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Synthesis of Ionic Liquids in Microstructured Reactors – a Brief Introduction
Johannes Gutenberg University Mainz, Institute of Organic Chemistry, Chemical Micro Process Technology, Duesbergweg 10-14, 55128 Mainz, Germany
IMM Institut fuer Mikrotechnik Mainz GmbH, Carl-Zeiss-Str. 18-20, 55129 Mainz, Germany * email: email@example.com
The synthesis of Ionic Liquids (ILs) looks simple on a first sight. Mostly an amine reacts with an alkylating agent to a quaternary ammonium salt and the pathway of this reaction indicates that remarkable formation of unwanted side products is not expected, and purification by recrystallization from a suitable solvent is possible if necessary. In the case of ILs however, contrary to simple ammonium salts, cannot easily purified neither by recrystallization nor by distillation due to their physical properties. Nonetheless, the synthesized ILs have to be on highest grade quality even as raw product.
Remarks on the conventional way of ILs syntheses
The synthesis of ILs, especially from 1-alkyl-imidazole, suffers from the extreme heat release of this typically very fast reaction. By using standard batch procedure this reaction is hard to control. Normally, an alkylating agent is added drop wise to the bulky amine in the vessel to avoid hot-spots and to ensure a constant reaction temperature. How fast the temperature rise can be is given in Fig.1. To a stirred small glass vessel containing 0.065 mol 1-methyl-imidazole (room temperature) an equimolar amount of a)diethyl sulfate or b) trifluoromethyl-sulfonic acid methyl ester (triflate) was added and the temperature was measured by thermocouples. By using diethyl sulfate an induction period can be observed followed by a steep temperature rise. In the case of methyl-triflate as alkylating agent, the reaction takes place immediately, and it can be assumed that the measured temperature value is lower than the real hot-spot. Too high temperatures and too long reaction times are common reasons for low product quality, discoloration and possible polymerization.
Fig.1: Temperature rise for equimolar (0.065 mol) reaction of 1-methyl-imidazole with diethyl sulfate (left) and methyl- triflate (right). The blue line indicates the temperature change of the heat transfer liquid in the thermostat. The temperature sampling rate is 1 per second.
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