硫杂蒽酮的合成和表征

摘要

In pursuit of novel highly efficient methods for synthesizing thioxanthone, efforts were made to investigate the effects of molecular sieve zeolite, A12O3 and P2O5, temperature, mass ratio of raw materials, and reaction time on yield of thioxanthone with 2,2'-dithiodibenzo-ic acid and phenol as the starting materials and sulfuric acid as the solvent and catalyst. The optimal reaction condition was established, and possible reaction pathways were discussed. Moreover, 13 thioxanthone compounds were prepared from 2,2 -dithiodibenzoic acid and benzene derivatives under the optimal reaction condition in the presence of H2SO4-P2O5. All as-synthesized compounds were separated by column chromatography and characterized by infrared spectrometry and nuclear magnetic resonance spectroscopy. Results indicate that introducing P2O5 into reaction system helps to accelerate the synthetic reaction. The optimal reaction condition is suggested as temperature of 70 ℃, raw materials (dithiodibenzoic acid and benzene derivative) mass ratio of 1 : 6, and reaction time of 6 h. The corresponding reaction productsrnof 2,2 -dithiodibenzoic acid and o-dihydroxyl benzene--compounds 11 (a) and 1Kb) are iso-mers.%为了寻求合成硫杂蒽酮的高效新方法,以2,2'-二硫代二苯甲酸和苯酚为原料,硫酸为溶剂和催化剂,考察了沸石分子筛、Al2O3和P2O5、温度、原料的物质的量之比、反应时间对反应收率的影响,确定了最佳反应条件,推测了可能的反应过程；进而以2,2'二硫代二苯甲酸和相应的苯衍生物为原料,在H2SO4-P2O5体系中于最佳反应条件下制备了13个硫杂蒽酮类化合物,并利用柱色谱分离以及红外光谱与核磁共振谱对产物进行表征.结果表明,在反应体系中引入P2O5有利于促进反应的完成；最佳反应条件为:温度70℃、2,2 '-二硫代二苯甲酸/苯衍生物物质的量之比1∶6、反应时间6h.邻苯二酚与二硫代水杨酸的反应产物——化合物11(a)和11(b)为同分异构体.