| Organic dye and pigment industry is an important branch of chemical industry.Organic dye, especially organic pigment, is widely applied in our daily lives andindustry production. And,2-nitroaniline is an important chemical material, which canbe used to prepare kinds of intermediates of dyes and pigments.Three compounds of2-nitroaniline derivatives were synthesized in this thesis,including4-amino-3-nitrobenzenesulfonic acid, N-(2-nitrophenyl)-3-oxobutanamide,5-acetylacetamidobenzimidazolone.The production process of4-amino-3-nitrobenzenesulfonic acid has beenimproved and optimized. The reaction conditions are as follows. Concentratedsulfuric acid is used as sulfonating agent; the mixture of chlorobenzene anddichlorobenzene is used as reaction solvent; dehydration unit is introduced to thereaction equipment. The yield of the product can reach99%, and the purity can reach98%.What’s more, acetoacetylation of2-nitroaniline has been studied. The optimumreaction conditions are as follows: diketene is used as acylating agent, andtriethylamine is applied as catalyst and acetic acid is as solvent; reaction temperatureis55～60℃. With diluted sedimentation, light yellow product can be gained, withyield of70.1%.Based on the study of acetoacetylation of2-nitroaniline, the acetoacetylationprocess of5-aminobenzimidazolone has been studied, too. Diketene is acylating agent,and acetonitrile, dichloromethane, ethyl acetate, ethyl acetoacetate, toluene,triethylamine, tetrahydrofuran, methanol, ethanol, acetic acid and N,N-dimethylformamide are used as reaction solvent respectively. Triethylamine andtetramethylethylenediamine are used as catalyst. In organic reaction medium, theyield of5-acetylacetamidobenzimidazolone can reach89.3%. |
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