Study On Triphosgene In The Preparation Of Acyl Chlorides

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.