion (20-500 kHz) of aqueous solutions, result in the formation (of vapor bubbles. These bubbles collapse violently after reaching, 2 critical resonance size and create transient high temperatures (25000 K)(Flint and suslick, 1961), high pressures (1000 bar) and highly reactive radicals (Suslick, 1990), Thermal decomposition ‘and numerous radical reactions take place during the degrada- tion of water contaminants (Holtmann et al, 1996; Yaghmacian et al, 2016). The critical parameters in sonolysis include pH, initial, Pesticide concentration, frequency, electric power and treatment time, Table 8 shows the results of (wo studies related to pesti- cide degradation by this process, Factors influencing the sonolytic degradation of azinphos-methyl and chlorpyrifos (Agarwal et al, 2015) and the degradation of insecticide diazinon by the Fenton and Fenton-like processes combined with ultrasound (Wang and ‘hil 2016) were investigated, Itwas reported (Agarwal etal,2015) that the initial concentration of pesticides had a strong effect on the removal efficeney of azinphos-methyl and chlorpyrifos. It was also observed that the degradation of pesticides decreased with the increase ofthe intial concentration of pollutant, while the pH vari- ation did not affect the degradation of pesticides (Agarwal etal 2016). The use of ultrasound requires high-energy consumption, ‘which results in a very low electrical efficiency compared to other AOPs technologies. Because of this, the hybrid technology, which ‘combines ultrasound with other AOPs, can provide more efficiency and additional benefits. Wang and Shih Wang ane Shih, 2016)con- sidered the effects of oxidants, such as persulphate ions (S032) and hydrogen peroxide (H,0,), transition metal (including Co™. ‘Ag’ and Fe"), the intial concentrations of iron/H20% in the Fen- {on process and the temperature on the degradation of diazinon. The diazinon was effectively degraded, and enhanced the toxicity ‘eduction, by the combination ofthe ultrasonic irradiation with the Fenton and Fenton-like processes (Wang and Shih, 2016). 42.8. Ozone based AOPS ‘Ozone is a strong oxidant itself with an oxidation potential of, 2.07. Ozone can react in aqueous solution either directly with target substrates (in ionized and dissociated form of organic com- ‘pounds, instead ofthe neutral form) or indirectly through reactions ‘with its free radical decomposition products (Kang and Hoffmann, 1998), The ozonation process is often applied simultaneously with other AOPs, such as UV radiation, hydrogen peroxide, ultrasound, activated carbon and catalysts to (a) improve the generation of “OH radicals, (b) enhance the oxidation rate of contaminants, (c) lower ozone consumption and, (d) convert contaminants into Jess toxic species which improves the biodegradability of the by- products. The ozonation process was applied to degrade omethoate (OMT), acetamiprid (ACMP) and dichlorvos (BDVP) pesticides (Table 9}, The combination of O, with Fe(Il)-oaded activated carbon(Fe@Ac), forthe effective generation of hydroxy radicals, accelerated the degradation of OMT and its dimethoate byprod- uct, as compared to ozonation alone and O3/AC (Ling et al, 2011), In the oxidation of ACMP by ozonation, second-order kinetic con- stants were recorded for the ACMP reactions with molecular ozone (0.25 M~ s~!) and hydroxyl radicals (2.1 x 10" M-" s~"), Thus, such values of the kinetic constants showed the resistance of the pesticide structure alongside ozone. Although the ozone dose of 5.5mgL~? was able to completely remove the ACMP with an initial concentration of 10 pM, its main intermediate products requited higher doses of ozone (Cruiz-Alcalde eta, 2017).Cruz-Alealde and no -M.Molaootan ares Safty and Entonnenta Protection 1262020) 252-307 Tabte ‘Summacy ofthe azone based AOPS process or the removaieradation of pestle Pes Tn conentation and ‘OP estes inte data References ‘Omeoate (OMT) omg ellploaded activated OnTemovalefceney(GOmin)—(Gngetal-2011) carbons Ozone, Inaqueous solution peers ‘oronaton alone (37.6%) <0siAC era Catalyst dose 200g", (6802) 03/5 FeaAc(s24 Oy Lomgt ‘Acetamipid(ACMP) ron zation Second order ate constans, (ceuz-aealde etal 2017) ‘n aqueous solution ‘zone dosage (5.5 mgt), Aca cemoaleffiioncy Diehlowos(D0VP) 20 in aqueous slution Second order ate constants, (Ceuz-aealde eal 2018) ASMP removal efcency ome . © ese veo st sats 9) moeusivom tae ig. 5. the forest plot ofthe organophasphors pesticide removal by typ of AP subgroup. Esplugas reported the removal of DDVP with the ozonation process ‘These authors observed that DDVP exhibited moderate reactivity ‘with molecular ozone, but indirect oxidation by “OH guaranteed the DDVP and the associated toxicity abatement. It was reported that second-order rate constants of the DDVP reactions with O3 and "OH were determined as 590 and 2.2:109 M-!s-1, respectively inneutral pH (Cruz-Alcalde etal, 2018), 42.10. other AOPS Bustos and coworkers have evaluated the potential photodegra- dation of dichlorvos (DDVP) under simulated sunlight and UV-254 inadiation (Table 10) (Bustos et al. 2019). In addition, the influ- cence on this processof dissolved oxygen(DO)and dissolved organic ‘matter (DOM) ~especially the humic fraction of DOM- on the degra- {ation of DDVP was carefully considered. The presence of DO in ultrapure water significantly improved the photodegradation of DDVP, which proved the importance of the role of oxygen in the ‘degradation of pesticides in natural waters under solar radiation, Although UVC shows more removal efficiency compare to sunlight, ‘more energy and photons flux are necessary to achieve the desired condition (Bustos etal, 2019), 43. Meta-analysis ‘The meta-analysis was performed considering six studies. All studies, except one, used photocatalytic process as AOP. Four types of pesticide were used in these studies, such as chlorpyrifos, reported in two studies (Amiri et al, 2018; Naddall et al, 2018), 1M Mokooon eal oes Safety and Enianmentalotetion 134 (2020) 292-207 20s rable10 Sty of iret ADP proces fr the removalaradation of pesiie. Pesce Thal concentration and oP ete ‘aoe ta Tees Dons (OBWP) 45Min Deionized wate Paden DWP emoval icy (Gusto, 2019) ‘Wosteterteaen an ‘toe (stg inaction wc) esc of 00> pucaosoa 70062 pi? |e Do byersinte sy * © eseowen wit ‘hema, 2016) Se mosey 40 sutcl saied =.=) <> rseosie) 0 choryaos| i ow 201 +! smunam wo a (201 | wmurmson war Suto! (eames =61%, p+ 0302) D>} emuess son 167 posts “Toc A(2017) Subal (suned = 5, Daznen Mascon, SR (2017) Tool 2018) Subeat (squmos = 00%, Ovral (squared = 95.3%, NOTE: Woghts re ton random fics aniss 04(6215,6752) 1008 t04(6215,6752) 1900 7938(1676,8195) 1810 7382(7325,8598) 1720 7o21(7688,8155) 3531, ote 5 90(68-14,7565) 10000 Fig-6. The forest plo ofthe organophosphorus pesticide removal by typeof pesticide subsroun diazinon, reported also in two studies (Mimasoomni et al, 20173 ‘Toolabi etal, 2019) and, in one study, malathion and acetariprid ‘were reported (Toolabi et al, 2017), The pooled mean percentage of AOP for pesticide degradation was 66.8 (95 RCI: $8.1-75.6), after excluding the only study in ‘which UV/F202 was used, the overall average percentage of AOP For pesticide degradation using the photocatalytic process was 66.2 (05 % Cl: 760-850), as shown in Fiz. 5. We also conducted a sub- _group analysis based on the type of pesticide used. in the studies, ‘which used the photocatalytic pracess as AOP, the highest removal efficiency was obtained for diazinon with an average percentage of 79.2 (95 % CI:768-81.5), The pooled removal efficiency for chlor Dyfifos was $2.93 (95 SCI: 46.9-58.9, as depicted in Fi. 6. 5. Conclusions ‘This study constitutes the first systematic review exclusively focused on the treatment of organophosphorus pesticides by sev- feral AOPS. The available literature reviewed here has shown a growing interest in recent years in. AOPS applications for the removal of pesticides from aqueous media, It has been clearly ‘demonstrated that most of the pesticides reviewed in this docu- ‘ment are substantially reactive and readily degradable by various AOPS. The most studied pesticides are chlorpyrifos and diazinon, since they have been identified as the main ones available and ‘usable in farmlands. In addition, the results of the meta-analysis of some papers confirm that the common of the AOPS tested showed 4 remarkable efficiency in the destruction of the target compounds by 70 %. Among the AOPs, photocatalytic and Fenton processes appear to be the most common technologies for the degradation ‘of organophosphorus pesticides. Declaration of Competing Interest All authors have participated in (a) conception and design, ot analysis and interpretation of the data; (b) drafting the article fr revising it critically for important intellectual content: and (c) approval a the final version, This manuscript has not been submit- ted t0, nor is under review at, another journal or other publishing venue, The authors have no affiliation with any organization witha 205 -M.Molaootan ares Safty and Entonnenta Protection 1262020) 252-307 direct or indirect financial interest in the subject matter discussed inthe manuscript. Acknowledgement ‘The authors would like to thank the Environmental Health Engineering Research Center, the Kerman University of Medical Sciences, for their scientific supports. References ‘Mom, AC. Chauthur. M. Kuty SRM. Mua, K, 2014 UV Fenon sd sequee ing batch rector teatime of chogpyi, cypermethrin and cratlont Desc wastewater In Bodeteror Bodegataton 93, 195-201 Aeawal, S.Tyog, Gupta VX. 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