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Author: Subject: Pathways to phenethyl alcohol
Assured Fish
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[*] posted on 29-5-2019 at 22:56


Quote: Originally posted by DraconicAcid  
Haven't people cracked polystyrene to get styrene on this very forum?

yeah: http://www.sciencemadness.org/talk/viewthread.php?tid=88675#...

Yup. Also UC235 made a video on it.
Although im pretty sure the process stinks to high heaven just based on the fact that polystyrene always contains other additives, someone could do it that way if they wish, as 350°C isn't too hard to reach with heating tape or a burner.
Id just pitty the fool who tried without a fumehood.




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Keras
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[*] posted on 30-5-2019 at 08:47


Quote: Originally posted by Assured Fish  
Yup. Also UC235 made a video on it.
Although im pretty sure the process stinks to high heaven just based on the fact that polystyrene always contains other additives, someone could do it that way if they wish, as 350°C isn't too hard to reach with heating tape or a burner.
Id just pitty the fool who tried without a fumehood.


350 °C could even be reached with a good heating mantle. But I’m surprised he didn't get more tar.

But using styrene to epoxide it (with peracetic acid) is more or less the same than using oxirane from the get go. It seems that oxirane can be produced in one step from ethylene by bubbling it in a strongly basic bleach solution. The hypochlorite oxidise the ethylene to 2-choloroethanol which is then dehydrated into oxirane by the base. Besides this reaction can be conducted around 0°C which would avoid the formation of oxirane gas. It’s hard to find a reference, but this Japanese patent seems to indicate so…
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CuReUS
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[*] posted on 30-5-2019 at 09:45


Quote: Originally posted by Assured Fish  
as 350°C isn't too hard to reach...
its more like 2000'C
Quote: Originally posted by Assured Fish  
H2SO4 working specifically on styrene oxide to produce the less substituted alcohol.
http://www.sciencemadness.org/talk/viewthread.php?tid=22421&...

the only way to make 2-phenylethanol from styrene oxide is with reducing agents like Pt,Pd,SAH,DIBAL-H and LiH -http://www.escience.cn/system/file?fileId=96971

using NaBH4-https://www.tandfonline.com/doi/abs/10.1080/0039791090307960...

but this route is cumbersome and goes against the OP's desire for an easy method
Quote: Originally posted by Keras  
But I’m surprised he didn't get more tar.
You wouldn't be if you had watched the video I sent you :P
Quote:
Besides this reaction can be conducted around 0°C which would avoid the formation of oxirane gas.
but you have to distill it later to get pure oxirane :D...

btw,I found a ref for the anti-markonikoff bromination of styrene :) -http://www.sciencemadness.org/talk/viewthread.php?tid=22421&...
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clearly_not_atara
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[*] posted on 30-5-2019 at 10:41


https://www.tandfonline.com/doi/abs/10.1080/00397911.2017.12...

Attachment: bhatt2017.pdf (658kB)
This file has been downloaded 31 times





[Edited on 04-20-1969 by clearly_not_atara]
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[*] posted on 30-5-2019 at 11:39


Quote: Originally posted by clearly_not_atara  
https://www.tandfonline.com/doi/abs/10.1080/00397911.2017.12...


Thanks a bunch for that! Serendipitously I had just ordered zinc powder with my latest batch of magnesium turnings. So I’ll be able to test that out next time I can put my hands on my glassware. Meanwhile I should find a way to get paraformaldehyde from the 40% formaldehyde solution I have.
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SWIM
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[*] posted on 30-5-2019 at 13:29


Styrene thinner is available in California in shops that sell fiberglass making materials.
I think it is used at times to thin the resin.

What I know for certain is it is on the shelf in cans at Tap Plastics in San Mateo, and since California has serious environmental regulations I would assume its available in most of the US.

I've seen it online too. It is 90% styrene monomer and $25 a quart from Fiber Glast Developments corp. (That's not a typo)
They are in Ohio.





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draculic acid69
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[*] posted on 30-5-2019 at 18:07


Diazotise phenethylamine with nano2 and HCl.its that simple.i think.
No need to fuck with etO.
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Assured Fish
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[*] posted on 30-5-2019 at 21:26


Quote: Originally posted by CuReUS  
Quote: Originally posted by Assured Fish  
as 350°C isn't too hard to reach...
its more like 2000'C


No, its more like 400*C : https://www.youtube.com/watch?v=6tEs7P6UUVQ
https://en.wikipedia.org/wiki/Depolymerization

Quote: Originally posted by CuReUS  

Quote: Originally posted by Assured Fish  
H2SO4 working specifically on styrene oxide to produce the less substituted alcohol.
http://www.sciencemadness.org/talk/viewthread.php?tid=22421&...

the only way to make 2-phenylethanol from styrene oxide is with reducing agents like Pt,Pd,SAH,DIBAL-H and LiH


Yea i should know better, im gonna put that down to a brain fart.

Well if anyone is interested, (which i don't think they are).
The styrene at my work is this stuff: https://www.amcsupplies.com.au/manuals/Styrene%20Monomer%20-...


20190531_090800[1].jpg - 2MB

Probably only available in australia and new zealand, but im sure other similar products are available elsewhere.
Apparently it has a hell of a lot more than one use, as it solvates a few other plastics like PVC.
Or its just used as a generic adhesive or in making ABS resins.
It should be available in virtually any westernized part of the world.
It just won't be the easiest to track down.




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Keras
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[*] posted on 31-5-2019 at 00:31


Quote: Originally posted by draculic acid69  
Diazotise phenethylamine with nano2 and HCl.its that simple.i think.
No need to fuck with etO.


I'd need to make phenethylamine first :p

I think I’ll try the zinc route first, seems challenging… although it takes a bit of time.

For styrene, I surmise it’s been registered in the European REACH directive annex XVII (can’t check out, the related website seems to be dead) and phased out in commercial products, to be replaced by the less noxious ethyltoluene/vinyltoluene, a bit the same way benzene has been replaced by toluene, which is not as carcinogenic.

Also this patent claims to make styrene out of toluene and methanol.

[Edited on 31-5-2019 by Keras]
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[*] posted on 31-5-2019 at 01:28


My advise:
"Dont trust to Indian or Iranian or even Chinese articles"
(unfortunately i did this mistake many times)

I have experience on making Phenethyl alcohol from Phenylacetic acid ester by Bouveault-Blanc reduction and this is easiest and cheapest method.

Suggested method for synthesis Phenylacetic acid is Willgerodt-Kindler reaction from Styrene.

I attach reaxys search of all possible way for synthesis Phenethyl alcohol

Attachment: Phenethyl alcohol.pdf (2.3MB)
This file has been downloaded 57 times



[Edited on 31-5-2019 by Waffles SS]




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[*] posted on 31-5-2019 at 03:42


Quote: Originally posted by Waffles SS  
My advise:
"Dont trust to Indian or Iranian or even Chinese articles"
(unfortunately i did this mistake many times)

I don't trust Chinese material in general :)
Quote: Originally posted by Waffles SS  

I have experience on making Phenethyl alcohol from Phenylacetic acid ester by Bouveault-Blanc reduction and this is easiest and cheapest method.

Suggested method for synthesis Phenylacetic acid is Willgerodt-Kindler reaction from Styrene.

I attach reaxys search of all possible way for synthesis Phenethyl alcohol

Thanks for that. I'm still amazed that most of these reactions proceed from something more complex and take out a moiety to form phenethyl alcohol, as if it was impossible to synthesise from simplier molecules.
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[*] posted on 31-5-2019 at 04:09


Why would you need to make phenethylamine just buy it off eBay or alibaba.by the time you buy phenylalanine and decarboxylation catalyst and work it up,or if your making it from phenethylbromide(unlikely) it can't possibly be cost effective to make it rather than buy it.
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clearly_not_atara
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[*] posted on 31-5-2019 at 08:47


Indian research is certainly suspect, except the best Indian universities. But the formation of benzylzinc reagents and the addition of benzylzinc to aldehydes are both multiply attested. Reaxys showed another version of this reaction that uses water as a solvent with catalytic CdCl2 and InCl3:

https://www.thieme-connect.com/products/ejournals/abstract/1...

There may be other versions that use BnBr instead of BnCl to generate the BnZnX, since the bromide is usually better for these reactions.




[Edited on 04-20-1969 by clearly_not_atara]
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CuReUS
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[*] posted on 1-6-2019 at 09:32


Quote: Originally posted by draculic acid69  
Why would you need to make phenethylamine just buy it off eBay or alibaba
In that case,the OP could just buy phenylethanol itself
Quote: Originally posted by Keras  

For styrene, I surmise it’s been registered in the European REACH directive annex XVII (can’t check out, the related website seems to be dead) and phased out in commercial products, to be replaced by the less noxious ethyltoluene/vinyltoluene, a bit the same way benzene has been replaced by toluene, which is not as carcinogenic.
If you can't buy it in from stores near you,you could order it online from one of the fibreglass companies
I suggest you get your hands on some styrene by hook or by crook because I just found a crazy reaction in waffle's reaxy search (pg 59 of pdf) -https://pubs.rsc.org/en/content/articlelanding/1982/p2/p2982... (they claim to convert styrene to PEA using H2SO4 in ethanol at RT in 56% yield :o )
You can't make it easier than that .
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Corrosive Joeseph
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[*] posted on 1-6-2019 at 09:41


Paper delivery........

https://pubs.rsc.org/en/content/articlelanding/1982/p2/p2982...


Ellis, G. W. L., & Johnson, C. D. (1982).
Kinetic acidity function H c. Part 3. Applicability to hydration of styrenes.
Journal of the Chemical Society, Perkin Transactions 2, (8), 1025.


/CJ

Attachment: ellis1982.pdf (332kB)
This file has been downloaded 38 times





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[*] posted on 1-6-2019 at 10:25


That D-glucose, oxygen in aq. phosphate buffer, Time=8h, T=30oC, Green chemistry, regioselective reaction also sounds interesting! :)

[Edited on 1-6-2019 by Pumukli]
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[*] posted on 2-6-2019 at 01:57


Could styrene be made reacting PhMgBr with vinyl chloride?
Also thanks for the papers!

[Edited on 2-6-2019 by Keras]
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Corrosive Joeseph
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[*] posted on 2-6-2019 at 03:30


No worries.

Easiest route to styrene monomer -
https://www.viral-surf.com/en/243-monomer-styrene-1-liter-52...

and phenethylamine -
https://www.bulksupplements.com/phenylethylamine-hcl.html



/CJ




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[*] posted on 2-6-2019 at 07:08


Thanks! The first company is in France, that will ease the process a lot! :)

Also, just as a side note, if you upload articles, which is very kind, try not letting the name of the uni on the margin. That could compromise you, and I'd be very unhappy about that.
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