4,4′-二氨基苯磺酰苯胺的合成

该文对4,4′-二氨基苯磺酰苯胺(Ⅰ)的合成进行了研究。对硝基苯胺在90~95℃的水中用铁粉还原为对苯二胺,收率约90%;乙酰苯胺与氯磺酸〔n(乙酰苯胺)∶n(氯磺酸)=1∶4〕在60~65℃及氨基磺酸催化下,反应3 h生成对乙酰氨基苯磺酰氯,收率85%;乙酰氨基苯磺酰氯与对苯二胺在四丁基溴化胺催化下,于30~35℃反应12 h,生成4-乙酰氨基-4′-氨基苯磺酰苯胺;最后在95℃用氢氧化钠水解,得到4,4′-二氨基苯磺酰苯胺。高效液相色谱测得w(Ⅰ)>98.5%,总收率约75%。该路线生产成本比协作单位已有的生产工艺节省10%,已成功用于年产150 tⅠ的工业生产中。

Synthesis of 4,4′-Diaminobenzenesulfonanilide

4-Nitroaniline was reduced by Fe powder at 90～95 ℃ in water to afford 1,4-diaminobenzene in 90% yield.Acetanilide and chlorosulfonic acid(n(acetanilide)∶n(chlorosulfonic acid)=1∶4)reacted for 3 h at 60～65 ℃ in the presence of aminosulfonic acid to give 4-acetamidobenzenesulfonyl chloride in 85% yield.Then 4-acetamidobenzenesulfonyl chloride was treated with 1,4-diaminobenzene catalyzed by tetrabutylammonium bromide for 12 h at 30～35 ℃ to get 4-acetamino-4′-aminobenzenesulfonanilide,which was hydrolyzed at 95 ℃ by sodium hydroxide to give 4,4′-diaminobenzensulfonanilide.The total yield is 75% and the purity of product is higher than 98.5%.This synthesis route reduced the cost by 10%,and has been applied in the production on scale of 150 t/a successfully.