Unexpected rate retardation in the formation of phthalic anhydride from N-Methylphthalamic Acid in acidic H2O-CH3CN medium
Kinetic study on the cleavage of N-methylphthalamic acid (NMPA) in mixed acidic aqueous-acetonitrile solvent reveals the formation of both phthalic anhydride (PAn) (through O-cyclization) and N-methylphthalimide (NMPT) (through N-cyclization). The formation of NMPT varies from similar to 20% to simi...
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| Main Authors: | , |
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| Format: | Article |
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2005
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| Subjects: | |
| Online Access: | http://eprints.um.edu.my/8044/ http://koreascience.or.kr/article/ArticleFullRecord.jsp?cn=JCGMCS_2005_v26n7_1037 |
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| Summary: | Kinetic study on the cleavage of N-methylphthalamic acid (NMPA) in mixed acidic aqueous-acetonitrile solvent reveals the formation of both phthalic anhydride (PAn) (through O-cyclization) and N-methylphthalimide (NMPT) (through N-cyclization). The formation of NMPT varies from similar to 20% to similar to 3% with the increase in the content of acetonitrile from 2 to 70% v/v. Pseudo first-order rate constants for the formation of PAn are more than 4-fold larger than those for the formation of NMPT at 2% v/v CH3CN in mixed aqueous solvents. Pseudo first-order rate constants for alkaline hydrolysis of NMPT reveal a nonlinear decrease with increase in the content of CH3CN in mixed aqueous solvents. |
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