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摘要：有机颜料是精细化学品的重要类别，是主要的固体着色剂。偶氮颜料是重要的颜料商业商品。有机颜料的性能与颜料结构中酰胺键的多少、对称性等因素有关。巴比妥酸分子中有多个酰胺键，同时具有活泼氢，可进行偶合反应，将其引入色酚的分子结构中，可以大大提高有机颜料的应用性能和实用价值。本毕业论文根据偶氮化合物的制备原理，以企业提供的巴比妥酸（A）为原料，与对硝基苯胺(B)进行偶合反应、生成对硝基苯偶氮巴比妥酸（C），进而将化合物C通过硫化物还原，得到单偶氮化合物对氨基苯偶氮巴比妥酸（D），化合物D可作为重氮组分与另一分子色酚AS-PH（E）进一步偶合反应，可实现合成多酰胺基、对称性高的双偶氮化合物5-[4-[2-羟基-3-[N-（2-乙氧基苯基）氨基甲酰基]-萘]偶氮苯基]偶氮-2,4,6（1H，3H，5H）嘧啶三酮（F），F与普通颜料相比，在耐光、耐溶剂、稳定性和着色性能方面均有所提高。实验结果表明化合物C制备条件为：（1）重氮化反应最佳条件是pH<1，投料比nHCl ∶nNaNO2∶nB=3.5∶1.2∶1.0，反应温度为10℃，反应时间为40min，（2）偶合反应条件为pH=9，投料比nHCl∶nNaNO2 ∶nB∶nA =3.5∶1.2∶1.0∶1.2，反应温度为10℃，反应时间为50min，收率为91.59%；化合物D的最佳制备条件为：pH= 8，投料比nC ∶nNa2S = 1.0∶1.7，反应温度75℃，反应时间为10h，收率为84.56%；化合物F制备条件为（1）重氮化反应条件是pH<1，投料比nH2SO4 ∶nNaNO2∶nD=1.8∶1.3∶1.0，反应温度为10℃，反应时间为45min，（2）偶合反应条件为pH=7.5~8.5，投料比nH2SO4∶nNaNO2∶nD∶nE=1.8∶1.3∶1.0∶1.0，反应温度为25~30
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℃，反应时间为3h，保温1h，收率为89.20%。用1HNMR、IR、UV谱等对化合物D和F的结构进行了表征。6068
关键词： 对氨基苯偶氮巴比妥酸；双偶氮化合物；重氮化；偶合反应；巴比妥酸；有机颜料
Synthesis and Applied Research of p-Amino-phenylazo barbituric acid
Abstract：The organic pigment is an important category of fine chemicals. It is mainly solid colorant, too. The azo pigment is a important pigment commercial product. Amide bond in the performance and molecules of the organic pigments and symmetry about the amide bond in the molecule. Barbituric acid molecules have more than one amide bond and active hydrogen. It can also happen the coupling reaction which can sever as the introduction of the naphthol structure, and improve many performance and value in use of organic pigments. According to the principle of the preparation of the azo compound, the enterprise offer the barbituric acid(A) as raw material coupling compound p-nitrobene azo barbituric acid(C), compound C the sulfide reduction, and obtain the single azo compound p-aminobenzene azo barbituric acid(D), compound D can be used as diazo component with another molecule of Naphthol AS-PH （E） further reaction, could be prepared by amide quito the high symmetry of double azo compounds—5-[4-[2-hydroxy-3-[N-（2-ethoxyphenyl）aminoacyl]-naphthalenyl ]–azo--phenyl]-azo-2,4,6(1H,3H,5H)-pyrimidinetrilone（F）, compared with ordinary paint pigments, it
improves lightfastness, solvent resistance, and stability. Experimental results show that the compound C preparation conditions: (1) diazotization of pH <1, the feed ratio nHCl :nNaNO2 :nB=3.5:1.1:1.0, the reaction temperature is 10℃, reaction time 40 min, (2) coupling reaction conditions pH =9, the feed ratio nHCl:nNaNO2:nB:nA=3.5:1.1:1.0:1.2, the reaction temperature is 10℃50 min, the yield was 91.59%; The optimal preparation conditions of the compound D as follows: pH =8, the feed ration nC:nNa2S=1.0:1.7, the reaction temperature of 90°C, reaction time 10 h, the yield was 84.56%;compound F preparation conditions: (1) diazotization of pH <1, the feed ratio nHCl∶nNaNO2∶nB=3.5∶1.2∶1.0, the reaction temperature is 10℃, reaction time 45 min, (2) coupling reaction conditions pH =7.5~8.5, the feed ratio nH2SO4∶nNaNO2∶nD∶nE=1.8∶1.3∶1.0∶1.0, the reaction temperature is 25~30℃, reaction time 3 h,Insulation time 1h, the yield was 89.20%. The structure of compounds D and F were characterized by 1HNMR, IR spectroscopy and so on.
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