Sciencemadness Discussion Board
Not logged in [Login - Register]
Go To Bottom

Printable Version  
Author: Subject: Oxidation of Isopropanol
Megak
Harmless
*




Posts: 12
Registered: 8-12-2011
Member Is Offline


[*] posted on 8-12-2011 at 20:31
Oxidation of Isopropanol


Hey everyone:D

I was thinking about this today and was wondering what reaction is the production of acetone. I'm looking more for the science of it, I'm uninterested really in efficiency. So, I presume that

(CH3)2CHOH (l) + NaClO (l) -> (CH3)2CO

I doubt NaClO is an efficient oxidizer, but it's the first one off the top of my head. I also believe that this reaction wouldn't occur without a catalyst, though I don't know what that catalyst is.

Any thoughts?
View user's profile View All Posts By User
ThatchemistKid
Hazard to Others
***




Posts: 132
Registered: 2-6-2010
Member Is Offline

Mood: Hypergolic

[*] posted on 8-12-2011 at 22:27


You will get oxidation of the alcohol to acetone with that reaction but it will not stop there you will then form chloroform and sodium acetate. It is called a haloform reaction.
View user's profile View All Posts By User
blogfast25
International Hazard
*****




Posts: 5861
Registered: 3-2-2008
Location: Old Blighty
Member Is Offline


[*] posted on 9-12-2011 at 06:04


Quote: Originally posted by Megak  
Hey everyone:D

I was thinking about this today and was wondering what reaction is the production of acetone. I'm looking more for the science of it, I'm uninterested really in efficiency. So, I presume that

(CH3)2CHOH (l) + NaClO (l) -> (CH3)2CO

I doubt NaClO is an efficient oxidizer, but it's the first one off the top of my head. I also believe that this reaction wouldn't occur without a catalyst, though I don't know what that catalyst is.

Any thoughts?


Secondary alcohols can be oxidised to ketones by means of potassium dichromate (possibly also potassium permanganate): IPA to acetone, for instance. But that's not the industrial method of producing propanone...

A bit of background:

http://www.chemguide.co.uk/organicprops/alcohols/oxidation.h...

[Edited on 9-12-2011 by blogfast25]




View user's profile Visit user's homepage View All Posts By User
JibbyDee
Harmless
*




Posts: 38
Registered: 25-11-2011
Member Is Offline


[*] posted on 10-12-2011 at 14:48


Yeah this is an easy method of producing chloroform. I'd opt for permanganate as the oxidizer instead. If your aim is to explore simple organic reactions like this then you might as well go ahead and test out the ClO oxidation of IPA. Chloroform is a very useful solvent so knowing how to produce it is a good skill for the home chemist. Haven't actually made any myself, but once I get some decent reagent bottles to store the chloroform in, I'm going to try this reaction. I distilled about a 500 mL of dichloromethane last year for my lab but I stored it in a glass canning jar and a few weeks later when I went to get some of it, it was gone lol. Solvents like these get through the tiniest gaps so you really need proper containers to store them in. In some oxidation reactions (such as the permanganate oxidation of ethanol to produce acetaldehyde and ultimately acetic acid) you can distill the product before it is further oxidized into the next compound, maybe you can distill off the acetone before it is further oxidized into chloroform. IPA has a boiling point of around 80C whereas acetone has a BP of around 60C.

[Edited on 10-12-2011 by JibbyDee]
View user's profile View All Posts By User
Megak
Harmless
*




Posts: 12
Registered: 8-12-2011
Member Is Offline


[*] posted on 11-12-2011 at 11:18


Quote: Originally posted by JibbyDee  
Yeah this is an easy method of producing chloroform. I'd opt for permanganate as the oxidizer instead. If your aim is to explore simple organic reactions like this then you might as well go ahead and test out the ClO oxidation of IPA. Chloroform is a very useful solvent so knowing how to produce it is a good skill for the home chemist. Haven't actually made any myself, but once I get some decent reagent bottles to store the chloroform in, I'm going to try this reaction. I distilled about a 500 mL of dichloromethane last year for my lab but I stored it in a glass canning jar and a few weeks later when I went to get some of it, it was gone lol. Solvents like these get through the tiniest gaps so you really need proper containers to store them in. In some oxidation reactions (such as the permanganate oxidation of ethanol to produce acetaldehyde and ultimately acetic acid) you can distill the product before it is further oxidized into the next compound, maybe you can distill off the acetone before it is further oxidized into chloroform. IPA has a boiling point of around 80C whereas acetone has a BP of around 60C.

[Edited on 10-12-2011 by JibbyDee]


Hmm..... I was thinking about this and if I added the NaClO slowly and have the IPA in excess instead, I should limit my chloroform production, and even then i can pump it into an ice bath to condense it.

Though, I think if you want chloroform, just go straight with acetone and bleach, you'll get better yields. And from what I remember about chloroform, i think you can stop some of the evaporation by putting it in cotton balls
View user's profile View All Posts By User
Megak
Harmless
*




Posts: 12
Registered: 8-12-2011
Member Is Offline


[*] posted on 12-12-2011 at 11:58


So, I did try this and I didn't play around with it much, but after heating the mix up, I did notice some chloroform mixed with water.

Where from there? I have no idea

EDIT: Ok, so I think I know what has happened. My solution has oxidized a great amount (completely colorless) after some time. When I burned the solution off, I burned off the alcohol and acetone, bleach remained with chloroform. That's why it smelled sweet, I think

[Edited on 12-12-2011 by Megak]
View user's profile View All Posts By User
Waffles SS
International Hazard
*****




Posts: 584
Registered: 7-12-2009
Location: My Home
Member Is Offline

Mood: At Room Temperature

[*] posted on 20-2-2012 at 21:35


Quote: Originally posted by blogfast25  


Secondary alcohols can be oxidised to ketones by means of potassium dichromate (possibly also potassium permanganate): IPA to acetone, for instance. But that's not the industrial method of producing propanone...

A bit of background:

http://www.chemguide.co.uk/organicprops/alcohols/oxidation.h...

[Edited on 9-12-2011 by blogfast25]


How much potassium or sodium dichromate or Potassium permanganate is needed for oxidation 1 lit of Isopropanol to acetone?( i like to try it)
I think passing Isopropanol from Hot Copper Tube is also possible route for oxidation of Isopropanol to acetone

[Edited on 21-2-2012 by Waffles SS]
View user's profile View All Posts By User

  Go To Top