| Pages:
1
2 |
Linus1208
Harmless
Posts: 43
Registered: 7-6-2021
Member Is Offline
|
|
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?
|
|
|
SplendidAcylation
Hazard to Others
Posts: 196
Registered: 28-10-2018
Location: Starving in some deep mystery
Member Is Offline
Mood: No one I think is in my tree.
|
|
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
|
|
|
Texium
|
Thread Moved
7-5-2022 at 07:56 |
DraconicAcid
International Hazard
Posts: 4278
Registered: 1-2-2013
Location: The tiniest college campus ever....
Member Is Offline
Mood: Semi-victorious.
|
|
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.
Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
|
|
|
Keras
National Hazard
Posts: 768
Registered: 20-8-2018
Location: (48, 2)
Member Is Offline
|
|
You can synthesise phenethyl alcohol which is the main component of rose perfume.
|
|
|
Mateo_swe
National Hazard
Posts: 505
Registered: 24-8-2019
Location: Within EU
Member Is Offline
|
|
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).
|
|
|
Fantasma4500
International Hazard
Posts: 1677
Registered: 12-12-2012
Location: Dysrope (aka europe)
Member Is Offline
Mood: dangerously practical
|
|
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.
|
|
|
SplendidAcylation
Hazard to Others
Posts: 196
Registered: 28-10-2018
Location: Starving in some deep mystery
Member Is Offline
Mood: No one I think is in my tree.
|
|
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]
|
|
|
Fantasma4500
International Hazard
Posts: 1677
Registered: 12-12-2012
Location: Dysrope (aka europe)
Member Is Offline
Mood: dangerously practical
|
|
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
|
|
|
karlos³
International Hazard
Posts: 1520
Registered: 10-1-2011
Location: yes!
Member Is Offline
Mood: oxazolidinic 8)
|
|
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.
verrückt und wissenschaftlich
|
|
|
Tsjerk
International Hazard
Posts: 3022
Registered: 20-4-2005
Location: Netherlands
Member Is Offline
Mood: Mood
|
|
| 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!
|
|
|
Fantasma4500
International Hazard
Posts: 1677
Registered: 12-12-2012
Location: Dysrope (aka europe)
Member Is Offline
Mood: dangerously practical
|
|
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
|
|
|
Tsjerk
International Hazard
Posts: 3022
Registered: 20-4-2005
Location: Netherlands
Member Is Offline
Mood: Mood
|
|
| 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.
|
|
|
Linus1208
Harmless
Posts: 43
Registered: 7-6-2021
Member Is Offline
|
|
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).
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.
|
|
|
Linus1208
Harmless
Posts: 43
Registered: 7-6-2021
Member Is Offline
|
|
| 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.
|
|
|
Fantasma4500
International Hazard
Posts: 1677
Registered: 12-12-2012
Location: Dysrope (aka europe)
Member Is Offline
Mood: dangerously practical
|
|
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
|
|
|
Hexabromobenzene
Hazard to Self
Posts: 96
Registered: 27-4-2021
Member Is Offline
|
|
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]
|
|
|
Linus1208
Harmless
Posts: 43
Registered: 7-6-2021
Member Is Offline
|
|
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?
|
|
|
Hexabromobenzene
Hazard to Self
Posts: 96
Registered: 27-4-2021
Member Is Offline
|
|
| Quote: Originally posted by Linus1208 |
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]
|
|
|
Fyndium
International Hazard
Posts: 1192
Registered: 12-7-2020
Location: Not in USA
Member Is Offline
|
|
The synthesis of styrene oxide works great.
Do you have any references to this synthesis in a lab environment?
|
|
|
Keras
National Hazard
Posts: 768
Registered: 20-8-2018
Location: (48, 2)
Member Is Offline
|
|
| Quote: Originally posted by Fyndium | The synthesis of styrene oxide works great.
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 209 times
[Edited on 30-5-2022 by Keras]
|
|
|
Fyndium
International Hazard
Posts: 1192
Registered: 12-7-2020
Location: Not in USA
Member Is Offline
|
|
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.
|
|
|
Keras
National Hazard
Posts: 768
Registered: 20-8-2018
Location: (48, 2)
Member Is Offline
|
|
| 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 
|
|
|
Amos
International Hazard
Posts: 1406
Registered: 25-3-2014
Location: Yes
Member Is Offline
Mood: No
|
|
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.
|
|
|
Keras
National Hazard
Posts: 768
Registered: 20-8-2018
Location: (48, 2)
Member Is Offline
|
|
That would require a simple addition with HBr (non-radical addition), followed by a SN with NaOH, no?
|
|
|
Texium
Administrator
Posts: 4508
Registered: 11-1-2014
Location: Salt Lake City
Member Is Offline
Mood: PhD candidate!
|
|
| Quote: Originally posted by Keras |
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.
|
|
|
| Pages:
1
2 |
![[*]](images/xpblue/default_icon.gif){kind=icon}
