hkparker
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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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"Nothing is too wonderful to be true if it be consistent with the laws of nature." -Michael Faraday
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bbartlog
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I don't think these will react appreciably without catalysis or maybe forcing conditions. But I could be wrong.
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Magpie
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Isopropyl alcohol is 2-propanol. It can't form a 3 carbon aldehyde or carboxylic acid. It might form acetone however, a ketone.
The single most important condition for a successful synthesis is good mixing - Nicodem
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hkparker
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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.
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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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"Nothing is too wonderful to be true if it be consistent with the laws of nature." -Michael Faraday
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Magpie
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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.
The single most important condition for a successful synthesis is good mixing - Nicodem
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hkparker
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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.
My YouTube Channel
"Nothing is too wonderful to be true if it be consistent with the laws of nature." -Michael Faraday
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simba
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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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hkparker
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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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"Nothing is too wonderful to be true if it be consistent with the laws of nature." -Michael Faraday
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Jor
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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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ScienceSquirrel
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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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hkparker
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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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"Nothing is too wonderful to be true if it be consistent with the laws of nature." -Michael Faraday
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The WiZard is In
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| 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.
djh
----
The explosion removed the windows,
the door and most of the chimney.
It was the sort of thing you expected in
the Street of Alchemists. The neighbours
preferred explosions, which were at least
identifiable and soon over. They were better
than the smells, which crept up on you.
Terry Pratchett
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Magpie
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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 :"
The single most important condition for a successful synthesis is good mixing - Nicodem
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MagicJigPipe
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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.
Attachment: Radiation-induced oxidation of 2-propanol by hydrogen peroxide in aqueous solutions.pdf (381kB)
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"There must be no barriers to freedom of inquiry ... There is no place for dogma in science. The scientist is free, and must be free to ask any
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makeaccount
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Verdict
Verdict=?
I mixed to create a sterile solution that would hopefully kill bacteria and viruses and other saty things. Does it? Or does it react into some
dangerous different thing?
(I just leave it in an open container @ room temp)
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AJKOER
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OK, H2O2 and transition metals, or H2O2 and radiation, are both paths to hydroxyl radical formation.
So the methods mentioned could actually be hydroxyl radical assisted paths. Interestingly, in place of H2O2 one can, at least theoretically in this
case, use air/O2 in the presence of an acid, the usual transition metal employed in this synthesis and a small amount of a reductant, like citrate or
ascorbate or a bit of both.
Theory also suggest employing HOCl, in place of H2O2, and an appropriate transition metal in an analogous Fenton-type reaction.
If the purpose is to disinfect, my recollection is that the paths I suggested are capable of so doing and likely the existing basis of disinfecting
sprays and the like.
[Edited on 5-3-2017 by AJKOER]
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Melgar
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Of course, H2O2 and isopropanol are both capable disinfectants on their own, so that would probably hold true of a mixture of the two as well. H2O2
could probably oxidize isopropanol into lactic, pyruvic, and acetic acid via radical pathways, which then might catalyze the formation of acetone
peroxides. Granted, this would take a long time, but it seems plausible enough to warrant not storing such a mixture.
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tsathoggua1
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Whilst it is rare and by no means anything like as much of a risk of it happening, I have read that it is possible for propan-2-ol to peroxidize in
storage to form an explosive organoperoxide. You might wish to be careful with deliberately adding H2O2 to iPA.
http://www.sigmaaldrich.com/chemistry/solvents/learning-cent...
Note that propan-2-ol is specifically mentioned, as being capable of forming explosive organoperoxides that in the case of iPA are 'significantly less
volatile than the solvent itself' and warns that evaporation and concentration can (as ethers are well known for when being stripped) increase the
concentration of the peroxide. And it also states that multiple openings of containers of 'most group B solvents' can result in 'significant and
dangerous peroxide concentration'
Although admittedly, the references I've heard to actual explosions from iPA perodizing (no, I do mean isopropanol, not diisopropyl ether, which is a
bugger, I prefer to keep the latter in sealed metal cans under pressure (indeed fractionation, after first testing for peroxidation, and doing it
under inert gas of diisopropyl ether-based car starting fluid is almost preferable, since that way the DIPE is kept out of reach of O2 and light, and
the metal can should provide transition metal ions to retard peroxidation should it not, similarly to keeping some copper wool or wire in EtOEt?
Of course it means fractionating from EtOEt and toluene, heptane and acetone is present also, although the acetone can be removed with H2O) but
diisopropyl ether is one of relatively few solvents that rather give me the willies
Quick question-EtOEt should be tested at least yearly, DIPE every 3 months minimum, how often should one ideally test THF?
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gaztonbidefranck
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Hello, i join this topic for my first reply on this forum.
So i have found this document how to produce hydrogen peroxide from isopropyl alcohol.
Attachment: burgess2007.pdf (678kB)
This file has been downloaded 738 times
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Alkoholvergiftung
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Isopropylalkohol and very deluted hydrogenperoxyd was used to produce hydrogenperoxyd and Aceton throught Reflux Destillation. They heat the mix to 75
C and the Alkohol breaks up into acetenon and H2O2 without the deluted hydrogenperoxyd it only breaks to Aceton and water.
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