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SEPARATION AND PURIFICATION TECHNOLOGY · 2021 · IF 7.312

Photochemical degradation and debromination of bromophenols: Overlooked role of hydrated electron

Libin Fu,Xueqin Peng,Qi Chen,Yaobin Ding,Jizhou Jiang

Photolysis and debromination of bromophenols were widely investigated previously. However, the role of reactive species especially hydrated electrons (e aq − ) in their degradation was overlooked. Therefore, in the study, generation and role of the reactive species generated during the photolysis of bromophenols were identified and evaluated by using 2,4,6-tribromophenol (TBP) as a model at different pH values from 4 to 11 under anaerobic condition. It was found that photolysis of TBP solution under UV irradiation (254 nm) yielded organic radicals (C•), hydrogen radicals (H•) and e aq − . By using nitrite and monochloroacetic acid (MCAA) as scavengers of H•/e aq − , the role of UV direct photolysis, H• and e aq − in degradation of TBP was quantitatively assessed at different initial pH (pH 0 ) values. UV irradiation induced direct photolysis of TBP was mainly dependent on its molar absorbance coefficient (ε) at 254 nm. Contribution rate of UV irradiation to degradation of TBP was about 60% at pH 0 4, 7 and 11. Interestingly, the contribution rate of e aq − was high as 35.8%-40% at pH 0 4–11, while the contribution rate of H• was negligible (<2.5%) at these pH values. Accordingly, UV and e aq − induced degradation and debromination pathways of TBP under UV irradiation were proposed. This work gains deep insight into the photolysis process of bromophenols, and clarifies the important role of e aq − in photo-degradation of bromophenols.

研究领域: 环境科学 · 化学
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ENVIRONMENTAL POLLUTION · 2019 · IF 5.714

A combined experimental and computational study on the oxidative degradation of bromophenols by Fe(VI) and the formation of self-coupling products

Afzal Ahmed Dar,Jing Chen,Asam Shad,Xiaoxue Pan,Jiayi Yao,May Bin-Jumah,Ahmed A. Allam,Zongli Huo,Feng Zhu,Zunyao Wang

In this study, the degradation of eight bromophenols (BPs), including monobromophenols (2-BP, 3-BP, and 4-BP), dibromophenols (2,4-DBP, 2,6-DBP, and 3,5-DBP), a tribromophenol (2,4,6-TBP) and a pentabromophenol (PBP), by a Fe(VI) reaction process at a pH of 8.0 was systematically studied. It was concluded that their degradation rates increased with increasing Fe(VI) concentrations in solution. The removal of 2,4,6-TBP, 2-BP, and 2,6-DBP was faster than that of the other five BPs, which could be attributed to the position of the substituting Br atom. Moreover, the direct oxidation and coupling reactions greatly influenced the reactivity of the bromophenols with Fe(VI). The electron paramagnetic resonance (EPR) analysis confirmed the presence of hydroxyl radicals in present system. The oxidation reaction products of PBP and 2-BP were recognized by an electrospray time-of-flight mass spectrometer ; hydroxylation, hydroxyl substitution, the cleavage of the C–C bond, direct oxidation and polymerization via an end linking mechanism were noticeably found in the reaction process, resulting in the formation of polymerization products and causing hydroxylation to occur. Theoretical calculations further determined the possible oxidation sites of 2-BP and PBP. This study may provide comprehensive and important information on the remediation of BPs by Fe(VI).

研究领域: 环境科学 · 化学
✓ 已验证 DOI PubMed 高影响因子
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SEPARATION AND PURIFICATION TECHNOLOGY · 2021 · IF 7.312

Mechanism insights into activation of hydroxylamines for generation of multiple reactive species in photochemical degradation of bromophenols

Libin Fu,Fenna Lide,Yaobin Ding,Chengjun Wang,Jizhou Jiang,Jia Huang

Photolysis of bromophenols and nitrogen cycle are two common processes in the natural water bodies. In the study, effect of hydroxylamine (HA), an intermediate of nitrogen cycle, on UV photolysis of bromophenols in the aqueous solution was investigated under different conditions. It was found that HA presence not only changed formation of reactive species, also varied degradation pathways of 2,4,6-tribromophenol (TBP). During photolysis of TBP, carbon-centered radicals (C ), H and e aq − were produced, while new radicals of OH, NO 2 and NH 2 were produced after addition of HA. Moreover, the added HA greatly inhibited hydrolysis of C via the reaction between them, thereby depressing formation of hydroxylated intermediates (e.g., monohydroxylated 2,6-dibromophenol), and improving debromination of TBP in UV/HA/TBP system. It is worth noting that two new nitro/amino byproducts of concern were detected in UV/HA/TBP system. They are proposed to be generated from the combination of C with NO 2 and NH 2 . Furthermore, nitro/amino byproducts were one of the major sink pathways of HA in UV/HA/TBP system. This is the first article to demonstrate the formation of nitro/amino byproducts form photodegradation of phenolic compounds in the presence of HA, and to clarify reaction mechanism for generation of OH, NO 2 and NH 2 from HA activation during photolysis of bromophenols in the aqueous solution.

CAS / MDL: 3317-61-1
研究领域: 环境科学 · 化学
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Environments · 2017 ·Vol. 4 ·期 2 ·30 · IF 0

A Facile Approach to Preparing Molecularly Imprinted Chitosan for Detecting 2,4,6-Tribromophenol with a Widely Linear Range

Limei Huang,Yaqi Lu,Zhenyue Wu,Meishan Li,Shengchang Xiang,Xiuling Ma,Zhangjing Zhang

The environmental pollution of 2,4,6-tribromophenol (TBP) has attracted attention. Based on an urgent need for the better provision of clean water, in situ determination of TBP is of great importance. Here, a facile and effective approach for detecting TBP is developed, based on coupling molecular imprinting technique with electrodeposition of chitosan (CS) on the gold electrode. The TBP imprinting CS film was fabricated by using CS as functional material and TBP as template molecule. The experiments show that the morphologies and electrochemical properties of the imprinted film sensor was different from non-imprinted film electrode. The current of the imprinted film was linearly proportional to the TBP concentration, with a wide linear range of 1.0 × 10−7mol·L−1to 1.0 × 10−3mol·L−1. By selecting drop-coating method as a reference for controlled trials with the same functional material, the results illustrated that the electrodeposition enjoyed a widely linear range advantage.Keywords:2,4,6-tribromophenol;chitosan;molecular imprinting;electrodeposition

CAS / MDL: 126-73-8
研究领域: 环境科学 · 分析化学
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TALANTA · 2015 · IF 3.545

Sensitivity enhancement of pH indicator and its application in the evaluation of fish freshness

Wen Sun,Hui Li,Han Wang,Shan Xiao,Jihui Wang,Liang Feng

The sensitivity of pH indicators is always confined in acidic solvents used during the immobilization because of the large deviation from their color transition points. By regulating the pH of indicators using organic acid or base, the color transition points of indicators could be readily achieved and the sensitivity could be greatly enhanced. In this study, bromophenol blue was selected as an example to interpret this improvement. And Hue, Saturation and Value (HSV) color model was applied to obtain digital color information of pH indicators. In addition, other two kinds of pH indicators were chosen and regulated to their color transition points as well. The resultant indicators together with the original ones were composed to a colorimetric sensor array and utilized to determine fish freshness. Compared with the original indicators, much higher sensitivity in the detection of fish freshness was obtained by the pH regulated indicators.

研究领域: 食品科学 · 分析化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Nanomaterials · 2022 ·Vol. 12 ·期 20 ·3636 · IF 5.719

Organo-Vermiculites Modified by Aza-Containing Gemini Surfactants: Efficient Uptake of 2-Naphthol and Bromophenol Blue

Jianchao Gong,Tingting Wang,Wei Zhang,Lin Han,Mingxiao Gao,Tianen Chen,Tao Shen,Yaxiong Ji

To explore the effect of spacer structure on the adsorption capability of organo-vermiculites (organo-Vts), a series of aza-containing gemini surfactants (5N, 7N and 8N) are applied to modify Na-vermiculite (Na-Vt). Large interlayer spacing, strong binding strength and high modifier availability are observed in organo-Vts, which endow them with superiority for the adsorption of 2-naphthol (2-NP) and bromophenol blue (BPB). The maximum adsorption capacities of 5N-Vt, 7N-Vt and 8N-Vt toward 2-NP/BPB are 142.08/364.49, 156.61/372.65 and 146.50/287.90 mg/g, respectively, with the adsorption processes well fit by the PSO model and Freundlich isotherm. The quicker adsorption equilibrium of 2-NP than BPB is due to the easier diffusion of smaller 2-NP molecules into the interlayer space of organo-Vts. Moreover, stable regeneration of 7N-Vt is verified, with feasibility in the binary-component system that is demonstrated. A combination of theoretical simulation and characterization is conducted to reveal the adsorption mechanism; the adsorption processes are mainly through partition processes, electrostatic interaction and functional interactions, in which the spacer structure affects the interlayer environment and adsorptive site distribution, whereas the adsorbate structure plays a role in the diffusion process and secondary intermolecular interactions. The results of this study demonstrate the versatile applicability of aza-based organo-Vts targeted at the removal of phenols and dyes as well as provide theoretical guidance for the structural optimization and mechanistic exploration of organo-Vt adsorbents.Keywords:organo-vermiculite;aza-containing gemini surfactant;2-Naphthol;bromophenol blue;adsorption

研究领域: 环境科学 · 材料科学
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CHEMOSPHERE · 2020 · IF 5.778

Transformation of bromophenols by aqueous chlorination and exploration of main reaction mechanisms

Wenrui Xiang,Jingyi Chang,Ruijuan Qu,Gadah Albasher,Zunyao Wang,Dongmei Zhou,Cheng Sun

Bromophenols (BPs) are ubiquitous phenolic contaminants and typical halogenated disinfection byproducts (DBPs) that are commonly detected in aquatic environments. The transformation of 2,4-dibromophenol (2,4-DBP) during chlorination process was fully explored in this research. It was found that active chlorine can react with 2,4-DBP effectively in a wide pH range of 5.0–11.0, with an apparent second-order rate constant ( k app ) varying from 0.8 M −1  s −1 to 110.3 M −1  s −1 . The addition of 5 mM ammonium ions almost completely suppressed the reaction via competitive consumption of free chlorine. With the concentration of HA increasing from 1.0 to 10.0 mg L −1 , the inhibition on the degradation of 2,4-DBP increased from 8.7% to 63.4%. By contrast, bromide ions at a concentration of 5 mM accelerated the process by about 4 times, due to the formation of hypobromous acid. On the basis of the eleven products (with eight nominal masses) identified by LC-TOF-MS, electrophilic substitution reactions and single-electron transfer reactions were mainly involved in the chlorination process. The concentration of primary chlorine-substituted products was about 4 times that of the dimer products, demonstrating that electrophilic substitution reaction was predominant during chlorination of 2,4-DBP. Density functional theory (DFT) based calculations revealed that HOCl is the dominant active oxidizing species for elimination of 2,4-DBP and coupling reaction occurs more easily at para and ortho position of hydroxyl group in the phenolic moiety. These findings could provide some new insights into the environmental fate of bromophenols during chlorine disinfection of water and wastewaters.

研究领域: 环境科学 · 化学
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Sustainable Materials and Technologies · 2024 · IF 8.6

Fabrication of a 2D/2D g-C3N4@ZnTDA nanosheets catalyst for highly efficient degradation of 2,4-dibromophenol and improved flame retardancy of polyurethane foam

Zhoumei Xu,Fukai Chu,Chuanshen Wang,Xin Wang,Yanbei Hou,Weizhao Hu,Lei Song

High charge separation and transfer efficiency are considered as key factors of photocatalysts in wastewater treatment applications. In this work, a high performance photocatalyst g-C 3 N 4 @ZnTDA was designed and applied through a facile solvothermal strategy. The microstructural, morphological, physicochemical, and photoelectrochemical properties of g-C 3 N 4 @ZnTDA were fully characterized. The photocatalytic activity of g-C 3 N 4 @ZnTDA nanoparticles under visible light source in degrading the 2,4-dibromophenol(2,4-dB) contaminants was also successfully studied. Additionally, the g-C 3 N 4 @ZnTDA composite demonstrates easy operation and good regeneration ability, making it highly promising for the efficient removal of phenolic pollutants from wastewater. Besides, a novel reutilization method for used catalyst as flame retardant and for PU foams was successfully testified. The MCN-3 as a fire-safety coating could reduce the heat release and improve flame retardancy of PU composites. This work opens a new window for valuable inspiration and structural design of reutilized MOF composites.

研究领域: 材料科学 · 环境科学 · 化学工程
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MONATSHEFTE FUR CHEMIE · 2014 ·Vol. 146 ·期 3 ·485-491 · IF 1.347

Sensing 2,4,6-tribromophenol based on molecularly imprinted technology

Ma Xiuling,Wu Dan,Huang Limei,Wu Zhenyue,Xiang Shengchang,Chen Sheng

Abstract 2,4,6-Tribromophenol has been used as flame retardant and is a synthetic intermediate of the most important brominated flame retardants produced. In this work, a novel electrochemical sensor for determining 2,4,6-tribromophenol was fabricated by surface molecular imprinting technology, in which core–shell nanoparticles modified with (3-chloropropyl)trimethoxysilan and polyethylenimine were used as functional monomer, and 2,4,6-tribromophenol as template, ethylene glycol dimethacrylate as cross-linker. The electrochemical behavior the modified electrodes was investigated by electrochemical impedance spectroscopy and differential pulse voltammetry. The results showed that the imprinted electrode was significantly different from the non-imprinted electrode. The imprinted electrode had ascendant selective recognition ability, exhibited a low detection limit (1.51 × 10 −8 mol/dm 3 ) and good repeatability (RSD is 4.35 % for 5 times) for the detection of 2,4,6-tribromophenol. Graphical abstract

研究领域: 环境科学 · 分析化学
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INDUSTRIAL CROPS AND PRODUCTS · 2024 · IF 5.6

Highly efficient adsorption of anionic dyes on a porous graphene oxide nanosheets/chitosan composite aerogel

Yanke Li,Huilin Liu,Runda Nie,Yue Li,Qinglin Li,Yunfeng Lei,Mingming Guo,Yichuan Zhang

Graphene oxide nanosheets (GONs) treatment of anionic dyeing wastewater has been characterized by low removal efficiency due to its electronegativity. However, further modification and enhancement of graphene oxide make it difficult to balance cost and efficiency. Herein, we report an economical, practical, and environmentally friendly composite aerogel of GONs and chitosan (CS) in anionic dye adsorption. The abundant oxygen-containing functional groups on the surface of GONs may form hydrogen bonds with dye molecules. Meanwhile, the amino-positive active sites on the chain segments of CS molecules may anchor anionic dyes. The adsorption capacities of composite aerogel for methyl orange (MO) and bromophenol blue (BPB) anionic dyes by electrostatic attraction, hydrogen bonds, and π-π conjugate interactions are 3.7 and 1.8 times than that of pure CS aerogel from the adsorption results, respectively. Moreover, the maximum adsorption capacities of composite aerogel for MO and BPB are 179.21 and 236.42 mg g −1 at room temperature and in a neutral environment. Therefore, this simple and cost-effective graphene aerogel anionic dye adsorbent may be used for the protection of the water environment.

研究领域: 环境科学 · 材料科学
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2025 · IF 8.5

Cross-linked graphene with chitosan nanocomposites for efficient photocatalytic degradation of bromothymol blue, bromophenol blue dye molecules

Muthuchamy Maruthupandy,Govindan Rajivgandhi,Thillaichidambaram Muneeswaran,Seerangaraj Vasantharaj,Gabriela Sandoval-Hevia,Muniyandi Muneeswaran,Nurul Asyikin Binti Mohamed Radzi

The pervasive occurrence of various organic contaminants, primarily dye molecules, in water bodies was caused by multiple dye industrial wastes, which recently sparked great scientific concern and public awareness due to their potential to spread these contaminants' resistant genes and pose a risk to humans. Cross-linking graphene in chitosan resulted in nanocomposites with varied morphology, increased surface area, and improved photocatalytic removal of bromothymol blue and bromophenol blue. The degradation capacity of photocatalysts at various concentrations (25 and 50 mg) was 96.2 % (170 min) and 99.2 % (80 min) with bromothymol blue, revealing a two-fold variation based on the Gr/Cts NCs concentrations. Similar to bromophenol blue dye molecules, which showed a two-fold enhancement of degradation based on graphene/chitosan nanocomposites concentration, bromophenol blue dye molecules were 95.3 % and 98.6 % at 240 and 120 min time intervals. The bromophenol blue and bromothymol blue dyes degraded according to the Langmuir adsorption model. Furthermore, the minimal cytotoxicity of graphene/chitosan nanocomposites to the human lung epithelial cell line and the human macrophage-like cell line indicates that the material is safe. This study reveals that the degrading properties of graphene/chitosan nanocomposites significantly improve as the concentration increases.

CAS / MDL: 9012-76-4
研究领域: 环境科学 · 材料科学 · 生物学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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CHEMOSPHERE · 2024 · IF 8.1

Exploring the biosynthetic possibilities of hydroxylated polybrominated diphenyl ethers from bromophenols in Prorocentrum donghaiense: Implications for bioremediation

Bin Li,Jianghong Shi,Xueling Xiang,Mengtao Zhang,Hui Ge,Shuhan Sun

Bromophenols has been proven to synthesize hydroxylated polybrominated diphenyl ethers (OH-PBDEs), which may pose additional environmental and health risks in the process of bioremediation. In this study, the removal of 2,4-dibromophenol (2,4-DBP) and 2,4,6-tribromophenol (2,4,6-TBP) and the biosynthetic of OH-PBDEs by Prorocentrum donghaiense were explored. The removal efficiencies of 2,4-DBP and 2,4,6-TBP ranged from 32.71% to 76.89% and 31.15%–78.12%, respectively. Low concentrations of 2,4-DBP stimulated algal growth , while high concentrations were inhibitory. Furthermore, exposure to 10.00 mg L −1 2,4-DBP resulted in the detection of 2′-hydroxy-2,3′,4,5′-tetrabromodiphenyl ether (2′–OH–BDE-68) within P . donghaiense . In contrast, increasing concentrations of 2,4,6-TBP considerably inhibited P . donghaiense growth, with 4′-hydroxy-2,3′,4,5′,6-pentabromodiphenyl ether (4′–OH–BDE-121) detected within P. donghaiense under 5.00 mg L −1 2,4,6-TBP. Metabolomic analysis further revealed that the synthesized OH-PBDEs exhibited higher toxicity than their precursors and identified the oxidative coupling as a key biosynthetic mechanism. These findings confirm the capacity of P. donghaiense to remove bromophenols and biosynthesize OH-PBDEs from bromophenols, offering valuable insights into formulating algal bioremediation to mitigate bromophenol contamination.

研究领域: 环境科学 · 海洋生物学 · 毒理学
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