Selective synthesis of N,N-dimethyl aniline derivatives using dimethyl carbonate as a methylating agent and onium salt as a catalyst
| Title | Selective synthesis of N,N-dimethyl aniline derivatives using dimethyl carbonate as a methylating agent and onium salt as a catalyst |
| Publication Type | Journal Article |
| Year of Publication | 2005 |
| Authors | Shivarkar, AB, Gupte, SP, Chaudhari, RV |
| Journal | Journal of Molecular Catalysis A - Chemical |
| Volume | 226 |
| Issue | 1 |
| Pagination | 49-56 |
| Date Published | FEB |
| Type of Article | Article |
| ISSN | 1381-1169 |
| Keywords | Aniline, Dimethyl carbonate, methylation, N, N-alkylation, N-dimethyl aniline, onium salts |
| Abstract | N-Alkylation of anilines by dimethyl carbonate (DMC) catalyzed by onium salts has been demonstrated. The work presented here shows that a simple catalytic system consisting of onium salts in the presence of a small amount of water is extremely effective in enhancing the DMC mediated N-alkylation of anilines to dialkylated products. The effect of reaction conditions on the synthesis of N,N-dimethyl aniline (NNDMA) from aniline and DMC has been investigated. Under the optimized conditions highest yield of NNDMA obtained was 99.8%, which is the best reported for liquid phase N-alkylation of aniline using DMC. The role of water in enhancing the yield of NNDMA is explained and a reaction-networking scheme is constructed, which summarizes the chemistry behind liquid phase N-alkylation of anilines by DMC. The catalyst has been shown to recycle up to five times and at the end of fifth recycle almost 98% of NNDMA yields were obtained. (C) 2004 Elsevier B.V. All rights reserved. |
| DOI | 10.1016/j.molcata.2004.09.025 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 3.958 |