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Diphenyl ether
BIOLOGY AND FERTILITY OF SOILS · 2018 ·Vol. 54 ·期 7 ·807-817 · IF 3.808

Manure amendment reduced plant uptake and enhanced rhizodegradation of 2,2′,4, 4′-tetrabrominated diphenyl ether in soil

Xiang Leilei,Song Yang,Bian Yongrong,Liu Guangxia,Herzberger Anna,Gu Chenggang,Jiang Xin,Wang Fang

To test whether manure amendment in soil reduces plant uptake of persistent organic pollutants, carrot ( Daucus carota L. ) was used as a model plant and 2,2′,4,4′-tetrabrominated diphenyl ether (BDE-47) was selected as a model persistent organic pollutant to conduct a pot experiment with contaminated soil amended by composted pig manure. The results showed that the concentration and bioconcentration factors (BCFs) of BDE-47 in the edible part of carrot significantly decreased from 229.7 ± 28.2 to 43.4 ± 20.4 ng g −1 and from 1.86 ± 0.5 to 0.15 ± 0.03, respectively, with increasing composted pig manure dose from 0 to 4%. Organic matter (OM) derived from composted pig manure played a dominant role in reducing persistent organic pollutant bioavailability in soil. Composted pig manure amendment and carrot cultivation jointly altered the bacterial community composition in soil, especially the rhizosphere. Rhizodegradation of BDE-47 was enhanced from 8.6 to 28.5% with increasing composted pig manure dose from 0 to 4%, corresponding to increased soil microbe diversity and polybrominated diphenyl ether-degrading bacteria ( Sphingomonas , etc.) abundance in the rhizosphere. This study is the first, to the best of our knowledge, to provide an effective agronomic strategy of manure amendment to reduce plant uptake and simultaneously enhance rhizodegradation of persistent organic pollutants in soil, and thus potentially reduce human health risks through dietary intake.

CAS / MDL: 68855-54-9 91053-39-3
研究领域: 环境科学 · 土壤学 · 植物学
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Journal of Environmental Chemical Engineering · 2023 · IF 7.7

Enhanced degradation of monobrominated diphenyl ether by sophorolipid modified nanoscale zerovalent iron: Reactivity, electron selectivity, and mechanism

Long Zhou,Bin Zheng,Kai Zhang,Chengjie Xue,Zhanqiang Fang

Nanoscale zero-valent iron (nZVI) is regard as a promising reductant for halogenated organic compounds remediation, while it still suffers from low reactivity and poor electron selectivity toward monobrominated diphenyl ether. In this paper, the modified nZVI was successfully prepared via introducing sophorolipid during the synthesis of nZVI by a one-step method (SL-nZVI). The experimental results demonstrated that the degradation efficiency of SL-nZVI for BDE-3 could reach up to 99.96%, which was significantly higher than that of nZVI (59.60%). TEM and BET characterizations indicated that the modified nZVI possessed excellent dispersion properties and higher specific surface area, while the electrochemical tests results revealed that the sophorolipid modification reduced the charge transfer resistance of nZVI and favored the electron transfer . Besides, the introduced sophorolipid enhanced solubilization of hydrophobic organic contaminants via halogen bonding interaction also contributes to the increasement of BDE-3 degradation. More importantly, the experimental results also indicated that the utilization efficiency and electron selectivity of nZVI particles for the BDE-3 were significantly improved after sophorolipid modification (from 56.64% and 2.69% to 74.14% and 7.39%, respectively), and this could be owned to more accessible active sites, as well as the increased hydrophobicity of nZVI, which is not conducive to the adsorption of hydrophobic BDE-3 onto the nZVI surface, but reduces the occurrence of side reaction between nZVI and water. Those results demonstrate that the sophorolipid modification is an efficient strategy for nZVI in the remediation of hydrophobic BDE-3, and also highlight the promising prospects of sophorolipid in increasing the reactivity and electron selectivity of nZVI.

研究领域: 环境科学 · 化学工程
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ENVIRONMENTAL POLLUTION · 2020 · IF 6.793

Photoassisted degradation of 2,2′,4,4′-tetrabrominated diphenyl ether in simulated soil washing system containing Triton X series surfactants

Kaibo Huang,He Liu,Jinglei He,Yan Li,Rui Wang,Ting Tang,Xueqin Tao,Hua Yin,Zhi Dang,Guining Lu

This study aims to use ultraviolet (UV) irradiation to decompose polybrominated diphenyl ethers (PBDEs) in the elutes and then reuse the surfactants. The results indicate that UV can remove 2,2′,4,4′-tetrabrominated diphenyl ether (BDE-47) from surfactant eluents and Triton X series surfactants also can remove BDE-47 from the soil. Triton X-100 (TX-100) is the most promising surfactant during the washing and photodegradation processes. Quench experiments suggest that both 1 O 2 and OH• were involved in the TX-100 decomposition but only 1 O 2 is responsible for the degradation of BDE-47. In analysis of the photoproducts of BDE-47 by Gas Chromatography Mass Spectrum (GC-MS) and Liquid Chromatography High Resolution Mass Spectrometry (LC-HRMS), BDE-47 was mainly debrominated to the lower-brominated BDEs and then oxidized to ring-opening products. The little loss of TX-100 can mainly be attributed to the breakage of polyethylene oxide (PEO) chain. Nevertheless, the washing wastes treated by UV light can exhibit higher solubility for BDE-47 than before, indicating they can be reused for BDE-47 removal from soil. The toxicity assessment experiments were performed using Escherichia coli ( E.coli ) as an indicator. The results indicate that the removal of BDE-47 by UV irradiation can reduce the toxicity of eluent.

研究领域: 环境科学 · 污染治理 · 化学工程
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2025 · IF 6.2

Pdr15 ABC Transporter of Phyllospheric Yeast Enhances Plant Tolerance to 4-Monobrominated Diphenyl Ether, Chromium, and Cadmium Stress

Man Cai,Zheng Xing,Chen Du,Xinyu Ding,Mengyu Zhang,Chengjin Zhou

The ecological risks brought by heavy metals and 4-monobromodiphenyl ether (BDE-3) copollutants are among the most common environmental contaminants. Heavy metals and other substrates are actively transported across cellular membranes by an ATP-binding cassette (ABC) transporter. Previous studies have suggested that phyllospheric yeast (Wickerhamomyces anomalus) can survive in BDE-3 and heavy metal environments. However, the underlying molecular mechanisms of BDE-3 and heavy metal tolerance are not clear. To assess the impact of the yeast transporter pdr15 gene on plant tolerance, tissue heavy metal levels, and BDE-3 levels, we heterologously expressed the gene in tobacco. Accumulating evidence has suggested that transgenic tobacco contributes to the reduction of plant damage by resulting in heavy metals and BDE-3 in specific subcellular organelles. Dimethyl ether and phthalic acid metabolism were the two main metabolic pathways for the toxicity-reducing effect. Our findings broaden the understanding of ABC transporter function and their regulatory metabolic pathways in heavy metal and BDE-3 co-contaminated resistance.

CAS / MDL: 7440-43-9
研究领域: 环境毒理学 · 植物生物技术 · 分子生物学 · 微生物遗传学 · 植物修复 · 胁迫生理学
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MOLECULAR PLANT-MICROBE INTERACTIONS · 2024 · IF 3.2

Maize root exudates promote Bacillus sp. Za detoxification of diphenyl ether herbicides by enhancing colonization and biofilm formation

Yanning Tian,Fangya Zhong,Na Shang,Houyu Yu,Dongmei Mao,Xing Huang

Diphenyl ether herbicides are extensively utilized in agricultural systems, but their residues threaten the health of sensitive rotation crops. Functional microbial strains can degrade diphenyl ether herbicides in the rhizosphere of crops, facilitating the restoration of a healthy agricultural environment. However, the interplay between microorganisms and plants in diphenyl ether herbicides degradation remains unclear. Thus, the herbicide-degrading strain Bacillus sp. Za and the sensitive crop, maize, were employed to uncover the interaction mechanism. The degradation of diphenyl ether herbicides by strain Bacillus sp. Za was promoted by root exudates. The strain induced root exudates re-secretion in diphenyl ether herbicide-polluted maize. We further showed that root exudates enhanced the rhizosphere colonization and the biofilm biomass of strain Za, augmenting its capacity to degrade diphenyl ether herbicide. Root exudates regulated gene fliZ, pivotal in biofilm formation. Wild-type strain Za significantly reduced herbicide toxicity to maize compared to the ZaΔfliZ mutant. Moreover, root exudates promoted strain Za growth and chemotaxis, which was related to biofilm formation. This mutualistic relationship between the microorganisms and the plants demonstrates the significance of plant-microbe interactions in shaping diphenyl ether herbicide degradation in rhizosphere soils.

研究领域: 环境微生物学 · 植物科学 · 农业化学 · 微生物生态学 · 生物修复
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POLYMER SCIENCE SERIES B · 2019 ·Vol. 61 ·期 2 ·124-131 · IF 0.907

Effect of Diphenyl Ether in Ti-based Ternary Catalyst on Polymerization, Microstructure and Property of cis-1,4-Polyisoprene

Guanghong Lin,Xiang Hongping,Xi Lu,Wen Zhixia,Wang Zhaowei,Yu Junwei,Liu Xiaoxuan

Abstract A tricomponent catalyst comprising titanium tetrachloride, triisobutyl aluminum and diphenyl ether is developed for the highly cis -1,4-selective polymerization of isoprene. The influence of the content of diphenyl ether and its complexation order on polymerization, microstructure and performance of polyisoprene are studied. The polyisoprene synthesized presents high monomer conversion (91–99%). With the increasing of diphenyl ether content, intrinsic viscosity and viscosity-average molecular weight of polyisoprene increase. The molar percentage of cis -1,4-unit is almost unaffected by diphenyl ether and different complexation sequence. The polyisoprene reveals comparable T g (–61.31°C) and mechanical strengths (11.14 MPa, 667%) to commercially available LHIR-80 synthesized with neodymium. However, the viscosity and viscosity-average molecular weight of the former are lower than that of the latter, which avails the processability and maintains excellent mechanical properties.

研究领域: 高分子化学 · 材料科学
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CHEMICAL ENGINEERING JOURNAL · 2023 · IF 15.1

Synergy of electronic and steric effects of Br-Ni catalysts for selective hydrogenolysis of diphenyl ether to phenol

Xiaomeng Yang,Zhen Zhang,Puhua Shao,Armin Rezayan,Dan Wu,Chunbao Charles Xu,Jianshe Wang,Yongsheng Zhang

Selective hydrogenolysis of 4-O-5 bond in lignin under relatively mild conditions is an important strategy for the production of valuable aromatic products, e.g. phenols, from renewable carbon resources. However, the easy saturation of benzene rings under reductive conditions over metal catalyst reduces the selectivity to aromatics. In this work, we investigated the effect of bromination of supported Ni nanoparticles on the phenol selectivity during the hydrogenolysis of diphenyl ether (DPE), a commonly used lignin model compound. Compared with the unmodified catalysts, Br-Ni/Al 2 O 3 catalyst derived from Ni-Al layered double oxides exhibits enhanced phenol selectivity (37% vs. 15%) under similar DPE conversions (60%). Various characterizations including transmission electron microscopy (TEM), in-situ X-ray photoelectron spectroscopy (XPS), extended X-ray absorption fine structure (EXAFS), and CO-Fourier transform infrared spectroscopy (FTIR) indicate that Br preferentially located at the terrace site of Ni nanoparticles, deactivating the continuous Ni sites for benzene ring hydrogenation. In addition, the electron-withdrawing effect of Br creates positively charged Ni sites at the corners, facilitating the hydrogenolysis of C–O aryl ether bonds. During the hydrogenation of real lignin, the selective poisoning and electronic effects introduced by Br synergistically increased the yield of phenols from 12.20% on the initial Ni/Al 2 O 3 to 30.47% over the Br-Ni/Al 2 O 3 catalyst. This work provides an advanced strategy for the catalytic valorization of lignin by halogen modified metal-based catalysts.

研究领域: 催化 · 化学工程 · 可再生能源 · 材料科学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2023 · IF 4.4

Integration of solid-phase microextraction and surface-enhanced Raman spectroscopy for in-vivo screening of polybrominated diphenyl ether

Mengping Zhang,Xiao Meng,Nianlu Li,Wei Zou,Haiyan Wei,Ranran Liu,Yaxin Sun,Wenwen Chen,Jingcheng Cui,Cuijuan Wang

The monitoring of polybrominated diphenyl ethers (PBDEs) is of great significance owing to their high persistence, bioaccumulation, and toxicity to humans and animals. In this study, a sensitive and reproducible probe that integrates solid-phase microextraction and surface-enhanced Raman spectroscopy (SPME-SERS) was developed for screening PBDEs in multiphase specimens, including live fish, water, and electrical products. A roughed Cu fiber with an Ag layer was fabricated with dual functions. BDE-15 was readily extracted and detected on the SPME-SERS probe consisting of propanethiol-modified Ag nanoplates on a Cu wire. A clear linear relationship (R 2  = 0.988) was established between the SERS intensity at 782 cm −1 and the logarithmic concentrations (from 100 ppb to 100 ppm), with a detection limit of 15 ppb. This proposed method enables continuous in vivo monitoring in fish without complicated pretreatments. The results obtained by this SPME-SERS approach were validated by high-performance liquid chromatography and showed good agreement. This “extracting and detecting” SPME-SERS method provides a potential tool to monitor the occurrence, formation, and migration of PBDEs.

CAS / MDL: 552-16-9 107-03-9
研究领域: 环境科学 · 分析化学
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WATER AIR AND SOIL POLLUTION · 2018 ·Vol. 229 ·期 3 ·1-10 · IF 1.769

Effects of Synthesis Conditions on Characteristics of Ni/Fe Nanoparticles and Their Application for Degradation of Decabrominated Diphenyl Ether

Yi Yunqiang,Wu Juan,Wei Yufen,Fang Zhanqiang,Gong Yanyan,Zhao Dongye

Ni/Fe bimetallic nanoparticles have been widely used as strong reductants to degrade organic pollutants. Synthesis parameters of Ni/Fe nanoparticles can directly affect their characteristics and reactivity. In this study, Ni/Fe nanoparticles were prepared at different synthesis conditions, namely, synthesizing temperature, stirring rate, washing solutions, and preparation methods (post-coated and co-reducted Ni/Fe nanoparticles), and investigated their effectiveness of decabrominated diphenyl ether (BDE209) degradation. The results showed that the successive order of factors affecting the kinetics constant of Ni/Fe nanoparticles for the removal of decabrominated diphenyl ether (BDE209) were preparation methods, washing solutions, stirring rate, and synthesis temperature. It should be noted that the kinetics constants of post-coated Ni/Fe nanoparticles for removal of BDE209 was 0.049 min −1 , which was 14 times higher than that of co-reducted Ni/Fe nanoparticles. Moreover, the most remarkable influence on the particle size of Ni/Fe nanoparticles was the stirring rate, others synthesis conditions are mentioned in the following order: washing solutions > preparation methods > synthesis temperature. Interestingly, the effects of synthesis condition on the crystalline structure of Ni/Fe were weak. The results may facilitate more effective application of Ni/Fe nanoparticles for degradation of BDE209.

研究领域: 环境科学 · 材料科学
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Materials Research Express · 2017 ·Vol. 4 ·期 8 ·085009 · IF 1.068

Enhanced debromination of decabrominated diphenyl ether in aqueous solution by attapulgite supported Fe/Ni bimetallic nanoparticles: kinetics and pathways

Zongtang Liu,Chenggang Gu,Yongrong Bian,Xin Jiang,Yufeng Sun,Zhenghao Fei,Jingtao Dai

In this study, Fe/Ni bimetallic nanoparticles were supported on the attapulgite (A-Fe/Ni) to enhance the degradation reactivity of decabrominated diphenyl ether (BDE209) in aqueous solution. The Fe/Ni nanoparticles were well distributed on the attapulgite surface with an average diameter of 20–40 nm. The removal percentage of BDE209 by A-Fe/Ni was 1.59 times higher than Fe/Ni nanoparticles alone because attapulgite could act as supporting material to disperse Fe/Ni nanoparticles and prevent Fe/Ni nanoparticles from aggregation. The degradation kinetics for BDE209 debromination by A-Fe/Ni could be well described by a pseudo-first-order model, and the debromination rate constant of BDE209 increased with increasing the dosage of A-Fe/Ni, water/THF ratio, and decreasing the initial BDE209 concentration and solution pH. The degradation products were identified using a third-order polynomial regression equation between the experimental and reference gas chromatography relative retention times. Stepwise debromination from n-bromo-DE to (n  −  1)-bromo-DE was a possible pathway with bromines being substituted sequentially by hydrogen. The preferred elimination of bromines of BDE209 by A-Fe/Ni followed the debromination preference of para-Br  >  meta-Br  >  ortho-Br. The results provide evidences for understanding the debromination mechanism of polybrominated diphenyl ether by clay-supported Fe/Ni nanoparticles.

研究领域: 环境科学 · 化学工程
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MOLECULES · 2023 ·Vol. 28 ·期 4 ·1911 · IF 4.6

Synthesis, Antifungal Activity, 3D-QSAR and Controlled Release on Hydrotalcite Study of Longifolene-Derived Diphenyl Ether Carboxylic Acid Compounds

Xiaocui Wu,Guishan Lin,Wengui Duan,Baoyu Li,Yucheng Cui,Bo Cen,Fuhou Lei

Twenty-two novel longifolene-derived diphenyl ether-carboxylic acid compounds7a–7vwere synthesized from renewable biomass resources longifolene, and their structures were confirmed by FT-IR,1H NMR,13C NMR, and HRMS. The preliminary evaluation of in vitro antifungal activity displayed that compound7bpresented inhibition rates of 85.9%, 82.7%, 82.7%, and 81.4% againstAlternaria solani, Cercospora arachidicola,Rhizoctonia solani,andPhysalospora piricola, respectively, and compound7lpossessed inhibition rates of 80.7%, 80.4%, and 80.3% againstR. solani,C. arachidicola,P. piricola, respectively, exhibiting excellent and broad-spectrum antifungal activities. Besides, compounds7fand7ashowed significant antifungal activities with inhibition rates of 81.2% and 80.7% againstA.solani, respectively. Meanwhile, a reasonable and effective 3D-QSAR mode (r2= 0.996,q2= 0.572) has been established by the CoMFA method. Furthermore, the drug-loading complexes7b/MgAl-LDHwere prepared and characterized. Their pH-responsive controlled-release behavior was investigated as well. As a result, complex7b/MgAl-LDH-2exhibited excellent controlled-releasing performance in the water/ethanol (10:1, v:v) and under a pH of 5.7.Keywords:longifolene;hydrotalcite;antifungal activity;3D-QSAR;controlled-releasing

CAS / MDL: 75-36-5 534-17-8
研究领域: 有机化学 · 药学 · 材料科学
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SCIENCE OF THE TOTAL ENVIRONMENT · 2019 · IF 5.589

Reducing plant uptake of a brominated contaminant (2,2′,4,4′‑tetrabrominated diphenyl ether) by incorporation of maize straw into horticultural soil

Leilei Xiang,Hongjie Sheng,Min Xu,Marc Redmile-Gordon,Yongrong Bian,Xinglun Yang,Xin Jiang,Fang Wang

Application of crop residues is a conventional practice that contributes to crop production through nutrient returns and other benefits to soil health: driving soil physicochemical and biological functions. However, little is known about the impacts of straw residue incorporation on the bioavailability of organic pollutants and associated changes in microbial community structure in contaminated soils. In this study, maize straw was added to a soil contaminated with a model polybrominated diphenyl ether (BDE-47). A pot experiment was conducted and planted with carrot ( Daucus carota L.). We found that straw addition greatly reduced the bioavailability of BDE-47, changed the bacterial community structure and affected a range of soil physiochemical properties. Moreover, the amount of BDE-47 that had accumulated in carrot roots and aboveground tissues was significantly reduced. This study may therefore describe an effective agronomic strategy to reduce the bioavailability of polybrominated diphenyl ethers (PBDEs) in a soil used to grow high value vegetable crops. This strategy draws on traditional wisdom and shows promise as a practical method to support horticultural production systems, remediate soils, and help to ensure food safety.

研究领域: 农学 · 环境科学 · 土壤微生物学
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