Formation of diphenylthioarsinic acid from diphenylarsinic acid under anaerobic sulfate-reducing soil conditions

Hisatomi, Shihoko; Guan, Ling; Nakajima, Mami; Fujii, Kunihiko; Nonaka, Manabu; Harada, Naoki

doi:10.1016/j.jhazmat.2013.08.020

Cited by 7 publications

(7 citation statements)

References 22 publications

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“…1A and B, Table S2) and this may be attributed to SRB activity as first reported by Guan et al (2012). DPTAA was a major metabolite of DPAA in sulfide soil and this is consistent with previous results reported by Hisatomi et al (2013). In the present study some soluble sulfide in anoxic soil also transformed DPAA to DPTAA despite the lack of exogenous sulfate addition.…”

Section: Impact Of Sulfate and Fe(iii) Reduction On Dpaa Thionationsupporting

confidence: 93%

“…Sulfide derived from microbial sulfate reduction can react directly with As to form soluble thioarsenate species or insoluble precipitates when substantial amounts of dissolved As and sulfide are present (Root et al, 2013;Stucker et al, 2014;Xu et al, 2011). Limited studies also show that DPAA can be rapidly dephenylated or methylated under flooded soil conditions (Maejima et al, 2011;Arao et al, 2009) and thionation is an important anaerobic pathway for DPAA under sulfate-reducing conditions (Guan et al, 2012;Hisatomi et al, 2013). However, the partitioning of DPAA in flooded soil was underestimated.…”

Section: Introductionmentioning

confidence: 99%

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Solid-solution partitioning and thionation of diphenylarsinic acid in a flooded soil under the impact of sulfate and iron reduction

Zhu

et al. 2016

Science of The Total Environment

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• We first investigated the solid-solution partitioning of DPAA in a flooded soil.• We first examined the impacts of sulfate and iron reduction on DPAA partitioning.• Elevated DPAA mobilization and thionation was observed in sulfide soil.• DPAA mobilization associated with Fe(III) reductive dissolution was demonstrated.• Enhanced mobilization of DPAA and sulfate reduction promoted DPAA thionation. Editor: Jay Gan Diphenylarsinic acid (DPAA) is a major organic arsenic (As) compound derived from abandoned chemical weapons. The solid-solution partitioning and transformation of DPAA in flooded soils are poorly understood but are of great concern. The identification of the mechanisms responsible for the mobilization and transformation of DPAA may help to develop effective remediation strategies. Here, soil and Fe mineral incubation experiments were carried out to elucidate the partitioning and transformation of DPAA in anoxic (without addition of sulfate or sodium lactate) and sulfide (with the addition of sulfate and sodium lactate) soil and to examine the impact of sulfate and Fe(III) reduction on these processes. Results show that DPAA was more effectively mobilized and thionated in sulfide soil than in anoxic soil. At the initial incubation stages (0-4 weeks), 6.7-74.5% of the total DPAA in sulfide soil was mobilized likely by sorption competition with sodium lactate. At later incubation stage (4-8 weeks), DPAA was almost completely released into the solution likely due to the near-complete Fe(III) reduction. Scanning transmission X-ray microscopy (STXM) results provide further direct evidence of elevated DPAA release coupled with Fe(III) reduction in sulfide environments. The total DPAA fraction decreased significantly to 24.5% after two weeks and reached 3.4% after eight weeks in sulfide soil, whereas no obvious elimination of DPAA occurred in anoxic soil at the initial two weeks and the total DPAA fraction decreased to 10.9% after eight weeks. This can be explained in part by the enhanced mobilization of DPAA and sulfate reduction in G R A P H I C A L A B S T R A C T a b s t r a c t a r t i c l e i n f o Contents lists available at ScienceDirectScience of the Total Environment j o u r n a l h o m e p a g e : w w w . e l s e v i e r . c o m / l o c a t e / s c i t o t e n v sulfide soil compared with anoxic soil. These results suggest that under flooded soil conditions, Fe(III) and sulfate reduction significantly promote DPAA mobilization and thionation, respectively, and we suggest that it is essential to consider both sulfate and Fe(III) reduction to further our understanding of the environmental fate of DPAA.

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Section: Impact Of Sulfate and Fe(iii) Reduction On Dpaa Thionationsupporting

confidence: 93%

Section: Introductionmentioning

confidence: 99%

Solid-solution partitioning and thionation of diphenylarsinic acid in a flooded soil under the impact of sulfate and iron reduction

Zhu

et al. 2016

Science of The Total Environment

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“…3), and we suggest this resulted from the desorption of solid phase-associated inorganic As, rather than a complete mineralization of DPAA due to the following reasons. Firstly, there is no direct evidence that DPAA or PAA can be completely mineralized in flooded or sulfate-reducing soils according to the reported literature (Arao et al 2009;Maejima et al 2011b;Hisatomi et al 2013;Guan et al 2015). Secondly, the reductive dissolution of Fe(III) (hydr)oxides in sulfide soil, as indicated by the increased concentrations of dissolved Fe(II) and HCl-extractable Fe(II) (Fig.…”

Section: Impact Of Fe(iii) Reduction On Dpaa Mobilizationmentioning

confidence: 97%

“…One effective solution to remove DPAA from contaminated soils is biostimulation using indigenous microorganisms that are stimulated by exogenous carbon sources and nutrients, and the main transformation pathway of DPAA involves dephenylation (Maejima et al 2011b), methylation (Arao et al 2009), and thionation (Nakamiya et al 2013). Among these, thionation results in the most effective transformation of DPAA in biostimulated soils (Guan et al 2012) and diphenylthioarsinic acid (DPTAA) was the major metabolite detected after incubation with sulfate and lactate (Hisatomi et al 2013). Biostimulated sulfate reduction has already been tested as an effective strategy for the remediation of inorganic arsenic (As) in soils (Maguffin and Jin 2018) in which dissimilatory Fe(III) reduction driven by microbial metabolism of dissolved organic matter (DOM) is commonly implicated as a key factor affecting the mobility, and thereby the thionation, of inorganic As (Burton et al 2008;Borch et al 2009).…”

Section: Introductionmentioning

confidence: 99%

Contrasting effects of iron reduction on thionation of diphenylarsinic acid in a biostimulated Acrisol

Zhu

Luo

Cheng

et al. 2020

Environ Sci Pollut Res

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Diphenylarsinic acid (DPAA) is an emerging phenylarsenic compound derived from chemical warfare agents. It has been suggested that biostimulation of sulfate reduction decreases the concentrations of DPAA in soils. However, biostimulation often induces Fe(III) reduction which may affect the mobility and thereby the transformation of DPAA. Here, a soil incubation experiment was carried out to elucidate the impact of Fe(III) reduction on the mobilization and transformation of DPAA in a biostimulated Acrisol with the addition of sulfate and lactate. DPAA was significantly mobilized and then thionated in the sulfide soil (amended with sulfate and sodium lactate) compared with the anoxic soil (without addition of sulfate or sodium lactate). At the start of the incubation period, 41.8% of the total DPAA in sulfide soil was mobilized, likely by the addition of sodium lactate, and DPAA was then almost completely released into the solution after 2 weeks of incubation, likely due to Fe(III) reduction. The relatively low fraction of oxalate-extractable Fe in Acrisol, which contributes significantly to DPAA sorption and is more active and reduction-susceptible, may explain the observation that only < 40% of the Fe(III) (hydr)oxides were reduced when DPAA was completely released into the solution. A more rapid and final enhanced elimination of DPAA was observed in sulfide soil and the fraction of total DPAA decreased to 60.1 and 91.0%, respectively, at the end of the incubation in sulfide soil and anoxic soil. The difference appears to result from increased DPAA mobilization and sulfate reduction in sulfide soil. On the other hand, the formation of FeS precipitate, a product of Fe and sulfate reduction, may reduce the efficiency of DPAA thionation. Accordingly, the potentially contrasting effects of Fe(III) reduction on DPAA thionation need be considered when planning biostimulated sulfate reduction strategies for DPAA-contaminated soils.

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“…A paper published a year later demonstrated the identification of the major metabolite formed in soil cultures spiked with DPA. 17 Time-of-flight high-resolution mass spectrometry (TOF-HRMS) was utilized for obtaining the exact mass and proposed elemental composition for the detected degradation product. In the HRMS spectrum, a peak at m / z 260.97179 with the elemental composition of C 12 H 12 AsSO was detected.…”

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confidence: 99%

Identification of Degradation Products of Sea-Dumped Chemical Warfare Agent-Related Phenylarsenic Chemicals in Marine Sediment

et al. 2020

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Previously unknown phenylarsenic chemicals that originated from chemical warfare agents (CWAs) have been detected and identified in sediment samples collected from the vicinity of chemical munition dumpsites. Nontargeted screening by ultrahigh-performance liquid chromatography–high-resolution mass spectrometry (UHPLC-HRMS) was used for detection of 14 unknown CWA-related phenylarsenic chemicals. Methylated forms of Clark I/II, Adamsite, and phenyldichloroarsine were detected in all analyzed sediment samples, and their identification was based on synthesized chemicals. In addition, other previously unknown CWA-related phenylarsenic chemicals were detected, and their structures were elucidated using MS/HRMS technique. On the basis of relative isotope ratios of protonated molecules and measures of exact masses of formed fragment ions, it could be concluded that some of these unknown chemicals contained a sulfur atom attached to an arsenic atom. In addition to that, some of the samples contained chemicals that had formed via addition of an OH group to the aromatic ring. However, it is not possible to say how these chemicals are formed, but the most plausible cause is activities of marine microbes in the sediment. To our knowledge, these chemicals have not been detected from sediment samples previously. Sensitive analytical methods are needed for these novel chemicals to assess the total CWA burden in marine sediments, and this information is essential for the risk assessment.

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Formation of diphenylthioarsinic acid from diphenylarsinic acid under anaerobic sulfate-reducing soil conditions

Cited by 7 publications

References 22 publications

Solid-solution partitioning and thionation of diphenylarsinic acid in a flooded soil under the impact of sulfate and iron reduction

Solid-solution partitioning and thionation of diphenylarsinic acid in a flooded soil under the impact of sulfate and iron reduction

Contrasting effects of iron reduction on thionation of diphenylarsinic acid in a biostimulated Acrisol

Identification of Degradation Products of Sea-Dumped Chemical Warfare Agent-Related Phenylarsenic Chemicals in Marine Sediment

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