摘要
在1,2-二氯乙烷介质中,用混酸将1,5-二氯蒽醌选择性硝化,制备出1,5-二氯-4-硝基蒽醌,后者与过量二乙醇胺进行亲核取代,生成一种含蒽醌发色母体结构的可聚合染料单体:1-(N,N-β-二羟乙基)氨基-5-氯-4-硝基蒽醌。通过单因素实验考察,得到1,5-二氯蒽醌选择性单硝化的较佳工艺条件:使用混酸[n(H2SO4)∶n(HNO3)=2.0∶1.0],投料比n(HNO3)∶n(1,5-二氯蒽醌)=2∶1,反应温度20℃,反应时间4 h,单硝化收率达到95%;在n(二乙醇胺)∶n(1,5-二氯-4-硝基蒽醌)=5∶1,反应温度40℃,反应时间10 h等条件下,目标产物收率达81.5%,最大可见吸收波长(DMF)λmax 1=393.5 nm,λmax 2=514.6 nm。用MS、NMR方法表征了单硝化产物与目标分子的化学结构。
1,5-Dichloroanthraquinone was nitrated with mixed acid in 1,2-dichloroethane to form 1,5- dichloro-4-nitroanthraquinone, which was then subjected to nucleophilic substitution, by which the chlorine atom located opposite the nitro group was displaced with an excess of diethanolamine to give a red polymerizable dye monomer containing anthraquinone： 1-[ N, N-fl-dihydroxyethyl）] amino-5- chloro4-nitroanthraquinone. The optimum process technology of synthesizing 1, 5-dichloro-4- nitroanthra-quinine and 1-[ N, N-fl-di-hydroxyethyl ）] amino-5-chloro-4-nitroanthraquinone was determined via investigating some different factors affecting the synthetic process, by which 1,5- dichloro4-nitroanthraquinone can be obtained in a yield of 95% under the following optimum conditions ： n （ HNO3 ） ： n （1,5-dichloroanthraquinone） = 2：1, mixed acid [ n （ H2 SO4 ） ： n （ HNO3 ） = 2. 0 ： 1.0 ], reaction temperature 20 ~C, and reaction time 4 h. And 1- [ N, N-/3-di-hydroxyethyl ） ] amino-5- chloro-4-nitroanthraquinone can be obtained with A,nax~ = 393. 5 rim, /~max2 ~ 514.6 nm, and in the yield of 81.5% under the following optimum conditions： n （diethanolamine） ： n （ 1,5-dichloro-4- nitroanthraquinone） = 5：1, reaction temperature 40 ~C, and reaction time 10 h. The chemical structures of the two obtained compounds were characterized with MS and NMR.
出处
《精细化工》
EI
CAS
CSCD
北大核心
2014年第4期511-514,共4页
Fine Chemicals
基金
河南省科技攻关项目(122102210046)~~
