Adsorption of bentazone and imazapyc from water by using functionalized silica: Experimental and computational analysis

Spaltro, Agustín; Simonetti, S.; Laurella, Sergio Luis; Ruiz, Danila Luján; Juan, Alfredo; Allegretti, Patricia Ercilia

doi:10.1016/j.jconhyd.2019.103542

Cited by 12 publications

(12 citation statements)

References 45 publications

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“…The shape of the pH-dependent adsorption curves observed in Fig 3A and 3B is similar to that for bentazone adsorption on mesoporous silica as observed by Bruzzoniti et al [9]. The only difference is that Bruzzoniti et al [9] (similarly to Spaltro et al [10]) observed also weak bentazone adsorption in the pH range of 5-7. The total specific surface area of silica (SSA) determined from the BET N 2 isotherms examined by Spaltro et al [10] was 264 m 2 /g and SSA of silica examined by Bruzzoniti et al [9] was in the range of 484-876 m 2 /g.…”

Section: Adsorption In Soils Containing No Organic Mattersupporting

confidence: 85%

“…The pH-dependent adsorption of bentazone on mesoporous silica (strong in the pH range of 2-4 and much weaker in the range of 5-7), as well as the weak adsorption of this compound on montmorillonite, were described by Bruzzoniti et al [9]. Adsorption of bentazone on silica at pH of 6.5-7.5 was observed also by Spaltro et al [10]. Furthermore, the adsorption of bentazone on synthesized iron oxides at a pH of 3.4-4.6 was stated by Clausen and Fabricius [11].…”

Section: Introductionmentioning

confidence: 65%

“…The only difference is that Bruzzoniti et al [9] (similarly to Spaltro et al [10]) observed also weak bentazone adsorption in the pH range of 5-7. The total specific surface area of silica (SSA) determined from the BET N 2 isotherms examined by Spaltro et al [10] was 264 m 2 /g and SSA of silica examined by Bruzzoniti et al [9] was in the range of 484-876 m 2 /g. The SSA determined from the N 2 adsorption isotherms of subsoils of Polish AR is typically in the range of 0.7-2.6 m 2 /g ( [46], see the data for subsoils of 611 and 805 profiles).…”

Section: Adsorption In Soils Containing No Organic Mattermentioning

confidence: 94%

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Adsorption of bentazone in the profiles of mineral soils with low organic matter content

et al. 2020

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The current laboratory adsorption study aimed at determination of the values of adsorption distribution coefficient (Kd) of bentazone in the profiles of Arenosols, Luvisols, and Cambisols, which are the most common arable mineral soils in Poland. The study attempted to identify the soil components that bind bentazone and the principal adsorption mechanisms of this compound as well as create a model capable of predicting its adsorption in soils. The Kd values determined in batch experiments after 24 h of shaking were very low, and ranged from 0.05 to 0.30 mL/g for the Ap horizon and 0 to 0.07 mL/g for subsoils. The results indicated that the anionic form of bentazone was adsorbed on organic matter, while in acidic soils the neutral form of bentazone was adsorbed on organic matter and sand. The detailed analyses of mineralogical composition revealed that the principal mineral that was responsible for the adsorption of bentazone was quartz, which content was strongly positively correlated with the sand fraction. In soils with pH < 5 and an organic carbon content of < 0.35%, quartz exhibited much greater affinity for the neutral bentazone form than organic matter. Fourier transform infrared photoacoustic spectroscopy analyses supported by computational methods have shown the most probable mechanisms behind the adsorption of bentazone on quartz. The created model, assuming the adsorption of bentazone on organic matter and on sand and using the spectrophotometrically determined dissociation constant of bentazone, very well explained the Kd variance in the 81 examined soils, while correctly predicting the adsorption based on soil properties described in the published data.

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Section: Adsorption In Soils Containing No Organic Mattersupporting

confidence: 85%

Section: Introductionmentioning

confidence: 65%

Section: Adsorption In Soils Containing No Organic Mattermentioning

confidence: 94%

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Adsorption of bentazone in the profiles of mineral soils with low organic matter content

et al. 2020

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“…3a) and no significant difference was observed between the removal of benzene in the Biocide FTR and that in the LS, BW, HS, and CO FTRs. The effluent benzene concentrations from the HS FTR were slightly lower than those from the other FTRs which can be attributed to the higher adsorption capacity of the soil under higher salinity conditions (Wang et al 2015;Ngueleu et al 2018;Spaltro et al 2019;Zhao et al 2019). By increasing the salinity and ionic strength in the aqueous phase, solubility of organic compounds decreases which referred to as the salting-out effect (Endo et al 2012) that influences the mass transfer process and results in a higher organic sorption in the soil.…”

Section: Effluent Organic Concentrationsmentioning

confidence: 98%

Effects of dissolved organic phase composition and salinity on the engineered sulfate application in a flow-through system

Shafieiyoun

Al-Raoush

Ismail

et al. 2020

Environ Sci Pollut Res

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Engineered sulfate application has been proposed as an effective remedy to enhance the rate-limited biodegradation of petroleumhydrocarbon-contaminated subsurface environments, but the effects of dissolved organic phase composition and salinity on the efficiency of this method are unknown. A series of flow-through experiments were conducted for 150 days and dissolved benzene, toluene, naphthalene, and 1-methylnaphthalene were injected under sulfate-reducing and three different salinity conditions for 80 pore volumes. Then, polycyclic aromatic hydrocarbons (PAHs) were omitted from the influent solution and just dissolved benzene and toluene were injected to investigate the influence of dissolved phase composition on treatment efficiency. A stronger sorption capacity for PAHs was observed and the retardation of the injected organic compounds followed the order of benzene < toluene < naphthalene < 1-methylnaphthalene. Mass balance analyses indicated that 50 and 15% of toluene and 1methlynaphtalene were degraded, respectively. Around 5% of the injected naphthalene degraded after injecting > 60 PVs influent solution, and benzene slightly degraded following the removal of PAH compounds. The results showed substrate interactions and composition can result in rate-limited and insufficient biodegradation. Similar reducing conditions and organic utilization were observed for different salinity conditions in the presence of the multi-component dissolved organic phase. This was attributed to the dominant microbial community involved in toluene degradation that exerted catabolic repression on the simultaneous utilization of other organic compounds and were not susceptible to changes in salinity.

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“…[ 9,10 ] In second place, possible remediation methods (specially the more selective ones) for water and soil polluted with pesticides are designed assuming specific molecular structure and functional groups. [ 11,12 ] At last, if the equilibrium can be shifted towards one tautomer or another by changing the solvent, then the different functional groups involved in tautomerism can be selectively modified by chemical reactions. [ 13,14 ] Moreover, solvent effect on rapid equilibria of clethodim should be useful for carrying out studies using organic solvents as a model to mimic functional groups presents in the plant cuticle constituents.…”

Section: Introductionmentioning

confidence: 99%

Tautomeric and E‐Z equilibria of the herbicide clethodim in water and organic solvents: A nuclear magnetic resonance and theoretical study

Caputo

Colasurdo

Allegretti

et al. 2020

J of Physical Organic Chem

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The herbicide clethodim can exist as different tautomeric forms and also as E‐Z isomers. Previous works have made some approach to the matter of tautomerization and have always stated that the E form was the only one stable. In this work, the investigation on the tautomeric equilibrium of clethodim is carried out in solution by means of proton nuclear magnetic resonance (1H NMR), carbon‐13 nuclear magnetic resonance (13C NMR), and correlation spectroscopy (COSY) experiments in four solvents (CDCl3, acetone‐d6, dimethylsulfoxide (DMSO)‐d6, and D2O). Major tautomeric species have been identified, and equilibrium constants have been calculated from the integration of hydrogens of the chloroallyl radical of clethodim. E‐ketoenolimine is the only detectable tautomer in CDCl3. Mixtures of E‐ketoenolimine and E‐diketoenamine tautomers are observed in acetone‐d6 and DMSO‐d6 (in ratios of 8:92 and 53:47, respectively). In water, the most abundant neutral tautomers are E‐ketoenolimine, E‐diketoenamine, and Z‐ketoenolimine (with a tautomeric ratio of 66:20:14). Identification of the E and Z tautomers is reported. Thermodynamic parameters (obtained by analysis of the effect of temperature) and theoretical calculations (energies and chemical shifts) support the assignations and tautomeric ratios when considering specific clethodim‐solvent hydrogen bonds. In the case of water, calculations suggest double bonded complexes that would be the cause of stability of the tautomers. These new observations on the structure of clethodim in solution open a new series of questions on its absorption mechanism, and they are also a tool for further chemical modification of this herbicide.

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Adsorption of bentazone and imazapyc from water by using functionalized silica: Experimental and computational analysis

Cited by 12 publications

References 45 publications

Adsorption of bentazone in the profiles of mineral soils with low organic matter content

Adsorption of bentazone in the profiles of mineral soils with low organic matter content

Effects of dissolved organic phase composition and salinity on the engineered sulfate application in a flow-through system

Tautomeric and E‐Z equilibria of the herbicide clethodim in water and organic solvents: A nuclear magnetic resonance and theoretical study

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