Formation of Glyphosate and AMPA During Ozonation of Waters Containing Ethylenediaminetetra(methylenephosphonic acid)

Klinger, Josef; Lang, Minglin; Sacher, Frank; Brauch, Heinz‐Jürgen; Maier, D.; Worch, Eckhard

doi:10.1080/01919519808547279

Cited by 22 publications

(8 citation statements)

References 13 publications

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“…In the previous works, some investigations have indicated EDTMP could be oxidized to hydroxymethylene-phosphonic acid (HMP, shown in Scheme 1B), aminomethylene-phosphonic acid (AMP, shown in Scheme 1B) and iminodi(methylene-phosphonic acid) (IDMP, shown in Scheme 1B) in the presence of molecular oxygen and ozone [32][33][34]. Similarly, after HAuCl 4 is reduced by EDTMP, these oxidation products of EDTMP (i.e.…”

Section: Resultsmentioning

confidence: 98%

Facile controlled preparation of phosphonic acid-functionalized gold nanoparticles

Zhang

Zhou

Chen

et al. 2010

Journal of Colloid and Interface Science

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Section: Resultsmentioning

confidence: 98%

Facile controlled preparation of phosphonic acid-functionalized gold nanoparticles

Zhang

Zhou

Chen

et al. 2010

Journal of Colloid and Interface Science

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“…As has been shown previously, AMPA is glyphosate's main biodegradation and photodegradation product in the environment, and this is also true for chemical oxidation (Brosillon et al, 2006;Mehrsheikh et al, 2006). Simple UV disinfection does not remove AMPA from drinking water (Brosillon et al 2006;Assalin et al 2010;Klinger et al 1998).…”

Section: Drinking Water Treatmentmentioning

confidence: 86%

AminoMethylPhosphonic acid (AMPA) in natural waters: Its sources, behavior and environmental fate

Piel²,

2017

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The widely occurring degradation product aminomethylphosphonic acid (AMPA) is a result of glyphosate and amino-polyphosphonate degradation. Massive use of the parent compounds leads to the ubiquity of AMPA in the environment, and particularly in water. The purpose of this review is to summarize and discuss current insights into AMPA formation, transport, persistence and toxicity. In agricultural soils, AMPA is concentrated in the topsoil, and degrades slowly in most soils. It can reach shallow groundwater, but rarely managed to enter deep groundwater. AMPA is strongly adsorbed to soil particles and moves with the particles towards the stream in rainfall runoff. In urban areas, AMPA comes from phosphonates and glyphosate in wastewater. It is commonly found at the outlets of Wastewater Treatment Plants (WWTP). Sediments tend to accumulate AMPA, where it may be biodegraded. Airborne AMPA is not negligible, but does wash-out with heavy rainfall. AMPA is reported to be persistent and can be biologically degraded in soils and sediments. Limited photodegradation in waters exists. AMPA mainly has its sources in agricultural leachates, and urban wastewater effluents. The domestic contribution to urban loads is negligible. There is a critical lack of epidemiological data - especially on water exposure - to understand the toxicological effects, if any, of AMPA on humans. Fortunately, well operated water treatment plants remove a significant proportion of the AMPA from water, even though there are not sufficient regulatory limits for metabolites.

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“…The failure of synthetic efforts involving orthophosphate (instead of phosphonate) may imply that initial coordination of the phosphonate ligand to Mo(VI) is a necessary step in the process. Phosphonate sensitivity to oxidizers is well-known. , Studies have proven the production of orthophosphate, along with other organic fragments (depending on the degrading phosphonate), such as iminodiphosphonate, formate, N -formyl iminodi(methylene)phosphonate, , pyruvate, phosphonopyruvate, acetate, acetaldehyde, aminomethylphosphonic acid, glyphosate, and others. It has also been reported that the presence of metal ions enhances phosphonate degradation .…”

Section: Resultsmentioning

confidence: 99%

“…Phosphonate sensitivity to oxidizers is well-known. 7,8 Studies have proven the production of orthophosphate, along with other organic fragments (depending on the degrading phosphonate), such as iminodiphosphonate, formate, N-formyl iminodi(methylene)phosphonate, 58,59 pyruvate, phosphonopyruvate, acetate, acetaldehyde, 60 aminomethylphosphonic acid, glyphosate, 61 and others. It has also been reported that the presence of metal ions enhances phosphonate degradation.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Phosphonate Decomposition-Induced Polyoxomolybdate Dumbbell-Type Cluster Formation: Structural Analysis, Proton Conduction, and Catalytic Sulfoxide Reduction

et al. 2019

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The reaction of MoO 4 2− with a number of phosphonic acids [bis-(phosphonomethyl)glycine, R,S-hydroxyphosphonoacetic acid, 1-hydroxyethane-1,1-diphosphonic acid, phenylphosphonic acid, aminotris(methylene phosphonic acid), and 1,2ethylenediphosphonic acid] under oxidizing (H 2 O 2 ) hydrothermal conditions at low pH leads to rupture of the P−C bond, release of orthophosphate ions, and generation of the octanuclear, phosphate-bridged, polyoxometalate molybdenum cluster (NH 4 ) 5 [Mo 8 (OH) 2 O 24 (μ 8 -PO 4 )](H 2 O) 2 (POMPhos). This cluster has been fully characterized and its structure determined. It was studied as a proton conductor, giving moderate values of σ = 2.13 × 10 −5 S•cm −1 (25°C) and 1.17 × 10 −4 S•cm −1 (80°C) at 95% relative humidity, with E a = 0.27 eV. The POMPhos cluster was then thermally treated at 310°C, yielding (NH 4 ) 2.6 (H 3 O) 0.4 (PO 4 Mo 12 O 36 ) together with an amorphous impurity containing phosphate and molybdenum oxide. This product was also studied for its proton conductivity properties, giving rise to an impressively high value of σ = 2.43 × 10 −3 S• cm −1 (25°C) and 6.67 × 10 −3 S•cm −1 (80°C) at 95% relative humidity, 2 orders of magnitude higher than those corresponding to the "as-synthesized" solid. The utilization of POMPhos in catalytic reduction of different sulfoxides was also evaluated. POMPhos acts as an efficient homogeneous catalyst for the reduction of diphenyl sulfoxide to diphenyl sulfide, as a model reaction. Pinacol was used as a low-cost, environmentally friendly, and highly efficient reducing agent. The effects of different reaction parameters were investigated, namely the type of solvent and reducing agent, presence of acid promoter, reaction time and temperature, loading of catalyst and pinacol, allowing to achieve up to 84−99% yields of sulfide products under optimized conditions. Substrate scope was tested on the examples of diaryl, alkylaryl, dibenzyl, and dialkyl sulfoxides and excellent product yields were obtained.

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Formation of Glyphosate and AMPA During Ozonation of Waters Containing Ethylenediaminetetra(methylenephosphonic acid)

Cited by 22 publications

References 13 publications

Facile controlled preparation of phosphonic acid-functionalized gold nanoparticles

Facile controlled preparation of phosphonic acid-functionalized gold nanoparticles

AminoMethylPhosphonic acid (AMPA) in natural waters: Its sources, behavior and environmental fate

Phosphonate Decomposition-Induced Polyoxomolybdate Dumbbell-Type Cluster Formation: Structural Analysis, Proton Conduction, and Catalytic Sulfoxide Reduction

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