[Alkayyali]

Hi

I'm third year Chemical Engineering, and I have a project which is to produce Acetic Acid from different feed stocks. My feed stock is polystyrene, now I created my own process.

My question is how I can oxides the 2-phenylethanol to get acetic Acid or Ethanol and How much is the yield  I will get to produce Ethanol

Alkayyali

[Schrödinger]

There is one lengthy way I can think of, but starting from styrene (which you can probably get by dehyrating 2-phynylethanol). So, once you have styrene, ozonolysis and the reduction that usually follows it (reductive ozonolysis) should give formaldehyde and benzaldehyde. Now using CH₃MgBr on formaldehyde should extend the C chain by 1 unit. Acetic acid is just a couple of steps away.

[curiouscat]

Using polystyrene as a feedstock for Acetic Acid is pretty silly, if this is in any way a practical exercise.

Also 2-phynylethanol is itself typically produced from styrene commercially.

[Alkayyali]

I know, producing Acetic Acid from Polystyrene is silly, but this is my task  , however my process is to depolarize the polystyrene

polystyrene depolarization Styrene Styrene Oxide  hydrogenation Catalysts  2-phenylethanol

now here is my concern can I get Acetic Acid from 2-phenylethanol by using the ethanol and by oxaditive fermentation get Acetic Acid

and how to get Ethanol from 2-phenylethanol

and my other question is, can I get Acetic Acid from Styrene right away without going through these processes?

and could you tell me how please

regards

[orgopete]

Okay, since you are an engineer, lets do this. Reduce styrene all the way to ethylcyclohexane, brominate it and do an elimination. Now comes the engineering part, although the exocyclic product is the least favored, figure a way to reverse the thermodynamics so it is the major. Then ozonolysis will give you acetic acid after oxidative work up. The cyclohexanone can be converted to adipic acid and sold as a commercial product.

[PhDoc]

You didn't indicate just how efficient your conversion had to be, so I'll presume anything that works is acceptable.

There is at least one oxidation process that converts polystyrene to benzaldehyde and acetophenone. See Dickens... Polymer Degradation and Stability 1984, 6(4), pp 211-241.

How might you use ONE of these products to accomplish your goal? Hint: Two (2) synthetic steps from undergraduate Organic Chemistry.

Please keep in mind this information is available from SciFinder and Beilstein.

Best of luck to you!

[orgopete]

You didn't indicate just how efficient your conversion had to be, so I'll presume anything that works is acceptable.

There is at least one oxidation process that converts polystyrene to benzaldehyde and acetophenone. See Dickens... Polymer Degradation and Stability 1984, 6(4), pp 211-241.

How might you use ONE of these products to accomplish your goal? Hint: Two (2) synthetic steps from undergraduate Organic Chemistry.

Please keep in mind this information is available from SciFinder and Beilstein.

Best of luck to you!

I agree this is probably the way to go.

[Alkayyali]

well the conversion must be efficient as much as it can

sorry guy I'm an Engineer I have an idea about reactions but I don't have the enough knowledge about the reactions, so I'm confused right now I'll search that thank you anyway

[PhDoc]

Please keep in mind the most fundamental part of your problem. Ethanol is infinitely miscible with water. This is an "engineering" issue. Acetic acid is also infinitely miscible with water.

Any process you come up with will require aqueous work-up of reactions, and hence you will lose ALL your ethanol. This is the most practical solution to an impractical problem.

Air oxidation of polystyrene leads to formation of benzaldehyde and acetophenone via a radical mechanism. The benzaldehyde could be used, however you must ask yourself if it's worth the trouble. Reaction of benzaldehyde with methylmagnesium bromide affords 1-phenylethanol. Oxidation of 1-phenylethanol with PCC or chromic acid provides acetophenone.

What you want is the acetophenone, submission of which to Baeyer–Villiger oxidation leads to formation of phenyl acetate. Reaction of phenyl acetate with lithium aluminum hydride or diisobutylaluminum hydride affords ethanol. If you want the acetic acid, then saponification followed by acidic workup will get you there.

Now, if you transesterify with methanol, you'll isolate methyl acetate and phenol. The "engineering" issue here is isolating the methyl acetate is good yield. Once isolated, you can convert it to acetic acid via saponification followed by aqueous workup. Again, the "engineering" issue of isolating the acetic acid in quantity will present itself.

As I mentioned you will lose the ethanol. Isolation is impractical. If you wanted the phenol on the other hand, you'll have plenty of that.

If you can find a solution to this problem that is efficient, you'll be nominated for a Nobel Prize. If we could take all the polystyrene waste on the face of the earth, and convert it quantitatively to ethanol, that would be worth something.

The best of luck to you!