Wilgerodt Questions

Blammo

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Ive seen this as a pathway from styrene to phenylacetic acid, and I have some questions.

One, is an acidic hydrolysis, preferably using hydrochloric acid, can the production of hydrogen sulphide be avoided?

Two, can hydrogen sulphide be avoided in any way in the hydrolysis step, out side of leading any gas produced to the outside or to solutions that will absorb it?

Three, could piperazine be used instead of morpholine? I know this is extremely unlikely, but it's exacrly like morpholine but with two nitrogens instead of one, and I was hoping it could react with two molecules of styrene at once, to produce twice the phenylacetic acid. Again, I figured why not ask.

Four, is pressure required with morpholine, or any other amine besides ammonia? Several are listed on a page on erowid, such as piperidine (which is why I ask about piperazine, similar to piperidine). The temp reaction with morpholine is given as reflux temp, so I wonder if pressure is needed for lower boiling amines.

Thank you!
 

mewnmewamine

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Yup!!! Piperazine would form phenylthioacetopiperazine rather than phenylthioacetmorpholide but the process is the same.
 

Blammo

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Would you be able to say if piperazine could react with two molecules of styrene at once, since it has two available nitrogens?
 
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