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Analytical Methods · 2014 ·Vol. 6 ·期 10 ·3285-3290 · IF 1.938

Cloud point extraction for the determination of bisphenol A, bisphenol AF and tetrabromobisphenol A in river water samples by high-performance liquid chromatography

Yingtang Li,Chao Yang,Jinyan Ning,Yaling Yang

In this work, cloud point extraction (CPE) was developed for the preconcentration and separation of bisphenol A (BPA), bisphenol AF (BPAF) and tetrabromobisphenol A (TBBPA) prior to high-performance liquid chromatography (HPLC) analysis. Firstly, alcohol ethoxylate (AEO9) was applied as the extractant and octanol worked as the cloud point revulsant and synergic reagent for extraction, which decreased the cloud point temperature (CPT) of AEO9 from 75 °C to 30 °C and assisted the subsequent extraction. The parameters influencing the CPE efficiency, such as AEO9 concentration, octanol volume, pH value, extraction time and temperature were systematically evaluated. Under the optimum conditions, the linear range of BPA, BPAF and TBBPA was from 0.05 to 25 mg L−1. All correlation coefficients of the calibration curves were more than 0.9988. The relative standard deviations (RSD, n = 5) were 1.6–4.7%. The limits of detection (LOD) were in the range of 0.27–0.32 μg L−1 and the limits of quantification (LOQ) were in the range of 0.71–0.98 μg L−1. The proposed method was successfully applied to the extraction of BPA, BPAF and TBBPA in river water samples as a rapid, simple, and sensitive method.

研究领域: 分析化学 · 环境科学
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TALANTA · 2013 · IF 3.498

Preparation of a hollow porous molecularly imprinted polymer using tetrabromobisphenol A as a dummy template and its application as SPE sorbent for determination of bisphenol A in tap water

Jin Li,Xuebin Zhang,Yuxin Liu,Hongwu Tong,Yeping Xu,Shaomin Liu

In this paper, a highly selective sample cleanup procedure combing dummy molecular imprinting and solid-phase extraction (DMIP–SPE) was developed for the isolation and determination of bisphenol A (BPA) in tap water. The novel hollow porous dummy molecularly imprinted polymer (HPDMIP) was prepared adopting a sacrificial support approach, using tetrabromobisphenol A (TBBPA), whose structure was similar to that of BPA, as the dummy template and mesoporous MCM-48 nanospheres as the support. Owing to a very short distance between the binding sites and the surface, a large surface area and a good steric structure to match its imprint molecules, the maximum adsorption capacities ( Q max ) of the dummy-imprinted and non-imprinted sorbents for BPA were as high as 445 and 340   μmol   g –1 , respectively, and the adsorption reached about 73% of Q max in 10   min. Meanwhile, a method was developed for the determination of BPA using HPDMIP as a solid-phase extraction enrichment sorbent coupled with HPLC . Under the optimum experimental conditions, HPDMIP exhibited satisfactory results in the enrichment and determination of BPA in tap water with a recovery rate of 95–105%, and relative standard deviations of below 6%, and it can achieve a limit of detection as low as 3   ng   mL −1 . The developed extraction protocol eliminated the effect of template leakage on quantitative analysis and could be applied for the determination of BPA in complicated functional samples.

研究领域: 环境科学 · 分析化学
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NEW JOURNAL OF CHEMISTRY · 2024 · IF 2.7

Highly dispersed Ru immobilized on Ni-modified Al2O3 for selective hydrogenation of bisphenol A to hydrogenated bisphenol A

Shufeng Lin,Zhonghua Sun,Zhenzhen Wang,Qiumin Zhou,Anwei Wang,zhong wu,Junfeng Qian,Ming-Yang He,Qun Chen

Bisphenol A (BPA) is ubiquitous in industrial production and daily life. However, BPA is harmful to the health of fetuses and children due to its potential endocrine-disrupting effects. Hydrogenated bisphenol A (HBPA), an alicyclic diol generated from hydrogenating the double bonds of two benzene rings in the BPA molecule, is supposed to be a perfect substitute for BPA due to its stability and non-toxicity. Nevertheless, the rational design of high-performance catalysts for selectively converting BPA into HBPA remains a significant challenge. In this work, highly dispersed Ru immobilized by Al2O3 modified with Ni promoter (Ru/Ni-Al2O3) have been constructed, enabling BPA selective hydrogenation to produce HBPA under mild conditions. The doping of Ni promoter around Ru active sites effectively regulated the selectivity of target reaction. Both characterization and experimental results validated that the Ni promoter manipulated the electronic state of Ru through strong electron interaction between Ni and Ru, and thus the catalytic performance. In addition, the catalytic performance was also dependent on other reaction parameters such as H2 pressure, reaction temperature, liquid hourly space velocity (LHSV), and hydrogen-oil volume ratio. The optimized Ru/0.1Ni-Al2O3 catalyst achieved a BPA conversion of 100% and an HBPA selectivity of 96.4% under optimal reaction conditions (6 MPa H2, 140 oC, 0.42 h-1 LHSV, and 1500:1 hydrogen-oil volume ratio).

研究领域: 催化化学 · 环境科学 · 材料科学
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ANALYTICAL LETTERS · 2015 · IF 1.03

Rapid Determination of Phenolics in Food Packaging by Magnetic Solid-Phase Extraction and High-Performance Liquid Chromatography

Shuangqiao Ju,Yaling Yang,Mousheng Liu

A method for magnetic solid-phase extraction was developed for the preconcentration of bisphenol A, bisphenol AF, tetrabromobisphenol A, and 4-tert-octylphenol from food containers and packaging materials. Cetyltrimethylammonium bromide was added to a solution of magnetic nanoparticles to enhance adsorption of the analytes prior to high-performance liquid chromatography. The effects of the amount of surfactant, the amount of magnetic nanoparticles, the pH, the adsorption time, the desorption solution, and the reuse of the extractant were optimized. The linear dynamic ranges were from 0.05 to 25 milligrams per liter. The limits of detection were between 1.21 and 2.48 micrograms per liter, the limits of quantification were from 4.03 to 8.27 micrograms per liter, and the relative standard deviations were between 2.2 and 4.1 percent. This magnetic solid-phase extraction approach was successfully employed for the analysis of plastics with recoveries from 88.0 to 101.1 percent and relative standard deviations between 2.3 and 5.4 percent.

研究领域: 分析化学 · 食品科学
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THERMOCHIMICA ACTA · 2019 · IF 2.251

Latent curing epoxy systems with reduced curing temperature and improved stability

Pengbo Zhang,Sayyed Asim Ali Shah,Feng Gao,Hao Sun,Zhichao Cui,Jue Cheng,Junying Zhang

As a representative single component epoxy resin, diglycidyl ether of bisphenol A resin (DGEBA) is the most widely used matrix in adhesives. However, challenges are still remained including high curing temperature and short shelf life. Herein, bisphenol A (BPA), Tetrachlorobisphenol A (TCBPA), and Tetrabromobisphenol A (TBBPA) as latent curing agents and imidazole as accelerator were used in adhesives. Curing kinetics was studied by non-isothermal DSC, using a model-fitting Málek approach and a model-free advanced isoconversional method of Vyazovkin. Results indicated that curing temperature of EP-BPA, EP-TCBPA, and EP-TBBPA was reduced to 126 ℃, 94 ℃, and 106 ℃, respectively. Storage stability evaluated by DSC indicated the shelf life was up to five months. After curing, molecular weights of the as-prepared linear polymers (EP-BPA, EP-TCBPA, and EP-TBBPA) were 33,822 g/mol, 14,913 g/mol, and 18,846 g/mol, and their tensile strength and shear strength were more than 40.06 MPa and 13.64 MPa, respectively.

CAS / MDL: 288-32-4
研究领域: 材料科学 · 化学工程
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ARCHIVES OF TOXICOLOGY · 2017 ·Vol. 92 ·期 3 ·1215-1223 · IF 5.901

Estrogenicity of halogenated bisphenol A: in vitro and in silico investigations

Zhang Jie,Li Tiezhu,Wang Tuoyi,Yuan Cuiping,Zhong Shuning,Guan Tianzhu,Li Zhuolin,Wang Yongzhi,Yu Hansong,Luo Quan,Wang Yongjun,Zhang Tiehua

The binding interactions of bisphenol A (BPA) and its halogenated derivatives (halogenated BPAs) to human estrogen receptor α ligand binding domain (hERα-LBD) was investigated using a combined in vitro and in silico approach. First, the recombinant hERα-LBD was prepared as a soluble protein in Escherichia coli BL21(DE3)pLysS. A native fluorescent phytoestrogen, coumestrol, was employed as tracer for the fluorescence polarization assay. The results of the in vitro binding assay showed that bisphenol compounds could bind to hERα-LBD as the affinity ligands. All the tested halogenated BPAs exhibited weaker receptor binding than BPA, which might be explained by the steric effect of substituents. Molecular docking studies elucidated that the halogenated BPAs adopted different conformations in the flexible hydrophobic ligand binding pocket (LBP), which is mainly dependent on their distinct halogenation patterns. The compounds with halogen substituents on the phenolic rings and on the bridging alkyl moiety acted as agonists and antagonists for hERα, respectively. Interestingly, all the compounds in the agonist conformation of hERα formed a hydrogen bond with His524, while the compounds in the antagonist conformation formed a hydrogen bond with Thr347. These docking results suggested a pivotal role of His524/Thr347 in maintaining the hERα structure in the biologically active agonist/antagonist conformation. Comparison of the calculated binding energies vs. experimental binding affinities yielded a good correlation, which might be applicable for the structure-based design of novel bisphenol compounds with reduced toxicities and for environmental risk assessment. In addition, based on hERα-LBD as a recognition element, the proposed fluorescence polarization assay may offer an alternative to chromatographic techniques for the multi-residue determination of bisphenol compounds.

CAS / MDL: 2971-36-0
研究领域: 生物化学 · 环境科学 · 毒理学
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JOURNAL OF SEPARATION SCIENCE · 2017 ·Vol. 40 ·期 8 ·1755-1764 · IF 2.557

Aminosilanized magnetic carbon microspheres for the magnetic solid-phase extraction of bisphenol A, bisphenol AF, and tetrabromobisphenol A from environmental water samples

Sheng-Xiang Gong,Xiao-Li Wang,Wei Liu,Ming-Lin Wang,Xia Wang,Zheng-Wu Wang,Ru-Song Zhao

Aminosilanized magnetic carbon microspheres as a novel adsorbent were designed and fabricated. The adsorbent was used for the magnetic solid-phase extraction of bisphenols at trace levels from environmental water samples before liquid chromatography with tandem mass spectrometry analysis. The structure, surface, and magnetic behavior of the as-prepared aminosilanized magnetic carbon microspheres were characterized by elemental analysis, scanning electron microscopy, transmission electron microscopy, Fourier transform infrared spectroscopy, powder X-ray diffraction, and vibrating sample magnetometry. The effects of the experimental parameters were investigated by the Plackett–Burman design, and then the parameters that were significant to the extraction efficiencies were optimized through a response surface methodology. The aminosilanized magnetic carbon microspheres exhibited high adsorption efficiency and selectivity for bisphenols. Under optimal conditions, low limits of detection (0.011–2.22 ng/L), and a wide linear range (2–3 orders of magnitude), good repeatability (4.7–7.8%, n = 5), and reproducibility (6.0–8.3%, n = 3) were achieved. The results demonstrate that the novel adsorbent possesses great potentials in the determination of trace levels of bisphenols in environmental water samples.

研究领域: 分析化学 · 环境科学
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JOURNAL OF HAZARDOUS MATERIALS · 2024 · IF 12.2

Complete biodegradation of tetrabromobisphenol A through sequential anaerobic reductive dehalogenation and aerobic oxidation

Guiping Liu,Songmeng Liu,Jie Yang,Xiaoyang Zhang,Lianghua Lu,Hongxia Xu,Shujun Ye,Jichun Wu,Jiandong Jiang,Wenjing Qiao

Tetrabromobisphenol A (TBBPA), a common brominated flame retardant and a notorious pollutant in anaerobic environments, resists aerobic degradation but can undergo reductive dehalogenation to produce bisphenol A (BPA), an endocrine disruptor . Conversely, BPA is resistant to anaerobic biodegradation but susceptible to aerobic degradation. Microbial degradation of TBBPA via anoxic/oxic processes is scarcely documented. We established an anaerobic microcosm for TBBPA dehalogenation to BPA facilitated by humin. Dehalobacter species increased with a growth yield of 1.5 × 10 8 cells per μmol Br - released, suggesting their role in TBBPA dehalogenation. We innovatively achieved complete and sustainable biodegradation of TBBPA in sand/soil columns columns, synergizing TBBPA reductive dehalogenation by anaerobic functional microbiota and BPA aerobic oxidation by Sphingomonas sp. strain TTNP3. Over 42 days, 95.11 % of the injected TBBPA in three batches was debrominated to BPA. Following injection of strain TTNP3 cells, 85.57 % of BPA was aerobically degraded. Aerobic BPA degradation column experiments also indicated that aeration and cell colonization significantly increased degradation rates. This treatment strategy provides valuable technical insights for complete TBBPA biodegradation and analogous contaminants.

CAS / MDL: 80-05-7 79-94-7
研究领域: 环境科学 · 微生物学 · 生物修复
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TOXICOLOGY LETTERS · 2017 · IF 3.858

Binding interactions of halogenated bisphenol A with mouse PPARα: In vitro investigation and molecular dynamics simulation

Jie Zhang,Tiezhu Li,Tuoyi Wang,Tianzhu Guan,Hansong Yu,Zhuolin Li,Yongzhi Wang,Yongjun Wang,Tiehua Zhang

The binding of bisphenol A (BPA) and its halogenated derivatives (halogenated BPAs) to mouse peroxisome proliferator-activated receptor α ligand binding domain (mPPARα-LBD) was examined by a combination of in vitro investigation and in silico simulation. Fluorescence polarization (FP) assay showed that halogenated BPAs could bind to mPPARα-LBD* as the affinity ligands. The calculated electrostatic potential (ESP) illustrated the different charge distributions of halogenated BPAs with altered halogenation patterns. As electron-attracting substituents, halogens decrease the positive electrostatic potential and thereby have a significant influence on the electrostatic interactions of halogenated BPAs with mPPARα-LBD*. The docking results elucidated that hydrophobic and hydrogen-bonding interactions may also contribute to stabilize the binding of the halogenated BPAs to their receptor molecule. Comparison of the calculated binding energies with the experimentally determined affinities yielded a good correlation (R 2   =   0.6659) that could provide a rational basis for designing environmentally benign chemicals with reduced toxicities. This work can potentially be used for preliminary screening of halogenated BPAs.

研究领域: 环境科学 · 毒理学 · 生物化学
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JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY · 2014 ·Vol. 25 ·期 8 ·1512-1519 · IF 1.253

Vortex-assisted hollow-fiber liquid-phase microextraction coupled with high performance liquid chromatography for the determination of three synthetic endocrine disrupting compounds in milk

Li Yingtang,Yang Guorong,Zhao Jiao,Yang Yaling

In this study, a vortex-assisted three-phase hollow fiber liquid-phase microextraction (VA-HF-LPME) coupling with high performance liquid chromatography (HPLC) method was developed for determination of three synthetic endocrine disrupting compounds[EDCs, bisphenol-A (BPA), bisphenol-AF (BPAF) and tetrabromobisphenol-A (TBBPA)] in milk samples. Vortex provided effective and mild mixing of the sample solution and increased the contact between analytes and boundary layers of the hollow fibre, thereby enhancing mass transfer rate and leading to high extraction efficiency of the target analytes. The influencing parameters of VA-HF-LPME sample preparation method, such as organic solvents (acceptor phase), pH of sample solution (donor phase), sample volume, concentration of NaOH, extraction time, and ionic strength were systematically optimized. The instrumental calibration curves of BPA, BPAF and TBBPA show good linear relations (R² > 0.9988) in the concentration range of 0.5-200, 0.5-200 and 1.0-250 µg L-1, respectively. The relative standard deviations (RSD, n = 5) were 1.3-3.7%. The limits of detection (LOD, S/N = 3) were in the range of 0.16-0.35 µg L-1 and the limits of quantification (LOQ, S/N = 10) were in the range of 0.51-1.12 µg L-1. The proposed method was successfully applied to the extraction of EDCs in milk samples.

研究领域: 分析化学 · 环境科学 · 食品安全
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RSC Advances · 2015 ·Vol. 5 ·期 19 ·14631-14636 · IF 3.84

Simultaneous extraction of bisphenol A and tetrabromobisphenol A from milk by microwave-assisted ionic liquid microextraction

Haiyan Kang,Xianli Wang,Yan Zhang,Junfeng Wu,Hongqiang Wang

Considering bisphenol A (BPA) and tetrabromobisphenol-A (TBBPA) are ubiquitous environmental pollutants and widely manufactured into packaging materials, foodstuffs may be polluted by BPA and TBBPA. Additionally, there are very limited analytical methods for determining TBBPA in commercial milk samples. In this study, a rapid, simple and efficient method based on microwave-assisted ionic liquid microextraction (MAILME) combined with high-performance liquid chromatography (HPLC) was first applied to the simultaneous analysis of BPA and TBBPA in commercial milk samples. To achieve the optimum extraction performance, the experimental parameters of the MAILME, including type and amount of ionic liquid, microwave power, extraction time, pH and salt concentration in the sample, were evaluated and optimized. Under the optimum conditions, the detection limits were 0.01 and 0.02 μg L−1, and the quantification limits were 0.03 and 0.05 μg L−1 for BPA and TBBPA, respectively. The proposed method had good repeatability and reproducibility with RSDs lower than 5.6%. The recoveries of the analytes in the aged milk samples varied from 79.8 to 97.3%. The proposed method has been applied successfully to the determination of BPA and TBBPA in commercial milk samples with recoveries ranging from 78.2 to 99.8%. Compared with the other previous methods, the proposed method did not need to remove the fats and proteins in the milk, which made the sample pretreatment simple and rapid (5.0 min). And it also avoided the use of organic solvents. The proposed approach provides a new and promising alternative for simultaneously determining trace amounts of BPA and TBBPA in commercial milk samples or other similar samples.

研究领域: 分析化学 · 环境科学 · 食品科学
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MICROCHIMICA ACTA · 2020 ·Vol. 187 ·期 10 ·1-10 · IF 6.232

Bi, Fe, and Ti ternary co-doped ZrO2 nanocomposites as a mass spectrometry matrix for the determination of bisphenol A and tetrabromobisphenol A in tea

Zhen Deshuai,Shi Sisi,Gao Chan,Kang Qing,Xiao Xilin,Grimes Craig A.,Cai Qingyun

Bi, Fe, and Ti ternary co-doped ZrO 2 (BFT-ZrO 2 ) nanocomposites have been prepared by a sol-gel process and used as both adsorbent and matrix for the enrichment and determination of small molecules by surface-enhanced laser desorption/ionization time-of-flight mass spectrometry (SELDI-TOF MS). The BFT-ZrO 2 nanocomposites not only can selectively enrich a wide variety of low-mass toxic pollutants but can also be used as an excellent matrix to enhance the laser desorption/ionization efficiency with low background noise and uniform co-crystalline film. Low limits of detection (LODs) (0.1 pg mL −1 for bisphenol A (BPA), 2 pg mL −1 for tetrabromobisphenol A (TBBPA), 0.1 pg mL −1 for alizarin (AZ), 0.001 pg mL −1 for bisphenol S (BPS), 0.01 pg mL −1 for indigo blue (ID), 0.01 pg mL −1 for pentachlorophenol (PCP), 100 pg mL −1 for estradiol (E2), 0.001 pg mL −1 for cetyltrimethylammonium bromide (CTAB), 0.1 pg mL −1 for crystal violet (CV), 1 pg mL −1 for malachite green (MG), 0.01 pg mL −1 for rhodamine B (RhB), and 0.01 pg mL −1 for perfluorooctane sulfonate (PFOS) were achieved. The relative standard deviations (RSDs) of shot-to-shot are 9.4–24% and of sample-to-sample 5.2–17%. The BFT-ZrO 2 matrix was successfully applied to the determination of TBBPA and BPA in tea samples. This method shows a new strategy for determination of toxic compounds in tea. Graphical abstract

研究领域: 分析化学 · 环境科学
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