4,6-二氯二苯并呋喃 | 64560-13-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 4,6-二氯二苯并呋喃
• 英文名称: 4,6-dichlorodibenzofuran
• CAS: 64560-13-0
• 化学式: C₁₂H₆Cl₂O
• 分子量: 237.085
• InChiKey: BZFIZJNKNCJEAD-UHFFFAOYSA-N

物化性质

• 沸点：
  356.4±22.0 °C(Predicted)
• 密度：
  1.442±0.06 g/cm3(Predicted)
• 保留指数：
  1947;1953;1953

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  15
• 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：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1,3-dichloro-2-[(2,6-dichlorophenyl)methyl]-5-methylbenzene 生成 4,6-二氯二苯并呋喃
  参考文献：
  名称：

  FRIEGE, H.;POPPE, A., CHEMOSPHERE, 18,(1989) N-6, C. 1199-1206

  摘要：

  DOI：

文献信息

• Mechanisms of Dioxin Formation from the High-Temperature Oxidation of 2-Chlorophenol
  作者：Catherine S. Evans、Barry Dellinger

  DOI：10.1021/es049355z

  日期：2005.1.1

  are formed at temperatures as low as 400 degrees C. Under oxidative conditions, .OH and Cl. are the major carriers, which favors 4,6-DCDF formation over DD or 1-MCDD through abstraction of H. through diketo- and ether- intermediates. It is proposed that below 500 degrees C, unimolecular tautomerization/HCI elimination and CO elimination/isomerization reactions result in the formation of 1-MCDD and naphthalene

  在 1 cm id、熔融石英流动反应器中研究了 2-氯苯酚的均相气相氧化热降解，浓度为 88 ppm，反应时间为 2.0 秒，温度范围为 300 至 1000 摄氏度。观察到产物按收率排序如下：4,6-二氯二苯并呋喃（4,6-DCDF）>二苯并二恶英（DD）>1-一氯二苯并二恶英（1-MCDD）、4-氯二苯并呋喃（4- MCDF)、二苯并呋喃 (DF)、萘、氯萘、2,4-二氯苯酚、2,6-二氯苯酚、苯酚、氯苯和苯。与热解相反，4,6-DCDF 是主要产物，而不是 DD，1-MCDD 和萘在低至 400 摄氏度的温度下形成。在氧化条件下，.OH 和 Cl。是主要的载体，通过 H. 通过二酮和醚中间体。建议在 500 摄氏度以下，单分子互变异构化/HCl 消除和 CO 消除/异构化反应分别导致 1-MCDD 和萘的形成。
• A Detailed Mechanism of the Surface-Mediated Formation of PCDD/F from the Oxidation of 2-Chlorophenol on a CuO/Silica Surface
  作者：Slawomir Lomnicki、Barry Dellinger

  DOI：10.1021/jp026045z

  日期：2003.6.1

  The formation of polychlorinated dibenzo-p-dioxins and dibenzofurans (PCDD/F) via a Cu(II)O-mediated reaction of 2-chlorophenol (2-MCP) has been studied in a packed bed reactor over a temperature range of 200-500 degreesC. Under oxidative conditions, the principle PCDD/F products were 1-monochlorodibenzo-p-dioxin (MCDD) > 4,6-dichlorodibenzofuran (DCDF) > dibenzo-p-dioxin (DD). EPR studies indicated the presence of a carbon-centered phenoxyl radical on the surface, which is attributed to chemisorption of 2-MCP at a copper oxide site followed by electron transfer to Cu(II) to form Cu(I) and a phenoxyl radical. The presence of a surface bound phenoxyl radical and the formation of MCDD, DCDF, and DD, which were also observed as the principle products of the gas-phase oxidation of 2-MCP, strongly suggest a surface-mediated mechanism involving many of the same radical and molecular species involved in the gas-phase formation of PCDD/F from 2-MCP. Reaction orders of 0.5-1.0 were observed for MCDD and DD formation, indicating an Eley-Rideal formation mechanism. Negative reaction orders were observed for DCDF formation, indicating a Langmuir-Hinshelwood formation mechanism. No highly chlorinated PCDFs were observed, suggesting a mechanism in which DCDF is desorbed from the surface before it can undergo additional chlorination. Highly chlorinated PCDDs were observed, which were consistent with a mechanism in which DD remained adsorbed to the surface and underwent additional chlorination. Chloro-o-quinone and chlorocatechol, which are precursors to semiquinone radicals, were also observed products. A detailed reaction mechanism accounting for all reported products is proposed.