Abstract
The investigation results of an efficient pathway for the synthesis of high-performance 1, 4-diketo-3, 6- diphenyl pyrrolo [3, 4-c] pyrroles pigments using diethyl succinate in ionic liquids ([BMIM][BF4], and [HMIM][BF4]) has been reported. Synthesis of 3, 6-Bis (4-chlorophenyl)-2, 5-dihydropyrrolo [3, 4-c] pyrrole-1, 4-dione using [BMIM][BF4] is more efficient (81% at 30°C) than conventional methods (70% at 105-110°C). 3, 6-Bis (4-bromophenyl)-2, 5- dihydropyrrolo [3, 4-c] pyrrole-1, 4-dione was produced in this approach with 73% yield at 30°C in 8 h reaction time instead of the previously reported (65% yield in 24 h). The production yield of 1, 4-diketo-3, 6-diphenyl pyrrolo [3, 4-c] pyrroles was not highly affected by ionic liquids, and produced in maximum 43% yield.
The crystalline phase, particle sizes and morphologies of the synthesized pigments have also been reported.
Keywords: Crystalline phase, diethyl succinate, diketopyrrolopyrole, pigment, Ionic liquid
Letters in Organic Chemistry
Title:An Efficient Pathway to Synthesize Diketopyrrolopyrrole Pigments in Ionic Liquids
Volume: 10 Issue: 2
Author(s): Farahnaz Nourmohammadian and S. Shiva Shamekhi
Affiliation:
Keywords: Crystalline phase, diethyl succinate, diketopyrrolopyrole, pigment, Ionic liquid
Abstract: The investigation results of an efficient pathway for the synthesis of high-performance 1, 4-diketo-3, 6- diphenyl pyrrolo [3, 4-c] pyrroles pigments using diethyl succinate in ionic liquids ([BMIM][BF4], and [HMIM][BF4]) has been reported. Synthesis of 3, 6-Bis (4-chlorophenyl)-2, 5-dihydropyrrolo [3, 4-c] pyrrole-1, 4-dione using [BMIM][BF4] is more efficient (81% at 30°C) than conventional methods (70% at 105-110°C). 3, 6-Bis (4-bromophenyl)-2, 5- dihydropyrrolo [3, 4-c] pyrrole-1, 4-dione was produced in this approach with 73% yield at 30°C in 8 h reaction time instead of the previously reported (65% yield in 24 h). The production yield of 1, 4-diketo-3, 6-diphenyl pyrrolo [3, 4-c] pyrroles was not highly affected by ionic liquids, and produced in maximum 43% yield.
The crystalline phase, particle sizes and morphologies of the synthesized pigments have also been reported.
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Cite this article as:
Nourmohammadian Farahnaz and Shiva Shamekhi S., An Efficient Pathway to Synthesize Diketopyrrolopyrrole Pigments in Ionic Liquids, Letters in Organic Chemistry 2013; 10 (2) . https://dx.doi.org/10.2174/1570178611310020012
DOI https://dx.doi.org/10.2174/1570178611310020012 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
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