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Author: Subject: Isopropyl alcohol and hydrogen peroxide
hkparker
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[*] posted on 28-5-2011 at 18:36
Isopropyl alcohol and hydrogen peroxide


A friend recently asked me what the reaction between isopropyl alcohol and hydrogen peroxide would be. I said either the alcohol would oxidize to an aldehyde then maybe a carboxylic acid, or an organic peroxide would form, but I cant be sure which (leaning more toward the nasty organic peroxide). He says he searched around the web and didn't find much, so I was wondering if anyone knew what would happen. I've been thinking about trying this experimentally in mg quantities.



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[*] posted on 28-5-2011 at 18:51


I don't think these will react appreciably without catalysis or maybe forcing conditions. But I could be wrong.
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[*] posted on 28-5-2011 at 21:09


Isopropyl alcohol is 2-propanol. It can't form a 3 carbon aldehyde or carboxylic acid. It might form acetone however, a ketone.



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[*] posted on 29-5-2011 at 09:09


Quote: Originally posted by Magpie  
Isopropyl alcohol is 2-propanol. It can't form a 3 carbon aldehyde or carboxylic acid. It might form acetone however, a ketone.


Ah, I'm sorry Magpie, I was copying from the oxidation path of ethanol, different story when there is another carbon there. Still a bit new in organic. Following that same mechanism though, I can see why ketone formation is likely. I will give it a try, I'm just still wondering about organic peroxides.




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[*] posted on 29-5-2011 at 09:34


Hey, don't worry about it. You're doing fantastic work for your young age.

There are several ways to prevent peroxides as discussed in this forum. I add BHT (butylated hydroxy toluene, IIRC). I put this in my diethyl ether and THF at ~200ppm.




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[*] posted on 29-5-2011 at 10:05


Thank you, I really appreciate it. I've read a bit about avoiding peroxides when I make ether, but unfortunately I don't have any BHT. I might still give this a try in such small quantities it doesn't matter, and see if I can smell some acetone being produces.



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[*] posted on 31-5-2011 at 17:13


If the reaction between IPA and hydrogen peroxide truly yields acetone than one should take care when doing the reaction, because an excess of hydrogen peroxide could react with the acetone forming acetone peroxide, which is highly explosive.

I don't think the reaction between acetone and hydrogen peroxide occurs expontaneously, but anyway, I would take care when doing it though.
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[*] posted on 31-5-2011 at 17:16


Thats a good point, though that reaction requires an acid catalyst. Also, TATP forms only at low temperature, otherwise the even more unstable (but less powerful) Diacetone Diperoxide forms.



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[*] posted on 1-6-2011 at 07:31


To be sure, do this reaction on a small scale! So half a mL of both reactants for example. You don't want acetone peroxide or CH3CH(OOH)CH3 to form, if this is possible. I'm sot sure.
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[*] posted on 1-6-2011 at 07:53


A quick Google shows a lot of alcohol oxidations using hydrogen peoxide but they seem to use transition metal catalysts, try "hydrogen peroxide alcohol oxidation".
Also hydrogen peroxide is a very weak nucleophile so I doubt it will form a hydroperoxide.
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[*] posted on 1-6-2011 at 08:35


Ill be trying it on a very small scale, thanks.

Thank you SS, your search did turn some results. I'll try this reaction uncatalyzed first then see where I can go from there.




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[*] posted on 3-6-2011 at 13:04


Quote: Originally posted by hkparker  
A friend recently asked me what the reaction between isopropyl alcohol and hydrogen peroxide would be. I said either the alcohol would oxidize to an aldehyde then maybe a carboxylic acid, or an organic peroxide would form, but I cant be sure which (leaning more toward the nasty organic peroxide). He says he searched around the web and didn't find much, so I was wondering if anyone knew what would happen. I've been thinking about trying this experimentally in mg quantities.

I find no info on isopropyl alcohol reacting w/ H2O2, there is
however, an oblique reference indicating that the combination
high strength H2O2 and IP may have explosive properties.

Byda 90% H2O2 and ethanol with 100 ppm Fe+++ catalyst yields (50% of theory) acetic acid.

ES Shanley & FP Greenspan
Highly Concentrated Hydrogen Peroxide [90%] :
Physical and Chemical Properties
Industrial and Engineering Chemistry 39 [12] 1536-43
December, 1947.


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[*] posted on 3-6-2011 at 16:25


The Google entry for this article:
http://pubs.acs.org/doi/abs/10.1021/j100339a051
hints that there is a way.

"Oxidation of 2-Propanol Using Hydrogen Peroxide in Place of Dioxygen. .... catalyst on the :"




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[*] posted on 3-6-2011 at 20:15
Interesting...


If you read the first part of this article you will notice that it mentions some researchers who studied the photochemical and thermal initiation of this reaction and cites both. If you can give me a direct link to the online article I might be able to get you the .pdf (alternatively, try the references section on this forum).

Radiation-induced oxidation of 2-propanol by hydrogen peroxide in aqueous solutions

Abstract:
The radiation-induced oxidation of 2-propanol by hydrogen peroxide in neutral deaerated aqueous solution has been investigated. 2-Propanol is oxidized to acetone, and hydrogen peroxide reduced in stoichiometrically equivalent high yields. The yields are independent of hydrogen peroxide concentration in the range 5 × 10−2 to 10−3 M and linearly dependent on alcohol concentration in the range 0.13 to 1.05 M. The reaction yields increased with decreasing dose rate.The results are explained by a chain mechanism in which initiation occurs via H-atom abstraction from 2-propanol to form either (CH3)2ĊOH (1) or CH3 CHOH ĊH2 (2). 1 reacts with H2O2 in a chain propagating reaction2 may abstract the α hydrogen from the parent alcoholor undergo bimolecular termination. A lower limit of 53 ± 101mole−1 s−1 is estimated for the rate constant for this radical conversion reaction.


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