[shan0121]

Is it possible to hydrate the double bond on FFAs?  I know you can use H2SO4 to hydrate alkenes, but will the carboxylic end of the FFA affect that reaction?  Would the large size of the FFAs also make the hydration reaction more difficult? Thanks!!

[discodermolide]

Is it possible to hydrate the double bond on FFAs?  I know you can use H2SO4 to hydrate alkenes, but will the carboxylic end of the FFA affect that reaction?  Would the large size of the FFAs also make the hydration reaction more difficult? Thanks!!

The carboxylic ace could interfere, depending upon how far away it is from the double bond.
A long chain fatty acid my make the reaction more difficult due to its insolubility in polar solvents. That means the system may well become in homogenous and slow things down. Good stirring required.

[shan0121]

Thanks for the response.  If I did decarboxylate the FFA, through soda lime reaction for example, would stirring the resulting alkene with H2SO4 be enough to ensure that the reaction will be complete?  I'm thinking of utilizing sonication, which should definitely cause thorough mixing.

[discodermolide]

Thanks for the response.  If I did decarboxylate the FFA, through soda lime reaction for example, would stirring the resulting alkene with H2SO4 be enough to ensure that the reaction will be complete?  I'm thinking of utilizing sonication, which should definitely cause thorough mixing.

That should work if your sonication unit is efficient enough. If not use a paddle stirrer mechanically at high RPM. I do't know what scale you are operating on here, but I assume a mechanical stirrer would be ok?

[shan0121]

Right now we're working on making sure that our reactions work in the sequence that we want, so it is laboratory scale for now.  We are hoping to be able to take this to industrial scale production in the future.

[discodermolide]

Right now we're working on making sure that our reactions work in the sequence that we want, so it is laboratory scale for now.  We are hoping to be able to take this to industrial scale production in the future.

Well if that is the case do not sonicate, I'm not aware of anything that can sonicate say a 1000L reactor. In these reactors you can get extremely efficient stirring and mixing.
I suggest you use a mechanical stirrer based on such a design for your lab experiments, then you will have a better chance of an efficient scale-up.

[shan0121]

So you don't see sonication being an option when we scale it up?  Our concept is to have a flow system, we may need to have the fluid pass through the sonicator multiple times, but that is okay with us.

[discodermolide]

So you don't see sonication being an option when we scale it up?  Our concept is to have a flow system, we may need to have the fluid pass through the sonicator multiple times, but that is okay with us.

OK in that case it is not a problem. I assumed a batch reaction.