十溴二苯乙烷 | 84852-53-9

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 烃类卤化物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 十溴二苯乙烷
• 中文别名: 十溴化二苯基乙烷2100；1,2-双(2,3,4,5,6-五溴苯基)乙烷；1,1'-(1,2-亚乙基)双[五溴苯]
• 英文名称: 1,2-bis(pentabromophenyl)ethane
• 英文别名: decabromo-1,2-diphenylethane；decabromodiphenyl ethane；decabromodiphenylethane；Firemaster 2100；saytex 8010；DBDPE；1,2-Bis(perbromophenyl)ethane；1,2,3,4,5-pentabromo-6-[2-(2,3,4,5,6-pentabromophenyl)ethyl]benzene
• CAS: 84852-53-9
• 化学式: C₁₄H₄Br₁₀
• 分子量: 971.226
• InChiKey: BZQKBFHEWDPQHD-UHFFFAOYSA-N

物化性质

• 熔点：
  345°C
• 沸点：
  676.2±50.0 °C(Predicted)
• 密度：
  2.816±0.06 g/cm3(Predicted)
• 溶解度：
  二恶烷（微溶，加热）
• LogP：
  3.55 at 25℃
• 物理描述：
  DryPowder; OtherSolid; PelletsLargeCrystals
• 颜色/状态：
  White powder
• 气味：
  Odorless
• 蒸汽压力：
  1.93X10-13 mm Hg at 25 °C (est)

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

代谢

至少在暴露于DBDPE的大鼠中观察到了七种未知化合物，这表明DBDPE在大鼠体内发生了生物转化。通过比较气相色谱/电子电离质谱（GC/EI-MS）和气相色谱/电子捕获负离子化质谱（GC/ECNI-MS）分析中的DBDPE光降解实验得到的脱溴产物的相对保留时间和全扫描质谱，鉴定了这些化合物。结果显示，在大鼠体内观察到的主要代谢途径并不是DBDPE向低溴代BDPEs的脱溴反应。通过GC/EI-MS，两种代谢物被暂时鉴定为MeSO(2)-nona-BDPE和EtSO(2)-nona-BDPE，但它们的结构需要通过其他技术和标准样品进一步确认。此外，大鼠对DBDPE和BDE-209及其代谢物的生物反应证据是不同的。

At least seven unknown compounds were observed in the DBDPE-exposed rats, indicating that DBDPE biotransformation occurred in rats. These compounds were identified by comparing relative retention times and full-scan mass spectra of DBDPE debrominated products from a photolytic degradation experiment using GC/EI-MS and GC/ECNI-MS analysis. The results showed that debromination of DBDPE to lower brominated BDPEs were not the primary metabolic pathway observed in rats. Two of the metabolites were proposed tentatively as MeSO(2)-nona-BDPE and EtSO(2)-nona-BDPE using GC/EI-MS, but their structures require further confirmation by other techniques and authentic standards. In addition, evidence of a biological response to DBDPE and BDE-209 and their metabolites in rats are different.

来源:Hazardous Substances Data Bank (HSDB)

代谢

本研究评估并比较了溴化阻燃剂，包括已知的聚溴二苯醚（PBDEs）和新兴的十溴二苯基乙烷（DBDPE）的氧化还原生物转化，使用基于各种北极海洋哺乳动物肝脏微粒体的体外系统：北极熊（Ursus maritimus）、白鲸（Delphinapterus leucas）和环斑海豹（Pusa hispida），以及作为哺乳动物模型物种的实验室大鼠。与较低溴化PBDEs（BDEs 99, 100和154；30 pmol的0-3%）相比，所有物种个体中完全溴化的BDE209（30 pmol的14-25%）和DBDPE（90 pmol的44-74%）的消耗量更大。没有观察到简单脱溴代谢物的证据。在大鼠和北极熊中调查酚代谢物揭示了在北极熊中形成了两种酚类、可能是多次脱溴的DBDPE代谢物，以及在北极熊和大鼠微粒体中形成了一种酚类BDE154代谢物。尽管BDE209和DBDPE的母体消耗量很大，但观察到的代谢物浓度很低或无法检测。这些发现表明可能低估了总BDE209及其转化产物对生态系统的负担，并需要研究来识别和表征主要BDE209代谢物的持久性和毒性。鉴于DBDPE与BDE209在物理化学性质、环境行为上的相似性，目前生物转化的证据以及DBDPE作为BDE209替代品的日益使用，类似的担忧可能也适用于DBDPE。

The present study assessed and compared the oxidative and reductive biotransformation of brominated flame retardants, including established polybrominated diphenyl ethers (PBDEs) and emerging decabromodiphenyl ethane (DBDPE) using an in vitro system based on liver microsomes from various arctic marine-feeding mammals: polar bear (Ursus maritimus), beluga whale (Delphinapterus leucas), and ringed seal (Pusa hispida), and in laboratory rat as a mammalian model species. Greater depletion of fully brominated BDE209 (14-25% of 30 pmol) and DBDPE (44-74% of 90 pmol) occurred in individuals from all species relative to depletion of lower brominated PBDEs (BDEs 99, 100, and 154; 0-3% of 30 pmol). No evidence of simply debrominated metabolites was observed. Investigation of phenolic metabolites in rat and polar bear revealed formation of two phenolic, likely multiply debrominated, DBDPE metabolites in polar bear and one phenolic BDE154 metabolite in polar bear and rat microsomes. For BDE209 and DBDPE, observed metabolite concentrations were low to nondetectable, despite substantial parent depletion. These findings suggested possible underestimation of the ecosystem burden of total-BDE209, as well as its transformation products, and a need for research to identify and characterize the persistence and toxicity of major BDE209 metabolites. Similar cause for concern may exist regarding DBDPE, given similarities of physicochemical and environmental behavior to BDE209, current evidence of biotransformation, and increasing use of DBDPE as a replacement for BDE209.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

鉴別和使用：十溴二苯基乙烷（DBDPE）曾被用作十溴联苯醚（BDE-209）的替代品，因此目前它在或多或少与BDE-209相同的应用中使用，例如用于生产塑料（包括聚酯和乙烯基酯树脂）和橡胶产品，以及与纺织品和皮革制造相关的不同应用。这种化合物也存在于用于电子和电气应用的聚合物中。DBDPE还可能用于粘合剂和密封剂。人体研究：在HepG2细胞体外试验中，DBDPE具有细胞毒性，具有抗增殖作用，细胞凋亡伴随着活性氧种类的过度产生。动物研究：雄性大鼠口服给予100 mg/kg DBDPE，持续90天。结果显示DBDPE存在于所有组织中。在DBDPE暴露的大鼠中至少观察到七种未知化合物，表明DBDPE在大鼠体内发生了生物转化。用DBDPE处理30天的小鼠，高剂量治疗组的天门冬氨酸转氨酶（ALT）和丙氨酸转氨酶（AST）水平显著升高。治疗组的血糖水平高于对照组。还观察到促甲状腺激素（TSH）、三碘甲状腺原氨酸（T3）和游离T3（fT3）的增加。尿苷二磷酸葡萄糖醛酸基转移酶（UDPGT）、7-戊氧基香豆素O-脱戊基酶（PROD）和乙氧基香豆素-O-脱乙基酶（EROD）活性在高剂量组中显著增加。组织病理学肝脏变化的特点是肝细胞肥大和细胞质空泡化。在大鼠中，DBDPE诱导氧化应激，升高血糖水平，增加CYP2B2 mRNA、CYP2B1/2蛋白、PROD活性，并诱导CYP3A2 mRNA、CYP3A2蛋白和荧光素苄基醚脱苄基酶（LBD）活性。在给予DBDPE剂量高达1,250 mg/kg-day的大鼠或兔子上，没有观察到母体毒性、发育毒性或致畸性的证据。在细菌试验（Ames/鼠伤寒沙门氏菌和大肠杆菌WP2反向突变试验）中，DBDPE不具有致突变性，并且在中国仓鼠肺细胞中没有报告染色体畸变。生态毒性研究：在草鱼（Ctenopharyngodon idella）中，暴露于DBDPE后，有5种miRNAs显著下调，36种miRNAs显著上调，表明miRNAs有潜力用作生物标志物。基于从隔离的雄性肝细胞中合成和分泌卵黄蛋白的鱼肝细胞试验，在DBDPE存在下产生了清晰的剂量-反应曲线。DBDPE在低测试浓度下诱导了肝细胞EROD活性的诱导，但在高浓度下开始抑制活性。此外，诱导肝细胞结合活性UDP-GT被诱导，即使在最高测试浓度下也没有抑制的迹象。EROD活性的降低导致细胞产生的卵黄蛋白减少。体内试验表明，DBDPE对水蚤具有急性毒性，48小时EC-50值为19微克/升。此外，DBDPE降低了暴露的斑马鱼卵的孵化率，并显著提高了孵化幼体的死亡率。与处理相关的影响被识别为E. fetida繁殖、C. sativa存活和L. esculentum和A. cepa高度和干重。最敏感的终点是A. cepa的高度和干重降低以及E. fetida繁殖减少。

IDENTIFICATION AND USE: Decabromodiphenyl ethane (DBDPE) has been used as a substitute for decabrominated diphenyl ether (BDE-209) and therefore it is currently used in more or less the same applications as BDE-209, such as manufacture of plastics (including polyester and vinyl ester resins) and rubber products, as well as in different applications related to manufacture of textiles and leather. This compound is also found in polymers used for electronic and electrical applications. DBDPE could also be used in adhesives and sealants. HUMAN STUDIES: When tested in vitro in HepG2 cells, DBDPE was cytotoxic with anti-proliferation effect and apoptosis was accompanied with overproduction of reactive oxygen species. ANIMAL STUDIES: Male rats were orally administrated with 100 mg/kg DBDPE for 90 days. Results showed DBDPE was found in all tissues. At least seven unknown compounds were observed in the DBDPE-exposed rats, indicating that DBDPE biotransformation occurred in rats. In mice treated with DBDPE for 30 days the levels of alanine aminotransferase or ALT and aspartate aminotransferase or AST of higher dose treatment groups were markedly increased. Blood glucose levels of treatment groups were higher than those of control group. There was also an induction in TSH, T3, and fT3. Uridinediphosphoglucuronosyltransferase (UDPGT), 7-pentoxyresorufin O-depentylase (PROD), and ethoxyresorufin-O-deethylase (EROD) activities were found to have been increased significantly in the high dose group. Histopathologic liver changes were characterized by hepatocyte hypertrophy and cytoplasmic vacuolization. In rats, DBDPE induced oxidative stress, elevated blood glucose levels, increased CYP2B2 mRNA, CYP2B1/2 protein, PROD activity, and induced CYP3A2 mRNA, CYP3A2 protein, and luciferin benzylether debenzylase (LBD) activity. No evidence of maternal toxicity, developmental toxicity, or teratogenicity was observed in rats or rabbits treated with DBDPE at dosage levels up to 1,250 mg/kg-day. DBDPE was not genotoxic in bacterial assays (Ames/Salmonella typhimurium and Escherichia coli WP2 reverse mutation assays) and no chromosomal aberrations were reported in Chinese hamster lung cells. ECOTOXICITY STUDIES: In Grass carp (Ctenopharyngodon idella) 5 miRNAs were significantly down-regulated and 36 miRNAs were significantly up-regulated after DBDPE exposure indicating that miRNAs have potential for use as biomarkers. The fish hepatocyte assay, based on the synthesis and secretion of vitellogenin from isolated male liver cells produced a clear dose-response curve in the presence of DBDPE. DBDPE induced the induction of hepatic EROD activity at low test concentrations, but started to inhibit the activity at higher concentrations. Also, the induction of the hepatocyte conjugation activity, UDPGT, was induced with no signs of inhibition even at the highest test concentration. The reduced EROD activity resulted in a drop in the production of vitellogenin by the cells. In vivo tests showed that DBDPE was acutely toxic to water fleas, the 48 hr EC-50 value being 19 ug/L. Moreover, DBDPE reduced the hatching rates of exposed zebra-fish eggs and raised significantly the mortality of hatched larvae. Treatment-related effects were identified for E. fetida reproduction, C. sativa survival, and L. esculentum and A. cepa height and dry weight. The most sensitive endpoints were decreased height and dry weight for A. cepa and decreased reproduction for E. fetida.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 立即急救：确保已经进行了充分去污。如果患者停止呼吸，开始人工呼吸，最好使用需求阀复苏器、气囊面罩装置或口袋面罩，按培训操作。如有必要，执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果发生呕吐，让患者向前倾或放在左侧（如果可能的话，头部向下）以保持呼吸道畅通，防止吸入。保持患者安静，维持正常体温。寻求医疗帮助。 /毒物A和B/

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 基本治疗：建立专利气道（如有需要，使用口咽或鼻咽气道）。如有必要，进行吸痰。观察呼吸不足的迹象，如有需要，辅助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，如有必要，进行治疗……。监测休克，如有必要，进行治疗……。预防癫痫发作，如有必要，进行治疗……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用0.9%的生理盐水（NS）持续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能吞咽、有强烈的干呕反射且不流口水，则用温水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释……。在去污后，用干燥的无菌敷料覆盖皮肤烧伤……。/毒药A和B/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 高级治疗：对于昏迷、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽插管以控制气道。使用带气囊的面罩进行正压通气技术可能有益。考虑使用药物治疗肺水肿……。对于严重的支气管痉挛，考虑给予β激动剂，如沙丁胺醇……。监测心率和必要时治疗心律失常……。开始静脉输注5%葡萄糖水（D5W），保持通路开放，最低流量/ SRP: "To keep open", minimal flow rate /. 如果出现低血容量的迹象，使用0.9%生理盐水（NS）或乳酸钠林格液（LR）。对于伴有低血容量迹象的低血压，谨慎给予液体。注意液体过载的迹象……。用安定（地西泮）或劳拉西泮（阿蒂万）治疗癫痫……。使用丙美卡因氢氯化物协助眼部冲洗……。/毒素A和B/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

/替代和体外测试/ 目的：研究十溴二苯基乙烷（DBDPE）作为十溴二苯基醚替代品在体外的毒性效应。 方法：将HepG2细胞在不同浓度的DBDPE（3.125-100.0毫克/升）中培养24、48和72小时，研究DBDPE的毒性效应。 结果：通过3-(4,5-二甲基噻唑-2-基)-2,5-二苯基四氮唑溴盐和乳酸脱氢酶分析以及细胞核形态变化评估，DBDPE在12.5毫克/升至100毫克/升的浓度范围内，以及48小时和72小时内，以时间和剂量依赖性的方式抑制了HepG2的细胞活力。在48小时和72小时，12.5-100毫克/升的浓度下通过碘化丙啶染色检测到凋亡的诱导，伴随着活性氧种（ROS）的过量产生。此外，N-乙酰-L-半胱氨酸，一种广泛使用的ROS清除剂，显著降低了DBDPE诱导的ROS水平并增加了HepG2细胞的活力。 结论：DBDPE具有细胞毒性和抗增殖效应，并且能够诱导凋亡，其中ROS起着重要作用。

/ALTERNATIVE and IN VITRO TESTS/ OBJECTIVE: To investigate the toxic effects of decabromodiphenyl ethane (DBDPE), used as an alternative to decabromodiphenyl ether in vitro. METHODS: HepG2 cells were cultured in the presence of DBDPE at various concentrations (3.125-100.0 mg/L) for 24, 48, and 72 hr respectively and the toxic effect of DBDPE was studied. RESULTS: As evaluated by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide and lactate dehydrogenase assays and nuclear morphological changes, DBDPE inhibited HepG2 viability in a time- and dose-dependent manner within a range of 12.5 mg/L to 100 mg/L and for 48 hr and 72 hr. Induction of apoptosis was detected at 12.5-100 mg/L at 48 h and 72 hr by propidium iodide staining, accompanied with overproduction of reactive oxygen species (ROS). Furthermore, N-acetyl-L-cysteine, a widely used ROS scavenger, significantly reduced DBDPE-induced ROS levels and increased HepG2 cells viability. CONCLUSION: DBDPE has cytotoxic and anti-proliferation effect and can induce apoptosis in which ROS plays an important role.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

DBDPE和BDE-209在大鼠体内的分布和毒性研究

Male rats were orally administrated with corn oil containing 100 mg/kg bw/day of DBDPE or BDE-209 for 90 days, after which the levels of DBDPE and BDE-209 in the liver, kidney, and adipose were measured. Biochemical parameters, including thyroid hormone levels, 13 clinical chemistry parameters, and the mRNA expression levels of certain enzymes were also monitored. Results showed DBDPE was found in all tissues with concentrations 3-5 orders of magnitude lower than BDE-209.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

我们检查了加拿大谢布鲁克地区在2008-2009年收集的人体母血清（n = 102）和母乳（n = 105）中的几种新兴溴化阻燃剂（BFRs），包括2-乙基-1-己基-2,3,4,5-四溴苯甲酸酯（TBB）、双（2-乙基己基）四溴邻苯二甲酸酯（TBPH）、1,2-双（2,4,6-三溴苯氧基）乙烷（BTBPE）、4,5,6,7-四溴-1,1,3-三甲基-3-（2,3,4,5-四溴苯基）-茚（OBIND）和十溴二苯基乙烷（DBDPE）。为了比较，研究中还包含了三种传统的BFRs：十溴联苯（BB-209）、2,2',4,4',5,5'-六溴联苯（BB-153）和2,2',4,4',5,5'-六溴二苯醚（BDE-153）。TBB、BB-153和BDE-153在血清和奶样中的检测频率均超过55%。它们在血清和奶中的脂肪重量（lw）调整后的中值浓度（ng g(-1) lw）分别为TBB 1.6和0.41，BB-153 0.48和0.31，BDE-153 1.5和4.4。血清和奶中检测到的其他BFRs的频率分别为TBPH 16.7%和32.4%，BTBPE 3.9%和0.0%，BB-209 2.0%和0.0%，OBIND 9.8%和1.0%，DBDPE 5.9%和8.6%。血清中TBB与TBB和TBPH总和的比值（fTBB）（0.23）低于奶中的比值（0.46），表明TBB比TBPH更容易从血液重新分布到奶中。总的来说，这些数据证实了人体中存在非PBDE BFRs，并需要更好地了解它们的来源、暴露途径和潜在的人类健康影响。

/MILK/ We have examined several emerging brominated flame retardants (BFRs) including 2-ethyl-1-hexyl-2,3,4,5-tetrabromobenzoate (TBB), bis(2-ethylhexyl) tetrabromophthalate (TBPH), 1,2-bis(2,4,6-tribromophenoxy) ethane (BTBPE), 4,5,6,7-tetrabromo-1,1,3-trimethyl-3-(2,3,4,5-tetrabromophenyl)-indane (OBIND), and decabromodiphenyl ethane (DBDPE) in paired human maternal serum (n = 102) and breast milk (n = 105) collected in 2008-2009 in the Sherbrooke region in Canada. Three legacy BFRs were also included in the study for comparison: decabromobiphenyl (BB-209), 2,2',4,4',5,5'-hexabromobiphenyl (BB-153), and 2,2',4,4',5,5'-hexabromodiphenyl ethers (BDE-153). TBB, BB-153, and BDE-153 had detection frequencies greater than 55% in both serum and milk samples. Their lipid weight (lw) adjusted median concentrations (ng g(-1) lw) in serum and milk were 1.6 and 0.41 for TBB, 0.48 and 0.31 for BB-153, and 1.5 and 4.4 for BDE-153, respectively. The detection frequencies for the other BFRs measured in serum and milk were 16.7% and 32.4% for TBPH, 3.9% and 0.0% for BTBPE, 2.0% and 0.0% for BB-209, 9.8% and 1.0% for OBIND, and 5.9% and 8.6% for DBDPE. The ratio of TBB over the sum of TBB and TBPH (fTBB) in serum (0.23) was lower than that in milk (0.46), indicating TBB has a larger tendency than TBPH to be redistributed from blood to milk. Overall, these data confirm the presence of non-PBDE BFRs in humans, and the need to better understand their sources, routes of exposure, and potential human health effects

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

十溴二苯基乙烷（DBDPE），作为十溴二苯基醚（deca-BDE）的替代品，在中国圈养的中国短吻鳄中进行了研究。在成年鳄鱼的组织、幼鳄和鳄鱼蛋中均检测到了DBDPE，其浓度分别为4.74-192、0.24-1.94和0.01-0.51 ng g(-1) 脂肪重量。与PBDEs（多溴联苯醚）和PCBs（多氯联苯）相比，中国短吻鳄中的DBDPE污染有限。此外，成年鳄鱼肌肉中的DBDPE浓度比幼鳄和鳄鱼蛋中的浓度高出1到3个数量级，这表明在中国短吻鳄中DBDPE的母体传递潜力有限。

Decabromodiphenyl ethane (DBDPE), a replacement for decabromodiphenyl ether (deca-BDE), was investigated in captive Chinese alligators from China. DBDPE was detected in adult tissues, neonates and eggs of Chinese alligators with concentrations ranging from 4.74-192, 0.24-1.94, and 0.01-0.51 ng g(-1) lipid weight, respectively. Compared to PBDEs and PCBs, DBDPE contamination was limited in Chinese alligators. Additionally, DBDPE concentrations in adult muscles were one to three orders of magnitude higher than those in neonates and eggs, suggesting the limited maternal transfer potential of DBDPE in Chinese alligators. ...

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

母鸡肌肉、鸡蛋以及新生小鸡组织（肌肉和肝脏）是从中国南方的一个电子废物回收站收集的。作者们检查了在鸡蛋形成和小鸡胚胎发育过程中，几种卤化阻燃剂（HFRs）的母体传递、潜在代谢和在不同组织中的分布。从母鸡肌肉到鸡蛋，以及从鸡蛋到新生小鸡组织的污染物组成有显著变化。高卤素含量的化学物质，如八到十溴联苯醚（PBDE）同系物、十溴联苯（PBB209）和得克隆Plus（DP），相比于低卤素含量的化学物质，更不易传递到鸡蛋中。在胚胎发育过程中，PBDEs最有可能被代谢，而十溴二苯基乙烷（DBDPE）则最不易被代谢。作者们还观察到在鸡胚胎发育过程中，抗-DP的母体传递选择性和对映选择性代谢。在组织发育过程中，除了DBDPE外，肝脏比肌肉对具有高辛醇-水分配系数的化学物质有更大的亲和力。鸡胚胎中不同化学物质代谢潜力的差异导致了污染物组成的改变。来自母体传递和组织分布的卤化阻燃剂也表现出化学特异性，特别是对于DBDPE。从母鸡肌肉到鸡蛋，再到小鸡组织，DBDPE的水平持续升高……

Hen muscle, eggs, and newborn chick tissues (muscle and liver) were collected from an electronic waste recycling site in southern China. The authors examined the maternal transfer, potential metabolism, and tissue distribution of several halogenated flame retardants (HFRs) during egg formation and chicken embryo development. The pollutant composition changes significantly from hen muscle to eggs and from eggs to tissues of newborn chicks. Higher-halogenated chemicals, such as octa- to deca-polybrominated diphenyl ether (PBDE) congeners, deca-polybrominated biphenyl (PBB209), and dechlorane plus (DP), are less readily transferred to eggs compared with lower-halogenated chemicals. During embryo development, PBDEs are the most likely to be metabolized, whereas decabromodiphenyl ethane (DBDPE) is the least. The authors also observed selective maternal transfer of anti-DP and stereoselective metabolism of syn-DP during chicken embryo development. During tissue development, liver has greater affinity than the muscle for chemcials with a high log octanol-water partition coefficient, with the exception of DBDPE. The differences in metabolism potential of different chemicals in chicken embryos cause pollutant composition alterations. Halogenated flame retardant from maternal transfer and tissue distribution also exhibited chemical specificity, especially for DBDPE. Levels of DBDPE were elevated along with the full process from hen muscle to eggs and from eggs to chick tissues. ...

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

多溴联苯醚（PBDEs）和十溴二苯基乙烷（DBDPE）的广泛使用使它们成为无生命环境中的普遍污染物，但关于它们对底栖生物的生物有效性的数据却很少。本研究评估了从现场采集的沉积物中PBDEs和DBDPE在寡毛虫Lumbriculus variegatus中的生物累积潜力，使用了一个49天的暴露期，包括28天的吸收期和21天的排出期。所有的PBDEs和DBDPE都对虫子具有生物有效性，生物体-沉积物累积因子（BSAFs）的范围从0.0210 g有机碳/g脂质到4.09 g有机碳/g脂质。然而，与其它PBDEs相比，高度溴化的化合物（BDE-209和DBDPE）的生物有效性较差，这通过它们相对较低的自由溶解浓度（C(free)）得以确认，这些浓度是通过固相微萃取测量的。BSAFs与疏水性的反比关系可以用它们的吸收（k(s)）和排出（k(e)）速率常数来解释。虽然PBDEs的ke变化很小，但当化学疏水性增加时，ks显著降低。溴化阻燃剂在鱼类和虫子中的生物累积动力学差异可以用它们的生理差异和存在多种排出途径来解释。28天生物累积测试对PBDEs和DBDPE的BSAF估计的适当性得到了验证。此外，C(free)被证明是生物有效性的良好指标。

The extensive use of polybrominated diphenyl ethers (PBDEs) and decabromodiphenyl ethane (DBDPE) has made them widespread contaminants in abiotic environments, but data regarding their bioavailability to benthic organisms are sparse. The bioaccumulation potential of PBDEs and DBDPE from field-collected sediment was evaluated in the oligochaete Lumbriculus variegatus using a 49-d exposure, including a 28-d uptake and a 21-d elimination phase. All PBDEs and DBDPE were bioavailable to the worms with biota-sediment accumulation factors (BSAFs) ranging from 0.0210 g organic carbon/g lipid to 4.09 g organic carbon/g lipid. However, the bioavailability of highly brominated compounds (BDE-209 and DBDPE) was poor compared with that of other PBDEs, and this was confirmed by their relatively low freely dissolved concentrations (C(free)) measured by solid-phase microextraction. The inverse correlation between BSAFs and hydrophobicity was explained by their uptake (k(s)) and elimination (k(e)) rate constants. While ke changed little for PBDEs, ks decreased significantly when chemical hydrophobicity increased. The difference in bioaccumulation kinetics of brominated flame retardants in fish and the worms was explained by their physiological difference and the presence of multiple elimination routes. The appropriateness of 28-d bioaccumulation testing for BSAF estimation was validated for PBDEs and DBDPE. In addition, C(free) was shown to be a good indicator of bioavailability.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 海关编码：
  2903999090
• RTECS号：
  DA0358200
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

产品优点

十溴二苯乙烷在常温常压下为白色固体粉末，微溶于醇类有机溶剂，不溶于水。它具有极优异的热稳定性和极高的溴含量，还具备抗紫外线能力强、毒性低等优点，是一种新型环保型阻燃剂。

结构性质

十溴二苯乙烷结构中含有十个溴原子，拥有极其高的溴含量和良好的热稳定性及抗紫外线性能，其渗出性较低。该物质在热裂解或燃烧时不产生有毒的多溴代二苯并二恶烷（PBDO）及多溴代二苯并呋喃（PBDF），符合欧洲关于二恶英条例的要求，对环境无害。

化学性质

十溴二苯乙烷外观为白色或淡黄色粉末，熔点在335-342℃之间，微溶于醇和醚中，几乎不溶于水。

用途

本品主要用于取代传统的十溴二苯醚阻燃剂，并广泛应用于HIPS、ABS树脂以及PVC、PP等塑料制品中。它是一种新型、广谱、高效且环保型的阻燃剂，具有极优异的热稳定性和极高的溴含量，还具备抗紫外线能力强和低毒性的优点，适用于多种材料如苯乙烯类高聚物、工程热塑性塑料、电线电缆包覆物、绝缘体、弹性体以及热固性塑料等。

反应信息

• 作为反应物：
  描述：

  十溴二苯乙烷 在 cadmium selenide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以32%的产率得到1,2-二苯乙烷
  参考文献：
  名称：

  一种光催化多卤代物的碳卤键C-R向碳氢/氘键C-H/D的转化方法

  摘要：

  本发明公开了一种光催化多卤代物的碳卤键C‑R向碳氢/氘键C‑H/D转化方法，包括以下步骤：将光催化剂量子点/棒加入溶剂中，得溶液A；将多卤代物和电子牺牲体加入溶液A中，得溶液B；用光源照射溶液B，催化进行多卤代物脱卤转化。本发明是首次将纳米量子点和纳米量子棒用于多卤代物的脱卤转化反应，反应条件温和，以可见光为驱动能，产物为完全脱卤的烃类化合物，整个过程绿色、简洁、高效。本发明将多卤代物脱卤转化和氘代标记过程合并进行，完成多个C‑R键向C‑D键转化，一步实现多原子的氘代标记。

  公开号：

  CN110204425A
• 作为产物：
  描述：

  1,2-二苯乙烷 在 aluminum (III) chloride 溴 作用下， 以 二溴甲烷 为溶剂， 反应 2.0h， 生成 十溴二苯乙烷
  参考文献：
  名称：

  PREPARATION AND PROVISION OF HIGH ASSAY DECABROMODIPHENYLETHANE

  摘要：

  生产和提供高纯度反应衍生的十溴联苯乙烷产品。该过程包括将二苯乙烷、部分溴化的二苯乙烷或两者的混合物输送到由含有过量液态溴和基于铝的Lewis酸溴化催化剂组成的反应混合物的液相中。在这些过程中，反应混合物的温度、过量溴中的催化剂浓度以及进料时间是协调的，以生产高纯度反应衍生的十溴联苯乙烷产品。描述了实现这种协调的方法。

  公开号：

  US20080228015A1

文献信息

• Reaction of 2,3,4,5,6-pentabromobenzyl bromide with 2,4,6-triphenylpyranyl
  作者：A. A. Burtasov、A. N. Mishunyaeva、M. K. Pryanichnikova、V. N. Shishkin、B. S. Tanaseichuk

  DOI：10.1007/s11176-005-0019-2

  日期：2004.9

  The main process in the reaction of 2,4,6-triphenylpyranyl with 2,3,4,5,6-pentabromobenzyl bromide in 2-propanol is electron transfer to give 2,4,6-triphenylpyrylium bromide and 2,3,4,5,6-pentabromobenzyl radical.

  2,4,6-三苯基吡喃与2,3,4,5,6-五溴苄基溴在异丙醇中的主要反应过程是电子转移，生成2,4,6-三苯基吡喃鎓溴化物和2,3,4,5,6-五溴苄基自由基。
• [EN] FLAME RETARDANTS, PREPARATION METHODS, AND THERMOPLASTIC COMPOSITIONS THEREOF<br/>[FR] AGENTS IGNIFUGEANTS, LEURS PROCÉDÉS DE PRÉPARATION ET COMPOSITIONS THERMOPLASTIQUES ASSOCIÉES
  申请人：DUPONT CHINA RES & DEV AND MAN CO LTD

  公开号：WO2015180165A1

  公开（公告）日：2015-12-03

  Disclosed are flame retardants comprising compounds of Formula (1), wherein the polyol is a disaccharide or a C12 sugar alcohol, which has at least one glucose or one fructose unit per molecule, R1is H or CH3;R2is H or CH3;mis an integer ranging from 6 to 9; and n is an integer ranging from 2 to 9. Also disclosed are methods for producing the inventive flame retardants, thermoplastic compositions and articles comprising the same, and methods for improving flame retardancy of thermoplastic polymers using the same.

  揭示了包括式（1）化合物的阻燃剂，其中多元醇是二糖或C12糖醇，每个分子至少含有一个葡萄糖或一个果糖单位，R1为H或CH3；R2为H或 ；m为6至9的整数；n为2至9的整数。还公开了制备新型阻燃剂的方法，含有该阻燃剂的热塑性组合物和制品，以及利用该阻燃剂改善热塑性聚合物的阻燃性的方法。
• Flame retardants for use in styrenic foams
  申请人：Hanson Mark V.

  公开号：US20080221230A1

  公开（公告）日：2008-09-11

  The invention is a flame retardant for styrene foams. The flame retardant contains both aromatic bromine and an olefin. The olefin is an internal olefin. Desirable flame retardants are selected from: formula I: wherein R 1 is C 1 -C 6 and optionally containing a heteroatom or olefin; R 2 is C 1 -C 6 and optionally containing a heteroatom or olefin; and R 3 -R 12 is H, C 1 -C 6 (optionally containing a heteroatom), or halogen; and further wherein the compound of formula I is present in a concentration of at least 50 percent of a trans isomer; formula II: wherein R 1 is Halogen, C 1 -C 6 and optionally containing a heteroatom or olefin; R 2 is Halogen, C 1 -C 6 and optionally containing a heteroatom or olefin; and R 3 -R 7 is H, C 1 -C 6 (optionally containing a heteroatom), or halogen; and formula III: wherein R 1 is Halogen, C 1 -C 6 and optionally containing a heteroatom or olefin; R 2 is Halogen, H, C 1 -C 6 and optionally containing a heteroatom or olefin; and R 3 -R 6 is H, halogen.

  这项发明是用于苯乙烯泡沫的阻燃剂。该阻燃剂含有芳香溴和烯烃。烯烃是内烯烃。从以下理想的阻燃剂中选择：公式I：其中R1是C1-C6，可选地含有杂原子或烯烃；R2是C1-C6，可选地含有杂原子或烯烃；R3-R12是H，C1-C6（可选地含有杂原子），或卤素；进一步，公式I的化合物以至少50%的反式异构体的浓度存在；公式II：其中R1是卤素，C1-C6，可选地含有杂原子或烯烃；R2是卤素，C1-C6，可选地含有杂原子或烯烃；R3-R7是H，C1-C6（可选地含有杂原子），或卤素；和公式III：其中R1是卤素，C1-C6，可选地含有杂原子或烯烃；R2是卤素，H，C1-C6，可选地含有杂原子或烯烃；R3-R6是H，卤素。
• Process for separation of bromine from gaseous hydrogen bromide and use of such process in production of decabromodiphenylethane
  申请人：Albemarle Corporation

  公开号：US07408088B1

  公开（公告）日：2008-08-05

  Bromine is scrubbed from a gaseous mixture of bromine and hydrogen bromide by passing the mixture into a mixture formed from (i) diphenylethane and/or partially brominated diphenylethane with average bromine number less than about 2 and (ii) a catalytic quantity of iron and/or iron halide in which the halogen atoms are bromine atoms and/or chlorine atoms. Component (i) is brominated, and during such bromination, the mixture is kept hot enough to melt the organics to provide a liquid phase in the scrubber. Gaseous mixtures of bromine and hydrogen bromide are formed in processes of the invention in which decabromodiphenylethane products are produced using the partially brominated diphenylethane as feed to the bromination, which is conducted using an aluminum-based catalyst. Effective ways of removing iron catalyst residues from partially brominated diphenylethane or from decabromodiphenylethane product are also described.

  溴从溴氢混合气中通过将混合气体通过由（i）二苯乙烷和/或平均溴数小于约2的部分溴化二苯乙烷和（ii）铁和/或卤化铁的催化量形成的混合物中进行洗涤来清除。组分（i）被溴化，而在这种溴化过程中，混合物被保持足够热以熔化有机物质以在洗涤器中提供液相。本发明的过程中形成了溴和溴化氢的混合气体，其中使用部分溴化二苯乙烷作为供料进行溴化，该溴化使用基于铝的催化剂进行。还描述了从部分溴化二苯乙烷或十溴二苯乙烷产品中有效去除铁催化剂残留的方法。
• FLAME RETARDANT HALOGENATED PHENYL ETHERS
  申请人：Timberlake Larry D.

  公开号：US20110184107A1

  公开（公告）日：2011-07-28

  A halogenated non-polymeric phenyl ether is described having the general formula (I): wherein each X is independently Cl or Br, n is an integer of 1 or 2, each m is independently an integer of 1 to 5 and each p is independently an integer of 1 to 4, provided that, when X is Cl, the total amount halogen in the ether is from about 50 to about 65 wt % and when, X is Br, the total amount halogen in the ether is from at least 70 wt % to about 79 wt %.

  描述了一种卤代非聚合苯醚，其一般式为(I)：其中每个X独立地为Cl或Br，n为1或2的整数，每个m独立地为1至5的整数，每个p独立地为1至4的整数，但当X为Cl时，醚中卤素的总量约为50至65重量％，当X为Br时，醚中卤素的总量至少为70重量％至约79重量％。

表征谱图