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The Systhesis Of The Whole Flouorinated Aromatic Diamine

Posted on:2007-03-26Degree:MasterType:Thesis
Country:ChinaCandidate:D TanFull Text:PDF
GTID:2121360185980763Subject:Organic Chemistry
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The whole fluorinated polyimide is a kind of high capable material that has extraordinary and potential development, and the whole fluorinated aromatic diamine is the most important monomer to synthesize it. A series of the whole fluorinated aromatic were synthesized in this paper. The final materials(target products) such as 2,4,5,6-tetrafluoro-1,3-benzenediamine; 2,3,5,6- tetrafluoro-1,4-benzenediamine; octafluoro-biphenyl-4,4'-diamine and pentafluoroaniline were designed and synthesized.The synthesis route of 2,4,5,6- tetrafluoro-1,3-benzenediamine was described: The raw stuff 2,4,5,6-tetrafluorophthalonitrile was fluorinated by potassium fluoride and hydrolated to obtain the2,4,5,6- tetrafluorobenzene-1,3-diamide, then a Hofmann reaction was reacted(carried out) to get the final product 2,4,5,6-tetrafluoro benzene-1,3-diamine. So was the pentafluoroaniline synthesis(synthesized). 2,3,5,6-Tetrachlorobenzen-1,4-dioic acid was prepared from terephthalic acid by chlorinating, using oleum as solvent and iodine as catalyst, then acylated by sulfuryl chloride in the presence of DMF to obtain 2,3,5,6- tetrachlorobenzene-1,4-dioyl dichloride, which was fluorinated by potassium fluoride and reacted with the ammonia to get 2,3,5,6- tetrafluorobenzene-1,4-diamide.The final product 2,3,5,6-tetrafluoro benzene-1,4-diamine was obtained after the Hofmann reaction. Biphenyl-4,4'-dicarboxylic acid was oxidated from 4,4'-bis(chloro methyl)-1,1'-biphenyl, then chlorinated, acylated, fluorinated and Hofmann rearranged to get the final product 2,2',3,3',5,5',6,6'-octafluoro -biphenyl-4,4'-diamine.The synthesis of benzoic acid from benzyl chloride by potassium permanganate(KMnO 4 ) oxidation in the presence of phase transfer catalyst -quaternary ammonium salt(CTAB) was primarily researched.The influence of the amount of CTAB and KMnO 4 , the time and temperature of the reaction on the yield of benzoic acid were investigated. The influenced factors of the chlorination reaction and the go-work methods of the acylchlorination reaction, especially the influenced factors of fluorination reaction condition such as solvent, reaction temperature and phase-transfer catalysts were deeply researched and the optimum condition of the fluorination reaction was determined. The prominent contents of our...
Keywords/Search Tags:Pentafluoroaniline, 2,4,5,6-Tetrafluorobenzene-1,3-diamine, 2,3,5,6-Tetrafluorobenzene-1,4-diamine, 2,2',3,3',5,5',6,6'-Octafluorobiphenyl-4,4'-diamine, Tetrafluorobenzene-1,4-diamide, Hoffman rearrangement
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