Full N,N-Methylation of 4,4′-Methylenedianiline with Dimethyl Carbonate: A Feasible Access to 4,4′-Methylene bis(N,N-Dimethylaniline)
The full N,N-methylation of 4,4′-methylenedianiline (MDA) with dimethyl carbonate (DMC) was investigated. The yield of the major product 4,4′-methylene bis(N,N-dimethylaniline) (MBDMA) reached as high as 97% over NaY catalyst at 190°C for 6 h. The catalyst could be used for two more times with accep...
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| Format: | Article |
| Language: | English |
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Wiley
2018-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2018/4627903 |
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| author | Zegang Qiu Kunjie Wang Zhiqin Li Tao Li Jinhao Bai Chanjuan Yin Xiushen Ye Haining Liu |
| author_facet | Zegang Qiu Kunjie Wang Zhiqin Li Tao Li Jinhao Bai Chanjuan Yin Xiushen Ye Haining Liu |
| author_sort | Zegang Qiu |
| collection | DOAJ |
| description | The full N,N-methylation of 4,4′-methylenedianiline (MDA) with dimethyl carbonate (DMC) was investigated. The yield of the major product 4,4′-methylene bis(N,N-dimethylaniline) (MBDMA) reached as high as 97% over NaY catalyst at 190°C for 6 h. The catalyst could be used for two more times with acceptable MBDMA yields higher than 90%. The main by-products were identified as three N-methylated derivatives. Surprisingly, the formation of the N-methoxycarbonylation product was extremely restrained, which could be produced in high yields of 98% on zinc acetate catalyst. Furthermore, the reaction pathway to the major product MBDMA was proposed. Finally, a feasible synthetic route of 4,4′-methylene bis(N,N-dimethylaniline) (MBDMA) was established, featuring a high yield, mild reaction conditions, and simple operations. |
| format | Article |
| id | doaj-art-9172c817a0a14798a86be57366a19f08 |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2018-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-9172c817a0a14798a86be57366a19f082025-02-03T06:08:25ZengWileyJournal of Chemistry2090-90632090-90712018-01-01201810.1155/2018/46279034627903Full N,N-Methylation of 4,4′-Methylenedianiline with Dimethyl Carbonate: A Feasible Access to 4,4′-Methylene bis(N,N-Dimethylaniline)Zegang Qiu0Kunjie Wang1Zhiqin Li2Tao Li3Jinhao Bai4Chanjuan Yin5Xiushen Ye6Haining Liu7College of Chemistry and Chemical Engineering, Xi’an Shiyou University, Xi’an 710065, ChinaXi’an Aerospace Composites Research Institute, Xi’an 710025, ChinaCollege of Chemistry and Chemical Engineering, Xi’an Shiyou University, Xi’an 710065, ChinaCollege of Chemistry and Chemical Engineering, Xi’an Shiyou University, Xi’an 710065, ChinaCollege of Chemistry and Chemical Engineering, Xi’an Shiyou University, Xi’an 710065, ChinaCollege of Chemistry and Chemical Engineering, Xi’an Shiyou University, Xi’an 710065, ChinaThe Qinghai Institute of Salt Lakes, The Chinese Academy of Sciences, Xining 810008, ChinaThe Qinghai Institute of Salt Lakes, The Chinese Academy of Sciences, Xining 810008, ChinaThe full N,N-methylation of 4,4′-methylenedianiline (MDA) with dimethyl carbonate (DMC) was investigated. The yield of the major product 4,4′-methylene bis(N,N-dimethylaniline) (MBDMA) reached as high as 97% over NaY catalyst at 190°C for 6 h. The catalyst could be used for two more times with acceptable MBDMA yields higher than 90%. The main by-products were identified as three N-methylated derivatives. Surprisingly, the formation of the N-methoxycarbonylation product was extremely restrained, which could be produced in high yields of 98% on zinc acetate catalyst. Furthermore, the reaction pathway to the major product MBDMA was proposed. Finally, a feasible synthetic route of 4,4′-methylene bis(N,N-dimethylaniline) (MBDMA) was established, featuring a high yield, mild reaction conditions, and simple operations.http://dx.doi.org/10.1155/2018/4627903 |
| spellingShingle | Zegang Qiu Kunjie Wang Zhiqin Li Tao Li Jinhao Bai Chanjuan Yin Xiushen Ye Haining Liu Full N,N-Methylation of 4,4′-Methylenedianiline with Dimethyl Carbonate: A Feasible Access to 4,4′-Methylene bis(N,N-Dimethylaniline) Journal of Chemistry |
| title | Full N,N-Methylation of 4,4′-Methylenedianiline with Dimethyl Carbonate: A Feasible Access to 4,4′-Methylene bis(N,N-Dimethylaniline) |
| title_full | Full N,N-Methylation of 4,4′-Methylenedianiline with Dimethyl Carbonate: A Feasible Access to 4,4′-Methylene bis(N,N-Dimethylaniline) |
| title_fullStr | Full N,N-Methylation of 4,4′-Methylenedianiline with Dimethyl Carbonate: A Feasible Access to 4,4′-Methylene bis(N,N-Dimethylaniline) |
| title_full_unstemmed | Full N,N-Methylation of 4,4′-Methylenedianiline with Dimethyl Carbonate: A Feasible Access to 4,4′-Methylene bis(N,N-Dimethylaniline) |
| title_short | Full N,N-Methylation of 4,4′-Methylenedianiline with Dimethyl Carbonate: A Feasible Access to 4,4′-Methylene bis(N,N-Dimethylaniline) |
| title_sort | full n n methylation of 4 4 methylenedianiline with dimethyl carbonate a feasible access to 4 4 methylene bis n n dimethylaniline |
| url | http://dx.doi.org/10.1155/2018/4627903 |
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