The Vespiary

The Hive => Chemistry Discourse => Topic started by: Elementary on June 18, 2002, 01:43:00 PM

Title: Styrene Epoxidation
Post by: Elementary on June 18, 2002, 01:43:00 PM
As many of you bees might of gathered swim is kinda obsessed with phenylacetic and P2P routes.
Well my new couse of study is the conversion of styrene (easy to get) to phenylacetaldehyde via the intermediate styrene oxide.

On investigating the conversion of styrene to styrene oxide I have come up against epoxidation for the first time.

So diving into my text books I found, that peroxybenzoic acid is used for the conversion of styrene to styrene oxide. After seeing the word "Epoxide" I went straight over to Rhodiums site and I was bombarded with epoxations being used with safrol.

As a newbee to expoxation can anybees tell me what other reagents could possibly be used for making styrene oxide, as I am finding all this information a bit overwhelming ?


John Lennon - Working Class Hero
Title: Most useful kinds of laboratory-scale ...
Post by: Rhodium on June 18, 2002, 01:48:00 PM
Most useful kinds of laboratory-scale epoxidations can be found on my page in one form or another.

Search

http://www.scirus.com (http://www.scirus.com)

for "styrene oxide synthesis" - you'll find every possible method there.
Title: :-
Post by: Elementary on June 18, 2002, 01:51:00 PM
So if they work with safrol, can I safely say that they will work with styrene ?
John Lennon - Working Class Hero
Title: Yes.
Post by: Rhodium on June 18, 2002, 01:55:00 PM
Yes.
Title: Thanks
Post by: Elementary on June 18, 2002, 02:01:00 PM
Thank-you

And thanks for that link as well  :)
John Lennon - Working Class Hero
Title: Don't forget Post 290189 Post 299539
Post by: PolytheneSam on June 18, 2002, 04:53:00 PM
Don't forget 

Post 290189 (missing)

(PolytheneSam: "polystyrene", Chemistry Discourse)

Post 299539 (missing)

(PolytheneSam: "phenylacetaldehyde oxidation", Chemistry Discourse)
http://www.geocities.com/dritte123/PSPF.html
The hardest thing to explain is the obvious
Title: Hi,I dont know if this helps at all.
Post by: ballzofsteel on June 18, 2002, 05:44:00 PM
Hi,I dont know if this helps at all.
I came across it yesterday.Biodegredation pathways.
Styrene oxide -->phenylacetaldehyde via enzyme

http://umbbd.ahc.umn.edu:8015/umbbd/servlet/pageservlet?ptype=p&pathway_abbr=sty (http://umbbd.ahc.umn.edu:8015/umbbd/servlet/pageservlet?ptype=p&pathway_abbr=sty)



oops,sorry, cant get the link to work.Interestng site though

http://umbbd.ahc.umn.edu/ (http://umbbd.ahc.umn.edu/)

front page
Title: dimethylstyrene & ozone
Post by: hellman on June 18, 2002, 05:51:00 PM
Read some stuff on "ozoneing" Methyl styrenes,.

Upon ozoning say dimethylstyrene, your two products are funny enough Acetone, and benzaldehyde,

Sounds interesting, Doesn't it :o
Title: Alcohol Wacker with Pd(NO3)2 if I remember ...
Post by: Osmium on June 19, 2002, 01:59:00 AM
Alcohol Wacker with Pd(NO3)2 if I remember correctly will produce the phenylacetaldehyde.
I'm not fat just horizontally disproportionate.
Title: Epoxide synthesis
Post by: Cyrax on July 14, 2002, 05:01:00 PM
Check out Org. Synth. for the synthesis of styrene oxide:

http://www.orgsyn.org/orgsyn/prep.asp?prep=cv1p0494 (http://www.orgsyn.org/orgsyn/prep.asp?prep=cv1p0494)



There is described a more ingenious way to make this phenyloxirane in Vogel's Textbook of practical organic chemistry 5th ed., p 1132: they react benzaldehyde with trimethylsulphonium iodide under PTC