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Author: Subject: Beginer benzene synthesis (No hydroxide)
plante1999
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[*] posted on 28-6-2011 at 18:28
Beginer benzene synthesis (No hydroxide)


I am very beginner in organic chemistry , but I need benzene as a solvent in a inorganic chemistry synthesis.

I have buy 100 g of sodium benzoate at the pharmacy at 6.50 $ CAN. I have use 50g of it to make 37g of Benzoic acid. I make some test without very high success to make benzene so now I have as a source of benzene ring:

35g benzoic acid

38g sodium benzoate

I need to make about 5ml of benzene for the reaction , but i want to store about 25ml of it.

I could not use Hydroxide because i dont have any (In fact I have green drano that only work well for extration of chromium , lead and extraction of metal from oxide in general because it contain a huge amont of NaNO3 , Now I look like a beginer to chemistry , I know , but in fact I generaly use ammonia as a source of hydroxide in inorganic synthesis so....)

If possible I want to use an acid for making it , I could use Carbonate. I have an very huge variety of inorganic acid (including 30% HF and 30% H2TiCl6) but I am limited in organic acid .... I have:

2L of 10% vinegar (very impure acetic acid)
2g of citric acid
10g of oxalic acid , i can get 30g for 5$ Can at the pharmacy (I can buy almost anything I want at the pharmacy , I have already buy 50g of sodium permangate....)
37g of benzoic acid (this is the lab grade chemical that i have the most number of grams ( in fact from wath i know in organic chemistry , i need an huge ammont of chemical for a small ammont of product )


Thanks!!!



[Edited on 29-6-2011 by plante1999]




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theflickkk
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[*] posted on 28-6-2011 at 20:59


Calcium oxide in place of sodium hydroxide works too if I'm not mistaken
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[*] posted on 29-6-2011 at 03:14


You can buy builder's lime in 25kg bags that is Ca(OH)2. It works with sodium benzoate, also you don't need to make benzoic acid from sodium benzoate to make benzene, it's just wasting reagents.
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testimento
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[*] posted on 10-2-2014 at 19:22


What would be the balanced reaction with calcium oxide or calcium hydroxide?

With sodium hydroxide it stands: sodium benzoate + NaOH = Na2CO3 + benzene
With calcium hydroxide it stands: (moles of?)sodium benzoate + Ca(OH)2 = ? (would it be CaCO3 + benzene + water?)
With calcium oxide it stands: ???
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[*] posted on 10-2-2014 at 19:47


CaO +C6H5CO2H -> CaCO3 +C6H6, basically.



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[*] posted on 11-2-2014 at 04:12


It's called decarboxylation. Learn about functional group reactions, aromatics and aliphatic series and you will go far into organic chem very fast.
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[*] posted on 11-2-2014 at 05:02


If I were you, reflux toluene with AlCl3 anhydrous. This makes benzene and mesitylene.
3C6H5CH3 =AlCl3=> 2C6H6 + C6H3(CH3)3

[Edited on 2-11-2014 by TheChemiKid]

[Edited on 2-11-2014 by TheChemiKid]




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[*] posted on 11-2-2014 at 09:13


Quote: Originally posted by TheChemiKid  
If I were you, reflux toluene with AlCl3 anhydrous.


Would you really? Anh. AlCl3 is hard to prepare.




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[*] posted on 11-2-2014 at 12:50


Pass dried Chlorine through a flask with Aluminum in it.
2Al+3Cl2 ==> 2AlCl3

[Edited on 2-11-2014 by TheChemiKid]




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[*] posted on 11-2-2014 at 13:02


Stuffing a metal tube with aluminum and heating it while passing a stream of previously dried chlorine through it is a better way. You need absolutely dry Cl as well as a way to condense the AlCl3 on the other end. There is a good post on a thread somewhere here where somebody uses this set up and heats the metal reaction tube on a BBQ. There are also reported methods using Al powder under DCM and bubbling Cl through that, although I would be interested to hear about the yields crone members who have attempted it with success!
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[*] posted on 11-2-2014 at 13:20


@TheChemiKid and Mailinmypocket:

Everybody knows that, although dry HCl also works and would be less hazardous than Cl2.

But from general 'textbook' knowledge to actual successful execution is a big step in an amateur setting, for this kind of thing.

There's also a lab scale method from Al + DCM + I<sub>2</sub>, far more realistic at amateur level:

Post by 'rrkss', see the pdf attachment:

http://www.sciencemadness.org/talk/viewthread.php?tid=14111&...

The method of direct chlorination of Al powder with anh. HCl in DCM at RT, as tried extensively by 'peach', was a failure as far as I'm concerned.

[Edited on 11-2-2014 by blogfast25]




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[*] posted on 11-2-2014 at 14:39


Just generate some Cl2 or HCl gas, lead it through CaCl2 trap and pass it over aluminium flakes heated over 400C, AlCl3 will sublime at the other end of the tube. More hardcore chemists will smelt aluminium and carefully bubble Cl2 gas into it and lead the condensate out of the reactor. Slight moisture, in PPM scale doesn't matter because this is not analytic nuclear chemistry, but amateur.
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[*] posted on 11-2-2014 at 15:03


Quote: Originally posted by blogfast25  

The method of direct chlorination of Al powder with anh. HCl in DCM at RT, as tried extensively by 'peach', was a failure as far as I'm concerned.


I got anhydrous Cl2 to work in DCM but the procedure needs some fine tuning.




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[*] posted on 12-2-2014 at 06:32


Quote: Originally posted by UnintentionalChaos  
I got anhydrous Cl2 to work in DCM but the procedure needs some fine tuning.


Really? Did you experience an exotherm at least?




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