Basify an oil

[JMiller]

trying to basify and oil that is pH 7.

 

Dumped straight into a 35% NaOH sol., mixed very well, extracted with DCM, distilled off DCM, but result was a paltry pH 7.8.

 

Am I missing something here? If I dissolve in solvent such as MeOH or IPA first will this help in the basifying process?

 

thanks!

[Horza2002]

Well the basisity of a solution depends on the concentration of H3O+ ions (i.e. the same as what makes a solution acidic). This means that the ions that make something acidic/basic will only stay in the aqueous phase. If you extracted with DCM, then the majoirty of the ions would have stayed in the aqueous layer and so you wouldn;t change the pH.

 

Also, what do you mean by having an oil? Is your product and oil or does it just have some solvent trapped in it preventing it becoming a solid. If its the first, the it wont dissolve very well in water anyway so when you added it to the NaOH not much will happen. If you want the oil to mix better with water, then try dissolving it in THF (it easily mixes with water and then easy enough to vac of at the ened so you can reextract your oil). But in term of making the oil basic in the organic phase, I don't think your going to get that to happen unless you use an organic base (say triethyl amine, DMAP, DBU, etc) because NaOH just wont dissolve in the DCM.