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Author: Subject: Ionic liquids
Xrpdguy
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cool.gif posted on 10-1-2020 at 00:25
Ionic liquids


Hello there, is anyone interested in ionic liquids? I have a question.
If I want to use morpholine (as a cation) I need to substitute two methyl groups on nitrogen. I have tried with methyl- iodide but I am not sure when I have got at the end. :o

Did anyone try something similar?

Also, I am interested in comparing different cations and anions. Mostly using a microwave.
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j_sum1
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[*] posted on 10-1-2020 at 00:37


So you are trying to synthesise morpholine? That much was not obvious from the thread title.

Interesting structure. Someone will likely be along to help. But in the meantime, it would help to give some details of your procedure.
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Xrpdguy
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[*] posted on 10-1-2020 at 12:25


No no, I don't want to synthesize morpholine. I just wanted to make morpholinium iodide by using morpholine and methyl iodide.
Somewhere on the internet, I have found some interesting articles about methylation of lidocaine (also "making" positive charge on nitrogen atom) by using a conventional type of heating.

They took one mol of lidocaine and two mols of methyl-iodide and refluxed it in absolute ethanol for about five days. After that, all solvent was evaporated and the product was washed with warm hexane.

In my case, I wanted to use a microwave to heat the vial and catalyze the reaction and without using any solvent. It needed about 15 minutes but i am not sure what to expect.
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[*] posted on 10-1-2020 at 13:54


I used an ionic liquid made from ethanolamine and acetic acid, ethanolamine acetate, for the synthesis of nitroalkenes from nitroalkanes and aldehydes.
Ethanolamine formate is said to work even better there.
Probably one of the most accessible ionic liquids I would say.
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[*] posted on 10-1-2020 at 14:15


Choline chloride and urea (while technically a deep eutectic) is also a really accessible as well. You can do it in a mortar and pestle by grinding up urea and slowly adding ChCl until all the urea dissolves. Great for demos because it is relativity safe compared to many of the alkyl halide based IL synthesis procedures.



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[*] posted on 10-1-2020 at 21:08


Ethylammonium nitrate to quote WiKi Ethylammonium nitrate or ethylamine nitrate[2] (EAN) is a salt
It is an odorless and colorless to slightly yellowish liquid with a melting point of 12 °C.[3] This compound was described by Paul Walden in 1914,[4][5] and is believed to be the earliest reported example of a room-temperature ionic liquid.




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Xrpdguy
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[*] posted on 11-1-2020 at 01:24


Thank all you guys but for my research, I need morpholinium or lidocainium based ILs. But it seems hard to obtain it via microwave heating (my work needs to be based on the microwave heating).

If we talk about ILs and where to use it, its a good idea to use it as a solvent and catalyst at the same time. I have tried the reaction between benzaldehyde and thiazolidinedione (TZD) by using BMIM and it was succeeded.
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