1,2,3,7,8-五氯二苯并对二恶英 | 40321-76-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶英
• 中文名称: 1,2,3,7,8-五氯二苯并对二恶英
• 中文别名: 1,2,3,7,8-五氯二苯并-对-二噁英
• 英文名称: 1,2,3,7,8-pentachlorodibenzodioxin
• 英文别名: 1,2,3,7,8-Pentachlorodibenzo-p-dioxin；1,2,3,7,8-PeCDD；1,2,3,7,8-PnCDD；1,2,3,7,8-pentachlorodibenzodioxine
• CAS: 40321-76-4
• 化学式: C₁₂H₃Cl₅O₂
• 分子量: 356.42
• InChiKey: FSPZPQQWDODWAU-UHFFFAOYSA-N

物化性质

• 熔点：
  206°C (estimate)
• 沸点：
  442.63°C (rough estimate)
• 密度：
  1.7800 (estimate)
• 蒸汽压力：
  4.35e-10 mmHg
• 保留指数：
  2574

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

ADMET

代谢

CDDs通过口服、吸入和皮肤暴露途径被吸收。CDDs通过血清脂质和脂蛋白在血浆中运输，主要分布到肝脏和脂肪组织。CDDs通过微粒体单加氧酶系统非常缓慢地被代谢为极性代谢物，这些代谢物可以与葡萄糖醛酸和谷胱甘肽发生结合。它们可能通过诱导I相和II相酶来增加自身代谢的速率。CDDs的主要排泄途径是胆汁和粪便，尽管也有少量通过尿液和哺乳排出。

CDDs are absorbed through oral, inhalation, and dermal routes of exposure. CDDs are carried in the plasma by serum lipids and lipoproteins, distributing mainly to the liver and adipose tissue. CDDs are very slowly metabolized by the microsomal monooxygenase system to polar metabolites that can undergo conjugation with glucuronic acid and glutathione. They may increase the rate of their own metabolism by inducing both phase I and phase II enzymes. The major routes of excretion of CDDs are the bile and the faeces, though smaller amounts are excreted in the urine and via lactation. (L177)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

CDDs通过结合芳基烃受体并随后改变某些基因的转录来产生其毒性作用。对Ah受体的亲和力取决于特定CDD的结构。基因表达的改变可能是由于Ah受体及其异二聚体形成伙伴芳基烃受体核移位子与基因调控元件的直接相互作用，或者启动磷酸化/去磷酸化级联反应，随后激活其他转录因子。受影响的基因包括几个癌基因、生长因子、受体、激素和药物代谢酶。这些基因的转录/翻译改变被认为是CDDs大多数毒性作用的原因。

CDDs cause their toxic effects by binding to the aryl hydrocarbon receptor and subsequently altering the transcription of certain genes. The affinity for the Ah receptor depends on the structure of the specific CDD. The change in gene expression may result from the direct interaction of the Ah receptor and its heterodimer-forming partner, the aryl hydrocarbon receptor nuclear translocator, with gene regulatory elements or the initiation of a phosphorylation/dephosphorylation cascade that subsequently activates other transcription factors. The affected genes include several oncogenes, growth factors, receptors, hormones, and drug-metabolizing enzymes. The change in transcription/translation of these genes is believed to be the cause of most of the toxic effects of CDDs. (L177)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

3, 无法归类其对人类致癌性的类别。(L135)

3, not classifiable as to its carcinogenicity to humans. (L135)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

接触大量氯丹类化合物（CDDs）会导致氯痤疮，这是一种严重的皮肤疾病，其特点是在面部和上半身出现类似粉刺的损伤。CDDs还可能引起肝脏损伤，并导致长期的葡萄糖代谢改变和激素水平的微妙变化。此外，研究还表明CDDs可能会干扰内分泌系统，削弱免疫系统，以及造成生殖损害和出生缺陷、中枢和周围神经系统的病理变化、甲状腺疾病、子宫内膜异位症和糖尿病。(L177, L178)

Exposure to large amounts of CDDs causes chloracne, a severe skin disease with acne-like lesions that occur mainly on the face and upper body. CDDs may also cause liver damage and induce long-term alterations in glucose metabolism and subtle changes in hormonal levels. In addition, studies have shown that CDDs may disrupt the endocrine system and weaken the immune system, as well as cause reproductive damage and birth defects, central and peripheral nervous system pathology, thyroid disorders, endometriosis, and diabetes. (L177, L178)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口服（L177）；吸入（L177）；皮肤（L177）

Oral (L177) ; inhalation(L177) ; dermal (L177)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

除了氯痤疮，CDD暴露还会导致皮肤疹、色素沉着和体毛过度生长。

In addition to chloracne, CDD exposure causes skin rashes, discoloration, and excessive body hair. (L177)

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 危险等级：
  6.1(a)
• 海关编码：
  2932999060
• 危险类别：
  6.1(a)
• 危险品运输编号：
  UN 2811

反应信息

• 作为产物：
  描述：

  lindane 在 氧气 作用下， 生成 1,2,3,7,8-五氯二苯并对二恶英
  参考文献：
  名称：

  Estimation of dioxin emission from fires in chemicals

  摘要：

  The formation of the 17 toxic 2,3,7,8-substituted PCDDs and PCDFs during combustion of selected chemicals were measured by high-resolution GC/MS. The 16 chemicals studied were commonly used chlorinated pesticides, industrial chemicals, and PVC. In a series of experiments carried out in a DIN 53,436 furnace, 2.5 g of these compounds were burned at 500 degrees C and 900 degrees C, respectively. The resultant yields ranged from 740 ng ITEQ/g for pentachlorophenol, to below 0.01 ng ITEQ/g for PVC and dichlobenil. The results show that some chemicals generate PCDD/F in very high possibly dangerous - amounts during burning, whereas others generate insignificant amounts. The influence of scale were studied for chlorobenzene and 4-chloro-3-nitro-benzoic acid in additional experiments, carried out in a cone calorimeter burning 20 g substance, and in ISO 9705 room test burning about 50 kg. A good agreement between the results for large and small scale indicated that formation of PCCD/F during a fire may be estimated from laboratory experiments. This suggest laboratory test may be used to screen for chemicals posing a hazard for release of PCDD/F during fires. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0045-6535(99)00231-3

文献信息

• On Dioxin Formation in Iron Ore Sintering
  作者：Mariusz K. Cieplik、Jose Pastor Carbonell、Christina Muñoz、Sarah Baker、Sophie Krüger、Per Liljelind、Stellan Marklund、Robert Louw

  DOI：10.1021/es026292g

  日期：2003.8.1

  sintering facility could satisfactorily imitate the large-scale process, in part or as a whole. Results obtained with realistic feed mixtures point at dioxin formation in the sinter bed at levels significant enough to explain a major part of the outputs observed in the real-life process. With approximately 8 ppm (wt) of chloride added as NaCl, the PCDD/F output doubled, but with the same proportion of

  铁矿石烧结是“二恶英”，多氯二苯并对二恶英和二苯并呋喃（PCDD / Fs）的重要来源。本文报道了尝试确定造成PCDD / F形成的材料，条件和机理的尝试（i）通过研究矿石的显着特性（即关于模型有机物的氧化，冷凝和氯化），以及（ii）使用现实生活的材料在微观尺度上模拟工业过程。采用实验设计原理（DOE）。铁矿石的反应性差异很大。褐铁矿/针铁矿“软”矿石是一种非常活泼的氧化催化剂（例如，用于苯和苯酚），该特性可用于清除粗烧结工艺废气，而赤铁矿/磁铁矿“硬”矿石则不是。后者，但是强烈促进苯酚缩合为二苯并呋喃。新建的实验室级微型烧结设备可以部分或整体令人满意地模仿大规模过程。用实际的进料混合物获得的结果表明，在烧结床中二恶英的形成水平足以说明在现实生活中观察到的大部分产出。通过添加约8 ppm（wt）的氯化物作为NaCl，PCDD / F的产量增加了一倍，但是在氯的施用比例与C2Cl4相同的情况
• PCDD/DF formations by the heterogeneous thermal reactions of phenols and their TiO2 photocatalytic degradation by batch-recycle system
  作者：Hajime Muto、Koki Saitoh、Hitoshi Funayama

  DOI：10.1016/s0045-6535(00)00552-x

  日期：2001.10

  and dibenzofurans (PCDD/DFs) formation by the thermal reactions of phenols with CuCl2 under oxygen flux were carried out in relation to their formation mechanisms. To evaluate the effect of photocatalytic degradation of titanium dioxide (TiO2) thin film prepared by the sol-gel method, the photocatalysis of PCDD/DFs in acetonitrile/water solution by batch-recycle system was conducted. For the thermal reaction

  就酚类与CuCl2在氧通量下的热反应，进行了多氯代二苯并二恶英和二苯并呋喃（PCDD / DFs）的形成机理的研究。为了评价溶胶-凝胶法制备的二氧化钛（TiO2）薄膜的光催化降解效果，采用间歇循环系统对PCDD / DFs在乙腈/水溶液中的光催化性能进行了研究。对于2,4,5-三氯苯酚（2,4,5-TCP）和CuCl2的粉末混合物的热反应系统，总PCDD /的形成速率为8.1 microg / g-2,4,5-TCP / min PCDDs的DFs和6.9 microg / g-2,4,5-TCP / min，与苯酚蒸气/氧气/ CuCl2粉末系统相比，PCDD / DF的总速率高出约40倍。对于2,4,5-TCP的系统，PCDDs主要是通过邻苯氧酚（POP）中间体通过2,4,5-三氯苯酚的缩合反应形成的。对于PCDD / DF光催化降解，大多数PCDD同系物会快速分解，并且在辐照后24小时使用由2
• Emissions of polychlorinated dibenzo-p-dioxins and dibenzofurans from catalytic and thermal oxidizers burning dilute chlorinated vapors
  作者：John R. Hart

  DOI：10.1016/j.chemosphere.2003.10.017

  日期：2004.3

  (ng/dscm)=8.4 exp(-0.0084T degrees C); (2) dioxin/furan production occurs at the combustion catalyst; (3) small variations in temperature cause large changes in the congener distribution of the dioxin and furan isomers; (4) molar TEQ yields from the parent compounds fed to the oxidizers are very small (10(-9)-10(-13)); (5) catalytic and thermal oxidizers may destroy dioxins fed from the ambient air; and (6)

  通过对低（几至几百）百万分之一的氯化和非氯化挥发性有机化合物（VOC）的氧化进行的57次现场测试，发现了多氯二苯并对二恶英和二苯并呋喃（二恶英）的排放。在使用铂，铂/钯或铬（IV）氧化物燃烧催化剂的催化氧化剂中，或在热氧化剂（无催化剂）中发生氧化。催化剂入口温度为293至573摄氏度。热氧化剂的运行温度（火焰后）为773至927摄氏度。报告了有毒的二恶英和呋喃异构体的数据，并进行了加权和表示为国际有毒当量（ 2,3,7,8-四氯二苯并-对-二恶英的TEQ）。最大烟囱排放为1.07 ng / m3 TEQ，发生在293摄氏度。该现场研究的主要结果是：（1）堆中的TEQ水平随工作温度的降低而呈指数增长，经验公式为TEQ（ng / dscm）= 8.4 exp（-0.0084T摄氏度）; （2）在燃烧催化剂处产生二恶英/呋喃；（3）温度的微小变化会导致二恶英和呋喃异构体的同类物分布发生较大变化；
• Emission Factors and Importance of PCDD/Fs, PCBs, PCNs, PAHs and PM₁₀ from the Domestic Burning of Coal and Wood in the U.K.
  作者：Robert G. M. Lee、Peter Coleman、Joanne L. Jones、Kevin C. Jones、Rainer Lohmann

  DOI：10.1021/es048745i

  日期：2005.3.1

  fuels. However, their combined emissions from the domestic burning of coal and wood would contribute only a few percent to annual U.K. emission estimates. Emissions of PAHs and PM10 were major contributors to U.K. national emission inventories. Major emissions were found from the domestic burning for Cl1,2,3DFs, while the contribution of PCDD/F-sigmaTEQ to total U.K. emissions was minor.

  本文介绍了当煤和木材经过受控燃烧实验时针对一系列持久性有机污染物（POPs）得出的排放因子（EFs），旨在模拟空间供暖的家庭燃烧。排放了各种各样的持久性有机污染物，煤炭的排放量高于木材的排放量。对于颗粒物，PM10（大约10 g / kg燃料）和多环芳烃（对于sigmaPAHs大约100 mg / kg燃料）获得了最高的EF。对于氯化物，多氯联苯（PCB）的EF最高，而多氯萘（PCN），二苯并-对-二恶英（PCDD）和二苯并呋喃（PCDF）的丰度较低。对于sigmaPCB，EF大约为1000 ng / kg燃料，对于sigmaPCNs大约为100s ng / kg燃料，对于sigmaPCDD / Fs大约为100 ng / kg燃料。该研究证实，一氯化至三氯化二苯并呋喃Cl1,2,3DFs是低温燃烧过程（如煤炭和木材的国内燃烧）的有力指标。结论是，在固体燃料燃烧期间通常形成许多PCB和PC
• Polychlorinated Dibenzo-<i>p</i>-dioxin/Polychlorinated Dibenzofuran Releases into the Atmosphere from the Use of Secondary Fuels in Cement Kilns during Clinker Formation
  作者：Esteban Abad、Karell MartÍnez、Josep Caixach、Josep Rivera

  DOI：10.1021/es049641a

  日期：2004.9.1

  this study was to evaluate the influence of using waste materials, such as tires or meat meal, as a secondary fuel during clinker production on the polychlorinated dibenzo-p-dioxin (PCDD)/polychlorinated dibenzofuran (PCDF) emission levels to the atmosphere. For this purpose, three different cement plants in Spain were chosen to conduct the project in different sampling episodes. Different materials were

  这项研究的目的是评估在熟料生产过程中使用废料（例如轮胎或肉粉）作为二次燃料对多氯二苯并对二恶英（PCDD）/多氯二苯并呋喃（PCDF）排放水平的影响。大气层。为此，在西班牙选择了三个不同的水泥厂以不同的采样次数进行该项目。每家工厂分别评估了不同的材料：第一家工厂在窑中添加了肉粉，第二家工厂使用了废旧轮胎，第三家工厂使用了两者的混合物。在所有情况下，PCDD / F排放值均保持在欧盟指令规定的0.1 ng I-TEQ / Nm3的限值以下，范围在0.001至0.042 ng I-TEQ / Nm3的范围内。在大多数情况下，对总TEQ的主要贡献来自2,3,7，8-四氯二苯并呋喃的含量较高，而2,3,4,7,8-五氯二苯并呋喃的含量较高，因为其TEF为0.5。其余15种有毒同源物仅对TEQ贡献很小。此外，与使用常规燃料从西班牙水泥窑厂获得的报告数据相比，没有发现显着差异。这一事实表明，添加废轮胎或肉粉对PCDD

表征谱图