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Author: Subject: Oxidizing Naphthalene to Phthalic anhydride
TheNaKLaB
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[*] posted on 30-10-2011 at 23:47
Oxidizing Naphthalene to Phthalic anhydride


I was reading up about Naphthalene about some properties and I found out that it can be oxidized to Phthalic anhydride.

"Oxidation with chromate or permanganate, or catalytic oxidation with O2 and a vanadium catalyst, gives phthalic acid"

I found this information on Wikipedia.

Would there be some way to directly oxidize the Naphthalene to Phthalic anhydride using Potassium Permanganate? Would there be a sensible method for oxidizing it? Eg, melting the Naphthalene with Potassium Permanganate.







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[*] posted on 31-10-2011 at 10:15


wasnt i the one who told u about this synthesis?

[Edited on 31-10-2011 by Chemistry Alchemist]




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[*] posted on 31-10-2011 at 10:24


The way I would start is to dissolve a stoich. amount of both chems in water. The Naphthalene is only very slightly soluble in the water but I would venture a guess that as you reflux the mix, the naphthalene would react and then more naphthalene would dissolve into the water.

But I did some poking and found this.
''Manufacturing methods in the nineteenth century included oxidation of naphthalene tetrachloride with nitric acid, or, better, oxidation of the hydrocarbon with fuming sulfuric acid, using mercury or mercury(II) sulfate as a catalyst."

Also this -> Patent
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[*] posted on 31-10-2011 at 11:02


what would be the best way to obtain naphthalene tetrachloride?



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Takron
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[*] posted on 31-10-2011 at 12:48
Getting NTC


Quote: Originally posted by Chemistry Alchemist  
what would be the best way to obtain naphthalene tetrachloride?


This?
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TheNaKLaB
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[*] posted on 31-10-2011 at 13:49


I dissolved some Potassium Permanganate in water, then added some Naphthalene and boiled it until the Naphthalene melted. I heated the Naphthalene and Potassium Permanganate solution for about 20 minutes. After the solution cooled, the Potassium Permanganate changed a darker red/brown rather than the Purple it normally is. It also settled to the bottom of the beaker. I still have yet to check if there's any Phthalic anhydride by drying out the Potassium Permanganate precipitate/settlement and heat it until the Phthalic anhydride sublimes.



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[*] posted on 31-10-2011 at 13:59


Your product would likely be present as dipotassium o-phthalate. Try filtering to remove MnO2, acidify, filter, dry, then sublime the acid to the anhydride.

[edited to remove typos caused by the damn cat laying on the keyboard]

[Edited on 10/31/11 by bfesser]




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[*] posted on 31-10-2011 at 17:17


Yes Please let us know if you can precipitate phthalic acid from your solution by acidifying.

If this works this would be a much easier than having to boil boxes of vinyl gloves to extract Bis(2-ethylhexyl)phthalate.
If I can find some moth balls I will give this a try this weekend and report.
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TheNaKLaB
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[*] posted on 31-10-2011 at 18:05


I think I might have some success! The Potassium Permanganate seemed to react with the Naphthalene, because I have quite a bit of Manganese Dioxide that precipitated.

The Phthalic acid should precipitate when I acidify it, right?

I'll definitely be making a video on the process (If it actually ends up working).


Lastly, does anyone know the equation for reacting Naphthalene with Potassium Permanganate to Dipotassium Phthalate?

[Edited on 19-09-2011 by TheNaKLaB]




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[*] posted on 31-10-2011 at 18:52


Phthalic anhydride? You mean phthalic acid. Anhydrides cannot be precipitated from aqueous solutions.
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[*] posted on 31-10-2011 at 20:05


The procedure doesn't creat phthalic anhydride, you need other steps to obtain. The product, when naphthalene is oxidized it will make dipotassium o-phthalate and manganese dioxide which needs to be filtered. The dipotassium o-phthalate then needs to be acidified to precipitate phthalic acid and potassium salt which needs to be filtered and washed, you the. Need to dehydrate the acid to the anhydrous state and collect the needle like crystals, this is the synthesis I've been trying to work out for the last 3 months for my first organic synthesis, looks like I'll need to find a new one

[Edited on 1-11-2011 by Chemistry Alchemist]




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[*] posted on 31-10-2011 at 20:16


I accidentally wrote anhydride instead of acid. Besides that, what would be the equation?



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[*] posted on 31-10-2011 at 20:21


Yay, so my idea worked for the most part?



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[*] posted on 31-10-2011 at 20:45


Another product worth considering:
http://www.orgsyn.org/orgsyn/prep.asp?prep=cv2p0523

[Edited on 11-1-2011 by smuv]




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[*] posted on 1-11-2011 at 10:26


What's that used for? I checked on it and all I found were tests for cholesterol and fatty acids.



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[*] posted on 1-11-2011 at 16:27


Well lately it has been getting a lot of attention because it is used in Nurdrage's synthesis of Luminol, at least that's what I think.
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[*] posted on 1-11-2011 at 17:04


Also had a use t make phenolphthalein.



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[*] posted on 1-11-2011 at 17:28


So what is teh chemical equasion for this? for just the oxidation of Naphthalene carrys out as the following
8 C10H8 + 21 O2 = 10 C8H6O4 + 2 H2O

But with teh added potassium permanganate, what is actually happening here? i tryed for ages to figure it out but my results always came out negitive... anyone know?




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[*] posted on 1-11-2011 at 18:22


That equation is unbalanced, but that's the basic idea for the reaction?

I need to find out the reaction equation for the oxidation of Naphthalene and Potassium Permanganate.




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[*] posted on 1-11-2011 at 19:24


U sure its unbalanced? i use a program where you type in ur equation and if its balanced then it comes out Like this 8 C10H8 while if its unbalanced then the whole thing looks like this ? C10H8

Yeah, id like to know the reaction equation as well for it as well




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[*] posted on 1-11-2011 at 19:50


Wait, sorry, that was a misunderstanding :D I stuffed up aha!

What program do you use? :)





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[*] posted on 1-11-2011 at 20:18


Thats kk :) i tryed to use teh program to work out the Potassium Permanganate and Naphthalene but couldnt work it out... I use EBAS, its a program that calculates how much of each chemical you need for a reaction... its really good, but its a trail version, the one the trial is up you can still use it but the data base has been cut down so you need to keep typing in the formula instead of searching for it...

http://www.chembuddy.com/?left=EBAS&right=buy

I havent came across a patch for it yet so thhe only way to get full version is buying




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[*] posted on 1-11-2011 at 22:16


Quote: Originally posted by Squall181  
Well lately it has been getting a lot of attention because it is used in Nurdrage's synthesis of Luminol, at least that's what I think.


I was speaking about smuv's other product worth considering. I'm well aware of Phthalic Anhydride's popularity as of late :P.

I'm actually going to be doing a video comming up here soon on polymers using Phthalic Anhydride.




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[*] posted on 2-11-2011 at 18:07


permanganate would probably be the best option. you can buy the stuff at Sears (tm).

EDIT: Someone find out how to isolate napthalene from vm&p naphtha.

[Edited on 3-11-2011 by scrambles]
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[*] posted on 2-11-2011 at 19:11


Ummm naphtha does not have naphthalene. If it did it would smell really bad and leave residues



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