- Synthesis and Toxicity of Halogenated Bisphenol Monosubstituted-Ethers: Establishing a Library for Potential Environmental Transformation Products of Emerging Contaminant
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As an important branch of halogenated bisphenol compounds, the halogenated bisphenol monosubstituted-ether compounds have received a lot of attention in environmental health science because of their toxicity and variability. In this study, a synthetic method for bisphenol monosubstituted-ether byproduct libraries was developed. By using the versatile and efficient method, tetrachlorobisphenol A, tetrabromobisphenol A, and tetrabromobisphenol S monosubstituted alkyl-ether compounds were accessed in 39–82 % yield. Subsequently, the cytotoxicity of 27 compounds were screened using three different cell lines (HepG2, mouse primary astrocytes and Chang liver cells). Compound 2,6-dibromo-4-[3,5-dibromo-4-(2-hydroxyethoxy)benzene-1-sulfonyl]phenol was more toxic than other compounds in various cells, and the sensitivity of this compound to the normal hepatocytes and cancer cells was inconsistent. The compounds 2,6-dichloro-4-(2-{3,5-dichloro-4-[(prop-2-en-1-yl)oxy]phenyl}propan-2-yl)phenol and 2,6-dibromo-4-(2-{3,5-dibromo-4-[(prop-2-en-1-yl)oxy]phenyl}propan-2-yl)phenol were the most toxic to HepG2 cells, and most of the other compounds inhibited cell proliferation. Moreover, typical compounds were also reproductive and developmental toxic to zebrafish embryos at different concentrations. The synthetic byproduct libraries could be used as pure standard compounds and applied in research on environmental behavior and the transformation of halogenated flame retardants.
- Guo, Rui,Cao, Mengxi,Hu, Ming,Deng, Wenchao,Zhang, Wenjuan,Gao, Yangguang,Ye, Shihan,Zhou, Weixiang,Shi, Jianbo
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- Efficient synthesis of various bromo bisphenol A allyl ether derivatives
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The invention provides a synthesis path of various bromo bisphenol A allyl ether derivatives. The efficient synthesis of 11 kinds of potential tetrabromo bisphenol A diallyl ether degrading byproductsis successfully completed. The path has the following advantages that (1) raw materials are cheap and can be easily obtained; the reagents are all industrial common reagents; (2) the operation is simple and convenient; the reaction conditions are mild; the yield is high; the selectivity is high; the derivatives are suitable for mass industrial preparation; (3) the synthesis path is simple and economical; products can be easily separated; the purity of the obtained 11 kinds of compounds is high. The steps are simple; the operation is convenient; the practicability is high.
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Paragraph 0068; 0070; 0076; 0077
(2018/06/14)
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- The UV/Fenton degradation of tetrabromobisphenol a catalyzed by nanocrystalline chromium substituted magnetite
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The heterogeneous UV/Fenton degradation of tetrabromobisphenol A (TBBPA) catalyzed by nanocrystalline Fe3O4and Fe2.04Cr0.96O4was investigated, with focus on the influence of UV light and initial pH, degradation pathways and effect of Cr substation. The catalysts were prepared by a precipitation-oxidation method and characterized by chemical analysis. XRD. XAFS. TG-DSC, BET surface area and magnetometer. At pH 6.7 and under UV irradiation, almost complete degradation of TBBPA by Fe2.04Cr0.96O4was accomplished within 240 min. and the leaching Fe ions were negligible. The substitution of chromium greatly increased the BET specific surface area and surface hydroxyl amount, which improved the heterogeneous UV/Fenton catalytic activity of magnetite. Moreover, Cr3+on the octahedral sites enhanced the electron transfer process in the magnetite structure to accelerate the ?OH generation. The produced ?OH radicals preferentially attacked the C-Br bonds of TBBPA and then β-cleavaged the C-C bonds between benzene rings and isopropyl groups. The above results are of great significance for well understanding the effect of transition metal substitution on the UV/Fenton catalytic activity of magnetite and prospecting the application of magnetite minerals in environmental purification.
- Zhong, Yuanhong,Liang, Xiaoliang,He, Zisen,Tan, Wei,He, Hongping,Zhu, Runliang,Zhong, Yin,Zhu, Jianxi,Yuan, Peng,Jiang, Zheng
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p. 7307 - 7314
(2015/01/16)
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- Photochemical transformations of tetrabromobisphenol A and related phenols in water
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A method was developed for studies of the phototransformation at UV irradiation of aqueous solutions of tetrabromobisphenol A (TBBPA), tribromobisphenol A (TriBBPA), tetrachlorobisphenol A (TCBPA), 2,4-dichlorophenol at various pHs as well as 2-chlorophenol, 2-bromophenol, 3,4-dichlorophenol and bisphenol A at pH 11. The absorbance spectra of the compounds and the emission spectra of the light-source were determined and used to calculate disappearance quantum yields of the photochemical reactions that were taking place. No major differences between the disappearance quantum yields of TBBPA and TCBPA were observed at pH 10, while the disappearance quantum yield of TriBBPA was approximately two times higher. The rate of decomposition of TBBPA was six times higher at pH 8 than at pH 6. Identification of the degradation products of TBBPA and TriBBPA, by GC-MS analysis and by comparison to synthesised reference compounds, indicated that TBBPA and TriBBPA decompose via different mechanisms. Three isopropylphenol derivatives; 4-isopropyl-2,6-dibromophenol, 4-isopropylene-2,6-dibromophenol and 4-(2-hydroxyisopropyl)-2,6-dibromophenol, were identified as major degradation products of TBBPA while the major degradation product of TriBBPA was tentatively identified as 2-(2,4-cyclopentadienyl)-2-(3,5-dibromo-4-hydroxyphenyl)propane.
- Eriksson, Johan,Rahm, Sara,Green, Nicholas,Bergman, Ake,Jakobsson, Eva
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p. 117 - 126
(2007/10/03)
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