Method of producing phthaloyl dichloride compound, catalyst for use in the method, and method of forming the catalyst

Abstract

A method of producing a phthaloyl dichloride compound, the method including: providing a compound represented by the following formula (1) and a compound represented by the following formula (2); and bringing the compound represented by the following formula (1) and the compound represented by the following formula (2) into reaction, so as to form a compound represented by the following formula (3), in the presence of at least one compound selected from a zirconium compound, a hafnium compound, and zinc oxide; wherein, in formulae, X represents a hydrogen atom, a halogen atom, a nitro group, a methyl group, or a methoxy group; when the X is plural, Xs may be the same or different from each other; n represents an integer of from 0 to 2; R represents a halogen atom, a chlorocarbonyl group, a low carbon number alkyl group, or a halogen-substituted low carbon number alkyl group; when the R is plural, Rs may be the same or different from each other; and m represents an integer of from 0 to 2.

1 . A method of producing a phthaloyl dichloride compound, the method comprising:
 providing a compound represented by formula (2-1) and a compound represented by formula (2-2); and   bringing the compound represented by formula (2-1) and the compound represented by formula (2-2) into reaction, so as to form a compound represented by formula (2-3) of high purity, using zinc oxide as a catalyst,   
       
         
           
           
               
               
           
         
         wherein, in formulae, X 2  represents a hydrogen atom or a halogen atom; R 2  stands for a substituent selected from the group consisting of a halogen atom, an alkyl group having a carbon number of 1 to 3, and a halogen-substituted alkyl group having a carbon number of 1 to 3; when the R 2  is plural, R 2 s may be the same or different from each other; and m represents an integer of from 0 to 2. 
       
     
     
         2 . The method of producing a phthaloyl dichloride compound according to  claim 1 , wherein the purity of the obtained compound represented by formula (2-3) is higher than 97%. 
     
     
         3 . The method of producing a phthaloyl dichloride compound according to  claim 1 , wherein the purity of the obtained compound represented by formula (2-3) is 99% or more. 
     
     
         4 . The method of producing a phthaloyl dichloride compound according to  claim 1 , wherein the purity of the obtained compound represented by formula (2-3) is in a range of from 98% to 99.7%. 
     
     
         5 . The method of producing a phthaloyl dichloride compound according to  claim 1 , wherein the compound represented by formula (2-1) is phthalic anhydride. 
     
     
         6 . The method of producing a phthaloyl dichloride compound according to  claim 1 , wherein the compound represented by formula (2-1) is 3-chlorophthalic anhydride or 4-chlorophthalic anhydride. 
     
     
         7 . The method of producing a phthaloyl dichloride compound according to  claim 1 , wherein the compound represented by formula (2-2) is 1-chloro-4-(trichloromethyl)benzene. 
     
     
         8 . The method of producing a phthaloyl dichloride compound according to  claim 1 , wherein the compound represented by formula (2-2) is (trichloromethyl)benzene.