Jmap science
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How do I make Phenol from dichlorobenzene
I have a solution of sodium hydroxide in water and insoluble dichlorobenzene stirring together, I was thinking they did would forum 1,4 phenol.
There was a change in color, to yellow.
Is it working and if not how do I make phenol from paradichlorobenzene?
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DraconicAcid
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Most alkyl halides will react with hydroxide to give alcohols through nucleophilic substitution reactions. Aryl halides (such as chlorobenzene) will
not do this unless there are strongly electron-withdrawing groups on the aromatic ring (trinitrochlorobenzene will react with hydroxide to give sodium
pictrate, for example). If it's turning yellow, it's probably doing something, but I wouldn't hazard a guess as to what.
ETA: To get chlorobenzene to react with aqueous sodium hydroxide, you have to heat it under pressure to 300 oC, according to Brown and Foote's
Organic Chemistry 3rd Ed.
[Edited on 10-1-2014 by DraconicAcid]
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.
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plante1999
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Maybe potassium tert-butoxide in an fatty alcohol at high heat could remove the chlorine atoms.
I never asked for this.
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bfesser
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Thread Moved
9-1-2014 at 17:48 |
UnintentionalChaos
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ಠ_ಠ
1) It's called hydroquinone
2) It's not reacting because see DraconicAcid's post.
3) You can't make phenol from it (by any sane approach).
Department of Redundancy Department - Now with paperwork!
'In organic synthesis, we call decomposition products "crap", however this is not a IUPAC approved nomenclature.' -Nicodem
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Metacelsus
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Hypothesis: You could react with ammonia to form 1,4-diaminobenzene, react with hydrogen peroxide to form quinone, and then reduce the quinone.
Alternatively (and an easier, though more hazardous process), you could melt it with KOH.
http://ir.uiowa.edu/cgi/viewcontent.cgi?article=4111&con...
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leu
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At least one of the chlorine atoms would have to be removed via reductive dehalogenation which according to Houben-Weyl is rather difficult  As this chemical process is needed for hazardous waste disposal there have been many
articles published on the subject  Six such documents are in the attached zip
file  Phenol used to be made by hydrolysis of chlorobenzene using the
Raschig-Hooker process:
http://en.wikipedia.org/wiki/Raschig%E2%80%93Hooker_process
as has been stated already it's not a cost effective or practical route 
Attachment: Dechlorination.zip (866kB)
This file has been downloaded 303 times
Chemistry is our Covalent Bond
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Jmap science
Yet another ID of SimpleChemist-238
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Is there any way to make benzene from it or any useful compounds from it?
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BromicAcid
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Dechlorinating Dichlorobenzene
https://www.sciencemadness.org/whisper/viewthread.php?tid=17...
BTW UnintentionalChaos, I prefer benzene-1,4-diol over hydroquinone... there are only so many trivial names I can remember
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leu
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| Quote: | | Is there any way to make benzene from it or any useful compounds from it? |
You would learn a lot more effectively by researching and reading published literature than you ever will by posting questions The ACS overview mentioned in the linked thread by bbartlog is attached
Attachment: ie50218a006.pdf (329kB)
This file has been downloaded 632 times
Chemistry is our Covalent Bond
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