Organophosphate Triesters and Diester Degradation Products in Municipal Sludge from Wastewater Treatment Plants in China: Spatial Patterns and Ecological Implications

Fu, Lingfang; Du, Bibai; Wang, Fei; Lam, James C.W.; Zeng, Lixi; Zeng, Eddy Y.

doi:10.1021/acs.est.7b04106

Cited by 117 publications

(108 citation statements)

References 53 publications

(195 reference statements)

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“…The transformation of OP flame retardants in indoor and outdoor environments has been reported but has been poorly characterized . Fu et al reported the estimated half‐lives for Cl‐PFRs to be higher than those for non‐chlorinated ones using EPI Suite version 4.11 . Since the uptake of PFRs in humans occurs by dermal contact following ingestion as the primary route of exposure, it is imperative to understand the fate and toxicity of OP triesters in environmental media .…”

Section: Resultsmentioning

confidence: 99%

“…In addition, impurities resembling compounds of interest are common in the form of intermediates from synthesis procedures, side products, and/or degradation products. Such occurrences and phenomena greatly complicate monitoring the various forms and transformations of PFRs in the environment and their subsequently becoming potential sources of human exposure . Su et al demonstrated that OP triesters with halogens and aryl functional groups are less stable than those with alkyl groups.…”

Section: Resultsmentioning

confidence: 99%

“…Abiotic degradation experiments of Cl‐PFRs were conducted at a single concentration of 100 ng/mL and as mixtures of only or both diesters or triesters, yielding the same final concentration. Ester bond hydrolysis has been reported for the degradation of Cl‐PFRs in aqueous systems and is independent of their initial concentration . The hydroxide anion is a nucleophile for ester bonds and it has been reported in the alkaline‐catalyzed and metal hydr(oxide)‐catalyzed hydrolysis of OP triesters .…”

Section: Methodsmentioning

confidence: 99%

“…Numerous monitoring studies have reported OP triesters entering the water cycle and being detected in a suite of aqueous environments such as river and marine waters, surface and ground waters, drinking and tap waters, precipitation and rain waters, and influents and effluents of sewage treatment plants . Ester bonds in OPFRs are prone to abiotic hydrolysis that determines their stability and reactivity in aqueous media . A pH‐dependent hydrolysis of OP triesters was characterized by Su et al, indicating their variable fate in environmental waters depending on the pH.…”

Section: Introductionmentioning

confidence: 99%

“…1,9,[15][16][17][18][19][20][21][22][23][24] Ester bonds in OPFRs are prone to abiotic hydrolysis that determines their stability and reactivity in aqueous media. 25,26 A pH-dependent hydrolysis of OP triesters was characterized by Su et al, 25 indicating their variable fate in environmental waters depending on the pH.…”

Section: Introductionmentioning

confidence: 99%

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Mass defect filtering for suspect screening of halogenated environmental chemicals: A case study of chlorinated organophosphate flame retardants

Dolios

Patel

Arora

et al. 2019

Rapid Comm Mass Spectrometry

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Rationale Organophosphate flame retardants (OPFRs) are a class of flame retardants widely found in environmental and biological matrices that have been extensively studied due to their adverse health effects in humans. OPFRs are loosely bound chemicals that can detach from treated products and be released into indoor and outdoor environments, where they have the potential to further undergo transformation and degradation processes, in particular the chlorinated OPFRs (Cl‐PFRs). Their detection remains a moving target for analysts, and traditional targeted mass spectrometry methods are suitable only for those compounds with authentic standards. Methods Mass defect filter (MDF) is a strategy to filter molecular features using thresholds applied to the mass defect value of a target ion or molecular feature of interest. We have developed an MDF strategy for the detection and tentative identification of twelve potential Cl‐PFR transformation products in a study mixture of six known Cl‐PFRs using MS/MS data acquired on a high‐resolution mass spectrometer. Most compounds in the Cl‐PFRs family share a ClO4P group as a core structure, of which modification results in a significant shift in the exact masses of the resulting compounds but show only a minimal shift in their mass defects. Subsequently, the MDF strategy was employed to tentatively identify Cl‐PFRs retrospectively in six human urine samples that had previously been analyzed. Results MDF in combination with product ion filtering for the characteristic [H2O3P]+ and [H4O4P]+ ions and neutral loss filtering for the characteristic CnH2n‐xClx group resulted in revealing suspects and homologues in the Cl‐PFRs family. Furthermore, the MDF of the product ions detected additional Cl‐PFR‐related compounds that differed significantly in the exact masses of both precursor and product ions but had minimal shift in the mass defects of product ions. The mass defect of one or more common product ions helped to detect a few Cl‐PFR analogs that had not been identified by MDF of the core structure precursor ion. Conclusions MDF helped to detect some Cl‐PFRs present in lower concentrations, which went undetected without data filters. MDF also helped to detect chromatographic peaks for Cl‐PFR homologues that are likely structural analogs that resulted from impurities and/or derivatives and transformation products. The methodology was applied to demonstrate and tentatively detect known and suspect Cl‐PFRs in human urine samples retrospectively.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%