李 敬,张学良,郝双红,孙家隆

(青岛农业大学化学与药学院,山东青岛 266109）

1,6-二氯二苯并-对-二噁英的合成与表征

李 敬,张学良,郝双红,孙家隆＊

(青岛农业大学化学与药学院,山东青岛 266109）

二噁英是一类毒性极大的特殊脂溶性有机化合物,严重污染环境和危害人类健康.1,6-二氯二苯并-对-二噁英是一种二噁英的前驱体,常作为杂质存在于某些农药产品中,在农药使用前需检测其含量.为此,采用磺酰氯氯化邻苯二酚得到中间产物4-氯邻苯二酚,再将中间产物与2,6-二氯硝基苯反应得到1,6-二氯二苯并-对-二噁英.利用高效液相色谱分析了产物的纯度,并通过气相色谱、核磁共振谱(1H NMR和13C NMR)对合成的目标物进行了表征.结果表明,目标产物柱层析品的纯度为99.76%.

二噁英;1,6-二氯二苯并-对-二噁英;合成;表征

Abstract:As a kind of special fat-soluble organic compounds with high toxicity,dioxin is severely harmful to environment and human health.Besides,1,6-dichloro-dibenzyl para-dioxin as a precursor of dioxin often exists in some pesticides,and its content in pesticides usually needs to be monitored before putting into use.Thus pyrocatechol was chlorinated with sulfonyl chloride yielding intermediate 4-chloro-pyrocatechol;then 4-chloro-pyrocatechol was allowed to react with 2,6-dichloro-nitrobenzene to give the title compound.The purity of the recrystallized final product was determined by means of high performance liquid chromatography and its structure was confirmed by nuclear magnetic resonance(1H NMR and13C NMR)spectroscopy.Results indicate that the target product has a purity of 99.76%.

Keywords:dioxin;1,6-dichloro-dibenzyl para-dioxin;synthesis;characterization

二噁英,又称二氧杂芑,是二噁英类化合物的一个简称,它指的是结构和性质都很相似的包含众多同类物或异构体的两大类有机化合物,包括75种多氯代二苯并二噁英和135种多氯代二苯并呋喃.这类物质非常稳定,熔点较高,极难溶于水,可以溶于大部分有机溶剂,是无色无味的脂溶性物质,因此非常容易在生物体内积累[1-3].其中以2、3、7、8-位氯取代的异构体(TCDD)毒性最大,相当于氰化钾毒性的50～100倍.这是迄今为止化合物中毒性最大且含有多种毒性的物质之一,更为严重的是二噁英具有强致癌性[4-6].当研究二噁英污染物的来源、环境行为以及对人体的危害与之相适应的分析方……