Regioselective Mononitration of Simple Aromatic Compounds under Mild Conditions in Ionic Liquids^†

Keith Smith,*Shifang Liu, andGamal A. El-Hiti^‡

Centre for Clean Chemistry, Department of Chemistry, University of Wales Swansea, Singleton Park, Swansea, SA2 8PP, United Kingdom

Ind. Eng. Chem. Res., 2005, 44 (23), pp 8611–8615

DOI: 10.1021/ie050047z

Publication Date (Web): April 19, 2005

Abstract

Regioselective mononitration of simple aromatic compounds has been investigated in several different air- and moisture-stable ionic liquids. Use of a mixture of nitric acid and acetic anhydride as the nitrating reagent gave rise to enhanced reactivitites and improved para-selectivities for halogenobenzenes compared to those in a molecular solvent, CCl₄. In addition, the ionic liquid could be recovered easily and reused, which opens up the possibility of a more economic process.

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Article

Regioselective Mononitration of Simple Aromatic Compounds under Mild Conditions in Ionic Liquids^†

Abstract

Design of Ionic Liquid 3-Methyl-1-sulfonic Acid Imidazolium Nitrate as Reagent for the Nitration of Aromatic Compounds by in Situ Generation of NO₂ in Acidic Media

Regioselective Mononitration of Aromatic Compounds Using Keggin Heteropolyacid Anion Based Brønsted Acidic Ionic Salts

Room-Temperature Ionic Liquids: Solvents for Synthesis and Catalysis. 2

Pd−mBDPP-Catalyzed Regioselective Internal Arylation of Electron-Rich Olefins by Aryl Halides

Prospective Symbiosis of Green Chemistry and Energetic Materials

Preparative-scale synthesis of amino coumarins through new sequential nitration and reduction protocol

A green and efficient trinitration system for aromatic compounds with Bi(NO3)3·5H2O/[HMIM]ClO4 as catalyst in HNO3/Ac2O

An efficient method to synthesize TNAD by the nitration of 1,4,5,8-tetraazabicyclo-[4,4,0]-decane with N2O5 and acidic ionic liquids

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Ionic liquids: Solubility parameters and selectivities for organic solutes

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Lanthanide Bis[(trifluoromethyl)sulfonyl]imides as Reusable Catalysts for Mononitration of Substituted Benzenes in Ionic Liquids

Nitration of Substituted Benzenes Catalyzed by Metal Bis[(perfluoroalkyl)sulfonyl]imides in Quaternary Ammonium Ionic Liquids

Aromatic nitration using nitroguanidine and EGDN

A green and novel procedure for the preparation of ionic liquid

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Regioselective Mononitration of Simple Aromatic Compounds under Mild Conditions in Ionic Liquids†

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Regioselective Mononitration of Simple Aromatic Compounds under Mild Conditions in Ionic Liquids^†