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I'm trying to find some literature on the subject of precipitating compounds that have been converted to a salt after being protonated with a strong acid (such as HCl, for example). I seem to be running into a wall once the salt is in the solution. I've tried searching via Google and Wikipedia, but I must not be searching for the correct terms because the majority of what I find covers precipitating proteins from solution, and don't seem to be relevant. The one document I found that seems to be decent is this PDF, which in the first sentence states:

I have undertaken a few experiments on the precipitation of salts from aqueous solutions by alcohol or acetone.

So that is a nice little bit of information - alcohol or acetone can be used to precipitate salts out of aqueous solutions. Unfortunately, the rest of the PDF isn't publicly available. And searching for using alcohol or acetone to extract salts from liquids seems to go back to the protein related results I mentioned above.

I don't have a specific compound or reaction in mind here, but rather a general inquiry on extracting salts that are the result of a base being protonated with HCl.

Question: Once a compound has been protonated with HCl and converted to a salt, what's the ideal way to precipitate said salt from the aqueous solution? Is acetone or alcohol the most sufficient route? Any links to some literature on the topic would be appreciated.

P.S. I'm not a trained chemist by any means (obviously). I'm a software engineer by trade, but I enjoy learning about organic chemistry as a hobby on the side.

Thank you.

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closed as too broad by Mithoron, Buttonwood, A.K., Nuclear Chemist, airhuff Feb 14 at 20:36

Please edit the question to limit it to a specific problem with enough detail to identify an adequate answer. Avoid asking multiple distinct questions at once. See the How to Ask page for help clarifying this question. If this question can be reworded to fit the rules in the help center, please edit the question.

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    $\begingroup$ You have to be more specific. What is the solvent and what compounds are dissolved in it, exactly? Note that there are often multiple ways of separating the target salt from the solution, and the one that would work the best depends on what exactly you are trying to extract. Also, the paper you are referencing to is literally over a century old; extraction techniques are advancing over time. $\endgroup$ – andselisk Feb 12 at 2:18
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    $\begingroup$ It depends. Are you trying to ppt inorganic or organic salts? It also depends on the very specific nature of what you are trying to do. // In general ionic salts are less soluble in a alcohol/water or acetone/water mixtures than water alone. $\endgroup$ – MaxW Feb 12 at 2:21
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    $\begingroup$ One thing that always concerns me about home chemists is safety. Many organic solvents like acetone and ethanol are flammable. So you should have a proper hood to use them. Also it is best to have hotplates or electric mantels rather than an open flame when using flammable solvents. As a chemist you should also never be working alone. So many well founded safety practices just get overlooked by a typical home chemist. $\endgroup$ – MaxW Feb 12 at 4:44
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    $\begingroup$ @MaxW Yeah I have that on my notes - A fan that won't cause any type of spark or short. I haven't started it yet, but I plan on going full nerd on it, using Arduino (or Raspberry Pi) to add some sensors to it to detect smoke/fire/gas/combustibles/etc, and maybe kick on the fan automatically if needed. It will also have a water circulation system and drain (that will feed into a HDPE reservoir). Its a complicated build, but I'm pretty excited about it. $\endgroup$ – Justin Feb 13 at 19:14
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    $\begingroup$ This may sound weird, but I like the research that goes into being as safe as possible. I learn a lot reading through the MSDS documents or safety related documentation. Most importantly, I respect the chemicals and compounds I'm working with and never underestimate them or get overly-confident while handling them. $\endgroup$ – Justin Feb 13 at 19:18