化工进展 ›› 2012, Vol. 31 ›› Issue (03): 649-653.

• 精细化工 • 上一篇    下一篇

4,6-二乙氧基间苯二胺的合成

赵德明,张 谭,竺三奇,金宁人   

  1. (浙江工业大学化学工程与材料学院,浙江 杭州 310032)
  • 出版日期:2012-03-05 发布日期:2012-03-05

Synthesis of 4,6-diethoxy phenylenediamine

ZHAO DemingZHANG TanZHU Sanqi JIN Ningren   

  1. (College of Chemical Engineering and Materials Sciences,Zhejiang University of Technology,
    Hangzhou 310032,Zhejiang,China)
  • Online:2012-03-05 Published:2012-03-05

摘要: 以1,5-二氯-2,4-二硝基苯(DCDNB)为原料,经烷氧基化和催化加氢还原反应合成4,6-二乙氧基间苯二胺(DEDAB),并探索了其影响因素。结果表明合成中间体1,5-二乙氧基-2,4-二硝基苯(DEDNB)的较佳条件为:n(DCDNB)∶n(NaOH)∶n(无水C2H5OH)=1∶4∶30,室温下反应7 h,收率96.43%,HPLC纯度99.74%;产品DEDAB的较优合成工艺条件为:n(DEDNB)∶n(无水C2H5OH)= 1∶44,w(10%Pd/C)/w(DEDNB)= 10%,反应时间7 h,反应温度110 ℃,氢气压力1.5 MPa,收率95.42%,HPLC纯度98.87%。产品及中间体结构经1H NMR、MS 和FTIR分析表征确认。

关键词: 1, 5-二氯-2, 4-二硝基苯, 1, 5-二乙氧基-2, 4-二硝基苯, 4, 6-二乙氧基间苯二胺, 烷氧基化反应, 加氢还原反应

Abstract: Through alkoxylation and catalytic hydrogenation reduction reaction,4,6-diethoxy phenylenediamine(DEDAB)was synthesized from 1,5-dichloro-2,4-dinitrobenzene(DCDNB)and the experimental conditions,such as materials ratio,reaction temperature and reaction time,were investigated. Proper experimental condition for alkoxylation reaction were found as:n(1,5-dichloro-2,4-dinitrobenzene)∶n(NaOH)∶n(anhydrous C2H5OH)= 1∶4∶30,room temperature,reaction time 7 h,under which the yield of 1,5-diethoxy-2,4-dinitrobenzene (DEDNB) was 96.43% based on DCDNB and the purity was 99.74% as determined by HPLC;proper catalytic hydrogenation reduction reaction conditions were found as:n(1,5-diethoxy-2,4-dinitrobenzene)∶n(anhydrous C2H5OH)= 1∶44,w(10% Pd/C)∶w(DEDNB)=10%,reaction temperature 110 ℃,reaction time 7 h,pressure of hydrogen 1.5 MPa,under which the yield of DEDAB was 95.42% based on DEDNB and the purity was 98.87% as determined by HPLC. The molecular structures of product and its intermediates were identified by 1H NMR,MS and FTIR.

Key words: 1,5-dichloro-2,4-dinitrobenzene(DCDNB), 1,5-diethoxy-2,4-dinitrobenzene (DEDNB), 4,6-diethoxy phenylene diamine(DEDAB), alkoxylation, catalytic hydrogenation reduction

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