Brominerain
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Isononyl alcohol
Having hydrolyzed DINP(Diisononyl phthalate) to make phthalic acid, I was left with a considerable amount of isononyl alcohol. Is there any use of
isononyl alcohol?
So I was wondering if it was possible to break some carbon-carbon bonds to make 1-pentanol and then use it to make amyl nitrite(I think it is used to
treat cyanide poisoning).
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j_sum1
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Make some interesting esters?
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DraconicAcid
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Oxidize it to the acid, and make another set of interesting esters?
Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
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Brominerain
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Is it possible to oxidize it with KMnO4?
Is there any other easier way?
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Pumukli
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I would try NaOCl first. :-)
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j_sum1
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While on the topic, ammonium nonanoate is used as a weedkiller: an alternative to glyphosphate. That may be a souce of nonanoic acid.
But I am still interested in the alcohol.
[Edited on 29-8-2022 by j_sum1]
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Brominerain
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Is household bleach suitable, or should I prepare some pure NaOCl?
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Tsjerk
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Alkaline KMnO4 at room temperature should do it. Just make an equimolar solution of KMnO4 and NaOH and slowly drip this into a suspension of the
alcohol, until the purple color doesn't disappear anymore.
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Brominerain
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But KMnO4 and NaOH react and make a green solution.
(It reduces to K2MnO4 in alkaline solutions)
[Edited on 29-8-2022 by Brominerain]
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Tsjerk
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Ah, yes, of course. You make the alcohol suspension alkaline.
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Brominerain
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Did a quick test and the KMnO4 reduces very slowly, even in very basic solutions.
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Pumukli
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Household bleach would do.
Search the paper which describes it, I used this method in menthol -> menthone transformation with good results.
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Fery
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Brominerain - the solubility of such long chain alcohol in water is very low (cca 0,1 g per 1 L), so the reaction rate with water solution of KMnO4 is
slow. Make an emulsion with as tiny particles as possible. The salt of nonanoic acid which is produced should act as a not much efficient (but better
than nothing) phase transfer catalyst as well as weak emulsifier too.
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Texium
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No, they do not. Yes you can reduce MnO4-
to MnO42- in alkaline solution, but it needs to be reduced BY something. Neither water nor hydroxide are sufficient reducing
agents, so permanganate is stable in alkaline solution. If you add a reducing agent such as an alcohol, then yes, you will see the color change to
green, and then to brown as MnO2 precipitates. But it doesn't just happen spontaneously with no reducing agent present.
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Texium
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Ok, I would like to correct my previous post. Permanganate is reduced to manganate by hydroxide (hydroxide in turn being oxidized to O2),
but it’s much slower than reduction by alcohols. I tested it out today and it took over an hour for the solution sitting at room temp to change from
purple to green. This reaction isn’t a concern when oxidizing alcohols with alkaline permanganate because the alcohols are oxidized much more
readily. Just use excess permanganate if you’re concerned.
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