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"Unwatery water"
"Optimization of the nitroaldol reaction in ionic liquids"

Agnieszka Łapczuk-Krygier
Tadeusz Kościuszko Cracow University of Technology,
Institute of Chemical Engineering and Technology,
Department of Organic Chemistry,
ul. Warszawska 24, 31-155 Kraków

pMe-CN-NS 1-cyano-2-(4-methylphenyl)-1-nitroethene, (Cracow University of Technology, May 2014

Description popularizing the research project

When we hear 'liquid' our first association is water - an apparently ideal liquid: without taste, without smell, colourless, and yet crucial for survival. It is so important because dehydration quickly leads to death, as water is a basic component and environment of every living cell of every living creature. Yet, we have to admit that water is quite a bizarre substance: it is liquid in the range of between 0 and 100°C; once the temperature exceeds 100°C or drops below 0°C, the liquid is all gone. Between the values its behaviour is not stable too as it constantly vaporises. Moreover, we know how much unhealthy is pure water. Water with ions and anions as it is listed in labels of mineral water is much better. Thus, would it be better if mineral water consisted of ions only?
It is just the 100th anniversary of obtaining the first experimental 'mineral water' without actual water called ionic liquid. It is hard to imagine such a thing that salts occur in a liquid form and they are not solutions. As it is not necessary to dissolve them, just melt them. Many such liquids are also obtained not through melting the salts but through laboratory syntheses. Research shows the liquids are free of many bizarre qualities of water: they are stable in even four times wider range of temperature, their vaporising is minimal thus their properties are much more predictable. Like water, they are a good solvent for many substances and nearly perfect environment for many reactions. It is possible to engineer an ionic liquid for a specific purpose - one for electrochemical processes like in batteries, another as an environment for a chemical reaction. In such customised, favourable conditions, quick and efficient mass production of important chemical substances is possible. Although in the world of animated nature water holds unchallenged position, it seems that in other areas the ionic liquids will prevail.


In recent years, ionic liquids became a popular reaction medium. They are used due to their unique properties: a wide range of temperatures in which they can be used, low reactivity, properties, which we can alter by changing the structure of the compound. Ionic liquids have been successfully used as catalysts in many chemical reactions. Our research focused on finding a catalyst for nitroaldol reaction. We researched the reaction of nitroalkane with substituted benzaldehyde. We applied, as a catalyst, the primary amine. The obtained yield of nitrostyrene was between 30 and 45% depending on the substituent R. With ionic liquids yield of the reaction is 97%. We used ammonium and imidazolium based ionic liquids. As the anion we used: chloride, p-toluenesulphonate, hydrosulphate, hydrophosphate. Most of the ionic liquids were obtained in our laboratory. The presented photos show the obtained compounds and ionic liquids which were used in the reactions. Many substances have a very interesting structure. One of the objectives of my project is to determine the structure of the compounds with X-ray structural analysis. It is necessary to obtain the substance as a single crystal. The photographs present the compounds before and after crystallization.


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