[DeP]

Dear,

I'm doing a reaction where there is sodium chloride formed in dichloromethane.
To increase the yield of my reaction I want to use other (and greener) solvents.
I went to the library to search some exact numbers of the solubilities of sodium chloride in common organic solvents.
There I found some exact solubilities, but I never found the exact number for the solubility of sodium chloride in Toluene.
I know that the exact number will be very low because toluene isn't polar and can therefore not form a solvent cage to capture the ions that can compete against the cristal interactions. But yet I would like to know an exact number?
Can somebody help my?
And does somebody know the exact number for the solubility of sodium chloride in DCM, I also didn't found it.
Thanks in advance

[Stepan]

I do not think that the exact number exists, because it changes with moisture (water impurity) content, as well as presence of other polar solvents. Even so, I would say it should be <0.1% which is considered as insoluble

[AWK]

If sodium chloride is formed as a by-product then the lower solubility the better. Generally, NaCl is practically insoluble in non-polar solvent, but you can increase its solubility by addition of crown ethers.

[DeP]

The problem is that I'm forming a Ionic liquid, with tetrabutylphosphonium as cation.
And because this is already a phase transfer catalyst, I'm already increasing the solubility of Chloride in my system.
Yet, I want to have as less of tetrabutylphosphonium chloride in my reactionmixture therefor I want to precipitate as much as possible chloride in the form of sodium chloride. And therefor I want to use a solvent where sodium chloride virtually doesn't dissolve.

[AWK]

Most ionic liquids are water immiscible, and salts can be simply removed by rinsing with water. You need to find original references close to your problem.

[DeP]

I'm working with tertabutylphosphonium chloride and I want to do an anion exchange to tertrabutylphosphonium acetate.
In literature they use mostly as solvent water. But than you have the problem that it is very difficult to separate you're ionic liquid from the salts because both are hydrofilic. That's why I tried to do the reaction in an organic solvent where Sodium chloride does not dissolve. So that it's easier to separate my pure IL.
So washing isn't an solution.