莎稗磷合成工艺研究
发布时间：2018-12-21 14:58
【摘要】：莎稗磷是西德Hoechst公司七十年代后期发明的一种有机磷类除草剂。化学名称O,O-二甲基-S-4-氯-N-异丙基苯氨基甲酰基甲基二硫代磷酸酯,是由N-氯乙酰基-N-异丙基-对氯苯胺和O,O-二甲基二硫代磷酸盐缩合而成。本文以对氯苯胺、2-溴丙烷为原料合成中间体N-氯乙酰基-N-异丙基-对氯苯胺,以五硫化二磷、甲醇为原料合成中间体O,O-二甲基二硫代磷酸铵,进而制得产品莎稗磷并且优化了合成工艺。以对氯苯胺和2-溴丙烷为原料合成N-异丙基对氯苯胺。探究了反应的影响因素,对产物进行了核磁共振氢谱的表征。在最优条件下,产率可达95%,纯度可达96.8%。接下来用N-异丙基对氯苯胺与氯乙酰氯反应制得N-氯乙酰基-N-异丙基-对氯苯胺。该步反应较为容易进行,在优化了反应条件之后,产率可达99%,纯度可达98%以上。以五硫化二磷和甲醇为原料合成O,O-二甲基二硫代磷酸,接着向反应体系通氨气制得O,O-二甲基二硫代磷酸铵。探究了影响反应的关键因素如溶剂、物料比、温度、催化剂,得到了最佳反应条件,目标产物收率可达75.3%,纯度99%。在制得两个重要的中间体后,对二者进行缩合反应。反应以正己烷为溶剂可达到很好的收率和纯度。优化了反应条件之后,收率可达90%,纯度可达97%。用正己烷取代传统工艺中的甲苯作为溶剂,降低了成本,避免了甲苯的毒性,并且取得了更好的效果。
[Abstract]:Saspalum is an organophosphorus herbicide invented by Hoechst Company in West Germany in the late 1970s. The chemical name Oo-dimethyl-S-4-chloro-N-isopropylphenylamino-methyl dithiophosphate was synthesized by condensation of N- chloro-acetyl-N-isopropyl-p-chloroaniline and OO- dimethyl dithiophosphate. In this paper, the intermediate N-chloroacetyl-N-isopropyl-p-chloroaniline was synthesized from p-chloroaniline and 2-bromopropane. The product of salicarp was obtained and the synthetic process was optimized. N-isopropyl p-chloroaniline was synthesized from p-chloroaniline and 2-bromopropane. The influencing factors of the reaction were investigated, and the products were characterized by nuclear magnetic resonance spectroscopy (NMR). Under the optimum conditions, the yield can reach 95% and the purity can reach 96.88%. Then N-chloroacetyl-N-isopropyl-p-chloroaniline was prepared by the reaction of N-isopropyl p-chloroaniline with chloroacetyl chloride. After optimizing the reaction conditions, the yield can reach 99% and the purity can reach more than 98%. OO- dimethyl dithiophosphoric acid was synthesized from diphosphate pentasulfide and methanol. The key factors affecting the reaction, such as solvent, material ratio, temperature and catalyst, were investigated. The optimum reaction conditions were obtained. The yield of the target product was up to 75.3 and the purity was 99.3. After two important intermediates were prepared, the two intermediates were condensed. The yield and purity of the reaction can be achieved by using n-hexane as solvent. After optimizing the reaction conditions, the yield can reach 90% and the purity can reach 97%. Using n-hexane as solvent instead of toluene in traditional process can reduce the cost, avoid the toxicity of toluene, and obtain better results.
【学位授予单位】：南京理工大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：TQ457.2
[Abstract]:Saspalum is an organophosphorus herbicide invented by Hoechst Company in West Germany in the late 1970s. The chemical name Oo-dimethyl-S-4-chloro-N-isopropylphenylamino-methyl dithiophosphate was synthesized by condensation of N- chloro-acetyl-N-isopropyl-p-chloroaniline and OO- dimethyl dithiophosphate. In this paper, the intermediate N-chloroacetyl-N-isopropyl-p-chloroaniline was synthesized from p-chloroaniline and 2-bromopropane. The product of salicarp was obtained and the synthetic process was optimized. N-isopropyl p-chloroaniline was synthesized from p-chloroaniline and 2-bromopropane. The influencing factors of the reaction were investigated, and the products were characterized by nuclear magnetic resonance spectroscopy (NMR). Under the optimum conditions, the yield can reach 95% and the purity can reach 96.88%. Then N-chloroacetyl-N-isopropyl-p-chloroaniline was prepared by the reaction of N-isopropyl p-chloroaniline with chloroacetyl chloride. After optimizing the reaction conditions, the yield can reach 99% and the purity can reach more than 98%. OO- dimethyl dithiophosphoric acid was synthesized from diphosphate pentasulfide and methanol. The key factors affecting the reaction, such as solvent, material ratio, temperature and catalyst, were investigated. The optimum reaction conditions were obtained. The yield of the target product was up to 75.3 and the purity was 99.3. After two important intermediates were prepared, the two intermediates were condensed. The yield and purity of the reaction can be achieved by using n-hexane as solvent. After optimizing the reaction conditions, the yield can reach 90% and the purity can reach 97%. Using n-hexane as solvent instead of toluene in traditional process can reduce the cost, avoid the toxicity of toluene, and obtain better results.
【学位授予单位】：南京理工大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：TQ457.2
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