4-氨基-4'-氯二苯甲酮的合成及光谱表征

对硝基苯甲酰氯和氯苯在无水三氯化铝催化下 ,生成 4 硝基 4’ 氯二苯甲酮。以二硫化钠为还原剂 ,将其还原成重要有机中间体 4 氨基 4’ 氯二苯甲酮。通过多因素正交实验 ,确定了最佳工艺条件为 :反应温度 92℃ ,反应时间 2 5h ,4 硝基 4’ 氯二苯甲酮 :Na2 S2 =1∶1 7(mol) ,回收率为 85 80 % ,纯度为98 0 8% ,熔点 177～ 179℃。采用元素分析 ,1H ,13 C核磁共振波谱 ,红外光谱及质谱法表征了目标化合物的分子结构 ,并对化合物红外光谱吸收峰及核磁谱带进行了归属分析。阐明了质谱主要碎片离子的裂解途径。此研究可为无致癌性的禁用染料中间体替代品开发提供依据。

Synthesis and Spectral Characterization of 4-Amino-4'-Chlorobenzophenone

4-nitro-4'-chlorobenzophenone has been synthesized from p-nitrobenzol chloride and chlorobenzene in the presence of catalyst anhydrous AlCl3 and 4-amino-4'-chlorobenzophenone as an important organic intermediate was prepared by reduction of 4-nitro-4'-chlorobenzophenone with Na2S2. With the aid of orthogonal experiments the optimum reaction conditions were determined: reaction temperature 92 degrees C, time 2.5 h, 4-nitro-4'-chlorobenzophenone:Na2S2 = 1:1.7 (mol), yield 85.80%, purity 98.08%, m.p. 177-179 degrees C. The molecular structure of the title compound has been characterized by Elemental Analysis (EA), 1H and 13C Nuclear Magnetic Resonance Spectrometry (NMR), Infrared Spectroscopy (IR), and Mass Spectroscopy (MS), and the main infrared absorption peaks and nuclear magnetic spectral bands of this compound were assigned. The mass spectral fragmentations of the product's important fragment ions were elucidated. The result provides useful information for developing substitutes of non-cancer-causing forbidden dye intermediate.