Sciencemadness Discussion Board

Can I increase acetone pH by adding a base?

math - 13-9-2012 at 03:10

Hello,

I'd like to know if it's possible to increase acetone pH to 8-10 by adding either NaOH or Ca(OH)2.

Thank you

weiming1998 - 13-9-2012 at 03:29

Quote: Originally posted by math  
Hello,

I'd like to know if it's possible to increase acetone pH to 8-10 by adding either NaOH or Ca(OH)2.

Thank you


Remember that bases (the stronger the base the faster it goes, especially solid bases dissolved in anhydrous acetone) catalyses the isomerisation of acetone to an enol(ate) , which reacts with more acetone in an aldol condensation reaction to form a mess of reddish, rather slushy, gunk. But if you work quickly, probably. Do you need anhydrous conditions or in aqueous solution? And what reaction are you trying?

Nicodem - 13-9-2012 at 07:22

Quote: Originally posted by math  
Hello,

I'd like to know if it's possible to increase acetone pH to 8-10 by adding either NaOH or Ca(OH)2.

Thank you

No, acetone does not self-dissociate in the same manner as water and related protic solvents, so the pH in acetone can not be defined in any reasonable way. Just consider: how would you measure the pH in acetone? You can dilute a sample with water and measure its pH but this value has nothing to do with anything resembling the "pH in acetone" - it only indicates the alkalinity of the solutes present in acetone, nothing more.

If you add a base to acetone, you only have a suspension or a solution of a base in acetone, nothing more. If the base is strong enough, the acetone slowly self-condenses to give diacetone alcohol.

math - 13-9-2012 at 12:54

I was reading that some plant material extractions are more efficient at a pH of 8-9, so I thought that aqueous acetone would do.

Thank you

hyfalcon - 13-9-2012 at 13:00

Stick with the Ca(OH)2 if you're doing plant extractions. Good source of food grade Ca(OH)2 is pickling lime. A good non-polar food grade solvent is d-limonene. Smells like oranges though.