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4 - (2,2,2 - Trifluoroethoxy) Study On The Synthesis Of Aniline

Posted on:2008-04-20Degree:MasterType:Thesis
Country:ChinaCandidate:H Y ChenFull Text:PDF
GTID:2191360215498634Subject:Chemical processes
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4-(2,2,2-Trifluoroethoxy)aniline, as one of the most important chemical materials, waswidely applied to medicine, pesticide and dyestuff. 4-(2,2,2-trifluoroethoxy)nitrobenzene wasprepared from 4-chloronitrobenzene and sodium 2, 2, 2-trifluoroethylate throughnucleophilic substitution reaction, and then was hydrogenated by palladium-carbon catalyst toobtain the target product 4-(2,2,2-trifluoroethoxy)nitrobenzene.This dissertation made studies on the effect of internal structure factor and externalenvironment factor. The internal structure factor including: the effect of substituted substratesand leaving groups on trifluoroethoxylation. The external environment factor including: theeffect of reaction temperature, reaction time, material ratio, solvent, and dosage of solvent ontrifluoroethoxylation. Through the research of single factor analysis, the optimized technologywas as follows: N,N-dimethylformamide as solvent, n(4-chloronitrobenzene):n (sodiumtrifluoroethylate) =1:2, temperature 100℃, time 3h. The yield of 4-(2,2,2-trifluoroethoxy)nitro-benzene can be reached 98.5% in a purity of 99.8%. The structure of the product wascharacterized by means of MS.Discuss the effect of pressure, reaction temperature, reaction time, catalyst dosage onhydrogenation and reclamation of palladium-carbon catalyst. Through the research of singlefactor analysis, the optimized technology was as follows: ethanol as solvent, palladium-carboncatalyst, temperature 70℃, time 1h, the yield of 4-(2,2,2-trifluoroethoxy)aniline can bereached 97.0% in a purity of 99.9%. The structure of the product was characterized by meansof ~1H NMR,IR and MS.
Keywords/Search Tags:4-(2,2,2-trifluoroethoxy)aniline, 4-(2,2,2-trifluoroethoxy)-nitrobenzene, 4-chloronitrobenzene, trifluoroethanol, nucleophilic reaction, palladium-carbon catalyst, catalytic hydrogenation
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