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Measurement of Temperature Dependence for Vapor Pressures of Seventeen OH-PBDEs and Eleven MeO-PBDEs by Gas Chromatographic Method

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Abstract

Hydroxylated polybromodiphenyl ethers (OH-PBDEs) and methoxylated polybrominated diphenyl ethers (MeO-PBDEs) are emerging organic pollutants. Supercooled liquid vapor pressures (p L) and enthalpies of vaporization (∆vap H) for seventeen OH-PBDEs and eleven MeO-PBDEs were determined by a gas chromatographic technique. p L at 298 K ranged from 0.0173 Pa for 2′-OH-BDE3 to 2.32 × 10−7 Pa for 3′-OH-BDE154 and they are approximately one order of magnitude smaller than those determined for the counterpart polybrominated diphenyl ethers (PBDEs). ∆vap H was in the range of 76–121 kJ/mol. The temperature dependence of p L was measured by fitting the experimental data with the log(p L/Pa) = a/(T/K) + b equation, and this corresponds to a 50–265 times higher p L value at 0 versus 30°C. Using fundamental quantum chemical descriptors, two quantitative structure–property relationship models (Q cum > 0.935) were developed to estimate p L at any temperature for the additional OH- and MeO-PBDE congeners.

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References

  • Abdallah MA, Harrad S (2011) Tetrabromobisphenol-a, hexabromocyclododecane and its degradation products in UK human milk: relationship to external exposure. Environ Int 37:443–448

    Article  CAS  Google Scholar 

  • Alonso MB, Azevedo A, Torres JPM, Dorneles PR, Eljarrat E, Barcelo D, Lailson-Brito J, Maim O (2014) Anthropogenic (PBDE) and naturally-produced (MeO-PBDE) brominated compounds in cetaceans—a review. Sci Total Environ 481:619–634

    Article  CAS  Google Scholar 

  • Athanasiadou M, Cuadra SN, Marsh G, Bergman Å, Jakobsson K (2008) Polybrominated biphenyl ethers (PBDEs) and bioaccumulative hydroxylated PBDE metabolites in young humans from Managua, Nicaragua. Environ Health Perspect 116(3):400–408

    Article  CAS  Google Scholar 

  • Bidleman TF (1984) Estimation of vapor-pressures for nonpolar organic-compounds by capillary gas-chromatography. Anal Chem 56:2490–2496

    Article  CAS  Google Scholar 

  • Bielli M, Carotenuto P, Delle Site V (1997) Advanced research on transport–environment interactions. In: 8th IFAC/IFIP/IFORS symposium on transportation systems vols 1–3:981–988

  • Chen DH, Bi XH, Liu M, Huang B, Sheng GY, Fu JM (2011) Phase partitioning, concentration variation and risk assessment of polybrominated diphenyl ethers (PBDEs) in the atmosphere of an e-waste recycling site. Chemosphere 82:1246–1252

    Article  CAS  Google Scholar 

  • Costa LG, de Laat R, Tagliaferri S, Pellacani C (2014) A mechanistic view of polybrominated diphenyl ether (PBDE) developmental neurotoxicity. Toxicol Lett 230:282–294

    Article  CAS  Google Scholar 

  • De Faria CG, Crassi M, Carvalho ACM (2011) Conformational analysis and electronic structure of chiral carbon and carbon nitride nanotubes. Mater Res 14(4):461–464

    Article  Google Scholar 

  • Fu JX, Suuberg EM (2011) Vapor pressure of solid polybrominated diphenyl ethers determined via knudsen effusion method. Environ Toxicol Chem 30:2216–2219

    Article  CAS  Google Scholar 

  • Hinckley DA, Bidleman TF, Foreman WT, Tuschall JR (1990) Determination of vapor-pressures for nonpolar and semipolar organic-compounds from gas-chromatographic retention data. J Chem Eng Data 35:232–237

    Article  CAS  Google Scholar 

  • Huang FF, Wen S, Li JG, Zhong YX, Zhao YF, Wu YN (2014) The human body burden of polybrominated diphenyl ethers and their relationships with thyroid hormones in the general population in Northern China. Sci Total Environ 466:609–615

    Article  Google Scholar 

  • Jiang CY, Zhang S, Liu HL, Zeng Q, Xia T, Chen YH, Kuang G, Zhao GD, Wu X, Zhang XF, Wang AG (2012) The role of the IRE1 pathway in PBDE-47-induced toxicity in human neuroblastoma SH-SY5Y cells in vitro. Toxicol Lett 211:325–333

    Article  CAS  Google Scholar 

  • Kim UJ, Jo H, Lee IS, Joo GJ, Oh JE (2015) Investigation of bioaccumulation and biotransformation of polybrominated diphenyl ethers, hydroxylated and methoxylated derivatives in varying trophic level freshwater fishes. Chemosphere 137:108–114

    Article  CAS  Google Scholar 

  • Kuramochi H, Takigami H, Scheringer M, Sakai S (2014) Measurement of vapor pressures of selected PBDEs, hexabromobenzene, and 1,2-bis (2,4,6-tribromophenoxy) ethane at elevated temperatures. J Chem Eng Data 59:8–15

    Article  CAS  Google Scholar 

  • Nakajoh K, Shibata E, Todoroki T, Ohara A, Nishizawa K, Nakamura T (2005) Vapor pressure of ten polychlorinated biphenyl congeners and two commercial fluids as a function of temperature. Environ Toxicol Chem 24:1602–1608

    Article  CAS  Google Scholar 

  • Nakajoh K, Shibata E, Todoroki T, Ohara A, Nishizawa K, Nakamura T (2006) Measurement of temperature dependence for the vapor pressures of twenty-six polychlorinated biphenyl congeners in commercial Kanechlor mixtures by the Knudsen effusion method. Environ Toxicol Chem 25:327–336

    Article  CAS  Google Scholar 

  • Napoli E, Hung C, Wong S, Giulivi C (2013) Toxicity of the flame-retardant BDE-49 on brain mitochondria and neuronal progenitor striatal cells enhanced by a PTEN-deficient background. Toxicol Sci 132:196–210

    Article  CAS  Google Scholar 

  • Orn U, Klasson-Wehler E (1998) Metabolism of 2,2′,4,4′-tetrabromodiphenyl ether in rat and mouse. Xenobiotica 28:199–211

    CAS  Google Scholar 

  • Qiu XH, Mercado-Feliciano M, Bigsby RM, Hites RA (2007) Measurement of polybrominated diphenyl ethers and metabolites in mouse plasma after exposure to a commercial pentabromodiphenyl ether mixture. Environ Health Perspect 115:1052–1058

    Article  CAS  Google Scholar 

  • Rydén A, Nestor G, Jakobsson K, Marsh G (2012) Synthesis and tentative identification of novel polybrominated diphenyl ether metabolites in human blood. Chemosphere 88:1127–1234

    Article  Google Scholar 

  • Stasinska A, Heyworth J, Reid A, Callan A, Odland JO, Duong PT, Ho QV, Hinwood A (2014) Polybrominated diphenyl ether (PBDE) concentrations in plasma of pregnant women from Western Australia. Sci Total Environ 493:554–561

    Article  CAS  Google Scholar 

  • Strid A, Smedje G, Athanassiadis I, Lindgren T, Lundgren H, Jakobsson K, Bergman A (2014) Brominated flame retardant exposure of aircraft personnel. Chemosphere 116:83–90

    Article  CAS  Google Scholar 

  • Wang HS, Jiang GM, Chen ZJ, Du J, Man YB, Giesy JP, Wong CKC, Wong MH (2013) Concentrations and congener profiles of polybrominated diphenyl ethers (PBDEs) in blood plasma from Hong Kong: implications for sources and exposure route. J Hazard Mater 261:253–259

    Article  CAS  Google Scholar 

  • Weijs L, Shaw SD, Berger ML, Neels H, Blust R, Covaci A (2014) Methoxylated PBDEs (MeO-PBDEs), hydroxylated PBDEs (HO-PBDEs) and hydroxylated PCBs (HO-PCBs) in the liver of harbor seals from the northwest Atlantic. Sci Total Environ 493:606–614

    Article  CAS  Google Scholar 

  • Wong KS, Law CWY, Sun T, Monkman AP, Vaschetto ME, Hartwell LJ, Horsburgh LE, Burrows HD, Miguel MD (2001) Triplet state dynamics in poly(2,5-pyridine diyl). Synth Met 116:15–18

    Article  CAS  Google Scholar 

  • Yu LQ, Liu CS, Chen Q, Zhou BS (2014) Endocrine disruption and reproduction impairment in zebrafish after long-term exposure to DE-71. Environ Toxicol Chem 33:1354–1362

    Article  CAS  Google Scholar 

  • Zhao J, Zhu XW, Xu T, Yin DQ (2015) Structure-dependent activities of polybrominated diphenyl ethers and hydroxylated metabolites on zebrafish retinoic acid receptor. Environ Sci Pollut Res 22:1723–1730

    Article  CAS  Google Scholar 

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Acknowledgments

Financial supports from the National Natural Science Foundation (21277017), the Fundamental Research Funds for the Central Universities (DUT15LK40) and the Basic Research Project of Key Laboratory of Liaoning Provincial Education Department (LZ2015023) are gratefully acknowledged.

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Authors and Affiliations

  1. Key Laboratory of Industrial Ecology and Environmental Engineering (Ministry of Education), School of Environmental Science and Technology, Dalian University of Technology, Linggong Road 2, Dalian, 116024, China

    Hongxia Zhao, Qing Xie, Xiuying Chen & Jingqiu Jiang

  2. Dalian Institute of Food Inspection, Wanshui Street 68, Dalian, 116021, China

    Baocheng Qu

Authors
  1. Hongxia Zhao
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  2. Qing Xie
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  3. Xiuying Chen
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  4. Baocheng Qu
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Correspondence to Hongxia Zhao.

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Zhao, H., Xie, Q., Chen, X. et al. Measurement of Temperature Dependence for Vapor Pressures of Seventeen OH-PBDEs and Eleven MeO-PBDEs by Gas Chromatographic Method. Bull Environ Contam Toxicol 96, 657–663 (2016). https://doi.org/10.1007/s00128-016-1778-7

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  • DOI: https://doi.org/10.1007/s00128-016-1778-7

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