8-羟基喹啉-5-醛和8-羟基喹啉-5-磺酸联产工艺研究教案分析.docVIP

8-羟基喹啉-5-醛和8-羟基喹啉-5-磺酸联产工艺研究 齐家娟1，2，李树安(2，张珍明1，2，王婷1，2，赵红博1，2 （1.中国矿业大学化工学院，徐州221116；2.淮海工学院江苏省海洋资源开发研究院，连云港222005） 摘要：以8-羟基喹啉为原料，在酸性条件下与水合氯醛发生缩合反应得到5-（α-羟基-β-三氯）-8-羟基喹啉（I），联产8-羟基喹啉-5-磺酸（II）。（I）在碱性条件下水解生成8-羟基喹啉-5-甲醛（III），产物经熔点仪、元素分析仪、液-质联用仪、红外光谱仪及核磁共振氢谱等进行表征。探讨了反应温度、反应时间、原料比、溶剂及溶剂的重复性等因素对实验的影响。确定产物（I）的最佳反应条件为：n（8-羟基喹啉）：n（水合氯醛）：n（硫酸）= 1：1.2：4.6，反应温度为80℃，反应时间为12h，产物收率为55%；产物（III）的最佳反应条件为： n（I）：n（KOH）=1：5.1，回流反应7h，收率为21%。 关键词： 8-羟基喹啉-5-醛；8-羟基喹啉-5-磺酸；8-羟基喹啉；水合氯醛；联产 Study on the process of joint production of 8-hydroxyquinoline-5-carbaldehyde and 8-hydroxyquinoline-5-sulphonic acid QI Jia-juan1,2, LI Shu-an2, ZHANG Zhen-ming1,2, WANG Ting1,2, ZHAO Hong-bo1,2 (1. School of Chemical Engineering Technology, China University of Mining and Technology, Xuzhou 221116; 2.Jiangsu Province R D Institute of Marine Resources, Huaihai Institute of Technology, Lianyungang 222005) Abstract: 5-(α-hydroxy-β-trichloroethyl)-8-hydroxyquinoline (I), 8-hydroxy quinoline-5-sulfonic acid （II） was synthesized by reaction of 8-hydroxyquinoline with chloral hydrate when sulfuric acid was used as solvent. 8-hydroxylquinoline-5-carbaldehyde was synthesized by reaction of (I) with KOH in methanol. The structure of resultant was characterized with melting point detector, elemental analyzer, LC-MS, IR and 1H NMR. The effects of temperature, reaction time, volumes of solvents, material ratio and reusability of solvents on the reaction were studied. The optimum conditions of (I) were found as follows: n(8-hydroxyquinoline) : n(chloral hydrate) : n (H2SO4) =1:1.2:4.6, reaction temperature 80℃, reaction time 12 h, the yield of (I) was 55 %. The optimum conditions of（III）were found as follows: n（I）: n（KOH）=1:5.1, reaction time 7h under reflow, the yield of （III） was 21 %. Keywords: 8-hydroxyquinoline-5-carbaldehyde; 8-hydroxyquinoline-5-sulphonic acid; 8-hydroxyquinoline; Chloral hydrate; joint production 喹啉类化合物是氮杂环中非常重要的一类化合物，许多含喹啉结构的化合物具有抗菌、杀菌、抗病毒等生物活性，其显示了广泛的应用和发展前景。8-羟基喹啉-5-醛和8-羟基喹啉-5-磺酸皆为重要的有机合成中间