三氟化硼催化合成2,3,4,4'-四羟基二苯甲酮新方法研究  

A New Synthetic Method of 2,3,4,4'-Tetrahydroxybenzophenone by Boron Trifluoride Catalysis

作　　者：欧阳文[1] 曹庸[2] 陈雪香[2] 杜方麓[1] 

机构地区：[1]湖南中医药大学药学院,湖南长沙410208 [2]华南农业大学食品学院,广东广州510642

出　　处：《林产化学与工业》2014年第4期21-24,共4页Chemistry and Industry of Forest Products

基　　金：'十二五'国家科技支撑计划资助项目(2012BAK17B08);湖南省'中药学'重点学科建设项目(湘教通[2011]76号);湖南中医药大学'十二五'药物分析学校级重点学科资助项目(无编号)

摘　　要：以高沸程石油醚代替1,1,2,2-四氯乙烷为溶剂,对焦性没食子酸合成2,3,4,4'-四羟基二苯甲酮的经典方法——三氟化硼催化法进行改进。在常温下快速搅拌和加热,使原料和溶剂体系由混悬液转变成棕色油状溶液,一定时间后瞬间产生大量黄色油性结晶产物沉淀,完成合成反应。采用正交试验法优化反应条件为:焦性没食子酸0.05 mol、对羟基苯甲酸用量0.055 mol、催化剂用量0.16 mol(20 mL)、反应温度110℃、反应时间1 h,在此条件下,2,3,4,4'-四羟基二苯甲酮产率达83.24%,产品纯度为97.83%。该方法与传统方法的产率相近,生产过程中比1,1,2,2-四氯乙烷的毒性小、成本低,改进的合成反应还具有时间短、后处理简便、催化剂可回收等优点。对提纯到99.53%的产物,通过红外吸收光谱、核磁共振谱、质谱等方法进行鉴定和表征,确定了产物为2,3,4,4'-四羟基二苯甲酮。A new synthesis of 2,3,4,4＇-tetrahydroxybenzophenone by boron trifluoride etherate catalysis was proposed in this paper. In the new method, high boiling-point petroleum ether was used as the reaction solvent to replace the poisonous and expensive 1,1,2,2-tetrachloroethane. Although p-hydroxybenzoic acid, pyrogallic acid, boron trifluoride and petroleum ether were immiscible at room temperature, the reaction system could be gradually turned into brown oily solution in the heating and rapid mixing conditions. After a period of time, a large amount of yellow crystalline products were precipitated. According to the results of orthogonal experiments, the optimum reaction conditions were as follows ： pyrogallic acid 0.05 mol, p-hydroxybenzoic acid 0. 055 mol, catalyst 0.16 mol （20 mL）, reaction temperature 110 ℃ and reaction time 1 h. Under this condition, the yield reached 83.24% and product purity 97.83 %. The new method possessed many advantages, e. g. , low toxicity, low cost, short reaction time, easy operation and the recycled catalyst. The product with 99.53% purity by recrystallization in water was identified as 2,3,4,4＇-tetrahydroxybenzophenone by the combination of IR, NMR and El-MS techniques.

关 键 词：焦性没食子酸 2 3 4 4’-四羟基二苯甲酮 高沸程石油醚 三氟化硼 

分 类 号：TQ35[化学工程]