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Author: Subject: What to do with styrene?
Linus1208
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[*] posted on 7-5-2022 at 04:29
What to do with styrene?


So I have lots of styrofoam laying around and I was thinking about depolymerising it to make styrene. Just because it would be a fun project.

But it would be kind of stupid to have the styrene laying around until it just polymerises.
I also thought about oxidizing it to benzoic acid with KMnO4 and making benzene from it, but I only can order a limited amount of KMnO4 per year and I don't have that much of it.

Is there an easier way to convert it to benzene, or some other interesting EU-compatible things I could do with it?
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[*] posted on 7-5-2022 at 05:23


I too have been interested in the potential fun projects involving styrene.

You could convert it to styrene oxide:
http://www.sciencemadness.org/talk/viewthread.php?tid=15284#...

That is an epoxide, so you could do some fun things with that, perhaps react it with a nucleophile such as ammonia, to obtain the amino-alcohol (two isomers?), or with base to obtain phenyl ethylene glycol (1-phenyl-1,2-ethanediol).

Grignard reagents can also add to episodes, although I'm not sure where the Grignard would add to an unsymmetrical epoxide.


You could also hydrate styrene, ending up with 1-phenylethanol (not quite as interesting as 2-phenylethanol aka phenethyl alcohol)

You could do a hydrohalogenation to obtain 1-bromo-1-phenylethane, or try an anti-Markovnikov addition to obtain phenethyl bromide.

There was a thread on here about ozonolysis of styrene to obtain phenylacetaldehyde but I'm not sure if that's too easy.

I'm looking forward to hearing what other peoples' responses are!

BTW Styrofoam might not be the easiest thing to depolymerize unless you have some way of reducing its volume by removing the air somehow.

I would rather not waste KMnO4 in oxidising styrene, but that's just my view, haha, I'd be looking for a cheaper oxidiser
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[*] posted on 7-5-2022 at 08:58


Removing the air from styrofoam is easy- mix it with acetone. That gives you a somewhat intractable lump, but if you're just heating it to depolymerize it, the heat will remove any acetone before the reaction starts.



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Keras
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[*] posted on 7-5-2022 at 09:00


You can synthesise phenethyl alcohol which is the main component of rose perfume.
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[*] posted on 9-5-2022 at 07:21


You can get benzene from sodium benzoate and sodium hydroxide both found in any food store.
See here
http://www.sciencemadness.org/talk/viewthread.php?tid=325

Nilered has a video about the procedure here:
https://www.youtube.com/watch?v=X10VZeQmFDo

I have done it and it works well using a paintcan as dry distilling vessel (dont use glass).
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Antiswat
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[*] posted on 9-5-2022 at 16:17


iirc you can turn styrene oxide - or just styrene into benzaldehyde by passing it over heated Al2O3


ah, here goes
p.styrene heated --> styrene
styrene + alumina catalyst + O2, air --> styrene oxide/benzaldehyde
SO/Benzaldehyde + NaClO --> Benzaldehyde

redhot copper wire might also work for this, it catalyses (with airflow) alcohols to aldehydes, its a bit more tedious with higher boiling liquids though.




~25 drops = 1mL @dH2O viscocity - STP
Truth is ever growing - but without context theres barely any such.

https://en.wikipedia.org/wiki/Solubility_table
http://www.trimen.pl/witek/calculators/stezenia.html
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SplendidAcylation
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[*] posted on 11-5-2022 at 06:36


Quote: Originally posted by Antiswat  
iirc you can turn styrene oxide - or just styrene into benzaldehyde by passing it over heated Al2O3


ah, here goes
p.styrene heated --> styrene
styrene + alumina catalyst + O2, air --> styrene oxide/benzaldehyde
SO/Benzaldehyde + NaClO --> Benzaldehyde

redhot copper wire might also work for this, it catalyses (with airflow) alcohols to aldehydes, its a bit more tedious with higher boiling liquids though.



That'd be awesome if it worked!

I'm a bit sceptical of that final stage; Benzaldehyde oxidises really easily to benzoic acid with unselective oxidisers like hypochlorite.

I have tried a number of times to oxidise benzyl alcohol to benzaldehyde using NaOCl, supposedly high yielding according to a paper somewhere, but it really isn't very effective in my experience; It seems to result in a mixture of benzyl alcohol, benzaldehyde, and benzoic acid, the smell of benzaldehyde is immediately evident, though!



Edit:

I mentioned earlier the addition of a Grignard reagent to styrene oxide, I've since found out that the Grignard will add to the least substituted carbon, so:

R-MgX + styrene oxide ---> C6H5-CH(OH)-CH2-R

(Quench stage not included in above unbalanced reaction)

[Edited on 11-5-2022 by SplendidAcylation]
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Antiswat
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[*] posted on 11-5-2022 at 20:15


well H2CrO4 i can also attest works for benzyl alcohol, and with either careful timing or adding in additional reagents youre supposedly able to stop it quite accurately at the aldehyde



~25 drops = 1mL @dH2O viscocity - STP
Truth is ever growing - but without context theres barely any such.

https://en.wikipedia.org/wiki/Solubility_table
http://www.trimen.pl/witek/calculators/stezenia.html
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[*] posted on 12-5-2022 at 10:53


Regarding aminoalcohols, i made fepradinol, halostachine and their N-ethyl analogue easily from styrene oxide, its just important you keep the amine in excess always and add the epoxide slowly.
Little amine like methylamine require an excess of ideally at least 4eq., though, but with isobutanolamine for fepradinol, I just used equimolar quantities.




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[*] posted on 12-5-2022 at 13:39


Quote: Originally posted by Antiswat  
well H2CrO4 i can also attest works for benzyl alcohol, and with either careful timing or adding in additional reagents youre supposedly able to stop it quite accurately at the aldehyde


As you can attest, please enlighten us with the how to!
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Antiswat
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[*] posted on 12-5-2022 at 23:35


Tsjerk
very easy. mix it lol
theres also some H2SO4 in it, not sure if that does anything- but it gets warm right away, upon standing you get benzoic acid- i suppose dumping in some hexane after a bit of time would get you benzaldehyde in hexane, then just distill off the hexane
if you fancy driving a bit, then you might be able to buy 1000L 30% H2CrO4 solution and more, check reagents and acquisition




~25 drops = 1mL @dH2O viscocity - STP
Truth is ever growing - but without context theres barely any such.

https://en.wikipedia.org/wiki/Solubility_table
http://www.trimen.pl/witek/calculators/stezenia.html
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[*] posted on 13-5-2022 at 00:24


Quote: Originally posted by Antiswat  
Tsjerk
very easy. mix it lol
theres also some H2SO4 in it, not sure if that does anything- but it gets warm right away, upon standing you get benzoic acid- i suppose dumping in some hexane after a bit of time would get you benzaldehyde in hexane, then just distill off the hexane
if you fancy driving a bit, then you might be able to buy 1000L 30% H2CrO4 solution and more, check reagents and acquisition


Mix it lol would be the summary of any write-up, literally. Please detail the procedure a bit more so your post will bear meaning. Reaction conditions are a minimum, yields as well. Without you could as well have posted nothing.
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Linus1208
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[*] posted on 23-5-2022 at 03:22


Quote: Originally posted by SplendidAcylation  

BTW Styrofoam might not be the easiest thing to depolymerize unless you have some way of reducing its volume by removing the air somehow.

I was thinking about either carefully melting it and squishing it down, or just dissolving it in acetone (I have 300ml of Acetone I accidentally contamined with iron(III) compounds, so I can't use it for other stuff either way).

Quote: Originally posted by SplendidAcylation  

I would rather not waste KMnO4 in oxidising styrene, but that's just my view, haha, I'd be looking for a cheaper oxidiser

That's what I was thinking to. I only know one shop that sells it in germany, and they only sell a limited amount of it per year and person.
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Linus1208
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[*] posted on 23-5-2022 at 05:53


Quote: Originally posted by Antiswat  
iirc you can turn styrene oxide - or just styrene into benzaldehyde by passing it over heated Al2O3


ah, here goes
p.styrene heated --> styrene
styrene + alumina catalyst + O2, air --> styrene oxide/benzaldehyde
SO/Benzaldehyde + NaClO --> Benzaldehyde

redhot copper wire might also work for this, it catalyses (with airflow) alcohols to aldehydes, its a bit more tedious with higher boiling liquids though.


So you're saying styrene can be oxidized with Al2O3 catalyst and air to a mix of SO and Benzaldehyde.
And SO will be oxidized to benzaldehyde with NaClO? That would be great.

I'm not sure if the benzaldehyde would oxidize further to benzoic acid, as NaClO is not a very selective oxidizer. Either way I would have planned to oxidize it to benzoic acid either way so I wouldn't really care.
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[*] posted on 24-5-2022 at 01:27


MnO2 may also work- it does work to turn benzyl alcohol into benzaldehyde, unsure if it requires oxygen for this
if you have a bulk you could try using lower than 30% HClO3, this will also form some chlorinated stuff but its very easily affordable to make in big amounts, above 30% it becomes dangerous to work with

H2CrO4 can effectively turn benzyl alcohol into benzoic acid if left to stand for a bit

if you want concentrated NaClO, pool chlorinating agents usually react with NaOH to form concentrated NaClO




~25 drops = 1mL @dH2O viscocity - STP
Truth is ever growing - but without context theres barely any such.

https://en.wikipedia.org/wiki/Solubility_table
http://www.trimen.pl/witek/calculators/stezenia.html
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[*] posted on 24-5-2022 at 09:07


Phenylacetic acid from styrene
https://www.sciencemadness.org/whisper/viewthread.php?tid=15...
Chloroacetophenone and styrene chlorohydrin from styrene
https://www.sciencemadness.org/whisper/viewthread.php?tid=15...

Before pyrolysis styrofoam need to smelt. Can of paint from stell can be used as retort. Pyrolysis 1 kg storofoam gives about 0.5 kg styrene after redistillation and collection fraction 140-150C
Pyrolysis polystyrene is endothermic reaction and it rate depends on heat rate. Time pyrolysis can vary from 30-40 minutes and some days. It depends from power of heater


[Edited on 24-5-2022 by Hexabromobenzene]
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Linus1208
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[*] posted on 24-5-2022 at 14:31


Quote: Originally posted by Antiswat  

if you want concentrated NaClO, pool chlorinating agents usually react with NaOH to form concentrated NaClO


Does this work for the pool chlorinating agents based on TCCA and DCCA? Because I have lots of it, so I don't need to buy the whole store shelf of chlorine bleach.

And is the reaction basically instant or does it take some time?
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[*] posted on 25-5-2022 at 03:06


Quote: Originally posted by Linus1208  
Quote: Originally posted by Antiswat  

if you want concentrated NaClO, pool chlorinating agents usually react with NaOH to form concentrated NaClO


Does this work for the pool chlorinating agents based on TCCA and DCCA? Because I have lots of it, so I don't need to buy the whole store shelf of chlorine bleach.

And is the reaction basically instant or does it take some time?


Yes, you can use TCCA. Styrene practically does not react with chlorinating agents in alkaline and neutral pH. But in an acidic medium (hydrochloric acid or a mixture of sulfuric acid and sodium chloride), when heated, the reaction is very rapid and there are minutes and seconds. It is exothermic and reagents must be added in portions

The main product of the reaction of styrene chlorohydrin. With an excess of Chroloacetophenone and dichroloacetophenone.

You can use also sodium chlorate.

But for the synthesis of benzoic acid from styrene, other reagents are needed. Nitric acid, permanganates, chromates.

Also hydrogen peroxide with fe3O4 nanopatricles(can be prepared from feso4 fecl3 and naoh) if boiled with styrene gives benzlaldehyde


[Edited on 25-5-2022 by Hexabromobenzene]
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[*] posted on 29-5-2022 at 12:25


The synthesis of styrene oxide works great.

Quote: Originally posted by Keras  
You can synthesise phenethyl alcohol which is the main component of rose perfume.


Do you have any references to this synthesis in a lab environment?
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[*] posted on 30-5-2022 at 01:04


Quote: Originally posted by Fyndium  
The synthesis of styrene oxide works great.

Quote: Originally posted by Keras  
You can synthesise phenethyl alcohol which is the main component of rose perfume.


Do you have any references to this synthesis in a lab environment?


Yes, cf. attached PDF. Replace the cyclopentene with styrene and sodium perborate with sodium percarbonate.

I intend to try this next weekend. Will post a report.


Attachment: Hydroboration.pdf (1MB)
This file has been downloaded 50 times

[Edited on 30-5-2022 by Keras]
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[*] posted on 30-5-2022 at 03:05


I would be very glad if you'd post a report of your process. I looked up for this synthesis a long time ago, but sort of buried it due to not finding any lucrative material.
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[*] posted on 30-5-2022 at 03:06


Quote: Originally posted by Fyndium  
I would be very glad if you'd post a report of your process. I looked up for this synthesis a long time ago, but sort of buried it due to not finding any lucrative material.


I’ll keep you posted, pinkie promise :)
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[*] posted on 30-5-2022 at 04:53


The hydration of styrene gives 1-phenylethanol, which in addition to smelling nice, can easily be oxidized to acetophenone, which is used to provide cherry or almondlike fragrances. Perhaps more useful is that it's also a useful building block in organic chemistry(often being used for Grignard reactions) and a very promising catalyst for the decarboxylation of amino acids to their amines of 1 less carbon. These in turn are incredibly useful to a home chemist.
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[*] posted on 30-5-2022 at 05:07


Quote: Originally posted by Amos  
The hydration of styrene gives 1-phenylethanol…


That would require a simple addition with HBr (non-radical addition), followed by a SN with NaOH, no?
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[*] posted on 30-5-2022 at 05:38


Quote: Originally posted by Keras  
Quote: Originally posted by Amos  
The hydration of styrene gives 1-phenylethanol…


That would require a simple addition with HBr (non-radical addition), followed by a SN with NaOH, no?
No, just boiling in water with a catalytic amount of sulfuric acid.



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