【作者】 鲍丽娜；

【导师】 莫卫民；

【作者基本信息】 浙江工业大学 ， 农药学， 2004， 硕士

【摘要】 酰氯类化合物是一种重要有机的中间体，在药物合成中有广泛的应用。在传统方法的生产过程中，采用二氯亚砜，三氯氧磷，三氯化磷，五氯化磷等作为氯化剂，但存在腐蚀生产设备，污染大的缺点。在本文中用三光气作为酰氯化剂取代以往的酰氯化剂。三光气由于其合成和参加反应的条件都比较温和，而且选择性强、收率高、使用安全方便、易运输储存，在医药、农药、有机化工和高分子材料等领域正在得到广泛的应用。但至今在国内外的化学反应和化工生产中，三光气作为酰氯化剂的很少，其主要原因是催化剂的难以选择。 本文以三光为酰氯化剂，吡啶为催化剂，甲苯为溶剂，制得了甲氰菊酰氯、氯乙酰氯、苯乙酰氯、对甲基苯甲酰氯。以三光气为酰氯化剂的四种化合物的合成未有文献报道。并对甲氰菊酰氯和氯乙酰氯进行了单因素各种方案比较，进而设计了正交试验优化条件，得到了两者合成的较佳工艺条件。 甲氰菊酰氯的最佳反应条件是反应温度是100℃，反应时间是12小时，催化剂为吡啶，其用量与菊酸等摩尔，收率为56.7％。氯乙酰氯的最佳反应条件是反应温度100℃，反应时间是10小时，催化剂为吡啶，其用量与氯乙酸等摩尔，收率为62.4％。总结菊酰氯和氯乙酰氯的反应规律，选定了合适的反应条件成功制取了苯乙酰氯和对甲基苯甲酚氯。 本合成方法产物易分离、操作方便、污染少、对设备腐蚀轻，是一种洁净的合成方法，为酚氯化合物的合成提供了一条绿色合成途径。更多还原

【Abstract】 Acyl chlorides are important organic intermediates, which is widely used in pharmaceutical synthesis. In traditional process of production, sulfinyl chloride, phosphoryl chloride, phosphorus trichloride and phosphorus pentachloride are used aschlorinating agents. This method results in the corruption of production facility and serious pollution. In this dissertation, Triphosgene is attempted to substitue agent for traditional chlorination as chloroformylating agent. Triphosgene is increasingly used in the fields of medicine, pesticide, organic chemistry and macromolecule material with advantages of mild synthesis and reaction conditions, strong selectivity, excellent yield, safe handling and handy storage and transportation. However, Triphosgene is hardly used as chloroformylating agent in organic reaction and production because the catalyst is difficult to select.In this dissertation, 2,2,3,3,-Tetramethylcyclopropanecarbonyl chloride, Chloroacetyl chloride, Phenylacetyl chloride and p-Toluoyl chloride are successfully synthesized by using Triphosgene, pyridine and toluene as chloroformylating agent, catalyst and solvent correspondingly. This method isn’t reported in current report. The factors of affecting reactions were studied with univariate analysis for 2,2,3,3,-tetramethylcy clopropanecarbonyl chloride and chloroacetyl chloride. Then the paper adopts orthog onal test to get the technological conditions of these compounds.The yields of 2,2,3,3,-Tetramethylcyclopropanecarbonyl chloride can come to 56.7% when the reaction undergo in the most suitable reaction conditions: pyridine as catalyst, pyridine: 2,2,3,3,-Tetramethylcyclopropanecarboxylic acid=1:1(mol), at 100 for 12 hours. And the yield of Chloroacetyl chloride can come to 62.4% whenthe reaction undergo in the most suitable reaction conditions: pyridine as catalyst, pyridine: chloroactic acid =1:1(mol), at 100 for 10 hours.Summarizing the reactions of 2,2,3,3,-Tetramethylcyclopropane carbonyl chloride and Chloroacetyl chloride,we select the apt conditions to get phenylacetyl chloride and p-Toluoyl chloride.New method introduced in this dissertation owns the following advantages: easy separation of production, simple operation, less pollution, less corruption of facility and clean, providing a novel friendly-environment method for the synthesis of acyl chlorides.更多还原