Reductive degradation of chlorinated organophosphate esters by nanoscale zerovalent iron/cetyltrimethylammonium bromide composites: Reactivity, mechanism and new pathways

Li, Dan; Zhong, Yin; Zhu, Xifen; Wang, Heli; Yang, Weiqiang; Deng, Yangbo; Huang, Weilin; Peng, Ping’an

doi:10.1016/j.watres.2020.116447

Cited by 38 publications

(13 citation statements)

References 52 publications

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“…Li et al have reported the abiotic reductive transformation of TCEP to ethene and ethane by nanoscale zero-valent iron. 43 The amount of ethene increased continuously with the transformation of TCEP and reached the maximum on Day 10, followed by a decline at the later stage of the experiment (Figure 1B). Approximately 1.93 ± 0.12 μmol of ethene was generated when 3.88 ± 0.22 μmol of TCEP was completely transformed on Day 10, meaning that 50% of TCEP was reductively transformed to produce ethene.…”

Section: ■ Results and Discussionmentioning

confidence: 92%

“…To our knowledge, this is the first study to report that TCEP and TCPP can be biologically transformed to gaseous products ethene/ethane and propene, respectively (Figure E). Li et al have reported the abiotic reductive transformation of TCEP to ethene and ethane by nanoscale zero-valent iron . The amount of ethene increased continuously with the transformation of TCEP and reached the maximum on Day 10, followed by a decline at the later stage of the experiment (Figure B).…”

Section: Resultsmentioning

confidence: 98%

“…A similar reaction mechanism has been reported for the abiotic reductive transformation of TCEP to ethene and BCEP by nanoscale zero-valent iron. 43 In addition, Zipse 49 reported that β-(phosphatoxy)alkyl radicals with the structure similar to that of R1 can undergo C−O bond cleavage to form alkenes. Likewise, there was no significant difference in the δD value between the propene generated from the transformation of TCPP in D 2 O (−150.74 ± 3.65‰) and that in H 2 O (−149.37 ± 1.57‰) (p > 0.05; Tables S4 and S6), indicating that one-electron transfer, followed by C−O bond cleavage is likely the reaction mechanism underlying the transformation of TCPP to propene and BCPP (Figure 2B).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…BCEP radical may be further reduced and then protonated with D + to form deuterium-labeled BCEP. A similar reaction mechanism has been reported for the abiotic reductive transformation of TCEP to ethene and BCEP by nanoscale zero-valent iron . In addition, Zipse reported that β-(phosphatoxy)alkyl radicals with the structure similar to that of R1 can undergo C–O bond cleavage to form alkenes.…”

Section: Resultsmentioning

confidence: 99%

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Dehalococcoides-Containing Enrichment Cultures Transform Two Chlorinated Organophosphate Esters

Zhu

Deng

Fang

et al. 2022

Environ. Sci. Technol.

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Although chlorinated organophosphate esters (Cl-OPEs) have been reported to be ubiquitously distributed in various anoxic environments, little information is available on their fate under anoxic conditions. In this study, we report two Dehalococcoides-containing enrichment cultures that transformed 3.88 ± 0.22 μmol tris(2-chloroethyl) phosphate (TCEP) and 2.61 ± 0.02 μmol tris(1-chloro-2-propyl) phosphate (TCPP) within 10 days. Based on the identification of the transformed products and deuteration experiments, we inferred that TCEP may be transformed to generate bis(2-chloroethyl) phosphate and ethene via one-electron transfer (radical mechanism), followed by C−O bond cleavage. Ethene was subsequently reduced to ethane. Similarly, TCPP was transformed to form bis(1-chloro-2-propyl) phosphate and propene. 16S rRNA gene amplicon sequencing and quantitative polymerase chain reaction analysis revealed that Dehalococcoides was the predominant contributor to the transformation of TCEP and TCPP. Two draft genomes of Dehalococcoides assembled from the metagenomes of the TCEP-and TCPP-transforming enrichment cultures contained 14 and 15 putative reductive dehalogenase (rdh) genes, respectively. Most of these rdh genes were actively transcribed, suggesting that they might contribute to the transformation of TCEP and TCPP. Taken together, this study provides insights into the role of Dehalococcoides during the transformation of representative Cl-OPEs.

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Section: ■ Results and Discussionmentioning

confidence: 92%

Section: Resultsmentioning

confidence: 98%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Dehalococcoides-Containing Enrichment Cultures Transform Two Chlorinated Organophosphate Esters

Zhu

Deng

Fang

et al. 2022

Environ. Sci. Technol.

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“…Product D is removed from one of the 1-chloropropane molecules to form product E, the P-O-C bonds of which are broken, followed by the formation of propionic acid through substitution, addition and SO4• − cleavage (Yu et al, 2019). The oxidative dechlorination in the second pathway confirms that the role of ZVI is not to reduce TCPP, but to activate persulfate to oxidize TCPP in the PS+Fe 0 +MC system (Li et al, 2021).…”

Section: Fig 5 Proposed Degradation Pathways Of Tcpp 387 388mentioning

confidence: 87%

Degradation of Tris(1-chloro-2-propanyl) Phosphate by the Synergistic Effect of Persulfate and Zero-valent Iron During a Mechanochemical Process

Qiao

Yang

Qian

et al. 2021

Preprint

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This study revealed a dual pathway for the degradation of tris (1-chloro-2-propanyl) phosphate (TCPP) by zero-valent iron (ZVI) and persulfate as co-milling agents in a mechanochemical (MC) process. Persulfate was activated with ZVI to degrade TCPP in a planetary ball mill. After milling for 2 h, 96.5% of the TCPP was degraded with the release of 63.16, 50.39 and 42.01% of the Cl−, SO42− and PO43−, respectively. In the first degradation pathway, persulfate was activated with ZVI to produce hydroxyl (·OH) radicals and ZVI is oxidized to Fe(Ⅱ) and Fe(Ⅲ). A substitution reaction occurred as a result of the attack of ·OH on the P–O–C bonds, leading to the successive breakage of the three P–O–C bonds in TCPP to produce PO43−. In the second pathway, a C–Cl bond in part of the TCPP molecule was oxidized by SO4·− to carbonyl and carboxyl groups. The P–O–C bonds continued to react with ·OH to produce PO43−. Finally, the intermediate organochloride products were further reductively dechlorinated by ZVI. However, the synergistic effect of the oxidation (·OH and SO4·−) and the reduction reaction (ZVI) did not completely degrade TCPP to CO2, resulting in a low mineralization rate (35.87%). Moreover, the intermediate products still showed the toxicities in LD50 and developmental toxicant. In addition, the method was applied for the degradation of TCPP in soil, and high degradations (>83.83%) were achieved in different types of soils.Speciality: Phosphorus flame retardants; Advanced oxidation process; Ball milling

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Graphene oxide enhanced the reductive sequestration of UO22+, ReO4−, SeO42− and SeO32− by zero-valent iron: batch, column and mechanism investigations

Chen

Cheng²,

Sheng³

2022

J Radioanal Nucl Chem

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Reductive degradation of chlorinated organophosphate esters by nanoscale zerovalent iron/cetyltrimethylammonium bromide composites: Reactivity, mechanism and new pathways

Cited by 38 publications

References 52 publications

Dehalococcoides-Containing Enrichment Cultures Transform Two Chlorinated Organophosphate Esters

Dehalococcoides-Containing Enrichment Cultures Transform Two Chlorinated Organophosphate Esters

Degradation of Tris(1-chloro-2-propanyl) Phosphate by the Synergistic Effect of Persulfate and Zero-valent Iron During a Mechanochemical Process

Graphene oxide enhanced the reductive sequestration of UO22+, ReO4−, SeO42− and SeO32− by zero-valent iron: batch, column and mechanism investigations

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