4-硝基苯基马来酰亚胺的合成研究

Study on the Synthesis of 4-Nitrophenyl Maleimide

以顺丁烯二酸酐和对硝基苯胺为原料,甲苯和DMF混合溶液作溶剂,对甲基苯磺酸和硫酸铜为催化剂,采用两步法合成了4-硝基苯基马来酰亚胺,用红外光谱和核磁共振氢谱对产物进行了表征;同时研究了反应物物质的量比、催化剂用量以及混合溶剂配比等因素对合成4-硝基苯基马来酰亚胺的影响。得到的最佳工艺条件是:n(顺丁烯二酸酐)∶n(对硝基苯胺)为1.2∶1,V(甲苯)∶V(DMF)为10∶1;胺化反应温度为20～30℃,环化反应温度为140～150℃,环化反应时间为6h以上;对甲基苯磺酸用量为反应物总质量的1%～2%;硫酸铜用量为反应物总质量的0.1%～0.5%;对苯二酚用量为反应物总质量的0.1%。在此条件下,产物收率达到85%以上,纯度达到98.1%。

4 - Nitrophenyl maleimide was synthesized with two-step method from maleic anhydride and pnitroaniline in the presence of toluene and DMF component solvent, with p-toluene sulfonic acid and copper （Ⅱ ） sulfate as catalysts. The synthesized 4 - nitrophenyl maleimide were characterized by fourier transform infrared spectrometer （FFIR） and ^1HNMR. And the affecting factors of the synthesis of 4 - nitrophenyl maleimide were studied, such as mole number ratio of reactants, catalyst amount and volume ratio of solvents. The optimum reaction conditions were that the molar ratio of maleic anhydride and p-nitroaniline was 1.2： 1, the volume ratio of toluene and DMF was 10： 1, the amination temperature was 20 - 30℃, the cyelization temperature was 145 - 150℃ and the cyclization time was 6 h over; the amount of p-toluene sulfonic acid was 1 -2% of total reactant mass, the amount of copper （ Ⅱ ） sulfate was 0. 1 -0.5% of total reactant mass, the amount of hydroquinol was 0. 1% of total reactant mass. The yield of product was up to 85% and the purity was about 98. 1%.