Sciencemadness Discussion Board

Isononyl alcohol

Brominerain - 28-8-2022 at 00:33

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).

j_sum1 - 28-8-2022 at 01:30

Make some interesting esters?

DraconicAcid - 28-8-2022 at 10:17

Oxidize it to the acid, and make another set of interesting esters?

Brominerain - 29-8-2022 at 03:43

Is it possible to oxidize it with KMnO4?
Is there any other easier way?

Pumukli - 29-8-2022 at 04:10

I would try NaOCl first. :-)

j_sum1 - 29-8-2022 at 04:27

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]

Brominerain - 29-8-2022 at 04:38

Quote: Originally posted by Pumukli  
I would try NaOCl first. :-)

Is household bleach suitable, or should I prepare some pure NaOCl?

Tsjerk - 29-8-2022 at 04:41

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.

Brominerain - 29-8-2022 at 05:07

Quote: Originally posted by Tsjerk  
Just make an equimolar solution of KMnO4 and NaOH

But KMnO4 and NaOH react and make a green solution.
(It reduces to K2MnO4 in alkaline solutions)

[Edited on 29-8-2022 by Brominerain]

Tsjerk - 29-8-2022 at 05:28

Ah, yes, of course. You make the alcohol suspension alkaline.

Brominerain - 29-8-2022 at 05:52

Did a quick test and the KMnO4 reduces very slowly, even in very basic solutions.

Pumukli - 29-8-2022 at 08:55

Household bleach would do.
Search the paper which describes it, I used this method in menthol -> menthone transformation with good results.

Fery - 29-8-2022 at 10:07

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.

Texium - 29-8-2022 at 10:28

Quote: Originally posted by Brominerain  
But KMnO4 and NaOH react and make a green solution.
(It reduces to K2MnO4 in alkaline solutions)
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.

Texium - 29-8-2022 at 16:10

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.