Distributions of polycyclic musk fragrance in wastewater treatment plant (WWTP) effluents and sludges in the United States

Sun, Peizhe; Casteel, Kenneth; Dai, Hongjian; Wehmeyer, Kenneth R.; Kiel, Brian; Federle, Thomas W.

doi:10.1016/j.scitotenv.2014.04.038

Cited by 33 publications

(11 citation statements)

References 14 publications

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“…Hydrogen Abstraction Reactions. As presented in Figure 3, 10 hydrogen abstraction sites are identified in the HHCB structure: four (C (8) −H, C (9) −H, C (10) −H, and C (14) − H) in the −CH 2 − or −CH− group, four (C (7) −H, C (12) −H, C (15) −H, and C (18) −H) in the methyl group, and two (C (4) After the hydrogen abstraction from the methyl group, i.e., the −CH 3 − group, open-shell activated radicals IM7, IM12, IM14, and IM15 are produced. As shown in Figure 3, four transition states, TS7, TS12, TS14, and TS15 are located.…”

Section: Resultsmentioning

confidence: 99%

“…The rate constant of the C (7) atom site should be 3k R7 because of the existence of three equivalent hydrogen atoms. Besides, we assume the C (12) and C (13) atoms, and the C (17) and C (18) atoms, are equivalent, respectively, in our article. Thus, the rate constants of the C (12) and C (18) site should be 6k R12 and 6k R15 .…”

Section: Kinetic Calculationmentioning

confidence: 99%

“…Galaxolide (1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta-γ-2-benzopyran, HHCB) is one of the highest proportions of polycyclic musks and is defined as a high production volume (HPV) chemical by the U.S. Environmental Protection Agency (EPA) . Owing to its high yield and persistence, it is these days ubiquitous in the environment, − especially in the atmosphere around the world. The volatilization during the use of products containing HHCB, as well as water-to-air volatilization, can be deemed as important sources of HHCB to the atmosphere .…”

Section: Introductionmentioning

confidence: 99%

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Theoretical and Kinetic Properties of OH Radical-Initiated Oxidation of Galaxolide in the Atmosphere

Sun

Zhang

2018

J. Phys. Chem. A

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Galaxolide (HHCB), an important emerging contaminant, has attracted great environmental concern owing to its widespread occurrence and potential toxicity. In this study, the detailed multichannel mechanism of OH radical-initiated atmospheric degradation reactions of HHCB has been investigated by employing density functional theory (DFT). The reactants, transition states, intermediates, and products were optimized at the MPWB1K/6-31+G(d,p) level, and single-point energies were further refined at the MPWB1K/6-311+G(3df,2p) level of theory. The canonical variational transition-state (CVT) theory combined with the small curvature tunneling (SCT) was performed to evaluate the Arrhenius expressions and rate constants of key elementary reactions over a suitable range of 180−370 K. The thermodynamic and kinetic calculation results show that OH addition and hydrogen abstraction reactions are competitive pathways for HHCB. The dominant products in the presence of O 2 /NO are epoxide, dialdehyde, alcohol ketone, cyclolactone compounds, and HO 2 radicals. At 298 K, the total rate constant of OH-initiated degradation of HHCB is 2.71 × 10 −11 cm 3 molecule −1 s −1 . The atmospheric lifetime of HHCB determined by OH-initiated reactions is 10.09 h, which is in favor of the phenomenon of medium-range transport for HHCB in the atmosphere.

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Section: Resultsmentioning

confidence: 99%

Section: Kinetic Calculationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Theoretical and Kinetic Properties of OH Radical-Initiated Oxidation of Galaxolide in the Atmosphere

Sun

Zhang

2018

J. Phys. Chem. A

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“…Polycyclic musks (PCMs) are widely used as synthetic fragrances in a variety of personal care products and other everyday products, such as cleaning and washing agents and disinfectants . Among them, 1,3,4,6,7,8‐hexahydro‐4,6,6,7,8,8‐hexamethylcyclopenta( g )‐2‐benzopyran (Galaxolide, HHCB) and 7‐acetyl‐1,1,3,4,4,6‐hexamethyl‐1,2,3,4‐tetrahydronaphthalene (Tonalide, AHTN) are two typical PCMs that are produced in high volumes (ca.…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric analysis of polycyclic musks AHTN and HHCB and HHCB‐lactone in sewage sludge by gas chromatography/tandem mass spectrometry

Gao

Tian

Zeng

et al. 2019

Rapid Comm Mass Spectrometry

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Rationale Enantioselective analysis of chiral compounds is an interesting and challenging technique used to elucidate the degradation/transformation mechanisms of these compounds or understand their environmental processes. In this study, we have developed an effective separation and detection approach for the enantiomeric analysis of AHTN and HHCB, as well as a transformation product of HHCB (HHCB‐lactone), in sludge samples. Methods The analytical method was developed using a cyclodextrin‐based enantioselective gas chromatography column combined with tandem mass spectrometry (GC/MS/MS). The GC oven temperature gradients, the linear velocity of the helium carrier gas, as well as the MS/MS parameters, including quantitative and qualitative ion pairs, dwell times, and collision energies, were optimized to achieve good separation and high sensitivity for all target enantiomers. Results Baseline separations of all target enantiomers were observed. Limits of quantification (LOQs) for all enantiomers ranged from 0.010 to 0.045 μg/L, and calibration linearity for all single enantiomers was higher than 0.99. The intra‐day and inter‐day precisions for all single enantiomers of AHTN, HHCB, and HHCB‐lactone ranged from 0.8 to 3.8% and from 4.2 to 8.3%, respectively. Conclusions The developed method was fully validated through enantioselective analyses of AHTN, HHCB, and HHCB‐lactone in sludge samples collected from 17 WWTPs. The enantiomeric fractions (EFs) of HHCB and HHCB‐lactone in sludge samples distinctly deviated from 0.50, indicating a significant enantioselective transformation of HHCB with preferential degradation of the 4S enantiomers. Significant positive correlations were found between the EF values of cis‐HHCB enantiomers and cis‐HHCB‐lactone enantiomers in the sludge samples, implying that further efforts are still needed to clarify the degradation/transformation mechanism from HHCB to HHCB‐lactone.

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“…Due to their high lipophilicity, PCMs that end up in the waterways can bio-accumulate in aquatic organisms, such as fish and mussels, especially at low trophic levels (Seinen et al, 1999;Gomez et al, 2005;Díaz-Cruz and Barceló, 2015). Given the current high usage, there are concerns regarding environmental exposure and toxic effects of PCMs (Sun et al, 2014).…”

Section: Introductionmentioning

confidence: 99%

Ecological risks of personal care ingredients for subtropical benthic communities

Peng¹

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Pseudokirchneriella subcapitata Algae 72 h, Growth inhibition, NOEC 0.53 (Tamura et al. 2013) Daphnia magna Crustacean 21 d, Reproduction, NOEC 40 (Orvos et al. 2002) Daphnia magna Crustacean 21 d, Survival, NOEC 200 (Orvos et al. 2002) Ceriodaphnia dubia Crustacean 7 d, Survival, NOEC 50 (Orvos et al. 2002) Ceriodaphnia dubia Crustacean 7 d, Survival, NOEC 339 (Orvos et al. 2002) Ceriodaphnia dubia Crustacean 8 d, Reproduction, NOEC 30 (Tamura et al. 2013) Ceriodaphnia dubia Crustacean 7 d, Reproduction, NOEC 6 (Orvos et al. 2002) Ceriodaphnia dubia Crustacean 7 d, Reproduction, NOEC 182 (Orvos et al. 2002

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Distributions of polycyclic musk fragrance in wastewater treatment plant (WWTP) effluents and sludges in the United States

Cited by 33 publications

References 14 publications

Theoretical and Kinetic Properties of OH Radical-Initiated Oxidation of Galaxolide in the Atmosphere

Theoretical and Kinetic Properties of OH Radical-Initiated Oxidation of Galaxolide in the Atmosphere

Enantiomeric analysis of polycyclic musks AHTN and HHCB and HHCB‐lactone in sewage sludge by gas chromatography/tandem mass spectrometry

Ecological risks of personal care ingredients for subtropical benthic communities

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