Journal
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
Volume 47, Issue 21, Pages 8043-8047Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ie800126t
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- REPSOL YPF
- Spanish DGI [CTQ06-06859]
- EU
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Four nitrogen-containing organic compounds [1,5,7-triazabicyclo(4,4,0)dec-5-ene, 4-(N,N-dimethylamino)pyridine. N-methylimidazole, and L-proline] have been tested as organocatalysts for the reaction of dimethyl carbonate with an aromatic diamine, 2,4-diaminotoluene (DAT). Although, generally, N-methylation was the predominant process, variable proportions of N-carbamoylation were also observed. Reaction kinetics indicates that N-methylation and N-carbamoylation are independent and parallel processes. DAT conversion increases as the temperature increased over the range of 105-125 degrees C. Besides the nature of the organocatalyst, the ratio between N-methylation/N-carbamoylation was influenced by the DAT-to-DMC ratio: higher DAT proportions increased the DAT conversion and favored N-carbamoylation. 4-(N,N-dimethylamine)pyridine was determined to be the most active organocatalyst of the series and, under certain conditions, can lead to selective N-methylation with high conversion.
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