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Thermal Stability and Decomposition Products of Hexabromocyclododecane
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    Thermal Stability and Decomposition Products of Hexabromocyclododecane
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    Gruppo Nazionale per la Difesa dai Rischi Chimico-Industriali ed Ecologici, Consiglio Nazionale delle Ricerche, via Diotisalvi n.2, 56126 Pisa, Italy, and Dipartimento di Ingegneria Chimica, Chimica Industriale e Scienza dei Materiali, Università degli Studi di Pisa, via Diotisalvi n.2, 56126 Pisa, Italy
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    Industrial & Engineering Chemistry Research

    Cite this: Ind. Eng. Chem. Res. 2001, 40, 15, 3270–3280
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    https://doi.org/10.1021/ie001002v
    Published June 23, 2001
    Copyright © 2001 American Chemical Society

    Abstract

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    The thermal stability and decomposition products of hexabromocyclododecane (HBCD), a widely used aliphatic brominated flame retardant, were investigated. HBCD thermal degradation was carried out in nitrogen and in air at moderate heating rates (10 °C/min) using thermogravimetric analyzers and a laboratory-scale fixed-bed reactor. The identification of decomposition products was based mainly on FTIR and gas-chromatographic/mass-spectrometric techniques. Quantitative data on hydrogen bromide formation and on the bromine distribution among the different product fractions were obtained. For the experimental conditions used in this study, about 75 wt % of the bromine is released as HBr, and 25 wt % is involved in the formation of high-molecular-weight bromo-organic compounds. The main pathways of HBCD thermal degradation were assessed, and a global mechanism for HBCD decomposition was proposed.

    Copyright © 2001 American Chemical Society

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     Consiglio Nazionale delle Ricerche.

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     Author to whom correspondence should be addressed. Tel.:  (+39)-050-511212. Fax:  (+39)-050-511266. E-mail:  [email protected].

     Università degli Studi di Pisa.

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    4. Nycolle G. S. Silva Noelle C. Zanini Alana G. de Souza Rennan F. S. Barbosa Derval S. Rosa Daniella R. Mulinari . Halogen-Based Flame Retardants in Polyurethanes. , 141-171. https://doi.org/10.1021/bk-2021-1399.ch007
    5. Mark W. Beach, Kenneth L. Kearns, John W. Davis, John R. Stutzman, Dean Lee, Yuming Lai, Daria Monaenkova, Shari Kram, Jing Hu, Christine Lukas. Stability Assessment of a Polymeric Brominated Flame Retardant in Polystyrene Foams under Application-Relevant Conditions. Environmental Science & Technology 2021, 55 (5) , 3050-3058. https://doi.org/10.1021/acs.est.0c04325
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    7. Philip H. Howard and Derek C. G. Muir . Identifying New Persistent and Bioaccumulative Organics Among Chemicals in Commerce. III: Byproducts, Impurities, and Transformation Products. Environmental Science & Technology 2013, 47 (10) , 5259-5266. https://doi.org/10.1021/es4004075
    8. Mi Tian, She-Jun Chen, Jing Wang, Tian Shi, Xiao-Jun Luo, and Bi-Xian Mai . Atmospheric Deposition of Halogenated Flame Retardants at Urban, E-Waste, and Rural Locations in Southern China. Environmental Science & Technology 2011, 45 (11) , 4696-4701. https://doi.org/10.1021/es200112m
    9. Jiang-Ping Wu, Yun-Tao Guan, Ying Zhang, Xiao-Jun Luo, Hui Zhi, She-Jun Chen and Bi-Xian Mai. Trophodynamics of Hexabromocyclododecanes and Several Other Non-PBDE Brominated Flame Retardants in a Freshwater Food Web. Environmental Science & Technology 2010, 44 (14) , 5490-5495. https://doi.org/10.1021/es101300t
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    11. Sicco H. Brandsma, Leo T.M. van der Ven, Jacob de Boer and Pim E.G. Leonards . Identification of Hydroxylated Metabolites of Hexabromocyclododecane in Wildlife and 28-days Exposed Wistar Rats. Environmental Science & Technology 2009, 43 (15) , 6058-6063. https://doi.org/10.1021/es900879k
    12. Zhiqiang Yu, Laiguo Chen, Bixian Mai, Minghong Wu, Guoying Sheng, Jiamo Fu and Ping’an Peng . Diastereoisomer- and Enantiomer-specific Profiles of Hexabromocyclododecane in the Atmosphere of an Urban City in South China. Environmental Science & Technology 2008, 42 (11) , 3996-4001. https://doi.org/10.1021/es7027857
    13. Josef Hiebl and, Walter Vetter. Detection of Hexabromocyclododecane and Its Metabolite Pentabromocyclododecene in Chicken Egg and Fish from the Official Food Control. Journal of Agricultural and Food Chemistry 2007, 55 (9) , 3319-3324. https://doi.org/10.1021/jf063428b
    14. Enrico Biagini,, Federica Barontini, and, Leonardo Tognotti. Devolatilization of Biomass Fuels and Biomass Components Studied by TG/FTIR Technique. Industrial & Engineering Chemistry Research 2006, 45 (13) , 4486-4493. https://doi.org/10.1021/ie0514049
    15. Federica Barontini,, Katia Marsanich,, Luigi Petarca, and, Valerio Cozzani. Thermal Degradation and Decomposition Products of Electronic Boards Containing BFRs. Industrial & Engineering Chemistry Research 2005, 44 (12) , 4186-4199. https://doi.org/10.1021/ie048766l
    16. Federica Barontini,, Katia Marsanich,, Luigi Petarca, and, Valerio Cozzani. The Thermal Degradation Process of Tetrabromobisphenol A. Industrial & Engineering Chemistry Research 2004, 43 (9) , 1952-1961. https://doi.org/10.1021/ie034017c
    17. Hanene Oumeddour, Hussam Aldoori, Zohra Bouberka, Venkateswara Rao Mundlapati, Vikas Madhur, Corinne Foissac, Philippe Supiot, Yvain Carpentier, Michael Ziskind, Cristian Focsa, Ulrich Maschke. Degradation processes of brominated flame retardants dispersed in high impact polystyrene under UV–visible radiation. Waste Management & Research: The Journal for a Sustainable Circular Economy 2024, 42 (12) , 1241-1252. https://doi.org/10.1177/0734242X231219626
    18. Tuomas Sormunen, Ilkka Rytöluoto, Anna Tenhunen-Lunkka, Francisco Senna Vieira. Raman spectroscopy combined with active hyperspectral sensing for classification of waste plastics containing brominated flame retardants: A sensor fusion approach. Waste Management & Research: The Journal for a Sustainable Circular Economy 2024, 60 https://doi.org/10.1177/0734242X241287736
    19. Jian Wang, Bingcheng Lin, Xiao Wang, Guorui Liu, Rong Jin, Jukun Xiong, Jianping Guo, Yinming Li, Minghui Zheng. Emission, distribution and formation characteristics of polybrominated dibenzo-p-dioxins and dibenzofurans during co-disposal of hexabromocyclododecane-containing waste in cement kiln. Science of The Total Environment 2024, 953 , 176168. https://doi.org/10.1016/j.scitotenv.2024.176168
    20. Chenchen Huang, Kelan Guan, Xuemeng Qi, Yin-E Liu, Qihong Lu, Yanhong Zeng, Shanquan Wang, Xiaojun Luo, Bixian Mai. Spatial distribution, conversion, and ecological risk assessment of hexabromocyclododecanes in the sediments of black-odorous urban rivers nationwide in China. Science of The Total Environment 2024, 907 , 168057. https://doi.org/10.1016/j.scitotenv.2023.168057
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    24. Vincent N Mokoana, Joseph KO Asante, O Jonathan Okonkwo. A review on volatilization of flame retarding compounds from polymeric textile materials used in firefighter protective garment. Journal of Fire Sciences 2023, 41 (4) , 107-121. https://doi.org/10.1177/07349041231171349
    25. Maria Lopes Marques, Elisa Cairrao. Occurrence and Health Effects of Hexabromocyclododecane: An Updated Review. Toxics 2023, 11 (5) , 409. https://doi.org/10.3390/toxics11050409
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    27. Jiawen CHENG, Jiping MA, Shuang LI, Yong TIAN. Progress in sample pretreatment and detection methods of hexabromocyclododecanes. Chinese Journal of Chromatography 2022, 40 (10) , 872-881. https://doi.org/10.3724/SP.J.1123.2022.03030
    28. Tamaki Sato, Kazuhiro Tobiishi, Tsuguhide Hori, Tomoaki Tsutsumi, Hiroshi Akiyama, Toshiro Matsui. Simultaneous Determination of Hexabromocyclododecanes, Polybrominated Diphenyl Ethers, and Dechlorane-Related Compounds in Boxed Sushi Meals Using a Newly Developed Analytical Method. SSRN Electronic Journal 2022, 53 https://doi.org/10.2139/ssrn.4156484
    29. Joana Feiteiro, Melissa Mariana, Elisa Cairrão. Health toxicity effects of brominated flame retardants: From environmental to human exposure. Environmental Pollution 2021, 285 , 117475. https://doi.org/10.1016/j.envpol.2021.117475
    30. Tzu-Ho Chou, Yi-Jie Li, Chi-Fong Ko, Tien-Yu Wu, Yang-hsin Shih. Efficient hexabromocyclododecane-biodegrading microorganisms isolated in Taiwan. Chemosphere 2021, 271 , 129544. https://doi.org/10.1016/j.chemosphere.2021.129544
    31. Alina M. Simion, Yoshiharu Mitoma, Cristian Simion. Biota Debromination in Aqueous Media. 2021, 137-185. https://doi.org/10.1016/B978-0-12-821881-5.00007-6
    32. Shengtao Ma, Yingxin Yu, Yan Yang, Guiying Li, Taicheng An. A new advance in the potential exposure to “old” and “new” halogenated flame retardants in the atmospheric environments and biota: From occurrence to transformation products and metabolites. Critical Reviews in Environmental Science and Technology 2020, 50 (19) , 1935-1983. https://doi.org/10.1080/10643389.2019.1681051
    33. Tse-Hao Chang, Reuben Wang, Yu-Huei Peng, Tzu-Ho Chou, Yi-Jie Li, Yang-hsin Shih. Biodegradation of hexabromocyclododecane by Rhodopseudomonas palustris YSC3 strain: A free-living nitrogen-fixing bacterium isolated in Taiwan. Chemosphere 2020, 246 , 125621. https://doi.org/10.1016/j.chemosphere.2019.125621
    34. Li Li. Effective Management of Demolition Waste Containing Hexabromocyclododecane in China. 2020, 99-111. https://doi.org/10.1007/978-981-15-0579-9_6
    35. Yuan Gao, Rong Cao, Haijun Zhang, Jiping Chen. Analysis of emerging halogenated flame retardants in environment. 2020, 41-70. https://doi.org/10.1016/bs.coac.2019.10.007
    36. Jin-Woo Jeon, Chul-Su Kim, Leesun Kim, Sung-Eun Lee, Ho-Joong Kim, Chang-Ho Lee, Sung-Deuk Choi. Distribution and diastereoisomeric profiles of hexabromocyclododecanes in air, water, soil, and sediment samples in South Korea: Application of an optimized analytical method. Ecotoxicology and Environmental Safety 2019, 181 , 321-329. https://doi.org/10.1016/j.ecoenv.2019.06.015
    37. Juhyeon Lee, Yukito Urakawa, Suguru Motokucho, Hisayuki Nakatani. Selective decomposition of hexabromocyclododecane in polystyrene and recyclability improvement of its polymeric component. Polymer Degradation and Stability 2019, 166 , 40-49. https://doi.org/10.1016/j.polymdegradstab.2019.05.016
    38. Mingge Wu, Yanhui Zhao, Qianqian Li, Guijin Su, Wenbin Liu, Qingliang Wang, Chuanqi Li. Thermal catalytic degradation of α-HBCD, β-HBCD and γ-HBCD over Fe3O4 micro/nanomaterial: Kinetic behavior, product analysis and mechanism hypothesis. Science of The Total Environment 2019, 668 , 1200-1212. https://doi.org/10.1016/j.scitotenv.2019.03.064
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    40. Mohammednoor Altarawneh, Anam Saeed, Mohammad Al-Harahsheh, Bogdan Z. Dlugogorski. Thermal decomposition of brominated flame retardants (BFRs): Products and mechanisms. Progress in Energy and Combustion Science 2019, 70 , 212-259. https://doi.org/10.1016/j.pecs.2018.10.004
    41. Krzysztof Okonski, Lisa Melymuk, Jiří Kohoutek, Jana Klánová. Hexabromocyclododecane: concentrations and isomer profiles from sources to environmental sinks. Environmental Science and Pollution Research 2018, 25 (36) , 36624-36635. https://doi.org/10.1007/s11356-018-3381-4
    42. Song-Yee Baek, Byungjoo Kim, Sunyoung Lee, Joonhee Lee, Seonghee Ahn. Accurate determination of hexabromocyclododecane diastereomers in extruded high-impact polystyrene: Development of an analytical method as a candidate reference method. Chemosphere 2018, 210 , 296-303. https://doi.org/10.1016/j.chemosphere.2018.06.127
    43. Xiuji Wang, Shufen He, Guanhai Wang, Yanchun Wang, Ying Cai, Pei Chen, Jun Mei. Characterization of PBDD/F emissions from simulated polystyrene insulation foam via lab-scale programmed thermal treatment testing. Chemosphere 2018, 211 , 926-933. https://doi.org/10.1016/j.chemosphere.2018.08.026
    44. Xueli Wang, Xiaoyu Yuan, Shengke Yang, Yaqian Zhao. Concentrations, Distributions, and Risk Assessment of HBCD in Sediment in the Weihe River Basin in Northwest China. International Journal of Environmental Research and Public Health 2018, 15 (11) , 2340. https://doi.org/10.3390/ijerph15112340
    45. Yan Li, Xiuhua Zhu, Longxing Wang, Yuan Gao, Jiping Chen, Wei Wang, Xuewei Dong, Xiaoxiao Li. Levels and gas-particle partitioning of hexabromocyclododecanes in the urban air of Dalian, China. Environmental Science and Pollution Research 2018, 25 (27) , 27514-27523. https://doi.org/10.1007/s11356-018-2793-5
    46. Yu-Huei Peng, Ya-jou Chen, Ming Chang, Yang-hsin Shih. The effect of zerovalent iron on the microbial degradation of hexabromocyclododecane. Chemosphere 2018, 200 , 419-426. https://doi.org/10.1016/j.chemosphere.2018.02.123
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    48. Xianghui Cao, Yonglong Lu, Yueqing Zhang, Kifayatullah Khan, Chenchen Wang, Yvette Baninla. An overview of hexabromocyclododecane (HBCDs) in environmental media with focus on their potential risk and management in China. Environmental Pollution 2018, 236 , 283-295. https://doi.org/10.1016/j.envpol.2018.01.040
    49. Yu Zhang, Minggang Zheng, Ling Wang, Yinghua Lou, Lei Shi, Runhui Ke, Bingui Wang. High level of tris-(2,3-dibromopropyl) isocyanurate (TBC) and hexabromocyclododecanes (HBCDs) in sediments from the intertidal zone of New River Estuary—a polluted and degraded wetland. Marine Pollution Bulletin 2018, 130 , 287-292. https://doi.org/10.1016/j.marpolbul.2018.03.045
    50. Jin-Peng Yuan, Zhao-Jie Cui, Chuan-Ge Cheng, Xiao-Li Wang, Shan-Shan Wang, Xin-Li Song, Fu-Wei Li. Rapid and simultaneous determination of tetrabromobisphenol A and hexabromocyclododecane diastereoisomers in soil by matrix solid-phase dispersion with bamboo charcoal as dispersive adsorbent. Acta Chromatographica 2017, 29 (4) , 487-492. https://doi.org/10.1556/1326.2016.00122
    51. Manviri Rani, Won Joon Shim, Mi Jang, Gi Myung Han, Sang Hee Hong. Releasing of hexabromocyclododecanes from expanded polystyrenes in seawater -field and laboratory experiments. Chemosphere 2017, 185 , 798-805. https://doi.org/10.1016/j.chemosphere.2017.07.042
    52. Saki Arita, Kanae Yamaguchi, Suguru Motokucho, Hisayuki Nakatani. Selective decomposition of hexabromocyclododecane in polystyrene with a photo and thermal hybrid treatment system. Polymer Degradation and Stability 2017, 143 , 130-135. https://doi.org/10.1016/j.polymdegradstab.2017.07.003
    53. Yuji Ukisu. Complete catalytic debromination of hexabromocyclododecane using a silica-supported palladium catalyst in alkaline 2-propanol. Chemosphere 2017, 179 , 179-184. https://doi.org/10.1016/j.chemosphere.2017.03.111
    54. Ling Wang, Mengyuan Zhang, Yinghua Lou, Runhui Ke, Minggang Zheng. Levels and distribution of tris-(2,3-dibromopropyl) isocyanurate and hexabromocyclododecanes in surface sediments from the Yellow River Delta wetland of China. Marine Pollution Bulletin 2017, 114 (1) , 577-582. https://doi.org/10.1016/j.marpolbul.2016.09.019
    55. Mark W. Beach, John W. Hull, Bruce A. King, Inken I. Beulich, Bill G. Stobby, Shari L. Kram, Dave B. Gorman. Development of a new class of brominated polymeric flame retardants based on copolymers of styrene and polybutadiene. Polymer Degradation and Stability 2017, 135 , 99-110. https://doi.org/10.1016/j.polymdegradstab.2016.11.008
    56. Ling Wang, Quansheng Zhao, Yanyan Zhao, Yinghua Lou, Minggang Zheng, Yue Yu, Mengyuan Zhang. Determination of heterocyclic brominated flame retardants tris-(2, 3-dibromopropyl) isocyanurate and hexabromocyclododecane in sediment from Jiaozhou Bay wetland. Marine Pollution Bulletin 2016, 113 (1-2) , 509-512. https://doi.org/10.1016/j.marpolbul.2016.08.013
    57. Fang Li, Jing Jin, Dongqin Tan, Longxing Wang, Ningbo Geng, Rong Cao, Yuan Gao, Jiping Chen. Hexabromocyclododecane and tetrabromobisphenol A in sediments and paddy soils from Liaohe River Basin, China: Levels, distribution and mass inventory. Journal of Environmental Sciences 2016, 48 , 209-217. https://doi.org/10.1016/j.jes.2016.03.018
    58. Ayesha Kausar, Irum Rafique, Zanib Anwar, Bakhtiar Muhammad. Recent Developments in Different Types of Flame Retardants and Effect on Fire Retardancy of Epoxy Composite. Polymer-Plastics Technology and Engineering 2016, 55 (14) , 1512-1535. https://doi.org/10.1080/03602559.2016.1163607
    59. Chuan Ma, Jie Yu, Ben Wang, Zijian Song, Jun Xiang, Song Hu, Sheng Su, Lushi Sun. Chemical recycling of brominated flame retarded plastics from e-waste for clean fuels production: A review. Renewable and Sustainable Energy Reviews 2016, 61 , 433-450. https://doi.org/10.1016/j.rser.2016.04.020
    60. Giovanni Cagnetta, Han Liu, Kunlun Zhang, Jun Huang, Bin Wang, Shubo Deng, Yujue Wang, Gang Yu. Mechanochemical conversion of brominated POPs into useful oxybromides: a greener approach. Scientific Reports 2016, 6 (1) https://doi.org/10.1038/srep28394
    61. Yingtan Yu, Danna Zhou, Feng Wu. Mechanism and products of the photolysis of hexabromocyclododecane in acetonitrile–water solutions under a UV-C lamp. Chemical Engineering Journal 2015, 281 , 892-899. https://doi.org/10.1016/j.cej.2015.07.031
    62. Hui Zhang, Stéphane Bayen, Barry C. Kelly. Co-extraction and simultaneous determination of multi-class hydrophobic organic contaminants in marine sediments and biota using GC-EI-MS/MS and LC-ESI-MS/MS. Talanta 2015, 143 , 7-18. https://doi.org/10.1016/j.talanta.2015.04.084
    63. Liang Tang, Hai-Yang Shao, Jian-Yao Zhu, Gang Xu, Tao Han, Bing-Quan Peng, Ming-Hong Wu. Hexabromocyclododecane diastereoisomers in surface sediments from river drainage basins of Shanghai, China: occurrence, distribution, and mass inventory. Environmental Science and Pollution Research 2015, 22 (16) , 11993-12000. https://doi.org/10.1007/s11356-015-4336-7
    64. Huan Liu, Xiaodong Wang, Dezhen Wu. Synthesis of a novel linear polyphosphazene-based epoxy resin and its application in halogen-free flame-resistant thermosetting systems. Polymer Degradation and Stability 2015, 118 , 45-58. https://doi.org/10.1016/j.polymdegradstab.2015.04.009
    65. Monica Mattarozzi, Maria Careri. Liquid Chromatography/Mass Spectrometry in Environmental Analysis. 2015, 1-41. https://doi.org/10.1002/9780470027318.a0840.pub2
    66. Liesbeth Weijs, Alin C. Dirtu, Govindan Malarvannan, Adrian Covaci. Bioaccumulation and Biotransformation of Brominated Flame Retardants. 2015, 433-491. https://doi.org/10.1016/B978-0-444-63299-9.00014-4
    67. Kunlun Zhang, Jun Huang, Haizhu Wang, Kai Liu, Gang Yu, Shubo Deng, Bin Wang. Mechanochemical degradation of hexabromocyclododecane and approaches for the remediation of its contaminated soil. Chemosphere 2014, 116 , 40-45. https://doi.org/10.1016/j.chemosphere.2014.02.006
    68. Manviri Rani, Won Joon Shim, Gi Myung Han, Mi Jang, Young Kyoung Song, Sang Hee Hong. Hexabromocyclododecane in polystyrene based consumer products: An evidence of unregulated use. Chemosphere 2014, 110 , 111-119. https://doi.org/10.1016/j.chemosphere.2014.02.022
    69. Ming-Hong Wu, Jian-Yao Zhu, Liang Tang, Ning Liu, Bing-Quan Peng, Rui Sun, Gang Xu. Hexabromocyclododecanes in surface sediments from Shanghai, China: Spatial distribution, seasonal variation and diastereoisomer-specific profiles. Chemosphere 2014, 111 , 304-311. https://doi.org/10.1016/j.chemosphere.2014.04.031
    70. Jung Keun Oh, Kensuke Kotani, Satoshi Managaki, Shigeki Masunaga. Levels and distribution of hexabromocyclododecane and its lower brominated derivative in Japanese riverine environment. Chemosphere 2014, 109 , 157-163. https://doi.org/10.1016/j.chemosphere.2014.01.074
    71. Qian Han, Han Song, Shutao Gao, Xiangying Zeng, Zhiqiang Yu, Yunjiang Yu, Guoying Sheng, Jiamo Fu. Determination of ten hexabromocyclododecane diastereoisomers using two coupled reversed‐phase columns and liquid chromatography/tandem mass spectrometry. Rapid Communications in Mass Spectrometry 2014, 28 (13) , 1473-1478. https://doi.org/10.1002/rcm.6922
    72. Gabriele Landucci, Gianfranco Lovicu, Federica Barontini, Luca Guidi, Cristiano Nicolella. Safety issues related to the maintenance operations in a vegetable oil refinery: A case study. Journal of Loss Prevention in the Process Industries 2014, 30 , 95-104. https://doi.org/10.1016/j.jlp.2014.05.005
    73. Elizabeth R. Wagoner, Clark P. Baumberger, Benjamin H.R. Gerroll, Dennis G. Peters. Catalytic reduction of 1,2,5,6,9,10-hexabromocyclododecane by nickel(I) salen electrogenerated at vitreous carbon cathodes in dimethylformamide. Electrochimica Acta 2014, 132 , 545-550. https://doi.org/10.1016/j.electacta.2014.03.162
    74. C. Pasturenzi, M. Dellavedova, L. Gigante, A. Lunghi, M. Canavese, C. Sala Cattaneo, S. Copelli. Thermochemical stability: A comparison between experimental and predicted data. Journal of Loss Prevention in the Process Industries 2014, 28 , 79-91. https://doi.org/10.1016/j.jlp.2013.03.011
    75. Alin C. Dirtu, Alin C. Ionas, Govindan Malarvannan, Adrian Covaci. Transformation Products of Brominated Flame Retardants (BFRs). 2014, 545-576. https://doi.org/10.1002/9781118339558.ch18
    76. Elizabeth R. Wagoner, Clark P. Baumberger, Angela A. Peverly, Dennis G. Peters. Electrochemical reduction of 1,2,5,6,9,10-hexabromocyclododecane at carbon and silver cathodes in dimethylformamide. Journal of Electroanalytical Chemistry 2014, 713 , 136-142. https://doi.org/10.1016/j.jelechem.2013.11.033
    77. Jianfeng Tang, Jiayong Feng, Xinhu Li, Gang Li. Levels of flame retardants HBCD, TBBPA and TBC in surface soils from an industrialized region of East China. Environ. Sci.: Processes Impacts 2014, 16 (5) , 1015-1021. https://doi.org/10.1039/C3EM00656E
    78. Nali Zhu, Jianjie Fu, Yan Gao, Patrick Ssebugere, Yawei Wang, Guibin Jiang. Hexabromocyclododecane in alpine fish from the Tibetan Plateau, China. Environmental Pollution 2013, 181 , 7-13. https://doi.org/10.1016/j.envpol.2013.05.050
    79. Man Teng, Jing Jin, Qiang Fu, YaQi Cai, JiPing Chen, FuSheng Wei. Selective separation of polychlorinated naphthalene (PCNs), hexabromocyclododecanes (HBCDs) and tetrabromobisphenol A (TBBPA) in soil matrices. Chinese Science Bulletin 2013, 58 (4-5) , 500-506. https://doi.org/10.1007/s11434-012-5638-5
    80. Natsuko Kajiwara, Jennifer Desborough, Stuart Harrad, Hidetaka Takigami. Photolysis of brominated flame retardants in textiles exposed to natural sunlight. Environmental Science: Processes & Impacts 2013, 15 (3) , 653. https://doi.org/10.1039/c3em30887a
    81. Huiru Li, Ligui Mo, Zhiqiang Yu, Guoying Sheng, Jiamo Fu. Levels, isomer profiles and chiral signatures of particle-bound hexabromocyclododecanes in ambient air around Shanghai, China. Environmental Pollution 2012, 165 , 140-146. https://doi.org/10.1016/j.envpol.2012.02.015
    82. Jinxia Fu, Eric M. Suuberg. Vapor pressure of three brominated flame retardants determined by using the Knudsen effusion method. Environmental Toxicology and Chemistry 2012, 31 (3) , 574-578. https://doi.org/10.1002/etc.1736
    83. Xiang-Zhou Meng, Yan-Ping Duan, Chao Yang, Zhao-Yu Pan, Zhi-Hao Wen, Ling Chen. Occurrence, sources, and inventory of hexabromocyclododecanes (HBCDs) in soils from Chongming Island, the Yangtze River Delta (YRD). Chemosphere 2011, 82 (5) , 725-731. https://doi.org/10.1016/j.chemosphere.2010.10.091
    84. Liming Wang, Yanfen Liu. The enthalpies of formation of brominated benzenes and phenols: A theoretical prediction. Journal of Molecular Structure: THEOCHEM 2010, 957 (1-3) , 72-76. https://doi.org/10.1016/j.theochem.2010.07.009
    85. Jiayong Feng, Yawei Wang, Ting Ruan, Guangbo Qu, Guibin Jiang. Simultaneous determination of hexabromocyclododecanes and tris (2,3-dibromopropyl) isocyanurate using LC–APCI-MS/MS. Talanta 2010, 82 (5) , 1929-1934. https://doi.org/10.1016/j.talanta.2010.08.014
    86. Prafulla Kumar Sahoo. Biodegradable Polymer–Clay Nanocomposite Fire Retardants via Emulsifier-free Emulsion Polymerization. 2010, 124-141. https://doi.org/10.1039/9781849732192-00124
    87. Paula Guerra, Ethel Eljarrat, Damià Barceló. Simultaneous determination of hexabromocyclododecane, tetrabromobisphenol A, and related compounds in sewage sludge and sediment samples from Ebro River basin (Spain). Analytical and Bioanalytical Chemistry 2010, 397 (7) , 2817-2824. https://doi.org/10.1007/s00216-010-3670-3
    88. Norbert V. Heeb, Heidi Graf, W. Bernd Schweizer, P. Lienemann. Thermally-induced transformation of hexabromocyclo dodecanes and isobutoxypenta bromocyclododecanes in flame-proofed polystyrene materials. Chemosphere 2010, 80 (7) , 701-708. https://doi.org/10.1016/j.chemosphere.2010.05.034
    89. Ya-Ying Zhao, Xi-Hui Zhang, O.S. Samuel Sojinu. Thermodynamics and photochemical properties of α, β, and γ-hexabromocyclododecanes: A theoretical study. Chemosphere 2010, 80 (2) , 150-156. https://doi.org/10.1016/j.chemosphere.2010.04.002
    90. Gi Beum Kim, Heather M. Stapleton. PBDEs, methoxylated PBDEs and HBCDs in Japanese common squid (Todarodes pacificus) from Korean offshore waters. Marine Pollution Bulletin 2010, 60 (6) , 935-940. https://doi.org/10.1016/j.marpolbul.2010.03.025
    91. Espen Mariussen, Marianne Haukås, Hans Peter H. Arp, Kai-Uwe Goss, Anders Borgen, Torkjel M. Sandanger. Relevance of 1,2,5,6,9,10-hexabromocyclododecane diastereomer structure on partitioning properties, column-retention and clean-up procedures. Journal of Chromatography A 2010, 1217 (9) , 1441-1446. https://doi.org/10.1016/j.chroma.2009.12.076
    92. P. Guerra, A. Covaci, E. Eljarrat, D. Barceló. Recent Methodologies for Brominated Flame Retardant Determinations by Means of Liquid Chromatography–Mass Spectrometry. 2010, 95-121. https://doi.org/10.1007/698_2010_94
    93. E. Eljarrat, D. Raldúa, D. Barceló. Origin, Occurrence, and Behavior of Brominated Flame Retardants in the Ebro River Basin. 2010, 167-187. https://doi.org/10.1007/698_2010_70
    94. Mauro Cordella, Alessandro Tugnoli, Federica Barontini, Gigliola Spadoni, Valerio Cozzani. Inherent safety of substances: Identification of accidental scenarios due to decomposition products. Journal of Loss Prevention in the Process Industries 2009, 22 (4) , 455-462. https://doi.org/10.1016/j.jlp.2009.02.015
    95. Paula Guerra, Agustina De La Cal, Göran Marsh, Ethel Eljarrat, Damià Barceló. Transfer of hexabromocyclododecane from industrial effluents to sediments and biota: Case study in Cinca river (Spain). Journal of Hydrology 2009, 369 (3-4) , 360-367. https://doi.org/10.1016/j.jhydrol.2009.02.024
    96. Jana Pulkrabová, Petra Hrádková, Jana Hajšlová, Jan Poustka, Michaela Nápravníková, Václav Poláček. Brominated flame retardants and other organochlorine pollutants in human adipose tissue samples from the Czech Republic. Environment International 2009, 35 (1) , 63-68. https://doi.org/10.1016/j.envint.2008.08.001
    97. Paula Guerra, Ethel Eljarrat, Damià Barceló. Enantiomeric specific determination of hexabromocyclododecane by liquid chromatography–quadrupole linear ion trap mass spectrometry in sediment samples. Journal of Chromatography A 2008, 1203 (1) , 81-87. https://doi.org/10.1016/j.chroma.2008.07.027
    98. Zhiqiang Yu, Ping’an Peng, Guoying Sheng, Jiamo Fu. Determination of hexabromocyclododecane diastereoisomers in air and soil by liquid chromatography–electrospray tandem mass spectrometry. Journal of Chromatography A 2008, 1190 (1-2) , 74-79. https://doi.org/10.1016/j.chroma.2008.02.082
    99. Mohamed Abou-Elwafa Abdallah, Catalina Ibarra, Hugo Neels, Stuart Harrad, Adrian Covaci. Comparative evaluation of liquid chromatography–mass spectrometry versus gas chromatography–mass spectrometry for the determination of hexabromocyclododecanes and their degradation products in indoor dust. Journal of Chromatography A 2008, 1190 (1-2) , 333-341. https://doi.org/10.1016/j.chroma.2008.03.006
    100. Line S. Haug, Cathrine Thomsen, Veronica H. Liane, Georg Becher. Comparison of GC and LC determinations of hexabromocyclododecane in biological samples – Results from two interlaboratory comparison studies. Chemosphere 2008, 71 (6) , 1087-1092. https://doi.org/10.1016/j.chemosphere.2007.10.044
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    Cite this: Ind. Eng. Chem. Res. 2001, 40, 15, 3270–3280
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    https://doi.org/10.1021/ie001002v
    Published June 23, 2001
    Copyright © 2001 American Chemical Society

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