2,3,4,6,9-pentachlorodibenzofuran | 83704-35-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2,3,4,6,9-pentachlorodibenzofuran
• 英文别名: 1,4,6,7,8-pentachlorodibenzofuran；2,3,4,6,9-PCDF；2,3,4,6,9-P₅CDF；PeCDF 14678
• CAS: 83704-35-2
• 化学式: C₁₂H₃Cl₅O
• 分子量: 340.42
• InChiKey: VANGHZRYKXDPRR-UHFFFAOYSA-N

物化性质

• 保留指数：
  2482;2511;2476;2476

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  18
• 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

• 作为反应物：
  描述：

  2,3,4,6,9-pentachlorodibenzofuran 以 正己烷 为溶剂， 反应 4.0h， 生成 1,2,7,8-四氯二苯并呋喃 、 1,4,6,8-四氯二苯并呋喃 、 1,4,6,7-四氯二苯并呋喃 、 1,4,7,8-四氯二苯并呋喃
  参考文献：
  名称：

  Synthesis of the 38 tetrachlorodibenzofuran isomers and identification by capillary column gas chromatography mass spectrometry

  摘要：

  DOI：

  10.1021/ac00252a028
• 作为产物：
  描述：

  晕苯 在 copper(l) chloride 氧气 、 甲烷 作用下， 反应 2.0h， 生成 2,3,4,6,9-pentachlorodibenzofuran
  参考文献：
  名称：

  De Novo Synthesis Mechanism of Polychlorinated Dibenzofurans from Polycyclic Aromatic Hydrocarbons and the Characteristic Isomers of Polychlorinated Naphthalenes

  摘要：

  Polychlorinated dibenzofurans (PCDFs) and polychlorinated naphthalenes (PCNs) are known to be emitted from municipal waste incinerators (MWIs) with polychlorinated dibenzo-p-dioxins (PCDDs). Two formation paths for PCDD/Fs could mainly work, which are condensation of the precursors such as chlorophenols and "de novo" formation from carbon. However the correlation between the chemical structure of carbon and the resulting PCDD/Fs still remains unknown. In this study, the PCDD/Fs formation from polycyclic aromatic hydrocarbons (PAHs) and CuCl was examined at 400 under 10% O-2. Coronene among the PAHs characteristically gave 1,2,8,9-T4CDF and the derivatives. These isomers clearly indicate that chlorination causes the cleavage of the C-C bonds in a coronene molecule and also that oxygen is easily incorporated from its outside to form 1,2,8,9-T4CDF. The symmetrical preformed structures in the coronene molecule enabled to amplify the de novo formation of the isomer. PCNs are also formed directly from these PAHs. Since there have been few reports on the formation mechanism of PCNs, this study will be a first step to know the whole formation paths. We also define the de novo synthesis as the breakdown reaction of a carbon matrix, since the word has been used without the precise definition.

  DOI：

  10.1021/es980857k

文献信息

• Isomer Distributions of Polychlorinated Dibenzo-<i>p</i>-dioxins/Dibenzofurans Formed during De Novo Synthesis on Incinerator Fly Ash
  作者：Ruud Addink、Harrie A. J. Govers、Kees Olie

  DOI：10.1021/es971077z

  日期：1998.7.1

  Polychlorinated dibenzo-p-dioxins (PCDD) and dibenzofurans (PCDF) emitted from municipal waste incinerators appear to have a chlorination pattern that is quite constant across various samples and conditions. This suggested that these patterns may he controlled by thermodynamic properties of the individual PCDD/F congeners, such as the free Gibbs energy of formation (Delta G degrees(f,T)) This would make prediction of the isomer composition of a particular sample (and hence its TEQ value) possible, based on values of Delta G degrees(f.T). A laboratory scale study was carried out with activated carbon on fly ash as the source of PCDD/F formation. Although it was found that the isomer distributions within homologues were independent of the reaction time (proof of thermodynamic control), other observations (lack of equilibrium/isomerization between isomers and lack of similarity between isomer distributions measured and predicted by Delta G degrees(f,T)) contradicted the possibility of thermodynamic control. Hence, this study could not confirm that de novo formation of PCDD/F could explain thermodynamically controlled isomer distributions in incinerators. Some recommendations for further work-time-based studies with precursors, isomerization studies with single congeners, and more data on Delta G degrees(f,T) values of PCDD/F-were made.