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Open AccessArticle

Chlorination of Toluene to o-Chlorotoluene Catalyzed by Ionic Liquids

Faculty of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, China
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Author to whom correspondence should be addressed.
Catalysts 2018, 8(11), 532; https://doi.org/10.3390/catal8110532
Received: 13 October 2018 / Revised: 5 November 2018 / Accepted: 5 November 2018 / Published: 9 November 2018
(This article belongs to the Section Catalysis in Organic and Polymer Chemistry)
Ionic liquids with [BMIM], [Et3NH], and [BPy] cations and AlnCl3n+1, ZnnCl2n+1, and CunCln+1 anions were used as the catalysts for the chlorination of toluene with Cl2. The ZnnCl2n+1 containing ionic liquids with high Lewis acid strength had high catalytic activity for the selective chlorination of toluene to o-chlorotoluene via the electrophilic substitution reaction. Dichlorotoluenes were favorably formed when the AlnCl3n+1 containing ionic liquids with both Lewis and Brönsted acid sites were used as the catalysts. When the CunCln+1 containing ionic liquids with weak Lewis acid strength were used as the catalysts, more benzyl chloride was formed via the radical chlorination of methyl group. When the [BMIM]Cl-2ZnCl2 ionic liquid was used as the catalyst, after reacting at 80 °C for 8 h, the conversion of toluene was 99.7% and the selectivities of o-chlorotoluene, p-chlorotoluene, m-chlorotoluene, benzyl chloride, and dichlorotoluenes were 65.4%, 26.0%, 4.0%, 0.4%, and 4.2%, respectively. The [BMIM]Cl-2ZnCl2 ionic liquid catalyst had good recycling performance. View Full-Text
Keywords: ionic liquids; toluene; chlorination; o-chlorotoluene ionic liquids; toluene; chlorination; o-chlorotoluene
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MDPI and ACS Style

Wang, A.; Zhu, X.; Yin, H.; Fu, Y.; Hou, X. Chlorination of Toluene to o-Chlorotoluene Catalyzed by Ionic Liquids. Catalysts 2018, 8, 532.

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