Waffles SS
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Chlorotoluene
What is easier and best method for chlorination of Toluene?
[Edited on 16-6-2011 by Waffles SS]
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entropy51
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Diazotization and Sandmeyer using CuCl performed on the appropriate isomer of toluidine. Dissolving metal reduction with Fe/HCl on the appropriate
chloronitrobenzene will also work, but I prefer the Sandmeyer route.
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Nicodem
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Thread Moved
16-6-2011 at 10:30 |
gsd
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Browse these threads:
http://www.sciencemadness.org/talk/viewthread.php?tid=11698&...
http://www.sciencemadness.org/talk/viewthread.php?tid=13196&...
gsd
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Waffles SS
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Thanks but i am looking for chlorination not Diazotization.
I am looking for easier method of toluene chlorination
I think simple bubbling a chlorine gas in toluene (with some acetic acid) lead to chlorotoluene but i think the temp and time of reaction is very
important(higher temp may lead to dichloro toluene)
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gsd
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Quote: Originally posted by Waffles SS  | Thanks but i am looking for chlorination not Diazotization.
I am looking for easier method of toluene chlorination
I think simple bubbling a chlorine gas in toluene (with some acetic acid) lead to chlorotoluene but i think the temp and time of reaction is very
important(higher temp may lead to dichloro toluene) |
Please quote a reference.
AFAIK direct chlorination of toluene leads to substitution in side chain not nucleus.
gsd
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Waffles SS
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Dear gsd,
Thanks but your first link cause error and seems doesnt exist "The item you requested could not be found."
and your second link contain lot of patent and link and i dont know which one is about chlorotoluene
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gsd
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@ WSS
look for the post which gives "Attachment: Preparation of o-Chlorotoluene.pdf (85kB)
This file has been downloaded 9 times"
This link still worked fine for me.
In the second link, look for DJF90's post "Attachment: Oxidising chlorination of toluene.pdf (231kB)
This file has been downloaded 19 times"
gsd
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Waffles SS
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Dear gsd,
There is no djf90 post on second link
Second link is"Wanted References and Needed Translations(6)" page 5
and first link is"Wanted References and Needed Translations (5)" that cause error
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Waffles SS
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| Quote: Originally posted by gsd |
Please quote a reference.
AFAIK direct chlorination of toluene leads to substitution in side chain not nucleus.
gsd |
| Quote: |
Chlorination of toluene with chlorine without catalyst requires a polar solvent as well such as acetic acid. The ortho to para selectivity is low
J. L. O'Connell, J. S. Simpson, P. G. Dumanski, G. W. Simpson and C. J. Easton (2006). "Aromatic chlorination of ω-phenylalkylamines and
ω-phenylalkylamides in carbon tetrachloride and α,α,α-trifluorotoluene"
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gsd
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check DJF90 post in Wanted References and Needed Translations(6) page 5
you can also utfse to locate the post given names of poster and article.
gsd
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redox
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When you do this reaction, you may want to keep light out of the reaction vessel, as the free radical chlorines would react to form benzyl chloride.
My quite small but growing Youtube Channel: http://www.youtube.com/user/RealChemLabs
Newest video: Synthesis of Chloroform
The difference between chemists and chemical engineers: Chemists use test tubes, chemical engineers use buckets. |
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not_important
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Note that the reference with acetic acid is using glacial acetic acid as a solvent/diluent.
Old school method is to use a Lewis acid catalyst when the aromatic nucleus is not strongly activated. Plenty of examples of that around, in most
practical org synth lab books since 1890 or so.
All of these methods will give a mixture of o-, p-, and often m- haloaromatics, plus not uncommonly a small amount of polyhalogenated material. If
you want a specific isomer then the diazotization and Sandmeyer reaction on the proper toluidene is a much better route; again old trad org synth.
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Waffles SS
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Thank Dear Not_important,I am so happy to see your post again
The price of final product is very important for me,my final goal is preparing cheap M-cresol. i want to chlorination of toluene(0.6$/kg) to Para and
ortho isomer and then separate para isomer.after that i will hydroxylation of Para-chlorotoluene to M-cresol and P-cresol.I think toluidine is much
more expensive that my final product by this method.
Preparation of chlorotoluene by oxidizing chlorination of toluene
http://www.sciencemadness.org/talk/files.php?pid=213135&...
[Edited on 18-6-2011 by Waffles SS]
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Kemoterapia
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I can't access to this link?
http://www.sciencemadness.org/talk/files.php?pid=213135&...
Somebody can reupload the file or give an alternative link?
Thanks in advance 
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Waffles SS
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Attachment: Preparation of chlorotoluene by oxidizing chlorination of toluene.pdf (231kB)
This file has been downloaded 507 times
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Kemoterapia
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Thanks a lot WafflesSS! Is exactly the paper from Neftekhemiye that I was looking for.
I post this yesterday in late night and after few hours I get the answer.
Have a nice day!
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