Prediction of Solubility using Organic solvents

[boblalux]

Whenever I have a stain (paint, glue etc), I attempt removing it after the following scheme (if unsuccessful, I proceed to the next solvent):
Water, soapy water, alcohol, white spirit, acetone.

My question is...
Is it possible to chemically PREDICT which solvent will be succesqsful on which material/stain?

 

[Borek]

If you know what the stain is and what the material is - sure.

 

[boblalux]

What I actually mean, is it possible on the basis of theoretical consideration of the formula of any organic substance, to find whether it is soluble in an organic solvent.

 

[Kevin McHugh]

What I actually mean, is it possible on the basis of theoretical consideration of the formula of any organic substance, to find whether it is soluble in an organic solvent.

Yes. Since like dissolves like. Any LC handbook will have a list of solvents with a polarity index. If you know what the stain is (polar vs. non-polar), then you can find a solvent with a suitable polarity from the list of solvents.