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Of polychlorinated polycyclic aromatic compounds solvothermal synthesis , isolation and characterization

Author: PengYin
Tutor: ZhengLanZuo；HuangRongBin
School: Xiamen University
Course: Inorganic Chemistry
Keywords: Polycyclic aromatic compounds Solvothermal synthesis Solvothermal Perchlorinated Carbon tetrachloride Polychlorinated aromatic compounds Synthetic product Sodium metal Chlorine compounds Chlorine radicals
CLC: O625
Type: PhD thesis
Year: 2003
Downloads: 119
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Abstract

Polychlorinated aromatic compounds as aromatic compounds member of the family, it has great significance in research in the field of molecular recognition, the study of the carbon cage-ion, fullerenes. Chlorinated aromatic compounds synthesis of history, dating back a hundred years ago Beilstein work of the research team, the first time they design the synthesis of chlorinated aromatic compounds. Since then, different research groups engaged in research in this area, but unfortunately the results are unsatisfactory. The difficulties faced in the introduction of the last one chlorine steric shielding effect and the loss of electrochemical activity. Thus, suitable synthetic chlorinated aromatic compound is successfully obtained. Many halogenated alkane, such as: carbon tetrachloride, chloroform, etc. with an alkali metal mixed the organic solubilizing chain reaction (Wurtz reaction), but prone to violent explosion, so this kind of reaction rarely been applied in conventional organic synthesis. However, it was recently reported in the literature, if such a reaction is carried out in a closed system (solvothermal conditions) in the explosive reaction can be avoided. Moreover, such reactions have been used for the synthesis of a variety of carbon-rich material, such as diamond, nanotubes, graphite, nano-onions. This shows that in the solvothermal conditions, carbon tetrachloride, and other small molecules can be synthesized by the Wurtz reaction of carbon-rich substance having a different structure, and instead of the chain extension reaction is a simple alkyl group, such as under the open system. But whether it is a diamond or carbon nanomaterials synthesis of the focus is a the inorganic solid product. Then, if the control of the reaction conditions, such as carbon tetrachloride chlorine atom in the carbon chlorine compounds in the small molecule is not completely take off, according to the the Wurtz reaction mechanism will produce large amounts of carbon chlorine radical or carbonium ion in the reaction system, they under solvothermal conditions in accordance with the growth pattern of the combination will generate a lot of polychlorinated polycyclic aromatic compounds. Thus, small molecular carbon chloro compound and an alkali metal as a raw material, under the conditions of a solvothermal synthesis of polychlorinated polycyclic aromatic compound is likely to. Carbon tetrachloride and carbon chlorine compounds successfully synthesized under solvothermal conditions such as diamond carbon elemental of great theoretical and application value, fully embodies the solvothermal method has the advantage. Solvothermal synthesis' dissertation">Solvothermal synthesis method of characteristics, advantages, and its value in the field of inorganic chemical synthesis has been fully demonstrated, but the application of this method in the field of organic chemistry synthesis has not been reported. Solvothermal synthesis of polycyclic aromatic compounds polychlorinated has some theoretical and practical significance In this paper, carbon tetrachloride and sodium metal as raw material, synthesized under solvothermal conditions of polychlorinated polycyclic aromatic compounds , Isolation and Characterization of the synthetic product, and discussion According to the experimental results under solvothermal conditions carbocyclic growth. Summary 1, by the reaction temperature, reaction time, used in an amount of sodium metal exploration optimization solvothermal reaction conditions: 3.09 (o.13mox) of Na in 25 ml of eel4 Add to the volume of the stainless 4oml reactor, in 300Oe temperature of the reaction for 40 hours. 2, by means of high performance liquid chromatography-mass spectrometry UV spectrum associated with the methanol-cyclohexane as the mobile phase gradient reversed-phase C18 column successfully achieved more than 50 kinds of polychlorinated separation and analysis of polycyclic aromatic compounds. Based on mass spectrometry characteristics of of polychlorinated polycyclic aromatic compounds and chlorine isotope mass distribution characteristics, to determine the basic formula of these synthetic products. By sublimation the ordinary neutral alumina column chromatography, recrystallization, preparative high-performance liquid chromatography and other separation means, to obtain 16 kinds of pure polychlorinated polycyclic aromatic compound, and to create conditions for its further structural analysis and characterization. 3, through the repeated attempts to establish a the solvothermal synthesis product by preparative high-performance liquid chromatography separation and purification methods. Toluene and methanol as the mobile phase in reversed-phase C18 preparative column succeeded in achieving a variety of polychlorinated polycyclic aromatic compounds preparative separation and purification. By X-ray diffraction, infrared spectroscopy, ultraviolet spectrum, mass spectrometry, NMR and other characterization methods from the 16 pure compounds C6C16 C oci: ClzCll. The, C 3ClsO C15Clso, (C 6Cllo) ZCsZ, e,: C a, 202 e, gel: OHZ, e,, e GOH C24e a 2 e25el. The 02 C26C17OHS (two with the same score isomers), C26ClsOZHZ C26CI. The H: C39Cll. Structural analysis, identified by the 12 kinds of compounds as a novel compound and For the first time the novel compounds C a ClSO (C16Cll): CS: C! SC a 120: C19elgOH e26elsoZHZ C26CI. The crystal structure of Hs. 5, experimental results, combined with the Wurtz reaction mechanism, on the the solvothermal conditions carbocyclic growth mechanism are discussed as follows: sodium metal and carbon tetrachloride is sealed in a stainless steel reactor, under high temperature and pressure, carbon tetrachloride in the metallic sodium the role of, disconnect c cI key, the formation of the carbon chlorine free radicals or carbenium ion, such as: CC12, CC13, CC13 10. Through a multi-step Wurtz reaction, these free radicals or ions restructuring, according to a certain growth pattern of different growth path toward of various carbon elemental (diamond, graphite, fullerenes) the direction of growth. Initially generated in the reaction carbocyclic ring having a strong chemical activity, the dangling bonds of the peripheral carbon atoms of the carbon skeleton ring continuously saturated by free radicals (generated during the reaction, such as a chlorine atom, an oxygen atom or a hydrogen atom), In multi-chlorinated polycyclic aromatic compound in the form of stabilized, thereby preventing these carbocyclic toward different carbon elemental growth. Further shows structure of the polycyclic aromatic compound from the resulting polychlorinated them with three carbon single mass there is a certain correlation between structure, which indicates that three carbon elemental After these polychlorinated polycyclic aromatic compound growth. Abstract solvothermal synthesis of aromatic compounds and other oxo synthesis method compared to the simple, easy, step synthesis features. Synthetic products more abundant, solve the problem of the conventional method of synthesis of chlorinated compounds difficult. The method has demonstrated promising application prospect, but this is only a preliminary study, a lot of meaningful work remains to be further attempts. Although the the solvothermal synthesis product is more abundant, but only obtained more than 16 kinds of atmosphere on behalf of polycyclic aromatic compounds, macro points?

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