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From Current Science to School – the Facets of Green Chemistry on the Example of Ionic Liquids
Daniel Rauber, Frederik Philippi, Johann Seibert, Johannes Huwer, Harald Natter, Rolf Hempelmann
World Journal of Chemical Education
.
2019
, 7(2), 153-165 doi:10.12691/wjce-7-2-15
Fig
ure
1.
Molecular structures of some important cations and anions used for the formation of ionic liquids and notable characteristics in the context of green and sustainable chemistry
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Fig
ure
2.
Scheme of the Ruhrchemie/ Rhône-Poulenc oxo process. a) reaction scheme and structure of the rhodium catalyst. b) Formation of biphasic liquid mixture that is split in a separator to obtain the organic product phase. The catalyst remains dissolved in water and is recycled by the aqueous phas
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Fig
ure
3.
Scheme of the BASIL™ process. The chlorophenylphosphine reacts with the alcohol in a jet stream reactor to the alkoxyphenylphosphine. The hydrogen chloride generated in the reaction is scavenged with 1-methylimidazole forming the IL 1-methylimidazolium chloride, that is in liquid state under the applied reaction conditions. Due to the different polarity and density, a liquid biphasic system is formed that can be easily worked up. The upper phase contains thereby the solvent-free product while the ionic liquid is localized in the lower phase. The initial 1-methylimidazole is regenerated by neutralization with sodium hydroxide for reuse in further production cycles
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Figure
4.
Scheme of the Brønsted acid catalyzed esterification of carboxylic acid and alcohol
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Figure 5.
Molecular structure of the ionic liquid 1-butyl-3-methylimidazolium hydrogen sulfate used as catalyst for the esterification
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Figure 6.
Reaction course of the esterification reaction with the Brønsted acidic ionic liquid [BMIM][HSO
4
] as catalyst. At the beginning of the reaction, the polar educts form a homogenous mixture with the IL. After several minutes in the water bath, a second phase of the nonpolar reaction product is formed. The separation is facilitated since the density of the product is much lower compared to the density of the IL phase
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Figure 7.
Molecular structures of the esters synthesized with the Brønsted acidic ionic liquid [BMIM][HSO
4
], their characteristic scents and the yields obtained after 30 minutes at 80°C
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