| Pages:
1
2 |
TheNaKLaB
Hazard to Self
Posts: 51
Registered: 18-9-2011
Location: Australia
Member Is Offline
Mood: Elastic
|
|
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.
|
|
|
Chemistry Alchemist
Hazard to Others
Posts: 403
Registered: 2-8-2011
Location: Australia
Member Is Offline
Mood: No Mood
|
|
wasnt i the one who told u about this synthesis?
[Edited on 31-10-2011 by Chemistry Alchemist]
|
|
|
Takron
Harmless
Posts: 47
Registered: 19-5-2010
Member Is Offline
Mood: No Mood
|
|
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
|
|
|
Chemistry Alchemist
Hazard to Others
Posts: 403
Registered: 2-8-2011
Location: Australia
Member Is Offline
Mood: No Mood
|
|
what would be the best way to obtain naphthalene tetrachloride?
|
|
|
Takron
Harmless
Posts: 47
Registered: 19-5-2010
Member Is Offline
Mood: No Mood
|
|
Getting NTC
This?
|
|
|
TheNaKLaB
Hazard to Self
Posts: 51
Registered: 18-9-2011
Location: Australia
Member Is Offline
Mood: Elastic
|
|
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.
|
|
|
bfesser
Resident Wikipedian
Posts: 2114
Registered: 29-1-2008
Member Is Offline
Mood: No Mood
|
|
Your product would likely be present as dipotassium o-phthalate. Try filtering to remove MnO<sub>2</sub>, 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]
|
|
|
Squall181
Harmless
Posts: 46
Registered: 21-2-2011
Member Is Offline
Mood: No Mood
|
|
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.
|
|
|
TheNaKLaB
Hazard to Self
Posts: 51
Registered: 18-9-2011
Location: Australia
Member Is Offline
Mood: Elastic
|
|
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]
|
|
|
mnick12
Hazard to Others
Posts: 404
Registered: 30-12-2009
Location: In the lab w/ Dr. Evil
Member Is Offline
Mood: devious
|
|
Phthalic anhydride? You mean phthalic acid. Anhydrides cannot be precipitated from aqueous solutions.
|
|
|
Chemistry Alchemist
Hazard to Others
Posts: 403
Registered: 2-8-2011
Location: Australia
Member Is Offline
Mood: No Mood
|
|
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]
|
|
|
TheNaKLaB
Hazard to Self
Posts: 51
Registered: 18-9-2011
Location: Australia
Member Is Offline
Mood: Elastic
|
|
I accidentally wrote anhydride instead of acid. Besides that, what would be the equation?
|
|
|
Takron
Harmless
Posts: 47
Registered: 19-5-2010
Member Is Offline
Mood: No Mood
|
|
Yay, so my idea worked for the most part?
|
|
|
smuv
National Hazard
Posts: 842
Registered: 2-5-2007
Member Is Offline
Mood: Jingoistic
|
|
Another product worth considering:
http://www.orgsyn.org/orgsyn/prep.asp?prep=cv2p0523
[Edited on 11-1-2011 by smuv]
"Titanium tetrachloride…You sly temptress." --Walter Bishop
|
|
|
Takron
Harmless
Posts: 47
Registered: 19-5-2010
Member Is Offline
Mood: No Mood
|
|
What's that used for? I checked on it and all I found were tests for cholesterol and fatty acids.
|
|
|
Squall181
Harmless
Posts: 46
Registered: 21-2-2011
Member Is Offline
Mood: No Mood
|
|
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.
|
|
|
Chemistry Alchemist
Hazard to Others
Posts: 403
Registered: 2-8-2011
Location: Australia
Member Is Offline
Mood: No Mood
|
|
Also had a use t make phenolphthalein.
|
|
|
Chemistry Alchemist
Hazard to Others
Posts: 403
Registered: 2-8-2011
Location: Australia
Member Is Offline
Mood: No Mood
|
|
So what is teh chemical equasion for this? for just the oxidation of Naphthalene carrys out as the following
8 C<sub>10</sub>H<sub>8</sub> + 21 O<sub>2</sub> = 10
C<sub>8</sub>H<sub>6</sub>O<sub>4</sub> + 2 H<sub>2</sub>O
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?
|
|
|
TheNaKLaB
Hazard to Self
Posts: 51
Registered: 18-9-2011
Location: Australia
Member Is Offline
Mood: Elastic
|
|
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.
|
|
|
Chemistry Alchemist
Hazard to Others
Posts: 403
Registered: 2-8-2011
Location: Australia
Member Is Offline
Mood: No Mood
|
|
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 C<sub>10</sub>H<sub>8</sub> while if its unbalanced then the whole thing looks like this ? C<sub>10</sub>H<sub>8</sub>
Yeah, id like to know the reaction equation as well for it as well
|
|
|
TheNaKLaB
Hazard to Self
Posts: 51
Registered: 18-9-2011
Location: Australia
Member Is Offline
Mood: Elastic
|
|
Wait, sorry, that was a misunderstanding  I stuffed up aha!
What program do you use? 
|
|
|
Chemistry Alchemist
Hazard to Others
Posts: 403
Registered: 2-8-2011
Location: Australia
Member Is Offline
Mood: No Mood
|
|
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
|
|
|
Takron
Harmless
Posts: 47
Registered: 19-5-2010
Member Is Offline
Mood: No Mood
|
|
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  .
I'm actually going to be doing a video comming up here soon on polymers using Phthalic Anhydride.
|
|
|
scrambles
Harmless
Posts: 4
Registered: 20-10-2011
Member Is Offline
Mood: No Mood
|
|
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]
|
|
|
mr.crow
National Hazard
Posts: 884
Registered: 9-9-2009
Location: Canada
Member Is Offline
Mood: 0xFF
|
|
Ummm naphtha does not have naphthalene. If it did it would smell really bad and leave residues
Double, double toil and trouble; Fire burn, and caldron bubble
|
|
|
| Pages:
1
2 |
![[*]](images/xpblue/default_icon.gif){kind=icon}
