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Study on the Friedel-Crafts Reaction between Trichloroacetyl Chloride and Arylcompounds and the Preparation of Azo Inducing Reagents by Hydrogen Peroxide Oxidation

Posted on:2004-08-09Degree:MasterType:Thesis
Country:ChinaCandidate:C B WangFull Text:PDF
GTID:2191360092493697Subject:Organic Chemistry
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This dissertation consists two parts:Part One: The Friedel-Crafts reaction between trichloroacetyl chloride and arylcompounds has been discussed. First, seven a , a , a -trichlorlarylacetones have been synthesized through the' reaction between trichloroacetyl chloride and benzene, toluene, ethylbenzene, chlorobenzene, o-dichlorobenzene, o-dimethylbenzene, m-dimethylbenzene, biphenyl ( , , -trichlorl-4-ethylbenzenethanone has not been synthesized, so the residual continued to react with alkali after separating the solvent). Seven arylacetamides were produced by the reaction of the -trichlorlarylacetone and NH3. The p-chlorobenzamide was selected to prepare the p-chlorobenzcyanide by the dehydration reaction. Six -trichloroarylacetones reacted with the aqueous solution of the base, then adjusted the pH of the mixture by adding the acid and finally got the respective arylacids. Second, the reactions of trichloroacetyl chloride and two phenols(biphenol and p-methylphenol) were discussed. The two substituted phenols were prepared and used to the successive reactions of the aminolysis to produce the hydroxylarylamines. The dehydration reaction of 4' -hydroxyl -4-biphenylacetamide was conducted to get the 4 ' -hydroxylbiphenyl -4-carbonitril. The two substituted trichloroacetyl phenols were used to the reaction of the basic hydrolysis to produce the hydroxylarylacids. At last the structures of the compounds were tested by IR, 1HNMR, UV and element analysis.The series of reactions introduced the trichloroacetyl to the arylide by the Friedel-Crafts reaction between the trichloroacetyl chloride and the arylide. The -CCl3 group of the trichloroacetyl was inclined to the aminolysis and the basic hydrolysis reaction to produce the arylcarboxylic acid and the arylamide. The arylamide was dehydrated to get the arylcyanide. We found an easy and convenient way to introduce the carboxyl and cyano.Part Two: In this part the emphasis was put on the research of a new method to synthesize the azo inducing reagents by the oxydation of H2O2. Theazodiisobutyronitrile and the azodiisoheptronitrile were most widely used among them, Both could be synthesized by two-step method: The 2-cyano-2-propanol reacted with the hydrazine hydrate in the aqueous solution to synthesize diisobutyronitrile hydrazine and the resulted diisobutyronitrile hydrazine was oxidized to the azodiisobutyronitrile by H2O2 with the bromide as the catalyst. The methylisoacetone, hydrazine hydrate and hydrogen cyanide or sodium cyanide mixed together and directly synthesized the diisoheptronitrile hydrazine under a certain condition. The resulted diisoheptronitrile hydrazine was oxidized to the azodiisoheptronitrile by H2O2 with the bromide as the catalyst. The oxidative method by H2O2 exhibited several advantages in the preparation of azo compounds: the filtrated stock could be recycled, the less pollution to the environment was caused and at the same time the rate of production of this reaction was raised in this way. The significant improvement of this synthesis process was that the cyanide hydrazine was oxidized completely by H2O2, which made the reaction condition moderate, made the amouht of material easily controlled, reduced the pollution to the environment and greatly enhanced the rate of production.
Keywords/Search Tags:the Friedel-Crafts, Reaction, Trichloroacetyl chloride alkaline bydrolysis, Aminolysis, Hydrogen peroxide, Oxidation, AxobisIsoButyroNitrile, AxobisdimethylValeroNitrile
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