4-N,N-二丁氨基-2-羟基-2′-羧基二苯酮合成方法的研究

Synthesis of 2-(4-(Dibutylamino)-2- Hydroxybenzoyl) Benzoic Acid

以间氨基苯酚、碘丁烷为初始原料 ,在溶剂及脱酸剂的存在下 ,于常压下加热回流制备间二丁氨基苯酚 ,再与苯酐缩合成 4 N ,N 二丁氨基 2 羟基 2’ 羧基二苯酮的合成路线 ,产品总收率达 78% ,主含量≥ 99% .该产品与二芳胺或萘胺发生缩合反应形成具有内酯环的无色多芳基荧烷类化合物 ,该系列化合物与酚类化合物在热、压的条件下 ,可发生开环反应而显黑、红、蓝、绿等色彩 .与用氯丁烷为原料的合成路线相比 ,方法虽然原料较贵但避免高温和高压反应 。

A synthetic method of 2-(4-N,N- dibutyl amino-2-hydroxybenzoyl) benzoic acid was described. The intermediate product 2-(4-N,N- dibutyl amino) phenol was prepared by the reaction of 2-amino-phenol and n-butyl iodide in the presence of solvent and sodium carbonate at 1 atm and 90 ℃, and then was condensed with phthalic anhydride. The total yield is more than 78% and the content of the product is 99%. The prepared product can react with diaryl amino or naphthylamino to form leuco multiaryl fluoran compounds containing lactone, which exhibit different colors, such as black, red, blue and green, by ring opening in the presence of phenols under heat and pressure. In this paper the infection facts on reaction of preparing 2-(4-N,N- dibutyl amino) phenol were discussed in detail, and the facts invole raw materials ratio, reaction time and temperture. And the best reaction condition has formed through homogeneous design experiment project with computer, that is, 2-amino-pheno:n-tubyl iodide: sodium carbonate(mol-ratio)=1∶2.44∶1.08; the best reaction time is 6 hours and the best reaction temperture is (90±2) ℃. The yield of this reaction is 96.5%. The feasibility that different halides reacted to produce 2-(4-N,N- dibutyl amino) phenol under the normal pressure was discussed as well. The experiment results indicated that only n-tubyl iodide can successfully react with 2-amino-phenol to successfully form 2-(4-N,N- dibutyl amino) phenol under the refluence temperture and normal pressure. Compared with the method based on n-butyl chloride although the price of raw material n-butyl iodide is more expensive, this prepared route avoids reacting under high pressure and temperature. It seems to be easier for industrialization in China. The homogeneous design project was also applied to producing 2-(4-N,N- dibutyl amino-2-hydroxybenzoyl) benzoic acid. The best reaction condition is. 2-(4-N, N- dibutyl amino) phenol: Phthalic anhydride (Mol ratio)= 1∶1.5; reaction temperture is 105～110 ℃; reaction period is 10～14 hours. The purity of product is 99.8% and the yield is more than 80%.