四溴苯氧基五溴苯 | 63936-56-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 四溴苯氧基五溴苯
• 英文名称: nonabromodiphenyl ether
• 英文别名: 2,2′,3,3′,4,4′,5,5′,6-nonabromodiphenyl ether；2,2',3,3',4,4',5,5',6-nonabromo diphenyl ether；2,2',3,3',4,4',5,5',6-nonabromodiphenyl ether；2,2',3,3',4,4',5,5',6-nonabromodiphenylether；BDE-206；nonabromodiphenyl oxide；1,2,3,4,5-pentabromo-6-(2,3,4,5-tetrabromophenoxy)benzene
• CAS: 63936-56-1
• 化学式: C₁₂HBr₉O
• 分子量: 880.275
• InChiKey: CYRHBNRLQMLULE-UHFFFAOYSA-N

物化性质

• 碰撞截面：
  202.1 Ų [M-Br+O]-

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

代谢

多溴联苯可以通过口服、吸入和皮肤途径被吸收。一旦进入人体，它们会分布到全身并在血液、母乳和脂肪组织中生物累积。PBDE的代谢程度取决于溴化的程度。代谢过程被认为涉及脱溴和甲基化，产生酚类代谢物。代谢和未代谢的PBDE化合物主要通过粪便排出体外。(L628, L881)

Polybrominated biphenyls can be absorbed through oral, inhalation, and dermal routes. Once in the body they distribute throughout and bioaccumulate in the blood, breast milk, and adipose tissue. The extent of PBDE metabolism depends on the degree of bromination. Metabolism is believed to involve debromination and methylation, resulting in phenolic metabolites. Metabolized and unmetabolized PDBE compounds are excreted mainly in the faeces. (L628, L881)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

像其他卤代芳烃一样，多溴联苯醚会与细胞中的芳烃受体（AhR）结合，该受体调控多种蛋白质的合成。AhR的激活会诱导一系列酶的产生，包括细胞色素P-450依赖的单加氧酶CYP1A和CYP2B家族、UDP-葡萄糖醛酸基转移酶以及乙氧基 resorufin-O-脱乙基酶。PBDEs还被认为是干扰甲状腺激素的产生、传输和处置。一种机制涉及PBDEs的代谢物与甲状腺素竞争结合transthyretin，降低血清甲状腺激素水平。甲状腺激素水平的变化与甲状腺毒性和神经行为改变有关。某些PBDEs及其代谢物也是内分泌干扰物，可能作为雌激素受体的激动剂或作为雄激素和黄体酮受体的拮抗剂。

Like other halogenated aromatic hydrocarbons, polybrominated diphenyl ethers bind to the cellular aryl hydrocarbon receptor (AhR), which regulates the synthesis of a variety of proteins. Activation of the AhR induces a number of enzymes, including cytochrome P-450-dependent monooxygenases of the CYP1A and CYP2B families, UDP-glucuronosyltransferase, and ethoxyresorufin-o-deethylase. PBDEs are also believed to disrupt the production, transport, and disposition of thyroid hormones. One mechanism of this involves metabolites ot PDBEs competing with thyroxine to bind to transthyretin, decreasing serum thyroid hormone levels. This change in thyroid hormone levels has been linked to both thyroid toxicity and neurobehavioral alterations. Certain PDBEs and their metabolites are also endocrine disruptors and may act as agonists at the estrogen receptors or antagonists at the androgen and progesterone receptors. (L628, A262)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

多溴联苯醚可能会影响甲状腺和肝脏。动物研究也表明，PDBEs可以导致神经行为改变并影响免疫系统。

Polybrominated diphenyl ethers may affect the thyroid gland and liver. Animals studies have also shown that PDBEs can cause neurobehavioral alterations and affect the immune system. (L628)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口服（L628）；吸入（L628）；皮肤给药（L628）

Oral (L628) ; inhalation (L628) ; dermal (L628)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 最低风险水平

中间吸入：0.006 毫克/立方米（L134） 急性口服：0.03 毫克/千克/天（L134） 中间口服：0.007 毫克/千克/天（L134）

Intermediate Inhalation: 0.006 mg/m3 (L134) Acute Oral: 0.03 mg/kg/day (L134) Intermediate Oral: 0.007 mg/kg/day (L134)

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 危险等级：
  9
• 包装等级：
  II
• 危险类别：
  9

反应信息

• 作为产物：
  描述：

  十溴二苯醚 生成 四溴苯氧基五溴苯
  参考文献：
  名称：

  WATANABE, ISAO;KASHIMOTO, TAKASHI;TATSUKAWA, RYO, BULL. ENVITRON. CONTAM. AND TOXICOL., 36,(1986) N 6, 839-842

  摘要：

  DOI：

文献信息

• PREPARATION AND PROVISION OF HIGH ASSAY DECABROMODIPHENYLETHANE
  申请人：Hussain Saadat

  公开号：US20080227903A1

  公开（公告）日：2008-09-18

  High assay, reaction-derived decabromodiphenylethane product is prepared by feeding (i) diphenylethane or (ii) partially brominated diphenylethane having an average bromine number less than about two, or (iii) both of (i) and (ii), into the liquid confines of a reaction mixture. Such reaction mixture is (a) formed from components comprised of excess liquid bromine and aluminum-based Lewis acid bromination catalyst, and (b) maintained at one or more elevated reaction temperatures of from about 45°-90° C., and at least when elevated pressure is needed to keep a liquid state in the reaction mixture at the temperature(s) used, the reaction mixture is at such an elevated pressure, whereby ar-bromination occurs. The feeding is conducted at a rate slow enough to form high assay reaction-derived decabromodiphenylethane product, which is an effective flame retardant.

  高纯度，反应制备的十溴二苯乙烷产物是通过将（i）二苯乙烷或（ii）部分溴化的平均溴数小于约2的二苯乙烷，或者（iii）（i）和（ii）两者都投入反应混合物的液态容器中制备的。这种反应混合物由过量的液态溴和基于铝的路易斯酸溴化催化剂组成，并且在约45℃至90℃的一个或多个升高的反应温度下维持，并且至少当需要升高压力以保持反应混合物在使用的温度下处于液态时，反应混合物处于这样的升高压力下，从而发生芳基溴化反应。给料速率足够慢，以形成高纯度的反应制备的十溴二苯乙烷产物，该产物是一种有效的阻燃剂。
• Photochemical Decomposition of 15 Polybrominated Diphenyl Ether Congeners in Methanol/Water
  作者：Johan Eriksson、Nicholas Green、Göran Marsh、Åke Bergman

  DOI：10.1021/es049830t

  日期：2004.6.1

  times shorter than the environmentally abundant congener 2,2',4,4'-tetraBDE (T1/2 = 12 d) in methanol/water. The quantum yields in the methanol/water solution ranged from 0.1 to 0.3. The photochemical reaction of decaBDE is a consecutive debromination from ten- down to six-bromine-substituted PBDEs. Products with less than six bromines were tentatively identified as brominated dibenzofurans and traces

  在所有使用的溴化阻燃剂中，多溴二苯醚（PBDEs）由于其在全球范围内的分布和生物蓄积性而被确定为对环境特别关注，正如在全球人类和野生动植物中观察到的那样。仍然需要更多有关多溴二苯醚基本特征的数据，以更好地理解和描述其环境命运。因此，本研究的目的是研究不同溴化程度的多溴二苯醚的光化学降解。在甲醇/水（8：2）中，通过阳光下的紫外光研究了15种被4-10个溴原子取代的多溴二苯醚的光化学降解。在纯甲醇中还研究了其中的9种，在四氢呋喃中研究了9种多溴二苯醚中的4种。光化学反应速率随着分子中溴取代基数量的减少而降低，但在某些情况下还受到PBDE取代模式的影响。反应速率取决于溶剂，使得在甲醇/水溶液中的反应速率始终比纯甲醇低约1.7倍，比THF低约2-3倍。在甲醇/水中，十溴二苯醚的紫外线降解半衰期（T1 / 2 = 0.5小时）比环境丰富的同族2,2'，4,4'-四溴二苯醚（T1 / 2 = 12
• Rapid, Photocatalytic, and Deep Debromination of Polybrominated Diphenyl Ethers on Pd-TiO₂: Intermediates and Pathways
  作者：Lina Li、Wei Chang、Ying Wang、Hongwei Ji、Chuncheng Chen、Wanhong Ma、Jincai Zhao

  DOI：10.1002/chem.201402477

  日期：2014.8.25

  significant difference between the Pd–TiO2 and pristine TiO2 systems, and much less position selectivity for the debromination on Pd–TiO2 was observed than that on the pristine TiO2 surface. For another polybrominated diphenyl ether (BDE15), pristine TiO2 was incapable of its photocatalytic reduction, whereas the loading of Pd enabled its debromination to diphenyl ether within 20 min. In addition, an evident

  带有表面负载钯的二氧化钛（Pd–TiO 2）在阳光或人工光源的照射下，在1 h内即可轻松地从十溴二苯醚（BDE209）中去除所有十个溴原子。相比之下，即使经过长时间照射（5小时），在原始TiO 2上也可以消除少于三个的溴原子。此外，在光催化脱溴过程中，所形成的BDE中间体在Pd-TiO 2和原始TiO 2体系之间显示出显着差异，并且观察到的脱溴在Pd-TiO 2上的位置选择性比在原始TiO 2表面上的位置选择性小得多。。对于另一种多溴二苯醚（BDE15），原始TiO2不能进行光催化还原，而Pd的负载使其能够在20分钟内脱溴成二苯醚。此外，在Pd-TiO 2上光催化脱溴BDE15出现了明显的诱导期。实验表明，Pd共催化作用会显着改变光催化还原性脱溴途径。
• PREPARATION OF HIGH ASSAY DECABROMODIPHENYL OXIDE
  申请人：Mack Arthur G.

  公开号：US20080058555A1

  公开（公告）日：2008-03-06

  A process is described for producing a reaction-derived decabromodiphenyl oxide product of high purity. In a continuous bromination process, partially brominated diphenyl oxide and coproduct hydrogen bromide are formed by bringing together elemental bromine and diphenyl oxide continuously in a first reaction zone. The partially brominated diphenyl oxide formed has an average of about 2-6 bromine atoms per molecule. The vapor phase and the partially brominated diphenyl oxide are removed continuously from the first reaction zone as separate entities. Then, or after storage, partially brominated diphenyl oxide is fed to a second reaction zone. This zone contains a refluxing reaction mixture comprising (i) an excess of bromine and (ii) a catalytic quantity of Lewis acid bromination catalyst. As the reaction in this zone is taking place, hydrogen bromide coproduct is removed therefrom in a sufficient amount to form a reaction-derived decabromodiphenyl oxide product of high purity.

  描述了一种生产高纯度反应衍生的十溴二苯醚产品的过程。在连续溴化过程中，通过将元素溴和二苯醚不断地在第一反应区域中混合，形成部分溴化的二苯醚和共产物氢溴酸。形成的部分溴化二苯醚平均每分子含有约2-6个溴原子。气相和部分溴化二苯醚连续地从第一反应区域分离出来。然后，或者在存储之后，将部分溴化二苯醚送入第二反应区域。该区域包含一个回流反应混合物，其中包含（i）过量的溴和（ii）催化量的Lewis酸溴化催化剂。当该区域中的反应正在进行时，共产物氢溴酸被以足够的量从中移除，以形成高纯度的反应衍生的十溴二苯醚产品。
• PREPARATION OF DECABROMODIPHENYL OXIDE
  申请人：Mack Arthur G.

  公开号：US20080058558A1

  公开（公告）日：2008-03-06

  This invention provides a process for producing decabromodiphenyl oxide from a liquid mixture. The liquid mixture is derived from bromine, a Lewis acid catalyst, and a diphenyl oxide species selected from the group consisting of (i) diphenyl oxide, (ii) partially brominated diphenyl oxide, (iii) decabromodiphenyl oxide having about 0.5% or more nonabromodiphenyl oxide, and (iv) any combination of (i)-(iii). The process comprises distilling bromine and hydrogen bromide from the liquid mixture while feeding bromine to the liquid mixture.

  该发明提供了一种从液态混合物中制备十溴二苯醚的方法。该液态混合物由溴、路易斯酸催化剂和从以下组中选择的二苯醚种类派生而来：（i）二苯醚，（ii）部分溴化的二苯醚，（iii）含有约0.5％或更多的非溴代二苯醚的十溴二苯醚，以及（iv）（i）-（iii）的任何组合。该过程包括从液态混合物中蒸馏出溴和氢溴酸，同时向液态混合物中加入溴。